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
• (4:00) – The Dunning-Kruger Effect
• (11:18) – Marketing is not just convincing someone to buy what you've built.
• (17:39) – Validating vs. throwing dice at a wall
• (20:10) – 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!

Subscribe & Review: iTunes | Spotify

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