The $12M Pivot: Alex Song’s Proxima Play

In Season 3, Episode 18 of Turning Pro, Ben and Adrian sit down with Alex Song, founder and CEO of Proxima, a B2B data intelligence platform that recently closed a $12M Series A. Alex’s journey spans a decade of entrepreneurship, but it started in the halls of Goldman Sachs and Pershing Square, where he built an almost comically high pain tolerance. 

That experience gave him the edge to weather the chaos of building companies, including losing a teammate to COVID, transitioning from brand founder to B2B SaaS, and reestablishing trust after periods of team misalignment.

In this conversation, Alex unpacks what it really takes to become a world-class founder: emotional resilience, therapy, spiritual purpose, and the willingness to run through walls for your team.

Listen to the latest episode of Turning Pro Podcast with guest Alex Song on Apple, Spotify, or YouTube.

10 Key Takeaways from Alex’s Episode

1. Resilience comes from reps, not motivation: After a decade in high-stress finance jobs, Alex built a tolerance for the grind. But it wasn’t until he embraced therapy, coaching, and emotional awareness that he could sustainably lead for the long haul.

2. Founders need a pain ceiling and an emotional floor: In his early days, Alex’s highs were 10s and lows were 2s. Today, he aims to stay between 4 and 6 - measured, clear-headed, and focused on long-term impact.

3. Building a startup is like pulling problems from a bag every day: Alex trains his team to expect and embrace problems as opportunities. That mindset shift keeps energy high, even when the day-to-day is brutal.

4. The best leaders lead themselves first: Alex tapped into coaching and therapy not because he was struggling, but because he wanted to be world-class. Just like Djokovic doesn’t train alone, great founders build a support system.

5. Don’t delegate what you don’t understand: Early on, Alex hired people to do the stuff he didn’t want to do. Now, he prioritizes hiring for areas where he has context because it leads to faster onboarding, better performance checks, and smarter management.

6. Transparency is how you rebuild alignment after chaos: During Proxima’s Series A raise, Alex got disconnected from the day-to-day. His solution: go on an internal “CEO campaign trail,” owning the gaps, restating the vision, and repeating it 7+ times to rebuild trust.

7. Culture isn’t vibes. It’s commitment: After losing a team member to COVID, Alex doubled down on culture-building. Proxima now invests heavily in company-wide rituals, connection, and care, even sending cocktail kits for remote mixology nights.

8. B2B founders must build in public: Alex was skeptical at first, but he now believes personal brand is table stakes for B2B. Not for ego but for leverage, hiring, customer trust, and compounding momentum.

9. When things go quiet, double down on purpose: Whether it’s fundraising slowdowns or client churn, Alex returns to clarity of purpose; why he’s building, who he’s serving, and what kind of leader he wants to be.

10. Your turning pro moment is when you stop building for your ego: Alex’s biggest shift came when he stopped chasing importance and started chasing impact. Proxima wasn’t built to make him feel good; it was built to solve a real pain point he lived with for years.

Alex’s story is a rare mix of financial grit, spiritual growth, and real-world leadership. From his early days in investment banking to building Proxima into a venture-backed platform, he’s proof that emotional intelligence and operational excellence don’t have to be at odds. If anything, they compound.

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