Silicon Valley should welcome the scrutiny

The glowing haze won’t cover things up forever

It’s been a tough year for the tech startup capital of the world. One marred by scandals, flame-outs, and pissy, defensive postures by its royal court. I get the sense that a common thought is “what happened?!”. Why all the scrutiny, why now?

Because you’re not a punk upstart anymore, slick. Not that you were last year either, or the years before that. It takes a while for people to catch up when the world changes, but eventually they do, and now they have.

Just look at the lingo. It used to be that you could unironically claim to be disrupting this or that, and people would look at you with puppy eyes asking to hear more. Now if you claim to be on some disruptive mission, you’re far more likely to be met with skepticism and critical inquiry, if not outright eye rolls.

That’s because the disruption story hasn’t had the neat happy ending its main protagonists would like you to believe. Whether it’s the gig economy normalizing, nay, celebrating, working three jobs to make ends met. Or specifically ride sharing outsourcing all capital costs and risk to drivers. Or apartment buildings turned into defacto hotels by short-term rentals. There are real, systemic downsides.

Remember “move fast and break things”? So hoodie, so cool. Until we realized that what was being broken was us. People. Broken as mechanical turks in the gig economy. Hidden beneath a savvy app that rendered the human connection as cold as code.

And if it wasn’t your literal back being broken, then it was your mind. Your attention hacked. Your base instincts exploited. Your dopamine trail trashed by self-confessed dark patterns. All so you could juice an engagement meter. Be that DAU. Deliver those clicks. Supply all those likes. Posit those comments.

We got grounded up as “traction” to pave a road for a few high-riding winners that took it all.

The consequences of these trends weren’t clear to most for a long time. It was just new, and exciting, and oh-my-god-look-at-that-kitty!!! The distraction worked until it didn’t. More and more people are waking up to a world driven by Silicon Valley software companies and thinking: is this really better?

Sure, it’s better in some ways. And those ways have gotten the lion’s share of the press and focus over the past decade. But in all the many, many ways it is not, well, we’re just starting to look at that critically as a society. It’s beyond overdue.

Those critical eyes haven’t had to look very far to find the rot and the malfeasance. Uber is both the most valuable tech startup to come out of San Francisco in this latest rush, and one of the most despicable companies ever to reach such a large scale.

But the ethical rot is of course not restricted to the unicorn of unicorns. It is merely the prize stallion breed from a culture seeped in it. Starting to clean that up requires acknowledging not only that there’s a problem, but the role these dominant software companies now play in the world.

The royal court in and around Silicon Valley is clearly struggling with that part. Here’s the head of the influential startup accelerator Y Combinator justifying bigotry on account of “innovation”:

This is uncomfortable, but it’s possible we have to allow people to say disparaging things about gay people if we want them to be able to say novel things about physics. [1] Of course we can and should say that ideas are mistaken, but we can’t just call the person a heretic. We need to debate the actual idea.

If we want “innovation” from Silicon Valley, and elsewhere, we need to debate people who think gays can be “cured”? Or whether phrenology actually has scientific merit? What the actual fuck.

No. Cuddling bigots out of fear they won’t keep shitting unicorn turds is not what this industry needs. Instead, it needs to accept just how dominant and controlling the major software companies out of Silicon Valley from the last ~decade have become. They now are the man.

With this awesome and fearsome power over the lives of billions of people around the world should come an equal measure of responsibility. Along with decency, empathy, and some gawd damn ethics.

It’s ironic that while some corners of the tech world loves to shit on the humanities, it’s these areas of study that they most dearly need right now. Less focus on how we find the people to build the next engagement trap, a little more on finding people who’ll ask whether we should.

But this lack of self-awareness and self-critique is hardly surprising when you hear them whine about the “distracting and demoralizing dishonest reporters”. As Kara Swisher replied: Cry me a river!

It’s in large part thanks to reporters and journalists that we’re just starting to understand and map the rot of Silicon Valley. From the despicable business practices to the harassers and abusers who’ve been preying in their ranks.

It’s time for Silicon Valley to stop running from the skepticism.

Sure, it could embrace the old Wall Street ethos of proudly flouting a complete disregard for accountability and decency. But the difference is that the new cast of characters don’t just want power and wealth, they want to be loved too.

Here’s a newsflash: The way to our heart doesn’t go through excuses, but through redemption. Fewer former executives looking in the rear-view mirror shuddering at the car crash they caused, more current executives making the conscionable choices to avoid them.

That’s unlikely to happen through some sudden corporate epiphany, but because brave individuals and outlets keep turning up the heat and the scrutiny.

If you’re reading this, you probably don’t do hard work

Actual hard work

Designers, programmers, tech entrepreneurs, and investors love talking about how hard their work is.

Let’s get real.

Hard work is picking lettuce 8 hours a day in 90 degree heat.

Hard work is being a single mother or father who has to work two minimum wage jobs back to back with nary a recuperative break all day.

Hard work is heaving dirt and rock on a construction site. Or working with industrial equipment that could crush you if you make the wrong move.

Rule of thumb: If it’s hard you’ll have trouble finding people who want to do it. There’s no shortage of people who want to be programmers, designers, strategists, social media consultants, entrepreneurs, investors, etc… But try finding people to work the farm. Hard work is doing the work other people don’t want to do.

Coding, or designing, or writing pitch decks, or making sales calls, or preparing spreadsheets, or writing blog posts, or social media marketing, or buying ads, or choosing the right color, or picking the right paper, or making a layout responsive, or investing in companies, or doing due diligence, or making decisions, or coming up with a strategy, or allocating capital, or figuring out how to spend the budget, or reading up on a subject is not hard work. That’s just work. If you can do it in an air conditioned room, with no physical threat to you or someone else, while seated, it ain’t hard work.

It may be challenging work. It may be creative work. It may be skilled work. It may require multiple tries to get it right. You may have to learn new things. You may be rejected a bunch. You may get hung up on. You may not know how to get from A to B. You may have to persuade. You may have to deal with people you don’t like. You may have to sell something someone doesn’t know they want. You may have to be creative. You may have to build something that hasn’t been built before. You may have to battle entrenched interests. You may have to put in a few days or weeks in a row to figure something out you’re stuck on. You may have to make tradeoffs. But that’s the work. Not achieving the outcome you wanted doesn’t make it hard, it means you have more work to do.

If you enjoy it most of the time, it’s probably not hard.

Solving a problem doesn’t mean you worked hard. It means you decided to put in the work to solve the problem. Maybe you thought about it differently. Maybe you came at it from an angle no one else did. Maybe you just decided to take something on other people couldn’t see. None of those things make it hard.

And maybe you’re really good at something, while other people are very very bad at it. But that doesn’t make it hard either.

Long hours don’t equal hard work. They just equal long hours. The time you put in has nothing to do with how hard something is.

Brainstorming isn’t hard work. Riffing isn’t hard work. Networking isn’t hard work. Going to conferences isn’t hard work. Dodging traffic isn’t hard work — it’s commuting. It may be shitty, but it isn’t hard.

And please, giving your opinion isn’t hard work. Bouncing from meeting to meeting giving advice isn’t hard work.

I get why people love calling their work hard. It feels good. It feels important. It makes you feel like you’re doing something that some other people would choose not to do. I absolutely get that.

But none of that makes it hard.

We all have work to do. Do good work. Do creative work. Do thoughtful work. Do your best. But there’s no need to flatter yourself about how hard it was.

Chicago, Be Chicago

Yuck! Enough with the Silicon Valley worship, Chicago!

🎶Hey, Chicago, what do you say? Can we stop talking about wanting to be the next Silicon Valley today?🎶

If you pay attention to the Chicago tech/media scene, you’ve probably been hearing for years that Chicago is poised to be the next Silicon Valley. The storyline continues in this recent Inc article: Why Chicago will be the next Silicon Valley tech hub.

There’s a lot of good in this article. And we’re honored that Basecamp is held up as an example of something positive happening in Chicago. But the notion that it’s now Chicago’s time to grab someone else’s torch is where it falls apart for me.

It’s certainly true there’s more entrepreneurial excitement in Chicago these days. More optimism, more opportunity, etc. This is great.

But what’s with all this this fetishizing of Silicon Valley? To be next in line to be them? What about being us? What about being original? The Silicon Valley approach is original for Silicon Valley, but what’s our original approach? Something that’s expansive, rather than restrictive. Following someone else’s playbook is always limiting.

Why not build something here that’s so fresh that eventually other cities want to model themselves after us? What would that look like? 10 years now we’d be far better off if other cities were saying “We want to be the next Chicago” than “Chicago is still trying to be like them”. Unfortunately today if you Google “The next Chicago” the first story is about how citizens in Richmond Virginia are afraid their town is becoming like Chicago.

Some suggest Silicon Valley stands for innovation. Ok — I’m into that. But if we’re just trying to be like them, where’s the innovation in that? That’s the opposite of innovation. So to be innovative, we want to copy? That gets you to me-too, not us-instead.

Further, why follow a playbook that leads to oppressive rents and a workaholism culture? A race towards pumped-up billion-dollar valuations rather than a thousand paying customers? Why salivate over so many profitless-revenue and unsustainable business models? Why build companies to be sold rather than ones built to prosper independently?

What’s so unattractive about stability and make-more-than-you-spend economics? The economics the pizza shop, dry cleaner, autobody shop, and restaurant down the street live by? If they can survive like that — some for 25 years or more — why can’t a tech company with far more favorable cost structures?

I get it. Rapid job creation. Pumping millions/billions into startups that are hiring is a quick way to show things are happening. But if we can’t build sustainable businesses built on solid fundamental economic principles, those will all be temp jobs. Long temp jobs, but temp jobs nonetheless. That’s a political move, not a purposeful move.

Of course Silicon Valley has some wonderful success stories reaching back decades. No doubt — amazing things have been created there, and I admire and respect many of those stories. I’m a happy customer of a few of them for sure. But a successful Chicago doesn’t need to be predicated on the next Apple or Tesla being here. That’s limiting.

Further, it’s too easy to assume that there’s a formula that any city can apply to generate those kinds of businesses. Specific inputs that always produce specific outputs. If we do what they’ve done, then we’ll get what they have. It doesn’t appear to work that way. Is it just a matter of eventually, or is it a matter of place and moment? That places are unique, and intangibles make the difference? That moments can’t be manufactured? That luck is the largest variable in the equation?

Great places are unique places. New York is uniquely New York. San Francisco is uniquely San Francisco. LA is uniquely LA. New Orleans is uniquely New Orleans. New York isn’t like LA, and LA isn’t like San Francisco, and Seattle isn’t like Boston, etc. Silicon Valley didn’t become “the next whatever”, it developed into itself. New York isn’t striving to be Rome, it’s thrilled with being New York. But Chicago?

If Chicago is going to follow anyone’s philosophical lead, let it be Simone Biles: “I’m not the next Usain Bolt or Michael Phelps. I’m the first Simone Biles.” That’s confidence. We could use more of that here.



I remember the last time Chicago got frothy about the closest thing we’d had to a Silicon Valley success story: Groupon. The city rallied around it. Everyone hailed as the fastest growing company ever, and it raced to a $1 billion dollar valuation on waves of institutional investment. We celebrated around fastest growing, not profitable, not sustainable. And now just a few years later, you don’t hear many people talking about Groupon anymore — except when they need to show an example like the one below:


(Full disclosure: I was on the Groupon board prior to them going public, but was asked to leave after a year.)

And today, in 2017, guess who’s being touted as the fastest company to a $2 billion dollar valuation? Uptake, another Chicago company. I hope things turn out differently for Uptake than they did for Groupon.

I hope Chicago avoids the trap. That we don’t get carried away by bullshit metrics, and wannabe stories. Rather, we build more sustainable, profitable companies. Companies that grow steadily and strong, not rapidly and weak. Companies that treat people exceptionally well, and create environments where people can do their best work of their lives — and have great lives at the same time.

Chicago, be Chicago.

How I left behind my silicon dream for a saner place to work


It all started in September 2015. I had recently graduated from DePaul University in Chicago, where I had studied Information Technology, and I was flying out to San Francisco to join the ranks of Silicon Valley — the promised land for any twenty something tech hopeful. “All the biggest and best companies are out there. That’s where I want to be,” I told myself.

I always knew I’d be working in tech. I had my first computer when I was about four years old, and I vividly remember the look of MS-DOS as I watched my father install a Star Wars X-Wing simulator on it. I’d always been fascinated by computers, and finding out how they worked. It only made sense that I’d make that my life profession and move out to Silicon Valley.

I planned on being in the Bay Area for two weeks. After my first week, I knew it wasn’t for me. I went to countless Ruby, Rails, and other tech oriented networking events, talked to some founders, and set up some interviews. None of it felt right. I felt like a number, a cog in the tech machine. It was all about making it big and getting that next round of VC funding. That’s not what I envisioned it to be like. On top of that, I felt hostility when telling people at the coffee shops that I was there to get a job in tech. It was as if people wanted nothing to do with me once they found out I was trying to implant myself there and contribute to the decline in culture and rise in tech that has proliferated throughout the Bay Area. I wanted out.

I stayed for part of the trip with a friend who worked at Google. I used to dream of working at a company like Google when I was in school… but seeing the reality of it made me question that dream. At Google, my friend said he’d routinely put in 80-hour work weeks. That’s insane! It was like a badge of honor to people out there. Granted, part of that was his two hour bus ride to and from Mountain View, but still, there was no way I was going to be doing that, even if that’s what it took to be a Googler.

I no longer wanted to be a cog in the Silicon Valley machine. I wanted to be a human, working for a company that valued me, and enabled me to do meaningful work that would help me make my small dent in the universe. I went home to Chicago and refocused. I started to think about what type of company I wanted to work at. I wanted to work somewhere that would care about me as a person, enable me to positively impact other people’s lives, and preferably do some sort of work with Ruby on Rails.


One morning in January, while doing my usual job-hunting, I saw DHH tweeting about an internship program for the Summer of 2016. This was my shot. I’d dreamed of working at Basecamp, and maybe the internship program would give me that edge I needed to get started with my career in Ruby on Rails. It wasn’t the full time job I was looking for at the time, but after reading the internship description, I was in love. I knew this was for me. It was everything Silicon Valley wasn’t. Basecamp was hosting an internship program that treated their employees like humans, and like real professionals. This was a far cry from the traditional “go get me coffee” or “file my papers” internships you hear about. We’d be solving real problems the business faced, given a foundation to learn and grow, and be treated like the managers-of-one they were looking to bring on board.

I finally heard back about a month after I had applied, and to my excitement, they wanted to interview me! I prepared for the interview by going over my Ruby on Rails knowledge, practiced the FizzBuzz test, and went over past interview questions I’d gotten with other companies while out in California. None of that was needed. That’s not the Basecamp way… I should have known. I’d read REWORK and REMOTE after all — we don’t hire programmers based on parlor tricks, so why I thought their internship interviews would be any different is beyond me. Perhaps I was still stuck under the delusions of Silicon Valley — I forgot this doesn’t have to be the norm.

Instead of whiteboard problems and FizzBuzz tests, I had a very human talk with two different Basecampers. We talked about why I wanted to be an intern at Basecamp, what projects I’d done in the past, and even got nerdy and did a deep dive into how I did geolocation for a weather website I’d made. I left the interviews thinking, “That felt like talking to a friend, not like an interrogation.” That’s how an interview should feel.

During my internship, I was given complete freedom to work on my own while helping build out internal tools that helped make fellow Basecampers jobs a bit easier. I remember my first day, I asked, “Where do I start?” and my mentor looked at me and said, “Wherever you want.” It was on me to find a problem, set my own direction, and build out a solution. The type of work I was doing wasn’t meaningless grunt work like most internships I hear about, but instead I was doing work that impacted people every day. Feedback like, “This is such a wonderful feature that will get a ton of usage. Your work will have a meaningful and positive impact on our day to day work lives for a long time,” was the norm here.

As my internship came to an end, I looked back on the work I had done and realized I was beginning to make my small dent in the universe. I’d had the opportunity to work on all of our internal tools, and even got to make a few entirely new ones myself. The things I made are being used every day, and they solved real problems we faced as a business. I was able to do meaningful and rewarding work during my internship. I was treated with respect, given autonomy, and in return, I was able to put my best work forward to make Basecamp the best company and product that I knew how to make.

At Basecamp, I was treated as a thoughtful tech professional. They believe in a 40-hour work week, so that I could enjoy my time outside of work just as much as I love sitting down at my computer to write code. It’s that type of culture that has made Basecamp such a great company, and that same ethos oozes into every part of the product. I found myself at a place that cared much more about the customers than the bottom line. It’s incredibly inspiring and refreshing to see that. I’m now working at Basecamp on Team Data, and I’m looking forward to making my dent, on my own terms. Being at Basecamp is the anti-Silicon Valley, and I couldn’t be happier about that.


Interested in becoming an intern at Basecamp during the Summer of 2017? We’re looking for brilliant managers-of-one who are interested in making a difference while working on real business problems, with a passion to make Basecamp a better place. If that sounds like you, head over to our internship page and apply!