STORIES FROM A CHEEKY CAPITAL RAISE PART 3: "SOUNDS LIKE YOU'VE DONE THIS BEFORE"

A couple of weeks ago I had a conversation with investors about coming in on Cheeky’s seed round, and they said it sounded like I had raised money before. I laughed and said, “Not…exactly. I had a couple of false starts years ago, so I’ve been teaching myself about it for the past several years…."

Fast forward to this week. I got into a random conversation with a friend about podcasts and the Gimlet/Spotify acquisition, and I mentioned that my first investor pitch ever was pitching Swig + Swallow on The Pitch (a Gimlet podcast) almost exactly four years ago.?

Now, I’m a huge believer in taking opportunities when they present themselves and specifically when it comes to media, you’ll never be as prepared as you want so you just have to run with it. Not only did I present on The Pitch without having formally pitched to investors, but the first time I was filmed it was for a feature on the Sundance Channel, and the first time I was on live TV it was for the Today Show, so the tactic of “commit, prepare, and bring it” had already proven to work for me. Knowing what I know now, I would definitely have done some things differently, but across the board, taking the opportunities was the right move, and I’d do it again in a heartbeat.

Now, back to the Pitch.?

Like many startup founders, I'm a product person and industry veteran first, and learned business “on the job.” While it certainly took me longer to get where I am without having a business background, my “why,” my connection to the need and the product, and my understanding of the various industry dynamics is crystal clear, and I’ve managed to gather people and resources to help me become fluent in the language and mechanics of business. Of course it’s a never ending learning process, and frankly that’s why it continues to be so exciting.

I’m not sure how many people reading this will listen to the original podcast episode, but re-listening to it now after so long definitely makes me cringe. In the four years since it was published I think I listened to the whole episode once or twice, but fast forwarded through my part (couldn't bear to listen) and listened to the investor feedback section maybe 20 or 30 times (their excellent feedback helped change the course of the business!)

The reason I’m sharing my “cringey-ness” about this here on Linkedin is because like so many things, (growing a business, raising money, etc etc), you can’t know “it" until you experience it, and you can’t fault yourself for where you started. Could I have saved myself a few years of struggle if I had an MBA? Maybe, but I would have lost those years getting customer and investor feedback and really understanding I was made to run this business, and that my “why” runs deep.

Could I point out a million things “wrong” with what we were doing then relative to now? Most certainly, but when you don’t have enough data, you make the assessments and assumptions you can with the data you have. I talk to a lot of early stage startup founders, and they all have their version of this story. I’m here to say as founders you need to take control of your fate and responsibility for your actions, but you can’t fault yourself for where you started, and you can’t fault yourself for being early stage.?

If you’re an entrepreneur in this position yourself, just know that you are where you are, and those that want to be a part of your journey will be excited to be involved in your young business. A "no" now doesn't mean "no" forever, and ideally you get feedback that will help you stay in the game for a while, which has continued to be the case for me. Understanding the objectives and perspectives of super smart people has no downside, and who knows, if you stick with it long enough, someone might even say “sounds like you’ve done this before."?

:)