The Secret Sauce of Successful Ventures

In this inspiring episode of the Service-Based Business Society Podcast, we sit down with Trivelle Simpson, a visionary entrepreneur and venture capitalist who is reshaping the landscape of Canadian business. Trivelle shares his journey from the structured world of corporate Canada to the dynamic realm of entrepreneurship, offering a candid look at the highs and lows that come with leaving a secure job to pursue a dream.

Trivelle delves into the importance of supporting underserved markets, particularly emphasizing the potential of Canadian entrepreneurship and the power of investing in female-led businesses. He discusses the multi-billion-dollar opportunities awaiting female entrepreneurs and the societal shifts necessary to harness this untapped potential.

With a blend of personal anecdotes and professional insights, Trivelle also touches on the transformative power of risk-taking. He challenges listeners to embrace fearlessness, drawing on the wisdom that the happiest days in business can indeed eclipse the toughest ones. His message is clear: true success comes from believing in your vision and having the courage to leap towards it, even when the safety net is not in sight.

Join us as we explore Trivelle's innovative approach to venture capitalism, where every investment is a step towards building a more transparent and accessible future for entrepreneurs. From the importance of visualizing success to the strategic delegation of tasks, this episode is packed with actionable advice for anyone looking to make their entrepreneurial mark.

Whether you're a seasoned business owner or just starting, "The Secret Sauce of Successful Ventures" is an episode that will leave you motivated to turn your business aspirations into reality. Tune in to discover how to lead with conviction, build a culture of community, and why sometimes, the best move is to cancel that meeting and just get to work.

About the Guest

Trivelle started The Drive Group in 2016 from a tax return and has since grown it into a multi million dollar company. His history of working in start up environments of many forms across varying industries helped him to develop the skill of identifying smart risks, knowing when to step back and when to push forward. After several years working for large organizations such as Davis + Henderson, The Royal Bank of Canada, Genworth, Manulife, and as the Chief Operating Officer for Chelle Service Capital, Trivelle was inspired to start a company that focused on trends and analysis to help businesses achieve consistent cash flow.

Connect with Trivelle:

Facebook: The DRIVE Group

Instagram: @thedrivegroup
Website: thedrivegroup.ca

About The Host

Tiffany-Ann is the epitome of a modern-day superwoman. Juggling the roles of a devoted mother to three, a dynamic agency leader, and a sharp business strategist, she seamlessly blends her responsibilities, making multitasking look effortless. Her journey in the business world is marked by her innovative strategies and a keen understanding of technology, setting her apart as a trailblazer in her field.

Connect with Tiffany-Ann:

YouTube: Bottcher Business Management Agency
Tiktok: @ta_bottcher
Website: bottcher.io
Facebook: @bottcher.io

Creators & Guests

Host

Tiffany-Ann Bottcher

Entrepreneur | Founder, Bottcher Group | Host, Service Based Business Society Podcast | Author, Data Driven Method | Helping you scale your success!

What is Service Based Business Society Podcast?

Attention entrepreneurs! Are you looking for ways to scale your service-based business without sacrificing your sleep? Look no further than The Service Based Business Society Podcast, hosted by Tiffany-Ann Bottcher.

Each week, Tiffany-Ann shares valuable insights on productivity, business strategies, marketing trends, and tech secrets that you need to know in order to take your business to the next level. She firmly believes that a successful service-based business must prioritize an amazing client experience and sustainable, predictable, repeatable profit, and she'll teach you how to do just that.

But that's not all - Tiffany-Ann also invites expert guests to share their knowledge and experience with you, providing even more valuable insights on service-based business growth and sustainability. You won't want to miss a single episode!

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MINDSET
Focused on helping entrepreneurs cultivate the right mindset for success in their businesses. Hosted by experts in the field, the podcast covers a range of topics related to mindset and business, including self-improvement, goal setting, visualization, and meditation. The podcast provides practical tools and strategies to help listeners develop a growth mindset, overcome limiting beliefs, and build confidence. Through inspiring interviews with successful entrepreneurs and thought leaders, the podcast shows that a positive and resilient mindset is key to achieving business success.

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Dedicated to equipping business leaders with the knowledge and skills they need to lead with confidence, based on data-driven insights. Hosted by experts in business leadership, the podcast covers a range of topics related to data analysis and interpretation, strategic decision-making, and effective communication. It provides practical tools and strategies for interpreting complex data sets and using them to make informed business decisions that drive growth and success. Through engaging interviews with successful business leaders and industry experts, the podcast offers valuable insights and examples of how to use data to build strong teams and drive innovation.

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A great resource for aspiring entrepreneurs looking to learn from the experiences of successful business owners. Through relatable and engaging entrepreneurship stories, the podcast provides valuable insights into the challenges and opportunities that come with starting and running a business. Hosted by experienced entrepreneurs, the podcast covers a range of topics related to entrepreneurship, including idea generation, product development, marketing, and fundraising. Each episode features inspiring interviews with successful entrepreneurs, who share their personal stories and provide practical advice and tips for those looking to start and grow their own businesses.

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Brought to you by Bottcher Group of Companies

Tiffany-Ann Bottcher:
All right, Trivelle, welcome to the show. It's great to have you here.

Trivelle Simpson:
Thank you so much for having me. Appreciate it, Tiffany.

Tiffany-Ann Bottcher:
Nice to have a fellow Canadian on the podcast. Spend a lot of time talking cross-border. We serve both sides of the border. How about you guys? Are you mostly focused on those Canadian clients, American clients as well? What's your audience?

Trivelle Simpson:
So because of the nature of what we're in, especially during COVID with essentially all of North America looking for alternative investment options, people were looking for consultation. They were looking to understand alternative markets. So we saw ourselves really having a more of a North American presence, right? We're dealing with the same interest rates, essentially the same fallout from political decisions. And because our specialty isn't sort of reading the market, so the traditional investor looks at risk, we look at the market as a whole. So we find ourselves.

Tiffany-Ann Bottcher:
Thanks for watching!

Trivelle Simpson:
going back across the border all the time. Fun fact, my accountant, just as a point of reference, so I always make sure I see the country, is based out in Vancouver. So I make the flight out west as often as I can.

Tiffany-Ann Bottcher:
Amazing. Well, that's a word on this side, on this side of the country. It's beautiful. Although we have had over summer, some crazy fires. And I feel like just all over North America though, between Hawaii and tornadoes and hurricanes and just crazy, the world is a crazy place. So let's dive in. Let's chat a little bit about what you do specifically. You talked about kind of reading the market versus the risk. Let's dive in. What does that mean? Tell us more.

Trivelle Simpson:
Yep.

Trivelle Simpson:
Yeah, so obviously my name is Trayvon Simpson. I'm the president and founder of The Drive Group. The Drive Group operates as a trading markets think tank and sort of incubator. So we provide consultation on market moves and risk assessments. From there, we spun out our retained capital to doing venture investments. So we like to accelerate businesses or help businesses get their startup capital as well as real estate development because we sort of want to understand a bit more of the brick and mortar space. Recently this past year, we also are trying to put our hands a bit into media.

Tiffany-Ann Bottcher:
you

Trivelle Simpson:
We spun out a sort of a new company called Spoke Podcast Network. And in Spoke, we're looking to sort of have a hub of a vast amount of different informational content. So we want to make the real crux behind it is we want to make voter turnout in Canada be a lot better. So we want political content that's sort of easily accessible. We break down world events in these short sort of 10 minute vignettes.

And then just for fun, we have sort of editorialized podcasts where we allow our talent to sort of just be themselves with pop culture events. The concept is you catch them with honey and then you retain them with that informational content. And we're hoping to be able to go from strength to strength, uh, as we get ready to gear up really strongly with that in 2024.

Tiffany-Ann Bottcher:
So, you know, it's interesting and we're going to dive into this political content piece of it because I think that it applies to those who, like yourself, are taking a stand on something incredibly important. Left wing, right wing, Canada, US, you know.

Trivelle Simpson:
Mm-hmm.

Tiffany-Ann Bottcher:
The fact is that people need to show up and have an outcome. You know, somebody said something a long time ago to me, you know, I remember years and years ago, I was like 10 years old and I rode horses really competitively and we had like a kids council of the Pony Club. Bear with me, there's a reason. And one of the things they instilled in us at that time was, you can't complain if you don't help.

Trivelle Simpson:
Mm-hmm.

Tiffany-Ann Bottcher:
And so, because you get people who'd be like, oh, why didn't we do a pizza party? Or why didn't we do this? And so right from 10 years old, there was this piece that was like, hey, like if you're gonna complain about the government, about the pizza party or lack thereof, like are you contributing in the solution? So obviously, you know, a very important topic globally is showing up and taking a stand. But from a business owner perspective,

that can be a scary place to put yourself online, to be able to go out, put your opinions out there. And so whether that's, you know, and a lot of people who say like, I would never put something political out there online, but maybe it's a new business, and maybe it's someone that's like, hey, I don't know what my aunt's gonna think, or you know what my old boss is gonna think, or yeah, as soon as you put yourself out there in any way with something that's not black and white in terms of, you know.

political views, new business, whatever, it can be a little frightening. So how does that, I mean, that's a big step for you, you know, political content. So walk me through the mindset shift that allows you to do that and feel like it's the right thing for your business.

Trivelle Simpson:
Yeah, well, for me, my initial vacation is my degree. I went to, I always say the, because I love how in the States they say like, I went to the University of Texas, right? So I went to the York University in Ontario. And I was fortunate to capture a political science degree. My time was spent there. I thought I was gonna be a campaign manager. But at the same time that I was at school, I played football for a couple of years in college.

Tiffany-Ann Bottcher:
Love it.

Trivelle Simpson:
Then I had an opportunity to be a sort of a bilingual risk analyst for Millennium One Solutions. So I was kind of doing both things in the tail end of my college career, graduated and volunteered for a couple campaigns for people who I thought would win. They didn't win. So then I was jobless and at that time I committed to my sort of risk management career, which kind of going from level to level brings me into finance, but I don't think that the

Tiffany-Ann Bottcher:
Beep, beep, beep.

Tiffany-Ann Bottcher:
Thanks for watching!

Trivelle Simpson:
There's something about the love of politics that I discovered in those years, in those classrooms, that I felt people didn't understand. And as I got older, and I'm looking at my contemporaries, just as a point of reference, I have a college graduate teammate of mine, I played football with him, now a football coach. So this is not only a man, but a man leading young men. And I've asked him, I'm in my early thirties, he's also in his early thirties, he has a child. I said, have you ever voted? He said, no. And for me,

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
If we're not capturing the vote of the university educated, college educated, professional career parents of our society, then we're letting a lot go through the cracks. Now this isn't to criticize it, but then it was about spending time. Why don't you vote? What is it that you don't think? What is it that you do understand? What is it you don't understand? And realizing how esoteric a lot of these things were to the common person who didn't study it, I thought it was a civic duty. Let's enter this space.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
You know, we try as hard, you know, it's funny. Members on my team sit on all sides, right? So as a, as a, as a decision, we try and stay as centralist, centrist as possible. We're making commentary. What we're doing is we're trying to present facts in digestible bites so that you can understand what's going on. And we're doing that both in Canada and the U S so for example, something I'm very proud of is we had a conversation about the debt ceiling. There was a debt. It was a huge issue in the United States of America. They brought the debt ceiling.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
If it was a game of Russian roulette, they're on the last bullet in overtime. And the idea that, you know, especially in how sensitive our society is now, we got razor close to just breaking the world. That's what the debt ceiling is. It's, it's having a credit card bill that's maxed out and you go and say, Hey, can I get a credit limit increase? Or I can't pay for my house, my heating, my, and the, and, and Congress come back and says, okay, I'll give you a credit limit increase, but you gotta give me this, and then you say, well, I'm not gonna give you that. And then you guys just play that song and dance.

Tiffany-Ann Bottcher:
Mm-hmm. Yes.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
right up to its natural conclusion. And now the bills still have to get paid, but we're not, you know, and we're both saying, we're essentially both assuming that one of us won't let the other break the economy. And as time has gone on, we've gotten danger close to that. So we're very happy to release content even about that. So the decision, I think, was more based off of, let's not do this for revenue. Let's not even do this to outlay our political agenda.

Tiffany-Ann Bottcher:
Hmm.

Trivelle Simpson:
But let's do this so that more people just want to get out to the polls the next time they hear an election, because what's become the case, you know, sometimes you think of single issue elections, you know, election about COVID, election about health care, election about marijuana. But what we want is we want to change people thinking that they're betting an issue. You really want to bet your leaders. You want to bet your concerns. You want to bet your futures. And we just want to...

Tiffany-Ann Bottcher:
Hmm

Tiffany-Ann Bottche:
Mm-hmm.

Trivelle Simpson:
feel like people have the ammunition to feel comfortable to enter into that space.

Tiffany-Ann Bottcher:
I think a lot of people get to the point where there's almost an overwhelm and whether that is a, you know, we on, you know, our agency, we really focus on data and metrics and making confident decisions because I think oftentimes whether it's, you know, voting or a business decision or whatever, sometimes people are like,

I don't know what the right decision is, and then their decision is no decision. I don't know, so I'm not doing anything. And so I think that when it comes to the election in particular, people might say, well, I don't like choice number one, and I don't like choice number two, so I'm not making a choice, and I'm out. And so what would you say to those people? Because in my social circle, I argue this.

Trivelle Simpson:
Mm-hmm.

Tiffany-Ann Bottcher:
I'm the one who posts the picture of the women that fought for the right to vote every year that says, hey, get out there and vote because people did big things to make this happen for you. And so what would you say to those people that say, I don't know. I don't know what to do, so I did nothing.

Trivelle Simpson:
Yep.

Trivelle Simpson:
You know, to that I'll both give a commentary, but I also want to give an answer. I mean, I come from it from a different perspective. My parents came here as immigrants, which is the result of political policy, right? We, you know, my lineage starts because my grandma chooses to come here and then sends for her children. My father, the same thing. So this was a choice. This wasn't an accident. We wanted this, especially Canada over the US in our...

Tiffany-Ann Bottcher:
Right.

Trivelle Simpson:
in our circles is a conversation. The scary thing is not many of them vote and they chose to come here. The commentary I would say is you have insurance, whether you see the need for it or not, you do it because you know it's what you need to do in this country. You pay your mortgage if you have a home or your rent because you know if you don't, somebody's gonna call you. It's kind of what you gotta do in this country.

Tiffany-Ann Bottcher:
Great.

Tiffany-Ann Bottcher:
Right.

Trivelle Simpson:
I think of the model in Australia. Now, I do think that we can do a better job of it from a, from a legislative level, but in Australia, they have voter turnout close to a hundred percent. And it's a national holiday. What I try and, what I try and encourage people is that the same spirit that gave us universal healthcare, which is, I have a personal belief that we're lucky we have it because if we had to vote on universal healthcare today, I don't think we'd get it, but the same spirit that gave us that should be the same spirit that causes us all to vote. It is.

privilege as a response to where we live. You think of Canada as a country, we don't have neighbors that are violent to the south. There are parts in the world where that's not the case. We have one of the most accepted passports in the world. There are parts in the world where that is not the case. We have a GDP per capita above $52,000. We can do better, but there's a lot of places in the world where that is not the case. We have

vast amounts of unused landmass, right, that we can go explore. There's opportunity here for the brave. Many places in the world, that is not the case. And what drives our ability to achieve and receive and accept all these things is pressure on our representatives, pressure on our politicians. One statistic, it's been true since I was in middle school. If every person who didn't vote did vote and picked one candidate, the candidate would win by almost 20 points. That's how many people are sitting on the sidelines.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
It is enough to change the country. Now, you know, again, political scientists, I have my own opinions on first past the post, right? As I really believe in election reform, but before I could make that argument, we gotta show up. Before I make that argument, we have to show up and that has to mean something. So what I would say is don't see it as a burden, see it as a thankful duty, you know? You know,

Tiffany-Ann Bottcher:
Break.

Tiffany-Ann Bottcher :
percent.

Trivelle Simpson:
Book it off like you book off your birthday. Don't give yourself an excuse. Most times in this country, we have a two month lead time before an election, right? If they snap call an election, past couple of times it's been votes of no confidence. They snap call it two months ahead of time, you know the date, just book it off. I get it, it's hard to do before or after work. That's the first step. Let's just book it off, show up, give yourself a free day, go have a lunch, go with your friends, make a party out of it. Me and my college teammates, we play fantasy football.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
Sometimes around election, we'll do fantasy politics. Hey, who do you got? Man, I think, you know, we get a group chat going or we're laughing or we're taking wagers and we're betting. And then on election day, we're getting together, we're having wings, make it an event. Because when it's this somber, oh, I have to do it on my lunch hour, the line is long, okay, I'm not going. I don't know that we get the change that we want. I think on an internal level, we have to see it from a different perspective.

Tiffany-Ann Bottcher:
My bad. Yeah.

Tiffany-Ann Bottcher:
Well, and I think as business, you know, as business owners that can help influence this, you know, and it's not just, hey, I need to take the day off. It's number one, as a business owner, prioritizing making it happen, but also making it happen for your team and making sure that people don't, you know, because some people won't want to ask for the day off, but saying, hey, it's election day. Would love it if everyone could participate. Whatever you're doing, left, right, doesn't matter. I just want you to go and do your part. And so as business owners, we can do that.

that we can help encourage that direction and make sure that there is an inclusivity in the availability to go vote. Every year I take my kids, I want them to know, they go, we go, we fill out the slip in the thing, and just so they're part of the process and get to know what usually, each of my kids has got to go at least once, and that's kind of always been our process. And it's the same thing, people who are...

historically busy and more success equals more busier. And I try not to quantify. You know, somebody, one of my mentors a long time ago said busy is, he doesn't subscribe to the word busy. He's like, you're busy and my busy, two very different things. This is not a unit of measure. Like, you know what I mean? And so, but it often, we also see it come up in, if we're talking politics and diving in, but you also see it when people get elected for jury duty. People say,

Trivelle Simpson:
Right.

Trivelle Simpson:
Mm-hmm.

Tiffany-Ann Bottcher:
I'm too busy and they do everything they can to get out of it. And my concern with something like that is all of the people who are then making the decision are maybe the people who aren't so busy. And I, you know, podcast, but I'm using those, the finger quotes, not so busy. But we want a good variety of people voting, whether that is in an election, whether that's in a court case, whether that's... We have to have a good sample.

Because those are those super successful people are the first people to complain about policy and the effect on business and the wrong person in. And but they're not always the people that always show up to make that vote or do that jury duty because hey, they're busy. And so, and I, I get it. I'm, I, we all, we all got lots going on, but I think it's time that we all collectively work together to make it happen.

Trivelle Simpson:
Yeah, I mean, I've partnered with other companies before on election day. We make it a mandate. Your only job for the days to go vote. And then we have, you know, that's it. It's technically that's your task for the day. Everybody working from home will vote. Um, but I mean, I think there's that sense there's, there's obviously there's interesting, interesting trends in society. We, we mark them internally as a business. It's part of our consulting work. We have to understand sort of urban planning, urban planning economics.

Tiffany-Ann Bottcher:
Bye.

Trivelle Simpson (15:54.017)
So people shifts in different sort of demographics are operating in different ways. And an interesting way you're seeing it is even in the types of people that are having children these days, that the well-educated working class individual as time goes on aren't having as many kids because they say they don't have time. And then usually the people who have a lot of free time are having all the kids. And that I think builds an interesting.

Tiffany-Ann Bottcher (15:54.07)
Yeah.

Tiffany-Ann Bottcher (16:11.342)
Mm-hmm.

Trivelle Simpson (16:21.185)
question for what society is going to be tomorrow. Because at the end of the day, we're getting an overpopulation of people that are going to have values that came from the product of their environments, right? So I think, I would say, you're never going to have utopia. But I think in these instances, community thinking helps. There's so much echo chamber thinking that happens, even in business. But I think business, you can go fast alone, but you go far together. Collaboration is something that I think you and I

Tiffany-Ann Bottcher (16:31.022)
Mm-hmm.

Tiffany-Ann Bottcher (16:41.454)
Mm-hmm.

Trivelle Simpson (16:51.293)
Understand deeply there'll be times I'll be beating my head against the wall trying to do something trying to do something I could meet one person hurdle it jump twice go around the corner back and because they just had that unlock They didn't even know what it would do for me So I think as business owners we have a different sense of collaboration because we have all these real-world pieces of evidence Of how it's worked But I also think that what people don't understand is we also have the real-world understanding of the risk I've partnered with people before and it was a terrible idea right now. I had to live with that as well

And I think that, you know, if there's any role that we can play is to say it's okay to take a risk and pay the price because big enough risks, you only have to get right one time for it to be worth it. I think, you know, Abraham Lincoln's statistic in elections, he was like 20%, I mean, he was losing a lot, 80% losing streak, but he's known because he's this guy and he did this thing and it's incredible.

Tiffany-Ann Bottcher:
Yes.

Trivelle Simpson:
The same thing works with venture capitalists. Some of your favorite venture capitalists have terrible win rates. They only got it right one time. But if you get it right one time, you can kind of eat off that and live off that for many, many years. Another one is, it's one of my favorite movies, Eduardo Saffron, the co-founder of Facebook, Mark Zuckerberg. Yes, the settlement, hundreds of millions of dollars, spins out of venture capital company. No winners, no winners. It's been almost 20 years, not a single winner. But guess what? He's Eduardo Saffron, co-founder of Facebook, and that's okay.

Tiffany-Ann Bottcher:
Thanks for watching!

Trivelle Simpson :
And I think that we have to survive in that same way.

Tiffany-Ann Bottcher:
Yeah, I think that when you, you know, it's the, if you go back to being young, I remember by, I was like 17 years old and I used to teach riding lessons and I used to make $25 to teach a riding lesson at that time. And I would go and I would take that $25 and I would go to the gas station and I had a little Chevy Cavalier and I went to that $25 and buy a full tank of gas and at that time in my life, I say those were like the $25 problem.

Trivelle Simpson:
Go!

Trivelle Simpson:
Okay.

Tiffany-Ann Bottcher:
kind of days. And then one day it was like $100 problems. And then as you grow and businesses grow and whatnot, and suddenly you're making million dollar decisions or $100,000 decisions. And it's such a shift. But if you're at the wrong time or you're looking at the wrong problems, a person who's dealing with $100 problems suddenly has a $100,000 problem and they don't have the skills to even work through what makes sense. But when you've got...

Trivelle Simpson:
Mm-hmm.

Trivelle Simpson:
Mm-hmm.

Tiffany-Ann Bottcher:
whether it's someone who's doing these big deals in venture capital, there may be lots of losses, but they've also had lots of wins to cover. It balances out in a way, and the overall might not be great, but to that same person maybe losing a million dollars is the same as somebody else losing a hundred dollars. Really just depends on where you're at, right? It's such a different.

Trivelle Simpson:
Absolutely. Yeah.

Yeah, it's all mentality perspective. I think...

Tiffany-Ann Bottcher:
It's such a different thing.

Trivelle Simpson:
I think I have a very good memory. So I like to remember the days when I had $20 problems, you know, because you kind of realize that problem solving is the same, you know, the way you handle it, take a deep breath, think of your options, do all of those things. There are applicable skills at every level. But the truth is that if you hit a moment of true momentum.

Tiffany-Ann Bottcher:
Yep.

Trivelle Simpson:
There's nothing that really prepares you for it. So you have to rely on your previous skills. So yes, it's a different concept, but the core value of how you handled the $10 problem is how you will handle the million dollar problem in terms of its core concept. And the success of any business or any individual, I always look at this with athletes, athletes are called the greatest of all time, but we'll win like five championships. Michael Jordan played in the NBA 15 years, won six championships. He's the-

Tiffany-Ann Bottcher:
Yes, of course.

Trivelle Simpson:
He'll call him the best of all time. LeBron James has been in the league for 20 years. I think he has, what's it, two with Miami, one with Cleveland, one with LA. That's only four championships, 20 years, 16 years. He didn't win. He's Mount Rushmore of basketball because sometimes it's just about a run. It's just a run of form that if you ride the momentum properly, it's not about, you know, it's just about handling it with grace and dignity and the same way you handle the $10 problems and you'll be able to go from strength to strength. That's what business is like. You know, people.

Business is like children. There's never a good time. You're never gonna be ready. You kinda just gotta get in the arena and you start throwing punches and see what happens.

Tiffany-Ann Bottcher:
Right. Are you familiar with Tim Grover, the author? He talks a lot about Michael Jordan and lots of different... And I didn't grow up, you know, zero basketball in my life at all and have... So didn't know much, you know, it's like, I mean, you know who Michael Jordan is, of course, but like didn't... It wasn't... I didn't know much about it. And I got hooked on one of his books during COVID and have since read another one. And I absolutely love him. And never if, you know, if any of our listeners have not...

Trivelle Simpson:
Thanks.

Trivelle Simpson:
Yes.

Tiffany-Ann Bottcher:
great audiobook. You know, there's books and then there's like good audio books that are like so well done. His is the audio actually I think elevates the book instead of takes away. Some of them it doesn't. He does an incredible job. And I'll link both in the show notes that I've read because they are two of I think my favorite. I mean, I do a lot of.

I said a lot of reading. I don't do a lot of reading anymore. I used to do a lot of reading. Now I do a lot of audio books. It's not the same thing, but his too would be two that I recommend to almost anyone. Um, and even, um, have shared parts of some of them with my kids who are, um, you know, aspiring athletes and whatnot, and some great mindset pieces there for life. Um, you know, health business, just, just incredible. I'm a huge, huge fan of his for sure.

So let's talk a little bit about the venture capital part of your business, the risk and the market and whatnot. And let's, you know, obviously the politics is such a big piece for you now, but you've got this other aspect that has been such a key part of your business and life journey. So let's dive in a little bit on that.

Trivelle Simpson:
No.

Trivelle Simpson:
No.

Trivelle Simpson:
Yeah, I would say that, you know, the crescendoing of our entire venture business this past year, we did a competition called drive to 50, where we gave away $250,000 to a winning entrepreneurship idea. It essentially was like a pseudo shark tank, dragons, Dan type thing. So we do, we did competitions on Instagram and the way people would make it to the next week, borrowing from American idol is views and likes. So if you've got the most views and likes, we accumulated that score. You move to the next week.

and then you got little challenges that would have to be your sort of video vignette. So as people follow on Instagram, they had a rooting interest and then we shot this sort of final show that we put on YouTube. Now the first season is really just a short of quality, but it houses the spirit of what I like about venture, venture investment. I remember once somebody said, the world is not short of people with money, but it is short of people with good ideas.

How do you get people with good ideas out of hiding? You gotta offer them money. So it's this interesting thing where I am just, I am so inspired by entrepreneurs. I think of a cheap plug, Happily AI, who was the winner of our competition. And what they do is they essentially amalgamate different funding sources and allow you a single click option to apply.

Tiffany-Ann Bottcher:
Hahaha!

Trivelle Simpson:
And that's huge for me. I used to work at a tech company and I remember spending a month on a shred claim once and with these guys, it's a single click and you can kind of go from strength to strength and so simple. So I would have never come up with that idea, but I would love to invest in that idea. And it's so interesting because the owner of the business, he says to me, we might not find the cure for cancer. We might not help people with rents. We might not do this, but he goes, we might fund the company that does so.

And I think that's how we feel about our venture business. We want to be in the room and have the conversations of people tackling and challenging some of the largest issues in our space. So for that reason, we like to focus on Canadian entrepreneurship because I think that's an underserved market. We like to focus on bipartisan women investment because I also think that's an underserved market. And there's a huge push happening in the States that we don't quite have yet, which is a direction to fund female entrepreneurs. It's a multi-billion dollar business.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
There's literally billions of dollars waiting on the table for female-led entrepreneurs. I'll tell you why. Most people know women drive the market. They do all the shopping and things like that. We live in a sit-in time now where CEOs, entrepreneurs have to sort of sell their image along with their business. Gone are the days of the infomercial saying, not only am I the president, I'm also its first client with the cheap infomercial. You want people to feel like they're having a lived experience when they use your product?

Tiffany-Ann Bottcher:
Yes.

Trivelle Simpson:
So to us, it's a no brainer. We want to have that as a target. Now, it's near and dear to my heart because I worked as the head of operations for a female CEO for five years. And I saw what it was like when we would go get funding opportunities and how the doors would shrink a little depending on how they look at the org chart. So we don't, I think, wanna be part of that. So we wanna kind of lead the charge. Excuse me.

Which is why for our drive 250 competition, we wanted it to be a show because we want this to be something that goes on record. So yeah, we're, we're a mid tier venture. Um, we try and keep the checks that we cut down to, uh, you know, $3 million, $5 million, probably the max that we're going to do, um, ownership percentage, obviously varies based off the business. But what we like to do is we like to sort of social media lies or YouTube eyes, every investment we want there to be a record.

So that five years from now, six years from now, seven years from now, more than just a record that, hey, we were with these businesses and it's great, but we would have a roadmap on how the other venture companies will follow suit. So we're trying to add good principles to venture investment only because in this country, venture capital is usually very esoteric. It's companies you've never heard of. You don't know who's behind them. You go to their websites, there's nobody to contact. You can't even email them. It's all of this closed door type system. And I think

Our hope is to change that.

Tiffany-Ann Bottcher:
What an incredible mission. And I think, you know, it's, I've been in enough of those meetings, both in a woman CEO role, but also, you know, I was a VP of finance and tech, part of a very successful business partnership that had that very charismatic, you know, male CEO leader. And I will say, you know, number one, I learned so much from, you know, watching and being a part of those meetings. And I think that,

Trivelle Simpson:
Is it?

Tiffany-Ann Bottcher:
there's so much value sometimes from even just being able to be in the room and learn how these conversations go and whatnot. There's a lot of study, you know, there's a lot of statistics that go into, you know, men will be willing, more willing to ask for things women will feel less qualified. I was actually on a call just last night working on a potential, you know, great position for someone that they are so, they've been working with us for a while, but we're going to make that a little more official.

And she said on the call, she said, I don't know how I earned this opportunity. I'm having such, you know, of this like feeling of just like, I don't belong. Like she, and straight out on the call. And I was like, no, you don't, you have already earned this spot. You aren't even doing this. And so, so interesting. And I think it really plays into.

Trivelle Simpson:
Did you?

Tiffany-Ann Bottche:
you know, people being willing to go and ask and take those steps and believe in their vision and whatnot. And so actually sharing some of those conversations and processes, I think helps people build confidence, see other people doing it, you know, and so kind of taking it out of the shadows and bringing it a little more forefront really helps change the future in a really serious way.

Trivelle Simpson:
Yeah, I think part of the reason I became an entrepreneur, when I think back about my childhood, living in this country, there's not many head offices here. I mean, when I was growing up, there wasn't Google head office, no Facebook head office, no Microsoft head office at the time. So the idea of the life that I dreamt of and what I wanted, I couldn't get doing the go to school, get a good job working with the latter. I had to make the business that would pay me what I thought I wanted.

Tiffany-Ann Bottcher:
Right?

Trivelle Simpson:
Um, and I think that's true of a lot of people, you know, this is being specifically here in Canada is, uh, sure. Okay. One tenth the size of America. Fine. Um, but such a huge landmass, such vast difference of people. When I think of that, I really do think of a land of opportunity and dreamers because there's nothing but empty space. You know, if you go to New York, yes, you're motivated, but you also feel the weight of, I can't feel any more space here. It's full.

It's they're done. It's New York. I Go to so many different country so many different cities in this country and I see opportunity Oh, man, I wonder what could go there. What could be built there? I wonder who's gonna fill that space man. You guys you guys have this studio here No, you don't and it's just I think that what we want to do is You know doing shows like this Publicizing our venture is we want to normalize people saying no, you know what? I'm gonna give it a try on my own

Tiffany-Ann Bottcher:
Right. Yeah.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
If only here, one thing that was so revolutionary for me is I do this thing. So because I played football, I have all these athletic habits that I don't know how to get rid of in business. So one thing I used to do in football is you watch a lot of film. So, you know, you watch your opponents or, you know, you watch yourself at practice to kind of see. So one thing I do is I read and listen to business profiles all the time. I'm always like deeply into stories of other entrepreneurs. And I'm not just talking about.

Tiffany-Ann Bottcher:
Right.

Trivelle Simpson:
the successful ones. I'm talking about the failures. Like I did, I looked into Elizabeth Holmes, who was there I know, cause I'm trying to figure what happened, where did that happen? Like why? Cause you wanna see the similarities, the differences. One thing that stuck out to me, Bill Gates, they're talking to him and they say, hey Bill, why'd you leave Harvard to make Microsoft? What'd you decide to do that for? I thought he was gonna say, like I believed in computers, it was the future. Something very clairvoyant, very Bill Gates-y.

Tiffany-Ann Bottcher:
Yes.

Tiffany-Ann Bottcher:
Right.

Trivelle Simpson:
Bill said, because if I failed, I knew my dad could get me back into Harvard. I sat with that for a month and I'm like, wow, like Bill Gates is it highly intelligent? Yes. Highly capable. Yes. But at the end of the day, Bill was just fearless when it came to taking a risk because he thought he had cover. Now, could his dad have gotten him back in? Look, Bill came for money. He, I'm sure it would have worked. It would have, there had been some pain, maybe some embarrassment, but he's going back to Harvard.

Tiffany-Ann Bottcher:
Hahaha!

Trivelle Simpson:
And then the battle really became, if the secret is fearlessness, how do we as entrepreneurs just have that? Just have the fearlessness because you're not gonna make Microsoft unless you leave Harvard. So whether you think it's that your dad can get you in or whether it's that you're fearless enough to think you'll figure it out, you gotta leave Harvard. And I think that's what we wanna start to sell as a concept that, you know.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
Safety nets are fantastic. I don't I don't not believe in them, but I'll say this if you're an entrepreneur You have an ego that believes that you have an idea good enough that people should compensate you for it That's what that's what it is, right? If you have that much belief then believe enough in yourself to think if you miss you'll figure it out before you hit the ground That's what I always said if you have enough confidence to think you know what? I'm gonna go out on my own. I can do it better than everybody I've seen do it Then don't delay that belief by waiting to make a safety net

Tiffany-Ann Bottcher:
Yes.

Trivelle Simpson:
Believe that you are capable enough to fix it no matter what happens. Because that's what it is, no matter how successful or unsuccessful you are. There are times I have meetings in the morning, I have no idea how I'm gonna fix it, but I gotta fix it by the end of the day. So then you make phone calls and you try things and that's just the game. So why not start the game with what the game is gonna require? And that's just what I see consistent throughout multiple entrepreneurs, the successful ones, the unsuccessful ones, the funds that go high and go low. It was a willingness to take the risks, the fearlessness.

Tiffany-Ann Bottcher:
Great.

Tiffany-Ann Bottcher:
Absolutely.

Trivelle Simpson:
And that fearlessness has to be driven from your utter confidence in your discipline or in your vocation or in your abilities. You got to believe your own hype, you know, got to believe your own hype or else, or else nobody else will.

Tiffany-Ann Bottcher:
Absolutely.

Tiffany-Ann Bottcher:
It's interesting, you know, I so I'm fairly I would say risk adverse and my decision I had a I'm not gonna say a cushy corporate job. I was a partner and I worked at the time I felt like I worked my ass off. But we also had many a business lunch and whatnot. It was a very different, different vibe. I mean, I worked super long days away from my young kids. We were you know, one of the fastest growing companies in Western Canada and it was it was all it was great.

Trivelle Simpson:
If you're

Trivelle Simpson:
Okay.

Tiffany-Ann Bottcher:
But you get to the point where you're like, hey, I'm spending a lot of time around a boardroom table talking to people about, you know, and I was like, I want to do something different. And I made the decision to leave and start my own business, that entrepreneurship piece. Now, as someone who's pretty risk adverse, I go from, you know, I had the super nice company car and the company phone and lots of zeros on the paycheck, big mortgage, life built around all the money.

Trivelle Simpson:
Mm-hmm.

Trivelle Simpson:
Anything? Nope. Anything? Nope.

Tiffany-Ann Bottcher:
And it's like, hey, we're going to do this. And my husband thought I was crazy, for sure. Absolutely thought I was crazy. And I didn't know exactly what I was going to do. I knew I was just wrapping up my MBA, which was going to not be super useful as an entrepreneur. I mean, I'm glad I have it. I love school. I'm glad I did it. But ultimately, it makes zero difference to my entrepreneurship journey, whether I finished my MBA or not. Would have been worth more in the corporate world, add a little extra money or whatever. But that's not why I did it.

Trivelle Simpson:
But, yeah.

Tiffany-Ann Bottcher:
So, and I had no idea, but I was like, you know what? I've been doing this for like 12 plus years. I've got all this education. I don't know exactly what I'm gonna do. I don't know what I'm selling, but we're gonna make it work. And so, you know, two and a half years later, things are, you know, we've got a huge client base all over North America. Things are doing really well. But that decision, that decision to leave that safety net, I mean, that was probably the biggest decision of my life.

Trivelle Simpson:
Mm-hmm.

Mm-hmm. And it's the one that you had to make. You know, it's so funny. It always feels like the cushy job is what gets us all. I was working at a beautiful space. I'm bilingual. I'm fluent in French. I was a regional auditor. I was going to Montreal once a month. They had an apartment for me, a card. And I had this job, and I was 20.

Tiffany-Ann Bottcher:
Yes.

Trivelle Simpson:
23, 24, 23, 24, newly graduated from the York University, making more money than I thought I knew what to do. I could not believe it. And I just had this desire to learn how to manage my own money. And I have this job that I have this extra capital. I remember when I went and told my parents, so my mother's an entrepreneur, which is funny. It's funny because of what she says. My mother's an entrepreneur. My father, I think, always wanted to be. But you know.

Tiffany-Ann Bottcher:
Yeah.

Trivelle Simpson:
man, God love him, really felt the, not the pressure, but the responsibility of being a father and a husband and just never wanted to risk it. Just felt, you know, if my wife was taking a chance, I gotta be the one with the consistent paycheck, I'm not gonna do it. And then there was a period of time where he was gonna try, I have a little sister, we're 10 years apart. So, you know, he has me, he goes these years, about nine and a half years in, he thinks, you know what, I'm gonna give it a go now, we're established.

spent like two months trying to be an entrepreneur and then my mom was pregnant again. So that was it. That was it for him. When I told him I wanted to quit, my father's more like, kind of like, hey man, if you want to, then sure. My mom had more, it was like talking into my soul, kind of grabbed me, I'm pretty tall. And she says, it's gonna hurt more than it's gonna make you happy. But the happy will cover the times that it hurts.

Tiffany-Ann Bottcher:
Yeah.

Trivelle Simpson:
I'm like, what do you mean? It's gonna hurt more than it'll make you happy, but the days that are happy will cover when it hurts. If you can handle that, then I wish you success. And I think that sometimes when people see entrepreneurs or businesses, they think 365 days in a year, 300 of them are fantastic, probably not 65 rough days. The truth is, 300 days are pretty damn stressful. 65 where you're like, wow, look at what's happening here. But you gotta love it. You gotta love the game and the joy.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
So I was so happy to get that advice that, you know, you think, I always used to say, oh, I didn't quit my job to work for somebody, but I traded in my one manager for my client list of 5,000, I work for 5,000 people now. Or how you service your staff is different. I used to think, you know, as a man, it was so interesting, because I was a manager, I was in these leadership roles, supervisor roles. There's a way that you supervise, because you can always say, oh, the message came from up top, sorry guys, this, that, that.

Tiffany-Ann Bottcher:
I'm sorry.

Tiffany-Ann Bottcher:
Uh-huh.

Trivelle Simpson:
versus the way you have to lead because they know this is your idea and you have to sell it a totally different way. They know you can't, and I was in those first couple months, I realized I'm like, man, because I was starting, I'm like, I'm great at leading people. This is fantastic. But what I was great at doing is I was great at kind of deflecting. So I'll take the message from ownership and I'd be able to congeal and politicize my team and.

Tiffany-Ann Bottcher:
The buck stops with you. Yes. Yeah.

Tiffany-Ann Bottcher:
Mm-hmm.

Trivelle Simpson:
Get them just enough to think I'm on their side with every part of it that was great. Get them to think it wasn't my idea, the parts that they didn't like, so they don't turn on me. And now I motivate and then I go to my managers and the numbers are great. And it was fantastic. When I hit ownership, and I realized that first, I never forgot at the first staff meeting and there was pushback. And I realized that I can't use any of my tactics because it's nobody else's idea but mine. And there's no answer to this. I can't say, well, the client wanted or.

Tiffany-Ann Bottcher:
Yeah.

Tiffany-Ann Bottcher:
Nope. Yep.

Trivelle Simpson:
Because it's me, it was I. And learning that was such a weird, unique thing, which is why, what I learned from that is as a staff, we don't do meetings. So I say meetings are only to build culture, information we do digitally. So I'll text you, I'll call you, I'll email you. But if we all come together, it's so we build community. We gotta feel.

Tiffany-Ann Bottcher:
Yes.

Trivelle Simpson:
in one step because we have to survive those moments when I know you don't agree with me, but you gotta know, you know, we're still tribe, we're community, but there's gonna be a lot of days you're not gonna agree with me. And that was weird too, because coming from traditional corporate Canada, we had meetings for everything. I mean, we'd have meetings about how to open the door in the morning, everything. And they're all 30 minutes to an hour. For no reason, for no reason. You always start in some way, hey guys, just give me a quick touch point. When I heard quick touch point, I know, close the, I'm gonna be here for at least an hour. This is...

Tiffany-Ann Bottcher:
Everything.

Tiffany-Ann Bottcher:
Oh, at least. At least.

Trivelle Simpson:
Quick touch point, why is there 400 of us in here? You know, it's just not fair. But yeah, I never forgot that, that leading as a supervisor versus leading as an owner is dramatically different. And I don't know if I was ready for how different that was.

Tiffany-Ann Bottcher:
It is, it is very different. You know, the buck stops with you. I love the moving away from meetings. It's something for me, you know, meetings, so much wasted time in a lot of businesses, sitting around, you know, listening to people talk about things that have, you really, it's like send it in an email, a quick update, but like, I don't need to know your nitty gritty and has nothing to do with me and what I'm doing over here. And so I think for things on like, you know, really talking about culture.

Trivelle Simpson:
Thank you.

Trivelle Simpson:
Mm-hmm.

Tiffany-Ann Bottcher:
talking about values like this is where we're going and like kind of those like, you know, annual, like let's dive into what the objectives are this year and let's, you know, break bread and discuss and get everybody on the same page. Love things like that. But so much, I think that there is so much still to come in terms of optimizing those processes and really just giving that time back to people who use it for.

Trivelle Simpson:
Thank you.

Trivelle Simpson:
Mm-hmm.

Trivelle Simpson:
Yeah.

Tiffany-Ann Bottcher:
Good there, you know, it's like they're you you're wasting time that could be driving to the needle So, you know so many so many valuable pieces here to bell When you know, what is one thing that someone could implement in their business right away? You know, what is that advice that you have for someone that can help them see that win?

Trivelle Simpson:
Yes.

Trivelle Simpson:
Yeah. So I thought about this because I've been chewing on this one because I love that you want something that in the immediacy. So I'll say two because I don't necessarily know the audience. So I'll say this, if you're a person who exists kind of in the moment, you have a general vision for your business, use this week to vision cast it. Get a piece of bristle board, cut out pictures, write it down, have it as a physical image, a physical representation, something you can see and meditate on. You'd be dramatically surprised how that will change.

your focus. It, you know, on the rough days, on the good days, just having that image, not this sort of subconscious subtextual thing, but a raw piece of an artistic element you worked on, I think is great for focus. That's the first thing. I'll give three. Second thing, we touched on it. Cancel all your meetings this week that are for informational content. Only keep the ones that are for culture, but cancel all the information meetings.

And like nobody cares. The annual report stuff, cancel all that stuff. Send in an email or send like voice notes, right? We have what send voice notes, you know, verbal does work. Cancel all that. You'd be very surprised how much more productive people are gonna be. You're gonna see people with an extra hour, hour and a half, two hours at the end of their day, just because we didn't have meetings. And that'll allow you to have a more productive week, my personal opinion. I think one week is a good sample size for that. And the third thing,

Tiffany-Ann Bottcher:
Yeah.

Trivelle Simpson:
that I always think is a doom's way strategy. A good leader has to replace their tasks consistently. This is my belief, that if there's something, and I try and do it in an interval of about a year and a half to two years. So if there's something that I had to do two years ago, if I still have to do it today, something's wrong. So if I have a list of 10 things, the goal is that

Of my 10 things, two of them have to be off my list because I gave it to somebody. But what that allowed me to do is add another two so the business is growing. I would encourage any entrepreneur this week to think about the things that are currently on your to-do list, okay, that you wanna get rid of in two years and who you wanna give it to. You'll be surprised how much it'll help you mentor that employer or that partner in a different way. You'll see them in a different light because you'll understand how integral they are to the business and they will also then understand how integral they are to you. So those are the three that I'll give for the week.

Tiffany-Ann Bottcher:
Yes.

Tiffany-Ann Bottcher:
Absolutely incredible value there. Absolutely. Okay, where can people connect, see this content that you talked about, talked about YouTube, we've got some short form video out there. Where can people see and connect with you?

Trivelle Simpson:
Yeah. So obviously the hub is the drive group dot CA that's T H E drive D R I B E group, J R U P dot CA that's the easiest hub to find everything on Instagram. We're at the drive group, Inc. So the drive group and then I N C, um, and to find me, my Instagram handle is trip Simpson T R I V S I N P S O N on Instagram.

And if you use any one of those three things, we'll direct you to the other stuff. We're gonna have handles going for days, but definitely drivegroup.ca at the Drive Group Inc. Or at Triv Simpson, if you wanna get in touch with me personally. And yeah, that's where you find it all.

Tiffany-Ann Bottcher:
Haha

Tiffany-Ann Bottcher:
Well, thank you so much for being here. It's been an absolute pleasure.

Trivelle Simpson:
Thank you. Thank you so much. Appreciate it.