Founders Talk

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In-depth, one-one conversations with founders, CEOs, and makers

Founders Talk Founders Talk #54

From side project to $7.25M for Unsplash

When Mikael Cho started Unsplash from its small beginning as a Tumblr blog and side project, he had no idea it would have such a huge impact and ultimately disrupt the photography industry. In this episode, Mikael shares the backstory of Unsplash, how it got started, keeping things focused, levers of growth, flipping the marketing funnel, turning free into a business, raising $7.25 million to build a new economy for photography, and the impact of an API.

Founders Talk Founders Talk #91

Fireside chat with Jack Dorsey

Adam was invited by our friends at Square to interview Jack Dorsey as part of their annual developer conference called Square Unboxed. Jack Dorsey is one of the most prolific CEOs out there — he’s a hacker turned CEO and is often working at the very edge of what’s to come (at scale). Jack is focused on what the future has to offer, he’s considered an innovator by many. He’s also a Bitcoin maximalist and has positioned himself and Block long on Bitcoin.

What you’re about to hear is the fireside chat Adam had with Jack at Square Unboxed 2022. Jack and Adam discuss the vision Square has for the developer platform and why it’s so central to the company’s strategy.

Founders Talk Founders Talk #60

Leading data-driven software teams and products

For the final show of 2018 I’m talking with Travis Kimmel, the CEO of GitPrime. Travis has spent years as an engineering manager. Travis’s mission at GitPrime is to bring crystal clear visibility into the software development process and bridge the communication gap between engineering and stakeholders. This communication gap is often an ongoing plague in product development lifecycle. We talked through focus, tech debt, leading teams, predictability, and more.

Founders Talk Founders Talk #73

Balancing business and open source

Raj Dutt is the founder and CEO of Grafana Labs. Grafana has become the world’s most popular open source technology used to compose observability dashboards (we use Grafana here at Changelog). Raj and team are 100% focused on building a sustainable business around open source. They have this “big tent” open source ecosystem philosophy that’s driving every aspect of building their business around their open source, as well as other projects in the open source community. But, to understand the wisdom Raj is leading with today, we have to go back to where things got started. To do that we had to go back like Prince to 1999…

Founders Talk Founders Talk #70

Leading GitLab to $100M ARR

Sid Sijbrandij is the Co-founder and CEO of GitLab — an all-remote company and complete DevOps platform. As a company, they have their eyes set on taking the company public to IPO and they’re very outspoken about their culture, open handbook, and how they work as an all-remote company. We talk through where Sid came from, the early days of GitLab, why IPO vs a private sale (like GitHub), what it means to put “family and friends first, work second,” how we should view work, and his biggest fear — the company failing.

Founders Talk Founders Talk #75

The journey to massive scale and ultra-resilience

This week Adam talks with Spencer Kimball, CEO and Co-founder of Cockroach Labs — makers of CockroachDB an open source cloud-native distributed SQL database. Cockroach Labs recently raised $160 million dollars on a $2 billion dollar valuation. In this episode, Spencer shares his journey in open source, startups and entrepreneurship, and what they’re doing to build CockroachCloud to meet the needs of applications that require massive scale and ultra-resilience.

Founders Talk Founders Talk #53

Starting over from zero

Danielle Morrill joined the show to talk about how she’s starting over from zero after the recent acquisition of Mattermark to FullContact where she held the role of CEO and co-founder who walked away with “zero dollars and a job”. We talked through the details of the company, the acquisition process, the deal — which she brokered herself — as well as her outlook on the startup grind and silicon valley today, and what she’s planning to do next.

Founders Talk Founders Talk #66

Failing to build a billion-dollar company

Sahil Lavingia is the founder and CEO of Gumroad, a platform for creators to sell the things they make. Since 2011 Gumroad has sent over $200 million dollars to creators. That’s a big number. Sahil’s ambitions lead him to believe that Gumroad would become a billion-dollar company, have hundreds of employees, and eventually IPO. That didn’t happen.

…we were venture-funded, which was like playing a game of double-or-nothing. It’s euphoric when things are going your way — and suffocating when they’re not. And we weren’t doubling fast enough to raise the $15M+ Series B we were looking for to grow the team. For the type of business we were trying to build, every month of less than 20 percent growth should have been a red flag. But at the time, I thought it was okay…

We talk through Sahil’s journey with Gumroad, why it failed to meet his goals, the path he’s on today and the things he now values…but to understand why Gumroad didn’t live up to his expectations, we really have to understand the backstory of Gumroad.

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