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.

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.

“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.

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 projects
  • You 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.

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.

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.