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Bootstrapping allows entrepreneurs to increase their money-making skills and gradually improve their business. It is an alternative to the conventional "go big or go home" mentality of raising large amounts of money. Bootstrapping offers more room for success and building a profitable business by focusing on making money rather than seeking unicorn status.
37 Signals, the company behind Basecamp, Hay, and other products, stands out as a company that values profitability over seeking outside investment. They have stayed independent and profitable for over 24 years, with no plans to go public or sell. By focusing on efficiency, small teams, and simplicity, 37 Signals has achieved a significant customer base, substantial profits, and a fulfilling and enjoyable work environment.
37 Signals believes that smaller teams and constraints often lead to better outcomes. By keeping teams small, they minimize bureaucracy, speed up decision-making, and maintain a tight focus on their products and services. Constraints like time limitations and resource scarcity encourage creativity, efficiency, and meaningful prioritization.
37 Signals values intuition and gut feelings in decision-making processes. Rather than relying solely on data or numbers, they trust their instincts and judgment. The holistic experience and insights individuals bring to the table play a significant role in decision-making. This approach creates space for everyone in the company to make decisions based on their intuition and fosters a culture that values thoughtful, intuitive decision-making.
The speaker emphasizes the significance of considering emotions and feelings in various aspects of life, such as design, features, and decision-making processes. The focus is on understanding how humans feel and recognizing that, as feeling creatures, our subjective experiences greatly impact our thoughts and opinions. By prioritizing feelings and asking others about their emotions, a more inclusive and empathetic perspective can be achieved.
The podcast explores the value of trusting one's instincts, particularly in the role of a product manager. It highlights the importance of having genuine opinions and insights based on personal experiences and using them as valuable contributions to the decision-making process. The discussion dives into the challenges faced by CEOs who lack design or product-related backgrounds and suggests potential solutions like hiring experienced individuals or fostering a small, collaborative team where skills can rub off on each other.
The episode delves into the benefits of staying small as a business and the advantages of maintaining independence. It emphasizes the control and freedom that comes with being a self-funded and self-sustaining company. By staying selective in hiring and focusing on finding individuals with aligned values and unique perspectives, the company can cultivate a culture of shared influences and diverse lenses. It also touches on the value of making decisions based on pride, excitement, and a spirit of creation rather than driven by external expectations or obligations.
It is important to start as small as possible and handle most of the work yourself in order to minimize costs and avoid unnecessary expenses. By staying lean and focusing on essential tools like a reliable laptop and a low-cost website platform, entrepreneurs can keep their expenses under control and maximize efficiency.
Embracing a scrappy mindset in business can lead to better decision-making and success. Having constraints, such as limited resources, encourages innovative thinking and resourcefulness. By staying connected to the core of the business and prioritizing profitability, entrepreneurs can build a strong foundation and improve their ability to make money.
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
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Find the full transcript at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking
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Where to find Jason Fried:
• X: https://twitter.com/jasonfried
• LinkedIn: https://www.linkedin.com/in/jason-fried/
• Email: jason@hey.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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 s**t”
(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
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Referenced:
• 37 Signals: https://www.smartsheet.com/
• Basecamp: https://basecamp.com/
• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713/
• Ingram Micro: https://www.ingrammicro.com/
• Once: https://once.com/
• Basecamp’s Shape Up framework: https://basecamp.com/shapeup
• Hill charts: https://basecamp.com/features/hill-charts
• Jason Fried’s quote about long-term business planning: https://medium.com/@farkhan569/unless-you-are-a-fortune-teller-long-term-business-planning-is-a-fantasy-jason-fried-quote-a69e8778e9c4
• Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/
• Matt Mullenweg on X: https://twitter.com/photomatt
• Leo Polovets on X: https://twitter.com/lpolovets
• HEY: https://www.hey.com/
• Redefining success, money, and belonging | Paul Millerd (The Pathless Path): https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/
• It Doesn’t Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780
• Squarespace: https://www.squarespace.com/
• Stoic negative visualization: https://dailystoic.com/premortem/
• Linear: https://linear.app/
• Peter Rahal on LinkedIn: https://www.linkedin.com/in/peter-rahal-037bba43/
• RXBAR: https://www.rxbar.com/en_US/home.html
• Jason’s LinkedIn post: https://www.linkedin.com/posts/jason-fried_just-keep-making-great-s**t-keep-your-costs-activity-7130978623523614720-VBGX/?trk=public_profile
• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413
• Hell Yeah or No: What’s Worth Doing: https://www.amazon.com/Hell-Yeah-No-whats-worth/dp/1988575117/
• Home-Made: Contemporary Russian Folk Artifacts: https://www.amazon.com/Home-Made-Contemporary-Russian-Folk-Artifacts/dp/0955006139
• Oppenheimer: https://www.oppenheimermovie.com/
• Tom Petty’s “Crawling Back to You” on Spotify: https://open.spotify.com/track/1JenqZNMU6unIwVWmoP3J0
• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
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