#infrastructure

Mathias is one of the original founders of Travis CI. In this episode, we talk about the difficulty of leaving the company he helped start, and the challenges of moving on.

Steve McLeod is the founder of Feature Upvote, a SaaS tool to enable your customers to suggest and upvote improvements. In this episode, we talk about and compare his experiences running both a B2C app and B2B app and the value of having a part-time system administrator on retainer.

Matt and I talk about running a SaaS business after acquiring it, the mistakes they made early after taking over Churn Buster, and the common ways that SaaS businesses get dunning wrong and how they can do better. We also talk about the value of iteratively improving automation for tasks and how important it is to clearly document and explain manual process.

Rachel and I talk about what it’s like supporting self-hosted software, juggling a busy travel schedule to make time for work. She’s been working on Perch with her husband Drew for eight years, and they’re still going strong.

Courtland’s story is great because he’s been on a bit of the roller coaster, and now he’s starting fresh with Indie Hackers. He’s interviewing other founders of businesses of all sizes and helping to shed light on what’s possible for small independent software-based businesses. At the same time, the stories are also grounded in realistic stories of slow growth and hard work instead of just focusing on those businesses that hit the jackpot. Courtland’s past experience combined with his discussions with other founders has given him some great perspective and insight on what works and doesn’t work for small software businesses.

Natalie and I talk about bootstrapping, learning that marketing is a necessary part of growing a software company, and the transitions that led Wildbit to be a family-focused company. We touched on the benefits and challenges of running a multi-product company, the inspiration for the various products, and the difficulties of hanging in there as a business gets older and the responsibilities grow and change.

JD and I talk about buying and selling SaaS applications and share some details from the process of selling and transferring Sifter. JD shares what it’s like juggling multiple businesses and how he makes it work, and he dives into the attributes and insights he uses to decide whether a SaaS application is a good opportunity or not and how he does business a bit differently. This is an episode that’s near and dear because I feel like it shares some of the less-often seen aspects of transactions like selling businesses. I really hope you enjoy it.

Format had seven people on the payroll before Tyler even got paid. We talk about bootstrapping in Canada, the amazing story of how they acquired the Format.com domain name, and what it’s like transitioning from a survival mentality to a growth mentality as a business grows.

Peldi and I talk about moving from California to Italy to lower his cost of living to start a company, juggling different delivery formats for software (and the associated payments challenges), giving amazing support, and bending over backwards to help customers. While he originally didn’t want to grow the business beyond himself, Balsamiq is now a team of 23 people based all around the world.

Pat Allan turned his open source side project into a profitable Heroku Add-on. We talk about the advantages and disadvantages of building on another company’s platforms, doing support for both open source users and paying customers, and some of the trickier parts of parlaying open source success into a profitable business venture.

Anthony built dnsimple on the side and didn’t come on board full-time until after there were two other full-time employees. We discussed some of the advantages and disadvantages of running a complex infrastructure product, marketing a complicated business with comics, and fighting domain fraud through it all.

Mike Perham has successfully built a wildly profitable one-man business built on his open source efforts. We discuss what it’s like balancing the seemingly opposing forces of open source and a for-profit business, managing support for the open source version as well as paying customers, and how businesses are all-too-willing to pay for things that provide value or help them save time.