Voices of Search // “Lessons from AI Startup Mistakes”
Date: February 25, 2026
Host: Jordan Cooney
Guest: Thomas Payham (CEO & Co-founder, Otterly AI)
Episode Overview
In this concise episode of Voices of Search, Jordan Cooney brings on Thomas Payham, CEO and co-founder of Otterly AI, to discuss key lessons and pitfalls from founding an AI-driven startup. The conversation zeroes in on the challenges founders face in the current AI landscape, with an emphasis on sustainable growth, hiring strategies, and finding product-market fit.
Key Discussion Points & Insights
1. The Dangers of Scaling Too Quickly
Timestamp: [02:19]
- Jordan Cooney asks Thomas about crucial mistakes founders should avoid, especially as Otterly AI was launched without external funding.
- Thomas Payham highlights that a common pitfall is “growing too quickly, hiring too quickly.”
- Rapid scaling—especially through hiring—can be tempting but is risky before confirming real product-market fit.
- He advocates for restrained, focused growth in startup early stages.
Notable Quote:
“I’m a big believer in doing things that don’t scale in the first place—and only once you’ve found product-market fit, you can scale.” — Thomas Payham [02:31]
2. The Value of Doing Things That Don’t Scale
Timestamp: [02:31]
- Thomas elaborates that successful startups often succeed by first taking a hands-on, manual approach—even in a tech-driven market.
- Founders should resist the temptation to immediately outsource or hire specialists before they personally tackle the core challenges of the business.
- This approach fosters a deeper understanding of the business and the market before leveraging scale.
Notable Quote:
“Do things that don’t scale, right?… Maybe some founders rather directly jump into hiring, spending, outsourcing without fully figuring out the whole challenge beforehand themselves.” — Thomas Payham [02:38]
3. Emphasis on Product-Market Fit
- Only after truly understanding your customer and validating the market should founders scale operations or expand teams.
- Scaling prematurely can drain resources and distract from refining the actual product or service.
Memorable Moments & Quotes
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On disciplined growth:
“You can hire a team. You can build out different functions, specialists and experts and do all of that fun part, but… only once you’ve found product-market fit.” — Thomas Payham [02:35]
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Host’s takeaway:
“Remember, the answers are always in the data.” — Jordan Cooney [03:15]
Important Segment Timestamps
- [02:19] — Jordan asks about founding mistakes and scaling
- [02:31] — Thomas shares advice on growth and doing things that don’t scale
- [03:15] — Closing remarks
Tone & Style
The conversation maintains a practical, no-nonsense tone. Thomas provides hard-earned advice from the trenches, and Jordan closes the episode with a classic data-driven reminder. The episode is concise but rich in actionable insights, especially for founders navigating the AI startup landscape.