The Crazy Ones

Episodes

100
Jan. 29, 2024

Brian Chesky on Startups, Leadership, and Curiosity

Episode 100: On this episode, I’ll be sharing the best moments from Lenny Rachitsky’s recent interview with Brian Chesky, the co-founder & CEO of Airbnb. Airbnb is a $95bn company that under Brian’s leadership has grown into a community of 4 million hosts welcoming over 1.5 billion guests across 220 countries. These moments range from how politics & bureaucracy are created in a company to surviving near-business death in 2020 to how Brian has grown as a CEO since day 1. Send us an email and l...
99
Jan. 26, 2024

1,000 True Fans

Episode 99: I’m going to be reading & 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 Editor of Wired magazine & he wrote 1,000 True Fans to illustrate the ability for creators on the internet to make a very meaningful living with a seemingly small number of consumers or customers. While the essay was written in 2008, I believe it is as if not more relevant today in an age...
98
Jan. 24, 2024

25 Lessons in 25 Years

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 world’s first venture studio. Modeled after Thomas Edison’s Lab, a place where many ideas and inventions can be tested under one roof, IdeaLab went on to find 5,000 ideas, launch 150 companies, and successfully IPO or exit 50 businesses. The business hit its 25-year-mark in 2021 ...
97
Jan. 22, 2024

A Founder’s Failure to Build a Billion-Dollar Company

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 build his life’s work…a company called Gumroad that would be worth billions of dollars, IPO one day an e...
96
Jan. 19, 2024

How to Spend a Startup’s $ Wisely

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: https://blog.eladgil.com/p/capital-efficient-businesses Paul Graham Essay: https://www.paulgraham....
95
Jan. 17, 2024

The First Amazon Shareholder Letter: Summarized & Analyzed

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 count. On this episode I’m going to summarize the letter for you & share a number of timeless business...
94
Jan. 15, 2024

How to Find Your Zone of Genius

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 #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Wat...
93
Jan. 12, 2024

Measuring Product Market Fit

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 to quantify it and use it as a proactive tool to dictate how you run your business and build your pr...
92
Jan. 10, 2024

How to Optimize Taxes as an Entrepreneur

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 runs through everything from the QBI deduction for business owners to what business type (like llc, c-...
91
Jan. 8, 2024

I Did Something Crazy

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 what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entreprene...
90
Jan. 5, 2024

Musings of a Legendary Entrepreneur

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 listening to this pod I highly recommend you follow Jason on twitter, check out his blog posts (which...
89
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 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://foundersjournalpod.morningbrew.com/how-to-use-eos-entrepreneurial-operating-system-to-run-scale-you...
88
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 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 company, I have no doubt that this episode is going to push you to think more critically & creativel...
87
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 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 Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here: https://www...
86
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 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 listening to this episode, you’ll have a handful of tangible tools you can use to either find ideas for...
85
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 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 know what you think of the idea! foundersjournal@morningbrew.com #FoundersJournal #Startups #Entrepr...
84
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 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. Send us an email and let us know what you think of the idea! foundersjournal@morningbrew.com #Fo...
83
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 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 Fried Blog: https://world.hey.com/jason Send us an email and let us know what you think of the idea! fo...
82
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 from having deep self-awareness to the difference between an inventor & entrepreneur to running great meetings. 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 ...
81
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 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 company Hotmart for $250 million. On this episode, Ankur talks through all of the ways he’s approach...
80
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 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 #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV...
79
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 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 in 1929. But it didn’t. And now, Lego’s revival is considered by many to be the greatest turnaround...
78
Dec. 8, 2023

Weekly Recap: An Inspirational Entrepreneur, My Convos with Allstate & Activision, and Agency Lessons

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: https://www.youtube.com/@FoundersJournal/ Subscribe to Morning Brew! Sign up for free today:...
77
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, 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 ton of documentation so that information can be shared asynchronously across the org. If you are some...