Episode 801 | Competing Against Incumbents, Technical Co-Founders, Trademarks, and More Listener Questions with Derrick Reimer

24 snips

Oct 7, 2025

In this talk, Derrick Reimer, founder of SavvyCal, shares valuable insights on startup strategies. He explains how to effectively compete against well-funded rivals by finding their weaknesses and focusing on niche markets. The duo also discusses the dilemma of pivoting versus persevering and how to evaluate whether a technical co-founder is essential for your success. Additionally, they demystify the concept of 'good churn' vs. 'bad churn' in SaaS and when it's sensible to pursue trademarks, highlighting practical approaches for bootstrapped founders.

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ADVICE

Pick A Niche Incumbents Avoid

Focus on niching where a funded incumbent can't comfortably go and position specifically for that subset.
Charge premium for differentiated, quantifiable service like personalized onboarding or better support.

ADVICE

Mine Competitor Reviews For Openings

Research competitor weaknesses via customers, ex-employees, and one-star reviews to find positioning angles.
Use those concrete flaws to craft messaging that explains how you're different and better for a subset.

INSIGHT

Other Startups Are Your Biggest Threat

The real danger to startups is other hungry startups, not slow incumbents.
Competing against similar, well-funded startups is tougher because they move fast and overlap with you.

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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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Topics we cover:

(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?

Links from the Show:

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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