With the disaggregation of traditional media, the popularity of influencers, and the unraveling of ad platforms like Facebook, creating a community through content has never been more important. Our guest today knows about the power of content and how it can grow into something world-changing. Austin Rief , is the CEO and Co-Founder of Morning Brew , an online media powerhouse that was founded as a newsletter in the dorms of the University of Michigan in 2015. Its impact and growth quickly became apparent and in 2020 it sold a majority interest to Business Insider for a reported $75M. Austin is also a solo capitalist at his fund, Austin Rief Ventures. About Austin Rief: Austin started at the University of Michigan as a Finance major in 2014, and he left 3 years later with a degree and was well on his way to becoming a media mogul. Co-Founding Morning Brew in 2015 and was originally the COO, he became the CEO in 2021. He also started a rolling fund on Angel List and parlayed that into Austin Rief Ventures, a seed-stage fund. In this episode we discuss: 01:34 The early days of bootstrapping Morning Brew 02:13 Early expectations for Morning Brew 03:41 Lessons learned from the M&A process 05:16 Why they decided to sell in 2020 06:24 What the internal conversations were like around the sale 07:48 Why Austin decided to start investing 09:28 Reasons why founders seek him out to be on their cap table 11:58 Why he believes content and social media can help founders 14:31 How his due diligence process works 15:50 Favorite questions he likes to ask founders 17:27 How he views portfolio construction 19:28 Getting allocations in competitive rounds 20:33 How he views founders with stacked SAFE rounds 21:44 Why it’s okay for founders selling on the secondary 24:00 How top funds will need to adapt to smaller investors getting pro rata 25:05 Working and attracting LPs as a solo capitalist 27:06 Austin’s skillsets that founder come to rely on 28:15 The importance of finding a CEO coach 31:31 What Austin is most excited about in the startup space 34:48 Why it’s important to be in the best companies 36:41 The future of Crypto and Defi and why he invested in Rare Circle 40:26 Thoughts on the new YC deal structure 42:40 What Austin has learned from his misses 46:14 Plans for Rief Ventures Fast Favorites: Podcast: Trillionaire Mindset All-In Newsletter/Blog Morning Brew Ben Thompson Pack McCormick Tech Gadget Eight Sleep Mattress New Trend The feud between threads and shitposters Book: Not Fade Away When Breathe Becomes Air Life Lesson: Focus on increasing luck’s surface area Follow Matt Cohen and Tank Talks here! Podcast production support provided by Agentbee.Agency