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Oct 11, 2018

On today’s Just the Tips, we talk with Matt Watson, who had enormous success early in life as co-founder of Vinsolutions, and after selling that company for $150 million, started Stackify to solve the biggest problems he had at Vinsolutions. Matt tells us about his early days, how he sort of fell into work on Vinsolutions and how it went from side hustle to major hustle. And he shares his unique insights as a developer and an entrepreneur, and how his parents’ entrepreneurial spirit inspired him as a kid. He’s no Dean “Pigeon Man” Holland, but Matt has a great story to tell.

The “back of a napkin” story come to life

Matt’s story as an entrepreneur literally starts with the apocryphal “back of a napkin” at Applebees. Matt was selling computers at Sears in the early aughties when a customer came in and asked if anyone could help him with a software solution. Matt volunteered and became a de-facto cofounder. After two years of getting Vinsolutions off the ground, he was able to quit his job, and then after another six years sell it for nine figures. It’s something of a meteoric rise, but it also speaks to Matt’s work ethic and eye for solving a market’s problem. And one of the fascinating things he says on this episode of Just the Tips is how they never got into a “startup” mindset. They were just running a business.

Solve the problem you see in front of you

Matt’s time at Vinsolutions let him peak behind the curtain a bit, and see what problems both businesses and developers were wrestling with. And so that’s how he started Stackify, which essentially lets businesses see how well their applications are performing. In other words, if you go to a restaurant’s website and order food, and the application you’re ordering through is slow or crashes, you’ll likely lose that customers. So Stackify lets a business see how well an application is running, how satisfied customers are, etc. It’s a really savvy approach, one forged in the fires of running a large business.

How do you decide when to add features and when to focus on stability?

One of the interesting things about the software space right now is that there’s huge pressure to constantly add features and iterate. As Matt says, agile development is the name of the game right now, but it can be a difficult balance to strike between having a stable software solution and adding more bells and whistles to it. As Dean says, he’s dipping his toe into software development, and has really tried to focus on having the software just do one thing, so it stays as simple as possible. And as Matt says, that’s very important when you go to market.

Why Matt invested in content marketing

One of the problems Matt discovered with Stackify was that it was really difficult to reach his target audience. Senior software developers tend to use ad blockers and other means to avoid being marketed to. So his company released a free tool for developers that became popular and served as a calling card, and then he also turned to content marketing. And he has a very unique way of going about content marketing. He calls it a three-pronged approach. What are they? You’ll have to tune into this week’s episode of Just the (Prong) Tips to find out.

Outline of This Episode

  • [3:00] How Matt got started with VinSolutions in 2003
  • [8:12] How Vinsolutions didn’t operate like a startup
  • [10:05] What is Stackify?
  • [12:48] How do you decide when to add features and when to focus on stability?
  • [15:30] Why Matt invested in content marketing
  • [18:34] Content marketing is a long game
  • [21:30] SEO is really about creating quality content
  • [24:20] Matt’s advice for people starting a business
  • [28:38] What Matt has learned not to do

Musicfor “Just The Tips” is titled, “Happy Happy Game Show” by Kevin MacLeod ( Licensed under Creative Commons: By Attribution 3.0 License

Resources Mentioned

Connect With James and Dean

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