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

Negotiate Anything

American Negotiation Institute

Business, Education, Self-improvement

4.7 • 748 Ratings

🗓️ 14 May 2026

⏱️ 66 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 💼 Connect on LinkedIn - Alexander Jekowsky

Transcript

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0:00.0	What would you do if a $220 million deal fell apart the night before signing and the other side stopped returning your calls?
0:10.0	Well, today's guest, he didn't panic. He got in his car and you will not believe what happened next.
0:17.0	I don't need a deal to get done. 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 can maybe I, maybe there's a misalignment because these things are complicated.
0:29.2	Maybe there is a misalignment that I can solve for.
0:31.6	The guest I'm talking about is Alex Gikowski.
0:34.3	He's a serial entrepreneur and founder of Sense, a laundromat tech company and a dealmaker
0:39.4	who has transacted over $220 million in mergers and acquisitions and capital raises.
0:45.3	So I think it's the so much of all of this is like every deal is, and I can't speak to this
0:52.6	as a man, so I know that, but it's childbirth
0:55.3	is the only thing I can really imagine. Every deal is that painful and extraordinary and
1:03.8	hopefully beautiful at the end. Yeah, boy, challenging, but you got to love the pain.
1:09.8	In this episode, we get into why being radically transparent in a negotiation is often your
1:14.9	biggest competitive edge, how to make the other side feel like they won even when you're
1:19.8	getting what you want, the difference between showing and selling and why the best deals
1:24.4	close themselves and what founders get dead wrong when they think about
1:28.3	who's actually going to buy their company.
1:30.6	If you're ready to start making deals that stick and building the kind of reputation that
1:35.3	brings great deals to you, this episode is exactly what you're looking for.
1:39.8	Let's jump in.
1:49.0	So this episode is brought to you by Granola, Quince, home serve, and by Shopify. If meetings are eating up your day, granola is a no-brainer.
1:53.0	Get three months for free at granola.a.a.
1:55.0	slash quami.
	...

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