The Deals You'll Actually Fight For

David Rubenstein has talked openly about some of the investment opportunities he passed on and later regretted. 

Amazon. Facebook. Netscape. 

Years later, a different opportunity came along: the chance to buy his hometown baseball team, the Baltimore Orioles. 

That one, he took. And what stuck with me wasn't the investment itself. It was the reason behind it. Baltimore was home. This wasn't only an opportunity to generate a return. It was an opportunity to invest in something he genuinely cared about. 

It gave him a reason to care beyond the return. 

I think there's a business lesson in that. Think about the things you've pushed hardest for. The extra hours. The difficult conversations. The project you refused to give up on. 

I'd bet some of them weren't driven entirely by money. 

When an opportunity connects to something you genuinely care about, you show up differently. 

But there's a danger there, too. Personal connection can make you more committed. It can also make you less objective. That's why passion alone isn't an investment strategy. 

Passion determines whether you're willing to fight for the opportunity. The numbers help determine whether you should. 

Not every return has to be purely financial. Sometimes you're investing for ownership. Control. Legacy. Community. Independence. Or something you simply want to exist. 

The key is knowing what return you're actually looking for and what you're willing to sacrifice for it. 

So next time you're evaluating an opportunity, don't ask only: "Which one could make me the most money?" 

Ask: "What am I actually trying to get from this deal?" Then put the numbers next to it. 

Just make sure the money still makes sense. 

J&C Briefs | Joachim & Co. 

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