Founder's Journal

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 & CEO of Gumroad, an e-commerce platform for creators. Gumroad does nearly $20m per year, is highly profitable, and has no full-time employees. In the essay, Sahil talks about leaving Pinterest as its second employee in 2011, to buil...

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 Gil, a successful entrepreneur and arguably the greatest angel investor in the world, and Paul Graham, the founder of Y Combinator, on spending your money wisely.  Elad Gil Essay...

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 about the very first Amazon shareholder letter written by Jeff Bezos the year that the company went public. It’s a 4 page, 1600-word letter, but it punches way above its word co...

Episode 94: Alex Lieberman (@businessbarista) takes you through an exercise to recalibrate and focus on his zone of genius. The zone of genius is work that you do that brings out the best version of yourself. Follow this super easy, super quick 3-step process to find your own zone of genius. Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #FoundersJourn...

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. Until now. Rahul Vohra, the founder & CEO of superhuman, which is the fastest email app ever, felt strongly that there had to be a better way to measure product market fit. A way...

Episode 92: Today, we’re talking about Founder personal finance. My buddy Ankur Nagpal is the Founder & CEO of Carry, a business that helps business owners build wealth in a number of ways, most notably with their Solo401k product. And he is probably the smartest person i know as it relates to tax strategies and wealth preservation tactics for entrepreneurs. So on this episode of the pod, Ankur ru...

Episode 91: I did something crazy. I convinced HubSpot to send me & 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, creative sh*t to market the brand & hopefully go viral. Here’s the story of how it happened, how we plan to go viral, and the lessons learned. Send us an email and let us know...

Episode 90: Today I’m interviewing Jason Fried who is a legendary entrepreneur. Jason is the cofounder & CEO of 37signals which is a software development company that has created popular products like Basecamp, Hey, and others. 37signals is completely bootstrapped, it’s been in business since 1999, it has more than 100,000 customers and it does tens of millions in profit per year. In addition to l...

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 take you through this program so you know how I use goal setting & accountability in unison to help maintain my direction & discipline throughout the year. EOS episode: https://...

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 platform for creators, and to break it down I chat with Sahil Lavingia the company’s founder & CEO. While the way Sahil runs Gumroad may be too unorthodox for how you run your...

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 into entrepreneurship, and more. Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entrepreneur Listen to F...

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 with literally thousands of business ideas and he has a number of go-to software tools that help him find emerging trends & ideas hidden in the corners of the internet. After lis...

Episode 85: In this episode of Founder’s Journal, I teach you how to crush a quarterly meeting. I take you through the 7-step meeting process I use (thanks EOS) and share specific examples from storyarb’s recent offsite using this process. V/TO: https://www.eosworldwide.com/blog/whats-in-your-v-to  Rocks 101: https://www.eosworldwide.com/blog/creating-the-best-rocks  Send us an email and let us kn...

Episode 84: Alex (@businessbarista) is giving you a playbook for surrounding yourself with the right people & right things in life. To achieve the ambitious goals you have for yourself you need to live a certain set of values & to live those values you need to keep a highly curated circle of connections, role models, content, and community. This 15-minute, 9-step process will enable you to do that...

Episode 83: Alex (@businessbarista) speaks to Jason Fried (@jasonfried), co-founder and CEO of 37signals, a software development company that has created popular products like Basecamp and Hey, about the tradeoffs of bootstrapping your business vs. raising venture capital. 37signals is completely bootstrapped, doing tens of millions in profit per year, with more than 100,000 customers.  Jason Frie...

Episode 82: On this episode, Alex (@businessbarista) shares the best moments from Lex Fridman’s recent conversation with Amazon & Blue Origin Founder Jeff Bezos. He also shares his reactions & analysis. These moments range from having deep self-awareness to the difference between an inventor & entrepreneur to running great meetings. Full interview: https://www.youtube.com/watch?v=DcWqzZ3I2cY&t=196...

Episode 81: Alex (@businessbarista) is talking about things you’d do differently as a second time founder. My buddy Ankur Nagpal is the Founder & CEO of Carry, a business that helps business owners build wealth in a number of ways, most notably with their Solo401k product. Prior to Carry, Ankur was the Founder & CEO of Teachable, a teaching platform for creators, which sold to Brazilian education...

Episode 80: Today, Alex (@businessbarista) is talking to Greg Isenberg (@gregisenberg), founder of Lake Checkout, a holding company that creates, grows, and buys community-based products. Alex and Greg discuss building a community-enhanced business and why it can act as an accelerator for your company.  Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #F...

Episode 79: Alex (@businessbarista) is breaking down one of the greatest brands of all time: LEGO. While Lego has become the world’s largest toy company thriving off millions of kids & grown ass men like me, it wasn’t always that way. Lego’s story is turbulent enough to make a Harvard MBA queasy. From family tragedy to factory fires to financial ruin, Lego almost died MANY times since its founding...

Episode 78: Today Alex (@businessbarista) does a true journal entry. He gave himself a simple prompt: What went well? What didn’t go well? What are you thinking about? Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here: ht...

Episode 77: Alex (@businessbarista) is talking about how to best manage a remote team & build a culture that isn’t dependent on meetings. His guest today is Sam Corcos (@SamCorcos) the cofounder & CEO of Levels, a healthtech company focused on metabolic health using continuous glucose monitors. At Levels, Sam has built a fully remote team with a culture that is defined by very few meetings and a t...

Episode 76: This episode is in honor of Charlie Munger, who died on November 28th, 2023, at the age of 99. Beyond being one of the greatest value investors of all time, Charlie Munger was often considered to be the behind-the-scenes voice of reason for his more public counterpart Buffett, and many admired him for his latticework of mental models. In 1995, Charlie gave a speech called the Psycholog...

Episode 75: This episode, Alex Lieberman (@businessbarista) shares a tool that’s made him 95% more productive, a virtual coworking site called Focusmate. Alex walks through Focusmate, and the science behind why it’s so effective. Focusmate: https://www.focusmate.com/ Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entrepreneu...

Episode 74: Alex Lieberman (@businessbarista) speaks with Dan Siroker (@dsiroker), co-founder and CEO of Rewind, who raised a $15M Series A at a $350M valuation by publicly putting his pitch deck on X (formerly Twitter). Dan received 170 offers for investments ranging from $200M to $1B valuations. In addition to discussing his highly unconventional approach to raising capital, Alex and Dan discuss...

Episode 73: Alex Lieberman (@businessbarista) talks about EOS, an operating system for running & scaling your business successfully. In 2019, Morning Brew used EOS to scale the business from 15 people and $3 million in revenue to 300 people and $75 million in revenue. Michael Girdley is an entrepreneur and content creator who has a holding company of 12 businesses that do $100m in annual revenue....