Chris Prendergast

Occupation: CEO and founder of Jamstack, maker of a portable amplifier that attaches directly to an electric guitar

City: Markham, Ont.

Age: 31

I’ve been investing in my business for: Just over two years. I began working on the idea for Jamstack in 2015, and quit my day job at a startup education company in November 2017 to devote myself full-time.

Portfolio: Pretty much my entire net worth, except my car, is in my business.

Working with my advisor: Since January 2018. He’s one of my investors, and we’ve been focusing almost exclusively on the business. He made sure that I have life insurance for both the business and my family: my wife, Hollie, and our two sons, Micah and baby Emery. But now, with the possibility of growing or selling the business, it’s time to engage in financial planning on a personal level.

Trading a pension for passion

I taught science to middle schoolers for three years. The idea was to get in with the school board, have a steady job and collect a pension. But I was teaching at a private school, which didn’t pay very well, and there wasn’t much room for advancement. When I was approached by a startup education company in 2013, I decided to change tracks. I loved their mission, but after four years, my net worth was flat—my wife was waitressing at the time and making more money than me. We wanted to get into the housing market but couldn’t afford to. I had started to show the Jamstack prototype to people, and began to think I could make a real go of it as a business. My wife and I had some hard conversations, and we decided that we needed to take the chance on it, that I would regret it forever if I didn’t. At that point, mediocrity seemed like a bigger risk than trying to do something special.


I desperately needed startup cash. My dad gave me an initial $12,000 (he considers it an investment in his long-term retirement care), and then I pitched the Jamstack idea to an industrial design firm that was willing to make a prototype and go in with me on a crowdfunding campaign. The campaign required $45,000 to pay for things like a manager, a Facebook ad specialist and photographs.

Futurpreneur Canada gave us $15,000 and the Business Development Bank of Canada supplied another $30,000. Our first crowdfunding campaign, on Kickstarter, raised about $85,000. We learned a lot, and launched a second campaign on Indiegogo, which raised US$370,000. Now, we’re cultivating private investors.

The entrepreneurial spirit

Most entrepreneurs have their money and their goals completely tied up in their businesses—they’re not going to be that open to taking a chunk of their income and putting it into a mutual fund each month, at least during the beginning stages. Now that I’m drawing a salary, I can think a bit more about that kind of thing. My goals are to draw a much larger salary, and then, eventually, sell Jamstack. I’ll need someone to help me figure out what to do with the proceeds. I need a financial advisor who understands that mindset and those goals, and who can help with tax strategies and planning, incorporating the business and investing in real estate. Because my advisor is also an investor, he gets that.