Be the Heel or Be the Face: Why World Wrestling is a good school for Personal Branding and Investors

I grew up watching professional wrestling aka WWF now WWE when I was a kid. I swore it was real but like most things on tv it turned out to be fake, basically it was a soap opera with fighting. But it was damn addictive. 

I learned some new terms about the wrestling industry from my new favorite podcast called “More or Less” starring some top tier tech investors, operators, power couples, the Morins & Lessins, who discuss the zeitgeist of Silicon Valley. It’s entertaining, educational and fun. 

Of course in an episode it got around to the conversation on Elon Musk and his ownership of X formerly known as Twitter. How he has just gotten unhinged online in the last year. But Dave Morin used the terms “Heel” and “Face”. 

Elon Musk started off as a Face, a positive, the good guy and hero in the show. But as more information came up on how he treats people, as well as his more right leaning political views, he gets more engagement from being the “heel”. Otherwise known as the bad guy of the show, the person trying to elicit negative feedback from the crowds. These are actual characters being played. 

We all play this character and some of these we lean into. Most VCs want to be the “face”, being founder friendly and supportive. This is a good thing. But as I’ve said before, your job as an investor and ally is to also give bad news, to push  and question founders on their plans, cost structure so they can perform better. 

If all you are doing is “Face” work, then you are abrogating your duty to the founders. Yes,  it’s hard to be direct and question founders especially if you think they are going in the wrong direction and putting their business at risk. If you truly want what is best for your founders and for them to get better you have to be a heel sometime. This is how you earn your way to be their trusted advisor. Cheerleading when times are tough or good is fine but your job is also to help them look past corners and avoid potholes. 

This is why most venture investors suck at their job and will have no place in this industry. And I mean the venture industry globally. This is endemic in Silicon Valley. But being the Heel all the time is also bad, which is what I see in most of the emerging ecosystems. You need both. 

For better or worse, at least in the startup ecosystem I’ve fallen into the “Heel” role as investor. I try to be the face and act positive for my founders. But I also have to make sure I counterbalance too much unrealistic optimism and naivety when it potentially will kill or hurt the company. So venture investors, DO YOUR JOB! Be a heel and a face.