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

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Episode Transcript

SPEAKER_00 (00:00):
One of the most important things that we can all
learn in life, and pretty mucheverything, but particularly
money, is discipline and makinggood choices.
I have a 13-year-old son, andone of the things that I tell
him all the time, which reallyannoys him, because I say it a
lot, is easy choices, hard life,hard choices, easy life.

SPEAKER_01 (00:46):
And this year's theme is Lift Up Your Future.
It's all about discovering howthe choices we make today, what
we learn, what we explore, andhow we manage money can help
build the kind of future we wanttomorrow.
That connects perfectly totoday's conversation why it's
important to invest early.
My guest today is Seth Cogswell,founder and managing partner at
Running Oak Capital.

(01:07):
Seth helps people grow theirwealth through disciplined
long-term investing.
Let's dig into how young peoplecan start thinking about money,
saving, and building financialhabits that lift up their
future.
Seth, Seth, thanks so much forjoining me.

SPEAKER_00 (01:22):
I appreciate you having me.
Excellent introduction.

SPEAKER_01 (01:26):
Seth, you've mentioned your dad was a big
inspiration for you.
Can you tell me that story andwhat lessons have stuck with
you?

SPEAKER_00 (01:32):
Well, uh, my father was in the industry, so I kind
of grew up seeing what he wasdoing.
And that's often uh, you know,the best way to learn is just
watching others.
And it, I was always really intomath and and numbers.
And so it just seemed prettyinteresting to me.
He had, he used to before thisthis might be hard to wrap your

(01:55):
head around, but when I was yourage, uh, we didn't have
computers.
So he would receive these booksthat had stock charts, you know,
so sort of tracking the price ofthe stocks throughout throughout
time.
And I would steal them when hewasn't looking and look through
them, and you'd see these linesgoing up and down, and I'd be

(02:16):
like, oh, this would have beenso easy to just buy here and
sell here.
Of course, it's not that easy.
It's actually really hard in themoment.
But that kind of got me into it.
And so um once I got to collegeand and had a a few dollars,
I've I started investing ortrading, and I I did a lot of
really dumb things, made a lotof mistakes, but learned from

(02:40):
them and and yeah, realized Iliked it even more than I
thought and and worked hard atit, and then uh, you know, ended
up going that way from mycareer.
But uh, you know, I realizedthat my father created something
that was that was very valuable,and he didn't necessarily all
have different things that we'regood at.

(03:00):
Uh generally speaking, nobody'sgood at everything.
And so with businesses, you'lloften see a couple people
partner, maybe where someone'sreally good at uh you know
creating something, whereassomeone else is really good
about communicating it.
And and so my my father didn'tnecessarily have the skill set

(03:20):
to communicate what he hadcreated.
And so I decided that thatshould probably be my job.
And so I I started the companyand just doing whatever I can to
kind of share what it is he'screated and how I can help
people.

SPEAKER_01 (03:35):
That's amazing.
Um, for someone my age, why doesstarting early matter so much
when it comes to investing andbuilding wealth?

SPEAKER_00 (03:42):
There is a phrase which I I'm sure I will mess up
because I don't know if I'veever said it before, but uh
compound interests orcompounding as the, let's say,
the eighth wonder of the world.
And the idea is that um, youknow, if if you have a dollar
today and then you invest it andthen you earn 10%, the next year
is worth a dollar ten.

(04:03):
And then two years from now,it's worth a dollar twenty-one.
And it it just and it so itadded 10 cents the first year,
it added 11 cents the secondyear, and that'll just keep
going.
And if you keep investing moreand more, also that just adds
up.
And in time is one of the keyparts of it, right?
So each year it's it's growing.

(04:24):
And so starting early and anddoing that just helps you get
ahead of most people.
I didn't really have much ummoney 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 itmakes time kind of your your
tool.

SPEAKER_01 (04:45):
And I'm curious, what's one lesson you've learned
in your career that you thinkevery teenager should know about
money?

SPEAKER_00 (04:51):
I I mean, really, I'd say the main thing is going
back to what I just said, moneyis nothing more than a tool.
Um, a lot of people prioritizemoney over other things in life
when really money is just a wayfor us to pay for the the things
that we both need and we want inlife.

(05:13):
Um, and so really thinking of itin that way and not making it
more important than it is, butalso realizing that it it'll
help help you do the things thatyou want.
So it does matter.
Um, and and kind of going backto the prior question, and and I

(05:35):
guess this one is one of themost important things that we
can all learn in life, andpretty much everything, but
particularly money, isdiscipline and making good
choices.
I have a 13-year-old son, andone of the things that I tell
him all the time, which reallyannoys him because I say it a
lot, is easy choices, hard life,hard choices, easy life.

(05:59):
So at any given moment, you havea bunch of choices available to
you.
So if we're talking about money,right?
You walk into a store and youyou see, I don't know, let's say
you see a video game that you'dlove.
And so you could spend$50 onthat now.
But again, going back to thatcompound interest, if you save
that$50, it it'll be worth$55next year.

(06:23):
And then 10 years from now,maybe it's worth, I don't know,
let's say$500, right?
And so that discipline andreally thinking about
prioritizing both what you wanttoday versus what you want
tomorrow or a few years from nowis an important decision to
constantly think about.
Um maybe you want that videogame today.

(06:45):
Awesome.
Like if you have the money andyou will get a lot out of it, go
for it.
But it's just knowing that ifyou save, it could be worth$500,
you know, a few years from now.
So it's just really thinkingabout what it is that you want
and having the discipline tomake the decision that you feel
is best.

SPEAKER_01 (07:04):
That's great.
And if a student wants to startlearning about investing now,
what's one simple practical stepthey can take?

SPEAKER_00 (07:10):
You know, the one of the great things about the
internet is is all of theinformation basically in the
world is at your fingertips.
And then, you know, with with AIbecoming more popular, it makes
it even easier to find.
And and so I'd say read.
Uh there's there's no better wayto learn than from the lives of

(07:35):
others who've done it beforeyou, because then you don't have
to make those mistakes.
You let other people makemistakes and do their own dumb
things, and then you can belike, oh, well, now I don't have
to do those dumb things.
I can I don't have to make thosemistakes.
So to whatever extent you canlearn from others, which again,
reading is by far the best wayto do it.
Umbrace that and learn as muchas you possibly can because it's

(07:59):
there it's all available to you.

SPEAKER_01 (08:01):
And finally, how do you think young people can lift
up their futures, not justthrough school or careers, but
by doing other things to buildconfidence and independence?

SPEAKER_00 (08:11):
I I again I have three children, and one of the
things that I battle regularlyis technology.
Um, so whether it's phones,laptops, or iPads, whatever it
is, it's very easy for thosethings to just vacuum up your
time and and take and just be amassive waste.

(08:32):
So you you could be using timeto grow, to get healthier, to do
lots of things.
Instead, all of us, includingadults, tend to get sucked into
things that aren't that they'renot only not helping us, they're
actually hurting us, such asstaring at the phone, staring at
whatever.
Nothing matters more than beingable to interact with people,

(08:58):
whether it's being friends orlearning how to deal with people
who aren't friends.
Um, and so you know, reallyfocusing on communication, uh
being outside as much aspossible, reading as much as
possible.
I'm a I believe you're inCanada.
Um, so I'm hoping Canadians aremuch smarter than Americans.

(09:20):
But the average American readszero books a year right now.
Zero.
And again, there's no better wayto learn than from the lessons
of others.
Uh and so again, reading.
That's that's probably thenumber one thing to make your
life better.

SPEAKER_01 (09:38):
Thanks so much for joining me today.
I really appreciate your timeand insights.
And thanks to everyone watchingthis special lift up your future
edition of Lead Lag Live.
Be sure to like, follow, andsubscribe for more episodes.
I'm Metch at Risky.
See you next time.