Reflecting on five years at Basecamp

Back when I was a kid, they called this place 37signals. 👴👋👽

This week I celebrated my fifth year around the sun at Basecamp. For a lot of people that’s probably not a big deal, but for me it kind of is — it’s by far the longest I’ve ever been at any one job (my previous record was ~3 years).

That got me wondering — what’s so different this time around that made it stick? I eventually realized it basically came down to this:

I’m happy at Basecamp because every day I’m in a position to ship the best work that I can.

I admit that’s a rather generic statement, and pretty much every company in the world tries (or claims) to do the same. So what does Basecamp do that works so well for me?

Now before we get into the specifics, let me just say that this post isn’t meant to be a humble brag of how amazing Basecamp is. It’s simply an examination of how one company among many thousands operates, and why that meshes so well with someone like me.

So, as I was saying — what’s so special about Basecamp that it suits me so well? Well, it’s a bunch of things that all interleave together…

🚢 Shipping meaningful work is what matters

I’ve been at companies where I did a lot of “work”, but it often felt like I was just shuffling widgets around. I’d go to meetings, send emails, and make some stuff, but in the end, it’d be hard to tell if my work meant anything to the final product.

Other times we’d have so many pointless “stakeholder perspectives” that by the time we shipped, the final product was so watered down that it didn’t matter to anyone.

And yet other times, after months or years, some things would just never ship at all.

Basecamp is the exact opposite. As a small company working in small teams, we don’t have the luxury of spending any time on stuff that isn’t essential to shipping. And because we have to be choosy about what we work on, it’s usually the case that what we ship will be meaningful to our customers.

So we discuss ideas thoroughly, but don’t paralyze ourselves with analysis. We don’t pretend to know everything or try to predict the future, we ship and see what happens. We don’t have soul-sucking multi-hour meetings, we focus on the real work of designing, programming, and supporting our customers.

In the end, shipping meaningful work is what matters most to me, and that’s what keeps me motivated day in and day out.

😌 Calm is critically important

While shipping meaningful work is a great goal and motivator, even the best employees in the world can’t do their best work if they’re stressed, tired, rushed, or distracted. The folks at Basecamp know this, and that’s why calm and focus are cornerstones of everything we do.

One of the main ways we maintain calm is by not wasting time and energy on unnecessary bullshit and distractions. This is incredibly important to me — when I’ve got plenty of focused time to get my work done, I don’t rush. And when I don’t rush, I don’t feel stressed.

And while that may sound obvious and easy to avoid, I’ve worked at enough companies to know that wasting time is extraordinarily common. Opportunities to waste time present themselves in a lot of different ways, so here are just a few things we do to combat them:

  • We have very few (if any) meetings during a normal week. If there are any, they have the fewest people possible involved, usually a max of 2–3 folks. And we definitely don’t have recurring meetings.
  • We don’t commute. We all work remotely. Why spend 30–60 minutes traveling to some random building in a busy area to work when we can do the same work at home? This easily saves me 10 hours a week.
  • We don’t chat all day. There’s zero expectation of keeping on top of every chat or responding to an IM immediately. In fact, if anything we’re encouraged to close everything communications-related (including Basecamp!) so that we can focus on the actual work on hand. I regularly do this for hours on end, every day.
  • We don’t all work 9 to 5. We work hours that fit our life and brains. If, for example, you’re sharpest at 6 am, why the hell would you wait until “normal business hours” to start working? That’s a waste of your best brainpower! As long as we overlap a few hours with our team, we work when it makes sense, not by some arbitrary clock time.

Another major component of maintaining calm is to be very, very serious about not overworking and recognizing life’s priorities. In other words, when the work day is over, it’s over. And if something happens that’s clearly more important than work, we go take care of that . We work to serve our lives, not the other way around.

That means I don’t work some bullshit 60 hour work week.

That means that I don’t get notifications from the Basecamp app after 5 pm.

That means I don’t have meetings early in the morning or late in the evening that interrupts time with my family.

That means if I’m sick, I actually take the day off to get better, not partially stumble through the day trying to work.

That means if something comes up at home that’s way more important than work, I go take care of it and my co-worker’s don’t even blink at it.

That means I get a good night’s sleep because I’m enthusiastic about the next day’s work, not dreading it.

“Work-life balance” is an overused, rarely accurate term, but I think we’re doing it pretty damn well.

🙏 Autonomy and trust

A big part of Basecamp’s culture is the autonomy that we’re afforded. There are no managers, no daily stand-ups, and no playbook on how to do our daily work. It’s up to us to figure things out and own the calls we make.

For me that means I get to make a lot of decisions that have a direct impact on the outcome of my work — I choose what I want to work on, I make the final call on how any particular batch of code is shipped, and I’m ultimately responsible for how it performs.

Maybe this all doesn’t sound like a big deal, but it means a lot to me.

To me having freedom and autonomy is a vote of confidence. When the people around me give me plenty of space to do my thing, it isn’t negligence or disinterest — it’s trust. It means an awful lot to me that people I genuinely respect have such trust and confidence in me. Maybe that makes me weird or lacking self-confidence or sappy, but it’s true.

Whatever the reason, it’s been an important, formative element of my five years at Basecamp.

🎩 It starts at the top

Perhaps the biggest thing I’ve learned in my nearly 20 year career is that for me to have any kind of longevity at a company, it’s critically important to believe in the people at the top. I’ve worked for all sorts of companies before Basecamp, and I’ve never exactly felt super connected to those folks running the show.

Why is this important? Because at the end of the day, there are going to be a handful of people in a company that make the big decisions. And those big decisions in some way, big or small, have a direct impact on me and my work. These people are the ones deciding what’s important at the company, what isn’t, and what my work life is going to be like as long as I’m there.

And so the question becomes, do I believe in those folks? Am I more or less aligned with their principals — their professional beliefs, ethics, values, strategies, and overall ideals? Or do I have fundamental disagreements with a lot of what they believe in.

For me, Basecamp is the first place where I really do believe and trust in our leaders, Jason and David. Most everything they’ve done to build, grow, and sustain Basecamp agrees with me. And that makes it a hell of a lot easier to stick around and stay motivated than it would be working at a company where I’m constantly wondering “WTF are these clowns thinking?”

Now does that mean I agree with everything Jason and David do or say? No, of course not, I’m not some mindless drone. But generally speaking I do believe in the direction they provide and the choices they make. And perhaps more importantly, even if I do disagree, I respect their position, the thought they put into making a call, and the honesty and decency they treat everyone with.

👩‍👩‍👦‍👦 It takes a village

I’d be remiss if I didn’t mention the people I work with at Basecamp — what a crew! I truly, genuinely would not be where I am today in my career without them.

Sorry, it’s a tired trope but I have to say it — I work with really wonderful people. They’re so open-minded, friendly, welcoming, and damn smart. We’ve worked on so many great things together and I’ve learned so much from them. It’s an easy choice to stick around when you’re around folks like this. And beyond all that, they’re just great human beings.

Thank you Adam, Andrea, Ann, Ashley, Blake, Chase, Chris, Colin, Conor, David, Dylan, Elizabeth, Eron, Flora, George, Jabari, James, Jamie, Janice, Jason, JZ, Javan, Jay, Jayne, Jeff, Jeremy, Jim, Joan, John, Jonas, Justin, Kristin, Lexi, Matt, Matthew, Merissa, Michael, Nathan, Noah, Pratik, Rosa, Ryan, Sam, Scott, Shanae, Shaun, Sylvia, Tara, Taylor, Tom, Tony, Wailin, Zach, and all our beloved alums for making this a fantastic five years!


Thanks for reading — if you enjoyed it, please do mash the 👏 button so we can show Medium that they really nailed that 50 clap idea! 😏

What’s my purpose?

One of the most common questions I’m asked is: “How do I find my purpose?” The askers seem bored with their current jobs. They feel lost. They want to work on something that has more importance to the world.



On November 18, 2007, Dennis Quaid’s infant twins were given two injections of Heparin — 1,000 times the normal dose. Heparin is a useful, but dangerous, blood thinning agent. The accident was fortunately caught in time, and an antidote was given to the twins saving their lives. But in 2008 a similar accidental use of Heparin occurred where 17 babies were given the wrong dosage. Two of them died.

Medical mistakes like these are still too common. Dennis Quaid made it his mission to raise awareness of the issue. He helped produce a documentary called Chasing Zero. The short film traces the stories of people who’ve been traumatized by human medical error with hopes of inspiring more medical practitioners to work to eliminate human mistakes.

Interestingly, the documentary team found the janitorial staff deeply involved in making changes at Mayo Clinic, a hospital known for going to great measures to reduce human error.

Mayo Clinic had discovered that the remote controls in patients rooms had higher bacterial counts than toilet seats. So the janitorial team, without even being asked, came up with new procedures and checklists to keep rooms cleaner.


When Iris Cowger, a janitor at Mayo Clinic, described her role,

We’re not just cleaning rooms. We’re saving lives.

She cleans walls, floors, toilets, and remote controls. But she has a radically different perspective of what she does. One that motivates her and her team to take innovative measures that further improve the lives of everyone she comes into contact with.

Iris found her purpose.


When we interviewed Highrise customers earlier this year about why they use Highrise, a simple CRM, we found an interesting niche of user.

These were folks doing sales who didn’t consider themselves salespeople. They were writers, designers, software developers, insurance agents, cosmeticians, etc. who just so happen to have to do sales to keep their businesses alive.

One customer described what he does as, “I’m salesperson in my head, but a designer at heart.” The thing that got him excited was designing the products his business sold. But he had to be out there making deals or the business would tank.

All of a sudden I had a new perspective on what we do here. We aren’t just hosting software to manage contacts, emails and follow-up reminders. We’re helping people keep their businesses alive and get back to what they actually love to do.

I know a lot of people are out there seeking new jobs and careers and businesses because they think they still haven’t found their purpose. So they keep looking. And looking. Sometimes making big changes to their careers and lives only to end up feeling like they still haven’t found what they’re looking for.

There’s nothing wrong with career change to get closer to things you have more passion for. But I think far too many people look at what they do myopically. When they open their eyes and see the people they affect with their work, it becomes much more clear how important the thing you do already is.

There are plenty of janitors at hospitals that see their jobs as simply cleaning rooms and floors. They check in. Check out. It’s a paycheck.

Iris saw the higher purpose of her job. She didn’t need a career change. She just needed the right perspective. And that perspective keeps her motivated to show up at work every day and save lives.

The key to finding your purpose is to be more like Iris.

P.S. You should follow me on YouTube: youtube.com/nathankontny where I share more about how we run our business, do product design, market ourselves, and just get through life.

And if you need a zero-learning-curve system to track leads and manage follow-ups you should try Highrise.


I don’t have enough


It’s been a rough week. We’ve been migrating our file storage for Highrise and you can imagine how difficult that is for a product running since 2007 with millions of users.

And it wasn’t going that well.

Fortunately, we had enough backup procedures in place to handle most problems. But still, on Thursday morning at 3AM I was nervously watching the error queue for more fires.

How’d I get here?

I don’t mean that in a negative sense. This barely raised my blood pressure. I’ve been in this same situation many times before. I and our CTO, Michael Dwan, cooly fixed our problems in the middle of the night.

But, I mean, how on earth did I get to this point where I’m helping successfully troubleshoot this crazy large system of technology and code when…

All I was trained to do was Chemistry?

I remember the panic I had nearing the end of college. I had just spent 4 years and tons of money learning Chemistry, and I finally realized all I wanted to do was build software and web applications. What a waste.

How was I going to change my entire career around?


I asked a friend the other day, if they were given two, one foot diameter, metal rings, a match, a candle, and a metal cube, could they connect the rings?

At first they didn’t see the solution.

But once I told them to: break down the resources they had into smaller pieces and re-think the uses of those elements, the answer was clear.

The candle wasn’t just a candle.

If you break it down one level, it’s wax AND a wick. Use the wick inside the candle as a string, and use that string to tie the metal rings together.

This was a challenge Dr. Tony McCaffrey, a PhD in cognitive psychology, gave participants in various studies he’s done. He found, when he taught people to break down the resources they had at their disposal into smaller elements, and then re-question the use of those new smaller pieces, participants’ ability to solve problems grew by over 65%.

The real problem McCaffrey was helping these people solve wasn’t tying two rings together; it was getting over their “functional fixedness”.

We want something more out of life for ourselves or the world, and we all see the same resources. But most of us feel like we’re stuck with them. We need more. Better. What we have isn’t good enough.

The greatest creators amongst us though, see the same world and have the same resources, but somehow, they’re able to turn those resources into brand new things that solve problems and move the world further ahead.


My boss needed help with Excel.

I was at an internship between my Junior and Senior years at a Uranium processing plant. (yes, that Uranium) My boss was building financial models in Excel and wanted help updating them.

At first the project seemed fairly uninteresting. How was this going to help get me out of the chemical plant into building software for a living?

But I realized something. My boss’s life would be much easier if I could get Excel presenting him with forms and walking him through the things he needed to update. Excel had “macros” which were bits of VBA (Visual Basic for Applications) code that I could program.

This wasn’t uninteresting. This was an opportunity. I could use this to deepen my exposure to writing code. It wasn’t building a fancy web app, but I needed to start somewhere, anywhere, and this was it. So I squeezed every last bit of time I had with VBA to help my boss and get better at software development.

When I was out of college, I took a job with Andersen Consulting (now Accenture). My thought process was — this company does software projects. Maybe, it’ll give me a door to a new field.

However, Accenture put me in their “process” vertical. My day to day job was managing discussions with customers and recording the requirements they had for developers. I wasn’t doing software development. I was writing documents.

A project came up though that wasn’t worth a developer’s time. Our customer wanted to use a reporting tool to connect to their data warehouse and they needed reports built.

It looked like another uninteresting project of listening to what fields a user wanted in the report, and using the reporting tool’s drag and drop interface to stick the field in a report.

But, then I realized something. There was more to this reporting tool.

The reporting tool could be programmed with Javascript to create forms and build reports dynamically. This was the Excel situation all over again.

I listened carefully to what our customers wanted and figured out more dynamic and flexible ways to get them their reports using forms and programs I built with Javascript right inside the tool.

My boss was happy they over delivered on the reports our customers needed, and I learned a ton more about Javascript and doing more development.

So much more that another opportunity presented itself at Accenture — they promoted me to a software development team since I showed such aptitude and hustle.

All of a sudden I was exactly in the position I wanted to be in.


Today, I consider myself to be an above average developer. From publishing some decent open source projects to starting software companies from scratch.

When I think back on the career I’ve had so far, I realize how much of it was looking around at the resources and tools I’ve been given, but instead of complaining and getting stuck hoping for better, I not only made due, I invented new purposes for them.

Instead of taking Excel and this reporting tool project at face value, I saw they had components that could be repurposed to help the people I worked for and give me the education I needed in software development.

People, too often, look outward at all the things they wish they had to improve their life. When really, if you break down the things you already have, you might just see they’re the exact solutions you needed.

P.S. Please help spread this by clicking the below.

You should follow my YouTube channel, where I share more about how we run our business, do product design, market ourselves, and just get through life. And if you need a no-hassle system to track leads and manage follow-ups you should try Highrise.


Work Can Wait 4,380 days

Or maybe it can’t. It’s your choice — That’s the point.

I love seeing the look on people’s faces when they learn I took 12 years off to raise my kids. They say, ‘But you’ve got such a great career in high tech! How’d you do that?’


I’m living proof you can take a break from your career to do something important to you and still have the career you want when you’re ready. For me, that break was to raise my boys — for you, it could be to travel, care for a family member, pursue an interest, give back or just chill.

Own your work-life decisions

I was the first person in my family to go to college. My Cuban-born mother had an eighth-grade education — my father graduated from high school. I earned a scholarship to Columbia University’s School of Engineering, where there were only three women in my electrical engineering class. After graduation, I got married and started my career in the high-tech industry. I loved my work.

A couple of years later, I had my first son. I fully intended to go back to work after my maternity leave, but the moment I held my son, I knew I wouldn’t be returning to work — not yet. There was something else I wanted to do more: raise my children.

This wasn’t an easy decision. I carried the yearnings of generations of women in my family who hadn’t had my opportunities. They couldn’t understand how I could ‘walk away from my career,’ and they couldn’t see a path for me to walk back later. I also loved my work, I was making a lot of money and I had financial independence. Yet, there was a voice inside telling me to embrace parenting. I listened. I knew on some level that taking time out of my career to do something I REALLY wanted to do wouldn’t be the end of my career.

But this post isn’t about whether to stay at home or to have a career; it’s about trusting your intuition, following your heart and having faith in yourself.

How to take time out of your career without ending it

There is no blueprint for making work wait for 12 years. And yet, I’m always asked how I did this. I never had a plan. I made my choices along the way.

Even though work was waiting, learning new things never did. During those 4,380 days, I thought of my children as my most meaningful work—the immovable priorities in every day—and I chose other pursuits that could fit around them. I earned a teaching credential, taught computer classes and taught myself emerging technologies. (My work passion was also my hobby, which I shared with my children, teaching them to program in Basic.) I consulted to small businesses and helped them set up their networks, volunteered at my sons’ schools and always worked part time around their schedules. In my 12th year out of the workforce, I got a full-time offer to build out a college technology center, join the faculty and then become dean of instructional computer technologies. Later, my self-taught Unix sys admin skills landed me at a company that taught Unix classes in Silicon Valley. It was perfect for me.

From that point forward, as I had before, I used my troika loves of emerging technology, applying technology to business problems and serving customers to choose my next move. I went to business school — my boys would post my report cards alongside theirs on our refrigerator. After I earned my MBA, I worked at email marketing company MarketFirst, then went on to content management software company Interwoven. When I realized I had a passion for the consumer online, I went to Yahoo, where I lead a global team of over 400 professionals in more than 20 countries. I followed my interest of ecommerce and women as CHOs (chief household officers) into a role first as CTO and then as CEO at Myshape (personalized online shopping experience) and then became the GM of ecommerce at Sears Holdings. Which brings me to my role today as chief operating officer for Basecamp.

Along the way, I concentrated on the choice that was in front of me. I never tried to calculate how to land at some future state of my career.

4 Tips for making choices and taking chances

Your career is one part of your life — it’s not your whole life. This is what I learned when I reset my life-work balance for 4,380 days:

  • It’s personal. There is no blueprint. You have to find your own authentic path and make it work for you.
  • Own it. If you don’t believe in your choices, no one else will either.
  • Focus on your strengths and passion. I am passionate (maybe it’s the latin blood). I never wavered from my mission of using emerging technology to help businesses and people be better — even when I hit the pause button on full-time work. Do what matters to you.
  • Don’t let others define you. When others attempt to put you in a box, they’re merely projecting their own fears on you. Resist the temptation to limit yourself because of someone else’s fixed mindset or because you’re afraid.

I’m a better leader because I did what I was drawn to do. It took courage then, and all these many years later, I find myself working with co-founders who have the courage to say this very thing to all of our employees. So, it turns out work can wait. Now that both of my sons are pursuing their own careers, families and passions, I feel energized to continue pursuing mine, knowing that one of my passions has multiplied my efforts.

Sometimes, work can wait — whether that means thousands of days or just evenings and weekends. If you agree, check out our Work Can Wait pledge, and hit the 💙 button below.

It’s OK to be pragmatic (with a little help from the “crazy ones”)


Being pragmatic is engrained in me. I’m at my best being practical and boring.

Here’s the problem — experience has taught me that you’ll never do your best work through sheer pragmatism alone.

While I’m good at weighing options and making decisions, I’m not that visionary who can conceptualize grand ideas.

While planning comes very naturally to me, I find it difficult to inspire others.

And though I’m good at shipping, I often do so using following established conventions.

So while the incremental, risk-averse nature of being pragmatic can be good for many aspects day to day of work, it’s not everything.

What you’re good at and what’s good for you aren’t always the same thing.

To make long-term, deep progress in your professional growth, you need to think big sometimes.

You need to try things that don’t have predictable outcomes. You need ideas and ways of thinking that inspire innovation. You need to stretch way beyond your comfort zone.

But as a pragmatist, how can you do all this when it’s so foreign to you?


Surround yourself with the “crazy ones”

The idea of the “crazy ones” may be Apple’s, but that kind of creativity, inspiration and genius is all around you.

Look for opportunities to work with people who are the opposite of you — the dreamers, big thinkers, and contrarians.

These will be the people who will push you toward bigger and better things.

Yes, it’s going to be very hard and uncomfortable for you. You’re going to feel like you’re on a bizarro planet where everything is backwards and nobody thinks like you.

This is a good thing.

Having people challenge your baby-steps thinking with big-leaps thinking is a good thing.

Not understanding what the hell one of your colleagues is thinking (at first) is a good thing.

Having healthy discourse around big ideas is a good thing.

And shaking hands and finding compromise is a great thing.

Their thinking will seem crazy and executing their ideas will seem impossible. But in end you’ll pull it off — not in spite of you, but because of you.

You’ll be better in every way because you stretched well outside your comfort zone. And really, what’s more rewarding for a pragmatist than shipping something you didn’t think was possible? 🤘


If you liked this article, I’d sure appreciate if you clicked the 💚 button below. Thanks!

I was lucky enough to work with some of the crazy ones on Basecamp 3— especially Jamie Dihiansan, the designer of the Basecamp 3 Android app. Check out what happens when you get a happy mix of pragmatism and crazy!

Remembering how I got here — with a lot of help from others


About a month back, Basecamp put out a call for internship candidates. We’re looking for great people who want to learn about programming, product design, operations, data, or marketing directly from the people who work on Basecamp every day.

But before we went public with it, any interested team had to internally pitch a meaningful project and commit to investing the proper time and energy into teaching, guiding, and helping our interns regularly.

The Android team is made up of three people. And of those three, I was the loudest “no” vote. I think it was something along the lines of, “we don’t have time, it’s not a priority.”

I look back on that now and realize how insanely silly and selfish that was.

At every turn of my 15 year career, people have been helping me. Helping me to learn new skills, advance my career, or just to be a better person. I’ve tried to do the same for others over the years.

And yet when I was given such a clearcut opportunity to help someone else professionally, my first reaction was to punt it away because it wasn’t “a priority.”

At that moment, I had completely forgotten how I got to where I am today— with a lot of help from others. Sure, hard work, persistence, and maybe even some smarts helped pave the way. But I sure as hell didn’t build my career all by myself. I needed to remind myself of that. I needed to remember how I got here.


I have no idea what I’m doing

At my first job out of college, I was thrown onto Java projects. I had no idea what I was doing. For over two years, a bunch of people helped me as I fumbled my way through the basics of programming, business, and being a professional. These years laid the foundation of my career. Without the help, guidance, and friendship of a few key mentors, my career wouldn’t have turned out nearly as well as it did. I’m sure of that.

Truth.

By 2008 I’d been doing Java for a long while, and it was time for a change. I joined an interactive design agency in Chicago, converted to a project manager, and once again had no idea what I was doing. I was running multiple projects with dozens of people, in an industry I didn’t fully understand. I wasn’t doing any programming, but I sure was making a lot of clients angry.

And once again, so many people helped me through it. Veteran project managers taught me the tactics of project delivery, designers helped me understand the intricacies of their work, and account managers helped me handle, persuade, and sell to clients. By the time I’d left, I was a better balanced, more polished professional in all areas of my work, in large part because of the help of others.

Fast forward to today. I’ve been at Basecamp for almost three years, and have been a professional programmer, consultant, and project manager for over 15 years. And yet part of me still has no idea what I’m doing. I’m still getting help from others on a daily basis, from every part of the company. It doesn’t matter what I’m stuck on, there’s always a friendly teammate to help me with all the things that I don’t understand (which is a lot).


Paying it forward

Hopefully by now it’s crystal clear why I felt like such a fool for saying no to the internship idea. I honestly can’t imagine where I’d be today professionally if it wasn’t for for the selfless, generous help of others. But there’s a happy ending to this story.

About a day after I said no to the internship idea, I realized my madness and jumped on board with the idea. And not only did I vote yes, I wrote the formal pitch for our project and will be the point person for our awesome Android intern.

I know I didn’t say thank you enough to everyone who helped me so much along the way. I can only hope that paying it forward now and in the future serves as a small repayment of that debt.

So the next time you’re given the opportunity to help someone professionally, I’d encourage you to really stop and consider it. I know time is short and life is busy. But try to remember those people who helped pave the way for your successes — think of how proud they’ll be to know they’ve taught you well.


If you’re interested in one of our internship projects, applications close on 2/24/16, so you’ve got less than a week to apply. Get a move on!

We’re hard at work making the Basecamp 3 and its companion Android app the best it can be. Check ’em out!