#selling

Brennan is a co-founder of Right Message. In this episode, we talk about the path he’s taken that led him to create Right Message and what he’s learned about building and launching SaaS applications based on his experiences with his various products.

Mathias is one of the original founders of Travis CI. In this episode, we talk about the difficulty of leaving the company he helped start, and the challenges of moving on.

Ben and his co-founders started Honeybadger after a bad experience with an existing exception tracking tool. With a focus on customer service, they’ve successfully bootstrapped it into a healthy and sustainable full-time endeavor.

Scott Nixon is the co-founder of Meal Mentor, a subscription-based vegeterian meal planning service. Scott handles the technology side of the business and works to keep the operational side of things humming with software.

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 talk about the value of iteratively improving automation for tasks and how important it is to clearly document and explain manual process.

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.

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.

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.

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.

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.

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.

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.

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.

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.