Lessons Learned From 24 Years of Entrepreneurship with Jay Bousada
Updated: Jun 14
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.
So, I started backing away from the projects, and this is where, in hindsight, I learned one of the most valuable lessons that I've learned as a business leader. And that is, if your vision isn't crystal clear in the minds of the people working for you, your secret formula for success requires you to be there every day. And so, the only way to scale and empower smart people to move at speed and do their job well is for them to understand the company's vision, and I didn't do that around year 12.
In year 12, we were having great success, but things started getting much harder from year 12 through year 17. So, from 2012 to 2017, I didn't publish the values we were making decisions with and the company's vision. As a result, many people were making the decisions they thought I would want them to make, but they weren't really the decisions I wanted the company to make.
And so, one day in 2017, when I walked in, I realized I did not love what we had become. We had drifted really quite far from the success that we were having up to 2012. And I had three choices. I could sell the company, shut it down, or take it back to our founding principles and make the company what it had intended to be in the first place. I chose the third option. Doing so forced the question, how do I go about doing that? I knew consciousness came from the top, meaning I had to start with me.
So, I surrounded myself as best I could with a bunch of what I thought were successful business owners. I joined associations at the local and national levels. There is an organization here in Canada called "Entrepreneurs Organization". I joined it. I found myself a leadership coach, not a business coach. I knew that what I lacked was leadership skills. I didn't want somebody to tell me how to run the business. I wanted somebody holding a mirror to show me how I was showing up as a leader.
In 2017, we started that journey and have not looked back since it's been tumultuous. But I think the journey we began back then really helped us. The covid storm was much better than most businesses because we believe in this constant reinvention of ourselves, like asking ourselves, is this the best way to do things? I hate the idea of setting it and forgetting it.
That's a big part of what Thrillworks stands for. We like to ask ourselves hey, are we still operating with the best information possible? When was the last time we revisited that decision we made, that process we put in place? Has anything changed? Would we do the same if we had to make that choice today?
So, when Covid hit, and we were all forced to do business differently, Thrillworks was already in a constant state of evolution. We were able to weather that quite smoothly. Now, I think businesses everywhere had a really rough go. It's not to say that it was easy for us, but we certainly had almost an unfair advantage, and quite frankly, so did our customers because we brought that thinking to them. We ask them regularly if we can rethink a choice that we've made in the past. Is there a new technology that would allow us to do this better, cheaper, and faster for you? And so, our customers really love that because we don't wait around to be asked. It serves the business well simultaneously and attracts excellent talents because they get to exercise that talent.
Do you think the fact that you were so successful so quickly played a role in 2017, maybe the decisions you made or didn't make?
I absolutely think our early success was both a blessing and a curse. It was a blessing because we're still here. We had success, so I'm appreciative of that. But as a first-time business owner, the consequence is that you think you have it all figured out when you have early success. And that success is sustained for a period of time, and it was for 12 straight years; we couldn't lose. When we stuck to our values and pursued the mission I had in my head, we couldn't lose for trying.
I say that with a bunch of pride, but I also say that with humility at this point. Because once you think you have it all figured out, you stop practicing what Jim Collins calls “Productive Paranoia"; what if this could be better? Why is it that I'm having success? Where is success coming from? How am I creating value for my customers? How do I know if that's what they think? Go and ask them. But you stop doing those things if you think you have the answers figured out. And that's where we found ourselves in 2012. We stop asking ourselves what it is that's making us successful.
How did your company drift?
It drifted because I never shared the "raison d'être" outside my head. I just assumed and assuming anything is dangerous in business. I assume that people understood the driving motivations behind how I was making decisions at the project level for those first 12 years.
I assumed that when people were shoulder to shoulder with me or when they watched me interact with customers, it went unsaid how I was making those decisions. But it really doesn't. Even if it does, nothing can be gained by stating explicitly why a business exists. And ours, to put it simply, is to expose and exploit those overlooked digital opportunities that every business has and then capitalize on those opportunities for our customers.
Now, that sounds simple, but some things had to be in place. I alluded to this when discussing what I learned at the engineering firms. The first thing that I knew we always had to do, and I do this in all aspects of my life, is try to give a good listening to whoever I'm talking to before I start making recommendations. As Stephen Covey says, “Seek first to understand before you try to be understood.” Because once a person feels understood, it's oxygen to the soil. You can build trust, and with trust, somebody will allow you to lead them. With good listening and permission to lead, you can help somebody get to the solution they hope to get to, even if it means taking them in a direction they wouldn't have chosen naturally.
Much of what we have to do for our customers involves understanding what they want but helping them know what they need to do to get what they want. Because if they knew what they needed to get what they wanted, they wouldn't need us. So, we can't do that without first building trust. It seems like an odd thing for a business to say, and then possibly maybe an obvious thing for a business to say, but we're very intentional about how we go about trust building first, then giving them a good listening then offering to lead and then repeating that process, almost in a flywheel fashion over and over. Most of our business relationships last a dozen years or more, which is almost unheard of in the professional service field.
All good things we can do with our customers come from this ongoing process of trust building. It's not just a one-time occurrence. We don't just do that at the beginning of the relationship and then hope that our work does the talking for us. We must show up and try to understand where our customers are coming from daily. What do their customers need from them? What is the marketplace demanding of our customers' products? What do our customers value in us? And so, once we have figured that out, then you get permission to lead. With that leadership comes the responsibility of being proactive and accomplishing great things with your customer.
What entrepreneurship lessons have you learned in 24 years of running your business?
Lots. And I'll start with the importance of boundaries. I would work in the early days endless hours. I would try to make up for any shortcomings that happened with a staff member. Because I wasn't clear about what they needed. They would put in their best efforts. I wouldn't want to tell them if it was wrong, and I would make up the difference. As a result of that, it was very difficult for anybody working with me to get better because they never knew when they did something wrong.
When I started to enforce boundaries about like, I need you to get better at this, I can't do the work for you, it could seem, if taken out of context, just a pleasant way of delegating and making the delegator feel good about themselves. It really isn't. When you set boundaries like these are our values, we hire only on these values, and we fire based on these values. This is our vision. You need to believe in this vision, or you can't be part of the team.
Boundaries are actually the only way to create a healthy environment so people know how to score. For example, people know when they're out of bounds; without boundaries, it becomes almost impossible to scale a business. It will only move at the speed that the entrepreneur can move if you don't enforce those boundaries. So, that lesson has served me well, far beyond the entrepreneurial world. I'm the father of two grown children at this point. And boundaries were one of the healthiest practices we had inside the family.
I think it's translatable everywhere. Another thing I found is that the ability to rethink a choice is critical. As a small child, it appeared first, and I always wondered whether we could improve this. Is this the best way of doing something? Is there a better version that has emerged since the last time that we decided how to solve this problem? I've also adopted that thinking outside of the business and tried to coach all team members on it.
Lastly, I've really come to understand that it's my job to help grow other leaders inside the business; it's not enough to be a leader myself. Part of being a leader is coaching others to become leaders in their respect. Those lessons I couldn't learn early enough. I wish I had learned them earlier, in fact.
Now you need to find people who want to grow and be coached. But I think it's fundamental on our part not to get in the way of people's success by setting them up for failure, by not giving them clarity and the opportunity to succeed. Unfortunately, it took me a little too long to figure that out, but I think we're there now as a business. Our company has some fantastic leaders, and we can tell the difference; our growth demonstrates that.
What would be the one recommendation you would give to other founders?
Rethink. There's a great book called "Rethink", by the way. I think it was written by Adam Grant that touches on this and goes a bit deeper on that matter. If there was one thing, if I had one wish and I could go back in time, I think the thing that I would probably do is make sure that my vision was very clearly stated, so clearly that anybody inside the organization could repeat it.
I think doing so immediately repels the wrong employees and the wrong customers, and it attracts the right employees and the right customers. It's not a silver bullet, but the starting point to getting everything right. Attracting A players is fundamental, but much of this depends on having the right vision if you want to attract the right people.
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