Episode 129: On today’s episode I discuss my decision to step down as CEO of Morning Brew. I chat about going from a Chapter 1 to a Chapter 2 CEO, the emotional journey after stepping down, and climbing out of the trough of sorrows. Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here:...

Episode 128: On today’s episode of Founder’s Journal, I talk through the sale of Morning Brew. I chat about how the opportunity came about, why we said no to previous potential deals, why I thought selling the business was the right decision, and if I have any regrets reflecting on the decision today. Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here:...

Episode 127: On this episode of Founder’s Journal, I break down the exact strategies we used to acquire our first 10,000 newsletter subscribers and abstractable growth lessons you can apply to your business. Send us an email and let us know what you think of the idea! [email protected] #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...

Episode 126: Today I discuss my biggest takeaways from a Fortune 500 CMO dinner I hosted, choosing between freelancers vs. full-time employees, lessons in storytelling from Shaan Puri, the importance of following your energy, and joining the board of a non-profit.  Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here:...

Episode 125: In today’s episode I chat about being in a content creation slump, making an impact as an entrepreneur, and why you never know if it is the right time to go all in on your business.  Send us an email and let us know what you think of the idea! [email protected] #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...

Episode 124: Today we’re throwing it back with a true journal style episode. I talk about the joys of finding product market fit, being a default-trusting founder, and understanding extrinsic vs. intrinsic drivers.  Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here:...

Episode 123: On this episode, I share a recent blog post by my friend and former colleague, Tyler Denk. Tyler is the co-founder & CEO of beehiiv, a high-growth email newsletter platform. This post outlines Tyler’s philosophy on building a team and culture that allows your company to ship features at lightning speed. His insights are valuable not just for technical founders, but for any entrepreneur who wants to better empathize with engineers and product employees. Original essay:...

Episode 122: Lulu Meservey is the former Chief Communications Officer of Activision Blizzard and Substack. This episode, I read her recent manifesto, which details the importance of founders crafting their narrative, learning how to communicate, and going direct to their audiences via social media. Original essay: https://www.rostra.co/ Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s...

Episode 121: Writer, Columbia Business School grad, and college athlete Jack Raines' essay, "The Opportunity Cost of Everything," forces readers to ask themselves the only question that really matters: If I was nearing the end of my life, would I be happy with how I am currently spending my time? It is a question that any human being must ask themselves periodically, but I find that it is especially relevant for entrepreneurs. There are many external forces that can push you down the path of...

Episode 120: Andrew Wilkinson is the co-founder and CEO of Tiny, a publicly traded holding company trying to be Berkshire Hathaway but for internet companies. In 2007, Andrew started a Canada-based design agency called MetaLab, which grew to $40-50 million in revenue & $20 million in profit. After trying and failing to launch other businesses, Andrew pivoted to buying businesses to grow his holding company. I’m going to read a story by Andrew about one of the businesses he tried to launch...

Episode 119: LTV, or lifetime value, has become the gold standard for startups, specifically how they measure the effectiveness of their various marketing channels. LTV does have merit, and it is a helpful proxy to prioritize marketing and understand the economics of each customer you acquire, but if relied on entirely, it can be misleading at best and harmful to your business at worst. I’ve found what I believe to be one of the best pieces on the internet about the challenges of this...

Episode 118: Million Dollar Weekend, by Noah Kagan, the founder & CEO of AppSumo, walks you through the step-by-step process for building a 7-figure business in 48 hours. I know it sounds too good to be true, and no, you’re not going to make $1 million in 2 days, but after reading the book, I can promise you that you will have a repeatable process for going from business idea to revenue in 48 hours and understanding if it has the potential to get to 7-figures. In today’s episode, I break...

Episode 117: Just under 13 years ago, Marc Andreessen proclaimed that software would transform every industry. He couldn’t have been more right; software did eat the world. 7 of the 10 largest companies in the world today are technology or software businesses, and Andreessen Horowitz, the investment firm Marc founded in 2009, grew to become the largest VC in the world. Today, we’re going to be reading Andreessen’s 2011 essay to understand the rationale behind his future predictions, and how...

Episode 116: I found one of the best resources on hiring by one of the most well-respected founders and early-stage investors, Elad Gil. In this episode, I'll be reading highlights from the Hiring chapter of Elad’s startup book, High Growth Handbook, and cover job descriptions, interview questions, candidate scoring, work projects, building a diverse team, and more. Original essay: https://growth.eladgil.com/book/recruiting/recruiting-best-practices/ Send us an email and let us know what...

Episode 115: Today’s essay breaks down one of the best business strategy books I’ve ever read. Startup founder Abi Tunggal breaks down 7 Powers by Hamilton Helmer, which is a book about the seven proven business strategies that lead to sustained competitive advantage for companies. By the end of this episode, you’ll understand each of these strategies, why they created powerful moats, and examples of companies (like Apple, Netflix, Costco, and Tiffany & Co) that have won their market by...

Episode 114: Yesterday, Snowflake announced that its CEO, Frank Slootman, was retiring. Slootman, former CEO of Data Domain and ServiceNow, is such a successful and well-respected CEO that Snowflake's stock was down 24.5% or $17 billion. In honor of Slootman’s amazing leadership, defined by high standards and high intensity, I’m reading an article he wrote in 2018 about how he runs his companies. Original essay: https://www.linkedin.com/pulse/amp-up-frank-slootman/ Send us an email and let...

Episode 113: Today’s read is by one of my favorite startup creators, Lenny Rachitsky. The essay, How To Kickstart & Scale a Consumer Business, breaks down the seven proven strategies to acquire your first 1,000 users as a B2C startup. I’m going to read through each of the strategies, share some examples that Lenny provides, and provide some of my own thoughts on early growth. Original essay: https://www.lennysnewsletter.com/p/consumer-business-find-first-users Send us an email and let...

Episode 112: Today’s read was recommended by my buddy Sam Parr & it was written by Jason Cohen, a serial entrepreneur who has built 4 businesses, resulting in 2 exits and 2 unicorns. The essay is called Rich vs. King in the Real World & it explores Jason’s decision to sell his business, the unexpected criticism he received from friends & colleagues, and why he believes it was ultimately the right thing for him. Original essay:...

Episode 111: In today's episode, I talk about transitioning from early-stage founder to late-stage CEO. I read the essay, The second job of a startup CEO by Ali Rowghan, Managing Director at Y Combinator, the former COO of Twitter, and CFO of Disney. Ali breaks down the three distinct jobs of a startup CEO and how to go from being a stage 1 doer-in-chief to a stage 2 company-builder-in-chief. Original Essay: https://www.ycombinator.com/library/3k-the-second-job-of-a-startup-ceo Send us an...

Episode 110: On today’s episode, I am going to break down 17 startup principles by Sam Altman, the CEO of OpenAI & former President of YCombinator. The essay is called What I Wish Someone Had Told Me & as I read the piece I found myself nodding from beginning to end. Sam managed to bottle up so many thoughts & experiences that I’ve had as an entrepreneur, but never articulated in such a clear way. Original Essay: https://blog.samaltman.com/what-i-wish-someone-had-told-me  Send...

Episode 109: On today’s episode, I am going to break down & analyze an essay by one of my good friends & the super popular internet writer, David Perell. David is a prolific content creator, the founder of the super popular writing school Write of Passage, and the host of the writing podcast, How I Write. The essay I’ll be sharing is called Imitate, then Innovate, which explores entrepreneurs & creatives’ desires to be original, why imitation is core to every world-class...

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 define their market as narrowly as possible. Original essay: https://invertedpassion.com/define-your-market-as-narrowly-as-possible/ Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen...

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: https://www.profgalloway.com/tell-me-a-story/ Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal...

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 favorite startup blogs, and it talks about the importance of speed in decision making and execution when building a business. Original essay: https://review.firstround.com/speed-as-a-habit Send us an email and let us know what you think of the idea!...