From Exit Fatigue to Building Again & Securing $100M in Fresh Capital
When Ron Reiter sold Crosswise to Oracle, it looked like the dream outcome. In reality, it nearly broke him. Years of startup stress and post-acquisition burnout forced him to confront the emotional toll of being a founder — and what “success” actually means.
Now, as co-founder and CTO of Sentra, Ron’s built differently. He’s raised $100M+, but with a renewed focus on mental health, purpose, and balance. In this episode, Ron gets raw about anxiety, exits, and the pressure behind “making it.”
→ Watch the full episode to hear how he turned burnout into a blueprint for resilience.
Here’s what you’re in for:
01:28 - Mental Health in Entrepreneurship
02:55 - Starting the Podcast: Oracle Acquisition Journey
03:32 - The Decision to Sell Crosswise
09:29 - Navigating the Acquisition Process
22:27 - Post-Acquisition Reflections and Retention
28:26 - Market Dynamics and Strategic Decisions
30:29 - Navigating Competitive Markets
31:23 - The Catalyst for Starting Anew
32:45 - Building with Friends and Finding Happiness
35:25 - Defining the Right Role
37:31 - Raising a Monster Seed Round
42:25 - The FOMO Round and Series B Success
49:28 - Investing in Founding Teams
54:54 - Advice for Founders on Raising Money and Selling Companies
58:06 - Final Thoughts and Wrap-Up
ABOUT Ron Reiter
Ron Reiter is a serial entrepreneur and technologist best known for co-founding Crosswise, acquired by Oracle in 2016, and Sentra, a cloud data security platform that has raised over $100M. A former member of Unit 8200, Israel’s elite cyber intelligence unit, Ron brings deep technical expertise and rare emotional transparency about the highs and lows of entrepreneurship.
Get in touch with Ron:
🔗 Learn more: Sentra
🔗 Connect with Ron on LinkedIn
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