Jason started making software at age 15 or 16 using FileMaker Pro. He built a database called Audio File to track his music collection because friends would borrow his tapes and CDs and never return them. He created the tool purely for his own needs and included a simple note asking for 20 dollars if someone liked it. The business model clicked when he received an airmail envelope from Germany containing a crisp 20 dollar bill.

That was the moment it all clicked for me, which is make stuff for yourself. There's probably other people out there like you who want what you want, and make it available to sell.

The core philosophy is that the creator is the target audience. People are not as unique as they might think. There are always others who share specific tastes and needs. By keeping costs low and the company small, a creator does not need to appeal to the whole world to be successful. It is much easier to find a few thousand people who love what you do than to try to please everyone.

I don't need the whole world to like what I like. I need enough of a small world to like what I like, and we're golden.

A business is fundamentally simple: you must make more than you spend. While external competitors exist, they are not the primary concern because their actions are outside of your control. You cannot dictate their pricing or products. Instead, the real competition is your own costs. As long as you maintain a profit, you can stay in business and continue doing the work you enjoy. This focus on costs is a common trait among history's most successful entrepreneurs, from Sam Walton to Bill Gates.

Your only competition is your costs. A business is very simple. You got to make more than you spend. That's a business, basically. What I can control is how much it costs me to run my business and how much I sell my product for. As long as I make more than I spend, I get to stay in business.

Maintaining a lean organization is essential to controlling these costs. Small teams often work better because they minimize the risk of miscommunication. Companies rarely suffer from a lack of communication; instead, they struggle with miscommunication that occurs when there are too many layers of people. Jason explains that 37signals keeps teams very small, often just one programmer and one designer working on a single feature. This constraint forces the product to remain simple and clear, which is what customers actually want.

I don't think companies really have communication problems. They have miscommunication problems. When you have too many people and too many layers and someone misses this and someone has to repeat something that happened, I want to avoid all of that. I actually think too many people get in the way oftentimes, and you actually end up making worse stuff the more people who are involved.

This philosophy extends to management as well. Jason and his partner David found that adding middle management or roles like a COO often led to people doing unnecessary work. When a role does not have enough meaningful tasks, it leads to professional dissatisfaction. By keeping the executive team small and the overall headcount tight, the company avoids the fat that often plagues larger software firms.

Adding extra layers of management often creates a game of telephone. At 37signals, engineering managers were once placed between the CTO, David, and the people doing the work. This structure caused ideas to get lost in translation. After trying these roles for about a year, it became clear that the extra levels were not helping the organization. They also tried having a COO for three years before realizing it was not the right fit for their style of working.

The question we ask after the first year with any new employee is, knowing what I know now, would I hire them again? And that answers pretty much every question. It answers every question about performance, about attitude, culture fit, and all the stuff.

This approach treats the second year of employment as a rehire rather than a simple performance review. The same logic applies to the existence of the job itself. Jason explains that they ask if they would create the position again knowing what they know now. When the answer was no for certain management roles, they eliminated those positions and never rehired for them. This allowed the company to return to a smaller, more direct size.

Every five or six years, Basecamp undergoes a process of reinvention. While early transitions involved total rewrites from scratch, current versions focus on revisiting fundamental assumptions about how the product works. There is a constant effort to buck the human tendency toward expansion. In the physical world, limits like heat or fragile materials provide immediate feedback on whether a design is good or bad. Software lacks these physical constraints and is infinitely malleable. Without something pushing back, software often expands forever and eventually gets worse.

In software, you don't get that. Software can be anything. It's infinitely malleable. And what ends up happening is because there's nothing pushing back, it just expands forever and gets worse. Software slides downhill. It gets better for a while than slides downhill.

The real challenge is making sure every new version is simpler in fundamental ways than the previous one. Even if a product gains more features, the experience should ideally become simpler. Jason finds this process fun because it is a difficult puzzle that requires pushing back against the forces of nature. It forces a creator to understand what a product really is at its core. The most rewarding part of building software is the moment of insight when a simple solution to a complex problem finally reveals itself.

Consistency is often overrated in professional life. It is more valuable to focus on context rather than trying to be consistent for the sake of it. This perspective leads to a lack of long term planning. Instead of following a rigid map, it is better to make things up as you go and react to the current situation.

I don't find consistency interesting in any way, shape or form. To me it's all about the context. Which is why I don't like to plan. I don't have long term plans. I like to make things up as I go.

Many people assume that a successful business owner loves business in general, but that is not always true. Jason enjoys running his own company because he has figured out how to make it work for him. However, he has no interest in running another company or being a serial entrepreneur. He believes that a business is a product of specific timing and having the right people at the right time. He does not feel the need to prove his success again in a different setting.

The sense of just being comfortable with what you've built and what you're working on now being enough is for me a very peaceful place to be.

The tech industry often focuses on growth, high valuations, and starting over repeatedly. This cycle can be boring and exhausting. There is a quiet power in reaching a point where what you have built is enough. Jason values the peaceful place of being comfortable with his current work rather than seeking to stroke his ego by building something new just to prove he can.

Jason has no sense of envy regarding other people's businesses. He would not trade his company for any other in the world because any other choice would feel like a downgrade. He purposefully built the specific company he wants to work at. Since it is a perfect fit for him, he has no desire to wear someone else's clothes or live up to someone else's expectations.

I built the company I want to work at. I built the business I want to be in. No one else has that. I have that. That is my thing. I love what I have built. It is a good fit for me. I do not want to wear someone else's clothes. I do not want to do someone else's stuff. I do not want to live up to someone else's expectations.

When a business is built to suit someone else's way of doing things, it becomes a game of charades. Many people fall into the trap of playing entrepreneur rather than building something that is authentically their own. Doing things your own way is the only way to avoid the need to perform for others.

Jason distinguishes between two sides of a business: the envelope and the letter. The envelope represents the shell or the vehicle that holds the product. The letter is the actual product itself. Many people spend their time on envelope work by focusing on brand identity, logos, and valuations before there is any substance inside. This approach often treats a business like a financial instrument rather than a way to make things.

I'm a product guy. I love product. That's all I care about. The business side just has to exist to hold the product. That's the vehicle in which the product travels in. But I don't care about the envelope so much.

A business should be a thin shell. In physics, the more massive an object is, the more energy it takes to change its direction. A thick business is heavy and hard to change. It creates too much distance between the organization and its customers. Jason prefers a model where the product is thick and solid while the business structure surrounding it remains as thin as possible. This allows for more agility and a closer connection to the people using the product.

The goal of a business should not necessarily be a hockey stick growth chart. A better metaphor is a rocket reaching orbit. A company must work hard to break free of gravity and the forces holding it back in the early stages. Once it reaches orbit, the goal should be to maintain that position and find a comfortable range of fluctuation. Constant growth for its own sake often leads to the question of why a company needs to be twice as massive as it already is.

You gotta be on the ride up to break free of all the forces that are holding you back. But then you should also find a place where you can settle in, in orbit versus people who I think are just busy constantly trying to grow, grow, grow.

Many business leaders feel pressure to optimize every metric, from pricing to conversion rates, but Jason argues that this focus often leads to diminishing returns. He admits to leaving money on the table by not constantly A/B testing or following growth formulas. When faced with the idea that he could be making more revenue, his response is simply "so what?" He values a predictable, high-margin business where the team enjoys the work more than the pursuit of an extra few percentage points in growth.

I think people fuck it up all the time. You get to the right size and for whatever reason, you can't be content there, and you push a little bit too much too hard, and you lost what was great about what you were doing.

There is a distinction between optimizing for numbers and optimizing for quality. Improving a product is a worthwhile endeavor because it provides a better experience for the customers and the creators who use it. In contrast, squeezing extra money out of a successful business feels boring and unnecessary. Jason accepts that a different CEO might be able to double his business overnight, but he remains uninterested in that outcome if it compromises the joy of the work.

There's a point where you're doing well enough where it shouldn't matter anymore. Now, that might make me a bad CEO. Maybe someone else would come in my business and double the business overnight. That might be totally true. And I'm willing to accept that that's the case. My answer would be, so what? I don't care.

The traditional title of CEO often feels disconnected from the actual work of a company. Rather than acting as a high-level executive, the focus should be on making decisions, building products, and hiring great people. Maintaining humility is a core part of this approach. Even when products are good, there is always room to make them better. Staying grounded often means doing work that others might consider a poor use of an executive's time, such as personally answering hundreds of customer emails.

Yesterday I answered like 200 emails from my customers. Some people would say that's irresponsible for a CEO to spend their time emailing customers. I think it's the best thing you can do.

The goal is to reduce the distance between the leadership and the customer. This distance is like the thickness of an envelope that needs to be as thin as possible. When leaders only talk to other executives, they often hear only what they want to hear. Historical examples like Jim Casey, the founder of UPS, show the value of this. He would stop his car to talk directly to drivers on the street to get the real story. Keeping this direct connection ensures that decisions are based on reality rather than filtered reports.

Jason values the personal connection found in small businesses, like a local grocery store owner who knows every customer. Because he cannot physically meet every user, he includes his personal email address and signature in the initial letter sent to everyone who signs up for Basecamp. He avoids using AI or assistants to filter these messages because he wants to hear from customers directly. This access helps him understand the language they use and how they interact with the products he creates.

Whenever you sign up for Basecamp, the first thing you see is a letter from me with my email address with my signature and my email address, and I want my customers to email me. I don't want to hide from anybody. There's no AI, there's no assistant. There's no levels between it all. Just write me.

Large corporations often feel like abstract concepts rather than real entities. Jason prefers businesses with a scale he can fully comprehend, such as a local dry cleaner or a small shop. This philosophy influences who Basecamp serves. He focuses on small and medium sized businesses because they are relatable and grounded. This appreciation for limits is illustrated by a sandwich shop called Vinnie's in Chicago. The shop follows a simple rule of craftsmanship: they stay open only as long as they have fresh bread.

The sandwich place is open as long as they have bread. And they just sell out and they're closed, that's it. They're done.

There is something poetic about a business that closes its doors once they sell out of their product for the day. A bakery might close early because they have sold enough bread. They could stay open later to make more money, but that path has no clear end. A business can easily consume an owner's entire life until they no longer enjoy it. Setting a limit allows the business to stay healthy and last longer. This prevents the owner from getting bored or burnt out.

I can understand the appeal there for a while, but I also think there is something very simply beautiful about enough.

Jason values longevity over rapid financial gain. If given the choice between making the same amount of money in fifteen years or twenty-seven years, he chooses the longer path. To him, money is a side effect of the work rather than the primary goal. He believes that the reward for good work is simply the chance to do more work. Staying in business for a long time allows a team to enjoy their craft and maintain control over their quality and messaging.

The beauty about this for me is that somehow we have managed to build this system, this company, these products that sustain over a long period of time that allow us to enjoy our craft and our work.

Quality products often reflect the quality of the company and people behind them. Jason often judges a company by looking at their output. For example, he views the Concept 2 rower as a great product. This suggests the company behind it is likely excellent as well. If someone can create a great product, they are usually an interesting person.

Jason admires the Concept 2 rower as a nearly perfect product. It is durable and affordable. It stays under a thousand dollars. The machine uses a simple black and white screen and runs on basic batteries. It does not need a plug or a recharge. This simplicity makes it incredibly reliable. It does exactly what it is supposed to do and nothing more.

Like a paperclip and a Concept 2 rower. It is hard to improve on both of those things. I have deep admiration for that kind of thing.

Jason prefers to plan on a day to day basis. He finds long term planning to be confusing. Many people try to plan three years in advance but are afraid to figure out tomorrow when it arrives. He uses the metaphor of a squirrel to explain his approach. A squirrel runs across a field with a general direction in mind. It scurries, stops, and looks around before moving again. It does not need a perfect map. It just needs to know roughly where it is headed and then course correct along the way.

The squirrel knows where it wants to go roughly. It runs and it scurries and it stops and it looks around and then it scurries some more. It knows roughly where it is headed and then it course corrects. That is how I do it.

At his company, they typically plan only six weeks in advance. Most projects take six weeks or less. They recently left the cloud to run their own data centers. That was a rare large project. For almost everything else, they set a general target and let the teams figure out the details. Jason believes this is the most honest way to work. You always know more about a situation the closer you are to it.

It is difficult to predict what will happen weeks into the future. Planning for five Fridays from now is much harder than planning for tomorrow. Focus on getting the next day right and making the right decisions for the immediate future. By making small decisions every day, you can navigate your way forward without the pressure of high stakes choices.

Let me worry about tomorrow. Let me nail tomorrow. Let me get tomorrow right. Just make small decisions all the time and do not put yourself in a place where you are making huge ones you are afraid of. You can get wherever you want to go.

Making small, consistent choices prevents the fear that comes with massive decisions. This iterative approach allows for steady progress over many years. Jason suggests that this method has been effective for over 27 years.

Many people ask about five year plans and future success. Jason finds these questions difficult because it is impossible to know who you will be in the future. People usually answer based on their current self rather than their future self. It is better to focus on the immediate present. A great life is really just a long string of great days. If you focus on making the next 24 hours successful, the long term results often take care of themselves.

People answer those questions today for who they think they are going to be. You do not know who you are going to be then. It is a silly thing to answer or even to ponder.

Jason believes that passions find you rather than you finding them. This idea comes from a conversation with Jeff Bezos. It is important to stay open to how the world presents itself. Interests change over time. You might love your current work now but find a new interest in ten years. It is okay to change your path when your interests shift. Being open to the world allows new passions to arrive naturally.

Breaking work and life into small units is a helpful strategy. A day is a perfect small unit. If a day goes poorly, it is over quickly and the damage is minimal. Large decisions are much harder to manage. They often involve many people and complex plans. If a big decision fails, the consequences are difficult to handle. Small units allow you to take risks without high stakes. Success comes from accumulating enough good small units over time.

Make things small, tiny little units that you can throw away. It does not matter. What you basically want is enough good units in a year.

Success is often built from small units rather than one giant plan. By focusing on doing enough good little things, you create a foundation that is resilient to failure. If one small piece goes wrong, it does not matter because it is easily discarded. This approach makes a business antifragile because minor setbacks cannot throw everything off course. It is about building with bricks rather than trying to create the entire structure at once.

Small units, bricks build that way. And I think that you just become more antifragile in that way. When you are just doing little things, they cannot throw you off too much if you get something wrong and it is small.

Jason suggests that we should stop worrying about missing out on massive opportunities. If you can keep your business running and focus on the work you want to do, you do not need every big chance that comes along. The goal is to make the current project work repeatedly instead of constantly looking for something bigger.

If I can stay alive doing the thing I am doing and running the business I want to run, I do not need the other big opportunities. Stop worrying about all the other things you can maybe do and just focus on the thing that you are doing and make that work over and over as long as you want to do it.

Jason explains that he intentionally avoids paying attention to what others in his industry are doing. He believes that when people watch their competitors too closely, they start to believe there is only one way to build a product. This leads to a fear-based approach where companies feel they must match every feature their rivals launch just to maintain parity. Instead of looking at other software, Jason finds inspiration in things like physical products, nature, or architecture.

I'd like to take inspiration. If I'm going to take inspiration from anything product wise, it is going to be outside my world. It is the Concept 2 rower. It is not another piece of software. I am not inspired by their software. I like buildings, I like furniture. I like watches. I like other things outside of my world that I can admire and understand and get fired up about.

By distancing himself from the software world, Jason avoids the trap of following the crowd. He suggests that being in the industry is enough exposure to it. To stay creative and energized, he prefers to spend time in nature rather than immersing himself in a competitor's product. This external focus allows for a more original perspective when it comes time to work on his own business.

I am getting enough of the software world by being in it. I do not want to soak in it. I want to soak outside of it. And then my only soaking in the software world is my own stuff. That is enough. It is enough for me to focus on.

There is a unique beauty in things that evolve on their own without being influenced by external forces. This concept is similar to how species evolve on the Galapagos Islands. Jason views his company as an insular group that focuses on solving problems in its own way. He intentionally avoids seeking out ideas from other companies because it leads to a slippery slope of copying. Many products in the software industry look and work the same because companies follow each other's successful designs.

I do think of us as an insular group focused on solving a problem our own way without paying too much attention to what everyone else is doing. I am aware of it because I live in it, but I am not seeking out ideas from other companies in our field. I think that that is actually a slippery slope.

Basecamp and Hey are designed to be different from everything else on the market. This includes the landing pages, which are often structured as personal letters explaining why a product exists. Jason handles the writing himself and aims for a style that has rhythm and momentum. He wants the words to land with meaning without being sterile. This philosophy extends to product demos. Instead of highly polished videos, Jason records long and unedited demos. If he makes a mistake, he keeps going to maintain a real connection with the audience.

We are who we are. We represent ourselves as we are. We are not a corporate entity hiding behind a structure. We are not a CEO or a CTO hiding from our customers. It is just us running the show. And the show is open for anyone to see.

The company operates without a board of directors or complex corporate structures. This allows for a direct relationship with customers. They also choose to open source much of their work and share their knowledge openly. While some potential customers might find a small and direct team less trustworthy than a large corporation, Jason is not interested in using traditional marketing language to convince them otherwise.

Jason prefers an honest approach to business without using tricks. He believes in showing exactly what a product does and letting people take it or leave it. This commitment to authenticity extends to how he views mistakes. He recalls a visit to a gallery in a small Wisconsin town where he met a collector of Navajo rugs. These rugs often contained visible errors, like imperfect geometric shapes or stitches that were clearly off. The collector explained that the Navajo do not view these as mistakes. Instead, they see them as a record of a moment in time.

If you are walking on a path, if you are climbing a mountain and you trip or you stumble, you don't start back. You can't take that stumble back. It just happened. The Navajo leave these in their rugs because they just happened. This is a record of what happened.

Jason finds beauty in this philosophy and tries to apply it to his own work. While he does not intentionally leave typos, he is comfortable leaving minor errors in videos or other content because that is how things happen in the real world. He argues that many companies are now governed by fear, relying on PR teams and lawyers before they say anything. This fear prevents them from being human. Ultimately, people want to do business with other people rather than sterile, perfect corporations.

There is a unique aesthetic value in directness and thin organizational structures. A company of 62 people where everyone is accessible and reachable feels more human than a large corporate entity. This approach mirrors an architectural concept where native village buildings, though not designed by professional architects, possess a high quality because they are a perfect fit for the people who use them. Building a company to be a perfect fit for the people running it is a sustainable business model because there are always enough people out there with similar needs.

I think conceptually, the idea was you can go see buildings in native villages, and there's no architect that made any of this stuff. They had people making places for them to live and work and worship. And there's a certain quality to that which is not textbook high quality, but is beyond high quality because it's a perfect fit for what they wanted for themselves. That's the kind of stuff I like to build.

Authenticity in business and media often comes from refusing to put on airs. In podcasting, listeners appreciate hearing mistakes and false starts because it makes the speaker more endearing and relatable. For example, rather than faking a French accent or editing out mispronunciations of foreign names, it is better to admit lack of knowledge and move on. People care about the core story and the person telling it, not superficial perfection. The key is to identify what actually matters in a product or a story and ignore the rest.

Jason often writes landing page letters in the middle of a project rather than strictly before or after. For the email service Hey, he wrote the letter months before the product was finished. This narrative approach helps clarify the mission while the work is still in progress. People often buy products not just for their utility but as a way to support the creators they have learned from over the years. This form of identification makes the act of purchasing a way to give back to the person behind the idea. In these cases, the use is the support itself rather than the actual use of the product.

I wrote this letter about why email is a beautiful thing. For the longest time people have hated email because it has gone off the rails. Do you remember when you used to get an email from someone you loved? It is a wonderful thing to get an email from someone who you care about. The problem is that most emails now are spam and sales and garbage.

There is a specific kind of love involved in the creative process. It is the feeling of satisfaction that comes from looking at a product before anyone else does and feeling truly happy with the result. When a creator is happy with their own work before it reaches an audience, that represents a version of love for the craft. This personal connection ensures that the final output carries a sense of care and intentionality.

Jason finds deep pride in the products he builds rather than the business itself. He views the business as an envelope that contains the work, but the products are what sustain it. When someone is truly proud of a finished creation, a certain warmth comes through in the final result. This feeling applies to everything from a single well placed word to an entire software platform.

The business again is like the envelope. I'm not proud of the envelope. Proud of the things that sustain the business, which are the products. And I just, I love getting them as right as I possibly can.

The decentralized nature of email and the web is a modern miracle. These systems allow anyone in the world to connect regardless of which company made their software. Jason argues that big tech companies like Apple and Google neglected email for years, which caused people to despise a tool that should be celebrated. His work on the email service HEY was intended as a love letter to the medium because he wanted to use a tool he could actually love.

Jason identifies as a toolmaker rather than a member of the tech industry. He views software as a lever that helps people move more things and make progress. While he uses code and design instead of wood, the goal remains the same. A tool is a device that allows a person to achieve more than they could on their own.

I'm not a tech person. I make tools. They just happen to be made of software. That's all I know how to do. I don't know how to make things out of wood, but I know how to make things out of software and code and design and conceptual ideas.

Physical objects offer a sense of reality that digital numbers on a screen cannot provide. Even highly successful software founders often find their most fulfilling work in physical tasks like building a stone wall. Unlike digital products, physical creations persist in the world. You can return to a wall decades later and see the tangible result of your labor.

Jason values the tactile nature of the physical world. He prefers things he can touch and hold. While software is often flat, he tries to bring simulated texture into his digital products to make them feel more real. Physical materials like brick have a unique beauty because they develop a patina as they age. Software does not age gracefully in the same way. It might look dated, but it does not collect the character that a physical object gains over time.

I like patina. I like age on things. Software doesn't age. I mean, it does age. It can look old or whatever, but software looks the same over time. A great building, a great brick. Bricks are beautiful because they look even better as they get older. They collect age on them.

Nature serves as the ultimate source of design inspiration. Many designers look at books of logos or business cards for ideas. However, the best color palettes and patterns already exist in the natural world. A leaf or a bird displays colors and forms that have evolved over millions of years. Looking at a tide pool or the way light reflects off the ocean provides better insights than any corporate identity manual.

If you want to find great colors, look at a bird. Don't look at a book. Look at a leaf. Look at the ocean. Go to a tide pool and just look at the colors in that tide pool. Look at the way the light reflects.

Jason describes a deep appreciation for the physical world that often outweighs his connection to software and screens. While he finds computers to be perhaps the most amazing tools humans have ever created, he does not feel they are necessary to survive his days. If he were to step away from his business, his first instinct would be to close his laptop for an entire year and stop computing altogether.

I don't need a screen to survive my days. I'd like to close my laptop for a year and just not use it. I'll use my phone because I get in touch with people, but I don't want to compute. I don't need to compute. Let me just close it and walk away.

This desire for the tangible stems from the belief that being disconnected from nature is far more harmful than being disconnected from technology. Jason notes that while the current era of computing is as exciting as the early days of the web in the 1990s, he would still prefer to spend his time on physical tasks like working on a stone wall. He acknowledges the practicality of his career in software, which has provided financial security, but he remains drawn to the fundamental reality of the outdoors over the digital environment.

Christopher Nolan prefers to live in an analog world. He creates advanced films but does not carry a smartphone or use GPS. When he wants to cast someone, he hand-delivers a physical script and waits for them to read it. This commitment to physical interaction over digital convenience is a choice that reflects his personal philosophy.

Jason and his host find common ground in this approach. They both build digital products but choose physical books and in-person conversations for their personal lives. Jason points out that the specific choice of being analog is less important than the self-awareness it represents. Many people do not actually know what they like. They follow the expectations of others or run their businesses based on what they think is required.

It is good to figure out what you like eventually. A lot of people don't know what they like. They like what other people like. They like what they're supposed to like. They live up to other people's expectations. They kind of run someone else's business in a sense.

Finding what you are truly into is a wonderful thing. It allows you to stop making decisions based on what others might do. Your preferences might change over time, but the goal is to have a sense of who you are and what you are all about right now. It is okay to enjoy high-tech work while maintaining a low-tech personal life.

Individual taste is deeply personal and should be respected. Whether someone loves digital or physical things does not matter because everything exists on the same speck of dust in space. What matters is that people recognize what they like and treat themselves to the things they find beautiful. There is no need to understand why something is appealing, only that it is. This appreciation for beauty and personal preference is a significant part of the creative process.

It doesn't really matter what you like and why you like it, just that you do and that you know that you do. You don't even know why that you do, but that you do and you respect and treat yourself to those things that you find beautiful.

Trusting your own judgment is a vital skill for a creator. Designing products for yourself first is an early indicator of this comfort. By being the first user and creating something that satisfies your own standards, you demonstrate a high level of confidence in your own vision and taste.

Jason believes that knowing who you are is an ongoing process. He feels he has only truly come into his own recently, particularly after getting married and having children. In his younger years, he felt like a punk with a chip on his shoulder. This attitude served as a form of fuel during the early stages of his career when he felt he had to prove himself to others who doubted his abilities.

The only time I'm ever competitive is when someone slights me. Otherwise, I'm not competitive. So for whatever reason, if someone's like, you can't do that, or you guys aren't good enough. I love when someone says you can't do something.

This drive helped him navigate his early career as a web designer. When a prominent designer told him his work was poor and he should find another job, Jason felt energized rather than defeated. He enjoys the challenge of being underestimated. He compares it to being a shorter player on a basketball court who surprises people with his skill.

While Jason found clarity and a sense of settling into himself in his 40s, he notes that psychedelic experiences played a role in that transition. However, personal history often dictates one's comfort level with such substances. Resistance to drugs can stem from witnessing the negative impacts they have on family members. For those who have seen the consequences of addiction firsthand, maintaining a clear mind is a priority.

Finding a new insight is a favorite part of life, and experiences with psychedelics can offer an avalanche of them. These experiences reveal that the mind can perceive and understand things in entirely new ways. For example, an idea is usually thought of as an abstract concept. However, it can appear as a three dimensional object that can be turned around to see what is behind it. This is not just about having a different perspective but literally seeing the other side of a thought.

You think of an idea and I never thought an idea was like a three dimensional object that I could turn around and see from the other side. Not like a different perspective on an idea, but literally I could turn it around and see what was behind it.

This expansion of awareness is similar to an old car radio from the 1950s. Most of the time, a person is tuned into one specific channel, like a needle fixed on a single frequency. Turning the knob allows a person to pick up other things that are always present but usually impossible to hear. These experiences do not necessarily provide a single breakthrough for knowing oneself better, but they add new lenses to the way the world is viewed.

You have to picture an old car radio with a needle and you move the dial. You are in one of the channels. That is where you are all the time. Turning the knob lets you tune into something else that has always been there, but you could not hear that frequency.

One specific realization involves the nature of complex problems. Many things look complicated from the front, like a difficult puzzle. However, turning a problem around to look at it from the back can reveal that it is actually quite simple. The front of something is often a facade, while the back represents what is real. Learning to get behind an issue to see what it truly is can be a valuable way to simplify the world.

Jason finds a deep connection to the ideas in Rick Rubin's book, The Creative Act. He views the world as having a natural intelligence that exists outside of our own brains. This worldview leads to a philosophy of business where you make things up as you go and follow the natural flow of events. It is about trusting your intuition and being comfortable with not knowing everything.

I am a fully intuition and gut driven entrepreneur. And I don't even love that word entrepreneur. I make products. There has to be a business around it. I run the business, but I'm gut and intuition driven. I don't look at numbers. I don't care about the numbers as long as we're profitable.

By focusing on the product rather than just the business metrics, Jason stays true to his creative instincts. He believes there is something honest and real about letting things happen without always needing to explain why. As long as the business stays profitable and healthy, the specific numbers are less important than the quality of the work and the strength of his gut feelings.

A business needs a certain amount of "blubber" to survive and thrive. This refers to having a significant margin of safety through high profit margins and cash reserves. This cushion allows a company to make mistakes without facing total failure. Running a business with razor-thin margins creates a constant fear of error that stifles growth. It is important to take risks, but those risks should never put the entire foundation of the company at stake. If a leader finds themselves in a position where they must bet the farm, the business is likely already in serious trouble.

I don't want to run a very tight margin business where I can't make mistakes or I'm afraid of them. I believe in cushy margins so we can screw up and it won't matter that much. We take risks, but we don't put ourselves at risk. I'm not interested in betting the farm.

Cost management is a primary focus for staying in business. Jason emphasizes that because the company does not take outside funding, every dollar saved is their own money. This perspective leads to practical decisions like moving off the cloud to save millions in infrastructure costs. It is often irresponsible that many software companies lose vast amounts of money despite producing a product with almost zero production costs. By avoiding unnecessary spending on things like massive marketing campaigns, a company can preserve its capital and use it to fund experiments.

A business needs fat reserves to survive lean times. While having a low body fat percentage might look good, it is not sustainable for a long period of time if you get stuck in the wilderness. Jason emphasizes the importance of having fat on the bone to weather events like the 2008 financial crash or the pandemic. Without those reserves, a company has nothing to burn when the market turns.

The blubber helps you stay in business. It is fat reserves. You should have those. If you are stuck out in the wilderness for a while, you need to burn something.

The company operates as an LLC, which allows for a simple and transparent profit sharing model. Every year, 10% of profits are distributed to employees based on longevity rather than seniority or job title. This means a customer support representative who has been with the company for a decade receives the same bonus as a principal engineer with the same tenure. Jason believes this real cash is far more valuable than the stock options or RSUs common in the tech industry, which often end up being worthless.

Our bonuses are based on profits. We have been profitable for 27 years and they are distributed every year. And they are meaningful. About 20 out of 62 people last year received six figure bonuses. It is real cash. That is the beauty of a simple business.

The goal is to provide employees with real cash that they can use for immediate life needs. This includes down payments for homes, college tuition for their children, or savings. Instead of abstract or speculative compensation, annual cash distributions offer tangible value that people can spend however they choose.

I want to pay people with real money they can actually put as a down payment for a home, pay for the college education for their kids, go on vacation, sock it away, whatever they want to do. This is real cash on an annual basis.

Supporting this model requires a business with sound fundamentals. The company must maintain high margins and high profits to ensure there is enough to distribute. Choosing an LLC structure facilitates this, as it allows for the annual distribution of profits to the team.

Jason explains that he avoids looking back at his past or conducting business post-mortems. To him, the past is a story we tell ourselves that is likely inaccurate and influenced by countless factors we no longer remember. In business, companies often spend significant energy analyzing why a project turned out a certain way. However, it is nearly impossible to know the exact reason something happened because the world or the timing could have changed the outcome entirely.

If you want to find certainty, you're going to find it because you'll convince yourself of it. I just don't have any interest in looking back. I'd rather learn by doing something again, making more things.

While many people believe we must learn from our mistakes, Jason argues that true learning comes from moving forward and taking action. You cannot redo the past, so the best way to grow is to identify what did not work and simply avoid it the next time. This forward-looking mindset prioritizes the creation of new things over the retrospective search for certainty.

A negative inner monologue and constant self criticism are common struggles for many people. Rick Rubin offers a perspective that reframes how we view our past efforts. He believes that you could not have done anything different than what you actually did. If a project could have been better, you would have kept working on it. Once a piece of work is finished, it is a reflection of that specific moment in time. There is no reason to be critical of it because you already did everything possible to make it the best it could be.

I've done everything I can to make it the best it can be. I can't do more than that. So there's nothing to be critical of. It's almost like a diary entry. Everything we make is a reflection and a moment in time.

Jason aligns with this philosophy. He views his work as a series of actions that are now part of history. This mindset is why he avoids setting arbitrary revenue or user targets. Personal pride and the enjoyment of the craft should drive the quality of work rather than a number on a spreadsheet. If you take your work seriously and enjoy the process, you will naturally do the best you can. A target cannot force you to do better work than your own internal standards already require. For Jason, the product itself is the only measurement that matters.

The target is the work I'm doing now. That's the best I can do. I don't need something to try to tell me that I could do better had I aimed for some target. The product is the measurement, not the number.

Money is the byproduct of making something good. It is not the primary reason to create. People often search for certainty in business, but it is rarely found. While a mechanical problem on an assembly line can be traced to a specific machine, business success is different. It involves a complex mix of decisions, timing, market conditions, and even the mood of the founders. Trying to pinpoint exactly why something worked creates a dangerous illusion of knowledge.

I think that is actually an important thing to say. It is like maybe you do not know why it actually succeeded. I think that is true. You do not know why it did not work, and you do not know why it worked. I really think that.

Jason notes that he could not start Basecamp again today. Many entrepreneurs sell a successful company and assume they are naturally good at building businesses. They often fail on their second attempt because they do not truly understand why the first one succeeded. Success is frequently just lightning in a bottle. It is almost impossible to build a successful company, yet many people mistake luck and timing for repeatable wisdom.

The founder of Trader Joe's serves as a cautionary tale for those seeking an exit. He built a unique, differentiated product with his whole heart. He eventually sold the company because he was afraid of the future. Although he spent the following decades investing and consulting, he ultimately admitted to a deep regret. He realized he should not have sold the company he loved because his identity and passion were tied to that specific work.

Many people build a successful business early in life and spend the next several decades trying to repeat that same height. This often leads to regret because most people cannot reach those levels again. Even if they build something great later on, they may not see the value in it because it is not as successful as their first project. This creates a tragic outcome where incredible achievements are viewed as failures by the creator and others.

Jason and his partner David use negative visualization to prepare for the future of their company. They consider what would happen if AI changed the software landscape and ended their business in a few years. Instead of feeling bitter, they choose to be proud of their long run. Jason admits he would not start another software company from scratch if his current one ended. He no longer has the same hunger or stamina he had as a young pioneer.

I wouldn't want to try to do this again because I don't think I could. I think it is totally fair to admit that I don't think I am good enough again to do what I did before. I don't have the stamina. I don't have the drive. I don't have the thirst and the hunger to build a brand new software company from scratch again.

A mature perspective involves recognizing that some magic belongs to a specific time in life. Bob Dylan once noted that he could not write the same kind of music he wrote in his youth, but he could do other things now. This is a healthy way to view a career. If your identity is tied strictly to being an entrepreneur, you feel forced to keep starting businesses to maintain that image. This need for continuity can lead to deep disappointment if you cannot reach those previous heights again.

Many people feel a sense of disappointment after major achievements, like selling a business. They often fail to see the incredible nature of what they accomplished in that specific moment. Every period of time is a unique experience that exists on its own. Jason shares a personal story about using mushrooms to illustrate this point. During a session, he asked his guide to play a song that had previously triggered a profound moment of learning. He wanted to recreate that feeling, but when the song played, nothing happened. The experience was empty.

Of course you cannot have the same experience again. You cannot have the same experience twice. You don't deserve the same experience twice. It's not even possible to relive something again. That thing happened then and this is now. They're detached, they're separate, they can never be the same.

This realization changed how Jason views his life and his children. His kids are currently 11 and 7 years old. He knows that once his son turns 12, the experience of having an 11-year-old is gone forever. It is important to savor these moments as they happen and recognize their temporary nature. There is no reason to be sad about the passing of time because these moments are meant to be separate. Embracing this perspective helps one move through the world with more presence.

Success is often measured by financial gain or public recognition, but these metrics do not always reflect true achievement. A more meaningful way to define success is by looking at the quality of the work and the internal feeling it creates. Steve Jobs once defined success with a simple question: did I make something I'm proud of? This perspective shifts the focus from external validation, like listener numbers or revenue, to personal standards.

Did I make something I'm proud of? That is the way I think about it. It is not about how many listeners you have. It is about whether you made something you are proud of.

Jason adds another layer to this definition by asking if he would want to do the same thing again. If you finish a task, a project, or a day and feel that you would happily repeat the experience, then it was successful. This approach applies to many areas of life, including hiring and creative work. It centers success on the value of the experience and the trajectory of the effort rather than just the final outcome or the money earned.

Would I want to do this again? The next day, just this, whatever this was. If the answer is yes, then it was successful. It is not about money. It is about whether I would want to spend my time doing that again, playing replay.

Humans have a natural tendency to take simple ideas and make them complex. As people gain more experience and knowledge, it actually becomes harder to produce something simple. This is seen in creative fields where newcomers often create beautiful, simple work because they do not yet feel the need to add extra layers. Jimmy Iovine once told Rick Rubin that he wished he could still make things that simple, highlighting how easy it is to lose that focus on the heart of an issue as you become more established.

I wish I could still make something that simple. The point was that you don't know what you don't know. And so he made this beautiful, simple thing. And then you tend to think you need to add more things to it and make it more complex.

In the business world, Jason notes that the trend is almost always to add more. Owners often feel pressure to grow or expand because they worry people will get bored. If they take outside investment, the pressure to return that money can unmoor them from their original vision. They stop running their own business and start running someone else's business. This turns their passion into a job where they are essentially working for others on a track they cannot easily leave.

They've lost connection with why they started this in the first place. They're no longer running their own business. They're running someone else's business. They just create a job for themselves, working for someone else.

Jason views independence as the most important factor in business success. He equates independence with profitability. If a company generates more revenue than it spends, it retains the freedom to make its own choices. Jason and his partner David often choose to do things that traditional advisors would never allow. This freedom to act on unconventional ideas is what makes business exciting for them.

Independence is also that no one can tell us what to do. We feel obligated to do things nobody would allow us to do. That is a thing David and I talk about all the time. We should do this. No one would let us do this. Let's do it.

Jason contrasts this with the venture capital model. Many entrepreneurs think raising money opens doors. In reality, it often narrows their path. They must either become a massive success or face total failure. A business might be profitable and healthy but still not good enough for investors. This creates a situation where a founder might have to lay people off or watch the business fall apart because they lost their optionality. Jason values having the choice to stay small, sell, or keep going indefinitely.

The moment they go raise money, they have cut off almost every option. They think they have expanded their experience and their opportunities, but they have cut off almost every possible off-ramp outcome because now they have to be in big business or they fail.

This preference for simplicity extends to design. Jason admires the purity of original designs like the 1963 Rolex Daytona or the Porsche 911. He believes the first version of an idea is often the most honest. Subsequent models often add unnecessary layers just to drive new sales. For Jason, the most valuable ideas are those that remain focused on the core concept without added complexity.

The beauty of a product often lies in the purity of the initial concept. This represents the original idea and its first physical execution. Looking at early versions of a successful product shows how a great idea begins. For example, early Concept 2 rowers maintained a pure design that remains recognizable today.

The beauty is that this is the initial idea, this is the original concept, and this is the first execution of that idea in three dimensions in a product. They didn't just add stuff to add stuff. They added stuff that literally did improve things, not just to sell new models.

Changes over time should be functional. Improving materials to make a product last longer adds real value. This approach creates a stronger bond between the customer and the brand. It differs from industries like watchmaking, where updates often involve only new colors or minor stylistic shifts. Those changes are meant to sell more units without actually making the product better.

Modern construction often fills homes with digital screens and touchscreens that do not always improve the user experience. While some products like the Nest thermostat successfully update classic designs, many new devices use large, laggy screens just because the space is available. This leads to unnecessary complexity. For example, a new dishwasher might require a user to download and register an app before it can even be used for the first time. This does not make the task of doing dishes any easier.

A dishwasher couldn't be used the first time without an app to register it. Like, my mom wants to do the dishes. Like, they don't work. She had to call the house manager guy. He had to come down. He's like, why doesn't this work? I plugged it in and, oh, there's an app. I got to get a nap. Like, what you're adding and not making it better to do the dishes.

Jason refers to this trend as the great regression. Devices that used to be simple and instantaneous, like televisions, now require a boot up process that can take twelve seconds just to reach a menu. The shift away from tactile buttons and dials often removes the ability to use muscle memory. While companies like Tesla handle software well, many other car manufacturers are starting to return to physical buttons because people find big pieces of glass difficult to use while driving. Technology can actually get worse before it gets better again.

You don't turn a TV on anymore. You boot the TV up, and it takes like 12 seconds to get a menu before you can. Like, there were some things that were better before. You turn the TV on and the channel that you were on would be on. Like, that was good. Like you actually. It's amazing. Like you can't do that today.

Simple interfaces like the basic light switch represent a level of design perfection that is being forgotten. The switch is incredibly intuitive because it only has two states: on and off. This simplicity is increasingly being replaced by complex technology that requires instructions for even the most basic tasks. Jason notes that the best interface ever was the switch because it worked every time without confusion.

The best interface ever was like the switch, like on, off. It works on, off. Beautiful. It is almost like that has not been discovered yet because it had been, but then it had been forgotten.

Jason compares this trend to the lost art of Roman concrete. The Romans built structures that lasted thousands of years using techniques that modern engineers still struggle to fully understand or replicate. There is a similar lost art in simple hardware design. The tech industry frequently sells these regressions as if they are advancements. One day, people will likely rediscover the simple switch and realize it is far superior to complicated technical solutions.

There is a room and a place for all sorts of advancements, but there also are regressions. And it is unfortunate that the industry I am in is the one that tends to sell many of these to people.

The concept of a ruthless edit is a powerful tool for creators. If you produce thirty songs for an album, the best approach is to select only the five you absolutely cannot live without. This creates a perfect, condensed work. Often, adding more content does not make the final product better; it just adds volume. This principle applies to physical design as much as music. A timeless design, like a Porsche 911, is perfect because its silhouette is so distinct that it remains recognizable even if the car is burnt out. Other cars lose their identity when stripped down, but a truly great design remains itself.

He has this idea of ruthless edit. He is like, okay, you made 30 songs for your album. Pick the five that you absolutely cannot live without. So now we have a five song album. It is a perfect album.

Dosage is another critical factor in creative success. Jerry Seinfeld notes that a comedian might be fantastic for forty-five minutes, but the audience may grow tired if the set lasts over an hour. It is difficult to know when to stop adding complexity and just let a work stand as it is. Rick Rubin applied this to Johnny Cash by focusing on simple arrangements of a great vocalist with a guitar. This combination is timeless because it sounds as good today as it did fifty years ago. When Cash covered the song Hurt, the lyrics about regret carried more weight coming from an older man. The simplicity of the arrangement allowed the depth of that experience to shine through.

A 21 year old talking about regret is one thing. A 75 year old man, when he cannot go back and fix it, it is a way deeper cut.

Focus on the things in your business that will never change. Jeff Bezos once shared this advice with Jason, noting that customers will always want lower prices, faster delivery, and better selection. These core elements represent the essence of a business. It is easy to lose sight of these fundamentals because they can eventually feel boring. However, these basics are what truly matter to the long-term success of a company.

Make sure you focus on the things that don't change. Ten years from now, people are not going to wake up and go, I wish Amazon's customer service was worse. They're not going to wake up ten years from now and go, I wish it took longer to get a product from Amazon. These are the core essence elements.

Longevity is a powerful signal of quality. A business that survives for decades is rarely a fluke. It indicates that the organization is doing something repeatedly right. Jason has spent 27 years building his company by working a consistent 40 hours per week. While he does not consider himself a workaholic, that steady effort adds up to over 50,000 hours dedicated to a single project. Sustainability is the mark of a truly great business.

To be around for a long time signals that something is repeatedly right about this thing. Right enough to stay in business for a long time. It is a sustainable business, and that to me is a great business.

A great business can be compared to a tree that survives extreme environments. Jason views his company as an oak tree. Oak trees are stable and can withstand major storms. They are slow growing but last for a very long time. This is different from a cottonwood tree. Cottonwoods grow fast and make a mess. They are noticed by everyone but die within a few decades. It is better to build a quiet business with a solid foundation that adds a little bit of stability every year.

I do not need to be flashy. I do not need to leave signs all over the place that I have been here. It is going to be nice and quiet, build a great business, keep a solid foundation, and add a little bit every year so it just feels more stable and weather storms.

Staying around is the hardest part of being in business. The tech world is full of new products that claim to be killers of established companies. Most of these do not last. The best strategy is to simply outlive the competition. If a company stays in the game long enough, it will eventually find a way to get lucky. Often, an innovation from outside the company provides a huge advantage. For example, Coca-Cola benefited from refrigeration even though they did not invent it. Shopify similarly had to navigate the challenges of the pandemic to find its true path.

The hardest thing is just to stay around. People ask how we compete. We just stay around longer than everybody else.

There is no single correct way to build a company or be a leader. While some businesses grow like acorns into massive trees, the most important thing is to find a model that allows for longevity. Tobi from Shopify realized that many people just pretend to be the version of a CEO that others expect. In reality, there are hundreds of different ways to achieve the same goals.

Time serves as the most reliable filter for businesses, ideas, and people. While something might seem like a hot trend or a passing fad, only duration proves its true value. This approach applies to choosing books and identifying high-quality people. Building a seamless web of deserved trust requires years of consistency. Warren Buffett exemplified this by maintaining relationships for many decades, showing that the strength of a network is built over time.

Time is the best filter. It is the only filter I trust for businesses, for ideas, for books. It works for people too. The only way you know if somebody is high quality is time.

Success in business also depends on durability and survival. Mastering a few fundamental ideas across different disciplines like physics, biology, and economics provides a massive advantage. These core concepts carry most of the weight in understanding how systems work. Staying in the game long enough to let these ideas compound is essential for long-term survival.

Master the big ideas. If you just master the big ideas, those few handful of big ideas carry most of the freight.

Jason explains that Basecamp caps its pricing at 299 dollars a month, regardless of how many users a company has. While competitors might charge tens of thousands of dollars for thousands of seats, Jason intentionally avoids that money. The goal is to create a customer base of equal sized units. If a business can lose a hundred random customers and still be okay, it is a healthy business. The danger lies in having outlier companies that are too big to lose.

I don't want their money because what I want is a static group of customers. What you don't want are a bunch of outlier companies that you cannot afford to lose. You don't want customers that you cannot afford to lose.

By equalizing prices, the software is developed for the entire customer base instead of a handful of high paying enterprise clients. This approach favors durability over the enterprise game of landing whales. A business is more resilient when it consists of many small parts because it does not matter if someone chips away at a few of them. If every customer is essentially equal, the business does not fall apart like a game of Jenga when one piece is removed.

Intuition is the act of making decisions that feel comfortable and standing behind them. It is a collection of many different factors that are hard to separate. Jason relies on his gut for everything from pricing and product features to naming. He avoids using focus groups or letting spreadsheets dictate his choices. While data can be useful, he is careful not to value numbers more than his own feelings just because they look more official.

I am very careful not to put too much weight into something that purports to be more valuable than some other feeling I have just because it has numbers on it.

Refining intuition is not something you can practice directly. Instead, it is a result of making many decisions over a long period. Jason compares this process to tumbling objects until they become a smooth orb. The more decisions you make, the more your intuition sharpens and the less fear you feel. Eventually, you reach a point where you feel excited about a decision even if it might go wrong.

Intuition has to be used to really be enjoyed. And that requires independence.