Today we are replaying one of our most popular episodes from last year with Jeremy Giffon. I spend all my time trying to find people who have some “singularity” to them. People who seem like they can do an N of 1 something. Having spent many days with Jeremy, he strikes me as one of those people. He was the first employee and general partner at private equity firm/holding company Tiny, which buys and holds internet and technology-focused businesses. Prior to that, he was on the founding team of MediaCore, which was acquired by Workday.

The focus of our discussion is on esoteric opportunities that exist in private markets and how misaligned incentives and coordination problems create special situations for people like Jeremy to invest in. The rest of the conversation is wide-ranging and covers everything from compensation advice to meeting your heroes. Please enjoy my discussion with Jeremy Giffon.

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For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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Show Notes

(00:00:00) Welcome to Invest Like the Best

(00:03:15) What defines the nature of a perfect business in his mind

(00:05:21) Key characteristics he’d look for in a perfect investment

(00:09:58) Coordination problems that excite him

(00:14:02) Raising funds and ghostship companies

(00:16:17) Examples of a special situations transaction in private markets

(00:18:55) Building up a sourcing mechanism

(00:22:18) The biggest mistakes he’s seen in buying and selling companies

(00:25:42) Refining the underwriting process

(00:28:57) Thoughts about minimum rates of return and multiples on capital for the investments he makes

(00:30:44) Being lazy enough to wait for good deals on enduring businesses

(00:33:32) Why people do things they don’t like

(00:35:47) Whether or not he feels like he knows what he wants in life

(00:42:58) Hiring CEOs

(00:44:54) Really good respective returns in low risk companies and why those opportunities continue to persist

(00:47:05) Tactics for negotiating with and sourcing CEOs

(00:50:37) Binaries - pre and post fall

(00:55:58) Being hard to kill

(00:59:15) His favorite interview question

(01:06:07) Having an audience is incredibly underpriced

(01:10:13) What else is significantly underpriced

(01:12:14) Things he feels are overpriced today writ large

(01:15:54) Criticisms of the cult of learning

(01:20:21) The one call that everyone needs to make

(01:27:18) Meeting your heroes and having mentors

(01:30:48) Notable differences between the business environments of Canada and the US

(01:33:13) Lessons learned from people he admires and models for seeing the world

(01:35:35) Views he holds that would make people scratch their heads

(01:40:02) The kindest thing anyone has ever done for Jeremy

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