Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit

Startups For the Rest of Us

#Business #Entrepreneur #Marketing #Rob Walling #MBA #SaaS #Startup #Bootstrapped

40:22

There’s only so much you can do in a week – or, according to Oliver Burkeman, in the roughly 4,000 weeks the average human lives. Oliver is a journalist and author of the books Four Thousand Weeks: Time Management for Mortals, Meditations for Mortals, and the newsletter “The Imperfectionist.” Chris and Oliver discuss the paradox of why change can only occur once we accept that we might not be able to change. Oliver also shares how life’s mishaps can become our most treasured memories and why sharing your imperfections is an act of generosity. For the full text transcript, visit go.ted.com/BHTranscripts For the full text transcript, visit go.ted.com/BHTranscripts For a chance to give your own TED Talk, fill out the Idea Search Application: ted.com/ideasearch . Interested in learning more about upcoming TED events? Follow these links: TEDNext: ted.com/futureyou Hosted on Acast. See acast.com/privacy for more information.…

about a year ago 50:46

MP3•Episode home

What’s it take to bootstrap a niche SaaS to $90M without raising a dime?

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(9:14) – Why a mobile-first approach won in an outdated, overlooked niche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:

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

329 episodes

Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit

Startups For the Rest of Us

published about a year ago

MP3•Episode home

What’s it take to bootstrap a niche SaaS to $90M without raising a dime?

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(9:14) – Why a mobile-first approach won in an outdated, overlooked niche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:

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

329 episodes

#Business #Entrepreneur #Marketing #Rob Walling #MBA #SaaS #Startup #Bootstrapped

All episodes

Startups For the Rest of Us

1
Episode 786 | Questions About Bootstrapping SaaS to a $90M Exit (with Kevin Wagstaff) 44:46

6 days ago44:46

44:46

How do you really know when you’ve hit product-market fit? 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…

Startups For the Rest of Us

1
Episode 785 | Choosing Between AI Products, Building Multiple Apps, and More Listener Questions (A Rob Solo Adventure) 34:20

13 days ago34:20

34:20

How do you choose between multiple product ideas? 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…

Startups For the Rest of Us

1
Episode 784 | The Wealth Ladder: Six Levels of Financial Freedom 31:26

20 days ago31:26

31:26

What’s the real roadmap to lasting financial freedom? 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…

Startups For the Rest of Us

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Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit 40:31

27 days ago40:31

40:31

When is the right time to sell your profitable SaaS? 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…

Startups For the Rest of Us

1
Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions 27:46

5 weeks ago27:46

27:46

Looking back on your entrepreneurship journey, which decisions made the biggest impact? 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…

Startups For the Rest of Us

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Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again 39:39

6 weeks ago39:39

39:39

Are you repeating any of these mistakes in your business? 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…

Startups For the Rest of Us

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Episode 780 | "I'll Never Sell My Company" and Other Myths Founders Tell Themselves 42:28

7 weeks ago42:28

42:28

What if your biggest growth blocker isn’t the market, but the story you’re telling yourself? 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…

Startups For the Rest of Us

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Episode 779 | 10 Myths Most SaaS Founders Believe 44:32

8 weeks ago44:32

44:32

Are common SaaS myths sabotaging your success? 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…

Startups For the Rest of Us

1
Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure) 39:08

9 weeks ago39:08

39:08

How do you price pilot projects and niche down without hedging your bets? 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…

Startups For the Rest of Us

1
Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs 28:45

10 weeks ago28:45

28:45

What if the traditional dream of retirement is actually a trap for entrepreneurs? 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…

Startups For the Rest of Us

1
Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit 50:46

11 weeks ago50:46

50:46

What’s it take to bootstrap a niche SaaS to $90M without raising a dime? 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…

Startups For the Rest of Us

1
Episode 775 | A.I. Coding Tools, User Experience, Racking Your Own Servers, and More Listener Questions (with Derrick Reimer) 54:22

12 weeks ago54:22

54:22

What shortcuts are actually worth taking when you're building a SaaS? 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…

Startups For the Rest of Us

1
Episode 774 | How a Non-Technical Founder Bootstrapped to Millions in Revenue 37:09

13 weeks ago37:09

37:09

In this episode, Rob Walling sits down with Noah Tucker, the non-technical founder behind Social Snowball, an affiliate marketing SaaS built for Shopify. Noah bootstrapped the company to $5M+ in ARR, navigating technical roadblocks, team-building hurdles, and a crumbling codebase, while leveraging bold growth tactics like influencer partnerships to scale fast. 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…

Startups For the Rest of Us

1
Episode 773 | How to Find Your Early Customer Profile (ECP) 30:15

14 weeks ago30:15

30:15

In this episode, Rob Walling and Maja Voje, author of Go to Market Strategist , dive into early customer profiles (ECPs) and why they matter more than ideal customer profiles (ICPs) early on. They explore practical, scrappy marketing tactics for B2B SaaS founders and share real-world advice on customer acquisition, community building, and staying authentic while growing. 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…

Startups For the Rest of Us

1
Episode 772 | A Highly Effective Framework for SaaS Positioning 35:24

15 weeks ago35:24