Embrace the Pain: What It Really Takes to Build a Billion-Dollar Business - Alex Jekowsky

May 14
1h 3m

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Episode Description

Most entrepreneurs talk about deals. Alex Jekowsky of CENTS has negotiated over $220 million worth of them.

In this episode on negotiation, acquisitions, fundraising, and entrepreneurship, Alex breaks down the real psychology behind high-stakes dealmaking — from navigating multimillion-dollar acquisitions to building trust with investors, overcoming rejection, and turning painful setbacks into transformational opportunities.

But this conversation goes far beyond tactics.

Alex shares the emotional realities of entrepreneurship: the pressure, the uncertainty, the loneliness, and the resilience required to keep building when the odds are against you. From renegotiating a failed acquisition deal on the back of a coffee shop receipt to raising the largest venture round in laundry technology history, this episode is packed with battle-tested lessons on leadership, authenticity, reputation, and growth.

You’ll learn:
• Why the best negotiators focus on alignment, not manipulation
• The hidden danger of “selling” instead of “showing”
• How great founders structure deals people actually want to win
• Why pain tolerance may be the ultimate entrepreneurial advantage
• The mindset shifts that helped Alex scale Sense into an industry-defining company

Whether you’re raising capital, buying a business, leading a team, or negotiating your next opportunity, this episode delivers practical wisdom from someone who’s lived every side of the table.

This isn’t theory. It’s real-world dealmaking at the highest level.


Connect with Alex Jekowsky:

  • 🌐 Trycents - for laundromat owners and anyone interested in the garment care and repair industry
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