Starting & Sustaining

Starting & Sustaining

startsustain.fireside.fm
Candid discussions with folks involved in and around the SaaS industry.
Matt Goldman, CEO of Churn Buster
Jun 16
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 dive into what it's like to…
Rachel Andrew, Cofounder of Perch
Jun 9
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.Special Guest: Rachel…
Tracy Osborn, Founder of Wedding Lovely
Jun 2
Tracy and I talk about her experience building and running Wedding Lovely, raising some funding for it, losing a co-founder, and even going through a heart-breaking acquisition process with Etsy. Through it all, she's kept going and even published books…
Josh Williams, Founder of Gowalla
May 25
Josh and I discuss what it's like going from a bootstrapped small team to a team of 30 in a funded startup. We touch on what it's like going from being a lifelong business owner to being an employee of a large corporation experiencing huge growth. And we…
Thomas Smale, Founder of FE International
May 19
Recently I sat down this Thomas Smale of FE International. Thomas and FE International helped me sell Sifter and made the whole process seem easy. After selling so many online businesses, FE International has the process down to a science, and they've…
Nathan Barry, Founder of ConvertKit
Apr 25
Nathan and I talk about the early days of ConvertKit, reaching a point where he had to make a decision to invest more significantly in it or walk away. He invested a significant portion of his income from other projects and really doubled down to make it…
Courtland Allen, Founder of Indie Hackers
Mar 30
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…
Ruben Gamez, Founder of Bidsketch
Feb 26
Ruben's story with Bidsketch is a great example of how a simple small business can grow into something healthy sustainable on a reasonable timeline. He started out simply with very little in the way of expectations, and bootstrapped the business to…
Allan Branch, Cofounder of Less Accounting
Feb 2
During a time when seemingly everyone is trying to build a product and move away from consulting, Allan is doing just the opposite and moving from SaaS and recurring revenue back to good old-fashioned consulting. We talk a little about the process of…
Drew Wilson, Founder of Plasso
Jan 28
Drew and I discussed his various projects that led him to create Plasso as well as how successful businesses developed out of years of experimentation and cross-pollination. We also talked about some of the differences with bootstrapping versus raising an…
Josh Pigford, Founder of Baremetrics
Jan 15
Josh and I discussed bootstrapping, accepting outside money, the drawbacks of hiring too fast and having to ask his team to take a pay cut. We also talk about how metrics simply aren't important in the early days and how nothing beats spending time to…
Natalie Nagele, CEO of Wildbit
Jan 6
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…
JD Graffam, Serial Acquirer of SaaS Apps
Dec 29, 2016
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…
Tyler Rooney, Cofounder and CPO of Format
Dec 28, 2016
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…
Peldi, Founder of Balsamiq
Dec 26, 2016
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…
Pat Allan, Creator of Thinking Sphinx and Flying Sphinx
Dec 24, 2016
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…
Anthony Eden, Founder of DNSimple
Dec 22, 2016
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…
Mike Perham, Creator of Sidekiq and Inspeqtor
Dec 20, 2016
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…