The Crazy Ones

Episodes

Jan. 3, 2024

A 2-Step Program for New Year's Resolutions

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 …

Episode page
Jan. 1, 2024

A $20m Business with No Meetings, Deadlines or Full-Time Employees

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 p...

Episode page
Dec. 29, 2023

Startup Hotline

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 int...

Episode page
Dec. 27, 2023

Underrated Tools to Find Hidden Business Ideas

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 …

Episode page
Dec. 25, 2023

How to Crush a Quarterly Offsite

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...

Episode page
Dec. 22, 2023

How to Elevate Your Circle

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 …

Episode page
Dec. 20, 2023

Bootstrapping vs. Venture Capital

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 boot...

Episode page
Dec. 18, 2023

Lessons from Jeff Bezos

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 ...

Episode page
Dec. 15, 2023

What I’m Doing Differently as a 2nd Time Founder

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 …

Episode page
Dec. 13, 2023

How to Build a Community-Enhanced Business

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 ...

Episode page
Dec. 11, 2023

LEGO: From Bankruptcy to Brick Behemoth

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 …

Episode page
Dec. 8, 2023

Weekly Recap: An Inspirational Entrepreneur, My Convos with Allstate …

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 …

Episode page
Dec. 6, 2023

How to Avoid Meetings & Build a Great Remote Culture

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, …

Episode page
Dec. 4, 2023

13 Dangerous Psychological Biases

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 …

Episode page
Dec. 1, 2023

A Tool That Made Me 95% More Productive

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 effe...

Episode page
Nov. 29, 2023

How To Raise Capital Successfully with Dan Siroker

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). ...

Episode page
Nov. 27, 2023

How to Use EOS (Entrepreneurial Operating System) to Run & Scale Your…

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 reve...

Episode page
Nov. 24, 2023

Week In Review: Thoughts on OpenAI, Morning Rituals, and Momentum

Episode 72: Alex Lieberman ( @businessbarista ) reflects on four lessons from the OpenAI saga. He also chats about the power of saving time and making people look good, his morning ritual, and why momentum is everything in bu...

Episode page
Nov. 22, 2023

How to Delegate Effectively

Episode 71: Alex Lieberman ( @businessbarista ) talks to Jesse Pujji ( @jspujji ), founder of GatewayX and former CEO of Ampush, about delegating effectively as an entrepreneur. The two discuss powerful frameworks like the De...

Episode page
Nov. 17, 2023

The Power of Our Stories

Episode 69: Alex Lieberman ( @businessbarista ) shares a story that he told himself for nearly a decade, which made him question his self-worth and abilities despite “the world’s” perception of him as a successful entrepreneu...

Episode page
Nov. 15, 2023

How to Maximize The Value of Your Startup Equity

Episode 68: Alex Lieberman ( @businessbarista ) interviews Ankur Nagpal ( @ankurnagpal ) about maximizing your equity as a founder. Startup equity can be confusing and daunting, but it could also be the difference of millions...

Episode page
Nov. 13, 2023

How to Crush an Investor Update ft. Sam Corcos

Episode 67: Today, Alex Lieberman ( @businessbarista ) is speaking about investor updates with the most qualified guest in the world. Sam Corcos ( @SamCorcos ) is the co-founder & CEO of Levels, a healthtech company focused o...

Episode page
Nov. 10, 2023

Dear Diary: Lenses in Life, The Idea Maze, Messy Middle

Episode 66: Alex Lieberman ( @businessbarista ) recounts a day in his life as an entrepreneur, creator, and new uncle. He reflects on the lens through which we decide to observe our life, the wisdom in children, and the beaut...

Episode page