Lift Up Your Future: Seth Cogswell on Starting Early, Discipline, and Building Wealth That Lasts

In this special Take Your Kid to Work Day edition of Lead-Lag Live, Grade 9 student Ezra Briski steps in as host to explore this year’s theme: Lift Up Your Future — how the choices we make today shape the opportunities we have tomorrow. Ezra sits down with Seth Cogswell, Founder and Managing Partner at Running Oak Capital, to discuss why starting early with money and investing can change your entire life’s trajectory.

In this episode, Seth shares:
– Why compounding is like a superpower for people who start young
– The lesson: “Easy choices, hard life. Hard choices, easy life.”
– How to think of money as a tool, not something to chase
– Why discipline matters more than picking the perfect stock
– How to avoid “today’s impulse” stealing “tomorrow’s possibilities”
– Why reading and learning from others is the cheat code to growing faster
– The importance of minimizing distractions and building real-world confidence

This episode is about building habits, not hype.
It’s about learning to value your future self — and taking steps now that make life easier later.

Lead-Lag Live brings you inside conversations with the financial thinkers who shape markets. Subscribe for interviews that go deeper than the noise.

#LeadLagLive #SethCogswell #RunningOak #FinancialLiteracy #InvestingYoung #CompoundInterest #Discipline #LiftUpYourFuture #TakeYourKidToWorkDay

Transcript

SPEAKER_00 0:00

One of the most important things that we can all learn in life, and pretty much everything, but particularly money, is discipline and making good choices. I have a 13-year-old son, and one of the things that I tell him all the time, which really annoys him, because I say it a lot, is easy choices, hard life, hard choices, easy life.

Discipline And Money Choices

SPEAKER_01 0:46

And this year's theme is Lift Up Your Future. It's all about discovering how the choices we make today, what we learn, what we explore, and how we manage money can help build the kind of future we want tomorrow. That connects perfectly to today's conversation why it's important to invest early. My guest today is Seth Cogswell, founder and managing partner at Running Oak Capital. Seth helps people grow their wealth through disciplined long-term investing. Let's dig into how young people can start thinking about money, saving, and building financial habits that lift up their future. Seth, Seth, thanks so much for joining me.

Lift Up Your Future Theme

SPEAKER_00 1:22

I appreciate you having me. Excellent introduction.

SPEAKER_01 1:26

Seth, you've mentioned your dad was a big inspiration for you. Can you tell me that story and what lessons have stuck with you?

SPEAKER_00 1:32

Well, uh, my father was in the industry, so I kind of grew up seeing what

Why Invest Early

SPEAKER_00 1:38

he was doing. And that's often uh, you know, the best way to learn is just watching others. And it, I was always really into math and and numbers. And so it just seemed pretty interesting to me. He had, he used to before this this might be hard to wrap your head around, but when I was

Seth’s Origin And Lessons From Dad

SPEAKER_00 1:58

your age, uh, we didn't have computers. So he would receive these books that had stock charts, you know, so sort of tracking the price of the stocks throughout throughout time. And I would steal them when he wasn't looking and look through them, and you'd see these lines going up and down, and I'd be like, oh, this would have been so easy to just buy here and sell here. Of course, it's not that easy. It's actually really hard in the moment. But that kind of got me into it. And so um once I got to college and and had a a few dollars, I've I started investing or trading, and I I did a lot of really dumb things, made a lot of mistakes, but learned from them and and yeah, realized I liked it even more than I thought and and worked hard at it, and then uh, you know, ended up going that way from my career. But uh, you know, I realized that my father created something that was that was very valuable, and he didn't necessarily all have different things that we're good at. Uh generally speaking, nobody's good at everything. And so with businesses, you'll often see a couple people partner, maybe where someone's really good at uh you know creating something, whereas someone else is really good about communicating it. And and so my my father didn't necessarily have the skill set to communicate what he had created. And so I decided that that should probably be my job. And so I I started the company and just doing whatever I can to kind of share what it is he's created and how I can help people.

SPEAKER_01 3:35

That's amazing. Um, for someone my age, why does starting early matter so much when it comes to investing and building wealth?

SPEAKER_00 3:42

There is a phrase which I I'm sure I will mess up because I don't know if I've ever said it before, but uh compound interests or compounding as the, let's say, the eighth wonder of the world. And the idea is that um, you know, if if you have a dollar today and then you invest it and then you earn 10%, the next year is worth a dollar ten. And then two years from now, it's worth a dollar twenty-one. And it it just and it so it added 10 cents the first year, it added 11

Compounding Explained Simply

SPEAKER_00 4:12

cents the second year, and that'll just keep going. And if you keep investing more and more, also that just adds up. And in time is one of the key parts of it, right? So each year it's it's growing. And so starting early and and doing that just helps you get ahead of most people. I didn't really have much um money saved up, so I'd say I'm a little behind. Luckily, I'm catching up today, but you know, starting early is a great idea because it it it makes time kind of your your tool.

SPEAKER_01 4:45

And I'm curious, what's one lesson you've learned in your career that you think every teenager should know about money?

SPEAKER_00 4:51

I I mean, really, I'd say the main thing is going back to what I just said, money is nothing more than a tool. Um, a lot of people prioritize money over other things in life when really money is just a way for us to pay for the the things that we both need and we want in life. Um, and so really thinking of it in that way and not making it more important than it is, but also realizing that it it'll help help you do the things that you want. So it does matter. Um, and and kind of going back to the prior question, and and I guess this one is one of the most important things that we can all learn in life, and pretty much everything, but particularly money, is discipline and making good choices. I have a 13-year-old son, and one of the things that I tell him all the time, which really annoys him because I say it a lot, is easy choices, hard life, hard choices, easy life. So at any given moment, you have a bunch of choices available to you. So

Money As A Tool And Tradeoffs

SPEAKER_00 6:04

if we're talking about money, right? You walk into a store and you you see, I don't know, let's say you see a video game that you'd love. And so you could spend $50 on that now. But again, going back to that compound interest, if you save that $50, it it'll be worth $55 next year. And then 10 years from now, maybe it's worth, I don't know, let's say $500, right? And so that discipline and really thinking about prioritizing both what you want today versus what you want tomorrow or a few years from now is an important decision to constantly think about. Um maybe you want that video game today. Awesome. Like if you have the money and you will get a lot out of it, go for it. But it's just knowing that if you save, it could be worth $500, you know, a few years from now. So it's just really thinking about what it is that you want and having the discipline to make the decision that you feel is best.

SPEAKER_01 7:04

That's great. And if a student wants to start learning about investing now, what's one simple practical step they can take?

SPEAKER_00 7:10

You know, the one of the great things about the internet is is all of the information basically in the world is at your fingertips. And then, you know, with with AI becoming more popular, it makes it even easier to find. And and so I'd say read. Uh there's there's no better way to learn than from the lives of others who've done it before you, because then you don't have to make those mistakes. You let other people make mistakes

Practical First Steps: Read And Learn

SPEAKER_00 7:41

and do their own dumb things, and then you can be like, oh, well, now I don't have to do those dumb things. I can I don't have to make those mistakes. So to whatever extent you can learn from others, which again, reading is by far the best way to do it. Umbrace that and learn as much as you possibly can because it's there it's all available to you.

SPEAKER_01 8:01

And finally, how do you think young people can lift up their futures, not just through school or careers, but by doing other things to build confidence and independence?

SPEAKER_00 8:11

I I again I have three children, and one of the things that I battle regularly is technology. Um, so whether it's phones, laptops, or iPads, whatever it is, it's very easy for those things to just vacuum up your time and and take and just be a massive waste. So you you could be using time to grow, to get healthier, to do lots of things. Instead, all of us, including adults, tend to get sucked into things that aren't that they're not only not helping

Build Confidence Beyond Screens

SPEAKER_00 8:47

us, they're actually hurting us, such as staring at the phone, staring at whatever. Nothing matters more than being able to interact with people, whether it's being friends or learning how to deal with people who aren't friends. Um, and so you know, really focusing on communication, uh being outside as much as possible, reading as much as possible. I'm a I believe you're in Canada. Um, so I'm hoping Canadians are much smarter than Americans. But the average American reads zero books a year right now. Zero. And again, there's no better way to learn than from the lessons of others. Uh and so again, reading. That's that's probably the number one thing to make your life better.

SPEAKER_01 9:38

Thanks so much for joining me today. I really appreciate your time and insights. And thanks to everyone watching this special lift up your future edition of Lead Lag Live. Be sure to like, follow, and subscribe for more episodes. I'm Metch at Risky. See you next time.