💵 My $10,000 Leadership Memory

In the world of startups, there's a lot of "client entertainment" that takes place. It can range from a simple lunch to an elaborate weekend of golf to even some bigger and/or illicit experiences that stay off the books.

One SaaS startup I worked was acquired right before our annual customer experience trip in Las Vegas. When business trips take place in what I like to call "adult Disneyworld" client entertainment can get out of hand quickly.

It was not uncommon for me to take groups of 5 to 10 out for a nice dinner. The expenses would be fronted on my AMEX card and then I'd be reimbursed by the company with largely no questions asked. I don't recall ever spending more than $5,000 on any one night and rarely more than $500.

Anyway, this night in Vegas, I had a table for 10 booked at a steakhouse. The word got out amongst several of the new sales reps that I had this table. Those sales reps were having trouble getting a reservation and thus asked if they could be added to my reservation.

Well, that reservation went from 10 to 40!

I was the only one representing the company that was not overly inebriated in some way. I told the waiter what my limits were on the bottles of wines and drinks that could be ordered. I gave him my only AMEX card without a limit on it and told him to check with me on any food orders over $100.

TL;DR

The final bill ended up being over $10,000. I think it was closer to $12,000. But I remember a kind of gut-punch when realizing I had to cover the costs for a month before I would get reimbursed.

One of my sales colleagues stumbled over to me and saw the bill. "F*ck dude! Can you imagine having to write a check to a dinner you didn't even get to taste?!"

I didn't say anything. I just smiled.

It dawned on me how much revenue the company had to generate (or raise) to cover expenses like this every month for multiple sales reps. I remember consciously thinking, "I want to be the guy that has the money to write the check to reimburse my employees."

I always have a clear vision in mind of the type of leader I want to be. That moment made me realize how much could be riding on my shoulders if my vision continued progressing towards a company valued at $300 million.