• 39 minutes 51 seconds
    Episode 834 | Eric Ries Revisits The Lean Startup and Discusses How to Become Incorruptible

    Is AI actually making your build-measure-learn cycle faster, or just making your work more average? 

    In this episode, Rob Walling talks with Eric Ries, author of The Lean Startup, to revisit what's held up in Lean Startup thinking 15 years on, why AI speeds up building but can't replace human learning, and what drove Eric to write his new book, Incorruptible. Eric also shares the story of how the Long-Term Stock Exchange nearly died before it ever launched, and why Costco is the rare example of a company that figured out how to stay incorruptible. 

    Topics we cover:

    • (3:48) – Lean Startup: 15 years later
    • (8:33) – How countercultural MVPs and pivots were
    • (11:02) – How AI changes build-measure-learn
    • (13:36) – Learning is still a human job
    • (15:43) – AI makes everyone's work more average
    • (17:39) – The Long-Term Stock Exchange story
    • (21:03) – How LTSE was nearly destroyed
    • (25:00) – A better definition of profit
    • (31:45) – Companies already living this way
    • (32:33) – The legend of Sol Price and Costco
    • (37:36) – Incorruptible: ethos plus integrity

    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!

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    26 May 2026, 10:00 am
  • 29 minutes 16 seconds
    Episode 833 | Success Patterns of Nobel Laureates, Developing Expertise, and From Zero to $10k (A Rob Solo Adventure)

    What do Nobel Prize winners and successful bootstrappers have in common? 

    In this solo episode, Rob Walling shares the story of how a TinySeed company went from near-zero revenue to $10,000-$20,000 a month almost overnight, breaks down Claude Shannon's research on the habits that separated Nobel laureates from forgotten scientists, and explores why deep expertise looks like magic from the outside.

    Episode Sponsor:

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    Topics we cover:

    • (2:46) – BlinkMetrics: from no product-market fit to $10-20K/month
    • (8:31) – 104 coffee chats, 24 sales calls 
    • (10:25) – AI changes custom dashboard economics 
    • (12:53) – What separates Nobel winners from the forgotten 
    • (14:40) – Knowledge compounds like interest 
    • (18:28) – Taking bigger swings vs. staying in your comfort zone
    • (19:36) – Going deep on one idea for years 
    • (21:21) – Expertise that looks like magic 

    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

    19 May 2026, 10:00 am
  • 34 minutes 17 seconds
    Episode 832 | Going Full-time, When to Pivot, Building With Young Kids, and More Listener Questions (Rob Solo)

    How do you leave a $400K salary to go all in on your business?

    In this solo episode, Rob Walling cranks through a backlog of listener questions on reducing risk with your startup to go full-time, when to register as a business, how to price a SaaS with seat ambiguity, when to pivot, and how to keep building when you have four kids under eight. 

    Want to get your question answered? Drop it here.

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    Topics we cover:

    • (2:15) – Leaving a $400K salary to go full-time
    • (7:43) – When to officially register your business
    • (10:51) – Seat-based pricing with shared branding
    • (12:40) – When to get a design audit
    • (15:05) – How to calculate TAM for a Shopify app
    • (18:29) – Can a step one app break free of its marketplace?
    • (20:22) – How to know when it's time to pivot
    • (22:31) – Building a startup with four young kids
    • (25:30) – How to find ICP conversations without a network

    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

    12 May 2026, 10:00 am
  • 43 minutes 56 seconds
    Episode 831 | Written vs. Verbal Ad Copy, Selling Into a Low-Awareness Market, and More Listener Questions (Rob Solo)

    Should your first customer pay you, or get your product for free? 

    In this episode, Rob Walling answers listener questions on charging customer zero, what metrics to track for a seasonal transaction fee-based SaaS, what it really means to sell into a low-awareness market, and when freelancers help vs. hurt your bootstrapped business. He also calls in Producer Ron to break down exactly how he thinks about writing copy for a podcast ads. Want to get your question answered? Drop it here.

    Topics we cover:

    • (2:42) – Six years to overnight success
    • (4:55) – Should customer zero pay or get it free?
    • (8:42) – Writing ad copy for podcast ads
    • (15:14) – Metrics for a transaction fee-based SaaS
    • (18:40) – Moving from GMV-only to subscription plus fees
    • (20:38) – Selling into a low-awareness market
    • (23:53) – When bootstrappers struggle without problem awareness
    • (27:09) – Podcast music history editor Josh
    • (31:44) – How to find and work with freelancers

    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

    5 May 2026, 10:00 am
  • 35 minutes 44 seconds
    Episode 830 | Breaking Through Plateaus, Zero-Click Marketing, and More from MicroConf 2026 (with Derrick Reimer)

    What were the highlights and takeaways from MicroConf? 

    In this episode, Rob Walling and Derrick Reimer recap MicroConf US 2026 in Portland, Oregon. They break down the best talks from the event, including Jason Cohen on breaking through growth plateaus, Amanda Natividad on Zero-Click Marketing and broken attribution, Rob's framework for six ways to implement AI in SaaS, and Craig Hewitt's all-in take on AI adoption. Plus, they cover excursions, the hallway track, and why the MicroConf community keeps pulling founders up.

    Episode Sponsor:

    You're about to close a massive deal, and then your customer's legal team asks what happens if you get hacked. 

    That's the nightmare YSecurity solves. They're 40 security engineers who've worked at Apple, Uber, Microsoft, Robinhood, Brex, and more. You don't hire them, you rent them by the hour, no massive salary, no expensive consultants. Just real experts helping you get SOC 2, ISO, and more.

    Set a monthly cap, know exactly what you're spending, and close the deal. 

    Head to ysecurity.io/startups to book your free strategy call. Your first 8 hours are completely free.

    Topics we cover:

    • (2:14) – MicroConf 2026 attendee caliber and mix
    • (5:07) – Rebuilding MicroConf post-COVID
    • (8:51) – Jason Cohen on breaking growth ceilings
    • (12:48) – Amanda Natividad on Zero-Click Marketing
    • (19:30) – Excursions, arcades, and the hallway track
    • (22:01) – Rob's six ways to implement AI in SaaS
    • (27:27) – Gia Laudi on Jobs To Be Done as your GTM moat
    • (29:00) – Craig Hewitt's "AI Doomer" talk
    • (33:41) – MicroConf Europe in Iceland

    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

    28 April 2026, 10:00 am
  • 30 minutes 37 seconds
    Episode 829 | AI is Bad at Product, Top 5 Startup Success Factors, and the Beastie Boys (A Rob Solo Adventure)

    Can AI really handle product decisions for your SaaS?

    In this solo adventure, Rob Walling revisits the core four SaaS skills and breaks down what AI can and cannot do across Development, Sales, Marketing, and Product. He also reframes Bill Gross's top five startup success factors for bootstrappers, walks through a hilariously bad UX decision by a local parking app, and closes with a surprisingly insightful Beastie Boys anecdote about shipping creative work into the world.

    Episode Sponsor:

    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. 

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    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.

    Topics we cover:

    • (5:48) – AI and the Core Four SaaS skills
    • (7:03) – Why AI falls short with sales and marketing
    • (8:45) – The editorial eye AI still lacks
    • (10:14) – Why AI is worst at product
    • (13:41) – Bill Gross's top five startup success factors
    • (19:48) – A parking app's terrible UX decisions
    • (24:24) – The Beastie Boys and lessons on shipping

    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

    21 April 2026, 10:00 am
  • 41 minutes 28 seconds
    Episode 828 | Am I Building a SaaS?, Serving Both B2C and B2B, Pricing, and More Listener Questions (Rob Solo)

    Is your product actually a SaaS?

    In this episode, Rob Walling tackles listener questions about what really qualifies as SaaS (and where he disagrees with ChatGPT), how to serve both solopreneurs and enterprise customers with a dual funnel strategy, layering a B2B offering on top of a B2C product, pricing a mission-driven app without gatekeeping access, and the impact of healthcare costs on startup runway.

    Want to get your question answered? Drop it here.

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    Topics we cover:

    • (3:09) – What qualifies as a SaaS business?
    • (5:15) – Why Netflix and Spotify are not SaaS
    • (8:11) – Where Rob disagrees with ChatGPT on SaaS
    • (12:21) – Serving solopreneurs and enterprise simultaneously
    • (15:13) – The power of the dual funnel strategy
    • (17:02) – Navigating the enterprise sales process
    • (22:20) – Layering B2B features onto a B2C product
    • (28:52) – Pricing a mission-driven job search app
    • (35:57) – Healthcare costs and startup runway in the US

    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

    Listen to Episode 828

    14 April 2026, 10:00 am
  • 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.

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    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.

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    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.

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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.

    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
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