Episodes

I conclude the mini season of interviews with a brief summary of the five interviews I conducted. A few weeks ago, my cohost had a cycling that student that broke his jaw. As a result he had to take a break from the podcast while he was recovering. In the meantime, I invited a few people to come onto the podcast and talk about their businesses, their work and themselves.

Bridget is co-founder and CEO of YouCanBook.me, an online scheduling tool. I chat with Bridget Harris about the 10-year journey of starting and growing her company as a bootstrapped SaaS. Amongst other things we discuss the financial sacrifices bootstrappers have to make in a rapidly growing business.

I chat with Peter Cooper, who runs several email newsletters, including JavaScript Weekly, Ruby Weekly, React Status, and Postgres Weekly. These all live under the collective banner of Cooperpress.

April Dunford has a well-deserved reputation as the expert in product positioning within the tech industry. April and I discussed how bootstrappers can go about product positioning.

Jane Portman is the host of UI Breakfast, a podcast covering UI/UX design, products, marketing.  Jane recently crossed the  2 million downloads milestone. Jane and I discussed the journey from the first episodes, with almost no listeners, to where she is today.

Simon runs SnapShooter, a service that performs scheduled server backups. We discuss:

Ed is recovering from an accident, so Steve goes solo in this episode. Ed's accident gets Steve musing on the unpredictability of life, and what we can do to partly prepare ourselves and our businesses for this. Steve then abruptly changes topic and challenges all listeners to make a bold pricing experiment.

Three-time guest Robin Warren, founder of Corrello, achieves "very infrequent guest co-host" status. We chat about a number of aspects of mental wellbeing for bootstrappers - getting out of the house, taking breaks, dealing with boredom, and making your business less dependent on you.

Ed and Steve talk about the challenge of continuing to learn how to run our businesses better, and the challenges we encounter in ongoing learning.

It’s good to take a break!

In this episode Ed and I get self-indulgent and talk about our vacations. From time to time we make a tenuous link between our vacations and our  bootstrapped businesses.

If you've ever thought of selling your business, or acquiring one, you'll enjoy this episode. Matt Zeunert, founder of DebugBear, was curious about the details of my acquisition of Saber Feedback. So we switch roles for this episode, and the guest became the interviewer. Matt asks the questions, and I answer!

Mark Littlewood runs the Business of Software, a series of annual conferences to help us run our software companies better. Mark very openly shares how COVID-19 has hit his business, and his need to adapt almost overnight.

In this solo episode, I talk about successful yet quiet SaaS business all around us. I also tell the full story of why our forum has been closed and put permanently into archive mode.

Peldi, founder of Balsamiq, drops by. We discuss two unrelated topics. First, resellers - why they exist and how to accommodate them. Second, the challenges and benefits of having a podcast for your product.

Ed and Steve go in deep on some enterprise sales work they've both been doing lately for their bootstrapped, mostly self-service SaaS products.

Craig Hewitt runs Castos, a podcast hosting and analytics company. He returns to the show to talk about why he recently sold a chunk of his bootstrapped company to a round of investors.

It's 15 months since I acquired Saber Feedback. I talk about the challenges I've faced so far, the bottleneck I'm currently facing, and where things are headed.

While Steve enjoys a summer break, Ed Freyfogle chats with Adam DuVander, who helps companies like yours market to developers, about his book "Developer Marketing Does Not Exist".

Moritz Dausinger, three-time bootstrapper, tells me why he recently sold a small stake of Refiner.io to Earnest Capital.

Ed and Steve discuss what it is like when a core team member quits, how to reduce the chance of it happening, and how to make our businesses resilient enough to handle it.