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Our Skin: A Personal Discovery Podcast
1 You Are Your Longest Relationship: Artist DaQuane Cherry on Psoriasis, Art, and Self-Care 32:12
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LikedDaQuane Cherry was once the kid who wore a hoodie to hide skin flare-ups in school. Now he’s an artist and advocate helping others feel seen. He reflects on his psoriasis journey, the power of small joys, and why loving yourself first isn’t a cliché—it’s essential. Plus, a deep dive into the history of La Roche-Posay’s legendary spring. See omnystudio.com/listener for privacy information.…
Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit
Manage episode 485212437 series 2455819
Content provided by Rob Walling. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Rob Walling or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.
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- (9:14) – Why a mobile-first approach won in an outdated, overlooked niche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!
439 episodes
ShareManage episode 485212437 series 2455819
Content provided by Rob Walling. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Rob Walling or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.
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!
439 episodes
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1 Episode 784 | The Wealth Ladder: Six Levels of Financial Freedom 31:26
31:26 Play Later Play Later Lists Like Liked31:26
Play Later Play Later Lists Like LikedWhat’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…
1 Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit 40:31
40:31 Play Later Play Later Lists Like Liked40:31
Play Later Play Later Lists Like LikedWhen 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…
1 Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions 27:46
27:46 Play Later Play Later Lists Like Liked27:46
Play Later Play Later Lists Like LikedLooking 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…
1 Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again 39:39
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Play Later Play Later Lists Like LikedAre 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…
1 Episode 780 | "I'll Never Sell My Company" and Other Myths Founders Tell Themselves 42:28
42:28 Play Later Play Later Lists Like Liked42:28
Play Later Play Later Lists Like LikedWhat 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…
1 Episode 779 | 10 Myths Most SaaS Founders Believe 44:32
44:32 Play Later Play Later Lists Like Liked44:32
Play Later Play Later Lists Like LikedAre 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…
1 Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure) 39:08
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Play Later Play Later Lists Like LikedHow 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…
1 Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs 28:45
28:45 Play Later Play Later Lists Like Liked28:45
Play Later Play Later Lists Like LikedWhat 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…
1 Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit 50:46
50:46 Play Later Play Later Lists Like Liked50:46
Play Later Play Later Lists Like LikedWhat’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…
1 Episode 775 | A.I. Coding Tools, User Experience, Racking Your Own Servers, and More Listener Questions (with Derrick Reimer) 54:22
54:22 Play Later Play Later Lists Like Liked54:22
Play Later Play Later Lists Like LikedWhat 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…
1 Episode 774 | How a Non-Technical Founder Bootstrapped to Millions in Revenue 37:09
37:09 Play Later Play Later Lists Like Liked37:09
Play Later Play Later Lists Like LikedIn 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…
1 Episode 773 | How to Find Your Early Customer Profile (ECP) 30:15
30:15 Play Later Play Later Lists Like Liked30:15
Play Later Play Later Lists Like LikedIn 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…
1 Episode 772 | A Highly Effective Framework for SaaS Positioning 35:24
35:24 Play Later Play Later Lists Like Liked35:24
Play Later Play Later Lists Like LikedHow do you position your SaaS for success? In episode 772, Rob Walling talks with Anthony Pierri of Fletch about a proven approach to product positioning. They discuss key lessons from 400+ startups, focusing on workflows, competitive alternatives, and why narrowing your audience matters. Topics we cover: (6:59) – What is positioning, really? (11:16) – Why your homepage matters more than your pitch deck (14:17) – Workflow-based segmentation vs. firmographics (17:39) – Positioning against competitive alternatives (31:13) – The #1 mistake founders make with positioning Links from the Show: MicroConf Growth Retreat | London, UK - May 14-16, 2025 Invest in TinySeed Get Access to Anthony’s MicroConf New Orleans Talk Anthony Pierri (@anthonypierri) | LinkedIn Anthony Pierri (@apierriPMM) | X Fletch 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…
1 Episode 771 | What Changes As You Grow, AI Agents, Patents, and More Listener Questions (with Craig Hewitt) 38:48
38:48 Play Later Play Later Lists Like Liked38:48
Play Later Play Later Lists Like LikedCan SaaS companies survive the rise of AI Agents? In episode 771, Rob Walling is joined by Craig Hewitt to answer listener questions. They discuss the changes that happen while transitioning from a small startup to a multi-million dollar SaaS, competing against larger competitors, and maintaining startup culture as teams grow. They also share thoughts on AI agents in the SaaS space and the relevance of patents for bootstrapped businesses. 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: (2:41) – Marketing and sales strategies while scaling (9:31) – Keeping the startup culture through growth (14:50) – Can SaaS survive autonomous agents? (21:03) – AI wrapper tools (25:15) – Patent strategy for startups (29:30) – Competing against VC-backed companies Links from the Show: MicroConf Remote: Early-Stage SaaS Sales Invest in TinySeed Craig Hewitt (@TheCraigHewitt) | X Craig Hewitt (@craighewitt.com) | Bluesky Rouge Startups Castos Omar Zenhom Omar Zenhom’s MicroConf Talk AI Agents vs SaaS - Who Wins the Future of Software? Episode 542 | 10x in Two Years, Past $3M ARR with SquadCast 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…
1 Episode 770 | Revenue vs. Profit, Asking for Permission, and Mike Tyson (A Rob Solo Adventure) 25:05
25:05 Play Later Play Later Lists Like Liked25:05
Play Later Play Later Lists Like LikedIs it more important for entrepreneurs to focus on revenue or profit? In episode 770, Rob Walling goes solo to explore the relationship between revenue and profit in SaaS, and the dangers of waiting for permission. He also draws inspiration from Mike Tyson’s work ethic and George Lucas’ visionary mindset to encourage entrepreneurs to push through obstacles and innovate. Topics we cover: (2:41) – MRR versus ARR (8:04) – Don’t ask for permission, don’t give in to defeatism (14:38) – Inventing to pursue novel visions (18:48) – Mike Tyson’s training regimen (20:48) – You don’t need to be the best in the world Links from the Show: MicroConf Growth Retreat Discretion Capital Email Einar Rob Walling (@robwalling) | X Rob Walling | 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…
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Startups For the Rest of Us
1 Episode 769 | Key Insights from MicroConf 2025 in New Orleans 30:53
30:53 Play Later Play Later Lists Like Liked30:53
Play Later Play Later Lists Like LikedDid you miss out on MicroConf US in New Orleans? In episode 769, Rob Walling welcomes Derrick Reimer back to share highlights from MicroConf New Orleans. They dive into the event's vibrant atmosphere, standout founder talks, and the energizing mix of new and familiar faces that made this gathering in the Big Easy truly special. Topics we cover: (1:40) – MicroConf New Orleans audience breakdown (5:50) – Upcoming MicroConf events (9:05) – 5 Lessons That Exits Teach Us About Running Our Business (12:35) – Anthony Pierri’s talk about homepage positioning (15:16) – 4 New Orleans excursions (17:17) – Talks on copywriting, pricing, and LinkedIn outreach (25:57) – Reviewing attendee feedback Links from the Show: MicroConf Connect Applications Open Until April 9th MicroConf Growth Retreat MicroConf Europe 2025 MicroConf Remote Exit Strategy by Sherry Walling, PhD & Rob Walling Derrick Reimer (@derrickreimer) | X Derrick Reimer(@derrickreimer.com) | Bluesky SavvyCal Episode 737 | Key Takeaways from MicroConf Europe 2024 (With Derrick Reimer) Anthony Pierri (@apierriPMM) | X Lianna Patch (@punchlinecopy.com) | Bluesky Street Pricing by Marcos Rivera Episode 765 | TinySeed Tales s4e9: Making the hardest decision 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…
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Startups For the Rest of Us
1 Episode 768 | Reacting to Controversial Startup Advice 29:36
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Play Later Play Later Lists Like LikedDo you disagree with any of these controversial takes about bootstrapping? In episode 768, Rob Walling unpacks a series of semi-controversial beliefs about bootstrapping from ScrapingBee’s Pierre de Wulf. Rob evaluates each point from Pierre's tweet, discussing topics like rebranding your SaaS, the hidden problem of affiliate marketing, and the realities of scaling a SaaS business. Topics we cover: (1:21) – Pierre’s semi-controversial bootstrapping beliefs (4:35) – Don’t waste time on a rebrand (7:24) – No one cares about your domain extension (9:06) – Affiliate marketing won’t fix your acquisition issues (11:51) – There is no silver bullet for growth (13:42) – Copy what works best (14:59) – Double down on acquisition channels that work (16:53) – Hire specialists (19:34) – Never offer a plan with unlimited features (20:22) – Don’t offer a cheap plan if you can’t support it (20:47) – Don’t add social logins to your signup page (21:27) – Read competitors’ reviews several times a year (21:59) – $10k MRR doesn’t guarantee $100k MRR (22:28) – You will get copied if you share success (23:02) – “Build this feature…” (24:10) – The Mom Test (24:56) – Provide value for your target demographic for free (25:47) – Don’t overthink Product Hunt (26:00) – You’ll never sell your SaaS for 10x Links from the Show: MicroConf Growth Retreat in London Rob Walling (@robwalling) | X Pierre de Wulf (@PierreDeWulf) | X ScrapingBee (@ScrapingBee) | X ScrapingBee Pierre’s semi-controversial bootstrapping beliefs TinySeed Rob Walling.com Rob Walling | LinkedIn SaaS Institute Exit Strategy by Sherry Walling, PhD & Rob Walling Episode 705 | From Bootstrapped to Mostly Bootstrapped to Venture Backed The Mom Test by Rob Fitzpatrick Deploy Empathy by Michele Hansen The SaaS Playbook by Rob Walling 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…
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1 Episode 767 | Finding Your ICP, Prioritizing Feature Requests, Pricing, and More Product-Focused Listener Questions 42:43
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Play Later Play Later Lists Like LikedIs product management more of an art, or a science? In episode 767, Rob Walling is joined again by Brendan Fortune to answer listener questions focused on product management. They discuss identifying your ideal customer profile, prioritizing feature requests, and positioning against competitors. They also weigh in on how product managers should focus their time. Topics we cover: (2:50) – Is your ideal customer always your highest paying one? (8:11) – Finding just one ICP can be difficult (14:56) – How do you prioritize feature requests? (19:24) – Product management is art and science (26:02) – Competing with competitors on value, not price (32:21) – How should product managers focus their time? (37:20) – How do PMs manage roadmaps and user feedback? Links from the Show: Invest in TinySeed MicroConf Mastermind Applications close March 31st MicroConf Growth Retreat The SaaS Playbook Brendan Fortune | LinkedIn Customer.io Episode 756 | Why Great Product Management Is Critical for Your Startup Product Flywheel + Pricing + Org Strategy (Miro) Savio 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…
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1 Episode 766 | Close.com's Amazing Run to $40M ARR (with Steli Efti) 37:13
37:13 Play Later Play Later Lists Like Liked37:13
Play Later Play Later Lists Like LikedHow do you achieve both success and longevity in SaaS? In episode 766, Rob chats with Steli Efti about growing Close.com to over $40 million in ARR. Steli shares insights into the importance of maintaining strong co-founder relationships over 12 years, navigating crises, and the importance of emotional resilience in entrepreneurship. They also dive into Close's recent pricing shift to introduce a lower entry-level plan. Topics we cover: (2:08) – Reflecting on 12 years of SaaS at Close (3:50) – Strong co-founder relationships (11:24) – Longevity and consistently showing up (20:23) – Surviving moments of crisis (29:27) – Launching a more affordable pricing tier (34:40) – Getting back into the content game Links from the Show: Exit Strategy by Sherry Walling, PhD & Rob Walling Close Close Sales Guides Episode 498 | Selling During a Pandemic with Steli Efti The 0 to $30 Million Blueprint Steli Efti (@Steli) | X Steli Efti | 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…
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1 Episode 765 | TinySeed Tales s4e9: Making the hardest decision 28:20
28:20 Play Later Play Later Lists Like Liked28:20
Play Later Play Later Lists Like LikedIs it time to shut down for good? In this season finale of TinySeed Tales, Rob Walling sits down with Colleen Schnettler, founder of Hello Query, to reflect on her journey over the past few years. Colleen candidly shares the challenges she faced while trying to grow her SaaS business, including the difficult decision to shut it down after struggling to find traction. Moving past a painful part in her founder journey, Colleen is excited about her new venture where she’s already seeing early success. Join us for this honest look into the final days of Hello Query and to hear Colleen's resilience in the startup world. Topics we cover: (1:07) – Difficulty in finding and onboarding customers (5:32) – Why didn’t it work? (9:29) – How did the co-founder split affect the business? (13:11) – Founder regrets (18:49) – Reflecting on the decision (22:38) – Anything that you would have done differently? (25:21) – Moving forward to founder coaching and marketing Links from the Show: Join the TinySeed Mailing List Apply for TinySeed SaaS Marketing Gym Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Hello Query The Score Takes Care of Itself by Bill Walsh 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…
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1 Episode 764 | Finding Hockey Stick Growth with an A.I. Wrapper (with Jordan Gal) 39:53
39:53 Play Later Play Later Lists Like Liked39:53
Play Later Play Later Lists Like LikedHow do you build an MVP for an AI-enabled SaaS? In episode 764, Rob Walling interviews Jordan Gal, co-founder of Rosie, to learn about how he pivoted from Rally to build an AI-driven product for small business owners. Jordan shares insights into the challenges of finding product-market fit, the importance of trial and error, and the rapid growth Rosie has experienced since its launch. They delve into the significance of effective onboarding, and how building an MVP changes in the face of AI. Topics we cover: (2:38) – From CartHook to Rally to Rosie (6:28) – Deciding to pivot and feeling product-market fit (12:55) – Coming up with a feature set (16:50) – Building an MVP quickly (19:29) – Competition when developing with AI (24:52) – Removing features and flexibility in software (29:59) – Incredibly fast onboarding (33:22) – Balancing a “better business” with a “faster business” Links from the Show: Applications for MicroConf Mastermind Matching are Open through March 31st SaaS Institute Rosie Jordan Gal (@JordanGal) | X Rosie (@heyrosieai) | X Episode 549 | Hiring vs. Outsourcing, E-commerce SaaS, and More Listener Questions with Jordan Gal 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…
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1 Episode 763 | TinySeed Tales s4e8: One Last Pivot 15:20
15:20 Play Later Play Later Lists Like Liked15:20
Play Later Play Later Lists Like LikedIs it time to set a deadline for when to quit your startup? In this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hello Query, as she tries to achieve product-market fit on a deadline. Colleen reveals the struggles of cold outreach and the overwhelming data landscape while testing a potential solution. With a clearer vision and two paying customers, she reflects on the importance of defining her value proposition, and the critical timeline she has set for herself to gain traction before her runway ends. Topics we cover: (1:43) – Debating becoming a data aggregator (6:30) – Finding a new direction (8:21) – Running out of runway (10:39) – When is it time to quit? Links from the Show: The SaaS Launchpad Quit by Annie Duke TinySeed Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Hello Query 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…
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1 Episode 762 | Doing Great Work, Hierarchy of SaaS Skills, and Public Deadlines (A Rob Solo Adventure) 25:05
25:05 Play Later Play Later Lists Like Liked25:05
Play Later Play Later Lists Like LikedAre public deadlines a double-edged sword for startup founders? In episode 762, join Rob Walling for a solo adventure where he covers several topics. Rob breaks down Paul Graham's essay, "Doing Great Work" and focuses on how the steps apply to building real businesses for real customers. He also discusses the hierarchy of skills necessary for success in the SaaS space, sharing his thoughts on the critical roles of marketing, product development, engineering, and effective team management. Topics we cover: (2:07) Doing great work (5:20) Identify the gaps (11:51) The SaaS skillset hierarchy (18:28) Publicly committing to a feature release (23:05) Maintaining enough rigor to hit deadlines Links from the Show: MicroConf Connect Applications are open now through March 5th How to Do Great Work by Paul Graham Start Small Stay Small by Rob Walling Episode 756 | Why Great Product Management Is Critical for Your Startup 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…
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1 Episode 761 | TinySeed Tales s4e7: Identifying Pain Points 20:34
20:34 Play Later Play Later Lists Like Liked20:34
Play Later Play Later Lists Like LikedIn this episode of TinySeed Tales, Rob Walling checks in with Colleen Schnettler, co-founder of Hello Query, as she discusses finding customer pain points. Colleen, now solo, navigates the challenge of refining her product vision. After a period of introspection, Colleen shares her decision to pivot from targeting engineering managers to focusing on marketing data analysts. She discusses the insights gained from hiring a marketing coach and the excitement of landing her first paying customer, despite some critical feedback on her product's UI. Topics we cover: (1:50) – Early product excitement fizzles out (5:14) – When is it time to move on from an idea? (8:57) – Helping marketers build better reports (13:03) – Setting early pricing (14:02) – Determining how much to polish an MVP (17:36) – Predicting what’s ahead Links from the Show: SaaS Institute TinySeed Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Hello Query 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…
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1 Episode 760 | White-Labeling, Founder Mindset, and More Listener Questions (A Rob Solo Adventure) 32:38
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Play Later Play Later Lists Like LikedIn episode 760, join Rob Walling as he takes on some listener questions in another solo adventure. He offers insights on balancing custom-built solutions versus white-labeled components, and the impact white labeling has on company valuation and growth. He also discusses strategic hiring, founder mindsets, and tools for tracking your SaaS success. Topics we cover: (2:30) – Considerations when white-labeling within your SaaS (9:03) – Does relying on other SaaS affect our valuation? (10:10) – Tools for tracking SaaS metrics to enable scaling (17:03) – Do founder mindsets change at MRR milestones? (21:34) – Mistakes founders make in their mindset (25:27) – Forcing an onboarding step (27:29) – Determining team composition Links from the Show: The SaaS Launchpad The SaaS Playbook Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure) Invest in TinySeed Episode 685 | 7 Things You Should Never Do (A Rob Solo Adventure) Episode 722 | Bootstrapping a Vertical SaaS to 7-Figures in 18 Months 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…
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1 Episode 759 | TinySeed Tales s4e6: Does AI + Pivot = Success? 27:10
27:10 Play Later Play Later Lists Like Liked27:10
Play Later Play Later Lists Like LikedIn this episode of TinySeed Tales, Rob Walling speaks with Colleen Schnettler, co-founder of Hello Query, as she shares her latest startup journey pivot. After reigniting her “shipping muscle” while briefly dabbling in an AI-based project, Colleen refocuses on her newest pivot of Hello Query. She shares the challenges of determining the market viability of an AI-assisted SQL report builder. She stands at a crossroads, torn between catering to internal BI teams or exploring marketing analytics. Topics we cover: (1:25) – Reflecting on the co-founder breakup (2:42) – Trying a scratch-your-own-itch project (6:27) – Unfair advantages inform another pivot (15:07) – Respecting the “emotional runway” (19:23) – Marketing insights vs. an internal BI tool (23:01) – The curse of the audience Links from the Show: Applications for TinySeed are Open Through Feb 23rd Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Hello Query 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…
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1 Episode 758 | Do Free Trials Suck?, What Moves the Needle, and More Listener Questions (with Derrick Reimer) 45:09
45:09 Play Later Play Later Lists Like Liked45:09
Play Later Play Later Lists Like LikedIn episode 758, Rob Walling is joined by Derrick Reimer to tackle a variety of listener questions. They discuss strategies for entering a market with established competitors, including how to position your product without directly attacking rivals. They also reflect on the challenges of free trials, weighing the pros and cons of extending trial periods versus incentivizing onboarding. Episode Sponsor: Most marketing agencies promise growth but never move the needle. But Corey Haines and the team at Conversion Factory? They know how to deliver results. Derrick Reimer said that "Under Corey's marketing leadership, SavvyCal broke into the market with a successful launch and steadily grew to several thousand customers." And Eunice Koo of Less Annoying CRM said that their “first A/B test with Conversion Factory, delivered a 20% increase in visitor to trial conversions within the first two months.” Imagine having a senior copywriter, designer, and web developer at your disposal to turn every marketing idea into a reality. Head to conversionfactory.co and mention this podcast when you book a call for $1,000 off your first month. Topics we cover: (1:18) – How to launch a SaaS product in a market with an established competitor (6:21) – Do I call out competitors by name? (14:24) – How do you really identify what moves the needle in your Saas? (19:59) – Breaking down the “one thing” (23:32) – Selling and marketing SaaS before building (30:36) – What is the goal of your free trial? (39:10) – On the fence between B2B, B2C Links from the Show: TInySeed Applications are open until Feb 23rd Derrick Reimer (@derrickreimer) | X Derrick Reimer (@derrickreimer.com) | Bluesky SavvyCal 757 | TinySeed Tales s4e5: Founder Breakups, Crushing Failures, and the Future TinySeed MicroConf Connect SaaS Institute Start Marketing The Day You Start Coding by Rob Walling Start Small Stay Small by Rob Walling 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…
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1 Episode 757 | TinySeed Tales s4e5: Founder Breakups, Crushing Failures, and the Future 15:24
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Play Later Play Later Lists Like LikedIn this episode of TinySeed Tales, Rob Walling chats with Colleen Schnettler, co-founder of Hello Query, as she navigates the complexities of her startup journey. After a challenging period with her co-founder Aaron, Colleen reflects on their decision to part ways and the emotional toll it has taken on her. She shares her feelings of crushing failure, the uncertainty of moving forward alone, and the realization that their initial product vision may not align with market needs. Topics we cover: (0:49) – Colleen and Aaron make a tough decision (4:09) – Voice memo, “Crushing Failure” (7:59) – What if you hadn’t raised money? (11:44) – Colleen weighs her remaining options Links from the Show: Applications for TinySeed are Open Through Feb 23rd Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Hello Query 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…
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1 Episode 756 | Why Great Product Management Is Critical for Your Startup 43:10
43:10 Play Later Play Later Lists Like Liked43:10
Play Later Play Later Lists Like LikedIn episode 756, Rob Walling interviews Brendan Fortune, Director of Product Management at Customer.io, to explore the skills and frameworks for effective product management. Brendan shares his journey and discusses the importance of understanding customer behavior to drive product decisions. They delve into the concept of the flywheel and how it can be leveraged to enhance user success and optimize pricing strategies. Topics we cover: (2:46) – What does a product manager do? (10:36) – When should a SaaS company designate a full time product manager? (15:33) – Pricing and and creating a flywheel (22:41) – Deciding on your “fair” value metric (30:01) – Pricing experimentation in the early days Links from the Show: Applications for TinySeed Spring 2025 are Open! Invest in TinySeed Ask a product question on Startups For the Rest of Us Brendan Fortune | LinkedIn Customer.io Product Flywheel + Pricing + Org Strategy (Miro) Your Pricing is WRONG (even Sam Altman Made This Mistake) 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…
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1 Episode 755 | TinySeed Tales s4e4: Customer Interviews + Pivoting 15:47
15:47 Play Later Play Later Lists Like Liked15:47
Play Later Play Later Lists Like LikedIn this episode of TinySeed Tales, Rob Walling checks in with Colleen Schnettler, co-founder of Hello Query, as she shares the latest developments in her startup journey. Colleen shares the insights gained from recent customer interviews that led to a significant pivot in their product strategy. Hello Query is now focused on embedding custom reporting features within other SaaS applications and Colleen reflects on balancing product quality with minimal v1 features. Her excitement is building to get their solution into users' hands. Topics we cover: (1:32) – Digging into customer interviews (3:54) – Filtering out the noise to achieve confidence (5:31) – Other competitors in the space (8:53) – How Colleen prepares for and sources customer conversations (12:11) – Is the technical implementation coming along? Links from the Show: Invest in TinySeed Episode 748 | The Ins and Outs of Startup Investing Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Hello Query 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…
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1 Episode 754 | Broken Freemium, SaaS Plateaus, and More Listener Questions (A Rob Solo Adventure) 25:22
25:22 Play Later Play Later Lists Like Liked25:22
Play Later Play Later Lists Like LikedIn episode 754, join Rob Walling for a solo adventure as he tackles listener questions on a variety of topics. He discusses strategies for converting free users to paid customers, the implications of AI advancements on the SaaS landscape, and how to navigate platform risks when larger players enter your market. Rob also shares insights on breaking through growth plateaus. Topics we cover: (3:12) – When in doubt, don’t try freemium (6:44) – Different levers you can pull to make freemium work (8:53) – How will SaaS be affected by the exponential growth of AI? (14:09) – Big players launching features is a form of platform risk (17:24) – Should I spin out a portion of my product into a new product? (20:05) – Thinking through plateaus in your business growth Links from the Show: MicroConf Connect Applications are open through Feb 5th Ask a Question on Startups For the Rest of Us TinySeed Episode 663 | 5 Insights SaaS Founders Should Know About A.I. (Ignore at Your Peril) Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure) 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…
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1 Episode 753 | TinySeed Tales s4e3: Co-Founder Conflicts + Renaming a Business 23:10
23:10 Play Later Play Later Lists Like Liked23:10
Play Later Play Later Lists Like LikedIn this episode of TinySeed Tales, Rob Walling reconnects with Colleen Schnettler, co-founder of Hammerstone, as she shares the latest developments in their startup journey. Colleen opens up about the emotional challenges of co-founder conflicts with Aaron, highlighting the importance of communication and alignment in their partnership. They also discuss the significant pivot from their initial product offering to the newly rebranded Hello Query, a SaaS solution focused on internal reporting for teams. Topics we cover: (0:59) – Breaking up with a co-founder (7:39) – How could this conversation have been different? (9:49) – Navigating a major pivot (14:37) – Changing the name (16:56) – Getting closer to finding product-market-fit (19:39) – Competing in a competitive market Links from the Show: SaaS Institute TinySeed Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Aaron Francis (@aarondfrancis) | X Aaron Francis (@aaronfrancis.com) | Bluesky MicroConf Recap, Episode 59 – The Hammerstone Podcast Hello Query 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…
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In episode 752, Rob Walling interviews Lars Lofgren to discuss the current state of SEO. Lars shares insights on how SEO has drastically changed, especially with the rise of AI and the volatility brought on by Google’s evolving algorithm. They cover the challenges of ranking for terms, the impact of AI content, and the rise of "parasite SEO." Topics we cover: (2:16) – SEO traffic that generates $7.2M annual revenue (4:54) – Changes in Google’s algorithm (9:46) – How to approach SEO as a bootstrapper (15:45) – SEO has changed considerably (19:48) – AI and SEO (25:54) – The advent of AI Overviews (31:19) – Parasite SEO and the importance of brands Links from the Show: Get Your Tickets for MicroConf US by Jan 31st Larslofgren.com Lars Lofgren (@LarsLofgren) | X Lars Lofgren at MicroConf TinySeed.com 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…
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1 Episode 751 | TinySeed Tales s4e2: From Developer to Manager 30:34
30:34 Play Later Play Later Lists Like Liked30:34
Play Later Play Later Lists Like LikedIn this episode of TinySeed Tales, Rob Walling catches up with Colleen Schnettler, co-founder of Hammerstone, about the progress her team has made since their initial check-in. Colleen describes the tough decision to focus on one product stack, and their recent pivot toward building a reporting MVP. They also discuss Colleen’s shift into a more managerial role. Topics we cover: (2:10) – Motivations behind building additional functionality (7:07) – Repositioning the reporting dashboard (10:08) – Focusing in on the successful part of the product (14:30) – How shifting focus affects the team dynamic (16:19) – ”Hiring is horrible” (22:20) – What has management been like? (26:11) – Growing as a manager Links from the Show: Invest with TinySeed Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Refine by Hammerstone Hello Query Buy Back Your Time by Dan Martell Never Split the Difference by Chris Voss, Tahl Raz 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…
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1 Episode 750 | Making Your First Hire, Testing Prices, And More Listener Questions (with Laura Roeder) 36:28
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Play Later Play Later Lists Like LikedIn episode 750, Rob Walling is joined by Laura Roeder, founder of Paperbell, to answer intermediate listener questions. They discuss making your first hire with limited funds, testing pricing models with existing customer bases, and more. Laura also provides some great advice on content marketing, drawing from her past experience at MeetEdgar. Topics we cover: (3:14) – Building a team before you can afford your first, full time hire (11:11) – Testing pricing with existing customer bases (19:00) – What type of content should you focus on? (25:20) – Growing a pipeline of leads with limited resources (31:00) – Who are your 100 best customers? Links from the Show: SaaS Institute TinySeed TinySeed Tales is Back: S4E1 Lauraroeder.com Laura Roeder (@lauraroeder.bsky.social) | Bluesky Paperbell Episode 473 | Managing Annual Subscriptions, Low-price vs. High, Being a Non-Developer Founder, and More Listener Questions with Laura Roeder Exactly How I Cold Emailed My Way to A Life-Changing Exit (And You Can Too) by Laura Roeder The SaaS Playbook Buy Back Your Time by Dan Martell If I Started SaaS in 2024, Here’s My B2B Content Strategy for $1M ARR The Ultimate Sales Machine by Chet Holmes 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…
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1 Episode 749 | TinySeed Tales s4e1: Introducing Hammerstone.dev 26:08
26:08 Play Later Play Later Lists Like Liked26:08
Play Later Play Later Lists Like LikedWelcome to Season 4 of TinySeed Tales, where we follow the founders of one SaaS startup throughout a few years as they share their struggles, victories, and failures. In the first episode of Season 4, Rob introduces us to Colleen Schnettler, the cofounder of Hammerstone. Colleen is a self-taught Rails developer, and this season will follow how Hammerstone eventually becomes Hello Query – an AI-powered chatbot that runs custom reporting on your data. Colleen is one of 27 startup founders from TinySeed’s Fall 2022 accelerator batch. Topics we cover: (2:16) – TinySeed Tales Season 4 with Colleen Schnettler (3:57) – Custom reporting in Laravel and Rails (7:05) – Becoming an “atypical founder” (14:11) – Entrepreneurship as a military spouse (16:17) – Motivations for joining TinySeed (19:15) – A recent low point, and high point in the business (25:00) – Big plans and risky moves ahead Links from the Show: TinySeed Applications open on February 10th Colleen Schnettler (@leenyburger) | X Colleen Schnettler (@leenyburger.bsky.social) | Bluesky Refine by Hammerstone Hello Query Software Social Podcast TinySeed Tales | Season 1 | Castos TinySeed Tales | Season 2 | Gather TinySeed Tales | Season 3 | Cloudforecast 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…
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1 Episode 748 | The Ins and Outs of Startup Investing 38:43
38:43 Play Later Play Later Lists Like Liked38:43
Play Later Play Later Lists Like LikedIn episode 748, Rob Walling sits down with Einar Vollset, co-founder of TinySeed, to discuss the ins and outs of startup investing. They explore the differences between VC and angel investing, the importance of deal flow, and the challenges of valuation. Rob and Einar also highlight how TinySeed’s approach differs from traditional VC, including their focus on capital efficiency and why it’s been working for ambitious B2B SaaS companies. Topics we cover: (2:37) – The stigma of bootstrapper funding is waning (6:44) – What success looks like in venture funding (10:45) – Breaking down the math and deal flow (17:54) – How valuations work (26:21) – Keeping optionality (29:58) – Evaluating markups (35:18) – Raising TinySeed’s next fund Links from the Show: MicroConf Connect Applications open until January 15th TinySeed Invest with TinySeed Einar Vollset (@einarvollset) | X Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics Discretion Capital How To Invest In Startups by Sam Altman 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…
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1 Episode 747 | Evolving SaaS Customer Success Over 7 Years (with Jane Portman) 35:54
35:54 Play Later Play Later Lists Like Liked35:54
Play Later Play Later Lists Like LikedIn episode 747, Rob Walling interviews Jane Portman, co-founder of Userlist, to discuss the evolution of their SaaS customer success strategy. Jane shares the four stages of Userlist’s customer success journey, from the early days of trial and error to implementing done-for-you services. They also discuss the challenges of customer onboarding for complex products. Topics we cover: (2:20) – How customer success works at Userlist (5:27) – Dealing with upfront onboarding friction (9:51) – Stage 1, “young and naive” (12:16) – Stage 2, “hire someone” (19:06) – Stage 3, “done for you services” (25:47) – Leveraging the Userlist blog (29:26) – Stage 4, “developing your own frameworks” Links from the Show: SaaS Institute TinySeed Jane Portman (@uibreakfast) | X Jane Portman (@uibreakfast.com) | Bluesky Userlist Episode 471 | Fighting to Gain Traction in a Crowded Space with Jane Portman of Userlist Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure) Crossing the Chasm by Geoffrey A. Moore Userlist Closes a Pre-Seed Round with 21 Angel Investors SaaS Email Marketing Strategy: Everything You Need to Know 20+ “Invite Your Team” Email Examples Atomic Emails: Our Proven Method for Writing Email Campaigns 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…
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Startups For the Rest of Us
1 Episode 746 | 9 Startup Predictions for 2025 22:25
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Play Later Play Later Lists Like LikedIn episode 746, Rob Walling looks ahead to 2025 with nine startup predictions, exploring trends in no-code tools, search, autonomous vehicles, AI, and an increase in platform risk for bootstrapped founders. Topics we cover: (1:52) – Carrying forward predictions from 2024 (3:09) – Search volume for Google organic SEO (6:34) – Ads in AI interfaces (7:50) – Google’s revenue drops, bootstrapper opportunities (10:07) – “AI” use in H1’s (14:01) – Self-driving taxis (19:28) – Platform risk intensifies Links from the Show: Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret Episode 697 | 7 Predictions for SaaS Bootstrappers in 2024 Episode 725 | SEO in the Age of AI, Freemium, When Brand Becomes Important, and More Advanced Listener Questions (with Ruben Gamez) LINKLO TinySeed Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure) 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…
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Startups For the Rest of Us
1 Episode 745 | Reflecting on 2024: Revisiting My Predictions, The Best Episodes, My Favorite Frameworks, and More (A Rob Solo Adventure) 27:21
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Play Later Play Later Lists Like LikedIn episode 745, Rob Walling goes solo to reflect on 2024. He revisits key concepts and frameworks introduced on the podcast, including the 2-20-200 Validation Framework, Orthogonal SaaS, and the eight levels of platform risk. Rob also looks back at his top five favorite episodes and reviews his predictions for the year—some of which came to pass, and others that didn’t. Topics we cover: (2:05) – Looking back at concepts and frameworks from past 12 months (8:50) – Rob’s 5 favorite episodes (11:56) – Reflecting on 2024 accomplishments (19:47) – TinySeed Tales Returns in 2025 (21:18) – Evaluating 2024 predictions Links from the Show: The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea” MicroConf YouTube Channel Episode 706 | 2/20/200 Validation, Prior Art, and Designing by Committee (A Rob Solo Adventure) TinySeed Vertical SaaS vs Horizontal SaaS - Which is More Profitable? Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure) The SaaS Playbook Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit Episode 706.5 | Rethinking My Most Common Advice Episode 729 | 9 Things I’ve Learned Investing in 170+ SaaS Companies Episode 709 | The 7 Greatest Investments of My Life Episode 694 | 2023 In Review: Amazing Growth & Fighting Burnout How Ben Chestnut Bootstrapped Mailchimp to a $12 Billion Exit MicroConf New Orleans 2025 Start Small, Stay Small by Rob Walling Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret TinySeed Tales 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…
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Startups For the Rest of Us
1 Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics 33:57
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Play Later Play Later Lists Like LikedIn episode 744, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. They cover the recent rise of Bluesky, kicking off a 4-figure bet between Tracy and Einar. Then they discuss TinySeed’s third fund, YC Combinator backing competitors, dealing with imposter syndrome, and finally government involvement in banning social media. Topics we cover: (1:49) – Will Bluesky survive and thrive? (9:07) – The bet on Bluesky growth (13:46) – TinySeed is raising a third fund (17:25) – Y Combinator backs duplicates (22:18) – Dealing with Imposter Syndrome (27:46) – Australia's social media ban Links from the Show: The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea” Invest in TinySeed Rob Walling (@robwalling.com) | Bluesky TinySeed (@tinyseed.com) | Bluesky Tracy Osborn (tracymakes) (@tracyosborn.com) | Bluesky Einar Vollset (@einarvollset) | X Y Combinator often backs startups that duplicate other YC companies, data shows Procrastination and the Fear of Not Being 'Good Enough' by Swapnil Chauhan Startup Founders, Do THIS to Beat Imposter Syndrome Australia proposes 'world-leading' ban on social media for children under 16 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…
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Startups For the Rest of Us
1 Episode 743 | How to Sell Your Business Without Regret 36:42
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Play Later Play Later Lists Like LikedIn episode 743, Rob Walling and Dr. Sherry Walling read the first chapter of their new book, Exit Strategy: The Entrepreneur’s Guide to Selling Your Company Without Regret. They discuss the emotional and psychological challenges of selling a business, and why it’s often harder than founders expect. They offer insights on how to prepare for a sale, protect your mental health, and how to best navigate this major life change that few others understand. Back the book on Kickstarter Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io . For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too. Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.” Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer. To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups . Topics we cover: (1:49) – Exit Strategy Introduction (6:56) – Exits are complicated (11:16) – One of the hardest things you’ll ever do (15:57) – Your business is your baby (18:35) – Entering the unknown (26:49) – Six factors that shape how you feel about an exit (31:03) – Making it real Links from the Show: Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret Back the book on Kickstarter MicroConf Connect Applications Close Today, December 10th Rob Walling (@robwalling) | X Dr. Sherry Walling (@sherrywalling) | X The SaaS Playbook Built to Sell by John Warrillow Touching Two Worlds by Dr. Sherry Walling The Entrepreneur’s Guide to Keeping Your Sh*t Together by Sherry Walling, PhD, Rob Walling 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…
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Startups For the Rest of Us
1 Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure) 28:21
28:21 Play Later Play Later Lists Like Liked28:21
Play Later Play Later Lists Like LikedIn episode 742, Rob Walling goes solo to explore normalizing doing hard things and facing your biggest threats. He also discusses a framework for founders looking to scale without cutting corners – making things work, making them right, and then making them fast. Exit Strategy Kickstarter ends on December 12! Topics we cover: (2:39) – Normalizing doing hard things (6:54) – The “hard things” in your startup (10:27) – Walking into the storm (16:21) – ”Make it work, make it right, make it fast” (22:04) – Building your “Founder Gut” (25:42) – Think in years, not months Links from the Show: Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret MicroConf Masterminds Applications Close on December 4th Rob Walling (@robwalling) | X Dr. Sherry Walling (@sherrywalling) | X The Comic Lab Podcast The SaaS Playbook The Stair Step Method of Bootstrapping This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy 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…
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Startups For the Rest of Us
1 Episode 741 | What Actually is Product Led Growth? (with Wes Bush) 31:48
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Play Later Play Later Lists Like LikedIn episode 741, Rob Walling talks to Wes Bush, CEO and Founder of ProductLed, about the nuances and misconceptions of product-led growth. Wes debunks common myths and explains how companies can leverage their product to drive user acquisition, engagement, and growth. They dive into a real-world example and explore how founders can avoid the trap of thinking the product will “sell itself” while contrasting PLG and sales-led strategies. Episode Sponsor: Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io . For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too. Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.” Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer. To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups . Topics we cover: (2:01) – Defining product-led growth (6:07) – Are users able to get value for free? (11:38) – Hybrid: both product-led and sales-led (14:52) – Determining the main outcome of your free model (19:23) – Misuse of the PLG terminology (22:00) – The benefits of PLG over sales-led growth (24:08) – Workshopping SavvyCal’s product-led strategy Links from the Show: Mastermind Applications are open until December 4th Wes Bush (@wes_bush) | X ProductLed (@productled) | X ProductLed Product-Led Growth: How to Build a Product That Sells Itself by Wes Bush The Product-Led Playbook: How to Unlock Self-Serve Revenue and Dominate Your Market (With a Tiny Team) by Wes Bush Free Audiobook of The Product-Led Playbook Product-Led Onboarding by Ramli John TinySeed SparkToro SavvyCal 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…
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Startups For the Rest of Us
1 Episode 740 | My New Book! The Entrepreneur's Guide to Selling Your Business Without Regret 29:49
29:49 Play Later Play Later Lists Like Liked29:49
Play Later Play Later Lists Like LikedIn episode 740, Rob Walling speaks with Dr. Sherry Walling about their new book, "Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret." They explore the emotional, psychological, and practical aspects of selling a business, emphasizing the universal challenges entrepreneurs face. The book draws on both Rob and Sherry’s unique experiences that they’ve shared with countless founders throughout their careers. Exit Strategy is now live on Kickstarter! Topics we cover: 2:01 – Not just a book for those selling SaaS 8:13 – The Kickstarter for the book is live today 12:16 – Before, during, and after the exit 14:55 – Why exiting is so hard 20:39 – Life after the exit 25:10 – A few traps await founders shortly after exit 26:24 – What do you do with a big pile of money? Links from the Show: MicroConf Remote Goes Live November 20th! Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret Rob Walling (@robwalling) | X Dr. Sherry Walling (@sherrywalling) | X Zen Founder Zen Founder Podcast The SaaS Playbook The Art of Selling Your Business by John Warrillow Before the Exit by Dan Andrews Finish Big by Bo Burlingham MicroConf TinySeed Touching Two Worlds by Dr. Sherry Walling 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…
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