As someone who entered the venture industry in the wake of the Dot-com crash, I have a deep appreciation for new managers, their entry point into the industry, and how that shapes their world view. For me, it was pure carnage for the first few years of “investing”. I put that in quotes because it was mostly triaging the portfolio and trying to assess which companies were worth saving and which were destined for the Dot-com dust bin. 

Shortly after stepping out on my own to start OATV, another bubble burst with the Global Financial Crisis™. My trips to NYC for board meetings were often capped off with midnight strolls through Zuccatti Park to witness the occupation of Occupy Wall Street. The markets were in free fall, checkbooks closed, and founders, once again, were at the mercy of the market. 

But easy times never make for strong people and that’s why I was excited to sit down with Turner Novak when we both found ourselves in Columbia, MO for the Main Street Summit a few weeks back. His is a “chronically online” story of discovery and persistence into the world of startups and VCs. Through the use of memes, social networks, and data, Turner was able to build an audience and a “fantasy portfolio” to land himself an internship and, eventually, a fund of his own. 

Turner came into his own as an investor in the frothy times of the not-too-distant past. With wide eyes and fresh funds to deploy at his newly formed firm, Banana Capital, he set to work deploying near the peak of the ZIRP bubble. I thought it would be fun to unpack the experience of someone who built their brand online, from the midwest, and began deploying into a market that’s rules and dynamics quickly changed on them. 

With that as the goal, this one did not disappoint. A few takeaways: 

- Turner’s exposure to entrepreneurship began early with his mother running a small wedding gown business. Turner developed an interest in technology and the internet during his teenage years, teaching himself programming.

- Turner’s path into venture capital began in college, where he joined the investment club and got hooked on investing. After working in commercial lending and for a nonprofit endowment, he started building a “fantasy VC portfolio” on Twitter, which helped him break into the industry. His visibility on social media eventually led to his first job in venture capital.

- Turner’s largest learning from the last few years in venture is the importance of entry points — getting in at the right valuation can make or break an investment. While many aspects of startups are unpredictable, controlling the price you pay is crucial for long-term success.

This was a really fun one and I think Turner has a bright future ahead of him as an investor and fund builder. The easy times may be over, but I can see his strength already showing through as he navigates this new reality. 

I hope you enjoy listening as much as we enjoyed recording it. 

PS - Today is my birthday and all I want is for you to A) subscribe to the INDIE YouTube channel (just hit that subscribe button) and B) send the next category defining company our way. Is that too much to ask?!?