People who've done PE for a few years - what was the toughest / lowest point of your career?

Hey guys:

Currently hitting a bit of a rough patch at my fund (low deal flow, not getting much experience, worried about future, etc.). For those of you who have done PE for a few years, what was the lowest/toughest point in your career, and how did things evolve from there?

Much appreciated!

 
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Only been in the investment game for about 2 - 3 years but the worst was when a deal we had been working on for ~8 months or so fell through.

My partners and I spent on QoE, significant amounts on legal, lined up a lender & paid DD related fees, cobbled together the equity we needed to execute the deal etc.... and then the founder of the company completely fucked her company (did the opposite of what we told her to do) and sales dropped massively almost overnight. The worst part too is that the business was seasonal so she missed out on a disproportionate amount of revenue.

We decided to cancel the deal and eat the loss ourselves. We could have charged our investors, but I don't think it would be the right thing to do/worth eating the reputation damage which is real when it's all your personal capital and 6 figures.

The kicker though, is that the founder tried suing us! It didn't go anywhere, but still, what the fuck? Ended up burning even more money there and it was just a kick in the head while down.

The monetary loss was annoying, but it felt weirdly bad being sued by the founder and I HATE that we spent all that time on the deal for nothing.

In the end though, it worked out, ended up with the bandwidth to tackle a different distressed deal that's since panned out nicely even with COVID factored in.

 

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