“In the Studio” opens its doors this week to an entrepreneur who co-founded, built, and sold his two startups to large technology companies, then teamed up with his co-founding partner to invest their own capital in startups, which provided the basis for their current fund and an impressive, diverse array of seed stage investments in consumer technology and infrastructure.
Before Josh Felser co-founded Freestyle, an institutional seed-stage fund, with his partner David Samuel, they built successful internet businesses, Spinner and then Grouper, which were both sold to larger companies. Having worked with Samuel for nearly 15 years, the two decided to invest their own capital in startups for a few years. As sort of a minimal viable product for investing, those two years convinced the pair to raise a fund from outside investors and professionalize their investment activities. With Freestyle today, the pair make roughly 5-6 investments each per year at the seed stage and spend significant amounts of time with their companies, acting as if they were part of the founding team.
In today’s world of party seed rounds and celebrity investors, Felser and his Freestyle team focus on something simple but potentially more powerful: their own first-hand experience as seasoned founders, operators, and executives. A founding team that partners with Freestyle can expect more involvement from Felser and/or Samuel, and so while this model isn’t for every new startup, it is certainly filling a niche that’s proven to serve their portfolio companies such as backtype, Get Satisfaction, and many others quite well. In this video, Felser is extremely candid about how he and Samuel approach seed investing in the current environment, what founders should expect from Freestyle’s involvement, and how he and his team cannot stop thinking and acting entrepreneurially, perhaps even to a point where they revisit their own investing model and specialize further.