Steven Leclair | Wealth Management Transitions for Entrpreneurs | Damn Good Day

It is a damn good day to have a damn good day! We're live! Steve Leclair, you're in the building! Let's go, man! How are you doing?

Thank you. Actually, the very first time we met, you know, we met through a mutual friend. We had so much fun together, and just since then, so many great meetings. It's been awesome.

I agree with you, man. It's one of those things. I've got two grown children, and they actually make fun of me because they're like, 'Dad goes anywhere in the world and he knows somebody. He runs into somebody he knows.' And it's very true. But I do exactly that: I just put myself out there. But here in Miami, the way I describe it to people today is it reminds me of my first week in college. That first week, everybody's showing up, everybody's from someplace else, and it's like, 'Hey, I'm Steve, what's your name? What's your favorite color?' So it's been a lot of fun. I think it's really easy here to meet people.

I came from Ohio, Columbus, Ohio. I still maintain a residence up there. I moved to Ohio in 2003. I've got family roots there, but I'm actually originally from the Colorado area, a little small town in the mountains just outside of Denver.

Yeah, absolutely. So my day job is wealth management, but our wealth management business is just a little bit different. So yeah, we work with some ordinary, average type of situations, but we work with a lot of business owners. It was something that I really got interested in about 15 years ago: the wealth management that's associated with business owners. Because where I was trying to create my own business, I saw a lot of myself replicated in the people that had run into it. You dive into work, you put everything into it, and then you wake up 30, 40 years later, and these people have substantial businesses. But at the same time, it's their baby, their life's work. The day they sell it is quite sad for a lot of them. It's quite sad to see their baby and let it go. I've seen a lot of myself in that as well, as I've always been willing to jump on a plane, go chase another deal, learn about a new family. But that's one of the things I love: I've had so many experiences with so many different families and businesses. So if you ask if there's one story in particular that I like the most, the answer is no. It's probably the next one. It's the upcoming family I haven't met yet that's probably my favorite one.

That's correct, yes.

That's right. You're one of their very close, trusted advisors. What's interesting about business owners when they go through that sale process is most people don't realize that a key manager or the key managers of the business actually have more liquid wealth than the business owner does. So it's not until they sell that they become the actual rich person. They were a rich person on paper, but they couldn't spend it; it was all tied up in the company. It's that date of sale when all that money comes to fruition because they're just reinvesting every penny, every ounce of sweat, right back into the company.

Yeah, there's actually several. It's fascinating to go through the process with them because it's quite emotional, with a lot of highs and lows along the way. As much as you think that a business owner with a business worth tens of millions or over 100 million dollars would be sophisticated, knowing about investments and tax advantages, the answer is they don't. They're in uncharted territory, just like everybody else. Post-sale of the company, they go through a trial, a tribulation, with their emotions on a pendulum swing. They don't understand public markets. They turn on CNBC with the same question as everyone else: 'Why is that up today? Why is that down today?' Because when they were operating their company, it likely wasn't public, and they'd never seen it go up and down. So it's a real, hard, emotional time.

No, the vast majority of our companies sell to another private company or to a financial buyer, to private equity.

That's the rarity. I find it fascinating that so many people, in this world, you assume they are X and X, but really it's just a lot of people winging it.

Yeah. I think it comes from their backgrounds as well. It's very rare that most of them either inherited the company or, if they had, it was a substantial size. So they come from an average, normal background, just like most people.

Oh, it really is. It's one of those things that keeps me jazzed because you find out every aspect of the business, but also every aspect of their personal life. One of the biggest joys in wealth management is you become part of the family. You're like the third psychologist: there's a huge psychological component. You share in their successes and grieve with their losses. You really have a bond with the family, and it's special.

On the same team, with the same goal to have the best outcome possible.

Expectation setting is always an issue. It really comes down to personality type more than anything else. As you can imagine, a lot of successful people have very strong personalities. They're entering a world where they're not necessarily in charge, but they used to being in charge, having control. They no longer have control. That can be difficult, just like the process of getting acquired, and all of a sudden they're not the boss.

There's almost always is buyer remorse, or seller remorse we should say. So you probably go through a process of determining if this is what they really want to do.

That makes a lot of sense. That's powerful. But there's also this huge upcoming wave of these young, super successful crypto millionaires... not anymore. But they're working that deal too. What's your process of taking on a new client? Does a lot of it come from referrals? I can imagine if I'm a business owner, I'd be very skeptical about putting anyone in charge of selling my baby.

That's a beautiful question. What I like about it is the assumption that there's screening or prospecting that goes on. Originally with our business, that's true. But where we are today, between myself and my two partners, we're really known within the industry. We have a lot of inbound and referrals that come our way, or when we do outreach, people know who we are. We have a great reputation. A lot of our business owners come from a handful of industries, so you know who the clients are. When you start to take them through the process of choices, you can quickly understand if there's a meeting of the minds and chemistry between you. When they're looking at us, they're looking at our chemistry too. If their expectations of what we do aren't in line, it's very evident, and we'll step out. But we're always willing to refer them to another group who may be a better fit.

Correct. With my two partners, there are delineated roles and responsibilities between us. I'm more involved with the company post-sale. My other partner, Danielle, is really involved with the company pre-sale. My partner, Michael, is usually involved several years before it sells. You can almost think of it as a conveyor belt: who's involved with the family or company at what point.

Yeah. I never intended on going into the wealth management business. You hear this from so many people: their career and life work was a byproduct of a mistake. When I graduated from college, my daughter was born when I was a senior. I was 21. So at 22, I graduated, wanted to go to medical school, didn't get in, and needed to get a job. .com and telecommunications were all the rage, so I got a job selling telephone service. It was a right place, right time thing. They told me to go cold call businesses. I walked door to door in Denver, Colorado, selling phone service. It worked; I was good at it. I ended up working for three different telephone companies, and all three went bankrupt. When the third one went bankrupt, I thought, I have all these worthless stock options. Maybe I should learn what this stock option stuff is. That's what got me interested in finance and the stock market. I thought, this last company was one of the biggest bankruptcies in the U.S. in 2002. So people worked for these companies for 30 or 40 years, and then one day it's time to retire. I know they're just as clueless as I was. On the first day, they tell you to fill out a benefits package, and you hope you checked the right boxes. My idea was: someone needs to create a program to educate employees on their benefits and how to create a financial plan. I started cold calling financial services companies, and one took me up on it. I got the job. When you start in financial advisory, you're not given any business. I was paid a salary of $3,000 a month for six months, and I thought I'd won the lottery.

Well, this is the beauty. In telecommunications, I learned that you can call the biggest company in the world or the smallest, and they'll tell you no at the same speed. So you might as well start at the top. Within that first year, I started calling all the Fortune 500 companies, pitching them on this idea. I just hammered phones. Fortunately, one of the top 10 picked me up and said, 'That's a really good idea.' I started doing financial planning for their executives. That was my breakthrough, about a year into it. I have no idea how many thousands of cold calls it took, because it was the same companies over and over. But within 12 months, it was life-changing. I traveled with that corporation for about seven years. When some fundamental changes happened in HR, I thought I wanted to do something different. I called that the first chapter of my career. I moved on to chapter two: working with business owners, focusing on that major liquidity event when they sell. I've been doing it for over 20 years.

It's been a fun journey. For my friends who do door-to-door sales, I've got to say it's the most intense, best learning experience any human could ever have. It was brutal. I was 22 with a baby. They told me to walk door to door, and I had nothing else to do. All the other sales guys would be golfing or at the bar on Friday afternoons, and I thought, 'I can't afford that. I need to make money. I have this kid.' It was a motivational force. I was wired to be successful, but now you have obligations, and you're going to fulfill them. It helps silence those inner thoughts. I was so young, work was my outlet. I was escaping from the reality of my life through my work. I still do that to a large degree. I plowed all my energy into cold calls, starting early in the morning and finishing late when businesses locked their doors.

Absolutely. Everybody who says cold calling is dead is wrong. It's still alive and well because there's always going to be a personality that matches yours. There's always someone who vibes with your message. If you get on with the right person, your whole life can change.

For salespeople, it's almost like a drug. Once they hit that sale, it's that euphoria, that success. They love it. I think of all the times I've been told no. At 45, when someone says no, I feel it. When I was 25, it was just 'whatever, I'll keep moving on.' Good salespeople have that thick skin. It's always, 'Hey, I'm one step closer to the next one.'

It's also interesting that anyone can go out there and start making those cold calls, but after that, once you get the sale, it's about delivering great customer service, building trust. What are some of the things you have found that helped build that trust with clients early on in those relationships?

That's true. We all make mistakes. Sometimes they were from blind ignorance, other times because we didn't know any better. How do you not repeat that? One of my big mantras is: if something went wrong, if I were faced with all the exact same information all over again, would I make the same decision? If the answer is yes, then it wasn't a mistake; it just didn't work out. The mistake is when you blindly make a decision, ignoring something.

The learning hurts, but that's the only way we learn.

But there's also some monotony in business. We're in a world where everybody's starting to hate on Tom Brady. He's 45 years old, and every day he practices the same three-step, five-step, and seven-step drop. How many people have done that for 40 years? The day he stopped, he would no longer be Tom Brady. That's a big part of business: every day you've got to go out and practice your three-step, five-step, and seven-step drop. A lot of people get away from that.

But it's never people who are doing better than you that want you to fail.

There's a comforting feeling when you're surrounded by other people who make you feel more comfortable with what you're doing. That's why I'm so grateful for Peter and this whole gang. Every time I get to hang out with you or any of these guys, I'm inspired, I have fun, I get to learn and grow. It's the squad, the tribe. That trust and genuineness you don't find very often. I mean that's a shout out to our tribe.

That's really important. You nailed it: everyone's each other's champion. That's what friends should be. A good friend should want you to reach your max potential and help out wherever they can. I want the best for you. If you have friends that are not those friends, it's probably time to move on. You only have so much time in the world; you got to spend it with good peeps.

Aside from the natural answers like 'invest in crypto' or 'I wouldn't have told myself anything because everything made me who I am,' what are some core things the 45-year-old you would have loved to tell the 17-year-old you?

How would you suggest people find that tribe at a young age?

It's hard to even have that thought process when you're that young. You're only thinking of someone else's plan.

I've never heard anyone say that. I love it. It's so true.

You gotta scratch the itch. My daughter today is 24 and at a crossroads. She works for a large accounting firm and isn't necessarily happy. She has the itch to go to Denver. I told her, 'Olivia, do it. You want to experience it because you'd rather go there and know it wasn't right than always wonder 'what if.' What's the worst case scenario? You move back. Nine times out of ten, you appreciate it.

Oh, absolutely. But don't get me wrong, I went through the whole emotional roller coaster. You're trying to build a business and asking yourself, 'Am I doing the right thing?' I don't think someone just falls into something and does it forever. I'm fortunate it's worked out so well, and I absolutely love it. I'm also in a position where, when we talk about retirement, I sell the facade of retirement. Most people I work with, like our tribe, nobody retires. They may exit a business, but they enter into a new one. They redefine what their life and work will be.

There are so many talented people who want to help you build your idea, but you have to go out, put in the work, share the vision, and build the squad. It's all possible, but you don't need to do everything. Outsource the things you're not good at. That's a tough one for a lot of entrepreneurs; it's the control factor. But the reality is that work should go on to somebody else.

Go to LinkedIn. I'm probably the only guy who's going to pitch LinkedIn. I have one of the most active LinkedIn profiles for wealth managers in North America. Go to Stephen Leclair on LinkedIn.

Thank you.