Startups For the Rest of Us
The original podcast for bootstrapped and mostly bootstrapped startups, this show follows the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
Episodes
Episode 854 | How to Find Startup Ideas (Sneak Peek Chapter from My New Book)
Where do the best SaaS ideas actually come from?
In this episode, Rob reads a chapter from his new book, Idea to Traction: Stop Building SaaS Nobody Wants in the Age of AI. He walks through the five places problems tend to show up, eight strategic approaches for finding and shaping a product idea (with real examples), and when it makes sense to repli
Episode 853 | How to Become the SaaS That AI Recommends
How do you get LLMs to actually recommend your SaaS?
In this episode, Rob Walling talks with Ross Hudgens, founder of Siege Media and author of the new book Generative Engine Optimization, about how SaaS companies get recommended by ChatGPT, Gemini, and the AI tools customers now use to shop. They cover why "best X" roundups and versus articles outp
Episode 852 | Getting Big Name Customer Case Studies and More Listener Questions (with Ruben Gamez)
Should you be worried that another founder will steal your idea if you ask them for advice?
In this episode, Rob is joined by Ruben Gamez to answer four listener questions: whether reaching out to more advanced founders puts your idea at risk, how to convince big name customers to agree to a case study, what to do when a platform ecosystem (like Shop
Episode 851 | The Messy Middle of a SaaS Pivot
How do you pivot your SaaS when things aren’t working?
This week Rob talks with Nathan Tyler, founder of BlinkMetrics, about the messy, uncertain process of finding product market fit in real time. Nathan walks through why his original EOS scorecard idea didn't work, how hundreds of coffee chats led to a done for you reporting business, and why he ju
Episode 850 | How Not to Screw Up When Hiring Your first Developer and More Listener Questions (with Derrick Reimer)
How do you onboard a hire onto a codebase you built alone?
In this episode, Derrick Reimer joins Rob to tackle four listener questions. They cover hiring and onboarding your first developer as a bootstrapped founder, then move into the temptation to build features just because AI makes them cheap to ship, getting past social anxiety as a founder, and
Episode 849 | Legal Threats, AI as Platform Risk, Building Confidence, and More Listener Questions (Rob Solo)
Ever gotten a vague cease and desist from a competitor and wondered if you actually did something wrong?
This week I tackle four listener questions: how seriously to take competitor terms of service threats, whether AI is really a platform risk (or just a feature risk), how to build confidence and get past the fear of reaching out to prospects, and when
Episode 848 | What Liquid Death Can Teach Us About B2B SaaS (Rob Solo)
Does validation still matter when AI has made building software almost free?
In this solo episode, Rob breaks down the origin story of Liquid Death, the canned water company now valued at over a billion dollars, and pulls out the mental models that apply directly to B2B SaaS. He covers why ideas come from being in the arena, how founder Mike Cessario
Episode 847 | What Second Time Founders Do Differently, Pricing AI Agents, and More Listener Questions (Rob Solo)
Would you spend a year on distribution for a product that doesn't exist yet?
In this solo episode, Rob answers listener questions about how second and third-time founders think differently, from filtering a dozen good ideas down to one, to why distribution and validation matter more the second time around. He also digs into how to sell and price AI a
Episode 846 | Snail Mail, Cold Calling, Regulating Your Nervous System, and More Listener Questions (Rob Solo)
Is your nervous system sabotaging your best decisions?
In this episode, Rob mixes a solo adventure with listener questions. He answers a reader who asks why he still shows up to write, record, and build, then digs into regulating your nervous system when you have to do something that scares you. He wraps with two listener questions on direct snail ma
Episode 845 | Lifetime Deals Revisited, Building is Not the Hard Part, and Confirming an Idea is Worth Paying For (Rob Solo)
What does it take to make a lifetime deal work?
In this listener questions episode, Rob Walling revisits the lifetime pricing debate with new context from Davis Baer of Youform. He also tackles why building is rarely the hard part, how bootstrappers get shut out of startup discount programs, what to watch for when signing customer agreements ahead of
Episode 844 | Building a $1M+ ARR SaaS for Laundromats
What does it take to build a seven figure SaaS in a market almost no one thinks about?
In this episode, Rob Walling sits down with Brian Henderson, co-founder of Wash-Dry-Fold POS, to walk through the 10-year arc of building it in one of the most overlooked markets there is: laundromats. From selling other people's hardware as a scrappy reseller, to
Episode 843 | Success Patterns of $1M+ SaaS Founders
Are you building systems for your team, or are you still the system?
In this episode, Rob Walling talks with Julien Marzouk, a former SaaS founder and coach who has worked with hundreds of seven and eight figure founders over the past decade. Julien breaks down six recurring patterns he sees in founders who scale past a million, from the identity sh
Episode 842 | What is the Future of SaaS in an AI World? (Rob Solo)
Is SaaS dead now that AI can build an app in a weekend?
In this solo episode, Rob Walling gives his most definitive answer yet to the question flooding the internet: what's the future of SaaS now that AI makes it easier than ever to build and copy a product? He breaks down the four most common claims that AI will kill Saas, and explains why the real
Episode 841 | One-time Payments, Growing a Step 2 Business, Positioning, and More Listener Questions (Rob Solo)
Should you keep pouring time into a business that will probably never be huge?
In this episode, Rob Walling answers listener questions about whether to keep growing a "step two" B2C business despite platform risk, when one-time payments make sense versus subscriptions, and how to price and position a Shopify app that needs custom implementation work.
Episode 840 | 5 PM Revisited, Starting Over After Failure, Never Shipping, and More Listener Questions (Rob Solo)
What's really stopping you from shipping your product and how do you finally push through?
In this listener questions episode, Rob Walling covers a lot of ground: revisiting the 5PM framework with more opinionated guidance on pricing and market size, the right time to use vibe coding in your SaaS, why B2C apps are brutal, how to rebuild after startup
Episode 839 | The Journey Growing Help Scout to $35M ARR
What happens when a bootstrapper at heart raises $28 million and spends the next decade living with that decision?
In this episode, Rob Walling sits down with Nick Francis, the co-founder of Help Scout, to walk through the full 15-year arc of building one of the most beloved support tools in SaaS. From the cramped Techstars apartment he shared with a
Episode 838 | 6 Key Takeaways From a TinySeed Batch Kick-Off
What do 15 brand-new TinySeed founders have in common?
In this solo episode, Rob Walling shares six key takeaways from the most recent TinySeed batch kickoff in New York City. He covers why asking "why" is the most underrated founder habit, why pricing is still the biggest lever in SaaS and positioning might be the second biggest, why AI SEO is alre
Episode 837 | How Do You Learn Product? and Optimizing Your Trial Funnel (with Ruben Gamez)
How does a founder actually learn the skill of product?
In this episode, Rob Walling talks with Ruben Gamez of SignWell and Bidsketch to answer listener questions that turned into a much deeper conversation than expected. They cover why friction works well for one of Ruben's products and kills conversions on the other, how to think about trial length
Episode 836 | The 5 A.I. Moats Acquirers Value Most
Is your SaaS actually protected from AI disruption, or are acquirers walking away without even looking?
In this episode, Rob Walling talks with Einar Vollset of Discretion Capital for a front-lines SaaS M&A market report, covering how the acquisition climate has shifted since 2021, why some PE firms now require at least one AI moat before they'll
Episode 835 | The Right Way to Use AI in Your Startup Marketing
Are you using AI in your marketing because it's actually good, or just because it's fast?
In this episode, Rob Walling sits down with Taylor Hendricksen, a performance marketer who has managed tens of millions of dollars in ad spend across Meta and Google, to talk about where AI is genuinely useful and where it produces flat, mediocre output that mak
Episode 834 | Eric Ries Revisits The Lean Startup and Discusses How to Become Incorruptible
Is AI actually making your build-measure-learn cycle faster, or just making your work more average?
In this episode, Rob Walling talks with Eric Ries, author of The Lean Startup, to revisit what's held up in Lean Startup thinking 15 years on, why AI speeds up building but can't replace human learning, and what drove Eric to write his new book, Incor
Episode 833 | Success Patterns of Nobel Laureates, Developing Expertise, and From Zero to $10k (A Rob Solo Adventure)
What do Nobel Prize winners and successful bootstrappers have in common?
In this solo episode, Rob Walling shares the story of how a TinySeed company went from near-zero revenue to $10,000-$20,000 a month almost overnight, breaks down Claude Shannon's research on the habits that separated Nobel laureates from forgotten scientists, and explores why d
Episode 832 | Going Full-time, When to Pivot, Building With Young Kids, and More Listener Questions (Rob Solo)
How do you leave a $400K salary to go all in on your business?
In this solo episode, Rob Walling cranks through a backlog of listener questions on reducing risk with your startup to go full-time, when to register as a business, how to price a SaaS with seat ambiguity, when to pivot, and how to keep building when you have four kids under eight.
Wa
Episode 831 | Written vs. Verbal Ad Copy, Selling Into a Low-Awareness Market, and More Listener Questions (Rob Solo)
Should your first customer pay you, or get your product for free?
In this episode, Rob Walling answers listener questions on charging customer zero, what metrics to track for a seasonal transaction fee-based SaaS, what it really means to sell into a low-awareness market, and when freelancers help vs. hurt your bootstrapped business. He also calls in
Episode 830 | Breaking Through Plateaus, Zero-Click Marketing, and More from MicroConf 2026 (with Derrick Reimer)
What were the highlights and takeaways from MicroConf?
In this episode, Rob Walling and Derrick Reimer recap MicroConf US 2026 in Portland, Oregon. They break down the best talks from the event, including Jason Cohen on breaking through growth plateaus, Amanda Natividad on Zero-Click Marketing and broken attribution, Rob's framework for six ways to
Episode 829 | AI is Bad at Product, Top 5 Startup Success Factors, and the Beastie Boys (A Rob Solo Adventure)
Can AI really handle product decisions for your SaaS?
In this solo adventure, Rob Walling revisits the core four SaaS skills and breaks down what AI can and cannot do across Development, Sales, Marketing, and Product. He also reframes Bill Gross's top five startup success factors for bootstrappers, walks through a hilariously bad UX decision by a loc
Episode 828 | Am I Building a SaaS?, Serving Both B2C and B2B, Pricing, and More Listener Questions (Rob Solo)
Is your product actually a SaaS?
In this episode, Rob Walling tackles listener questions about what really qualifies as SaaS (and where he disagrees with ChatGPT), how to serve both solopreneurs and enterprise customers with a dual funnel strategy, layering a B2B offering on top of a B2C product, pricing a mission-driven app without gatekeeping acces
Episode 827 | The Founder's Guide to Selling Your SaaS for What It's Actually Worth
What would it mean for you to leave 60 or 70% of your company's value on the table when you sell?
In this episode, Rob sits down with Einar Vollset, co-founder of TinySeed and founder of Discretion Capital, to talk about his new book, The Definitive Guide to M&A for B2B SaaS between $2 and $20 million ARR. They dig into why private equity now dom
Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers
How do you find someone who thinks like an owner, not just a task-doer?
In this episode, Rob digs into a batch of listener questions about task level, project level, and owner level thinkers. He covers how to identify them, what they cost, where to find them, and why building a team of exceptional people creates a virtuous cycle that lifts everyone u
Episode 825 | Talking Tailwind CSS and Founder Fitness (with Adam Wathan)
What happens when AI starts competing with your open source business?
In this episode, Rob Walling sits down with Adam Wathan, co-founder of Tailwind CSS, for a candid conversation about the dramatic revenue decline that forced Tailwind Labs to lay off most of their team. Adam shares the hard lessons learned from running a business based on one-time
Episode 824 | Crowded Markets, Problem Aware, A Stolen Idea, and More Listener Questions (with Jordan Gal)
What do you do when a collaborator takes your idea and builds a competing product?
In this episode, Rob Walling is joined by fan favorite Jordan Gal to answer listener questions on some of the trickiest challenges founders face. They cover financing decisions like using debt to bridge cash flow gaps, competing in markets flooded with vibe-coded apps,
Episode 823 | Hot Take Tuesday: Is A.I. Killing B2B SaaS?, ChatGPT Ads, OpenClaw
Is AI really killing B2B SaaS, or is it just subscription software by another name?
In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into the market panic around SaaS stocks, whether AI models are actually getting better, ChatGPT's move into advertising (and Anthropic's spicy response), and the explosion of OpenClaw. They al
Episode 822 | No-code vs. A.I. Coding, SaaS Margins in the A.I. Age, and More Listener Questions (with Derrick Reimer)
Should you build your SaaS with no-code tools, or is AI coding the better path forward?
In this episode, Rob is joined by fan favorite Derrick Reimer to tackle listener questions on no-code vs. AI vibe coding, when to take small funding early vs. pure bootstrapping, whether SaaS margins will compress as AI makes building cheaper, and how to get truly
Episode 821 | How to Do Founder-Led Marketing (with Jay Clouse)
Is founder-led marketing right for your SaaS, or just a distraction?
In this episode, Rob Walling sits down with Jay Clouse, founder of Creator Science, to explore founder-led marketing. They dig into how Jay overcame his own limiting beliefs about creativity, why most SaaS founders probably shouldn't pursue content creation, and how to evaluate whet
Episode 820 | When to Quit Your Day Job, A.I. Feasibility Risk, and More Listener Questions (Rob Solo)
When do you finally quit your day job and go all-in on your startup?
In this solo episode, Rob Walling answers listener questions about when it’s worth taking funding to speed up your path to full-time, how to think about equity when a co-founder joins late, and whether A.I. is shifting startup risk from market risk to feasibility risk. He also break
Episode 819 | QSBS, Exit Multiples, How to Learn Marketing, and More Listener Questions (Rob Solo)
Could your business structure quietly cost you millions when you sell?
In this solo episode, Rob Walling answers listener questions about when QSBS might justify a C Corp (vs. staying an S Corp or LLC), why SaaS exits are often discussed in ARR multiples rather than EBITDA, and how the profitability/growth tradeoff impacts valuation. He also shares t
Episode 818 | What Does It Take to Be Successful? with Russ Walling
Is perfectionism quietly sabotaging your career or startup dreams?
In this episode, Rob Walling talks with his brother, Russ Walling, about the mindset and habits that shape long-term success from overcoming perfectionism to building resilience and learning to make tough calls without all the answers.
They discuss how growing up with a shared emph
Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
How would a 2x unicorn founder build his next startup with AI?
In this episode, Rob Walling sits down with Jason Cohen, founder of SmartBear and WP Engine, to talk about building billion-dollar businesses, the future of AI for founders, and what makes small companies thrive even when the odds are stacked against them.
They dig into the early days
Episode 816 | Developing an Editorial Eye, The Right Kind of Stubborn, and The Power of Focus (A Rob Solo Adventure)
Have you ever pushed so hard on an idea that you missed the signal to change direction?
In this solo episode, Rob Walling covers a wide range of topics and dives into three areas every founder should master: how to develop an editorial eye (or “taste”), the difference between persistence and obstinance, and why focus, not diversification remains the
Episode 815 | Unexpected Skills Your Day Job Can Teach You About Entrepreneurship (Rob Solo)
Can your 9-to-5 job secretly prepare you to be a founder?
In this solo episode, Rob Walling shares 11 unexpected lessons from his own day jobs, from courier to electrician to engineering manager, and how each role quietly taught him skills that shaped his success as a SaaS founder. He dives into the value of curiosity, self-education, and learning to
Episode 814 | How to Beat a Venture-Backed Competitor (with Laura Roeder)
What’s it take for a bootstrapped SaaS to beat a competitor with $10M in venture funding?
In this episode, Rob Walling talks with Laura Roeder, founder of Paperbell, about how her lean, fully-bootstrapped team outlasted and outperformed a VC-funded rival. They discuss what the venture-backed company got wrong, how Paperbell focused on the right cust
Episode 813 | SaaS Predictions for 2026 (+ Reflections on 2025)
How will AI, SEO, and market shifts change SaaS next year?
In this solo episode, Rob Walling revisits his predictions for 2025, what he got right, what he totally missed and shares nine new predictions for 2026. He reflects on trends shaping bootstrapped SaaS, from the rise of AI-first startups to the challenges facing horizontal SaaS founders.
I
Episode 812 | The 2025 State of TinySeed
After funding 210+ B2B SaaS companies, what patterns have emerged?
In this episode, Rob Walling shares the 2025 State of TinySeed, from its first fund in 2018 to a global portfolio of over 210 B2B SaaS companies. He reflects on TinySeed’s growth, what the data reveals about today’s founders, funding trends, and the rise of AI-first startups.
Topic
Episode 811 | When to Delegate the "Core Four SaaS Skills," Freemium Retention Rates, and More Listener Questions (A Rob Solo Adventure)
How do you step back from daily decisions without losing control of your SaaS?
In this episode, Rob Walling answers listener questions about when to delegate key founder skills, whether great founders can succeed with any idea, and the limits of no-code or “vibe-coded” apps.
To help answer one question, he calls up Ruben Gamez to get his insights
Episode 810 | The Best A.I. Coding Stack, Shipping Fast, and More Listener Questions (With Derrick Reimer)
How much design polish is really enough?
In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a new round of listener questions. They dig into the best AI coding stacks right now, how to ship fast without losing polish, whether AI is changing the kind of risk founders face, and when to start taking security seriously.
Episode
Episode 809 | What I Learned Diving into A.I. for 100 Days (with Craig Hewitt)
What are the can't-miss AI tools for SaaS founders?
In this episode, Rob Walling sits down with Craig Hewitt, founder of Castos, to dive deep into Craig’s “100 Days of AI” YouTube series. They discuss the lessons learned from exploring the latest AI tools for founders, why ChatGPT might not be the best option for SaaS entrepreneurs, and which AI plat
Episode 808 | A $500k "Step 1" Business, When to Consider SOC2, and More Listener Questions
Is it time to sell, autopilot, or double down on your plateaued SaaS business?
In this episode, Rob Walling tackles listener questions and shares practical frameworks for what to do when your product hits a plateau, explains why “autopilot” often leads to decline, and outlines when founders should seriously consider SOC 2 compliance. Rob also talks a
Episode 807 | The "Core Four" SaaS Skills and Knowing When You Should Find a Co-founder (A Rob Solo Adventure)
Is hiring a sales and marketing co-founder the secret sauce for technical SaaS founders?
In this solo episode, Rob Walling tackles a fresh batch of listener questions, starting with one of the most common dilemmas for technical founders: should you hire a sales and marketing co-founder or go it alone?
He introduces his “Core Four” mental model, th
Episode 806 | Bootstrapping Missive to $8M ARR Over 10 Years
Can a small team really bootstrap to $8M ARR in a crowded SaaS market?
In this episode, Rob Walling chats with Philippe Lehoux about how he and his co-founders bootstrapped Missive, a collaborative email and team inbox tool. They deep dive into landing early customers, unique horizontal positioning, content-driven growth, enterprise sales, and how to
Episode 805 | Gatekeeping vs. Paying Dues, Raw Material, and Surrounding Yourself with the Right People (A Rob Solo Adventure)
How much does your startup idea matter compared to your execution?
In this solo episode, Rob Walling covers several founder-focused topics: the difference between gatekeeping and paying your dues, why raw material beats polish, and why successful people don't mind others winning. He also shares a listener's exit story, discusses optimism in founder c
Episode 804 | Positioning, Inventing a Category, Marketing Globally, and More Listener Questions (A Rob Solo Adventure)
Can bootstrapped founders really invent a new category with AI or is it a trap?
In this solo episode, Rob Walling answers a fresh batch of listener questions covering SaaS marketing, global expansion, and strategic positioning. He shares advice on whether inventing a new product category is ever worth it and the nuances of updating your positioning a
Episode 803 | 8 Key Takeaways from MicroConf Europe 2025
What's it really like to attend MicroConf?
In this episode, Rob Walling and Laura Sprinkle, founder of Rootabl, recap MicroConf Europe 2025 in Istanbul. They discuss the MicroConf vibe, standout talks on AI, affiliate marketing, and SaaS growth, as well as the value of networking and connecting while getting outside the conference room.
Topics w
Episode 802 | Marketing Not Scaling, Where to Publish Content, and More Listener Questions (A Rob Solo Adventure)
Where’s the best place to publish if you’re starting content from scratch?
In this episode, Rob Walling flies solo, answering your questions on marketing and audience building. He covers what to do when your channels stop scaling, where to publish early on, and the "media company first" approach.
Episode Sponsor:
Are you a non-technical found
Episode 801 | Competing Against Incumbents, Technical Co-Founders, Trademarks, and More Listener Questions with Derrick Reimer
Can churn ever be good in SaaS?
In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a listener Q&A. They break down what it takes to compete with well-funded incumbents, how to decide whether to pivot or push forward, when a technical co-founder is truly necessary, the right time to think about trademarks, and the difference
Episode 800 | The 12 Commandments of Startups for the Rest of Us
What if you could get all 15 years of this podcast bundled up into one episode?
In episode 800, Rob Walling goes solo for a special milestone installment of Startups For the Rest of Us. He covers the 12 foundational commandments that shape his approach to SaaS, hard-won lessons forged from years of building, investing in, and advising startups.
T
Episode 799 | TinySeed Tales s5e6: $500k ARR!
What's next for OutboundSync?
In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here, from choosing not to raise funding (for now), to planning a laser tag event no committee would approve, to what comes next on the road to $1M.
Topics
Episode 798 | Lessons From 10 Years of SaaS Growth Without a Hockey Stick
How do you bootstrap a SaaS to $1 million+ ARR?
In this episode, Rob Walling chats with Colin Bartlett about how he and his co-founder Andy transformed a side project monitoring tool into a seven-figure ARR business that now serves as an early warning system for outages across 6,000+ services.
From nearly abandoning the product during three stagn
Episode 797 | TinySeed Tales s5e5: Should I Raise More Funding?
OutboundSync just hit $35k MRR—but the decisions are only getting harder.
In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every opportunity comes with a trade-off. They explore the tension between raising funds you don't need, staying focused when good ideas keep coming, and building a
Episode 796 | Marketing Isn't Easy?, How to Grow Your Company, and Be Careful Who You Listen To (A Rob Solo Adventure)
What if your SaaS isn’t growing because of the product, not the marketing?
In this solo adventure episode, Rob Walling unpacks why SaaS marketing feels harder than ever and why most advice out there will waste your time. He shares how he’d approach things if growth has stalled, the questions he’d ask first, and why real progress comes from proven fun
Episode 795 | TinySeed Tales s5e4: The $20K Milestone
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. Ha
Episode 794 | From Struggling Side Project to Life-Changing SaaS Exit
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 s
Episode 793 | TinySeed Tales s5e3: Building Momentum
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
Episode 792 | Hot Take Tuesday: GPT-5 Struggles, the A.I. Bubble, and the Windsurf Debacle
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) de
Episode 791 | TinySeed Tales s5e2: Growing Pains
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,
Episode 790 | From Scrappy to Scalable: Evolving Your Role as a Founder
How can you scale yourself as a founder?
In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Vera, 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 fou
Episode 789 | TinySeed Tales s5e1: From Agency to SaaS
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
Episode 788 | Do I Need a Co-founder? And More Listener Questions (with Derrick Reimer)
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
Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
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 d
Episode 786 | Questions About Bootstrapping SaaS to a $90M Exit (with Kevin Wagstaff)
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?
Episode 785 | Choosing Between AI Products, Building Multiple Apps, and More Listener Questions (A Rob Solo Adventure)
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) –
Episode 784 | The Wealth Ladder: Six Levels of Financial Freedom
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
Episode 783 | Bootstrapping ScrapingBee to $5M ARR and an 8-Figure Exit
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, w
Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions
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 tha
Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again
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
Episode 780 | "I'll Never Sell My Company" and Other Myths Founders Tell Themselves
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 pl
Episode 779 | 10 Myths Most SaaS Founders Believe
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
Episode 778 | Pricing Pilot Projects, Niching Down, Skipping Stairsteps, and More Listener Questions (A Rob Solo Adventure)
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
Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs
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 a
Episode 776 | How Bootstrapping Led to a Life-Changing $90M SaaS Exit
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.
Topic
Episode 775 | A.I. Coding Tools, User Experience, Racking Your Own Servers, and More Listener Questions (with Derrick Reimer)
What shortcuts are actually worth taking when you're building a SaaS?
In this episode, Rob Walling and fan favorite Derrick Reimer delve into listener questions about startup development. They discuss the impact of AI coding tools on building minimum viable products (MVPs) and the importance of user experience (UX) with advice on balancing UX investm
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