This conversation explores the remarkable journey of Mark Leonard and his creation, Constellation Software, which has grown from a modest $25 million investment in 1995 to a $92 billion empire through a unique acquisition strategy focused on vertical market software companies. Leonard's approach emphasizes patience, discipline, and a decentralized management structure that empowers individual business units while maintaining rigorous financial standards. The discussion highlights the importance of long-term thinking, frugality, and the cultivation of a strong company culture that values autonomy and stewardship over short-term gains.

I wanted to know more about QSBS…
So I found someone who used it—not just read the IRS page.

Kevin McGee is an attorney who bought a craft brewing company. He used QSBS to eliminate capital gains tax on the exit.

We sat down and talked about:

• How QSBS works (and what most buyers get wrong)
• New rule changes in 2025 that make it even more powerful
• The legal landmines that can kill your QSBS eligibility
• How to set up a C-Corp to acquire a business and still qualify
• Why compliance isn’t optional—it’s everything

This might be the most overlooked tax strategy in SMB acquisitions right now.

What do crawfish, Walmart, and 7-Eleven have in common?

Neal Cobb.

He started as a chiropractor. Then built a delivery startup that scaled to 35 states, raised $20M, and was acquired by 7-Eleven. In this episode, Neal shares how he turned down $10M, powered through COVID, and now buys legacy businesses with big EBITDA and long-term upside.

Chapters:
00:00 From Chiropractor to Startup Founder
05:38 Scaling with Walmart
11:26 Raising Capital & COVID Pivot
17:06 Acquired by 7-Eleven
22:41 EquityX: Buying Legacy Businesses