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 between “good churn” and “bad churn” especially when customers fall outside your ICP.

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• (3:35) – Competing with well-funded incumbents
• (12:47) – Should you focus on competitors or customers?
• (20:20) – Pivot, press on, or move on: how to decide
• (29:09) – Finding and vetting a technical co-founder or partner
• (39:04) – When should you pursue trademarks?
• (44:24) – Is churn ever good for a startup?

• MicroConf US 2026 - Portland, Oregon - Use Promo Code ROB50 for $50 off.
• MicroConf Connect
• BIMI (Brand Indicators for Message Identification)
• 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!

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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.

• (3:46) – #1: Nuance beats absolutes
• (6:52) – #2: Make hard decisions with incomplete information
• (9:16) – #3: Avoid the classic traps
• (12:22) – #4: Don't build without real evidence
• (15:14) – #5: Marketing beats product
• (19:08) – #6: Fewer customers, better customers
• (21:01) – #7: Respect (and fear) the platform
• (24:04) – #8: Build your network, not just your audience
• (26:30) – #9: Overnight success takes a decade
• (28:45) – #10: Stack small wins
• (31:22) – #11: Be careful who you listen to
• (33:15) – #12: The hardest battles are in your own head

• MicroConf US 2026 - Portland, Oregon - Use Promo Code ROB50 for $50 off.
• Invest in TinySeed Fund Three
• SaaS Playbook
• The Entrepreneur's Guide to Keeping Your Sh*t Together
• Exit Strategy
• Episode 685 | 7 Things You Should Never Do
• Episode 700 | Playing the Long Game
• Episode 735 | The 8 Levels of SaaS Platform Risk

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!

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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.

• (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

• 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!

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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.

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• (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

• 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!

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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.

• (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

• 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!

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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.

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• (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

• 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!

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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.

• (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

• Invest in TinySeed Fund 3
• Coaching Call Bonus
• MicroConf Events
• OutboundSync
• Harris Kenny | LinkedIn

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

Subscribe & Review: iTunes | Spotify

B2C, low price point, one-time payments… not the typical recipe for a life-changing exit.

In this episode, Rob Walling talks with longtime listener Zamir Khan, founder of VidHug (now Memento). Zamir’s story broke a lot of SaaS “rules”: B2C, low price point, one-time payments, and years of slow growth. He shares how he nearly gave up, the pandemic surge that changed everything, and the emotional ride that led to a life-changing exit.

Episode Sponsor:

AI is completely changing how people discover brands and content online, and Ahrefs has built a full-blown SaaS marketing platform to help you stay ahead.

With over 15 years of real-world web data, and AI that actually understands marketing, Ahrefs helps you measure your brand presence, build authority, and monitor reputation across search, social, and AI platforms like ChatGPT, Google AIOs, Perplexity, and more.

You can also dig into what’s driving your competitors’ visibility and spot market gaps before they do, helping you create content that ranks and drive new traffic to your business.

There's no need to juggle a bunch of disconnected tools- get Ahref’s all-in-one platform to make your brand unmissable in a fast-moving world.

Try it free at ahrefs.com/awt.

Topics we cover:

• (3:47) — From podcast listener to SaaS founder
• (7:59) — The role of luck, timing, and the pandemic in growth
• (18:37) — A birthday gift becomes a product
• (23:54) — Charging early and surviving slow growth
• (30:47) — From $1k a month to 80k daily users
• (39:58) — Support load, stress, and the edge of burnout
• (48:58) — Deciding to sell (and why timing mattered)
• (52:57) — Life after the exit: slowing down and finding balance

• 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