Episode 109: On today’s episode, I am going to break down and analyze an essay by one of my good friends and the super popular internet writer, David Perell. David is a prolific content creator, the founder of the super popu…
Episode 108: For today’s episode, I read and analyze startup founder Paras Chopra’s essay on market size from his online book Mental Models for Startup Founders. Chopra’s essay suggests that entrepreneurs should want to defi…
Episode 107: Today, I break down one of my favorite issues of one of my favorite newsletters, No Mercy No Malice, which explores why some entrepreneurs are considered visionaries and others are called frauds. Original Essay:…
Episode 106: On today’s episode, I read and breakdown Speed as a Habit by David Girouard, CEO of Upstart and former president of Google Enterprise Apps. This essay was originally posted on First Round Review, one of my favor…
Episode 105: For today’s episode, I read and break down The Great Online Game by Packy McCormick. This essay provides a completely new way of looking at the internet economy, and how you can structure your career and life in…
Episode 104: Today, I’m going to be breaking down an essay by Morgan Housel, one of my favorite internet writers. Morgan is a partner at Collaborative Fund and a New York Times best selling author of The Psychology of Money …
Episode 103: I’m going to break down a seminal essay by Andreesen Horowitz General Partner Chris Dixon. In 2010, Chris wrote an essay titled “The next big thing will start out looking like a toy,” which talks about why the n…
Episode 102: For today’s episode, I’m going to be reading 3 emails from Elon Musk. These emails were initially just for Tesla employees’ eyes, but were eventually made public. I think these emails not only give good insight …
Episode 101: I’m going to be reading quite possibly the most viral twitter thread in the world of business ever. In 2018, Naval Ravikant, wrote “How to Get Rich (Without Getting Lucky),” a 40-tweet thread that covers everyth…
Episode 100: On this episode, I’ll be sharing the best moments from Lenny Rachitsky’s recent interview with Brian Chesky, the co-founder and CEO of Airbnb. Airbnb is a $95b company that under Brian’s leadership has grown int…
Episode 99: I’m going to be reading and analyzing one of the most famous essays that has been published on the internet in the last 20 years: "1,000 True Fans" by Kevin Kelly. Kevin Kelly is the founding executive Eeditor of…
Episode 98: I’m going to be breaking down a 45-minute video by one of the greatest startup minds of all-time, who quite possibly, you’ve never heard of. Bill Gross is the founder of Idealab, considered by many to be the worl…
Episode 97: On this episode, I talk with Sahil Lavingia about his 2019 essay titled “Reflecting on My Failure to Build a Billion-Dollar Company.” Sahil is the founder and CEO of Gumroad, an e-commerce platform for creators. …
Episode 96: Most startups and their founders don’t spend their money well, often using it as a crutch for a bad product or a misguided tool for growing their business too quickly. Today, I’m going to read essays from Elad Gi…
Episode 95: Today, I’m sharing one of the greatest pieces of business writing living on the internet today. It’s been hiding in plain sight since 1997 yet the fact every entrepreneur hasn’t read it is criminal. I’m talking a…
Episode 94: Alex Lieberman ( @businessbarista ) takes you through an exercise to recalibrate and focus on your zone of genius. The zone of genius is work that you do that brings out the best version of yourself. Follow this …
Episode 93: Today, we’re talking about product-market fit. Product-market fit is one of those things that every startup founder obsesses over, but it’s always been this elusive thing that can’t be measured or quantified. Unt…
Episode 92: Today, we’re talking about founder personal finance. My buddy Ankur Nagpal is the founder and CEO of Carry, a business that helps business owners build wealth in a number of ways, most notably with their Solo 401…
Episode 91: I did something crazy. I convinced HubSpot to send me and 7 friends to sit 50-yard-line at the College Football National Championship. The deal is simple. They’re paying for our seats. We’re gonna do some awesome…
Episode 90: Today I’m interviewing Jason Fried, who is a legendary entrepreneur. Jason is the cofounder and CEO of 37signals, which is a software development company that has created popular products like Basecamp, Hey, and …
Episode 89: Most new year's resolutions fail. Studies say north of 90%. So I’ve built a program for myself and others that I believe will help people be the exception versus the rule for new years resolutions. I’m going to t…
Episode 88: Today, I’m highlighting a nearly $20m per year business that is run in a pretty unconventional way. This business has no meetings, no deadlines, and no full-time employees. The business is Gumroad, an e-commerce …
Episode 87: On this episode, I take questions from you all! I discuss three big lessons from building Morning Brew, how I’ve processed the loss of my dad, facing OCD while building a business, transitioning out of finance in…
Episode 86: Today, we’re talking about mining the internet for great business ideas. And to help me do that, I’m bringing on my friend Greg Isenberg. Greg is one of the best business ideators I know. He has an iPhone note wi…
