Starting & Sustaining

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 Freelancing. While optimizing the funnel and learning about the importance of personalization, he began to see the opportunity to create an application that could provide easy-to-use personalization for other businesses. After providing these personalization services in the form of consulting, Brennan recognized that the next step was to use his SaaS experience to create RightMessage. We also touch on the logistics of selling Planscope when it was financially intertwined with Double Your Freelancing. It required significant extra time to extricate the financials and clean up all of the books for the sale. Special Guest: Brennan Dunn.

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 affects operations and requires significant attention to the operational side of the business. We also touch on how bootstrapping lends itself to slower and steady growth with a little less stress. We discuss how Travis CI's support of open source projects started out simply as support for the open source community but had the wonderful side effect of great marketing. However, in the case of Travis, scaling to support so many free projects early on wasn't without its own challenges. And we cover some of the challenges of being a german business and doing business internationally while also having a remote team working asynchronously across time zones with nine hours of difference. Special Guest: Mathias Meyer.

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 what it's like running a fledgling business while experiencing viral growth as well as what happens after the viral growth subsides. We dive into what it's like getting viral traffic but not actually making any sales for the first week. We also talk about the importance of launching before you're ready, validating your idea, and making sure to see projects through and not leave them unfinished. Special Guest: Jaimee Newberry.

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 living working 6 hours a day but making you sure you're consistent and show up every day. We also discuss the value of enlisting the services of outside experts like a system administrator as soon as you can afford them. We also touch on the challenges of managing spam and fraud as a business grows and becomes increasingly visible and the importance of thinking up front about what kind of business you want and the type of customers you want to serve. Special Guest: Steve McLeod.

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.

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.

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.

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.

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 what she loves with a small team. Special Guest: Tracy Osborn.

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 insight to building and running software businesses. Special Guest: Josh Williams.

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: Thomas Smale.

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 customers as well as build a relationship and find his first customers. Special Guest: Nathan Barry.

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. Special Guest: Courtland Allen.

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 introvert, the process of recovering after he accidentally deleted all of the customer billing data, and much more. Special Guest: Ruben Gamez.

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. Special Guest: Allan Branch.

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.

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.

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 Nagele.

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. Special Guest: JD Graffam.

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.

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. Special Guest: Giacomo “Peldi” Guilizzoni.

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. Special Guest: Pat Allan.

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. Special Guest: Anthony Eden.

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. Special Guest: Mike Perham.