FULLY CORRECTED TRANSCRIPT
PETER BOOLKAH — 00:10
Hi, Peter Boolkah here, and welcome to today’s edition of The Transition Guy.
Joining me in the studio today is Trivelle Simpson, who is the founder and CEO of The Drive Group. Welcome to the show, Trivelle.
TRIVELLE SIMPSON — 00:23
Thank you so much for having me, Peter. I appreciate it.
PETER BOOLKAH — 00:25
Trivelle, what is The Drive Group, and why does it exist?
TRIVELLE SIMPSON — 00:31
The Drive Group started out as a think tank.
My initial step into entrepreneurship was actually in financial markets, studying derivatives trading. Coming out of school, I was a political science major, so we took a view of politics, how it affected the economy, and then made financial decisions based on that.
That’s how The Drive Group started. It was a small group of people trying to make financial decisions based on political subtext globally.
PETER BOOLKAH — 01:04
It must be interesting for you right now, then.
TRIVELLE SIMPSON — 01:10
Yes. I tell everyone that the greatest credit I give to my team is that we’ve traded through a lot.
The business was founded in 2016, so it has been a fun ride. We’ve gone through Brexit, we’ve gone through a Donald Trump presidency, we’ve gone through COVID, and we’re still open. There’s something about us. At least we try to keep our market assumptions tight.
In terms of bolstering that position, it led to us making investments in real estate because diversification is always important.
It also led to us wanting to fund good, smart ideas. That was partly motivated by my time as head of operations at a technology startup. I realised there was a need for funding, but the process of receiving funding always felt so esoteric when I was sitting in that chair.
We created a venture arm that we felt was more direct. If you have a good idea, send us an email. We’ll make sure it’s reviewed, and we’ll double down on it if we believe it can create value.
PETER BOOLKAH — 02:14
VC funding is an important part of the journey, especially for startups that want to scale.
From my experience of becoming involved much later, whether at Series B or during a third round of funding, very often the founders have potentially screwed up the business. They’ve given away the majority of it, the VC funders have lost money on the investment, and it doesn’t work.
You’re going down this funding route, which I agree is needed. Have you managed to circumvent the screw-ups that typically happen when VC funding comes into play without the right level of support?
TRIVELLE SIMPSON — 03:25
I’d like to think we have a system in place that will avoid that, but you’ll know from experience that it will be years before we determine how it goes. If you’ve picked a horse, you keep betting on that horse. We’re still optimistic about all our positions.
I like to think that I look at VC funding from the position of a founder. I wasn’t a founder at the previous company; I was an intrapreneur. But I bled that blood and shed those tears.
I knew what it was to go into a room with your heart and soul, pitch a product and hope that somebody resonates with it. I know that passion.
Unfortunately, there are terrible stories in VC funding. You have Elizabeth Holmes and Theranos. The day before her pitch, she fakes the machine.
It’s strange because I’ve been in a room, and I remember that moment when the meeting is tomorrow and you’re not ready. What are you going to do?
I think of Bill Gurley and Travis Kalanick. Bill was an early investor in Uber. The story says that when Travis met Bill, he was nervous and shaking. He bought off all the taxis around the restaurant so Bill would be forced to call an Uber at the end of the meeting. This was a guy he wanted to impress.
Years later, when they wanted Travis Kalanick out, he said, “I’ll walk, but you’ve got to get Bill Gurley off the board.” He ended up hating the guy.
I try to look at these stories as cautionary tales. It’s a razor’s edge.
The core concept for any venture investment is that you’ve got to trust your founder. You have to like the founder more than you like the idea. That’s my policy.
If you like the idea but don’t like the person driving it, there’s no point because, at the end of the day, it isn’t your idea.
You’ve got to like the founder more than the idea. If you do that, I think you have a greater likelihood of success.
Bill Gurley was removed from the Uber board, but Bill Gurley was paid to be there. It wasn’t a bad investment; it was a bad relationship. When people asked Bill about it, he said he thought Travis was a genius.
That’s the perspective from which I try to read it.
PETER BOOLKAH — 05:47
That’s interesting.
In the UK, we have an entrepreneur called Steven Bartlett. I caught him in an interview recently, and he said that during his first series on Dragons’ Den, the big mistake he made was backing the idea. By the second series, he was backing the horse.
It’s great to back the horse, but I think the step missing from a lot of VC funding is backing the horse and then putting the support in place.
The person with the great idea doesn’t necessarily have the experience required to run the business and build the organisation. If we have the great idea and the support structure in place to mentor them—and I don’t mean mentoring from afar—we can train that person to become the CEO, executive or entrepreneur the business needs.
I think many businesses that gain access to funding would then be far more successful, and the failure rate would diminish drastically.
TRIVELLE SIMPSON — 06:58
I agree wholeheartedly.
I think you even saw that with Meta. People ask why Facebook made such an issue of the metaverse and how it happened.
I’ll give your audience some homework. Look at who the business head of Facebook was, when she left, and what happened with the metaverse.
There was one woman driving Facebook’s decisions when it was one of the fastest and strongest current companies. It wasn’t Zuckerberg.
Zuckerberg is a genius, but it took somebody else to navigate that business. I don’t think there’s anything wrong with that.
PETER BOOLKAH — 07:26
No, I agree.
How important is having a varied résumé when it comes to overcoming the diverse challenges we face in business?
TRIVELLE SIMPSON — 07:43
I think it depends on where you sit.
I was at a dinner the other day with different kinds of people. All were presumed to be mildly successful; that was why they were invited.
What was interesting was that I could see the difference between people who worked for Google and earned a high salary and the people who had to go and kill their own animal or bake their own bread, as they say. That is what the entrepreneur is seeking to do.
The secret was charisma.
The entrepreneurs were always selling. You felt they could walk into any room, as though they had been there for years, and make you feel like their best friend. It was charisma.
To that end, I think the greatest tool any entrepreneur should understand is that it doesn’t necessarily matter what you did. What matters is how much charisma you left with.
Charisma is what drives you. Charisma is what gets you the funding. Charisma is what enables you to build a startup.
When you think about a startup, you’re underpaying and overworking people in pursuit of a vision. You don’t get that out of people without charisma. You have to be a charismatic leader.
I grew up in church, and I think about pastors. I used to volunteer for hours for nothing, but you became swept up in the concept. I like to think entrepreneurship can work in the same way.
What is your different path? What is your different history?
I was a political science major. I worked at a bank, spent some time in the arts, and ended up in finance. There’s nothing linear about that story.
However, during every iteration and every step I took, I needed charisma to make it to the next step. That was the muscle I was developing from strength to strength.
PETER BOOLKAH — 09:36
You’ve talked about startups several times. Why do you think you gravitate towards them?
TRIVELLE SIMPSON — 09:46
This is going to sound strange, and hopefully I don’t lose any of your audience when I say it.
I’m Canadian.
PETER BOOLKAH
Sorry, that won’t lose the audience. You’re fine.
TRIVELLE SIMPSON
Canada is large in land mass but small in population.
I didn’t grow up thinking I could work for Wells Fargo, Citibank or Google. They didn’t have head offices where I grew up.
If you came from where I came from and wanted to leave a mark, you had to build that company.
When I was a kid looking for examples, I looked at the people who made something in their garage. I looked at the people who developed an idea with their close friends and then took it global.
I think that resonated with me because it was the vision I could see from where I lived.
I did go to school and achieve my degree. There was a linear path, and I tried to give myself at least a parachute.
But when I thought about throwing punches and entering the arena with the greats, I didn’t think about becoming the CTO of YouTube or the next person in line at Google.
I thought about building a company that could enter the ring with the people I idolised and studied.
PETER BOOLKAH — 11:14
That’s probably quite different from living in a major city, where people may be more predisposed to pursuing a corporate career.
In the UK, everybody aspires to work for a corporate organisation. Large corporations make up only about 10% of the economy, yet probably receive 90% of the press. It’s quite bonkers when you think about it.
TRIVELLE SIMPSON
It’s a perception, right?
PETER BOOLKAH
There is a perception and a misconception at the same time.
TRIVELLE SIMPSON — 11:47
It’s the same argument with Manchester City. Manchester City is the huge club, but you’ve never met a Manchester City fan outside the Etihad, right?
PETER BOOLKAH — 11:56
You see, now we’re moving towards politics. It’s starting to get dangerous.
TRIVELLE SIMPSON — 12:02
I’m just bugging you.
PETER BOOLKAH — 12:03
Pep is a good example of a great leader. He is probably one of the best people managers in sport across the globe.
TRIVELLE SIMPSON — 12:12
I think the thing that marks Pep is his willingness to make a drastic decision and live with it. He doesn’t dilly-dally and he doesn’t waver.
When he was at Barcelona, he decided he didn’t want to play with Samuel Eto’o anymore. Eto’o was still firing on all cylinders, but Pep said, “No, not him.”
Many times, he has made decisions and simply been willing to live with them. It’s his call.
PETER BOOLKAH — 12:34
But isn’t that what you have to do as an entrepreneur?
The successful ones make decisions. The businesses that die are the ones whose leaders fail to make decisions.
TRIVELLE SIMPSON — 12:46
It’s a balance.
Using the football-management example, you can’t lose the dressing room. There are certain decisions you can’t make, but you also need sensitivity around the decisions you can make.
I think about Pep making his strong decision concerning João Cancelo. That was difficult because Cancelo was a leader in the dressing room.
Notwithstanding what will happen in the league, I think that was a masterstroke of leadership because it did something to the dressing room. Pep almost lost it in order to gain it back.
That’s what leadership and entrepreneurship are. You have to know when the tide is in your favour and when to make a drastic decision.
PETER BOOLKAH — 13:32
You grew up outside a major city and saw starting a company as the way forward.
When you started the current Drive Group and it came to your first hires, what approach did you take, and why?
TRIVELLE SIMPSON — 13:56
I love telling this story.
I grew up in a town called Brampton, outside Toronto. Toronto is our major city, and Brampton is about 45 minutes away.
My father had been in supervision throughout his working career. He was a production supervisor.
He taught me from when I was a kid that you pick your C-suite for loyalty and your workers for competency.
My first hire was my best friend because I knew I could trust him. It was as simple as that.
If something happened to me, it would be up to him. It had to be somebody I trusted deeply.
As you move further out, you make hires based on somebody being smart, wise or able to bring something different to the table.
But I’m a firm believer that your first hire should be somebody to whom you would give your wallet or somebody you would want beside you in a street fight.
I believe in that. Your C-suite has to be loyal, your executive team has to be skilled, and from there you build your business.
That’s my personal viewpoint.
PETER BOOLKAH — 15:03
That’s interesting. What advice would you give somebody who doesn’t believe they have those people available to them?
TRIVELLE SIMPSON — 15:11
My advice would almost be a pushback: you do have them, and I’ll tell you why.
There are three Ts. You’re either training, tolerating or terminating. You’re always doing one of those three things in leadership.
When you choose your best friend or closest friend, you also have to make a deal with yourself that you’re going to train them.
I’m not talking about whether they are already good at the job or naturally competent. They have to believe in you.
You’re the one with the vision and the plan. That first hire has to help you execute your vision. They have to be able to follow instructions.
That means you must be willing to train. You must be willing to train and tolerate.
If you can manage those two things, that person is in your circle.
You have people who are loyal to you, whether you recognise them or not. Nobody gets anywhere alone. If you want to go fast, go alone. If you want to go far, go together.
That person is there.
What people sometimes don’t accept is that the trade-off means training and tolerating a great deal during the early stages because the person didn’t begin with natural competency.
That’s okay. You’ll eventually reach a point where you make an inverse decision, but those early sacrifices are important.
PETER BOOLKAH — 16:27
You hired your best friend. How did that crucial first hire affect your startup’s growth trajectory?
TRIVELLE SIMPSON — 16:41
I was fortunate that my best friend was the opposite of me.
I consider myself more political and agreeable. I considered him more of a hammer—a little rougher.
The greatest impact came from a decision about client acquisition. There was a particular class of client I didn’t want to take on.
I was worried about the additional drama and the headache of managing those people. Because I’m political, when I think about onboarding clients, I’m thinking about how we manage all their expectations.
He was thinking about the bottom line. His response was, “There’s revenue here. Let’s do it.”
That hire grew us by 500% because he forced me to pursue a vertical I wouldn’t naturally have entered.
We had built our business around individual retail clients. He came to me and said there was a corporate opportunity. We could move into B2B management, take on entire companies and become their financial-consulting solution.
I thought it was one thing to work with a household, but another thing to work with a business that would squeeze me to produce the highest possible return whenever it experienced a bad month.
He was confident we would be successful and that we would develop the aptitude to handle the difficult conversations.
That was his greatest contribution: growing the business by moving into a vertical I wouldn’t have pursued naturally.
PETER BOOLKAH — 18:24
That’s an amazing story.
What qualities do you look for in potential candidates when you’re building a startup team?
TRIVELLE SIMPSON — 18:40
I personally like entrepreneurs, so I like people who have wanted to start their own business.
Hopefully this doesn’t sound indelicate, but I think there’s value in an entrepreneur.
What is an entrepreneur? It’s somebody willing to work as though the business were their own, put in the late hours and proudly wear the brand on their chest—but they’re not going to give you a penny because their bread has to be buttered as well.
I used to ask a question in every interview: “If money wasn’t a factor, what would you do? What business would you start?”
Every candidate who answered with something I knew we could create under our company umbrella was hired because I realised I had unlocked something.
My father also told me that your business will grow if people are helping to fulfil your dreams while pursuing their own.
I might ask, “What would you do if money wasn’t a factor?”
Somebody might say, “I’d be a video editor.”
In my mind, I’m already thinking that we’ll run a media component within the company. We’ll produce videos and social-media content, and that person will be in charge.
In an indirect way, they are running their own business and pursuing that dream. They’re simply doing it under our banner, and now we’re all happy.
I like entrepreneurs. I love them because they’ll work long hours, develop critical ideas, find ways to pivot and think about mitigating expenses—which is crucial during a startup.
They understand that everybody has to reach the finish line. It isn’t only about receiving a cheque. Subconsciously, it’s also about fulfilling a dream they may not have been able to pursue previously.
PETER BOOLKAH — 20:32
That’s interesting.
Of all the personality-profiling tools I’ve encountered over the years, I’ve never found one that measures entrepreneurship.
TRIVELLE SIMPSON — 20:46
It has worked for me with every single person.
The trade-off is that the moment you stop rewarding that entrepreneurial component, they will leave.
But if you can hit it dead-on, they’re not leaving. They’ll become kings and queens among the masses.
PETER BOOLKAH — 21:10
You raise an interesting point. If you don’t satisfy their needs, they’ll leave.
TRIVELLE SIMPSON — 21:17
Yes.
PETER BOOLKAH — 21:19
Therefore, in your opinion, what are the essential qualities of a great leader within a startup environment?
TRIVELLE SIMPSON — 21:27
It’s important to understand your core competency and not overstep.
Because I like entrepreneurs, I have waived the right to micromanage. They need to feel that what they’re doing is their business. That’s the trade-off, and I can’t break that rule.
The moment I break it, they’ll feel micromanaged. Then they’ll feel that the entrepreneurial lifestyle isn’t giving them what they want.
They’ll start thinking, “I could earn more money without experiencing as much stress.” Then they’ll think, “This isn’t even my company,” and walk out the door.
It’s about understanding what political science calls the social contract. There are rights and freedoms you waive in exchange for something.
You can pursue your core desire freely, perhaps with only monthly or weekly check-ins and minimal input from me.
I say it all the time: “I’m merely here to point us in a direction. You’re there to determine how we get there.”
Even if I don’t completely understand what somebody is doing, I put them in that position because it’s their child.
For me, it is that simple. I cannot micromanage my people. Doing so would create an environment in which they felt betrayed by the culture that was sold to them during the initial interview.
PETER BOOLKAH — 23:03
Going back to Pep, when he took over Manchester City, it was almost like another startup. It was a startup team.
What’s interesting is that, throughout his time there, very few people have chosen to leave him. There’s a lesson to be learned from that leadership.
When most football managers take over a club, the existing team usually doesn’t survive anyway.
TRIVELLE SIMPSON
Correct.
PETER BOOLKAH
They have their own ideas about how they want to build the team.
That applies across sports. When you look at sports teams, they’re effectively the equivalent of startups.
TRIVELLE SIMPSON — 23:56
That’s why I love them.
My favourite managers are the ones who can enter an organisation, galvanise the troops and move them towards one singular goal.
Sometimes people will even play for a person they don’t particularly like if they believe that person is a genius.
I think about Steve Jobs. People say that Steve had an idea every 30 seconds, but he was a jerk.
People marvel at somebody who can generate an idea every ten seconds, though, so they’ll follow that person.
PETER BOOLKAH — 24:29
The teams that worked well under Steve Jobs didn’t think he was a jerk.
TRIVELLE SIMPSON — 24:34
Very true.
PETER BOOLKAH — 24:35
That’s the interesting thing. They were his teams.
The people who didn’t enjoy the culture or atmosphere—and perhaps weren’t A players within the organisation—thought he was a jerk.
But it makes you wonder who the jerks really were. It’s something to consider.
You’ve worked in startup environments. Have there been occasions when your leadership skills were put to the test? More importantly, how did you navigate those situations?
TRIVELLE SIMPSON — 25:13
That’s a good question. There are a couple of stories I could tell, but one in particular stands out.
We were working in cryptocurrency at the time. There was a young guy who had come from a bank, and he was a genius when it came to understanding the emerging-technology space.
I’ll say this as a nugget so he knows I’m talking about him.
We were in the office in January 2020 when he looked up and said, “Guys, this is a serious problem. The world is going to shut down in two months.”
He called COVID exactly.
The guy is a genius. His brain operates at a level I still marvel at. I think about him in an almost mystical way.
But he was immature and struggled with focus.
To get the best out of him, I had to empower him. I would tell him, “You’re like a boxer in one of those Rocky films. You’re the best ever. Nobody can touch you.”
You let him go, but you also have to rein him in because you have to teach him maturity and give him additional skills.
One day, we were in the office. We had probably spent two weeks telling him, “You’re the king of this realm.”
He had taken his trousers off and left them lying around. It was still an office, for goodness’ sake.
I walked in and said, “Whose trousers are these? Why do you have your trousers off? Are you simply going to leave them hanging around the office?”
When I said that, I thought he would grab them, apologise and put them away.
Instead, he challenged me.
I realised it was because he was thinking, “I’m a genius. I’m the best ever.”
It became a back-and-forth exchange. The office wasn’t that big, so people began gathering around us.
I realised that I had to win that exchange or risk losing the team forever. I had to make an example of him, but he was also my best person. He was a genius, and that made it difficult.
I sent him home. I said, “Go home.”
After he left, I brought everybody together and said, “I’m sorry you had to see that, but nobody is more important than the company. You all know I think he’s a genius.”
Everybody nodded and agreed, and then they returned to work.
When he came back the following day, I had a conversation with him.
The key to that team meeting was anticipating what would happen. Everybody would finish work and call him. He would ask, “What did Trivelle say after I left?”
Everybody could reinforce the same message: “He said you’re a genius, but he still had to send you home.”
He understood. I hadn’t undercut what I had been telling him, and I didn’t lose either the individual or the team.
I always remember that one. The guy had his trousers off, so he had to go. But he was my best person, so what do you do?
PETER BOOLKAH — 28:22
I’ve never heard that one before.
You started the business in 2016 and went through the startup phase. How have you continued evolving your leadership style to meet the changing needs of the business and team?
TRIVELLE SIMPSON — 28:38
My greatest gift to The Drive Group came when I accepted the challenge, in 2017, of becoming head of operations for another business—a technology company.
Doing those two things simultaneously was the greatest gift of all.
I worked under somebody else. I was the number two, which was an incredible ego check.
You realise there’s no such thing as hierarchy; there are only roles within a business. We all serve different purposes.
It was a different vertical. I was working at a technology startup involved in fundraising, but I wasn’t in the funding position.
The key lesson was that a good leader wears many hats. A good leader must be capable of wearing many hats—or, at least, that was what I took from the experience.
I always wanted my team to see me in the mud with them.
If we’re working late, I’m staying. Even if what we’re doing is nowhere near my skill level, I’m there.
If we’re in a virtual environment and you call me, I’m available. I don’t care whether I’m out for dinner. I won’t answer and say, “I’m out for dinner.” I’ll step outside and ask, “What is it?”
We’re in the trenches together. The team knows you’ll bleed with them.
But you shouldn’t overglorify your own struggle.
If you’re working late, don’t tell anybody. They’ll see it. If you’re pulling something off, don’t tell anybody. They’ll see it.
When you appear after a week with a miraculous new client or a new revenue stream, they’ll subconsciously think, “This person has been working the whole time and has been there in my corner. I’ll fight for this person.”
Working in those two businesses simultaneously was the greatest gift of my life.
PETER BOOLKAH — 30:27
Awesome. Our time has come to an end.
If people want to connect with you or follow you, what do they need to do?
TRIVELLE SIMPSON — 30:37
As people can probably tell, I’m company-first and brand-first.
If you want to follow me, follow the company. It’s @thedrivegroupinc on Instagram.
If you want to look at our wider content online, visit www.thedrivegroup.ca.
You’ll find links to our YouTube channel, where we have long-form business content looking at subjects such as the debt ceiling, changes in politics, and shifts in markets and the economy.
Our Instagram is fantastic. You’ll find shorter portions of that content, plus information about our Drive 250 competition, where we give an entrepreneur an opportunity to receive a quarter of a million dollars.
We’re proud of both those things, and that’s where I direct people.
PETER BOOLKAH — 31:31
Awesome. Thank you very much, Trivelle.
If you’ve enjoyed today’s episode and think other people could benefit from it, please like it. We enjoy receiving likes, it helps us with the algorithm, and it helps other people discover our content.
Share it with other people so they can benefit too, and remember to subscribe so you don’t miss future episodes. You don’t want to miss another guest like Trivelle—not that there will ever be another one quite like him.
If there’s anything you want to explore more deeply, head over to Boolkah.com and get in touch.
Trivelle, thank you so much. It has been amazing, and you’ve been a great guest.
Remember: failing to learn is learning to fail.
