Just wrapped my second year chairing the EO Deal Exchange Conference, and the lessons were off the charts.

Here's what happens when you put hundreds of entrepreneurs in a room focused on one thing: growing through deals.

Three insights that stood out:

The wisdom is already in the room. We ran deal speed networking sessions where members shared their specific needs (buying companies, seeking JV partners, raising capital). The collective knowledge and connections in that room solved problems in minutes that could take months to crack alone. Stop looking outside your network for every answer.

Exit satisfaction is shockingly low. Dave Hirsch shared that only about 13% of entrepreneurs who successfully exit are actually happy afterward. His "Inner Board Meeting" concept helps you identify all the different voices and aspects of your personality that need to be satisfied by any deal you pursue. Powerful framework for avoiding founder depression.

Lifestyle business isn't an insult. Silicon Valley prodigy Fallon Fatemi, who co-founded an AI company with Mark Cuban, shared that she'll never raise capital again. Not because capital is bad, but because her priorities have shifted. Build the business and life YOU want, not what others expect.

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FOR MORE ON THIS EPISODE:
https://www.coreykupfer.com/blog/kraftheinz
• • •

FOR MORE ON COREY KUPFER:
https://www.linkedin.com/in/coreykupfer/
http://coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

85% of founders have regrets about their exits. The research is clear. But here's what surprised me most about this statistic: almost none of them regret leaving money on the table.

They regret the clarity work they didn't do beforehand.

In my latest conversation with Jodi Hume, an advisor who works exclusively with founders and CEOs navigating acquisitions and exits, we explored what that clarity actually looks like:

How to distinguish between what you can compromise on and what will keep you awake at night years later.

Why energy management during due diligence directly impacts the quality of your decision-making.

The identity piece nobody talks about: who you are after the company is no longer yours.

How to protect yourself from making decisions born of depletion rather than strategy.

The uncomfortable truth about founder burnout and when an exit might be the right call precisely because you've hit your limit.

Jodi's approach is unusual. She's less interested in maximizing valuations than in ensuring founders actually get what they came for—and that they don't regret it afterward.

Listen to the full episode if you're even thinking about an exit in the next few years.

FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jodihume

FOR MORE ON JODI HUME:
https://www.linkedin.com/in/joditurnerhume/
https://atthecore.com/

FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!

Concentration beats diversification. One stock. That's all Jaden Sterling bought during the 1990s. It tripled, became capital for 125 real estate deals, and eventually funded Sterling Stock Picker, a stock-picking platform now serving 3,000 investors.

What most financial advisors don't tell you: diversification is what you do when you don't know what you're doing. When Jaden's clients at Merrill Lynch held 4-6 solid companies, they were pressured to sell and diversify into mutual funds. The math later showed holding those original positions would've beaten all the churn.

The path to real wealth isn't about spreading money thin. It's about focused conviction in what you actually understand.

I sat down with Jaden to talk about deal structures across real estate, concentrated stock investing, raising capital from customers instead of VCs, and why your relationship with money mirrors your relationship with yourself.

FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/jadensterling

FOR MORE ON JADEN STERLING:
https://www.sterlingstockpicker.com/jaden_sterling

FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!