Thomas Bennett

Thomas Bennett

CEO | Board Director

About

Entrepreneurial CEO, Independent Board Director, and strategic advisor navigating the intersections of artificial intelligence, robotics, cybersecurity, and deep tech. Over a career spanning venture capital, private equity, and operating roles, I’ve warmed just about every seat at the table. My track record isn't just about the occasional home run; it’s about a relentless, high-percentage ability to get on base and drive successful outcomes. As an Executive: 9 startups, 8 successful exits (including 3 as CEO, 5 as a founding/key strategic executive), generating over $2.4B in exit value and 1 IPO.

Badges

Tastemaker
Tastemaker
Gone streaking
Gone streaking
Gone streaking 5
Gone streaking 5

Forums

•

4d ago

Have you ever increased your revenue by removing your free tier completely?

We spent six months optimizing our free plan hoping it would act as a funnel for paid conversions. Turns out it just attracted thousands of free-tier hunters who drained our support and server costs, while decision-makers assumed our product was "cheap quality." We took a deep breath and killed the free tier overnight. Support volume dropped by 60%, and MRR grew 2.5x in 45 days. Funniest part? The users who complained the loudest about losing the free plan were the ones paying $0 for 8 months straight.

How do you decide when a free plan is building your funnel vs destroying your unit economics?

•

25d ago

Day one went well. Day four went bad.

The launch itself turned out better than anticipated. Stable traffic, nice feedback, a few hundred signups. I spent the night answering all of it.

Then Thursday came and traffic was at zero level. No just low but zero. For hours. There wasn't any special plan for Thursday because all the advices which I had seen were for the launch day only.

A user uninstalled my app over a time format, and I only found out because he left a review

Got a one-star review this morning. The whole thing was one line: no 12-hour option, only 24-hour, uninstalled.

He was right. My reminders app shows times in 24-hour format and never checks what the user's phone is set to. I'm from Uruguay. Here everyone uses 24-hour. It genuinely never crossed my mind that it could be a problem.

View more