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.
Mike McDerment is the founder and CEO of FreshBooks. Believe it or not, Mike became a founder by accident. Like many of us, Mike had an itch that he just had to scratch. One thing led to another and soon enough FreshBooks became a key tool in the belt of many freelancers and agencies looking for an easy way to send invoices and get paid quickly online. We talk through the early days of FreshBooks and how things came to be, why they created a secret competitor to iterate on a bold idea for the future of FreshBooks, and we also cover what keeps Mike excited.
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.
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.
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.
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.
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…
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.
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.