Startups For the Rest of Us

Rob Walling

The most popular podcast for bootstrapped and mostly bootstrapped startup founders

  • 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.

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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: 

    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
  • 22 minutes 55 seconds
    Episode 816 | Developing an Editorial Eye, The Right Kind of Stubborn, and The Power of Focus (A Rob Solo Adventure)

    Have you ever pushed so hard on an idea that you missed the signal to change direction?

    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: 

    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

    20 January 2026, 10:00 am
  • 30 minutes 43 seconds
    Episode 815 | Unexpected Skills Your Day Job Can Teach You About Entrepreneurship (Rob Solo)

    Can your 9-to-5 job secretly prepare you to be a founder?

    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: 

    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

    13 January 2026, 10:00 am
  • 36 minutes 16 seconds
    Episode 814 | How to Beat a Venture-Backed Competitor (with Laura Roeder)

    What’s it take for a bootstrapped SaaS to beat a competitor with $10M in venture funding?

    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: 

    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

    6 January 2026, 10:00 am
  • 28 minutes 6 seconds
    Episode 813 | SaaS Predictions for 2026 (+ Reflections on 2025)

    How will AI, SEO, and market shifts change SaaS next year?

    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 [email protected]

    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: 

    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

    30 December 2025, 10:00 am
  • 28 minutes 46 seconds
    Episode 812 | The 2025 State of TinySeed

    After funding 210+ B2B SaaS companies, what patterns have emerged?

    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: 

    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

    23 December 2025, 10:00 am
  • 34 minutes 15 seconds
    Episode 811 | When to Delegate the "Core Four SaaS Skills," Freemium Retention Rates, and More Listener Questions (A Rob Solo Adventure)

    How do you step back from daily decisions without losing control of your SaaS?

    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:

    Struggling to make Google Ads work for your SaaS?

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     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: 

    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

    16 December 2025, 10:00 am
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