Startups For the Rest of Us

Rob Walling
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow 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.

  1. 4 DAGE SIDEN

    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 we cover:  (1:49) – Crossing $500k ARR and building personal health habits (5:36) – The big levers behind OutboundSync’s growth (6:39) – Laser tag, not hotel happy hours (13:01) – Deciding not to raise more funding (for now) (16:25) – An overbuilt tech stack  (17:57) – Competitors, copycats, and growing a brand (19:06) – The next chapter for OutboundSync (23:29) – Ambition, TinySeed, and channeling energy (25:14) – Harris’s advice for founders still grinding Links from the Show:  Invest in TinySeed Fund Three Coaching Call Bonus OutboundSync Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

    29 min.

  2. 6 DAGE SIDEN

    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 stagnant years to discovering their killer differentiation, Colin's journey is a masterclass in patient iteration, finding product-market fit the hard way, and why sometimes the most boring infrastructure businesses make the best SaaS companies. Episode Sponsor: You’ve probably heard that ChatGPT can do all of your marketing. But that’s nonsense unless your strategy is blindly following tired, recycled, outdated strategies.  If you care about systematically creating a marketing engine that converts, not just throwing spaghetti at the wall to see what sticks, you need real humans who actually understand positioning, persuasion, and modern customer acquisition playbooks.  That’s Conversion Factory. They’re a SaaS marketing and design agency that have worked with over 50 startups, including several TinySeed companies.  Book a call at conversionfactory.co and mention this podcast for $1,000 off your first month. And if you’re at MicroConf Europe next week, make sure to connect with Corey Haines in the hallway track.  Topics we cover:  (3:08) – How StatusGator detects outages (and why users are part of the signal) (6:23) – From side project to SaaS: the early days of building StatusGator (8:46) – Shifting the ICP: Why developers weren’t the buyers (11:44) – SEO as the engine behind thousands of trials (17:00) – Hitting early MRR milestones and hiring the first marketer (25:12) – How TinySeed funding unlocked a full product redesign (32:05) – Building a dual funnel to boost ACV and win enterprise deals (38:00) – Advice for other SaaS founders playing the long game Links from the Show:  Invest in TinySeed Fund Three MicroConf Mastermind Matching - Applications open until September 24th StatusGator Colin Bartlett | 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

    42 min.

  3. 18. SEP.

    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 business while raising a family. Topics we cover:  (2:28) – From $20k to $35k MRR in three months (2:53) – The bets that moved the needle (4:56) – Infinite runway, SOC 2 wins, and building trust (8:29) – Saying no to good ideas with limited bandwidth (10:00) – Decision-making, value-driven growth, and agency DNA (13:14) – Should Harris raise more funding or stay focused? (15:52) – Why boring “pipes” matter in an AI world (20:25) – Trade-offs, mindset, and building for scale (25:35) – Hiring a sales coach and focusing on what works (27:52) – Balancing startup stress with parenting Links from the Show:  SaaS Institute Coaching Call Bonus OutboundSync Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

    30 min.

  4. 16. SEP.

    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 fundamentals. Episode Sponsor: Is your engineering team stretched too thin? Gearheart provides growing companies with AI-powered engineering talent that ships 2 times faster.  CTOs and engineering managers trust them to deliver critical features end-to-end with minimal oversight, whether it's fixing scaling failures, broken integrations, or system instability.  With 13 years of experience building sophisticated B2B platforms, they plug in fast and deliver results. They've helped build platforms like SmartSuite, which has scaled to thousands of organizations including industry giants like Capital One. Book your free strategy session at gearheart.io and mention this podcast to get 20% off discovery or embedded engineers for your team. That's gearheart.io. Topics we cover:  (2:20) – Why marketing is harder than ever, and what’s changed (3:40) – The Dunning-Kruger Effect  (11:30) – Marketing is not just convincing someone to buy what you've built. (16:30) – Validating vs. throwing dice at a wall (20:03) – Is there a ‘one right way’ to grow a business? (25:00) – Be careful who you listen to Links from the Show:  MicroConf Events MicroConf Mastermind Matching 75+ SaaS Marketplaces  The SaaS Playbook TinySeed Rob Walling (@robwalling) | 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

    30 min.

  5. 11. SEP.

    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. Harris shares the bets that moved the needle, including Salesforce, SOC 2, and what hidden demand taught him about building integrations before anyone asked. Topics we cover:  (1:32) – Crossing $20k MRR and aiming for $30k (6:29) – The Salesforce bet (8:17) – Runway, burn, and pricing upmarket (10:34) – Raise capital or keep bootstrapping (15:03) – SOC 2 as a sales unlock (20:11) – Marketplace credibility and AppExchange (22:05) – Hidden demand for Salesforce (26:11) – The push to $30k and parity Links from the Show:  Invest in TinySeed Fund 3 Coaching Call Bonus MicroConf Events OutboundSync Harris Kenny | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

    28 min.

  6. 9. SEP.

    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 surge that changed everything, and the emotional ride that led to a life-changing exit. Episode Sponsor: AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead. With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more. You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business. There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world.  Try it free at ahrefs.com/awt. Topics we cover:  (3:47) — From podcast listener to SaaS founder (7:59) — The role of luck, timing, and the pandemic in growth (18:37) — A birthday gift becomes a product (23:54) — Charging early and surviving slow growth (30:47) — From $1k a month to 80k daily users (39:58) — Support load, stress, and the edge of burnout (48:58) — Deciding to sell (and why timing mattered) (52:57) — Life after the exit: slowing down and finding balance Links from the Show:  TinySeed – Applications close tonight! MicroConf Connect – The community for SaaS founders The SaaS Playbook  Memento (formerly VidHug) Zamir Khan (@zam1rkhan) | X Zamir Khan  | LinkedIn If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

    56 min.

  7. 4. SEP.

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

    27 min.

  8. 2. SEP.

    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) deal. Episode Sponsor This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up. Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at. Book your free strategy session at gearheart.io and mention Startups for the Rest of Us to get 20% off discovery, validation, or prototyping services. Topics we cover:  (3:12) – TinySeed returns Fund One (9:40) – GPT-5: Upgrade or letdown? (19:19) – Are we in an AI bubble? (24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees (31:06) – The bigger problem: Are startups forgetting to share the upside? (40:05) – Lifestyle vs. Ambitious Bootstrapping Links from the Show:  TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd TinySeed SaaS Accelerator - Applications are Open! Invest in TinySeed MicroConf SaaS Institute Discretion Capital  Einar Vollset | LinkedIn Einar Vollset (@einarvollset) | X Tracy Osborn  Tracy Osborn | LinkedIn Tracy Osborn (@tracymakes) | X If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you! Subscribe & Review: iTunes | Spotify

    46 min.
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Om

The original podcast for bootstrapped and mostly bootstrapped startups, this show follow 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.

Oplysninger

  • Skaber
    Rob Walling
  • Aktive år
    2010 - 2025
  • Episoder
    329
  • Vurdering
    Ikke anstødeligt
  • Copyright
    © 2025 Startups For the Rest of Us
  • Websted for serie
    Startups For the Rest of Us

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