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.

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.

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.

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.

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.

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.

Meet Andy

Basecamp’s new head of marketing, Andy Didorosi, comes on the Rework podcast to talk about how he started a bus company in his hometown of Detroit to help fill a gap in public transit; what he learned about building a business with a “buy one, give one” social mission; and why he left the company he founded to join Basecamp.

If you missed our previous episode on hiring a first-ever head of marketing, you can catch up here!

Nevermore, Amazon

In the spring of 2019, Danny Caine, the owner of the Raven Book Store in Lawrence, Kansas, overheard a customer saying she could buy a new hardcover online for $15. Danny took to Twitter to explain the economics of independent bookstores and the thread went viral, putting the 32-year-old small business in the national spotlight. Danny comes on the Rework podcast to talk about why his activism and outspoken stance against Amazon haven’t just felt right, but been good for business too.