The day I became a millionaire

Signal v. Noise
Published in
7 min readNov 25, 2015


I grew up lower-middle class on the outskirts of Copenhagen. Anywhere outside of Scandinavia, the socioeconomic label would probably have been ‘poor’, but Danish safety nets and support systems did their best to suspend the facts and offer better.

Me in the middle in home-made clothing to go with home-made ninja weapons… oh yeah!

But don’t worry: This isn’t a rags-to-riches story. I loathe the I-did-it-all-by-myself heroic myth mongering. I got where I am thanks to government-sponsored maternity leave, child care, health care, education, and even cash assistance. I grew up in housing provided by AAB, a union-founded affordable housing association. And my mother was a damn magician at making impossible ends meet without belaboring her tricks (like biking an extra 15 minutes to find the lowest price on milk).

I took two important lessons away from this upbringing. First, as long as your basic needs are met, the quality of your lived experience is only vaguely related to the trappings of material success. While it wasn’t all roses and butter cookies, I had a great childhood. Second, I wouldn’t learn to appreciate the truth of the first lesson until I saw the other side of the golden fence. More on that in a bit.

Commodore 64: One of the original crazy dreams

I remember playing the “What would you do if you won a million kroner?” game with my brother many times. We could spend eons making fantasy purchases. Comparing and contrasting choices and possibilities. Could you imagine not having to save up a whole year to buy a Commodore 64? Or to fly away on a foreign-country vacation every year? Or to — let’s go crazy here — buy a car for the family? (The sky setting those limits was barely higher than the Eiffel tower).

The underlying premise to these imaginary indulgences was how much better life would be if we were free from the constraints of our humble weekly allowance. Man, everything would just be so great if only I could…

As I grew older, this game was always at the back of my mind. There were always more things I wanted to do than money to buy them. It wasn’t that working towards certain material goals was really a chore or a struggle. My good fortune of being born in Denmark provided for the basics, and selling pirate software CDs through my Elite BBS contacts provided some modest splendor.

Electronic Confusion BBS ASCII from 1995

But there’s always an appetite for more, and a belief that just a little extra was going to be the tipping point for eternal bliss. Dreaming of an Amiga 1200, making it happen, and then thinking that, oh, what I really needed was that Amiga 4000. Somehow the repeated treadmill never seemed to bare its underlying truth, no matter how many times I took it for a run.

Then in 2006, it suddenly happened from one day to the next. Jeff Bezos had taken an interest in Basecamp, and Jason and I each sold him a minority, no-control stake of our share of the company for a few million dollars each (Basecamp had been self-funded and profitable from the start, so didn’t need any capital for the venture). I was a millionaire!

I remember the weeks leading up to that day when the numbers in my checking account suddenly swelled dramatically. They were anxious. I stood at the doorsteps of The Dream. A lifetime of expectations about how totally, utterly awesome it would be to be a millionaire. I’d be able to buy all the computers and cameras I ever wanted and any car I desired!

One of the other underlying pillars of this dream was the concept of Never Having To Work Again. Like somehow an eternity of leisure was going to provide the existential bliss I had been longing for all along. I thought about that a lot. I did all the math: Hey, if I stuff all the money in a prudent mix of stock and bonds, I should be able to live a comfortable, if not extravagant, lifestyle until the end of my days without lifting another finger.

The euphoria I felt when it was finally real lasted the rest of that day. The inner smile remained super wide for at least the rest of the week.

Then a mild crisis of faith ensued. Is this it? Why isn’t the world any different now? *shake, shake* Is this thing even working!?

Now don’t get me wrong, there is an enduring and very real satisfaction and comfort in never having to look at the price of a meal in a restaurant again (even though you still do). It’s just that like a good movie that’s been hyped to the hills, it’s almost impossible not to be let down when you finally see it. Expectations, not outcomes, govern the happiness of your perceived reality.

For the first few months, I barely touched any of the money. Sure, I bought a big screen TV and more DVD boxsets than I could hope to consume, but it wasn’t like I couldn’t have done that anyway. It wasn’t until near the end of that year I finally drew down on the account of cliched purchases: A yellow Lamborghini! While all very nice, very wonderful, it didn’t, as we say, really move the needle of deep satisfaction.

Common fallacy of wealth: “I’ve never seen an unhappy person driving a Lamborghini”

What kept moving the needle, though, was programming Ruby, building Basecamp, writing for Signal v Noise, taking pictures, and enjoying all the same avenues of learning and entertainment my already privileged lifestyle had afforded me for years in advance.

If anything, I began to appreciate even more intently that flow and tranquility were the true sources of happiness for me all along. It was like I had pulled back the curtain on that millionaire’s dream and found, to my surprise, that most of the things on the other side were things I already had. Equal parts shock and awe, but ultimately deeply reassuring.

Chiefly because I couldn’t lose those things. Barring any grand calamity, I could afford to fall off the puffy pink cloud of cash, and I’d land where I started. Back in that small 450 sq feet apartment in Copenhagen. My interests and curiosity intact. My passions as fit as ever. I traveled across a broad swath of the first world spectrum of wealth, and both ends were not only livable, but enjoyable. That was a revelation.

It’s funny, though, because I remember rich people trying to tell me this before I was rich. Not necessarily in person, but through clever or modest-profound quotes and interviews. And I remember always thinking “yeah, that’s easy for you to say now — you got yours”. It’s not lost on me that most people reading this will probably feel the same. It’s just the natural, instinctual reaction.

Primarily because I think it’s scary to think This Is It. This is what I got. Changing the numbers on my bank account or the size of TV or the make of the car in the garage or the zip code isn’t going to complete me. I have to figure that shit out on my own.

Again, I get that even having the pretext to contemplate such disillusion is an incredible privilege, beyond sympathy or even empathy of many in this world. I never went hungry to bed. I never feared getting shot. I never worried whether the end of my future prospects would be as a store clerk working minimum wage. The Danish experience shielded me from all those concerns of basic safety and comfort. So I won’t even pretend to know that struggle.

I can only speak to the experience I did have. The one I do share with millions of people who have the basics taken care of, but who still yearn for the treasure perceived to be behind the curtain. For those who might contemplate giving up all manners of integrity, dignity, or even humanity to pull it back.

We humans acclimate to our surroundings incredibly quickly. The buzz is not going to last. Until you realize the next rung of the ladder isn’t where salvation hides, the siren song will keep playing.

The best things in life are free. The second best things are very, very expensive — Coco Chanel

While the quote above rings true, I’d add that the difference between the best things and the second best things is far, far greater than the difference between the second best things and the twentieth best things. It’s not a linear scale.

Once you’ve taken care of the basics, there’s very little in this world for which your life is worth deferring. You’ve likely already found or at least seen the very best things (whether you know it or not). Make them count.



Signal v. Noise

Creator of Ruby on Rails, Founder & CTO at Basecamp (formerly 37signals), NYT Best-selling author of REWORK and REMOTE, and Le Mans class-winning racing driver.