It’s not surprising that one of the pioneers of online dating believes that being open to options and new ideas will help your life and career. Sam Yagan is Co-Founder and Managing Director of Corazon Capital, an early-stage firm based in Chicago with a MidWest focus. But Sam is most known for Co-Founding OKCupid! and moving up to become the CEO of Match Group, where he helped launch Tinder.

This was a wonderful and sometimes introspective conversation on the challenges of being a founder, the power of being open to new possibilities, and where we are with the current market.

We also have a news recap with John Ruffolo.

About Sam Yagan:Sam Yagan serves as Co-Founder and Managing Director of Corazon Capital, an early-stage venture capital firm. He recently served as the CEO of ShopRunner, Inc., leading its 2020 sale to FedEx Corp.

Prior to ShopRunner, Sam served as CEO of Match Group where he led the company through the launch of Tinder in 2012 and through Match Group’s IPO in 2015. Sam’s prior entrepreneurial ventures include SparkNotes (founded in 1999) and OkCupid (co-founded in 2004).

Sam has a BA from Harvard College and an MBA from the Stanford Graduate School of Business.

In this episode we discuss:

(00:01:17) News recap with John Ruffolo(00:20:58) Sam Yagan’s journey to entreprenuership(00:26:14) Was his career all luck?(00:28:20) How the exit of SparkNotes went(00:30:02) Regrets about not buying SparkNotes back(00:34:53) Seeing companies with broken cap tables but functioning businesses(00:36:57) Why they started OkCupid!(00:41:20) Deciding to sell to a larger rival, and then becoming its CEO(00:45:45) How Sam dealt with Imposter Syndrome(00:49:30) The PlentyoFish Acquisition(00:52:05) Deciding to career pivot to ecommerce(00:54:46) Lessons learned as an outsider coming in at ShopRunber(00:58:32) Why Sam chose to be a MidWest VC(01:01:23) How Sam’s investing thesis has evolved(01:03:33) What Sam likes to invest in(01:04:26) Why they missed on Cameo(01:05:24) What Sam is passionate about in the future

Fast Favorites:

* 🎙- Favorite Podcast: Succession

* 📰- Favorite Newsletter /Blog: Matt Levine’s Money Stuff

* 📲- Favorite Tech Gadget: 8 Sleep

* 📈- Favorite New Trend: Alcohol abstinence 

* 📚- Favorite Book: Influence

* 🤔 - Favorite Life Lesson: Be willing to fail

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