Michael Karnjanaprakorn - The Founder's Psyche

Our interview this month is with Michael Karnjanaprakorn. Michael was the founder of the online learning community Skillshare and Otis, a financial platform for fractional ownership of alternative assets that was acquired by Public.com. As Michael navigates the idea maze for his next entrepreneurial phase, he graciously looks back on his journey thus far, offering a unique and honest look into the psyche of a founder. He discusses the grind of pursuing what he calls “the business Olympics” and the toll and delusion that can set in as a founder pursues this path.

One of the things Michael reflected on was the messy motivations that drive repeat founders to work on companies. There are many reasons to build a business, but ego can sneakily be a very powerful one. The desire to prove that the first company wasn’t luck, and that he could drive repeat success, was a much greater motivator in his second business than he ever realized. This caused him to skip some steps in the process of recharging, exploring, and evaluating his next idea.

What compounds this problem is that successful repeat founders are often enabled by those around them. Michael talks about how too much of the feedback on Otis was positive. Was this because the idea wasn’t bold enough? Or perhaps it was because too many people wanted to give a successful founder the benefit of the doubt and cheer him on? This was a case where I was personally involved and was probably someone in this camp. As an investor, my desire to work with Michael hurt my own objectivity when providing feedback on what he was building. This is something I’ve seen repeated many times and is definitely a pitfall that can trap well-respected, repeat founders.

This episode dives much further into Michael’s reflections on his past companies, including how he is thinking about the next stage of his professional life. I hope you enjoy the conversation as much as I did! Michael is one of the most thoughtful folks I know, and if you enjoyed this conversation, you’ll love reading his own writings and listening to his podcast The Karnjanaprakorn Show.