How I got hired by Basecamp

I saw the Senior Programmer offer one day before going to bed. I decided I wasn’t going to apply. I had tried four times since 2013, and I never got to pass the first filter. Each attempt took me a good amount of time and energy, and I didn’t want to go through that pain again. That feeling didn’t last much: the next day, I was already working on my application. 

I knew I had made a mistake in the past: a too long cover letter. So this time I decided to fit it into two pages:

  • The letter itself on one page.
  • A distilled list of my relevant projects and articles on another.

The self-imposed two-pages constraint was arbitrary but served its purpose: reducing my big initial dump of assorted ideas and projects into something essential and easy to digest.

I decided to add a third page with a “Basecamp timeline” of my previous attempts. I wanted to highlight my genuine motivation, as well as referring to a demo I prepared years ago. I considered this secondary, so I placed it as a light appendix at the end.

I tried to make the application look nice with my limited design skills. They asked for a PDF, but I didn’t want to deliver a boring document. This was the version I sent.

They liked the application, and I was asked to do a technical exercise. Not too big, but interesting and fun. I could solve it on my own terms, and it let me show some technical and communication skills. Then I had three interviews: one with Andrea, the Head of People Ops; another with members of the team: Rosa, Jane, and Justin; and a final one with Jeremy, the team lead. Each interview left some candidates out, and I always knew how many of us were left.

Interviews were not hard. No difficult questions or puzzles. They felt like chatting about my background and Basecamp with colleagues. They tried to make me feel comfortable and gave me their full attention, which was a big contrast with other past experiences I have had. I listened to this episode about how Basecamp hires many times during the process, and it is a pretty good depiction of what to expect.

Because I imagined how good other candidates would be, I always thought it wasn’t going to be me. At first, that worked as a self-defense mechanism against the likely rejection. But the final interviews, when I knew I had a chance, were incredibly nerve-wracking.

I hate describing rare fantastic outcomes as just the logical consequence of some actions. I am proud of the job I did but, when it comes to selecting people, there is no best or right, and I was very lucky to be the one. Said that, I hope sharing my cover letter and experience can inspire other future candidates, like I was inspired by others Basecampers before.

6 mistakes to avoid during your first 30 days as a new manager

You’re bound to make mistakes as a new manager – but here are the biggest, most common pitfalls to avoid in your first 30 days as a new manager.

I’ve never quite known the proper word to describe the feeling of being simultaneously elated and terrified — but your first 30 days as a new manager is that feeling.

You don’t want to mess this up. You’ve been reading The Effective Executive and High Output Management, googling “management 101” and “first 30 days as a new manager”, and talking to mentors about the “should’s” and “should not’s” of leadership… all in hopes that you won’t make any egregious blunders during your first month on the job.

But quite frankly, it’s bound to happen. You’re going to make a mistake, or two, or twenty. When we’re new as leaders, we operate out of instinct. It’s an instinct formulated from what our former bosses have done, honed by our own value system of what we personally prefer, and our best guess for “So I think this will work?” But we don’t really know if it’ll work.

That’s where I can help 🙂

Keep reading “6 mistakes to avoid during your first 30 days as a new manager”

The one-on-one meeting template for your end of the year review

What should you do for your end-of-the-year review with an employee? Use this one-on-one meeting template.

With December upon us (already!), many managers have been asking me if I have a one-on-one meeting template for their end-of-the-year review with a direct report.

Yes, I do have one 🙂

The end of the year is an opportune time — an ideal time, truly — to reflect together with your direct report, on what went well, what didn’t, in what they were most encouraged, and in what ways they weren’t.

Keep reading “The one-on-one meeting template for your end of the year review”

Lab Week

Get out your Bunsen burner! It’s time to do some experiments. In the latest episode of the Rework podcast, we talk to two businesses that aren’t afraid to try new things. First, the three founders of The Mad Optimist, a soap company in Indiana, talk about letting customers choose what they pay for their products. Then Natalie Nagele, the co-founder and CEO of software company Wildbit, talks about an ongoing experiment with four-day work weeks and what she’s discovered about productivity, happiness, and deep work.

Venture Capital and Control with Dave Teare

Dave Teare is the co-founder and official “heart and soul” of 1Password, which recently raised $200 million in its first round of venture capital. Basecamp is a longtime happy customer of 1Password and also a longtime critic of venture capital, so the funding announcement led to some back-and-forth on Twitter between Basecamp co-founder David Heinemeier Hansson and Dave Teare. In the latest episode of the Rework podcast, DHH and Dave get on the phone to hash out their feelings about venture capital and what this funding round means for 1Password’s future. (A transcript is also available on the episode page.)

If you’re new to Rework and enjoyed the conversation between Dave and DHH, be sure to check out this episode where DHH and Automattic’s Matt Mullenweg get on the phone to discuss power in open source communities. And subscribe to Rework via your favorite podcast app so you get our new episodes as soon as they’re released.

Calm in the Political Storm

Workplace cultures in politics and tech share many similarities: Overwork is glorified; long hours are the norm; employees are expected to respond to communication instantly, no matter the day or time; and those that opt out are seen as lacking hustle or ceding ground to competitors. Marty Santalucia, a political consultant in Pennsylvania, wanted to do things differently. In the latest episode of the Rework podcast, he talks about applying calm work principles to an industry that’s known for the opposite dynamic.

The joy and power of being the independent underdog

I was up late last night and watched Tesla’s Cybertruck announcement. I was immediately energized watching creative people shaking up an entire industry with a completely new, super weird design vision. I ABSOLUTELY LOVE IT when people do this.

Will this bizarro truck sell? Who knows. It almost doesn’t matter. Its mere existence will put a deep dent in the brain of every single person who sees it. This is going have long-term ripple effects for what people imagine as possible in car design. We’ve had 3 decades of vaguely bubbly, rounded-edge, safety-first cars churned out by every manufacturer, and now there’s something new on the menu.

If you walk back a few years, there are other moments like these…

Volkswagen made a little rounded car for working people when everything else out there was big and expensive and brutal.

Apple released a colorful bulbous computer loaded with personality, when everyone else was shipping ugly rectangular beige boxes.

Some upstart web design punks made a project communications app that worked nothing like any of the other tools at the time.

Panic invented a simple monochrome handheld game system (with a crank!?), in an era when people expect big color screens and byzantine features.

What did these companies and products all have in common?

They were independent underdogs. They didn’t have to settle for people’s preconceived expectations for products or markets or advertising or anything. They didn’t have to ship a million units—they could ship a thousand units and that’d be plenty great. They could chase whatever ideas they wanted to chase, because they didn’t have to answer to anybody.

It’s hard to be the underdog. Building a viable profitable business is unbelievably tough. You usually don’t have the resources you need, and people don’t take you very seriously. The deck is stacked against you in countless ways.


It’s powerful to be the underdog. Creatively, it’s the best place to be. There’s no other circumstance where you can continually try your wildest creative pursuits and see them through to fruition.

I used to think that the goal of an independent underdog should be to become a massively successful Top Dog, but I was dead wrong. You don’t ever have to do that. You can stay independent, keep doing exactly what you want for your whole career, and have a joyful time along the way.

Don’t believe me? Take a look at my favorite independent underdogs, They Might Be Giants. They stayed true to their deeply weird vision through 4 decades and 20+ albums in a constantly changing industry that spits out even the toughest cookies. Are they on the radio? No. Have they maximized their revenue growth potential? No. Do they have a fervent fan base and total creative freedom to make the stuff they want to make? Hell yes!

We need a lot more underdogs. You can become one today. Please stop reading this immediately and go invent some Cybertrucks.

Spending in the Clouds

Basecamp has cut back its reliance on Amazon and Google, but there’s one area where it’s tough to find alternatives to Big Tech: cloud services. Even so, there are ways to cut spending on this $3 million annual expense while keeping the company’s apps running smoothly. In the latest episode of the Rework podcast, Blake Stoddard on Basecamp’s Ops team talks about how he volunteered to look for savings on cloud services and really delivered—to the tune of over a half-million dollars.

A transcript of this episode is also available. And if you like what you hear, be sure to subscribe to Rework in your favorite podcast app so you get all of our new episodes as soon as they’re released.

7 leadership lessons over 2.5 years

Over the past 2.5 years, I’ve interviewed 49 leaders for our podcast on leadership, The Heartbeat. These are the leadership lessons that have influenced me the most, personally.

“What are the biggest leadership lessons you’ve learned from others, that have changed or affected your own management style?”

No one had ever asked me this question before – let alone on my own podcast show – until recently.

Who asked me this? None other than Jason Fried, CEO and co-founder of Basecamp. I’d invited Jason back on The Heartbeat, our podcast on leadership, for our 50th episode. He’d been our very first guest back in 2017 when I started the show. (Jason also sits on our board and originally spun out Know Your Team back when it was a part of Basecamp).

For this 50th anniversary episode, I thought I’d turn the tables: I asked Jason if he might interview me. And so, Jason asked me this never-before-asked question, “What are the biggest leadership lessons you’ve learned from others, that’s changed or affected your own management style?”

Keep reading “7 leadership lessons over 2.5 years”

Breaking the Black Box

DHH sparked a national controversy this week when he posted a series of livid tweets about how his wife received a much lower credit limit than he did on their Apple Cards, despite applying with the same financial information. What began as a rant against opaque algorithms turned into a regulatory investigation and more.

We wanted to dive deeper into some of the issues that (re) surfaced in this dust-up, so we put together a special episode of the Rework podcast featuring Dr. Ruha Benjamin of Princeton University and entrepreneur Mara Zepeda. Ruha, the author of Race After Technology, discusses algorithmic bias and how our propensity to rely on technology for fixes to systemic problems often results in more discrimination against marginalized communities. Mara, who’s helped create organizations such as the XXcelerate Fund and Zebras Unite, talks about the “capital chasm” that persists for women and people of color who are trying to navigate the financial system.

Both women share ways that everyone can get involved to interrogate these systems and their underlying technology, and they discuss how to move from “paranoia and paralysis,” as Ruha says, to a place of action to build something better.

A transcript of this episode is available on the episode page. And if you’re new to Rework and like what you hear, please do subscribe via your favorite podcatcher app! We’ll have two episodes next week, our regular Tuesday one and a bonus later in the week about the launch of Basecamp Personal.