Jason Fried's Blog, page 7

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.

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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.

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

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

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

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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.

BUT.

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.

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“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?”

At the time, I answered this question unsatisfactorily. When asked live on the podcast, I shared only one lesson. Maybe two. 

However, when I deeply reflect on the past 2.5 years of interviewing leaders who I respect and admire, I’ve learned many tremendous insights. I’ve asked each leader the same question – “What’s the biggest leadership lesson you wish you would’ve learned earlier?” – but no two answers have been the same. From the Contributing Editor of Harvard Business Review to the CEO of Lonely Planet, this has held true.

Yet there are a handful of interviews – seven in particular – that have affected me, the most. I’ve changed how I think or how I behave as a leader, because of them.

Here are the seven leadership lessons over 2.5 years I’ve learned from running The Heartbeat podcast that have had the biggest influence on my own management style:

#1:  Stop doing what you’re good at. 

Sometimes, the most counterintuitive leadership lessons are the most helpful. This is one of them. Peldi Guilizzoni, CEO of Balsamiq, shared the most counterintuitive insight with me on The Heartbeat, when he espoused: “Doing what you’re good at hurts the team.” Huh? He explained how when you’re the one always doing the thing that you’re good at, you create a dependency within your team. They can never be self-sustainable or perform at the highest level if you’re the one always doing the things you’re good at. Because of Peldi, when I find myself leaning into a task I’m good at, I now actively ask myself: “Are my actions feeding your team, or my ego?” (You can catch the full podcast episode here.)

#2: Step back. Take stock.

Intuitively, we all know it’s important to take a step back and reflect, as a leader. But for me, it took Natalie Nagele, CEO and co-founder of Wildbit, driving this point home in our Heartbeat interview, for me to act on this wisdom. Natalie admitted how this advice to “work on the business, not in the business” is seemingly cliché. But she emphasized how regularly distancing yourself from problems can in fact help you solve them better, later on. Inspired by her conviction, I started investing more in our own leadership strategy sessions with my business partner and CTO, Daniel Lopes. Now every month, at minimum, we take a day away from the business to step back, and take stock. Big thank you to Natalie, for this. (You can catch the full podcast episode here.)

#3:  Screw the Golden Rule.

“Treat others the way you want to be treated.” This is the Golden Rule we’re all taught growing up. When I chatted with David Heinemeier Hansson (DHH), the Creator of the popular web framework Ruby on Rails and Chief Technology Officer at Basecamp, I realized how backwards this precept was in the context of leadership. David shared with me how you shouldn’t treat other people the way you want to be treated because the other person isn’t you. It’s a poor definition of empathy, if that’s indeed what we do as leaders. Instead, in large part to David, I’m more rigorous than ever about making sure I’m treating others on my team how each individual wants to be treated. (You can catch the full podcast episode here.)

#4:  Good leadership is pruning.

There are no shortage of analogies made about leadership. A leader can be seen as a “coach” or “captain.” But David Cancel, CEO of Drift made an unlikely comparison about leadership in our podcast conversation:  He said that good leadership was like pruning an English garden. It requires small, incremental actions, not big sweeping actions. It focuses on clearing away what’s stifling growth. And, it’s only done periodically – research reveals how managers who are “constantly coaching” overwhelm and exhaust their team. Constant coaching, like constant pruning, can do more harm than good. For me personally, as a leader, this was an important reminder to calibrate my touch points with my team. I’m pruning, not uprooting. (You can catch the full podcast episode here.)

#5:  Transparency requires context, and is on a spectrum.

“How transparent should I be with my team?” As leaders, we’re often faced with this question. We know transparency is supposed to be positive… But to what extent? I so appreciated how Des Traynor, Co-Founder of Intercom, decides what his answer should be. Des revealed to me how transparency “is not about opening up the Google Drive and making sure that everyone can read everything.” It’s about ensuring that people have transparency of context – and that it’s not all or nothing, either. Today, when I consider what and how I should share information with my own team at Know Your Team, I reflect on how well I’m considering Des’ advice. (You can catch the full podcast episode here.)

#6:  Don’t solve the problems yourself.

Leadership is stewardship. We so often forget this. Wade Foster, CEO of Zapier, reminded me of this essential notion. In our Heartbeat podcast interview, Wade acknowledged how in his early days as a leader, he would be eager to roll up his sleeves and solve all the problems for his team. However, this would backfire. It meant his team would always come to Wade with their problems. He became a bottleneck. Now, Wade sees how his role as a leader is to help a team think for themselves – not to solve everything for them. Because of this, I consciously check-in with myself and with my team to make sure I’m practicing this. My measure of success as a leader is how well I’m helping others solve problems. (You can catch the full podcast episode here.)

#7:  If you’re busy as a leader, you’re doing it wrong.

I remember when I interviewed Michael Lopp, VP of Engineering at Slack, his observations around leadership lessons was immediate:  “If you’re too busy doing the actual work, as a manager, that’s a huge mistake.” Michael shared how you can’t truly anticipate nor respond to the needs of your team if you’re in the weeds of the work. You can’t clarify a decision or help sort out interpersonal dynamics. I now remind myself of this constantly, if I find myself too busy, as leader. I ask myself, “How am I making space to listen, respond, and be available to my team, instead of executing the work itself?” (You can catch the full podcast episode here.)

I come back to these seven leadership lessons, almost every week, if not every day. I hope they were as formative for you, as they were for me.

Claire is the CEO of Know Your Team – software that helps you avoid becoming a bad boss. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

Breaking the Black Box

The @AppleCard is such a fucking sexist program. My wife and I filed joint tax returns, live in a community-property state, and have been married for a long time. Yet Apple’s black box algorithm thinks I deserve 20x the credit limit she does. No appeals work.

— DHH (@dhh) November 7, 2019

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 will be available next week 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.

Launch: Basecamp Gets Personal

Since the beginning, Basecamp has been marketed as a project management and collaboration tool for small businesses (or small teams inside larger businesses).

However, over the years we’ve also heard from thousands of people who use Basecamp outside of work. They’ve gone off-label and turned to Basecamp to help them manage all sorts of personal projects too. No surprise there – it really works!

But one complaint we’ve heard is that Basecamp is priced for businesses, not for personal side projects. We felt it was finally time to do something about that.

So today we’re formally introducing Basecamp Personal – a completely free Basecamp plan designed specifically for freelancers, students, families, and personal projects. Why should businesses be the only ones who get to use Basecamp to manage projects? We The People deserve a Basecamp for us, too!

You deserve a Basecamp for home improvement projectsYou deserve a Basecamp to manage your girl/boy scout troops.You deserve a Basecamp to manage your weddings.You deserve a Basecamp to manage your hobbies.You deserve a Basecamp to manage your volunteer projects.You deserve a Basecamp to manage your family events.You deserve a Basecamp to manage your sports teams.You deserve a Basecamp to manage your neighborhood association.You deserve a Basecamp for small freelance gigs.You deserve a Basecamp for personal side projects.You deserve a Basecamp to manage all sorts of personal stuff!

And you want it for free! You got it.

What do I get?
Basecamp Personal includes 3 projects, 20 users, and a gig of storage space. So kick off a couple projects, invite some friends, family, teammates, or volunteers. Stretch your wings a little, and discover the benefits of organizing your personal projects the Basecamp way.

No credit card required. No justification required. No obligation required. No ads. No selling your personal information. It’s Small Tech at its best. It’s The Basecamp Way. Basecamp Personal is on us, for you. Check it out and claim your free account today. We’d love to hear what you end up using it for.

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BTW, if Basecamp Personal sounds familiar, it’s because we used to have a Personal plan way back when. It was $25 per-project. This new one is completely free, so it’s better in every way.

Big Brother at the Office

Between cameras, sensor-equipped ID badges, and keystroke-logging software, employers are keeping an ever-watchful eye on their workers, all in the name of security or increased productivity. Jason Meller of Kolide has spent his career in computer security and witnessed what can happen when a corporation’s obsession with safety results in harmful surveillance of its employees. On the latest episode of Rework, he talks about navigating those ethical boundaries and why it’s important to have constant consent instead of constant surveillance.

A transcript of this episode is also available on the episode page.

Compounding time

I recently started seeing a new therapist. I’ve seen therapists in the past, so that’s nothing new. What is new is the format.

Everyone I’ve ever seen in the past, and likely the person you’re seeing (if you’re seeing someone), runs appointments the same way: An hour a week (or every few weeks). One hour. 60 minutes. The standard time slot for all sorts of appointments.

But this guy I’m seeing does it differently. I see him once every six weeks for six-hours straight. Yes, a six-hour session. And what a joy it is to work on yourself this way.

An hour is barely enough time to figure out what to talk about. And it’s hardly enough time to go deep on anything of substance. By the time you get somewhere, it’s time to go. Know the drill?

But six hours. Six hours an abundance of time to twist and turn. It takes six hours to dig through the rock and strike the seam. I’m loving it.

Further, six-weeks between appointments gives me time to work on the things we uncovered. A traditional week between appointments just isn’t enough time to put in the practice and get to work. You get sidetracked, other stuff comes up, you end up going to the next appointment in roughly the same place you left the last appointment. But six. Six is bliss.

It’s an entirely different approach, and I find it thoroughly refreshing. Yes, it means he can’t work with as many clients. Yes, it means I have to come out of pocket a lot more. And yes, it means it’s a lot of talking, reflecting, feeling, and questioning. It packs a punch, and my mind is definitely mushier the next day. Not unlike next-day’s lingering muscle soreness after a hard workout. But that’s how you get stronger.

It also reminds me just how powerful contiguous time is. The value of time compounds when hours touch hours. And when you string a bunch together, without interruption, the compounding really pays off. Interest compounds. Wisdom compounds. Time does too.

It’s one of the reasons we’re so adamant about making sure everyone at Basecamp has long stretches of uninterrupted time to themselves. Certainly some work is more staccato than others, but at Basecamp people’s days are theirs. The company doesn’t take people’s time with mandatory meetings or heavy process – the company provides the cover so everyone has their own time to use as they see fit.

There are lots of ways to carve up an hour. 10 x 6. 15 x 4. 30 x 2. 45 + 15. 20 + 20 + 20. The key is not to carve it up. And when you stack it up – one full hour after another – you really see the compound benefits of uninterrupted time.

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Note: If this topic appeals to you, we wrote a bunch about the value of time, uninterrupted time, and contiguous time in our latest book “It Doesn’t Have to Be Crazy at Work“.

Rework Mailbag

Jason and DHH are back to answer listener questions on the Rework podcast. In this episode, they discuss whether they prefer reading physical books or the Kindle; talk about providing feedback to rejected job candidates; and imagine a world where Jason and DHH didn’t end up working together.

Back to windows after twenty years

Apple’s stubborn four-year refusal to fix the terminally broken butterfly keyboard design led me to a crazy experiment last week: Giving Windows a try for the first time in twenty years.

Not really because I suddenly had some great curiosity about Windows, but because Apple’s infuriating failure to sell a reliable laptop reluctantly put me back in the market. So when I saw the praise heaped upon the Surface Laptop 3, and particularly its keyboard, I thought, fuck it, let’s give it a try!

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The buying experience was great. There was nobody in the store, so with four sales people just standing around, I got immediate attention, and typed away a few quick sentences on the keyboard. It felt good. Nice travel, slim chassis, sleek design. SOLD!

The initial setup experience was another pleasant surprise. The Cortana-narrated process felt like someone from the Xbox team had done the design. Fresh, modern, fun, and reassuring. Apple could take some notes on that.

But ultimately we got to the meat of this experience, and unfortunately the first bite didn’t quite match the sizzle. The font rendering in Windows remains excruciatingly poor to my eyes. It just looks bad. It reminded me of my number one grief with Android back in the 5.0 or whenever days, before someone at Google decided to do font rendering right (these days it’s great!). Ugh.

I accept that this is a personal failure of sorts. The Windows font rendering does not prevent you from using the device. It’s not like you can’t read the text. It’s just that I don’t enjoy it, and I don’t want to. So that was strike one.

But hey, I didn’t pluck down close to $1800 (with taxes) for a Windows laptop just to be scared off by poor font rendering, right? No. So I persevered and started setting up my development environment.

See, the whole reason I thought Windows might be a suitable alternative for me was all the enthusiasm around Windows Linux Subsystem (WSL). Basically putting all the *nix tooling at your fingertips, like it is on OSX, in a way that doesn’t require crazy hoops.

But it’s just not there. The first version of WSL is marred with terrible file-system performance, and I got to feel that right away, when I spent eons checking out a git repository via GitHub for Windows. A 10-second operation on OSX took 5-6 minutes on Windows.

I initially thought that I had installed WSL2, which promises to be better in some ways (though worse in others), but to do so required me to essentially run an alpha version of Windows 10. Okay, that’s a little adventurous, but hey, whatever, this was an experiment after all. (Unfortunately WSL2 doesn’t do anything to speed up work happening across the Windows/Linux boundary, in fact, it just makes it worse! So you kinda have to stick with Linux tooling inside of Linux, Windows outside. Defeating much of the point for me!).

So anyway, here I am, hours into trying to setup this laptop to run *nix tooling with Windows applications, running on the bleeding edge of Windows, digging through all sorts of write-ups and tutorials, and I finally, sorta, kinda get it going. But it’s neither fast nor pleasant nor intuitive in any way. And it feels like my toes are so stubbed and bloody by the end of the walk that I almost forgot why I started on this journey in the first place.

I mean, one thing is the alpha-level of the software required to even pursue this. Something else is the bizarre gates that Microsoft erects along the way. Want to run Docker for Windows on your brand new Surface Laptop 3? Sorry, can’t do that without buying an upgrade to Windows Pro (the $1800 Surface Laptop 3 apparently wasn’t expensive enough to warrant that designation, so it ships with the Home edition. Okay, sheesh).

The default Edge browser that ships with Windows 10 is also just kinda terrible. I clocked a 38 on the Speedometer 2.0 test, compared to the 125 that my MacBook Pro 13 ran with Safari. (But hey, there’s another beta version of Edge, the one that now uses the Chrominum rendering engine, and that got it to a more respectable 68.)

Anyway, I started this experiment on a Monday. I kept going all the way through Friday. Using the laptop as I would any other computer for the internet, and my new hobby of dealing with the stubbed toes of setting up a *nix development environment, but when I got to Saturday I just… gave up. It’s clearly not that this couldn’t be done. You can absolutely setup a new Windows laptop today to do *nix style development. You can get your VS Code going, install a bunch of alpha software, and eventually you’ll get there.

But for me, this just wasn’t worth it. I kept looking for things I liked about Windows, and I kept realizing that I just fell back on rationalizations like “I guess this isn’t SO bad?”. The only thing I really liked was the hardware, and really, the key (ha!) thing there was that the keyboard just worked. It’s a good keyboard, but I don’t know if I’d go as far as “great”. (I still prefer travel, control, and feel of the freestanding Apple Magic Keyboard 2).

What this experiment taught me, though, was just how much I actually like OSX. How much satisfaction I derive from its font rendering. How lovely my code looks in TextMate 2. How easy it is to live that *nix developer life, while still using a computer where everything (well, except that fucking keyboard!) mostly just works.

So the Surface Laptop 3 is going back to Microsoft. Kudos to them for the 30-day no questions return policy, and double kudos for making it so easy to wipe the machine for return (again, another area where Apple could learn!).

Windows still clearly isn’t for me. And I wouldn’t recommend it to any of our developers at Basecamp. But I kinda do wish that more people actually do make the switch. Apple needs the competition. We need to feel like there are real alternatives that not only are technically possible, but a joy to use. We need Microsoft to keep improving, and having more frustrated Apple users cross over, point out the flaws, and iron out the kinks, well, that’s only going to help.

I would absolutely give Windows another try in a few years, but for now, I’m just feeling #blessed that 90% of my work happens on an iMac with that lovely scissor-keyed Magic Keyboard 2. It’s not a real solution for lots of people who work on the go, but if you do most of your development at a desk, I’d check it out. Or be brave, go with Windows, make it better, you pioneer, you. You’ll have my utter admiration!

Also, Apple, please just fix those fucking keyboards. Provide proper restitution for the people who bought your broken shit. Stop gaslighting us all with your nonsense that this is only affecting extremely few people. It’s not. The situation is an unmitigated disaster.

A Hosty Retreat

Basecamp has taken a clear stance against tracking on the web, so when we learned (via a tweet to DHH) that our podcast hosting provider had introduced listener-targeted advertising, we decided to decamp to a different company. On the latest episode of the Rework podcast, Wailin talks to Lex Friedman, chief revenue officer of Rework’s old podcast host, about what they’re doing with targeted ads. Then she talks to Justin Jackson, co-founder of our new podcast host, about how he’s approached building his startup.