In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into the market panic around SaaS stocks, whether AI models are actually getting better, ChatGPT's move into advertising (and Anthropic's spicy response), and the explosion of OpenClaw. They also tackle QSBS and when SaaS acquisitions shift from asset to stock purchases.

Episode Sponsors:

This episode is brought to you by Mercury

Mercury is the banking solution I use across my businesses, from my personal single-member LLC to MicroConf and TinySeed.

Traditional banking forces you to duct-tape tools together and work around slow, clunky processes. Mercury gives me a clean dashboard that shows exactly where each business stands at a glance.

The interface is simple enough for daily banking and paying invoices, but powerful enough to handle multi-step approval workflows for large transfers.

There's a reason more than 300,000 entrepreneurs have made the switch. It's free to get started with no in-person visits and no minimum balance.

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Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.

If you’ve got a strong vision but no technical partner, you need more than a “vibe-coded” MVP, you need a real foundation.

That’s where Designli comes in. Their two-week SolutionLab Prototyping Sprint pairs you with a product owner, designer, and developer to turn your idea into a beautiful, clickable prototype you’ll be proud to show investors or early users.

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Topics we cover:

• (3:52) – M&A guide for B2B SaaS founders
• (6:35) – QSBS and asset vs. stock purchase thresholds
• (9:25) – Is AI killing B2B SaaS?
• (16:27) – Are AI models noticeably better than a year ago?
• (17:27) – ChatGPT vs. Claude: real-world experiences
• (26:17) – ChatGPT ads and Anthropic's Super Bowl response
• (29:34) – The opportunity for SaaS founders in new ad networks
• (32:29) – OpenClaw: hype or substance?

Links from the show:

• MicroConf US April 12-14, 2026 · Portland, Oregon
• Discretion Capital’s M&A Guide
• TinySeed SaaS Institute
• AI is Killing B2B SaaS by Namanyay Goel
• OpenClaw is What Apple Intelligence Should Have Been by Jake Quist
• Rob Walling @robwalling | X
• Einar Vollset @einarvollset | X
• Tracy Osborn (tracymakes) | Blue Sky

If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear...

In this episode, Rob is joined by fan favorite Derrick Reimer to tackle listener questions on no-code vs. AI vibe coding, when to take small funding early vs. pure bootstrapping, whether SaaS margins will compress as AI makes building cheaper, and how to get truly useful feedback from your customers.

Want to get your question answered? Submit it here for a future episode.

Episode Sponsor:

Hiring engineers right now is kinda broken. AI resumes, fake profiles, people who look senior on paper but can't ship anything real.

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Topics we cover:

• (2:18) – No-code vs. AI vibe coding for SaaS
• (7:55) – What Rob would do as a non-developer today
• (11:10) – Will you have to rewrite AI or no-code apps later?
• (17:08) – Taking small funding early vs. bootstrapping
• (21:29) – De-risking before taking funding
• (27:42) – Will AI compress SaaS margins?
• (31:32) – Why brand and positioning still win
• (37:38) – Expanding your value chain with AI
• (39:47) – Getting actionable feedback from customers

Links from the show:

• MicroConf Europe 2026 – Join us in Reykjavík, Iceland (Sept 21–23) 
• Discretion Capital - M&A Advisory for B2B SaaS with $2-25m ARR
• SavvyCal
• SavvyCal Appointments
• TinySeed
• Derrick Reimer (@derrickreimer) | X

If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling sits down with Jay Clouse, founder of Creator Science, to explore founder-led marketing. They dig into how Jay overcame his own limiting beliefs about creativity, why most SaaS founders probably shouldn't pursue content creation, and how to evaluate whether building an audience makes sense for your specific business.

This is part one of a two-part conversation. Head to the Creator Science podcast to hear Jay interview Rob about SaaS, being a creator, and how he prioritizes his time.

Episode Sponsors:

This episode is brought to you by Mercury

Mercury is the banking solution I use across my businesses, from my personal single-member LLC to MicroConf and TinySeed.

Traditional banking forces you to duct-tape tools together and work around slow, clunky processes. Mercury gives me a clean dashboard that shows exactly where each business stands at a glance.

The interface is simple enough for daily banking and paying invoices, but powerful enough to handle multi-step approval workflows for large transfers.

There's a reason more than 300,000 entrepreneurs have made the switch. It's free to get started with no in-person visits and no minimum balance.

Apply online in minutes at mercury.com.

Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.

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Topics we cover: 

• (3:17) – What is Creator Science and who it serves
• (6:49) – “I’m not creative”: Jay’s mindset shift + advice for founders
• (11:38) – Examples of ultra-niche creator businesses 
• (13:54) – Why founders should create content for customers (not other founders)
• (19:02) – Discovery vs. relationship channels: where attention actually comes from
• (20:10) – Who Should Pursue Founder-Led Marketing? 
• (24:17) – Picking platforms based on where your customers already are
• (31:43) – Founder-involved vs. founder-led marketing

Links from the Show: 

• MicroConf Europe┃Reykjavik, Iceland · Sept 21-23
• Creator Science
• Creator Science Podcast (Part two of this conversation)
• Jay Clouse┃LinkedIn

In this solo episode, Rob Walling answers listener questions about when it’s worth taking funding to speed up your path to full-time, how to think about equity when a co-founder joins late, and whether A.I. is shifting startup risk from market risk to feasibility risk. He also breaks down how to treat a low-priced, high-churn plan as “cheapium,” when to kill it, and how to test freemium without making a decision you can’t undo.

Want to get your question answered? Drop it here.

Episode Sponsor:

Hiring engineers shouldn’t feel like sorting through AI-polished resumes.

G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills.

No time wasters. No guesswork. Just solid developers who can deliver.

G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes.

Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob 

Topics we cover: 

• (2:48) – When is it time to quit your day job, and should you raise funding to do it faster?
• (4:35) – The “emotional runway” problem (and why bootstrappers burn out)
• (10:06) – Equity splits: when to talk about it, and what actually matters
• (13:57) – Late co-founder vs. business partner: how traction changes the %
• (18:34) – Is A.I. increasing feasibility risk (aka tech risk) for startups?
• (25:01) – Should a cheap, high-churn plan be treated like a marketing channel?
• (26:19) – “Cheapium” pricing: when to keep it, kill it, or test freemium

Links from the Show: 

• Apply to TinySeed - Applications are until Feb 17th, 2026
• The SaaS Playbook by Rob Walling
• MicroConf  - Community for SaaS Founders
• Slicing Pie by Mike Moyer
• Die With Zero by Bill Perkins
• Dharmesh Shah

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling answers listener questions about when QSBS might justify a C Corp (vs. staying an S Corp or LLC), why SaaS exits are often discussed in ARR multiples rather than EBITDA, and how the profitability/growth tradeoff impacts valuation. He also shares thoughts on GMV-based pricing and where developers can learn practical, non-fluffy marketing skills.

Episode Sponsors:

This episode is brought to you by Mercury

Mercury is the banking solution I use across my businesses, from my personal single-member LLC to MicroConf and TinySeed.

Traditional banking forces you to duct-tape tools together and work around slow, clunky processes. Mercury gives me a clean dashboard that shows exactly where each business stands at a glance.

The interface is simple enough for daily banking and paying invoices, but powerful enough to handle multi-step approval workflows for large transfers.

There's a reason more than 300,000 entrepreneurs have made the switch. It's free to get started with no in-person visits and no minimum balance.

Apply online in minutes at mercury.com.

Mercury is a fintech company, not an FDIC-insured bank. Banking services provided through Choice Financial Group and Column N.A., Members FDIC.

If you’ve got a strong vision but no technical partner, you need more than a “vibe-coded” MVP, you need a real foundation.

That’s where Designli comes in. Their two-week SolutionLab Prototyping Sprint pairs you with a product owner, designer, and developer to turn your idea into a beautiful, clickable prototype you’ll be proud to show investors or early users.

Right now, Startups for the Rest of Us listeners get $3,800 off their sprint. Get started at designli.co/fortherestofus

Topics we cover: 

• (3:30) – How the QSBS tax benefit can save you millions
• (7:40) – C Corp vs. S Corp: which structure makes sense for founders
• (9:39) – Why ARR multiples matter more than EBITDA in SaaS
• (13:13) – Profitability as a drain on growth
• (17:48) – Should co-founders join the same mastermind?
• (19:16) – How to leverage GMV-based pricing in SaaS
• (22:48) – The best way for developers to learn real marketing skills
• (31:28) – Why every founder should master sales and marketing early

Links from the Show: 

• TinySeed Applications Live Q&A - February 11th, 10:00 AM EST
• Apply to TinySeed - Applications are until Feb 17th, 2026
• The SaaS Playbook by Rob Walling
• MicroConf  - Community for SaaS Founders
• Conversion Factory
• TinySeed Mentors
• Rob Walling on X (@robwalling)

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review:

In this episode, Rob Walling talks with his brother, Russ Walling, about the mindset and habits that shape long-term success from overcoming perfectionism to building resilience and learning to make tough calls without all the answers.

They discuss how growing up with a shared emphasis on hard work, sports, and achievement created both strengths and struggles and how lessons learned in construction, poker, and entrepreneurship still apply to building great companies today.

Episode Sponsor:

Hiring engineers shouldn’t feel like sorting through AI-polished resumes.

G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills.

No time wasters. No guesswork. Just solid developers who can deliver.

G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes.

Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob 

Topics we cover: 

• (04:10) – How early lessons in hard work and sports shaped mindset
• (07:46) – Learning to be comfortable being uncomfortable
• (12:03) – The dark side of perfectionism
• (16:51) – Overcoming fear of failure and learning to take risks
• (19:04) – What poker taught Russ about risk and decision-making
• (21:52) – The Armageddon Beer story 
• (28:53) – Why both brothers chose entrepreneurship
• (31:08) – Redefining leadership: collaboration over fear
• (35:24) – The three traits that drive lasting success
• (43:45) – Why hard work is still the ultimate differentiator

Links from the Show: 

• Discretion Capital M&A Advisory for SaaS Founders doing $2-25M
• The SaaS Playbook by Rob Walling
• Rob Walling (@robwalling) | X 

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling sits down with Jason Cohen, founder of SmartBear and WP Engine, to talk about building billion-dollar businesses, the future of AI for founders, and what makes small companies thrive even when the odds are stacked against them.

They dig into the early days of WP Engine, how Jason develops his frameworks, why execution beats ideas, and Jason’s framework for identifying “hidden multipliers” small, systematic changes that make an outsized impact.

Episode Sponsor:

Hiring engineers shouldn’t feel like sorting through AI-polished resumes.

G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills.

No time wasters. No guesswork. Just solid developers who can deliver.

G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes.

Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob 

Topics we cover: 

• (03:45) – The core idea behind Hidden Multipliers
• (09:24) – Writing as a way of thinking
• (12:34) – Why sharing your frameworks matters
• (14:14) – The origin of “Designing the Ideal Bootstrap Business”
• (18:10) – The hidden weak links in every startup
• (21:25) – De-risking and niching down effectively
• (24:56) – Why narrowing your focus expands your reach
• (26:24) – Building WP Engine in a commodity market
• (29:37) – Out-executing funded competitors
• (31:52) – Finding product–market resonance through pricing
• (32:40) – How brand actually develops
• (37:54) – Building in the age of AI: pitfalls and opportunities
• (41:52) – The three categories of AI startups today
• (46:02) – Why 10x improvement is the new baseline for differentiation
• (49:19) – The real moat in the age of AI

Links from the Show: 

• MicroConf US 2026 – Portland, April 14–16, 2026  Promo Code: Rob50 for $50 off
• The SaaS Playbook
• PREORDER Hidden Multipliers by Jason Cohen
• Designing the Ideal Bootstrapped Business with Jason Cohen
• A Smart Bear Blog
• Jason Cohen (@asmartbear) | X 

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling covers a wide range of topics and dives into three areas every founder should master: how to develop an editorial eye (or “taste”), the difference between persistence and obstinance, and why focus, not diversification remains the hardest, most valuable entrepreneurial skill.

Episode Sponsor:

Hiring engineers shouldn’t feel like sorting through AI-polished resumes.

G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills.

No time wasters. No guesswork. Just solid developers who can deliver.

G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes.

Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob

Topics we cover: 

• (1:55) – How to develop an “editorial eye” (and why it matters for founders)
• (7:03) – When to get out of the way and let true experts lead
• (8:07) – Why your product must start with a real problem (not just an idea)
• (9:11) – Paul Graham’s The Right Kind of Stubborn: persistence vs. obstinance
• (12:03) – Are you attached to your goal or just your first idea?
• (13:44) – How great founders adapt to new data without losing momentum
• (14:44) – Sam Parr on why “constant switching will kill you”
• (16:30) – Focus as a founder’s hardest and most valuable skill
• (16:49) – Why “Triple, Triple, Double, Double” isn’t dead (despite VC takes)
• (18:34) – The problem with clickbait startup advice

Links from the Show: 

• MicroConf Europe 2026 – Join us in Reykjavík, Iceland (Sept 21–23) - Promo Code: ROB50
• The Mom Test by Rob Fitzpatrick
• Paul Graham: “The Right Kind of Stubborn”
• Sam Parr (@thesamparr) | X 
• Harry Stebbings (@HarryStebbings) | X
• Rob Walling YouTube Channel
• The SaaS Playbook

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTune...

In this solo episode, Rob Walling shares 11 unexpected lessons from his own day jobs, from courier to electrician to engineering manager, and how each role quietly taught him skills that shaped his success as a SaaS founder. He dives into the value of curiosity, self-education, and learning to lead before you ever start a company.

Episode Sponsor:

If you’ve got a strong vision but no technical partner, you need more than a “vibe-coded” MVP, you need a real foundation.

That’s where Designli comes in. Their two-week SolutionLab Prototyping Sprint pairs you with a product owner, designer, and developer to turn your idea into a beautiful, clickable prototype you’ll be proud to show investors or early users.

Right now, Startups for the Rest of Us listeners get $3,800 off their sprint.

Get started at designli.co/fortherestofus

Topics we cover: 

• (2:03) – Why every day job can teach entrepreneurial skills
• (4:44) – Lesson #1: Figuring things out when instructions are unclear
• (7:27) – Lesson #2: Learning to respect other people’s time
• (9:05) – Lesson #3: How early self-education compounds over time
• (11:33) – Lesson #4: Embracing hard, unglamorous work
• (14:09) – Lesson #5: Why experience always beats credentials
• (16:42) – Lesson #6: Letting the buck stop with you
• (17:44) – Lesson #7: Knowing when to cut corners (and when not to)
• (20:11) – Lesson #8: Finding the right people to work with
• (21:33) – Lesson #9: Managing and motivating people as a learned skill
• (23:53) – Lesson #10: Turning hiring and firing into Founder superpowers
• (26:11) – Lesson #11: The value of exposure to well-run systems

Links from the Show: 

• MicroConf Mastermind Matching – Apply before January 16th
• The SaaS Playbook by Rob Walling
• Good to Great by Jim Collins
• Seven Habits of Highly Effective People by Stephen R. Covey
• Think and Grow Rich by Napoleon Hill
• MicroConf
• Rob Walling @robwalling) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review:

In this episode, Rob Walling talks with Laura Roeder, founder of Paperbell, about how her lean, fully-bootstrapped team outlasted and outperformed a VC-funded rival. They discuss what the venture-backed company got wrong, how Paperbell focused on the right customers, and why efficiency still beats funding.

Topics we cover: 

• (3:52) – Competing against a $10M-funded startup
• (8:45) – Why “self-serve SaaS on hard mode” was worth it
• (14:36) – How over-investing in engineering killed their competitor
• (19:04) – The real problem with under-investing in marketing
• (21:19) – Why some SaaS markets can’t scale upmarket
• (24:13) – Why some markets are perfect for bootstrappers
• (28:42) – How big funding rounds create false signals
• (30:24) – The behind-the-scenes of a potential acquisition deal
• (33:26) – How Paperbell became the market leader

Links from the Show: 

• MicroConf Mastermind Matching
• The SaaS Playbook by Rob Walling
• Paperbell
• Laura Roeder (@lkr) | X 

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling revisits his predictions for 2025, what he got right, what he totally missed and shares nine new predictions for 2026. He reflects on trends shaping bootstrapped SaaS, from the rise of AI-first startups to the challenges facing horizontal SaaS founders. 

Interested in Sponsoring this Podcast?

If your product or service helps SaaS founders, bootstrappers, or indie entrepreneurs, you can reach thousands of listeners each week through Startups for the Rest of Us.

Email us at sponsors@startupsfortherestofus.com

Topics we cover: 

• (1:09) – Lessons from common SaaS plateaus and the Core Four framework
• (4:39) – Rating his 2025 predictions: what came true (and what didn’t)
• (12:46) – Prediction #1: Horizontal SaaS will face major headwinds
• (15:56) – Prediction #2: Overreliance on SEO will hurt SaaS founders
• (16:26) – Prediction #3: Top brands will dominate as AI narrows discovery
• (21:04) – Prediction #4: The AI VC bubble won’t burst in 2026
• (21:47) – Prediction #5: Open source AI models will double in usage
• (22:28) – Prediction #6: A major no code platform will struggle or shut down
• (23:33) – Prediction #7: M&A for small SaaS startups will accelerate
• (24:31) – Prediction #8: Bitcoin will hit a new all-time high
• (25:31) – Prediction #9: Stripe will not go public (again)
• (26:26) – Reflections on MicroConf and TinySeed milestones

Links from the Show: 

• MicroConf US – Portland, April 2026
• Rob Walling YouTube Channel
• Apply to TinySeed
• TinySeed Portfolio
• The SaaS Playbook by Rob Walling

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling shares the 2025 State of TinySeed, from its first fund in 2018 to a global portfolio of over 210 B2B SaaS companies. He reflects on TinySeed’s growth, what the data reveals about today’s founders, funding trends, and the rise of AI-first startups.

Topics we cover: 

• (1:46) – How TinySeed began and the doubts it faced 
• (3:51) – Growing to 210+ portfolio companies and $60M raised
• (11:15) – The rise of AI-first startups and “vibe-coded” apps
• (13:09) – Record application numbers and founder trends in 2025
• (19:58) – Why vertical SaaS is outperforming horizontal SaaS
• (21:59) – The importance of founder community and shared experience
• (25:06) – How TinySeed and MicroConf create long-term founder connections

Links from the Show: 

• Apply to TinySeed
• Invest in TinySeed
• TinySeed MentorsAccelerator Program Details — TinySeed
• TinySeed Portfolio
• The SaaS Playbook by Rob Walling
• MicroConf - Community for Bootstrapped SaaS Founders

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling answers listener questions about when to delegate key founder skills, whether great founders can succeed with any idea, and the limits of no-code or “vibe-coded” apps. 

To help answer one question, he calls up Ruben Gamez to get his insights on what “good” freemium retention really looks like and why the shape of your retention curve matters more than the number itself.

Want to get your question answered? Drop it here.

Episode Sponsor:

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That’s why Max Sinclair, a five-year MicroConf attendee, built SaaS Ads Studio  a software platform that combines AI with proven ad agency expertise to help SaaS founders launch, write, and optimize Google Ads campaigns.

Think of it as an agency team in a box that gets you to a profitable Google Ads engine in about six months.

Start for free at saasadsstudio.com and be one of the first 50 listeners to use code ROBWALLING for 50% off your first year.

 Topics we cover: 

• (2:51) – What’s a “good” freemium retention rate?
• (4:59) – How freemium retention differs for mobile vs. SaaS apps
• (9:51) – When to start delegating the Core Four SaaS skills
• (12:53) – How to hand off sales, marketing, product, and dev the right way
• (23:28) – Can great founders succeed with any product idea?
• (29:34) – Should founders avoid building on no-code or third-party platforms?

Links from the Show: 

• MicroConf Connect 
• TinySeed SaaS Institute
• The SaaS Playbook
• SaaS Launchpad
• SignWell
• Ruben Gamez | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a new round of listener questions. They dig into the best AI coding stacks right now, how to ship fast without losing polish, whether AI is changing the kind of risk founders face, and when to start taking security seriously.

Episode Sponsor:

Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today's sponsor, Designli.

They specialize in helping founders like you who are stuck with messy code, unclear roadmaps, or a dev team that just doesn’t get it.

And for listeners of the pod, Designli is offering their Impact Week completely free. That’s a one-week, no-obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next.

If it’s a fit, you can move on to SolutionLab, a three-week sprint where Designli takes over your codebase and architects a real roadmap for growth, led by a full-time, cross-functional team.

If your tech is the bottleneck to your next stage of growth, check them out at https://designli.co/fortherestofus.

 Topics we cover: 

• (2:03) – What’s the best A.I. coding stack for developers right now?
• (11:14) – How can solo founders ship fast without sacrificing polish?
• (21:55) – Is A.I. shifting startup risk from market fit to feasibility?
• (31:44) – When should SaaS founders start worrying about security?
• (44:30) – SavvyCal’s latest product expansion

Links from the Show: 

• Call for Speakers – Apply to speak at MicroConf US in Portland
• Claude Code
• Windsurf
• Cursor
• GitHub Copilot
• VS Code
• Visual Studio
• SavvyCal Appointments
• Derrick Reimer | LinkedIn
• Derrick Reimer (@derrickreimer) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling sits down with Craig Hewitt, founder of Castos, to dive deep into Craig’s “100 Days of AI” YouTube series. They discuss the lessons learned from exploring the latest AI tools for founders, why ChatGPT might not be the best option for SaaS entrepreneurs, and which AI platforms are actually moving the needle. 

Rob and Craig also chat about the realities of AI agents, the challenges of building a second product after hitting a growth plateau, and Craig’s approach to evaluating new opportunities as he looks to expand beyond podcast hosting.

Episode Sponsor:

AI is transforming how people discover brands and Ahrefs is helping SaaS companies stay ahead.

They’ve just launched Brand Radar, a new tool that lets you track your visibility in AI platforms like ChatGPT, Perplexity, and Google’s AI Overviews. See how you stack up against competitors, monitor reputation, and build authority across search, social, and AI.

No more cobbling together tools. Ahrefs brings it all into one powerful SaaS marketing platform, backed by 15+ years of real-world web data and marketing-savvy AI.

Try it free at ahrefs.com/awt.

Topics we cover: 

• (03:28) – 100 Days of AI YouTube series, biggest surprises and key takeaways
• (08:20) – Claude Code, ChatGPT, and Manus: Which AI tools work best for founders
• (13:00) – Practical AI workflows in content production and automation
• (18:35) – AI agent cuts customer support in half
• (21:27) – Burnout and breakthroughs from publishing 100 videos in 100 days
• (25:43) – Craig’s new AI projects and what’s next
• (30:14) – Three new product ideas under evaluation
• (33:09) – The pros, cons, and emotions behind launching a second product

Links from the Show: 

• MicroConf US 2026- April 12-14, 2026 · Portland US
• TinySeed’s SaaS Institute
• Claude Code (by Anthropic) 
• Manus 
• Creator Hooks
• Cursor
• HelpScout
• DocsBot
• LinkBerry.ai – Craig’s new tool for LinkedIn content creation
• Castos
• Craig Hewitt | YouTube
• Craig Hewitt | LinkedIn
• Craig Hewitt (@TheCraigHewitt) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling tackles listener questions and shares practical frameworks for what to do when your product hits a plateau, explains why “autopilot” often leads to decline, and outlines when founders should seriously consider SOC 2 compliance. Rob also talks about balancing a startup with a newborn, the real value of open source and IP, and the risks and rewards of building MVPs in exchange for equity.

Want to get your question answered? Drop it here.

Episode Sponsor:

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Whether you need a fractional CTO or experienced engineers to accelerate development, Gearheart plugs directly into your workflow and delivers. They’ve built 70+ products, including SmartSuite, which raised $38M and is used by companies like Capital One.

As a listener, you get the first 20 hours of development free when you mention the podcast.

gearheart.io

Topics we cover: 

• (2:34) – What to do with a plateaued $500k B2C app
• (4:28) – Founder motivation, business longevity, and the myth of autopilot
• (13:15) – Should you offer MVP development in exchange for equity?
• (14:04) – Equity risks, upside, and how to protect yourself
• (18:00) – When SOC2 compliance actually matters for founders
• (21:08) – Balancing a new baby, a job, and SaaS ambitions
• (24:38) – Can open source IP help bootstrappers stand out?
• (25:25) – Why differentiation and marketing matter more than patents or code

Links from the Show: 

• Discretion Capital – M&A Advisory for B2B SaaS with $2-25m ARR
• MicroConf Connect
• TinySeed SaaS Institute

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling tackles a fresh batch of listener questions, starting with one of the most common dilemmas for technical founders: should you hire a sales and marketing co-founder or go it alone?

He introduces his “Core Four” mental model, the essential skills every SaaS team needs early on, and shares insights on dealing with enterprise clients who keep moving the goalposts, handling a flood of non-ICP users, and a heartfelt message from a listener who just exited their startup.

Want to get your question answered? Drop it here.

Episode Sponsor:

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As a listener, you’ll get a 7-day free trial plus $1,500 off your first invoice when you mention this podcast.

Head over to https://www.g2i.co/microconf  to get started.

Topics we cover: 

• (3:11) – Should you find a co-founder for sales and marketing?
• (5:29) – What are the Core Four SaaS Skills?
• (11:41) – Can you succeed without mastering all four, or should you outsource?
• (16:39) – Why sales-led growth might outperform self-serve SaaS
• (21:48) – Dealing with big companies who change your contract terms
• (27:06) – What to do with thousands of unqualified signups

Links from the Show: 

• Discretion Capital – M&A for B2B SaaS
• Exit Strategy by Sherry & Rob Walling 
• MicroConf - SaaS Community
• TinySeed - SaaS Institute

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling chats with Philippe Lehoux about how he and his co-founders bootstrapped Missive, a collaborative email and team inbox tool. They deep dive into landing early customers, unique horizontal positioning, content-driven growth, enterprise sales, and how to compete with VC-backed competition. 

Episode Sponsor:

Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today's sponsor, Designli.

They specialize in helping founders like you who are stuck with messy code, unclear roadmaps, or a dev team that just doesn’t get it.

And for listeners of the pod, Designli is offering their Impact Week completely free. That’s a one-week, no-obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next.

If it’s a fit, you can move on to SolutionLab, a three-week sprint where Designli takes over your codebase and architects a real roadmap for growth, led by a full-time, cross-functional team.

If your tech is the bottleneck to your next stage of growth, check them out at https://designli.co/fortherestofus.

 Topics we cover: 

• (2:05) – Missive’s $8M ARR journey and email pivot
• (6:02) – Early idea and first customers
• (11:16) – Unique positioning: horizontal vs. vertical
• (13:41) – How they prioritize features
• (15:39) – Why they stayed bootstrapped and decline funding
• (20:25) – Content strategy and “vs” pages
• (21:39) – Affiliate program driving 30% of growth
• (25:24) – Challenges and benefits of being horizontal
• (30:28) – Enterprise sales and pricing
• (32:06) – Scaling with SOC 2 compliance

Links from the Show: 

• SaaS Institute 
• MicroConf YouTube channel
• Missive
• Philippe Lehoux | LinkedIn
• Philippe Lehoux (@plehoux) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling covers several founder-focused topics: the difference between gatekeeping and paying your dues, why raw material beats polish, and why successful people don't mind others winning. He also shares a listener's exit story, discusses optimism in founder communities, and talks about the mix of luck, skill, and hard work needed to build something that lasts.

Episode Sponsor:

AI is transforming how people discover brands and Ahrefs is helping SaaS companies stay ahead.

They’ve just launched Brand Radar, a new tool that lets you track your visibility in AI platforms like ChatGPT, Perplexity, and Google’s AI Overviews. See how you stack up against competitors, monitor reputation, and build authority across search, social, and AI.

No more cobbling together tools. Ahrefs brings it all into one powerful SaaS marketing platform, backed by 15+ years of real-world web data and marketing-savvy AI.

Try it free at ahrefs.com/awt.

 Topics we cover: 

• (2:00) – Gatekeeping vs. Paying dues as a new founder
• (9:56) – How “raw material” transforms into high-value skills (and startups)
• (16:36) – A bootstrapped listener shares a quiet, life-changing exit
• (18:17) – People who are winning don’t mind if others win too
• (20:09) – The critical importance of who you surround yourself with

Links from the Show: 

• MicroConf Remote - Nov 5th, 2025 | Use promo code STARTUPS15 for $15 off your ticket.
• The SaaS Playbook
• 1000-Gram Iron Bar Analogy 

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling answers a fresh batch of listener questions covering SaaS marketing, global expansion, and strategic positioning. He shares advice on whether inventing a new product category is ever worth it and the nuances of updating your positioning after launch.

Want to get your question answered? Drop it here.

 Topics we cover: 

• (2:53) – Vertical vs. horizontal vs. orthogonal positioning as a bootstrapper
• (12:37) – Is AI making it easier to create a new category?
• (21:19) – How to break through mental blocks and actually launch
• (28:36) – Local vs. global marketing for SaaS
• (33:01) – Self-driving cars: Rob’s past prediction and what reverse statistics can teach founders

Links from the Show: 

• MicroConf Remote - Nov 5th, 2025 | Use promo code STARTUPS15 for 15% off your ticket.
• TinySeed - SaaS accelerator for ambitious B2B founders
• Invest in TinySeed 
• Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit
• Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling and Laura Sprinkle, founder of Rootabl, recap MicroConf Europe 2025 in Istanbul. They discuss the MicroConf vibe, standout talks on AI, affiliate marketing, and SaaS growth, as well as the value of networking and connecting while getting outside the conference room. 

 Topics we cover: 

• (5:01) – The friendly, diverse MicroConf crowd
• (8:06) – Impressions on Istanbul
• (9:24) – Marc Thomas on lifecycle marketing
• (11:34) – Michelle Hansen & John Knox on networking 
• (13:04) – MicroConf Excursions
• (16:45) – Einar Volset on SaaS Buyers
• (20:27) – Rob’s AI talk
• (23:27) – Laura’s talk about affiliate programs
• (24:47) – Jesse Schoberg on ranking in ChatGPT and Google's AI
• (26:31) – Attendee-Led Workshops
• (27:58) – Kevin Sahin’s unfiltered lessons scaling to $2M
• (31:12) – James Mooring’s journey to $2M ARR

Links from the Show: 

• Get your Ticket for MicroConf - Portland, Oregon, on April 12 -14, 2026 | Use promo code ROB50 for $50 off your ticket.
• TinySeed
• Join MicroConf Connect
• Deploy Empathy by Michelle Hansen
• The Hard Thing About Hard Things by Ben Horowitz
• There’s ONLY 5 Ways to Use AI in SaaS (prove me wrong)
• Rob Walling (@robwalling) | X
• Rootabl
• Laura Sprinkle | LinkedIn
• Laura Sprinkle (@imlaurasprinkle) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling flies solo, answering your questions on marketing and audience building. He covers what to do when your channels stop scaling, where to publish early on, and the "media company first" approach.

Episode Sponsor:

Are you a non-technical founder with solid revenue and real traction, but your technology is holding you back? You should check out today's sponsor, Designli.

They specialize in helping founders like you who are stuck with messy code, unclear roadmaps, or a dev team that just doesn’t get it.

And for listeners of the pod, Designli is offering their Impact Week completely free. That’s a one-week, no-obligation audit where their team dives into your code, your design system, and your product roadmap to show you exactly what’s working, what’s broken, and what needs to happen next.

If it’s a fit, you can move on to SolutionLab, a three-week sprint where Designli takes over your codebase and architects a real roadmap for growth, led by a full-time, cross-functional team.

If your tech is the bottleneck to your next stage of growth, check them out at https://designli.co/fortherestofus.

Topics we cover: 

• (1:50) – Can a SaaS founder exit through a management buyout?
• (6:46) – What to do when your marketing isn't scaling anymore
• (16:28) – How to market a product while searching for product-market fit
• (23:27) –  Where to publish content when building an audience from scratch
• (27:38) – Should you build a media company before launching your SaaS?

Links from the Show: 

• Get your Ticket for MicroConf Remote - November 5, 2025
• Exit Strategy
• The SaaS Playbook
• Rob Walling (@robwalling) | X
• Episode 576 | Don’t Become a Media Company (A Rob Solo Adventure)

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a listener Q&A. They break down what it takes to compete with well-funded incumbents, how to decide whether to pivot or push forward, when a technical co-founder is truly necessary, the right time to think about trademarks, and the difference between “good churn” and “bad churn” especially when customers fall outside your ICP.

Episode Sponsor:

AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead.

With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more.

You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business.

There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world. 

Try it free at ahrefs.com/awt.

Topics we cover: 

• (3:35) – Competing with well-funded incumbents
• (12:47) – Should you focus on competitors or customers?
• (20:20) – Pivot, press on, or move on: how to decide
• (29:09) – Finding and vetting a technical co-founder or partner
• (39:04) – When should you pursue trademarks?
• (44:24) – Is churn ever good for a startup?

Links from the Show: 

• MicroConf US 2026 - Portland, Oregon - Use Promo Code ROB50 for $50 off.
• MicroConf Connect
• BIMI (Brand Indicators for Message Identification)
• SavvyCal
• Derrick Reimer | LinkedIn
• Derrick Reimer (@derrickreimer) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 800, Rob Walling goes solo for a special milestone installment of Startups For the Rest of Us. He covers the 12 foundational commandments that shape his approach to SaaS, hard-won lessons forged from years of building, investing in, and advising startups.

Topics we cover: 

• (3:46) – #1: Nuance beats absolutes
• (6:52) – #2: Make hard decisions with incomplete information
• (9:16) – #3: Avoid the classic traps
• (12:22) – #4: Don't build without real evidence
• (15:14) – #5: Marketing beats product
• (19:08) – #6: Fewer customers, better customers
• (21:01) – #7: Respect (and fear) the platform
• (24:04) – #8: Build your network, not just your audience
• (26:30) – #9: Overnight success takes a decade
• (28:45) – #10: Stack small wins
• (31:22) – #11: Be careful who you listen to
• (33:15) – #12: The hardest battles are in your own head

Links from the Show:

• MicroConf US 2026 - Portland, Oregon - Use Promo Code ROB50 for $50 off.
• Invest in TinySeed Fund Three
• SaaS Playbook
• The Entrepreneur's Guide to Keeping Your Sh*t Together
• Exit Strategy
• Episode 685 | 7 Things You Should Never Do
• Episode 700 | Playing the Long Game
• Episode 735 | The 8 Levels of SaaS Platform Risk

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here, from choosing not to raise funding (for now), to planning a laser tag event no committee would approve, to what comes next on the road to $1M.

Topics we cover: 

• (1:49) – Crossing $500k ARR and building personal health habits
• (5:36) – The big levers behind OutboundSync’s growth
• (6:39) – Laser tag, not hotel happy hours
• (13:01) – Deciding not to raise more funding (for now)
• (16:25) – An overbuilt tech stack 
• (17:57) – Competitors, copycats, and growing a brand
• (19:06) – The next chapter for OutboundSync
• (23:29) – Ambition, TinySeed, and channeling energy
• (25:14) – Harris’s advice for founders still grinding

Links from the Show: 

• Invest in TinySeed Fund Three
• Coaching Call Bonus
• OutboundSync
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling chats with Colin Bartlett about how he and his co-founder Andy transformed a side project monitoring tool into a seven-figure ARR business that now serves as an early warning system for outages across 6,000+ services. 

From nearly abandoning the product during three stagnant years to discovering their killer differentiation, Colin's journey is a masterclass in patient iteration, finding product-market fit the hard way, and why sometimes the most boring infrastructure businesses make the best SaaS companies.

Episode Sponsor:

You’ve probably heard that ChatGPT can do all of your marketing. But that’s nonsense unless your strategy is blindly following tired, recycled, outdated strategies. 

If you care about systematically creating a marketing engine that converts, not just throwing spaghetti at the wall to see what sticks, you need real humans who actually understand positioning, persuasion, and modern customer acquisition playbooks. 

That’s Conversion Factory. They’re a SaaS marketing and design agency that have worked with over 50 startups, including several TinySeed companies. 

Book a call at conversionfactory.co and mention this podcast for $1,000 off your first month. And if you’re at MicroConf Europe next week, make sure to connect with Corey Haines in the hallway track. 

Topics we cover: 

• (3:08) – How StatusGator detects outages (and why users are part of the signal)
• (6:23) – From side project to SaaS: the early days of building StatusGator
• (8:46) – Shifting the ICP: Why developers weren’t the buyers
• (11:44) – SEO as the engine behind thousands of trials
• (17:00) – Hitting early MRR milestones and hiring the first marketer
• (25:12) – How TinySeed funding unlocked a full product redesign
• (32:05) – Building a dual funnel to boost ACV and win enterprise deals
• (38:00) – Advice for other SaaS founders playing the long game

Links from the Show: 

• Invest in TinySeed Fund Three
• MicroConf Mastermind Matching - Applications open until September 24th
• StatusGator
• Colin Bartlett | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every opportunity comes with a trade-off. They explore the tension between raising funds you don't need, staying focused when good ideas keep coming, and building a business while raising a family.

Topics we cover: 

• (2:28) – From $20k to $35k MRR in three months
• (2:53) – The bets that moved the needle
• (4:56) – Infinite runway, SOC 2 wins, and building trust
• (8:29) – Saying no to good ideas with limited bandwidth
• (10:00) – Decision-making, value-driven growth, and agency DNA
• (13:14) – Should Harris raise more funding or stay focused?
• (15:52) – Why boring “pipes” matter in an AI world
• (20:25) – Trade-offs, mindset, and building for scale
• (25:35) – Hiring a sales coach and focusing on what works
• (27:52) – Balancing startup stress with parenting

Links from the Show: 

• SaaS Institute
• Coaching Call Bonus
• OutboundSync
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo adventure episode, Rob Walling unpacks why SaaS marketing feels harder than ever and why most advice out there will waste your time. He shares how he’d approach things if growth has stalled, the questions he’d ask first, and why real progress comes from proven fundamentals.

Episode Sponsor:

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CTOs and engineering managers trust them to deliver critical features end-to-end with minimal oversight, whether it's fixing scaling failures, broken integrations, or system instability. 

With 13 years of experience building sophisticated B2B platforms, they plug in fast and deliver results. They've helped build platforms like SmartSuite, which has scaled to thousands of organizations including industry giants like Capital One.

Book your free strategy session at gearheart.io and mention this podcast to get 20% off discovery or embedded engineers for your team. That's gearheart.io.

Topics we cover: 

• (2:20) – Why marketing is harder than ever, and what’s changed
• (3:40) – The Dunning-Kruger Effect 
• (11:30) – Marketing is not just convincing someone to buy what you've built.
• (16:30) – Validating vs. throwing dice at a wall
• (20:03) – Is there a ‘one right way’ to grow a business?
• (25:00) – Be careful who you listen to

Links from the Show: 

• MicroConf Events
• MicroConf Mastermind Matching
• 75+ SaaS Marketplaces 
• The SaaS Playbook
• TinySeed
• Rob Walling (@robwalling) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode of TinySeed Tales, Rob Walling celebrates with Harris Kenny after OutboundSync crosses $20k MRR ahead of schedule. They talk about why hitting a milestone can feel both exciting and overwhelming, the arrival fallacy, and how simple, consistent execution may be all it takes to reach $30k. Harris shares the bets that moved the needle, including Salesforce, SOC 2, and what hidden demand taught him about building integrations before anyone asked.

Topics we cover: 

• (1:32) – Crossing $20k MRR and aiming for $30k
• (6:29) – The Salesforce bet
• (8:17) – Runway, burn, and pricing upmarket
• (10:34) – Raise capital or keep bootstrapping
• (15:03) – SOC 2 as a sales unlock
• (20:11) – Marketplace credibility and AppExchange
• (22:05) – Hidden demand for Salesforce
• (26:11) – The push to $30k and parity

Links from the Show: 

• Invest in TinySeed Fund 3
• Coaching Call Bonus
• MicroConf Events
• OutboundSync
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling talks with longtime listener Zamir Khan, founder of VidHug (now Memento). Zamir’s story broke a lot of SaaS “rules”: B2C, low price point, one-time payments, and years of slow growth. He shares how he nearly gave up, the pandemic surge that changed everything, and the emotional ride that led to a life-changing exit.

Episode Sponsor:

AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead.

With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more.

You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business.

There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world. 

Try it free at ahrefs.com/awt.

Topics we cover: 

• (3:47) — From podcast listener to SaaS founder
• (7:59) — The role of luck, timing, and the pandemic in growth
• (18:37) — A birthday gift becomes a product
• (23:54) — Charging early and surviving slow growth
• (30:47) — From $1k a month to 80k daily users
• (39:58) — Support load, stress, and the edge of burnout
• (48:58) — Deciding to sell (and why timing mattered)
• (52:57) — Life after the exit: slowing down and finding balance

Links from the Show: 

• TinySeed – Applications close tonight!
• MicroConf Connect – The community for SaaS founders
• The SaaS Playbook 
• Memento (formerly VidHug)
• Zamir Khan (@zam1rkhan) | X
• Zamir Khan  | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus.

Topics we cover: 

• (1:40) – Closing his biggest deal ever and what it unlocked
• (4:26) – Learning how to do enterprise sales
• (6:20) – How SOC 2 made the product stronger
• (12:18) – New hires are paying off
• (18:23) – Building the Salesforce integration
• (22:13) – Getting pull from the market, not pushing
• (24:10) – Taking customers from unicorns 

Links from the Show: 

• TinySeed SaaS Accelerator - Applications close on September 9th
• Coaching Call Bonus
• Invest in TinySeed
• YNAB (You Need A Budget)
• Dynamite Jobs
• OutboundSync
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal.

Episode Sponsor

This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up.

Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at.

Book your free strategy session at gearheart.io and mention Startups for the Rest of Us to get 20% off discovery, validation, or prototyping services.

Topics we cover: 

• (3:12) – TinySeed returns Fund One
• (9:40) – GPT-5: Upgrade or letdown?
• (19:19) – Are we in an AI bubble?
• (24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees
• (31:06) – The bigger problem: Are startups forgetting to share the upside?
• (40:05) – Lifestyle vs. Ambitious Bootstrapping

Links from the Show: 

• TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd
• TinySeed SaaS Accelerator - Applications are Open!
• Invest in TinySeed
• MicroConf
• SaaS Institute
• Discretion Capital 
• Einar Vollset | LinkedIn
• Einar Vollset (@einarvollset) | X
• Tracy Osborn 
• Tracy Osborn | LinkedIn
• Tracy Osborn (@tracymakes) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.

Topics we cover: 

• (2:27) – Launching a lower-priced version and building expansion revenue
• (6:40) – How lead-gen shops are outpacing legacy rev ops
• (12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
• (18:15) – A surprise Salesforce breakthrough and what it means for product strategy
• (24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check

Links from the Show: 

• Join the TinySeed Mailing List
• Apply for TinySeed - Applications reopen September 1, 2025
• OutboundSync
• Harris Kenny | LinkedIn
• Coaching Call Bonus
• Dynamite Jobs
• Vanta

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Vera, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every founder faces, and what happens if you don’t adapt.

Topics we cover: 

• (3:27) – How the founder/CEO role changes as your SaaS scales
• (8:44) – The turning point where systems and processes matter
• (14:49 – When to hand off marketing, sales, or product as a founder
• (19:44) – Why setting context is your #1 job as a founder-CEO
• (28:19) – Why hiring right (and firing fast) makes or breaks scaling

Links from the Show: 

• SaaS Institute
• MicroConf | The community for SaaS founders
• MicroConf YouTube Channel
• People Engineering 
• The SaaS Playbook 
• Yaniv Bernstein | LinkedIn
• Yaniv Bernstein (@ybernsteindig) | X
• The Startup Podcast

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owners are never able to make. 

Topics we cover: 

• (2:25) – From agency owner to TinySeed-backed SaaS
• (6:38) – Walking away from consistent agency revenue to go all-in on SaaS
• (13:51) – Going all-in vs. splitting focus
• (16:13) – Why most agencies fail at SaaS
• (28:15) – What’s working, what’s not, and what’s next

Links from the Show: 

• Join the TinySeed Mailing List - Applications reopen in September 2025
• Apply for TinySeed
• Coaching Call Bonus
• MicroConf Connect
• OutboundSync
• The SaaS Playbook
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction.

Want to get your questions answered? Drop them here.

Topics we cover: 

• (2:33) – Do you need a co-founder to succeed in SaaS?
• (5:18)  – The Risks of AI-Generated Code and “Vibe Coding”
• (13:50) – How to manage scope creep as a solo founder
• (23:32) – Finding and retaining great contractors
• (39:43) – How to build a startup culture with a bias for action

Links from the Show: 

• MicroConf Europe | Istanbul, Sep 28-30, 2025
• TinySeed Tales Podcast
• MicroConf Connect
• TinySeed Fund
• SavvyCal
• Derrick Reimer | LinkedIn
• Derrick Reimer (@derrickreimer) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.

Topics we cover: 

• (2:30) – From FinChat to Fiscal.ai: rebranding and repositioning
• (6:50) – Why they raised a $10M Series A
• (13:09) – From bootstrapped to venture-backed: what changes?
• (19:56) – Becoming a real CEO at 25 employees
• (26:44) – Why they shut down a $1.5M product
• (30:30) – Lessons from having four co-founders
• (33:13) – The benefits of joining TinySeed

Links from the Show: 

• MicroConf Connect
• The Great CEO Within
• TinySeed: SaaS Institute
• Fiscal.ai (formerly FinChat)
• Braden Dennis (@BradoCapital) | X
• Braden Dennis | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling welcomes back Kevin Wagstaff, co-founder of Spectora, to answer listener questions about early traction in Facebook groups, finding product-market fit, handling criticism, and what it really took to bootstrap to a $90M exit.

Want to get your questions answered? Drop them here.

Topics we cover: 

(3:15) – Early traction using Facebook groups (7:17) – The tradeoff between growth and work-life balance (12:26) – Participating inside Facebook groups run by rivals (14:39) – Ranking for niche SEO terms (19:06) – Funding the early days through consulting (25:14) – Surviving churn in a seasonal, high-turnover market

Links from the Show: 

• SaaS Institute
• Mark Cuban Blog Post
• Kevin Wagstaff | LinkedIn
• Kevin Wagstaff (@KevinWagstaff3) | X
• Spectora

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling answers listener questions about picking between two SaaS ideas, product positioning, and how to know when to stop working on a project. Want to get your question answered? Drop them here.

Topics we cover: 

• (3:06) – Choosing between two AI products
• (9:38) – Will early niche positioning hurt future growth?
• (14:51) – At what point would you consider lowering prices?
• (22:35) – Narrowing your ICP and product focus
• (28:07) – How do you spec agency projects?
• (30:10) – Should you keep building on a changing platform?

Links from the Show: 

• MicroConf Europe | Istanbul, Sep 28-30, 2025
• SaaS Launchpad
• TinySeed
• The SaaS Playbook 
• MicroConf Connect

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling chats with Nick Maggiulli about his new book, The Wealth Ladder. Nick explains how to identify your current financial stage and what it really takes to move up. They dig into how wealth changes your spending habits, why exits (not salaries) drive significant changes in net worth, and how your definition of freedom might evolve over time.

Topics we cover: 

• (6:07) – Defining the six levels of wealth
• (11:49) – Why earning more isn’t enough
• (14:17) – How entrepreneurs build wealth
• (15:15) – The “0.01%” spending rule
• (31:13) – Can money actually make you happier?

Links from the Show: 

• Invest in TinySeed
• Of Dollars And Data 
• The Wealth Ladder by Nick Maggiulli
• Just Keep Buying by Nick Maggiulli
• The E-Myth Revisited by Michael E. Gerber 
• Nick Maggiulli | LinkedIn
• Nick Maggiulli (@dollarsanddata) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this week's episode, Rob Walling talks with Pierre de Wulf, co-founder of ScrapingBee, about how they mostly bootstrapped their web scraping SaaS to $5 million ARR and an eight-figure all-cash exit. They explore the pivotal shift that took them from $7K MRR to nearly $1M ARR in just 15 months, what Pierre splurged on post-exit, and the emotional, legal, and strategic complexities of selling a company.

Topics we cover: 

• (3:31) – Why they chose to sell
• (5:41) – Post-exit emotions and celebrations
• (9:57) – Lessons from failed startups before ScrapingBee
• (13:16) – From 8k to $1m ARR in 15 months
• (17:14) – Building a scalable SEO content engine
• (29:19) – Handling a major cease-and-desist

Links from the Show: 

• MicroConf Connect
• MicroConf Talk by Pierre de Wulf
• The Java Web Scraping Handbook
• ScrapingBee Blog
• TinySeed
• Discretion Capital
• Pierre de Wulf (@PierreDeWulf) | X
• Pierre de Wulf | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this solo episode, Rob Walling breaks down the 10 decisions that shaped his success, like choosing action over perfection, learning fast from failure, and building a financial cushion to take smarter risks. It’s an honest look at what worked and the choices that made the biggest difference.

Topics we cover: 

• (2:53) – Stop reading, start shipping
• (4:48) – Learn from mistakes and change course
• (6:47) – Build a financial cushion
• (8:38) – Write publicly about your journey
• (13:04) – Make bigger, but manageable bets
• (15:21) – Embrace the unsexy, grindy work
• (18:05) – Identify blind spots to grow faster
• (19:39) – Set clear goals and stick to them
• (21:26) – Know when to persist, pivot, or quit
• (24:40) – Don’t make decisions in emotional moments

Links from the Show: 

• MicroConf Connect
• Start Small, Stay Small
• Comic Lab Podcast 
• TinySeed Institute

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling walks through his ‘founder regret list’, detailing 12 key mistakes from his 20-year entrepreneurial journey. In this very personal episode, he tells some stories he’s never shared publicly before.

Topics we cover: 

• (4:17) – Thinking venture capital was the only path
• (6:12) – Launching without validating the idea
• (9:26) – Choosing ideas that couldn’t be bootstrapped
• (12:48) – Relying too much on books
• (16:36) – Trying to do everything solo
• (21:10) – The arrival fallacy
• (23:19) – Delaying email list growth
• (25:51) – Taking random advice too seriously
• (28:43) – Overestimating skills after early wins
• (30:29) – Letting anxiety steal the joy from success
• (32:34) – Not letting wins build confidence
• (33:50) – Holding onto a scarcity mindset

Links from the Show: 

• TinySeed Institute
• Sponsor the Podcast or MicroConf
• Start Small, Stay Small
• The SaaS Playbook
• Zero to Sold by Arvid Kahl

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling welcomes back fan favorite Ruben Gamez, founder of SignWell, to debunk common bootstrapper myths. They discuss misconceptions like never needing to sell your company or market your product, and emphasize the realities of growth plateaus, business valuation, and exit strategies.

Topics we cover: 

• (4:50) – I’ll never sell my company
• (11:40) – I can just coast on profit forever
• (21:48) – I’m built differently, so I don’t need to market
• (31:54) – Building many tiny projects is a strategy
• (34:46) – It’s all about luck

Links from the Show: 

• Invest in TinySeed Fund 3
• Ruben Gamez (@earthlingworks) | X
• SignWell
• Ruben Gamez | LinkedIn
• MicroConf YouTube Channel

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling sits down with SaaS growth expert (and TinySeed Institute coach) Marc Thomas to break down ten persistent and damaging myths believed by many SaaS founders and why challenging them is key to scaling smart.

Topics we cover: 

• (4:52) – “I’m not good at marketing” is a lie
• (8:48) – Top-of-funnel obsession
• (13:12) – Lifetime affiliate payouts = profit killers
• (18:21) – Hiring a marketing team too soon
• (21:52) – Chasing new markets too early
• (25:08) – Fear of sending more email
• (27:36) – Chasing shiny growth hacks like programmatic SEO
• (31:14) – Dismissing sales in favor of only self-serve
• (35:10) – Avoiding competitor content out of fear

Links from the Show: 

• MicroConf Europe – September 28–30 · Istanbul, Türkiye
• TinySeed SaaS Institute
• Positive Human
• Marc Thomas | LinkedIn
• Marc Thomas’ LinkedIn post on 10 SaaS Myths

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling answers listener questions about pricing pilots, choosing niches, and skipping steps on his Stair Step Method of Bootstrapping.  Want to get your question answered? Drop them here.

Topics we cover: 

• (3:25) – Feedback on Season 4 of TinySeed Tales
• (8:55) – How do you price pilot projects?
• (15:11) – How to niche down and de-risking a new SaaS?
• (22:40) – What does it really take to build a hit open-source tool?
• (29:53) – Can you skip straight to SaaS or is that a trap?

Links from the Show: 

• MicroConf Connect: Online community of SaaS founders
• TinySeed Tales Podcast
• Startup Stories Podcast
• Stair Step Method of Bootstrapping

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest, to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring and how shifting toward purpose-driven work can create more freedom, meaning, and longevity.

Topics we cover: 

• (2:17) – Why traditional retirement often leads to boredom and regret
• (6:44) – How working longer can drastically reduce your savings burden
• (11:05) – The power of $50K moments and appreciating time with loved ones
• (17:03) – Prioritizing health and well-being as a long-term strategy
• (21:42) – Smarter and more flexible alternatives to full retirement

Links from the Show: 

• MicroConf Europe – September 28–30 · Istanbul, Türkiye
• TinySeed – Invest
• Let’s Retire Retirement – Book on Amazon
• Derek Coburn’s Website
• Derek Coburn | LinkedIn
• Derek Coburn (@cadredc) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Kevin Wagstaff joins Rob Walling to share how he and his brother bootstrapped Spectora from a scrappy MVP to a $90M valuation. It’s a masterclass in finding traction in unsexy markets, building with empathy, and making smart bets like embedded payments.

Topics we cover: 

• (4:39) – The surreal moment Kevin and his brother became multimillionaires
• (9:14) – Why a mobile-first approach won in an outdated, overlooked niche
• (17:39) – How adding payments created a second revenue stream and bigger valuation
• (20:36) – The early hustle: trade shows, 6 AM demos, and Facebook group tactics

Links from the Show: 

• SaaS Launchpad Course
• MicroConf
• Kevin Wagstaff | LinkedIn
• Kevin Wagstaff (@KevinWagstaff3) | X
• Spectora
• Kevin’s Built to Sell Radio Episode

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode, Rob Walling and fan favorite Derrick Reimer delve into listener questions about startup development. They discuss the impact of AI coding tools on building minimum viable products (MVPs) and the importance of user experience (UX) with advice on balancing UX investment based on the product's nature. 

You’ll also hear a breakdown of the real costs of leaving the cloud, plus tips on email deliverability and validation. Throughout, they highlight how validating ideas through user feedback and research is still critical, no matter how fast you build.

Episode Sponsor:

This podcast is brought to you by Mercury. I've been banking with Mercury for years and whenever I set up a new account, I'm reminded why traditional banking feels stuck in the past. 

When our previous bank faced solvency issues, we needed to spin up new accounts quickly that could handle millions in funds across multiple businesses. Mercury had us up and running almost immediately.

I manage half a dozen different Mercury accounts across a wide range of companies – from my personal, single-member LLC to MicroConf, our 7-figure global events and education platform, to TinySeed, our venture fund and accelerator. Mercury easily handles them all.

The interface is elegantly simple for daily banking, paying invoices, and sending and receiving international wires, yet powerful enough to handle the multi-step approval processes we needed to put in place when funding founders with large transfers. 

Anytime founders ask me who they should set up their accounts with, I send them to mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

Topics we cover: 

• (4:55) – How AI coding tools are changing the MVP timeline
• (16:11) – When UX design actually matters (and when it doesn’t)
• (23:47) – Should you ditch cloud hosting for your own servers?
• (32:38) – Pro tips on email deliverability and keeping out of spam folders

Links from the Show: 

• SaaS Launchpad Course
• MicroConf Remote | May 21, 2025
• Windsurf AI Editor
• SavvyCal
• Derrick Reimer | LinkedIn
• Derrick Reimer (@derrickreimer) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (3:26) – Spotting the gap in affiliate tools for creators
• (7:09) – The agency MVP failure and early dev misfires
• (11:15) – Losing a CTO to priesthood 
• (16:33) – How influencer partnerships fueled fast early growth
• (30:12) – Hiring a world-class CTO and engineering team

Links from the Show: 

• Discretion Capital
• MicroConf Remote | May 21, 2025
• TinySeed
• Noah Tucker | LinkedIn
• Noah Tucker (@noatuck) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Episode Sponsor:

This podcast is brought to you by Mercury. I've been banking with Mercury for years and whenever I set up a new account, I'm reminded why traditional banking feels stuck in the past. 

When our previous bank faced solvency issues, we needed to spin up new accounts quickly that could handle millions in funds across multiple businesses. Mercury had us up and running almost immediately.

I manage half a dozen different Mercury accounts across a wide range of companies – from my personal, single-member LLC to MicroConf, our 7-figure global events and education platform, to TinySeed, our venture fund and accelerator. Mercury easily handles them all.

The interface is elegantly simple for daily banking, paying invoices, and sending and receiving international wires, yet powerful enough to handle the multi-step approval processes we needed to put in place when funding founders with large transfers. 

Anytime founders ask me who they should set up their accounts with, I send them to mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

Topics we cover: 

• (3:02) – What Go-to-Market actually means for bootstrapped founders
• (7:14) – Early Customer Profile (ECP) vs. Ideal Customer Profile (ICP)
• (10:30) – Common mistakes founders make when choosing their ECP
• (13:48) – Real-world B2B SaaS examples of successful ECP launches
• (18:29) – Why GTM actions must come before GTM motions for scrappy startups
• (21:52) – Warm outreach and fishing in the right forums: practical tactics for early traction

Links from the Show: 

• MicroConf Growth Retreat | London, UK - May 14-16, 2025
• Invest in TinySeed
• Maja Voje | LinkedIn
• GTM Strategist
• Go-To-Market Strategist: (Maja's book)

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 772, Rob Walling talks with Anthony Pierri of Fletch about a proven approach to product positioning. They discuss key lessons from 400+ startups, focusing on workflows, competitive alternatives, and why narrowing your audience matters.

Topics we cover: 

• (6:59)  – What is positioning, really?
• (11:16)  – Why your homepage matters more than your pitch deck
• (14:17) – Workflow-based segmentation vs. firmographics
• (17:39) – Positioning against competitive alternatives
• (31:13) – The #1 mistake founders make with positioning

Links from the Show:

• MicroConf Growth Retreat | London, UK - May 14-16, 2025
• Invest in TinySeed
• Get Access to Anthony’s MicroConf New Orleans Talk
• Anthony Pierri (@anthonypierri) | LinkedIn
• Anthony Pierri (@apierriPMM) | X
• Fletch

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 771, Rob Walling is joined by Craig Hewitt to answer listener questions. They discuss the changes that happen while transitioning from a small startup to a multi-million dollar SaaS, competing against larger competitors, and maintaining startup culture as teams grow. They also share thoughts on AI agents in the SaaS space and the relevance of patents for bootstrapped businesses.

Episode Sponsor:

This podcast is brought to you by Mercury. I've been banking with Mercury for years and whenever I set up a new account, I'm reminded why traditional banking feels stuck in the past. 

When our previous bank faced solvency issues, we needed to spin up new accounts quickly that could handle millions in funds across multiple businesses. Mercury had us up and running almost immediately.

I manage half a dozen different Mercury accounts across a wide range of companies – from my personal, single-member LLC to MicroConf, our 7-figure global events and education platform, to TinySeed, our venture fund and accelerator. Mercury easily handles them all.

The interface is elegantly simple for daily banking, paying invoices, and sending and receiving international wires, yet powerful enough to handle the multi-step approval processes we needed to put in place when funding founders with large transfers. 

Anytime founders ask me who they should set up their accounts with, I send them to mercury.com.

Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

Topics we cover: 

• (2:41) – Marketing and sales strategies while scaling
• (9:31) – Keeping the startup culture through growth
• (14:50) – Can SaaS survive autonomous agents?
• (21:03) – AI wrapper tools
• (25:15) – Patent strategy for startups
• (29:30) – Competing against VC-backed companies

Links from the Show: 

• MicroConf Remote: Early-Stage SaaS Sales
• Invest in TinySeed
• Craig Hewitt (@TheCraigHewitt) | X
• Craig Hewitt (@craighewitt.com) | Bluesky
• Rouge Startups
• Castos
• Omar Zenhom
• Omar Zenhom’s MicroConf Talk
• AI Agents vs SaaS - Who Wins the Future of Software?
• Episode 542 | 10x in Two Years, Past $3M ARR with SquadCast

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your quest...

In episode 770, Rob Walling goes solo to explore the relationship between revenue and profit in SaaS, and the dangers of waiting for permission. He also draws inspiration from Mike Tyson’s work ethic and George Lucas’ visionary mindset to encourage entrepreneurs to push through obstacles and innovate.

Topics we cover: 

• (2:41) – MRR versus ARR
• (8:04) – Don’t ask for permission, don’t give in to defeatism
• (14:38) – Inventing to pursue novel visions
• (18:48) – Mike Tyson’s training regimen 
• (20:48) – You don’t need to be the best in the world

Links from the Show: 

• MicroConf Growth Retreat
• Discretion Capital
• Email Einar
• Rob Walling (@robwalling) | X
• Rob Walling | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 769, Rob Walling welcomes Derrick Reimer back to share highlights from MicroConf New Orleans. They dive into the event's vibrant atmosphere, standout founder talks, and the energizing mix of new and familiar faces that made this gathering in the Big Easy truly special.

Topics we cover: 

• (1:40) – MicroConf New Orleans audience breakdown
• (5:50) – Upcoming MicroConf events
• (9:05) – 5 Lessons That Exits Teach Us About Running Our Business
• (12:35) – Anthony Pierri’s talk about homepage positioning
• (15:16) – 4 New Orleans excursions
• (17:17) – Talks on copywriting, pricing, and LinkedIn outreach
• (25:57) – Reviewing attendee feedback

Links from the Show: 

• MicroConf Connect Applications Open Until April 9th
• MicroConf Growth Retreat
• MicroConf Europe 2025
• MicroConf Remote
• Exit Strategy by Sherry Walling, PhD & Rob Walling
• Derrick Reimer (@derrickreimer) | X
• Derrick Reimer(@derrickreimer.com) | Bluesky
• SavvyCal
• Episode 737 | Key Takeaways from MicroConf Europe 2024 (With Derrick Reimer)
• Anthony Pierri (@apierriPMM) | X
• Lianna Patch (@punchlinecopy.com) | Bluesky
• Street Pricing by Marcos Rivera
• Episode 765 | TinySeed Tales s4e9: Making the hardest decision

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 768, Rob Walling unpacks a series of semi-controversial beliefs about bootstrapping from ScrapingBee’s Pierre de Wulf. Rob evaluates each point from Pierre's tweet, discussing topics like rebranding your SaaS, the hidden problem of affiliate marketing, and the realities of scaling a SaaS business.

Topics we cover: 

• (1:21) – Pierre’s semi-controversial bootstrapping beliefs 
• (4:35) – Don’t waste time on a rebrand
• (7:24) – No one cares about your domain extension   
• (9:06) – Affiliate marketing won’t fix your acquisition issues
• (11:51) – There is no silver bullet for growth
• (13:42) – Copy what works best
• (14:59) – Double down on acquisition channels that work
• (16:53) – Hire specialists
• (19:34) – Never offer a plan with unlimited features
• (20:22) – Don’t offer a cheap plan if you can’t support it
• (20:47) – Don’t add social logins to your signup page
• (21:27) – Read competitors’ reviews several times a year
• (21:59) – $10k MRR doesn’t guarantee $100k MRR
• (22:28) – You will get copied if you share success
• (23:02) – “Build this feature…”
• (24:10) – The Mom Test
• (24:56) – Provide value for your target demographic for free
• (25:47) – Don’t overthink Product Hunt
• (26:00) – You’ll never sell your SaaS for 10x

Links from the Show: 

• MicroConf Growth Retreat in London
• Rob Walling (@robwalling) | X
• Pierre de Wulf (@PierreDeWulf) | X
• ScrapingBee (@ScrapingBee) | X
• ScrapingBee
• Pierre’s semi-controversial bootstrapping beliefs
• TinySeed
• Rob Walling.com
• Rob Walling | LinkedIn
• SaaS Institute
• Exit Strategy by Sherry Walling, PhD & Rob Walling
• Episode 705 | From Bootstrapped to Mostly Bootstrapped to Venture Backed
• The Mom Test by Rob Fitzpatrick
• Deploy Empathy by Michele Hansen
• The SaaS Playbook by Rob Walling

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your questi...

In episode 767, Rob Walling is joined again by Brendan Fortune to answer listener questions focused on product management. They discuss identifying your ideal customer profile, prioritizing feature requests, and positioning against competitors. They also weigh in on how product managers should focus their time.

Topics we cover: 

• (2:50) – Is your ideal customer always your highest paying one?
• (8:11) – Finding just one ICP can be difficult
• (14:56) – How do you prioritize feature requests?
• (19:24) – Product management is art and science
• (26:02) – Competing with competitors on value, not price
• (32:21) – How should product managers focus their time?
• (37:20) – How do PMs manage roadmaps and user feedback?

Links from the Show: 

• Invest in TinySeed
• MicroConf Mastermind Applications close March 31st
• MicroConf Growth Retreat
• The SaaS Playbook
• Brendan Fortune | LinkedIn
• Customer.io
• Episode 756 | Why Great Product Management Is Critical for Your Startup
• Product Flywheel + Pricing + Org Strategy (Miro)
• Savio

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 766, Rob chats with Steli Efti about growing Close.com to over $40 million in ARR. Steli shares insights into the importance of maintaining strong co-founder relationships over 12 years, navigating crises, and the importance of emotional resilience in entrepreneurship. They also dive into Close's recent pricing shift to introduce a lower entry-level plan.

Topics we cover: 

• (2:08) – Reflecting on 12 years of SaaS at Close
• (3:50) – Strong co-founder relationships
• (11:24) – Longevity and consistently showing up
• (20:23) – Surviving moments of crisis
• (29:27) – Launching a more affordable pricing tier
• (34:40) – Getting back into the content game

Links from the Show: 

• Exit Strategy by Sherry Walling, PhD & Rob Walling
• Close
• Close Sales Guides
• Episode 498 | Selling During a Pandemic with Steli Efti
• The 0 to $30 Million Blueprint
• Steli Efti (@Steli) | X
• Steli Efti | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this season finale of TinySeed Tales, Rob Walling sits down with Colleen Schnettler, founder of Hello Query, to reflect on her journey over the past few years.

Colleen candidly shares the challenges she faced while trying to grow her SaaS business, including the difficult decision to shut it down after struggling to find traction. Moving past a painful part in her founder journey, Colleen is excited about her new venture where she’s already seeing early success. Join us for this honest look into the final days of Hello Query and to hear Colleen's resilience in the startup world.

Topics we cover: 

• (1:07) – Difficulty in finding and onboarding customers
• (5:32) – Why didn’t it work? 
• (9:29) – How did the co-founder split affect the business?
• (13:11) – Founder regrets
• (18:49) – Reflecting on the decision
• (22:38) – Anything that you would have done differently?
• (25:21) – Moving forward to founder coaching and marketing

Links from the Show: 

• Join the TinySeed Mailing List
• Apply for TinySeed
• SaaS Marketing Gym
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Hello Query
• The Score Takes Care of Itself by Bill Walsh

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 764, Rob Walling interviews Jordan Gal, co-founder of Rosie, to learn about how he pivoted from Rally to build an AI-driven product for small business owners. Jordan shares insights into the challenges of finding product-market fit, the importance of trial and error, and the rapid growth Rosie has experienced since its launch. They delve into the significance of effective onboarding, and how building an MVP changes in the face of AI. 

Topics we cover: 

• (2:38) – From CartHook to Rally to Rosie
• (6:28) – Deciding to pivot and feeling product-market fit
• (12:55) – Coming up with a feature set
• (16:50) – Building an MVP quickly
• (19:29) – Competition when developing with AI 
• (24:52) – Removing features and flexibility in software
• (29:59) – Incredibly fast onboarding
• (33:22) – Balancing a “better business” with a “faster business”

Links from the Show: 

• Applications for MicroConf Mastermind Matching are Open through March 31st
• SaaS Institute
• Rosie
• Jordan Gal (@JordanGal) | X
• Rosie (@heyrosieai) | X
• Episode 549 | Hiring vs. Outsourcing, E-commerce SaaS, and More Listener Questions with Jordan Gal

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hello Query, as she tries to achieve product-market fit on a deadline.

Colleen reveals the struggles of cold outreach and the overwhelming data landscape while testing a potential solution. With a clearer vision and two paying customers, she reflects on the importance of defining her value proposition, and the critical timeline she has set for herself to gain traction before her runway ends.

Topics we cover: 

• (1:43) – Debating becoming a data aggregator 
• (6:30) – Finding a new direction
• (8:21) – Running out of runway
• (10:39) – When is it time to quit?

Links from the Show: 

• The SaaS Launchpad
• Quit by Annie Duke
• TinySeed
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Hello Query

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In episode 762, join Rob Walling for a solo adventure where he covers several topics. Rob breaks down Paul Graham's essay, "Doing Great Work" and focuses on how the steps apply to building real businesses for real customers. He also discusses the hierarchy of skills necessary for success in the SaaS space, sharing his thoughts on the critical roles of marketing, product development, engineering, and effective team management.

Topics we cover: 

• (2:07) Doing great work
• (5:20) Identify the gaps
• (11:51) The SaaS skillset hierarchy
• (18:28) Publicly committing to a feature release
• (23:05) Maintaining enough rigor to hit deadlines

Links from the Show: 

• MicroConf Connect Applications are open now through March 5th
• How to Do Great Work by Paul Graham
• Start Small Stay Small by Rob Walling
• Episode 756 | Why Great Product Management Is Critical for Your Startup

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Colleen, now solo, navigates the challenge of refining her product vision. After a period of introspection, Colleen shares her decision to pivot from targeting engineering managers to focusing on marketing data analysts. She discusses the insights gained from hiring a marketing coach and the excitement of landing her first paying customer, despite some critical feedback on her product's UI.

Topics we cover: 

• (1:50) – Early product excitement fizzles out
• (5:14) – When is it time to move on from an idea?
• (8:57) – Helping marketers build better reports
• (13:03) – Setting early pricing
• (14:02) – Determining how much to polish an MVP
• (17:36) – Predicting what’s ahead

Links from the Show: 

• SaaS Institute
• TinySeed
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Hello Query

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (2:30) – Considerations when white-labeling within your SaaS
• (9:03) – Does relying on other SaaS affect our valuation?
• (10:10) – Tools for tracking SaaS metrics to enable scaling
• (17:03) – Do founder mindsets change at MRR milestones?
• (21:34) – Mistakes founders make in their mindset
• (25:27) – Forcing an onboarding step
• (27:29) – Determining team composition

Links from the Show: 

• The SaaS Launchpad
• The SaaS Playbook
• Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
• Invest in TinySeed
• Episode 685 | 7 Things You Should Never Do (A Rob Solo Adventure)
• Episode 722 | Bootstrapping a Vertical SaaS to 7-Figures in 18 Months

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

After reigniting her “shipping muscle” while briefly dabbling in an AI-based project, Colleen refocuses on her newest pivot of Hello Query. She shares the challenges of determining the market viability of an AI-assisted SQL report builder. She stands at a crossroads, torn between catering to internal BI teams or exploring marketing analytics.

Topics we cover: 

• (1:25) – Reflecting on the co-founder breakup
• (2:42) – Trying a scratch-your-own-itch project
• (6:27) – Unfair advantages inform another pivot
• (15:07) – Respecting the “emotional runway”  
• (19:23) – Marketing insights vs. an internal BI tool
• (23:01) – The curse of the audience

Links from the Show: 

• Applications for TinySeed are Open Through Feb 23rd
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Hello Query

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Episode Sponsor:

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But Corey Haines and the team at Conversion Factory? They know how to deliver results. 

Derrick Reimer said that "Under Corey's marketing leadership, SavvyCal broke into the market with a successful launch and steadily grew to several thousand customers."

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Topics we cover: 

• (1:18) – How to launch a SaaS product in a market with an established competitor
• (6:21) – Do I call out competitors by name?
• (14:24) – How do you really identify what moves the needle in your Saas?
• (19:59) – Breaking down the “one thing”
• (23:32) – Selling and marketing SaaS before building
• (30:36) – What is the goal of your free trial?
• (39:10) – On the fence between B2B, B2C

Links from the Show: 

• TInySeed Applications are open until Feb 23rd
• Derrick Reimer (@derrickreimer) | X
• Derrick Reimer (@derrickreimer.com) | Bluesky
• SavvyCal
• 757 | TinySeed Tales s4e5: Founder Breakups, Crushing Failures, and the Future
• TinySeed
• MicroConf Connect
• SaaS Institute
• Start Marketing The Day You Start Coding by Rob Walling
• Start Small Stay Small by Rob Walling

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes |

After a challenging period with her co-founder Aaron, Colleen reflects on their decision to part ways and the emotional toll it has taken on her. She shares her feelings of crushing failure, the uncertainty of moving forward alone, and the realization that their initial product vision may not align with market needs. 

Topics we cover: 

• (0:49) – Colleen and Aaron make a tough decision
• (4:09) – Voice memo, “Crushing Failure”
• (7:59) – What if you hadn’t raised money?
• (11:44)  – Colleen weighs her remaining options

Links from the Show: 

• Applications for TinySeed are Open Through Feb 23rd
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Hello Query

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (2:46) – What does a product manager do?
• (10:36) – When should a SaaS company designate a full time product manager?
• (15:33) – Pricing and and creating a flywheel
• (22:41) – Deciding on your “fair” value metric
• (30:01) – Pricing experimentation in the early days

Links from the Show: 

• Applications for TinySeed Spring 2025 are Open!
• Invest in TinySeed
• Ask a product question on Startups For the Rest of Us
• Brendan Fortune | LinkedIn
• Customer.io
• Product Flywheel + Pricing + Org Strategy (Miro)
• Your Pricing is WRONG (even Sam Altman Made This Mistake)

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Colleen shares the insights gained from recent customer interviews that led to a significant pivot in their product strategy. Hello Query is now focused on embedding custom reporting features within other SaaS applications and Colleen reflects on balancing product quality with minimal v1 features. Her excitement is building to get their solution into users' hands.

Topics we cover: 

• (1:32) – Digging into customer interviews
• (3:54) – Filtering out the noise to achieve confidence
• (5:31) – Other competitors in the space
• (8:53) – How Colleen prepares for and sources customer conversations
• (12:11) – Is the technical implementation coming along?

Links from the Show: 

• Invest in TinySeed
• Episode 748 | The Ins and Outs of Startup Investing
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Hello Query

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (3:12) – When in doubt, don’t try freemium
• (6:44) – Different levers you can pull to make freemium work
• (8:53) – How will SaaS be affected by the exponential growth of AI?
• (14:09) – Big players launching features is a form of platform risk
• (17:24) – Should I spin out a portion of my product into a new product?
• (20:05) – Thinking through plateaus in your business growth

Links from the Show: 

• MicroConf Connect Applications are open through Feb 5th
• Ask a Question on Startups For the Rest of Us
• TinySeed
• Episode 663 | 5 Insights SaaS Founders Should Know About A.I. (Ignore at Your Peril)
• Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
• MicroConf YouTube Channel

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Colleen opens up about the emotional challenges of co-founder conflicts with Aaron, highlighting the importance of communication and alignment in their partnership. They also discuss the significant pivot from their initial product offering to the newly rebranded Hello Query, a SaaS solution focused on internal reporting for teams.

Topics we cover: 

• (0:59) – Breaking up with a co-founder
• (7:39) – How could this conversation have been different?
• (9:49) – Navigating a major pivot
• (14:37) – Changing the name
• (16:56) – Getting closer to finding product-market-fit
• (19:39) – Competing in a competitive market

Links from the Show: 

• SaaS Institute
• TinySeed
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Aaron Francis (@aarondfrancis) | X
• Aaron Francis (@aaronfrancis.com) | Bluesky
• MicroConf Recap, Episode 59 – The Hammerstone Podcast
• Hello Query

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (2:16) – SEO traffic that generates $7.2M annual revenue
• (4:54) – Changes in Google’s algorithm
• (9:46) – How to approach SEO as a bootstrapper
• (15:45) – SEO has changed considerably
• (19:48) – AI and SEO
• (25:54) – The advent of AI Overviews
• (31:19) – Parasite SEO and the importance of brands

Links from the Show: 

• Get Your Tickets for MicroConf US by Jan 31st
• Larslofgren.com
• Lars Lofgren (@LarsLofgren) | X
• Lars Lofgren at MicroConf
• TinySeed.com
• MicroConf YouTube Channel

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Colleen describes the tough decision to focus on one product stack, and their recent pivot toward building a reporting MVP. They also discuss Colleen’s shift into a more managerial role.

Topics we cover: 

• (2:10) – Motivations behind building additional functionality
• (7:07) – Repositioning the reporting dashboard
• (10:08) – Focusing in on the successful part of the product
• (14:30) – How shifting focus affects the team dynamic
• (16:19) – ”Hiring is horrible”
• (22:20) – What has management been like?
• (26:11) – Growing as a manager

Links from the Show: 

• Invest with TinySeed
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Refine by Hammerstone
• Hello Query
• Buy Back Your Time by Dan Martell 
• Never Split the Difference by Chris Voss, Tahl Raz

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (3:14) – Building a team before you can afford your first, full time hire
• (11:11) – Testing pricing with existing customer bases
• (19:00) – What type of content should you focus on?
• (25:20) – Growing a pipeline of leads with limited resources
• (31:00) – Who are your 100 best customers?

Links from the Show: 

• SaaS Institute
• TinySeed
• TinySeed Tales is Back: S4E1
• Lauraroeder.com
• Laura Roeder (@lauraroeder.bsky.social) | Bluesky
• Paperbell
• Episode 473 | Managing Annual Subscriptions, Low-price vs. High, Being a Non-Developer Founder, and More Listener Questions with Laura Roeder
• Exactly How I Cold Emailed My Way to A Life-Changing Exit (And You Can Too) by Laura Roeder
• The SaaS Playbook
• Buy Back Your Time by Dan Martell
• If I Started SaaS in 2024, Here’s My B2B Content Strategy for $1M ARR
• The Ultimate Sales Machine by Chet Holmes

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

In the first episode of Season 4, Rob introduces us to Colleen Schnettler, the cofounder of Hammerstone. Colleen is a self-taught Rails developer, and this season will follow how Hammerstone eventually becomes Hello Query – an AI-powered chatbot that runs custom reporting on your data. Colleen is one of 27 startup founders from TinySeed’s Fall 2022 accelerator batch.

Topics we cover: 

• (2:16) – TinySeed Tales Season 4 with Colleen Schnettler
• (3:57) – Custom reporting in Laravel and Rails
• (7:05) – Becoming an “atypical founder”
• (14:11) – Entrepreneurship as a military spouse
• (16:17) – Motivations for joining TinySeed
• (19:15) – A recent low point, and high point in the business
• (25:00) – Big plans and risky moves ahead

Links from the Show: 

• TinySeed Applications open on February 10th
• Colleen Schnettler (@leenyburger) | X
• Colleen Schnettler (@leenyburger.bsky.social) | Bluesky
• Refine by Hammerstone
• Hello Query
• Software Social Podcast
• TinySeed Tales | Season 1 | Castos
• TinySeed Tales | Season 2 | Gather
• TinySeed Tales | Season 3 | Cloudforecast

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (2:37) – The stigma of bootstrapper funding is waning
• (6:44) – What success looks like in venture funding
• (10:45) – Breaking down the math and deal flow
• (17:54) – How valuations work
• (26:21) – Keeping optionality
• (29:58) – Evaluating markups
• (35:18) – Raising TinySeed’s next fund

Links from the Show: 

• MicroConf Connect Applications open until January 15th
• TinySeed
• Invest with TinySeed
• Einar Vollset (@einarvollset) | X
• Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics
• Discretion Capital
• How To Invest In Startups by Sam Altman

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (2:20) – How customer success works at Userlist
• (5:27) – Dealing with upfront onboarding friction 
• (9:51) – Stage 1, “young and naive”
• (12:16) – Stage 2, “hire someone”
• (19:06) – Stage 3, “done for you services”
• (25:47) – Leveraging the Userlist blog
• (29:26) – Stage 4, “developing your own frameworks”

Links from the Show: 

• SaaS Institute
• TinySeed
• Jane Portman (@uibreakfast) | X
• Jane Portman (@uibreakfast.com) | Bluesky
• Userlist
• Episode 471 | Fighting to Gain Traction in a Crowded Space with Jane Portman of Userlist
• Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure)
• Crossing the Chasm by Geoffrey A. Moore
• Userlist Closes a Pre-Seed Round with 21 Angel Investors
• SaaS Email Marketing Strategy: Everything You Need to Know
• 20+ “Invite Your Team” Email Examples
• Atomic Emails: Our Proven Method for Writing Email Campaigns

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (1:52) – Carrying forward predictions from 2024
• (3:09) – Search volume for Google organic SEO 
• (6:34) – Ads in AI interfaces
• (7:50) – Google’s revenue drops, bootstrapper opportunities
• (10:07) – “AI” use in  H1’s 
• (14:01) – Self-driving taxis
• (19:28) – Platform risk intensifies

Links from the Show: 

• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• Episode 697 | 7 Predictions for SaaS Bootstrappers in 2024
• Episode 725 | SEO in the Age of AI, Freemium, When Brand Becomes Important, and More Advanced Listener Questions (with Ruben Gamez)
• LINKLO
• TinySeed
• Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• (2:05) – Looking back at concepts and frameworks from past 12 months
• (8:50) – Rob’s 5 favorite episodes
• (11:56) – Reflecting on 2024 accomplishments
• (19:47) – TinySeed Tales Returns in 2025
• (21:18) – Evaluating 2024 predictions

Links from the Show: 

• The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea”
• MicroConf YouTube Channel
• Episode 706 | 2/20/200 Validation, Prior Art, and Designing by Committee (A Rob Solo Adventure)
• TinySeed
• Vertical SaaS vs Horizontal SaaS - Which is More Profitable?
• Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
• The SaaS Playbook
• Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
• Episode 706.5 | Rethinking My Most Common Advice
• Episode 729 | 9 Things I’ve Learned Investing in 170+ SaaS Companies
• Episode 709 | The 7 Greatest Investments of My Life
• Episode 694 | 2023 In Review: Amazing Growth & Fighting Burnout
• How Ben Chestnut Bootstrapped Mailchimp to a $12 Billion Exit
• MicroConf New Orleans 2025
• Start Small, Stay Small by Rob Walling
• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• TinySeed Tales

Topics we cover: 

• (1:49) – Will Bluesky survive and thrive?
• (9:07) – The bet on Bluesky growth
• (13:46) – TinySeed is raising a third fund
• (17:25) – Y Combinator backs duplicates
• (22:18) – Dealing with Imposter Syndrome
• (27:46) – Australia's social media ban

Links from the Show: 

• The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea”
• Invest in TinySeed
• Rob Walling (@robwalling.com) | Bluesky
• TinySeed (@tinyseed.com) | Bluesky
• Tracy Osborn (tracymakes) (@tracyosborn.com) | Bluesky
• Einar Vollset (@einarvollset) | X
• Y Combinator often backs startups that duplicate other YC companies, data shows
• Procrastination and the Fear of Not Being 'Good Enough' by Swapnil Chauhan
• Startup Founders, Do THIS to Beat Imposter Syndrome
• Australia proposes 'world-leading' ban on social media for children under 16

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Back the book on Kickstarter

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io. 

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.” 

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer. 

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. 

Topics we cover: 

• (1:49) – Exit Strategy Introduction
• (6:56) – Exits are complicated
• (11:16) – One of the hardest things you’ll ever do
• (15:57) – Your business is your baby 
• (18:35) – Entering the unknown
• (26:49) – Six factors that shape how you feel about an exit
• (31:03) – Making it real

Links from the Show: 

• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• Back the book on Kickstarter
• MicroConf Connect Applications Close Today, December 10th
• Rob Walling (@robwalling) | X
• Dr. Sherry Walling (@sherrywalling) | X
• The SaaS Playbook
• Built to Sell by John Warrillow
• Touching Two Worlds by Dr. Sherry Walling
• The Entrepreneur’s Guide to Keeping Your Sh*t Together by Sherry Walling, PhD, Rob Walling

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your quest...

Exit Strategy Kickstarter ends on December 12!

Topics we cover: 

• (2:39) – Normalizing doing hard things
• (6:54) – The “hard things” in your startup
• (10:27) – Walking into the storm
• (16:21) – ”Make it work, make it right, make it fast”
• (22:04) – Building your “Founder Gut”
• (25:42) – Think in years, not months

Links from the Show: 

• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• MicroConf Masterminds Applications Close on December 4th
• Rob Walling (@robwalling) | X
• Dr. Sherry Walling (@sherrywalling) | X
• The Comic Lab Podcast
• The SaaS Playbook
• The Stair Step Method of Bootstrapping
• This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io. 

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.” 

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer. 

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. 

Topics we cover: 

• (2:01) – Defining product-led growth
• (6:07) – Are users able to get value for free? 
• (11:38) – Hybrid: both product-led and sales-led
• (14:52) – Determining the main outcome of your free model
• (19:23) – Misuse of the PLG terminology
• (22:00) – The benefits of PLG over sales-led growth
• (24:08) – Workshopping SavvyCal’s product-led strategy

Links from the Show: 

• Mastermind Applications are open until December 4th
• Wes Bush (@wes_bush) | X
• ProductLed (@productled) | X
• ProductLed
• Product-Led Growth: How to Build a Product That Sells Itself by Wes Bush
• The Product-Led Playbook: How to Unlock Self-Serve Revenue and Dominate Your Market (With a Tiny Team) by Wes Bush
• Free Audiobook of The Product-Led Playbook
• Product-Led Onboarding by Ramli John
• TinySeed
• SparkToro
• SavvyCal

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Exit Strategy is now live on Kickstarter!

Topics we cover: 

• 2:01 – Not just a book for those selling SaaS
• 8:13 – The Kickstarter for the book is live today
• 12:16 – Before, during, and after the exit
• 14:55 – Why exiting is so hard
• 20:39 – Life after the exit
• 25:10 – A few traps await founders shortly after exit
• 26:24 – What do you do with a big pile of money?

Links from the Show: 

• MicroConf Remote Goes Live November 20th!
• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• Rob Walling (@robwalling) | X
• Dr. Sherry Walling (@sherrywalling) | X
• Zen Founder
• Zen Founder Podcast
• The SaaS Playbook
• The Art of Selling Your Business by John Warrillow
• Before the Exit by Dan Andrews 
• Finish Big by Bo Burlingham
• MicroConf
• TinySeed
• Touching Two Worlds by Dr. Sherry Walling

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io. 

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.” 

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer. 

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. 

Topics we cover: 

• 3:13 – Go links, URL shorteners for enterprise
• 6:14 – History of the problem and core users
• 9:44 – Customer education and growth opportunities
• 15:37 – Finding the repeatable marketing funnel
• 21:07 – Buying into a co-founder role at Trotto
• 24:42 – What’s the hardest part of running Trotto?

Links from the Show: 

• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• MicroConf Masterminds - Applications close on December 4th, 2024
• Trot.to
• Trotto go links (@TrottoHQ) | X
• TinySeed
• How did go links start and evolve at Google?
• Quiet Light

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

Topics we cover: 

• 1:58 – Expanding to enterprise deals after product-market fit
• 6:39 – Word of mouth marketing is tricky for B2B SaaS
• 14:36 – Educating the market as a bootstrapper
• 20:07 – Selling integrations through incubators and accelerators
• 24:38 – Developing a profit sharing model

Links from the Show: 

• Register for MicroConf Remote before Nov. 7th for Early Bird pricing & extras
• Ask a Question at Startups For the Rest of Us
• The SaaS Playbook
• TinySeed
• Adjacency Matrix: How to expand after PMF by Jason Cohen
• F5Bot
• Syften
• Podscan
• Veed
• Devising a profit sharing program for micro-multinationals by Peldi Guilizzoni

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

If you missed the event and had some MicroConf FOMO, get your tickets now for our New Orleans event!

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io. 

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.” 

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer. 

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. 

Topics we cover: 

• 2:47 – MicroConf Europe vs. MicroConf US
• 6:44 – Adding “excursions” to the programming
• 11:29 – From Maker to Founder to Owner to Entrepreneur with Peldi Guilizzoni   
• 18:55 – Thinking big and small: Data-driven growth strategies to grow your business with Andrew Davies
• 20:45 – Contributing factors to the success of this event in particular
• 23:47 – 10 Lessons Learned in 10 Years of Starting, Growing, and Selling WebinarNinja with Omar Zenhom 
• 26:40 – Bootstrapping Our Freemium Form Builder: From Zero to $1.5M ARR with Marie Martens
• 30:37 – 3 mistakes I won’t repeat after growing my business to +35M and selling it with Tim Vandecasteele
• 33:50 – Breaking Through the 7 SaaS Growth Plateaus with Rob Walling

Links from the Show: 

• Get Tickets for MicroConf US 2025, New Orleans
• Signup for the MicroConf newsletter
• Derrick Reimer (@derrickreimer) | X
• SavvyCal
• Peldi from Balsamiq (@peldi) | X
• The SaaS Playbook
• Omar Zenhom (@TheOmarZenhom) | X
• Episode 717 | Bootstrapping to $1.3M ARR and 300,000 Free Users

If you have questions about starting or scaling a software business that you’d like for us to cover, please

Episode Sponsor:

Are you drowning in challenging tech decisions? You should check out today’s sponsor, Techstack. 

Unlike typical staffing agencies, these folks are startup specialists with over a decade of experience in startup software development.

Techstack can help your startup build an MVP that's designed for explosive growth, rapidly expand your team for new features, or optimize your existing codebase for peak performance. Whether you're launching, scaling up, or fine-tuning, they've got the expertise to supercharge your tech.

One of Techstack’s clients was recently featured on Inc. Magazine's Fast Growth Companies list, and they attributed part of their 375% growth to their partnership.

Here's an exclusive offer for "Startups For the Rest of Us" listeners: Get a 10% discount on your first month of development with Techstack. And if you're one of the first 10 listeners to get in touch, you'll also receive a free, in-depth tech assessment and expert consultation – a $3,000 value – in your choice of critical areas like architecture, infrastructure, development process or project management. This could be the game-changer your startup needs.

Don't let tech challenges slow you down. Check out https://www.tech-stack.com/startups  to discover how Techstack can turbocharge your growth.

Topics we cover: 

• 2:17 – What to delegate on the path to $10k MRR
• 6:43 – Be wary of social media marketing masquerading as productivity
• 10:31 – DIY vs. hiring a growth agency for B2B SaaS marketing
• 15:22 – Not every business should be a subscription business
• 22:00 – Defining, targeting, and selling to different ICPs

Links from the Show: 

• Get Tickets for MicroConf US 2025, New Orleans
• The SaaS Launchpad
• TinySeed
• The Stair Step Method of Bootstrapping
• Founding Sales by Peter Kazanjy
• Rob Walling (@robwalling) | X

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: