Starting & Sustaining
Starting & Sustaining originally began as a book and spreadsheet (https://get.startingandustaining.com) created to help people start software businesses. That evolved into candid discussions with people involved in software businesses in one way or another. Focused primarily on the trials and tribulations of launching and running a software business, Starting & Sustaining attempts to break down the hurdles to help you build and launch your own software business with less pain and fewer mistakes.
Episodes
August 14, 2018 • 46 mins
Brennan and I explore the trajectory of businesses and learning that led him to create RightMessage.
Since founding his first SaaS application, Planscope, in 2011. Brennan began producing courses to help freelancers grow their business as a way to grow Planscope. However, as the content arm of Planscope grew, it became the primary breadwinner.
Brennan eventually sold Planscope to focus on the content production with Double Your Fre...
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July 31, 2018 • 49 mins
After helping found Travis CI and grow into the CEO role over six years, Mathias recently left Travis and starting helping other companies with their growth challenges. We talked about the difficulty of leaving and moving on after six years and the tactics that have helped him work through it.
We also talk about the operational side of growth. While we all want revenue to grow, sometimes, we fail to think about how that growth affe...
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July 17, 2018 • 41 mins
Picture This Clothing went viral immediately. From the outside, it looked like every entrepreneur's dream. But the reality of holding together a business that just went viral is completely different. Add in the logistics of printng custom shirts on demand and fulfilling the orders, and it's not all it's cracked up to be.
Jaimee and I talk about the necessity of creating space in your life for opportunities to take hold. We explore ...
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July 10, 2018 • 38 mins
After years running a company based on a consumer product, Steve made the decision to switch to a business-focused product in Feature Upvote, and he's never looked back. We explore the implications of legal changes having the ability to wipe out 55% of your customer base after the United States changed the laws around online gambling.
We compare the differences between Steve's B2C and B2B experiences, the ability to make a healthy ...
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October 9, 2017 • 37 mins
Ben and I discuss the origins of Honeybadger, what it's like bootstrapping, and the sleepless nights brought on by running an infrastructure product. We also talk about Ben's experiences automating the company and growing it into a more mature and resilient business. Special Guest: Ben Curtis.
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August 13, 2017 • 52 mins
Scott and I discuss the hybrid nature of running a business where software merely facilitates a primarily offline interaction. How do you measure engagement? How do you know if the customer succeeds? He makes a great case for giving consumer-oriented software businesses another chance. Sure they have high-churn, but there's also many more consumers out there than businesses. Special Guest: Scott Nixon.
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June 16, 2017 • 45 mins
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 acquire a SaaS business and how central trust is to the process of transitioning an application to a new team. Special Guest: Matt Goldman.
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June 9, 2017 • 41 mins
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 Andrew.
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June 2, 2017 • 46 mins
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 to help others build their own web applications. She's a brilliant example of someone that simply won't give up, and while there's no IPO looming, she's making a great living doing ...
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May 25, 2017 • 54 mins
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 talk about some of the differences between building a small profitable business and hitching your wagon to venture capital. Simply put, Josh brings some great perspective and deep ...
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May 19, 2017 • 35 mins
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 been able to pick up on quite a few trends. So Thomas takes some time to share what they've seen and what matters when it comes to buying or selling an online business. Special Guest:...
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April 25, 2017 • 47 mins
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 work long before it was obvious things were going to take off. He talks about his sales process and how it simultaneously helped him better understand the needs of potential custom...
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March 30, 2017 • 32 mins
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 ...
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February 26, 2017 • 41 mins
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 profitability it on the side of a full-time job and now manages a remote team of four additional people. We talk about the challenges of growing and managing a remote team as an introver...
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February 2, 2017 • 33 mins
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 selling LessAccounting, the ups downs of trying to grow a SaaS application, and some ways to take a step back and make sure that you're working on things you're passionate about. Speci...
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January 28, 2017 • 39 mins
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 angel round through Drew’s experience on both sides. Special Guest: Drew Wilson.
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January 15, 2017 • 37 mins
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 talking to your customers in person. Special Guest: Josh Pigford.
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January 6, 2017 • 37 mins
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. Special Guest: Natalie ...
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December 29, 2016 • 50 mins
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 lik...
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December 28, 2016 • 48 mins
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. Special Guest: Tyler Rooney.
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