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.

This week Adam talks with John-Daniel Trask, co-founder & CEO of Raygun. Raygun is an award-winning application monitoring company founded by John-Daniel Trask (better known as JD) and Jeremy Boyd in Wellington, New Zealand. They have revenues in the 8 digits annually, and have done it with very little funding (~1.7M USD). Today’s conversation with JD shares a ton of wisdom. Listen twice and take notes.

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…

Jeff Sheldon is the founder and creator of Ugmonk. Jeff is a designer by trade, and an entrepreneur by accident. I been following Jeff’s journey for the better part of Ugmonk’s existence. I’m also a customer. Jeff and I hold several similar values near and dear to our hearts. In addition to my appreciation for Jeff’s product design abilities, and how he leads his business, I also appreciate Jeff’s awareness and focus on the long hard path.

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.

Lynne Tye is the founder of Key Values, a platform where developers find engineering teams that share their values. To be more precise, Lynne is a solo-founder. She’s also a team of one. Lynne’s path to becoming a founder was anything but typical. She had plans to follow in her parent’s and sister’s footsteps to go into academia, and got two years into pursuing her PhD in Neuroscience before she made one of the best choices in her life — she quit. Lynne has mastered the art of quitting, at the right time of course, and she’s used that art as her secret weapon in her quest to become a founder.

Saron Yitbarek is the founder and CEO of CodeNewbie — one of the most supportive community of programmers and people learning to code. Saron hosts the CodeNewbie podcast, Command Line Heroes from Red Hat, and she’s also the creator of Codeland Conference taking place on July 22 this year in New York City. We talk through getting started, lessons learned, mental health, developing and running a conference…but our conversation begins with a pivotal question asked of Saron…“What are you optimizing for?”

What would be the impact on the world if a Computer Science education was available to you completely free of charge until you get a job in that field paying $50,000 or more? That’s the question that drives Austen Allred and the team behind Lambda School. Lambda School is a revolutionary new school that invests in its students and they completely align their interests with their students. Seems like a novel idea, right? But Austen’s path to Silicon Valley was where things began for him, so that’s where we’ll start today’s conversation.

With JavaScript in every corner of software development and npm in every corner right along with it, the rise of npm can be drawn as a hockey stick up and to the right with Isaac Schlueter at the top grinning ear to ear. After reading their recent announcement to hire a CEO, I knew it was time to talk one-on-one with Isaac about building npm and the journey of hiring his successor.

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.

Kyle Mathews is the founder and CEO of Gatsby, a new company he’s building around an open source project of the same name. Gatsby as a project describes itself as a flexible modern website framework and blazing fast static site generator for React.js. At the macro level — Kyle’s career has been focused on a better way to build and ship websites. It seems he’s done just that with Gatsby’s launch in late May 2015…since then he’s taken on a co-founder and a seed round of $3.8M to form Gatsby Inc.

Donald Fischer and the team at Tidelift are on a mission of making open source work better — for everyone. To pay the maintainers of open source software they are putting a new spin on a highly successful business model that’s a win-win for the maintainers as well as the software teams using the software. In this episode we dig into that backstory and Donald’s journey.

David Cramer dropped out of high school AND college, but that didn’t stop him. He ended up teaching himself programming and eventually landed his first job as the webmaster of a World of Warcraft community website. What a beginning… We talked through “the rough slog” period of Sentry and how David powered through to traction and enough profit for him and his partner to go full time, raise three rounds of funding, and take on New Relic.

Bryan Helmig, Wade Foster, and Mike Knoop started Zapier in 2011 as a side hustle. They ultimately applied to Y Combinator, twice. And this year they hit $35 Million dollars in annual revenue. I talked with Bryan Helmig (CTO) through the backstory of starting this company, being 100% distributed, the flexibility as well as the constraints of being remote-only, how they reached product market fit, growth, scaling their teams, and how they bring everyone together for company wide retreats.

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.

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.

Adam talks with Chad Pytel, founder of thoughtbot.

Adam talks with Dalton Caldwell the Founder of App.net. Since we barely scratched the surface of the planned conversation around what he’s doing with App.net in part 1, Dalton agreed to come back on the show for a part 2 to discuss the back story of App.net!

Adam talks with Dalton Caldwell the Founder of App.net. This is a hefty part 1, mainly focusing on the road traveled by Dalton to get to App.net. We barely scratched the surface of the planned conversation around what he’s doing with App.net. We end this call by teeing up the topic of discussion for part 2.

Francisco Dao, the Founder of 50 Kings (an invitation-only, private community of thinkers and doers) joins Adam to talk about the importance of building relationships, doing only what interests you, entrepreneurship, all sorts of “insider” knowledge around the tech event planning space and more. If you’ve been dying to get invited or referred to 50 Kings, this show will give you all you need to know.

Drew Wilson joins Adam for part 1 to talk about his journey as an entrepreneur, the lows, the highs and the in-betweens. Drew talks with Adam about digital projects, how to chase your dreams and more.

Adam talks with Henk Rogers, Founder of The Tetris Company, Blue Planet Software and Blue Planet Foundation about the beginnings of and the evolution of Tetris, over-coming brick walls, social and mobile gaming, never giving up, changing the world, getting the planet off carbon-based fuels, ending war, creating a backup of Earth and the power of love!