Yesterday, I had a quick email exchange with one of my AdverseEvents co-founders. We were bantering back-and-forth about a new idea and he summed it up by saying, “it could be a fun challenge to take on, but it could also be a pain in the a**.” Without giving it a second thought, I wrote him back with, “Everything we do is both a fun challenge and a pain in the a**.”

Obviously, not everything we do is a pain and, frankly, not everything we do is fun. But the most worthwhile and rewarding things typically do end up being both a fun challenge and a pain in the a**.

For me, nothing is more painful than raising money. It’s a necessary responsibility for nearly every start-up CEO/founder and, oftentimes, the most important responsibility. Some of us are really good at it, some are really bad. I probably fall somewhere in the middle. I can put together a deck, make a decent pitch, answer most investor questions in a thoughtful way, and ultimately, steer a potential deal through the mechanics of legalities and closing.

But do I enjoy it? Not in the slightest.

I can never shake the feeling that I’m acting/walking/talking like a circus barker – promising all comers that if they just step inside the tent, they’ll learn the mysteries of the world, be delighted in all that they see, and earn ungodly riches.

I’m not sure where that poor self-image comes from. I believe wholeheartedly in what we’re doing at our company and I have every confidence in our team’s ability to execute and deliver results. So why should I feel hesitant to share those beliefs? Maybe it’s just a preemptive form of stress – knowing that taking on new investors means we now have another group of people who are depending on us to perform well. Or maybe it’s the rejection. Like any selling process, you have to go through a whole lot of ‘no’ before you get to ‘yes’. And I’m not a fan of ‘no’.

So, it was with great hesitancy that I embarked on the process of raising our first round of outside institutional capital. And you know what? It was a total pain in the a**. But, it also turned out to be a fun challenge. I got to meet and discuss our business with a lot of very smart people, hear a lot of ideas (some good, some not so good), and yes, get rejected. But we also ultimately got to ‘yes’. And like most things, it now seems that it was meant to be. We ended up with the best possible group of new investors – people with deep industry expertise in the healthcare data space. The kind of investors who don’t just come with a checkbook, but come with knowledge, experience, and contacts – and who are ready to roll up their sleeves to help us succeed.

Last Tuesday we announced the closing of our Series A financing. I spent most of that day with mixed emotions of relief and satisfaction. Relief in knowing the job was done, and satisfaction in knowing that the job was done well.

And how did I celebrate? I promptly spiked a 103 degree fever and spent the next two days in bed. But I’m on the mend now and ready to get on to the next pain in the a** (um, I mean fun challenge).
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Brian Overstreet

Brian Overstreet


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Brian Overstreet

Written by Brian Overstreet