Bootstrapped

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.Links:Bridget's scheduling tool, YouCanBook.me Bridget's email: bridget@youcanbook.meBridget on Twitter  

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.Links:CooperpressPeter on Twitter 

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.Links:April's websiteApril's book, Obviously AwesomeApril on Twitter  

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.Jane is also co-founder of Userlist. We discuss how Jane's podcasting experience helps with Userlist.Links:The UI Breakfast podcast How to sponsor Jane's podcastUserlistBetter Done Than Perfect podcast 

Simon runs SnapShooter, a service that performs scheduled server backups. We discuss:why backups is NOT a dull businesshow the pandemic pushed him to make the jump to full-timecharging his first customer just $2/month - and quickly learning to charge much morea "I did a rm -rf on the wrong server" storyLinks: SnapShooterSimon on Twitter

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.Email Steve at steve @ barbarysoftware dot comSteve on Twitter: https://twitter.com/steveofmcleod 

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.Show links:Robin on TwitterBlue Cat Reports websiteBlue Cat Reports on Trello 

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.We talk about the upcoming Business of Software online conference, 27 - 29 September 2021, and how Mark's team make online events work.Business of Software websiteUse this code when buying a ticket for BoS Conf: Fall, 2021 for  20% discount: BootstrappedFM  

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.Bootstrapped websiteSteve on TwitterRecommended alternative communities to our now-closed community:Indie Hackers  - if you are just getting started and want to chat with others just getting startedFounder Summit (paid) - if your business is viable and you like to run a calm companyMicroConf Connect - “a space for founders and their teams of independently funded startups to connect with like minded individuals.”MegaMaker (paid) - A community for bootstrappersFind 10 or so people at a similar stage in your businesses and make a private Slack account. 

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.Links:Castos: https://castos.com/TinySeed: https://tinyseed.com/Craig on Twitter: https://twitter.com/TheCraigHewitt 

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.Steve on Twitter: https://twitter.com/steveofmcleodBootstrapped on Twitter: https://twitter.com/bootstrapped_fm 

While Steve enjoys a summer break, Ed Freyfogle steps in this week to interview Adam DuVander. Adam helps companies like yours market to developers.Ed chats with Adam DuVander about his book "Developer Marketing Does Not Exist"Adam on TwitterAdam's siteLearn more about 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.Between recording and publishing this episode, Earnest Capital renamed as the Calm Company Fund.Links:Refiner.ioCalm Company Fund (was Earnest Capital)Moritz on TwitterSAFE agreement   

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.Watch this episode on YouTube. 

Peldi concludes this mini-season with an open and honest discussion with Ed Freyfogle about a problem every business owner eventually encounters. How do you keep at it when you are feeling bored? Are we stuck in our businesses?You can also watch this episode on YouTube.