Self-Promotion Always Felt Gross

Necessary Evils

My bad. It’s been a minute. Two things that are important to me: 1) Content that matters, which means quality over quantity. If I can’t say something impactful, I won’t force myself to write. 2) Forcing some life balance when I feel things starting to get out of whack. I’m here to offer value but I’m not going to distract you with content for content’s sake. Today, I’m writing about a lesson I learned in the last 2 weeks.

I don’t want to divulge too many details, though you can dive into the shallow end of the pool and learn about what I have going on… I’ve been working on a seed round fundraise with an amazing co-founder and collaborator. Although I have a background in finance, I’ve never actually had to go out to private markets and raise capital. For anyone that needs clarification, picture a less entertaining version of Shark Tank (kind of). We make a pitch to an investor and if they like it, we agree to terms and a check is written. Oversimplified but accurate enough.

There is so much learning in this process. It’s an exciting challenge that I’ve enjoyed immensely, and simultaneously it’s made it hard to get out of bed some mornings. One of the questions you always get in a pitch meeting is, “Tell me more about your background.” This is the set up question that gives you the floor to discuss why you’re THE founder or founding team for this challenge to scale an idea into a billion dollar business. Up until about a week ago, all I had to offer was a dramatic amount of modesty.

Our lead investor pointed this out to me in some feedback after a meeting he observed. I sat there appreciating the accountability while scribbling notes furiously. He gave me a structure and emboldened me to be proud of what I bring to the table. My own postmortem of the situation revealed many things to me about why I was stuck in my own modesty:

• Cultural Habit - My entire life I’ve been obsessed with the trappings of cool and the understated. Wealthy folks that still drive a beat up Volvo; that’s impressive. I’ve been in fashion for 10 years and you learn that some of the dopest touches are the subtleties in design not the loud stuff. My inclination has always been to be that quiet-cool because cool doesn’t care whether you like it or not.

• Turn Off - Being overly self-promotional feels like selling a car on a used car lot. I don’t have a lot of used car lot experience, but I can picture the stereotypical image of it from TV shows and movies. Someone dressed in slick but cheap clothes, convincing me nothing is wrong with a car while trying to get me to finance a sticker price I can’t afford. My approach to selling was to never chase and so it’s a hard switch when you don’t have a lot of examples to the contrary.

• Self-Doubt - This is a big one. I don’t swim in a pool of the stuff, but I’m super familiar with it. When you’re a newcomer to a thing, you feel like you’re not good at anything. In this case, I’m learning new lingo and trying to understand how to be an attractive investment. I’m an investor myself, and I’m sitting here pretending like I don’t know what’s going on. But that’s the headspace you can find yourself trapped in. It feels like the scales are tilted and they actually aren’t. And one last thing - you think whatever you say isn’t going to be impressive so you lean towards saying less. (There is a case for brevity, but you should say the things that need said.)

Self-promotion is just one of many tools you need to accomplish certain tasks. If the job is to raise money, then it’s a great tool.

Self-promotion can easily be conflated with being egotistical, or slick (i.e. less than honest). However, like everything else, it’s about how you do it. I think this was the critical unlock for me. If I’m trying to sell you something you don’t need and can’t afford then it would be pretty gross of me to talk about my expertise and get you to trust me as you slide me your credit card.

In my case, this is not that. I’m raising money for a startup. A startup where my expertise and life experience this early on will go a long way to helping an investor decide our probability of success. As an investor, your job is to assess opportunities and risks. At the pre-seed and seed stages (early stage), all opportunities look grand while at the same time there isn’t a tremendous amount of data or metrics to paint a vivid picture of risks. Instead, an investor has to consider the size of the market, product market fit, traction, competition, and the team - to name a few things. The harsh reality is that the idea (the solution to a problem) and the team weigh heavily in the early days of a startup company. Believing in a great idea, but then having zero confidence in whether a team can carry the torch is red flag central for an investor.

I had to ditch my preconceptions about what the word self-promotion even means. I had to reframe it. Instead of self-promotion, I’m speaking passionately about my life story with pride and connecting it with relevance to what we’re building. That doesn’t sound or feel gross at all.

I also had to walk away from the computer and ask myself if I was in full acceptance of myself in all ways. I let self-doubt creep in and erode my confidence. I let my perceptions of strangers’ intelligence or experience dictate how I should feel about myself. It’s something I experienced back when I was interviewing for jobs on Wall Street. Back then, I stepped up and realized that the worst answer I could get was a “No.” Just two letters - doesn’t sound very devastating now does it? “Totally understand you’re not interested. Thanks for listening.” And move on.

I needed that same attitude it took to land a job a Goldman Sachs. Doing new things where I lack certainty and experience made me forget that I’ve had this energy all along. More than anything, I accept myself. I’ve been on a this journey for more than a decade to prepare for these opportunities. I’m great at what I do. I hustle, I grind, I leave it on the field. It’s my responsibility to make sure every investor I talk to knows that - and because I accept who I am, it’s not disingenuous or gross; it’s just me telling them about me. It’s the right tool for the job.

Those of you who read these essays are hard workers too. Like I always say, I don’t care what you do for a living you’re still a salesperson. I hope you can take this lesson and remember next time you have to close a deal, or promote your work, or whatever it is - that you take self-acceptance and confidence to that meeting. People can really feel it, and it’s important that they know you as well as your work. Good luck out there.