040: Tony Cappell on De-Risking the Deal and Earning Higher Returns


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By Justin Donald. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

Today, I’m speaking with Tony Cappell. Tony is the Principal and Co-founder at Chicago Atlantic Group — a private market investment firm combining deep expertise with an entrepreneurial approach to multi-asset class investing.

As a debt investor with over 10 years of experience in the specialty finance space, Tony has completed over 150 deals comprising over $5B in total credit.

Prior to founding Chicago Atlantic, Tony was a Managing Director and Head of Underwriting at Stonegate Capital, a private credit investment firm that specializes in the cannabis industry. At Stonegate, he was responsible for credit, underwriting and the growth strategy of the loan portfolio.

Tony is an unbelievable source of information when it comes to understanding loan and fund structure. He knows exactly what to look for when it comes to protecting the downside and mitigating risk. He’s also a wealth of knowledge when it comes to enhancing a deal and creating opportunities to earn better returns — or what I like to call, income amplifiers!

And today, you’ll hear us talk all about it! We dig into debt structure, strategies for de-risking a deal, how to negotiate better terms with things like equity kickers and liquidation preference, and why regulatory arbitrage is creating a massive opportunity in the cannabis industry. That, and a whole lot more!

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