From Burnout to Bulletproof: Aaron Schwartz on Founding, Focus, and Founder Fitness

In Season 4, Episode 5 of the Turning Pro Podcast, Ben sits down with Aaron Schwartz, multi-time founder, operator, and now co-founder and president of Orita.ai, an AI-powered platform that helps brands land in inboxes, not spam folders.

Aaron’s story hits different. He’s lived through brutal founder burnout, navigated messy startup exits, and advised dozens of companies before diving back into full-time building. Orita wasn’t even his idea. It started with two machine learning engineers who didn’t know how good they were. But once Aaron saw the potential, he went all in.

This episode dives deep into the real work behind fundraising, founder-market fit, and scaling smart. Aaron opens up about what he got wrong the first time around, why early-stage teams need to embrace chaos, and how great founders balance ambition with humility.

Listen to Season 4, Episode 5 on Apple Podcasts, Spotify, or YouTube.

10 Lessons from Aaron Schwartz on Going Pro (Again)

1. Your Co-Founders Matter More Than You Think
   Aaron joined Orita after advising the two technical co-founders. It only worked because he loved the people and the problem they were solving.
   

2. Build Where You Create Leverage
   He doesn’t take advisory gigs for cash. Equity forces alignment and long-term thinking, and he only says yes when he truly enjoys working with the founder.
   

3. Founder-Life Balance Doesn’t Exist, But Founder Fit Does
   Aaron chose a startup that matched the season of his life: technical co-founders, a clear customer pain, and work that felt energizing.
   

4. Don’t Fundraise Unless You Have Real Conviction
   Most founders raise too early. Aaron’s test? “If I had to follow this plan to the letter, no pivots, would I still raise?”
   

5. You’re Not at Chapter 3. Act Like It’s Chapter 1
   One of his investors told him: stop thinking like you’re further along than you are. Early-stage founders need to win deals, not build dashboards.
   

6. Partnerships Are Underrated at Early Stage
   Orita grew fast by doubling down on agency partnerships. The litmus test? “Do we make their customers happier and their company more money?”
   

7. Great GTM Is Founder-Led and Hands-On
   Early sales = hand-to-hand combat. Aaron warns against over-engineering funnels too early. Close one deal. Then the next.
   

8. Advising Sharpens Your Own Thinking
   Aaron advises founders not just to help them, but to pressure test and refine his own startup playbook in real time.
   

9. Burnout Is Real, And Focus Is the Cure
   Aaron has been through the darkest parts of founder burnout. His advice? Pick one thing. Do it well. Let that clarity drive everything else.
   

10. Your First Startup Is Opportunistic. Your Next One Should Be Intentional.
    Aaron’s early startups were born out of chance. Now, it’s all about alignment on people, product, and purpose.

Aaron Schwartz’s path isn’t polished, but that’s exactly what makes it valuable. He’s failed, sold, advised, burned out, and now he’s building again with more clarity, conviction, and curiosity than ever. If you’re early in your founder journey, his biggest lesson is simple: don’t rush the next move. Pick the right problem. With the right people. And go all in.

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