Startups For the Rest of Us

Rob Walling

The most popular podcast for bootstrapped and mostly bootstrapped startup founders

  • 40 minutes 17 seconds
    Episode 827 | The Founder's Guide to Selling Your SaaS for What It's Actually Worth

    What would it mean for you to leave 60 or 70% of your company's value on the table when you sell?

    In this episode, Rob sits down with Einar Vollset, co-founder of TinySeed and founder of Discretion Capital, to talk about his new book, The Definitive Guide to M&A for B2B SaaS between $2 and $20 million ARR. They dig into why private equity now dominates the buyer landscape, why growth and churn are the top two valuation drivers, and how the myth that "startups are bought, not sold" could cost you millions.

    Einar also explains the danger of running your business past its peak growth rate before selling, why ARR multiples matter more than profit, and how the right M&A advisor can add 30 to 300% to an initial offer.

    Episode Sponsors:

    This episode is brought to you by Mercury

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

    Traditional banking is broken, slow wires, clunky interfaces, tools that feel like they were built in 2005. 

    Mercury is what banking should feel like in 2026. Everything just works.

    Whether it's daily bill pay or wiring large sums to the dozens of companies we invest in each year, Mercury handles it. Simple when I need simple, robust when I need approvals and controls.

    Over 300,000 entrepreneurs have made the switch. When founders ask me where to set up their account, I send them to mercury.com. 

    Free to get started, no in-person visits, no minimum balance.

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

    Everyone's talking about AI in marketing. But AI without strategy just means generating more bad marketing, faster.

    The founders who win aren't the ones using the most tools, they're the ones with a real system behind their growth. Positioning, persuasion, conversion. That's what moves the needle.

    That's what Conversion Factory does. They're a SaaS marketing and design agency that has worked with over 100 startups, including several TinySeed companies.

    Book a call at https://conversionfactory.co/ and mention this podcast for $1,000 off your first month. And if you're at MicroConf US in Portland, grab Corey Haines in the hallway track to see how they can help you.

    Topics we cover:

    • (3:34) – Why Einar wrote an M&A guide for SaaS founders
    • (5:26) – How founders leave value on the table when selling
    • (8:22) – How private equity moved down market
    • (11:24) – Choosing the right broker or banker
    • (12:55) – Platform acquisitions vs. tuck-ins explained
    • (19:24) – Why "startups are bought, not sold" is wrong
    • (25:48) – Growth and churn as top valuation drivers
    • (30:02) – Why ARR multiples matter more than profit
    • (34:34) – The danger of running past peak growth

    Links from the show:

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

    Subscribe & Review: iTunes |Spotify

    7 April 2026, 10:00 am
  • 31 minutes 47 seconds
    Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers

    How do you find someone who thinks like an owner, not just a task-doer?

    In this episode, Rob digs into a batch of listener questions about task level, project level, and owner level thinkers. He covers how to identify them, what they cost, where to find them, and why building a team of exceptional people creates a virtuous cycle that lifts everyone up.

    Topics we cover:

    • (4:13) – Defining task, project, and owner level thinkers
    • (7:32) – Are owner level thinkers born or built?
    • (10:16) – Compensation ranges for owner level thinkers
    • (11:53) – W2 vs. contractor for senior hires
    • (15:53) – Do you actually need owner level thinkers?
    • (17:36) – Where to find project and owner level thinkers
    • (20:16) – How long to integrate them into your company
    • (24:40) – How to identify them in job interviews
    • (29:38) – Why you won't always get hires right

    Links from the show:

    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

    31 March 2026, 10:00 am
  • 50 minutes 24 seconds
    Episode 825 | Talking Tailwind CSS and Founder Fitness (with Adam Wathan)

    What happens when AI starts competing with your open source business?

    In this episode, Rob Walling sits down with Adam Wathan, co-founder of Tailwind CSS, for a candid conversation about the dramatic revenue decline that forced Tailwind Labs to lay off most of their team. Adam shares the hard lessons learned from running a business based on one-time purchases, why he didn't see the slowdown coming, and how an honest podcast episode accidentally turned everything around.

    Then they switch gears entirely to talk about founder fitness: how Adam lost 70 pounds, his 15-minute weighted vest workouts, and why tracking strength gains can be more motivating than watching the scale.

    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.

    G2i cuts through all of that. They've pre-vetted over 8,000 engineers- not "we glanced at their GitHub" vetted, actually tested with live technical interviews. Contract or full-time- just tell them what you need and within days you're reviewing real candidates.

    And you get a risk-free trial. If it's not a fit, they'll replace the dev in 24 hours.

    G2i is trusted by companies like Meta, 1Password, 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 

    ️ Want to attend their AI Miami in April? Use promo code use Rob50Off

    Topics we cover:

    • (4:43) – Adam's history with Tailwind CSS
    • (5:17) – Revenue decline and the "boiling frog" problem
    • (8:30) – Making the hard decision to lay off the team
    • (11:39) – The viral podcast episode and unexpected sponsors
    • (13:07) – Should Tailwind have used recurring revenue?
    • (21:20) – Enterprise pricing and team licenses
    • (25:47) – What's next: Ui.sh and swimming downstream with AI
    • (27:40) – Founder fitness: 15-minute weighted vest circuits
    • (33:01) – Tracking strength gains as motivation
    • (39:13) – Did getting fit make Adam a better founder?

    Links from the show:

    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

    24 March 2026, 10:00 am
  • 55 minutes 15 seconds
    Episode 824 | Crowded Markets, Problem Aware, A Stolen Idea, and More Listener Questions (with Jordan Gal)

    What do you do when a collaborator takes your idea and builds a competing product?

    In this episode, Rob Walling is joined by fan favorite Jordan Gal to answer listener questions on some of the trickiest challenges founders face. They cover financing decisions like using debt to bridge cash flow gaps, competing in markets flooded with vibe-coded apps, and what to do when a collaborator takes your idea and runs with it.

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

    Episode Sponsor:

    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.

    Topics we cover:

    • (3:50) – Jordan Gal on Rosie's multichannel launch
    • (8:01) – Investing cash in slow-moving healthcare markets
    • (10:32) – Using debt or credit against signed contracts
    • (16:48) – Competing in crowded markets with vibe-coded apps
    • (24:34) – Should you offer advisory shares to design partners?
    • (30:38) – Selling to problem-aware but not solution-aware audiences
    • (37:35) – When a collaborator steals your startup idea

    Links from the show:

    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

    17 March 2026, 10:00 am
  • 41 minutes 42 seconds
    Episode 823 | Hot Take Tuesday: Is A.I. Killing B2B SaaS?, ChatGPT Ads, OpenClaw

    Is AI really killing B2B SaaS, or is it just subscription software by another name?

    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.

    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:

    • (3:52) – 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:

    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

    10 March 2026, 10:00 am
  • 51 minutes 43 seconds
    Episode 822 | No-code vs. A.I. Coding, SaaS Margins in the A.I. Age, and More Listener Questions (with Derrick Reimer)

    Should you build your SaaS with no-code tools, or is AI coding the better path forward?

    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.

    G2i cuts through all of that. They've pre-vetted over 8,000 engineers- not "we glanced at their GitHub" vetted, actually tested with live technical interviews. Contract or full-time- just tell them what you need and within days you're reviewing real candidates.

    And you get a risk-free trial. If it's not a fit, they'll replace the dev in 24 hours.

    G2i is trusted by companies like Meta, 1Password, 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 

    ️ Want to attend their AI Miami in April? Use promo code Rob50Off

    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:

    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

    3 March 2026, 10:00 am
  • 33 minutes 52 seconds
    Episode 821 | How to Do Founder-Led Marketing (with Jay Clouse)

    Is founder-led marketing right for your SaaS, or just a distraction?

    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.

    Need to ship faster without expanding your team?

    Gearheart is an AI-powered product studio that helps startups build B2B SaaS apps and AI agents, fast. Their team ships at twice the speed of traditional dev shops and understands how to work within startup constraints.

    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: 

    • (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: 

    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

    24 February 2026, 10:00 am
  • 32 minutes 56 seconds
    Episode 820 | When to Quit Your Day Job, A.I. Feasibility Risk, and More Listener Questions (Rob Solo)

    When do you finally quit your day job and go all-in on your startup?

    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: 

    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

    17 February 2026, 10:00 am
  • 33 minutes 30 seconds
    Episode 819 | QSBS, Exit Multiples, How to Learn Marketing, and More Listener Questions (Rob Solo)

    Could your business structure quietly cost you millions when you sell?

    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: 

    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

    10 February 2026, 10:00 am
  • 55 minutes 41 seconds
    Episode 818 | What Does It Take to Be Successful? with Russ Walling

    Is perfectionism quietly sabotaging your career or startup dreams?

    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: 

    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

    3 February 2026, 10:00 am
  • 53 minutes 30 seconds
    Episode 817 | Bootstrapping in the Age of AI with Jason Cohen

    How would a 2x unicorn founder build his next startup with AI?

    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: 

    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

    27 January 2026, 10:00 am
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