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.

Sponsored By:

• Starting & Sustaining: Thanks for listening. If you're thinking about building your own web application, I've pulled together years of advice and insights from my own experience as well as other founders into a system to help you build and launch your own web application with fewer mistakes and a whole lot less pain.

Links:

• Planscope
• Double Your Freelancing
• RightMessage
• @brennandunn

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.

Sponsored By:

• Starting & Sustaining: Thanks for listening. If you're thinking about building your own web application, I've pulled together years of advice and insights from my own experience as well as other founders into a system to help you build and launch your own web application with fewer mistakes and a whole lot less pain.

Links:

• Travis CI
• @roidrage

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.

Sponsored By:

• Starting & Sustaining: Thanks for listening. If you're thinking about building your own web application, I've pulled together years of advice and insights from my own experience as well as other founders into a system to help you build and launch your own web application with fewer mistakes and a whole lot less pain.

Links:

• Picture This Clothing
• @jaimeejaimee

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.

Sponsored By:

• Starting & Sustaining: Thanks for listening. If you're thinking about building your own web application, I've pulled together years of advice and insights from my own experience as well as other founders into a system to help you build and launch your own web application with fewer mistakes and a whole lot less pain.

Links:

• Feature Upvote
• @featureupvote
• Bootstrapped.fm Discussion Forums
• How to negotiate the Long, Slow, SaaS Ramp of Death by Gail Goodman

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.

Sponsored By:

• Starting & Sustaining: The second edition of Starting & Sustaining will be out in late 2017. Visit the site to get on the list and be the first to know as well as receive a launch discount.

Links:

• Honeybadger
• RailsKits

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.

Sponsored By:

• Starting & Sustaining: The second edition of Starting & Sustaining will be out in late 2017. Visit the site to get on the list and be the first to know as well as receive a launch discount.

Links:

• Happy Herbivore
• Meal Mentor
• Scott Nixon on Twitter

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.

Sponsored By:

• Starting & Sustaining: The second edition of Starting & Sustaining will be out in late 2017. Visit the site to get on the list and be the first to know as well as receive a launch discount.

Links:

• Churn Buster

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.

Sponsored By:

• Starting & Sustaining: The second edition of Starting & Sustaining will be out in late 2017. Visit the site to get on the list and be the first to know as well as receive a launch discount.

Links:

• RachelAndrew.co.uk
• Perch
• Full Transcript

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.

Sponsored By:

• Starting & Sustaining: The second edition of Starting & Sustaining will be out in late 2017. Visit the site to get on the list and be the first to know as well as receive a launch discount.

Links:

• Tracy Osborn
• Hello Web App
• WeddingLovely
• Full Transcript

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.

Sponsored By:

• Starting & Sustaining: The second edition of Starting & Sustaining will be out in late 2017. Visit the site to get on the list and be the first to know as well as receive a launch discount.

Links:

• JW Design
• Blinksale
• Gowalla on Wikipedia
• Full Transcript