When you mix venture capital with a love of music, you’ll get this week’s guest, Andy Weissman — the current managing partner at Union Square Ventures. After graduating from Wesleyan University, Andy received his JD from Georgetown and quickly moved into venture capital. He describes himself as someone who stumbles through life looking for peace, happiness, and comfort, but I know him as someone who’s unlike any other venture capitalist I’ve ever met. In this episode, we talk about how luck and serendipity are one and the same and how he makes his investment decisions at Union Square Venture—particularly when factoring a company’s mission and purpose.
If ever you needed proof that you can build a profitable and valuable media franchise in the US that doesn’t pick political sides, the Morning Brew is it. Just last week, they were purchased by Business Insider’s parent company, Insider Inc., and in this episode, I’m speaking with Morning Brew’s Co-Founder and Crew Leader, Alex Lieberman. When Alex started his senior year at the University of Michigan, he already had a job offer from Morgan Stanley to trade on their mortgage desk—leaving him with some “free” time. He chose to do what everybody nobody does with this kind of free time: summarize business stories into a digestible and understandable email and send them to his friends still in the job hunt. Mikey liked it. This email would eventually become “Morning Brew,” and I highly recommend you sign up using my referral link so you can drink your morning brew while reading it. We talk about the Brew’s evolution from unscalable processes and zero full-time employees to today, where 60 employees produce general and industry- specific, bitesize content for a readership of more than 2.5 million people.
In this episode, I’m speaking with Freestyle.VC Partner, Jenny Lefcourt. We grew up together in Miami, Florida, and it’s been fun to watch her professional life evolve into what it is today. After graduating from the University of Pennsylvania,Jenny became a CPA at Arthur Andersen—where she discovered public accounting wasn’t for her. After a couple of years working for a startup in Silicon Valley, she attended the Stanford Graduate School of Business, before dropping out to start her own company. We talk about how—after an initial bumpy start—she discovered her true passion and became the co-founder of two successful startups, eventually leading to her current role as a venture capitalist.