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

May 14, 2026

AI Summary

5 min read

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

When a $220 million deal collapsed the night before signing and the other side stopped returning calls, Alex Jekowsky didn't accept the outcome. He got in his car, drove to their location, waited at a coffee shop, and renegotiated the entire deal on the back of a restaurant receipt. That receipt still hangs in his house. "I don't need a deal to get done," he says. "I just need to know as much as I can get the feedback or the why. Because that can help me for the next deal, or maybe there's a misalignment that I can solve for."

Jekowsky is the founder of Sense, a laundromat technology company that powers one in nearly six laundry stores in the United States. Over his career, he has transacted more than $220 million in mergers, acquisitions, and capital raises. His approach to deal making is less about poker-faced negotiation and more about radical transparency, structural honesty, and building relationships that outlast any single transaction.

The Two Questions That Determine Whether a Deal Is Worth Doing

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What you'll learn

  • 1 (00:00) **Episode Introduction & Guest Background** - Host Kwame Christian introduces Alex Jekowsky, serial entrepreneur and founder of Sense, a laundromat tech company who has transacted over $220 million in M&A and capital raises.
  • 2 (02:34) **Deal-Making Philosophy: Acceleration Over Vanity** - Alex argues that the real measure of a good deal is whether it accelerates a pre-existing plan and de-risks execution, not the transaction size.
  • 3 (07:24) **Making the Other Side Feel Like They Hit a Home Run** - Alex prioritizes ensuring the counterparty feels successful, arguing that the only thing better than making money yourself is making someone else money.
  • 4 (10:34) **Showing vs. Selling: The Ferrari Principle** - Alex distinguishes between selling hard (which creates fragility) and showing authentic value (which lets deals close themselves).
  • 5 (12:41) **Radical Transparency as a Competitive Edge** - Alex explains how understanding the math behind investor return models allows him to be completely transparent in pricing and negotiation.
  • 6 (15:53) **The $220 Million Deal That Fell Apart Overnight** - Alex recounts his favorite negotiation story: a transformative acquisition that collapsed via email the night before signing.
  • 7 (23:37) **Why Deals Die: Structure, Pressure, and Deal Fatigue** - Alex analyzes the real reasons counterparties walk away, often related to the fear of answering to external pressure for the first time.

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Show Notes

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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