Startups For the Rest of Us

Harris hit $20k MRR. It’s real. What’s next? In this episode of TinySeed Tales, Rob Walling celebrates with Harris Kenny after OutboundSync crosses $20k MRR ahead of schedule. They talk about why hitting a milestone can feel both exciting and overwhelming, the arrival fallacy, and how simple, consistent execution may be all it takes to reach $30k. Harris shares the bets that moved the needle, including Salesforce, SOC 2, and what hidden demand taught him about building integrations before anyone asked. Topics we cover:  (1:32) – Crossing $20k MRR and aiming for $30k (6:29) – The Salesforce bet (8:17) – Runway, burn, and pricing upmarket (10:34) – Raise capital or keep bootstrapping (15:03) – SOC 2 as a sales unlock (20:11) – Marketplace credibility and AppExchange (22:05) – Hidden demand for Salesforce (26:11) – The push to $30k and parity Links from the Show:  Invest in TinySeed Fund 3 Coaching Call Bonus MicroConf Events OutboundSync Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

B2C, low price point, one-time payments… not the typical recipe for a life-changing exit.   In this episode, Rob Walling talks with longtime listener Zamir Khan, founder of VidHug (now Memento). Zamir’s story broke a lot of SaaS “rules”: B2C, low price point, one-time payments, and years of slow growth. He shares how he nearly gave up, the pandemic surge that changed everything, and the emotional ride that led to a life-changing exit. Episode Sponsor: AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead. With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more. You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business. There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world.  Try it free at ahrefs.com/awt. Topics we cover:  (3:47) — From podcast listener to SaaS founder (7:59) — The role of luck, timing, and the pandemic in growth (18:37) — A birthday gift becomes a product (23:54) — Charging early and surviving slow growth (30:47) — From $1k a month to 80k daily users (39:58) — Support load, stress, and the edge of burnout (48:58) — Deciding to sell (and why timing mattered) (52:57) — Life after the exit: slowing down and finding balance Links from the Show:  TinySeed – Applications close tonight! MicroConf Connect – The community for SaaS founders The SaaS Playbook  Memento (formerly VidHug) Zamir Khan (@zam1rkhan) | X Zamir Khan  | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

What happens when momentum hits and your biggest challenge becomes keeping up? In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus. Topics we cover:  (1:40) – Closing his biggest deal ever and what it unlocked (4:26) – Learning how to do enterprise sales (6:20) – How SOC 2 made the product stronger (12:18) – New hires are paying off (18:23) – Building the Salesforce integration (22:13) – Getting pull from the market, not pushing (24:10) – Taking customers from unicorns  Links from the Show:  TinySeed SaaS Accelerator - Applications close on September 9th Coaching Call Bonus Invest in TinySeed YNAB (You Need A Budget) Dynamite Jobs OutboundSync Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter? In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal. Episode Sponsor This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up. Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at. Book your free strategy session at gearheart.io and mention Startups for the Rest of Us to get 20% off discovery, validation, or prototyping services. Topics we cover:  (3:12) – TinySeed returns Fund One (9:40) – GPT-5: Upgrade or letdown? (19:19) – Are we in an AI bubble? (24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees (31:06) – The bigger problem: Are startups forgetting to share the upside? (40:05) – Lifestyle vs. Ambitious Bootstrapping Links from the Show:  TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd TinySeed SaaS Accelerator - Applications are Open! Invest in TinySeed MicroConf SaaS Institute Discretion Capital  Einar Vollset | LinkedIn Einar Vollset (@einarvollset) | X Tracy Osborn  Tracy Osborn | LinkedIn Tracy Osborn (@tracymakes) | X If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work. Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything. Topics we cover:  (2:27) – Launching a lower-priced version and building expansion revenue (6:40) – How lead-gen shops are outpacing legacy rev ops (12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower (18:15) – A surprise Salesforce breakthrough and what it means for product strategy (24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check Links from the Show:  Join the TinySeed Mailing List Apply for TinySeed - Applications reopen September 1, 2025 OutboundSync Harris Kenny | LinkedIn Coaching Call Bonus Dynamite Jobs Vanta If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

How can you scale yourself as a founder? In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Violet, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every founder faces, and what happens if you don’t adapt. Topics we cover:  (3:27) – How the founder/CEO role changes as your SaaS scales (8:44) – The turning point where systems and processes matter (14:49 – When to hand off marketing, sales, or product as a founder (19:44) – Why setting context is your #1 job as a founder-CEO (28:19) – Why hiring right (and firing fast) makes or breaks scaling Links from the Show:  SaaS Institute MicroConf | The community for SaaS founders MicroConf YouTube Channel People Engineering  The SaaS Playbook  Yaniv Bernstein | LinkedIn Yaniv Bernstein (@ybernsteindig) | X The Startup Podcast If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between. In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owners are never able to make.  Topics we cover:  (2:25) – From agency owner to TinySeed-backed SaaS (6:38) – Walking away from consistent agency revenue to go all-in on SaaS (13:51) – Going all-in vs. splitting focus (16:13) – Why most agencies fail at SaaS (28:15) – What’s working, what’s not, and what’s next Links from the Show:  Join the TinySeed Mailing List - Applications reopen in September 2025 Apply for TinySeed Coaching Call Bonus MicroConf Connect OutboundSync The SaaS Playbook Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

What are the real risks of AI-generated code and “vibe coding”? In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction. Want to get your questions answered? Drop them here. Topics we cover:  (2:33) – Do you need a co-founder to succeed in SaaS? (5:18)  – The Risks of AI-Generated Code and “Vibe Coding” (13:50) – How to manage scope creep as a solo founder (23:32) – Finding and retaining great contractors (39:43) – How to build a startup culture with a bias for action Links from the Show:  MicroConf Europe | Istanbul, Sep 28-30, 2025 TinySeed Tales Podcast MicroConf Connect TinySeed Fund SavvyCal Derrick Reimer | LinkedIn Derrick Reimer (@derrickreimer) | X If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

How do you know it’s time to move on from a product that’s growing? In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue. Topics we cover:  (2:30) – From FinChat to Fiscal.ai: rebranding and repositioning (6:50) – Why they raised a $10M Series A (13:09) – From bootstrapped to venture-backed: what changes? (19:56) – Becoming a real CEO at 25 employees (26:44) – Why they shut down a $1.5M product (30:30) – Lessons from having four co-founders (33:13) – The benefits of joining TinySeed Links from the Show:  MicroConf Connect The Great CEO Within TinySeed: SaaS Institute Fiscal.ai (formerly FinChat) Braden Dennis (@BradoCapital) | X Braden Dennis | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

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

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

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

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

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

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

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

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

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

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

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