#startup #founder #entrepreneur best startup founder podcast, jason fried from basecamp, controversial opinions, business planning tips
Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss: • Why he and his team prioritize profit above all else • The unexpected challenges with raising venture capital • The “Shape Up” framework for building products • Why, and how, to foster a gut-driven culture • Jason’s thoughts on why work should not feel like war • Advice for starting a bootstrapped business • The philosophy behind Once, 37signals’s new line of software products — Brought to you by Coda—Meet the evolution of docs: https://coda.io/lenny | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny?utm_source=lennys&utm_medium=newsletter&utm_campaign=waitlist&utm_content=accelerate | Wix Studio—The web creation platform built for agencies: https://www.wix.com/studio?utm_source=Lennyspodcast&utm_medium=Podcastad&utm_campaign=SL Find the transcript and references at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking Where to find Jason Fried: • X: https://twitter.com/jasonfried • LinkedIn: https://www.linkedin.com/in/jason-fried/ • Email: jason@hey.com Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Jason’s background (03:49) The success of 37signals (06:46) When raising money makes sense (09:58) The power of small teams (13:55) Defining success and goals (17:08) Playing “infinite games” in life (20:11) Starting a business vs. staying in business (22:13) Lessons from 25 years in business (27:28) Venture scale vs. bootstrapping (30:30) Choosing the right path for your business (33:19) The “Shape Up” framework (37:59) The drawback of promises (39:56) Adopting a new way of working (41:36) The two-week cooldown (43:53) Trusting intuition and gut (46:41) Creating a gut-driven culture (49:44) What Jason looks for in new hires (56:19) Advice on making changes and adapting (01:00:06) What Jason has changed his mind about (01:02:33) Planning in 6-week stretches and figuring it out as you go (01:06:43) Being proud of the work you do (01:09:05) Jason’s thoughts on why work should not feel like war (01:11:31) Advice for starting a bootstrapped business (01:14:33) You must be at peace with the worst that can happen (01:15:42) The benefits of bootstrapping (01:19:11) The value of constraints in business (01:22:00) Jason’s philosophy: “Just keep making great shit” (01:23:19) Once, 37signals’s new line of software products (01:26:33) The philosophy behind Once (01:35:47) Closing thoughts (01:37:23) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
#startup #founder #entrepreneur best startup founder podcast, jason fried basecamp, best entrepreneur podcast, bootstrapping vs venture capital
Sign Up for "Writing Examples" and Learn From The Best Writing of All Time: https://www.writingexamples.com Get ready to swap everything you know about business-writing for an unconventional approach that actually works. Basecamp CEO Jason Fried is one of the world’s most successful software entrepreneurs. And he’s unique for the way he challenges the tenets of Silicon Valley startups. He’s bold like Bezos, but relaxed like Buffett. He cares less about “rising-and-grinding” and more about an honest 40-hour work week. He never white-knuckles his ideas, but shares them freely with the world. As a result, he’s transformed how Internet businesses are being built. And it all starts with — you guessed it — getting his best ideas on the page. His founder letters stand out (and they’re his favorite thing to write). Whenever he announces a new product, he releases a letter that does three things: builds a devoted fanbase, ramps up excitement, and sheds light on the purpose behind his products. And in this episode, you’ll learn exactly how he does it. You’ll learn specific business-writing techniques: from storytelling to structure to word choice. You’ll learn how to find your flow, make writing easier, and use writing to start doing things in the world. WRITE OF PASSAGE: Want to learn more about the next class for Write of Passage? Click here: https://writeofpassage.com/ SPEAKER LINKS: Website: https://world.hey.com/jason Twitter: https://x.com/jasonfried Medium: https://medium.com/@jasonfried Books: https://www.amazon.com/stores/author/B002MQ13PQ PODCAST LINKS: Website: https://writeofpassage.com/how-i-write Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv TIMESTAMPS: 00:00:00 Introduction 00:01:30 Communication 00:03:30 Struggle and Flow 00:10:45 Guide to Internal Communication 00:12:45 Writing a book 00:14:40 Writing like a sprinter 00:22:00 Editing 00:24:00 Mistakes and imperfections 00:33:00 Time and schedule for writing 00:36:00 Bad writing in business and school 00:39:40 Founder letters and product demos 00:45:00 Writing has to be playful and fun 00:52:15 Email 01:01:30 Writing with movement (rhythm and bounce) 01:02:00 Writing class I would like to teach (Editing and Iteration) 01:08:00 Writing in hiring employees (Resumes and Cover letters) 01:10:00 Writing company updates (“Heart beats”) 01:15:00 Writing to customers (marketing copy) 01:22:30 Sharing your secrets (chef's recipes) 01:26:40 Loosen your grip (life, business, and writing) ABOUT THE HOST: I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible. How I Write is a podcast by Write of Passage // Production by Adam Soccolich