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I’m in this text group with a bunch of successful startup founders and recently a question came up around what your biggest investment mistake was?
There were lots of interesting stories and anecdotes which all brought a lot of collective comfort to everyone that they weren’t alone in their mistakes.
What I kept thinking about was why these scenarios happened to everyone including myself?
Most people write them off as bad luck, ignorance, or poor decision making, but I think there’s a lot more going on here as I’ve alluded to in the responsive reality and my thoughts on manifestation.
The more we understand these hidden forces that shape our lives, the better set up we are to have our life go well.
Abandoning Myself and A Pile of Cash
I wanted to share a concrete example in my own experience how unconscious self sabotage likely cost me millions of dollars. By writing about this maybe someone out there will see themselves in the story.
In 2014 I was living in Rio De Janeiro Brazil with a group of friends running a “creator business” that sold online courses on startup sales and business development. I was 25 making over $200,000+ a year running my own business while working probably around 15-20 hours a week. I wasn’t quite Tim Ferriss living the 4 hour work week, but I was on my way and felt like I had arrived.
In March that year, I went to SXSW and met all these people just like me that had their own podcasts. I loved podcasts and considered myself a good speaker so I thought I’d throw my hat in the ring.
At the time, I was very focused on “crushing it” across all avenues of life so I decided to make the podcast about interviewing high achievers on how they got their “competitive edge” to become so successful. I named the show The Competitive Edge and launched it May 1, 2014.
At the time podcasting and the creator economy wasn’t this big thing. It was much more fringe and most friends that were working in banking and consulting thought that I was pretty weird for using my Princeton education to become some blogger / podcaster who sold courses while living on the beach in a foreign country.
So the idea of my podcast becoming a big business opportunity wasn’t really a huge motivator for me. I was more looking for my next act and it seemed like talking to interesting people would be fun. My hunch ended up being right and it turned out that I loved podcasting.
Over the next year, the podcast started to become quite successful. At one point it was ranked #4 on iTunes in business and even featured alongside business inspirations of mine like Tim Ferriss!
After a year of publishing, the podcast grew to 100,000s of thousands of downloads a month.
I would email the shows out to my email list and post on social media. But most of the growth was organic because I was highly ranked in the iTunes app store where people would discover new shows. At the time, it wasn’t so crowded and there was lots of white space to grow on the back of iTunes if you were creating a good show.
Despite all this success, there was this feeling inside of me that I was “playing small.” I felt like there were all these people in my previous tech circles starting tech companies and raising millions of dollars and I was a guy selling courses, blogging, and doing a podcast. This was accentuated by the fact that many other online marketing people I was meeting felt kind of squirrely and not like people that I was aspiring to be like. There were obviously some gems too.
So despite the fact that by conventional standards all these things were going incredibly well, I felt like a chump and had massive imposter syndrome.
Who was I to be giving people advice on how to be successful in life?
When these uncomfortable feelings came up, the story I kept telling myself was that “I miss working with other people as part of a bigger mission” and “I really want to get back to tech.”
It’s not that I didn’t miss working with other people, but I now see that this compulsion to stop doing something that gave me creative energy and joy was much more a symptom of an unconscious sense of worthlessness and low self-esteem. In my unconscious mind, I wasn’t enough and even with a successful podcast and lots of money, I still felt that way.
So I thought I had to go do something “bigger.” This was all a strategy to protect myself from facing the mental formation of being worthless.
There was also a desire to get away from any type of business where the product was “me” which included the podcast. I thought this was just because I didn’t like the burden of having to deal with people criticizing or expecting so much from me which happens when you grow a big audience. But the stronger unseen force was that it was very hard to sustain a “business of me" when the most expansive part of your consciousness (the unconscious) doesn’t think it’s worth much.