Lessons Learned From 24 Years of Entrepreneurship with Jay Bousada

This interview is a transcript from Inter:views, Cracking The Entrepreneurship Code, with Adrienne Ravez,web3 entrepreneur. It has been edited for length and clarity.

Entrepreneurship is a lifelong journey and not a destination to aim for. While entrepreneurs exist to solve problems in the world, it is not always a walk in the park. It is a cause that demands a different mindset, behavior, and skills.

Jay Bousada, an entrepreneur since 1999, joins me in this entrepreneurship interview to discuss his journey, the pivots he has made, his mistakes, and the lessons he has learned. Jay has all the information for you if you want your business to be bulletproof in any environment or market.

In this interview, Jay shares the power of having a vision as an entrepreneur, among other things. You must have a business vision that should also be well ingrained in the minds of those who work for you. All entrepreneurs also need to understand the importance of boundaries. Let your employees know the values, expectations, ethics, morals, and culture you uphold and ascribe to. Boundaries are the only ways to create a healthy environment in your business.

How did you end up being an entrepreneur?

So, I'll take you back. I live in the Toronto area right now, but I grew up in the Quebec area of Canada in a really small town; I grew up in the 70s and 80s. Back then, one thing that was quite formative for us - and I come from a family of six, I'm the second of four boys - was the fact that Quebec was trying to make sure that they didn't lose their heritage, their culture.

So, they passed a law that outlawed English. My family was English, so I don't remember much from being a youngster, but I do remember some of the challenges we faced back then. My mom was an emergency room nurse. My dad owned a small business in that town that sold furniture, flooring, appliances, and that kind of thing.

And it was a real struggle to try to figure out how to stay in business when your parents can't speak French. It created many habits and the grit and resilience my brothers, and I have today. It probably explains why two of them and I have all started our own businesses, which have all become relatively successful.

I'm happy to say those formative years left an impact, and I've never forgotten some of the lessons we've learned, and I think that's really helped us last the almost 24 years we've lasted. My timing could have been slightly better; starting a digital business in 1999, right before the .com boom happened, was very scary.

Ever since I was a youngster, I remember always being fascinated with trying to somehow improve the world around me. Just remove the friction points. So, whether it was automating something like lights when I was a kid before we had the smart homes that we have today or automating turning on the coffee machine in the morning, those simple little things always seemed like obvious additions to life that would remove friction points.

And as I grew up, becoming an engineer seemed the obvious choice. So, I went about doing that and had the good fortune of working in a couple of different engineering firms, learning a lot about problem-solving, the process of breaking down a problem and sequencing out a solution, and all those things.

I also learned what I didn't want in business. Some of those professional service firms could not really understand where the real power of an organization comes from. And I think it comes from its people. Many smart people don't seem to have the appropriate audience or voice with senior management, and great ideas go unseen; they go unheard. And so, a business is less for it. And I knew that when I started Thrillworks, I definitely wanted to bake into the process.

It was right around the time that I was having a lot of success as an engineer. My bosses called me into the office one day, and they said to me, hey, we'd like to promote you to this job that would require a three-year commitment on my part. It was a highly sought-after role inside the organization, and instead of accepting it enthusiastically, I quit on the spot. They didn't know I was running Thrillworks in my off hours and was just fascinated with web technologies and building things with this code base that would run on any computer anywhere. HTML was just ubiquitous to every computer at the time. And it was fascinating to me that you could write code that would run on any existing computer, never mind the fact that all these computers were interconnected.

So, when I announced that I was quitting, they backtracked quickly and said, oh my God, no, you don't have to quit; keep your job. And I said, no, I've really got to pursue this opportunity. So, I went home that night, and I told my wife at the time that I just quit. And back to the poor timing on my part, she was nine months pregnant with our first child.

Thankfully after starting Thrillworks, we landed some great clients, and it really saw us through the rough part of the .com boom. We built momentum, which had much to do with how we approach business here.

Obviously, any product or solution you put forward must include a great deal of quality that's just non-negotiable if you want to stay in business. But our approach to business is quite different, and I think that's seen us through so many iterations of what the internet has become and what business throws at you. We've been fortunate to capitalize on the luck coming our way and work with some amazing customers. And that led us to where we are today.

Can you identify for us the different stages of your business growth?

Absolutely, I can. I started it as just one person building websites for businesses in the area. Very quickly, I got a reputation for delivering on time and building what the customers were looking for, so I had a few agencies at the time that came knocking. It wasn't long before I ended up hiring two or three people.

Shortly after, I took on a business partner for a while and bought him out. But after we got things rolling, because we actually showed up a little bit differently than other businesses did; our focus was first and foremost to ensure that our customers felt heard.

So instead of walking in as the expert and telling our customers exactly how we would do things, we started by trying to get to the bottom of what problem they were trying to solve with this new thing called "the internet". As soon as our customers actually experienced that, it didn't matter who we were competing against. Our customers really fell in love with the process of getting a chance to express the problem that they were trying to solve or the opportunity they were trying to capitalize on, and that really built deep relationships with our customers that saw us through a lot of the internet challenges and the explosive growth that came along.

We reached about 12 people, probably around year eight, and I realized that my business partner and I were seeing the world differently, which was causing confusion inside the business. We needed a unified vision if we were going to run the company, and that wasn't going to happen. So it was at that point that we decided to part ways. I took the business in the direction that I intended: be creative, be innovative, bring solutions forward to our customers, don't wait to be asked, solve a problem, spot the problem, and proactively propose solutions to them.

That grew us to about 15 or 16 people. We had some very recognizable clients, everyone from Canada's largest energy company to Blackberry at the time, Tim Horton's, one of our largest fast-food retailers in the country. But we had gotten too big for me to participate in projects at that point.