Jason Fried challenges your thinking on fundraising, goals, growth, and more

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 transcript and references at: www.lennysnewsletter.com/p/ja...
Where to find Jason Fried:
• X: / jasonfried
• LinkedIn: / jason-fried
• Email: [e-mail]
Where to find Lenny:
• Newsletter: www.lennysnewsletter.com
• X: / lennysan
• LinkedIn: / 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 penname.co/. For inquiries about sponsoring the podcast, email [e-mail].
Lenny may be an investor in the companies discussed.

[@Motivation2Invest]

Love that ,"its not the Navy Seals", we are making "B2B accounting software!" 🤣

[@aki-kakko]

My favourite episode! So much respect for all the actual entrepreneurs who are producing value and not just speculating with VC/LP money.

[@fd-tg9eb]

I wish we could have like a mini documentary of the insides at 37 Signals. They sure post a lot of info on their work process through their books, videos, podcasts, but I wish I could spectate the shaping up phases, the gut decisions discussed, witness the "okay it's taking too long, let's stop this"... It's really inspiring as a company co-founder like myself where we went kinda in the middle way: no VC but business angels, no burning millions or profits but just barely breaking even... We feel that we're on a path that's not sustainable long term but it's hard to find a soft path ahead

[@christhornham]

This is the second podcast I’ve seen Jason on. I love the way he thinks. He offers such sound advice.

[@acupofwhat]

Legit dude tbh, just became a fan of this down to earth and inspiring guy. The opposite of self-happy, "kind" VC people

[@MikeLocke]

My fave podcast guest of yours. Love Jason’s entire way of thinking. It’s scary how much I’m aligned with his train of thought. Been following Jason from his Kicksology days! ;)

[@jasonfried3717]

Hey thanks! Appreciate the kind words.

[@ckhicks]

Man…talking about how sprinting over and over doesn’t work (in life or in business) was so refreshing. Great episode and thanks to you both!

[@fabioramos7261]

This episode was so eye opening! Thank you guys, it was amazing ♥️

[@user-wk4ob9is8b]

Thanks, Lenny for this amazing podcast. Great, great content and concepts from Jason, delivered with both precision and humbleness. Love it.

[@xyxxabc123098]

This is a great episode -- made me rethink/reconsider so many things re: building a company.

[@jacqueschicourel]

awesome episode , Lenny ! Jason brought to us different approaches about how to run business. Straight to the point and really mindblowing . Congrats !

[@armoproten]

Wow, thanks Lenny for this episode! I can resonate with what Jason says, 'you cannot sprint back to back to back', 'make sure to have 2 week cool downs', try to explain cool down to big corps though, they wont agree . Thanks Jason for being so honest, a trait that is rare in bigger companies...

[@ipranay]

So good! Just amazing insights and advice in this one podcast! Thanks Jason! 🙏

[@ent1c3d]

Jason was brilliant, good episode! and I also want to emphasize how good Lenny was. it's first time I watched this podcast and it was well prepared, structured, nice comments and questions.

[@digihippy]

Absolutely love this episode. More people need to build more companies like this.

[@fredthebulldog529]

I've been running my own SaaS company for 14 years now, totally bootstrapped, profitable, small team yet service a large client base effectively, and contemplating taking investment money to "scale up" as they say.....everyone makes it sound like if you aren't pushing a minimum of 30%-50% YoY growth than you are just wasting time. Every single thing Jason said resonated with me and I felt like someone was interviewing me. Every description of how he looks at work, his product, it's view of the industry, his processes, everything...... In his extra 10 years of experience over me, he has clearly learned things I'm still struggling with like whether or not to take investors. This podcast may have been the nail in the coffin and will make some VCs not very happy next week.

[@mnspkm]

Became one of my favorite episodes along with the pathless path :) "Small is not just a stepping stone, small is a great destination itself."

[@LhotseMS]

Trully groundbreaking perspective. Very much like the mindset of going with the flow.

[@alexeyhimself]

Following Jason and David since their "Getting Real" book. So much different episode compared to those with "guys from big companies"! Thank you, Lenny!

[@jasonfried3717]

Early days! Love it. Getting Real was so fun to write. Really the beginning for us.

[@Entrepreneur_in_progress]

Love this episode, full of good common sense. I have been following Jason on social media for a while, very respected entrepreneur in the industry. In a world full of fundraising stories, VC's voices, and unicorns, it is great to have people like Jason talking about the good sense of entrepreneurship and doing business in a simple, independent, and profitable way. He is a role model for entrepreneurs.

[@arseniharkunou5905]

I wish more executives & leaders would listen to Jason and try things that feel right.

[@saaimco]

Such an awesome episode, love this guy

[@pranavpalasamudram6119]

This is your best episode!

[@MikeLocke]

Half way through, this episode is amazing! Masterclass from Jason.

[@jokosi]

Ay it’s you! You were a important piece in my formative years of becoming a designer. Cool to see yer face pop up outta nowhere! :D

[@MikeLocke]

@@jokosi 🙂

[@AndrewHubbard1]

Just found your pod after this video showed up as a recommendation. Glad I did!

[@LennysPodcast]

Thanks Andrew!

[@AndrewRusinas]

30k views? wtf This is pure gold, Jason is GOAT. Thanks for this interview, I wish it was 5 times as long though haha

[@scttymn]

Fantastic episode!

[@mmayur404]

Great episode! 🎉

[@cereal_learner]

'Infinite Game' concept is also popularized in a lot of Simon Sinek's videos. Great content, have been a long time admirer of Jason!

[@LennysPodcast]

Pretty sure he ripped off the idea from this book: www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713

[@cereal_learner]

Not sure about ripping, you should definitely invite Simon on your podcast @@LennysPodcast

[@LennysPodcast]

@@cereal_learner good call, will explore that

[@fd-tg9eb]

@@LennysPodcast in his book "The infinite game" he explicitly cites it many times. Nice book to read btw.

[@dttttt]

Thank you, Lenny, for this Jason Fried podcast. This is an important conversation to have. There are different paths to financial success. I do wish other major SaaS influencers were more balanced and didn't focus so much on the VC path.

[@jasonfried3717]

The good news is while VC dominates the tech headlines, the majority of businesses run like ours - they need to fuel themselves, they have to make more than they spend, they have to make it work with their own money.

[@abdurrahmanhalis]

One of the best episodes on podcast. We couldn't hear who Jason admires tho :)

[@Eyenn_n]

Amazing episode!!

[@AlexMacGregor]

Great video/advice!

[@AnilKumarGurindapalli]

Amazing Insights..

[@preethamchangappa5362]

Gold mine of content.

[@landpro28]

Amazing show, amazing host, great guests! Thanks a lot, subscribe! 🎉

[@LWarrenF]

I worked at a company not dissimilar to this and then a few big ones. I totally understand how all the big firms can just keep letting people go. They’re an order of magnitude over staffed.

[@fraserseymour3714]

Refreshing. More than a few of us have built companies both with vc and bootstrapping and for that matter with research grants and 2 of those models demand attention to efficiency. Jason's co founder & cto David H Hansson and I share views around operating choices. Clearly Jason is very similarly aligned. Refreshing

[@shwethad6860]

My favourite! Huge Fan!!!

[@jasonfried3717]

Thank you thank you!

[@user-ib7dt4pm9y]

Jason Fried & David are the best of the best, you bet !!!!! Jason if I was in your place, I would continue being on top of my business (as part of lifestyle more like daily dose of medicine ) and would br doing more research/experimentation to generate the fresh air for me and my business and the entire eco-system around it.

[@jasonfried3717]

Very kind, thank you.

[@mclarentee]

Netflix should make a documentary on 37signals or some other successful stay-ups. In fact, 37signals shared some similar philosophies of Berkshire Hathaway :)

[@joebazooks]

the guy has a great perspective. can relate big time

[@heyderekj]

"I would not trade Basecamp for Monday's business any day of the week." -Jason WHAT A BAR.

[@jasonfried3717]

Or any business, really. Build the business you wouldn't trade for anyone else's business.

[@youssef.elmoumen]

the fact that this channel which is a treasure has only 85k subscribers while a tiktok stupid dancer has millions tells a lot about the world's population Thank you very much for bringing this AMAZING CONTENT and making it accessible for free

[@thinkingcitizen]

That’s because most people in the world are not interesting….

[@Mark1B]

A symbiotic, fair value driven enterprise model..? Fuck yeah man.

[@ShaneFontane]

this was so good on so many levels, but most of all - it demonstrates how different people and different org cultures create products differently... and that's OK :)

[@paulholsters7932]

Refreshing

[@dmbucsdavesofl]

Nice job

[@dylanjardon7136]

trust your gut 🙌

[@tomasvalent3876]

Legend 💪

[@paulholsters7932]

I am creating this developer tool for more than a year now. Am I doing it wrong then?

[@algeriennesaffaires7017]

37:00 It's not a good idea to kill hard work done by programmers, they will get tired and leave the company because your trashing their hard working, they need to see the fruits of the hard work which make them happy and excited to work on the company

[@rodrigolj]

Scrappiness has a name in Brazilian Portuguese: gambiarra

[@ry3bee]

I wonder what he thinks of Silicon Valley.

[@tigreytigrey8537]

I think to make his approach work you need to hire only the SMARTEST 1% OF PEOPLE that come pre-loaded with good "instincts". For your everday company KPIS and data are necessary for success at scale. **edit** i just listened to the rest of the podcast and he said exactly that lol. Guess i should be more patient before commenting.

[@kosmickarma29]

Jason looks like old age Mark Zuckerberg.

[@Itsweet5533]

Sounds like a prideful badge of false excellence to me. It’s better to set a strong guideline of 6 weeks without throwing away work that goes over. Accountability systems can still exist like milestone checkins and retros. Trashing everything that is delayed due to reasonable circumstances like unexpected dependencies, new employee learning curves, or pivots based on latest information is wasteful and a morale killer.

[@ChrisLad]

If this is in regard to regular goals or any type of work than what terrible advice

[@Entrepreneur_in_progress]

Love this episode, full of good common sense. I have been following Jason on social media for a while, very respected entrepreneur in the industry. In a world full of fundraising stories, VC's voices, and unicorns, it is great to have people like Jason talking about the good sense of entrepreneurship and doing business in a simple, independent, and profitable way. He is a role model for entrepreneurs.

[@jasonfried3717]

Thanks much. Nice to hear you enjoyed it.