Ready to get inspired.
Today we're taking a deep dive
into the mind of Harley Finkelstein.
Oh, Finkelstein, the president of Shopify.
That's right.
And we're gonna unpack some incredible insights
from his interview on the diary of a CEO.
Sounds fascinating.
I'm always looking for some entrepreneurial wisdom.
Well, get ready because Finkelstein
drops some serious knowledge bombs.
Whether you're a seasoned entrepreneur
or just starting out,
there's something here for everyone.
I like that, breaking it down for all of you.
Yeah, exactly.
And you know what really struck me?
His definition of entrepreneurship.
Okay, how does he define it?
It's all about solving problems.
Solving problems.
Yeah, with the resources you have available,
you know, maximizing your output.
Okay, I'm following you.
So it's not necessarily about having a ton of money
or a perfect business plan.
That's a relief to hear.
All right, it's more about that drive
to find solutions and make things happen.
I think that's a really empowering way to look at it.
Absolutely.
And he even points out how the landscape
of entrepreneurship has changed.
In what way?
Well, the risk is lower than ever before.
Really?
He compares it to the cost of like,
I don't know, a couple of Starbucks lattes.
Wow, so starting a business is as easy as grabbing a coffee.
Not exactly, haha,
but it's definitely more accessible than people think.
I could see that.
It takes some of the pressure off, right?
For sure.
And he backs it up with some pretty solid examples.
Like what?
Things like figs, Jim Shark, all birds.
Oh yeah, I know those.
They all started with an idea, not a fortune.
So it really debunks that myth
of needing a huge investment to get started.
Exactly.
And that brings us to one of Finkelstein's biggest points.
Embracing curiosity and a mindset of constant exploration.
I love that.
It's all about learning and iterating as you go.
Right.
He actually shares how his own entrepreneurial journey
began out of necessity.
Oh, really?
His father went to jail when he was younger.
Wow, that's intense.
And he had to find ways to support his family.
Talk about a crash course in problem solving.
It's a powerful story, right?
It shows how that entrepreneurial drive
can come from different places, not just a passion project.
Totally.
And Finkelstein even connects it
to Richard Branson's famous screw it, just do it.
Right.
Philosophy.
Oh yeah, that's a good one.
There's something to be said for just taking that leap,
especially when you're fueled by passion.
I agree.
But it's not always easy, is it?
Definitely not.
He acknowledges the mental hurdles too,
the self-doubt, the fear of failure.
That's refreshing to hear him talk about those things.
I know, right?
It makes him seem more human, more relatable.
He even talks about the value of therapy, right?
Yeah, he emphasizes the importance of self-awareness,
especially when you're on that entrepreneurial roller coaster.
It could be a wild ride for sure.
So, you know, it's okay to seek support
and guidance along the way.
Absolutely.
Now, speaking of guidance,
he has a pretty interesting take on mentorship.
Oh yeah, his concept of verticals.
That's the one.
So, he's basically saying,
instead of seeking one all-knowing mentor,
you should build a network of advisors
who can offer specialized advice in different areas.
Exactly, like an informal board of directors.
I like that analogy, but it begs the question,
how do you find these mentors?
Right, not everyone has a role,
a dex full of industry giants.
He addresses that.
He emphasizes the value of connecting with peers.
People who are at a similar stage in their journey.
Even if they're in completely different industries.
It's all about building relationships
with people who understand the challenges you're facing.
And can offer support and insights
from their own experiences.
Makes sense.
Now, there's something else I wanted to talk about.
You should.
Finkelstein's investment philosophy.
Oh yeah, he has a great track record
of spotting entrepreneurial potential.
So, he poses this really interesting question
in the interview.
What's the question?
If he had $3 million to invest in three
Shopify entrepreneurs, who would he choose?
Ooh, that's a tough one.
I'm curious to hear his picks.
And his answers reveal a lot
about what he values in a business.
Okay, I'm all ears.
Who are his top three?
His first pick would be a content creator
who's going beyond just selling merch.
Going beyond merch.
Yeah, he's looking for someone who's creating
innovative products that truly serve their audience.
So someone like Kylie Jenner with Kylie Cosmetics.
Exactly, or Mr. Beast with Feastables.
They're leveraging their platforms
to offer something valuable, not just a quick cash grab.
I see, it's about authenticity
and building a real brand.
Right.
Now, his second pick is an entrepreneur
who's laser focused on a specific niche.
Okay, so someone who's really mastered their craft.
Precisely.
He uses the example of James Purse
and his obsession with the perfect black t-shirt.
What's about quality over quantity?
Depths over breadth.
And his third pick is someone who's making
high quality products accessible to a wider market.
Interesting, so democratizing access to quality.
Exactly.
He gives the example of a company
that might create a more affordable version
of a professional microphone.
So aspiring podcasters and musicians
could pursue their passions without breaking the bank.
It's a brilliant strategy.
It speaks to his mission of making entrepreneurship
more inclusive.
And empowering more people to pursue their dreams.
I love that.
Now, throughout the interview,
Finkelstein also talks about the importance
of building a strong company culture.
Culture is crucial.
He even uses this term anti-fragile company.
Yeah, anti-fragile.
It's a really fascinating concept.
He's talking about a company
that doesn't just survive challenges.
It actually thrives because of them.
Right, and this ties back to embracing failure
as a learning opportunity.
An anti-fragile company encourages experimentation
and risk taking.
And they learn from their mistakes.
Which is essential for growth.
Absolutely.
But Finkelstein acknowledges that building
this kind of team isn't easy.
What are some of the challenges?
Well, it's about attracting and retaining
entrepreneurial talent.
People who are naturally curious, ambitious,
and driven to solve problems.
Exactly.
And he stresses the need for genuine connection
in a sense of community.
Which can be tough, especially with so many companies
working remotely these days.
It's something he's grappled with personally.
Oh, really?
He's been open about his struggles with loneliness
during the pandemic.
Even though he was at home with his family.
It's a reminder that even successful entrepreneurs
are human.
They need connection and support, just like everyone else.
He admits that he waited too long
to open up to his wife and colleagues
about what he was going through.
It's easy to get caught up in the hustle
and forget to take care of yourself.
And he frames vulnerability as a magnet for connection.
Not a repellent.
I love that.
It goes against the tough it out mentality
that's often associated with entrepreneurship.
And it aligns with his message of authenticity
and transparency.
He encourages entrepreneurs to be honest
about their struggles, their failures,
and the hard work that goes into building a business.
It's refreshing to hear him debunk
the myth of overnight success.
And acknowledge the messy, iterative journey
that most entrepreneurs experience.
Now, he doesn't just focus on the practical aspects
of entrepreneurship.
He also talks about the emotional and psychological side.
Which is often overlooked.
He's open about his experiences with therapy
and the importance of self-awareness.
Especially in a field that can be so demanding.
He also stresses the importance of work-life balance
and prioritizing the things that truly matter.
Like spending time with family
and taking care of your health.
He actually uses his calendar to schedule these things.
It's a great tip.
Being intentional with your time.
So you're not just caught up in the whirlwind of work.
And neglecting the things that bring you joy
outside of business.
No, Finkelstein's interview is full
of these amazing insights.
And his closing remarks are especially powerful.
He reminds us that the cost of failure
is lower than ever before.
In the entire history of the world.
It's a powerful statement, right?
It is.
It's like he's giving us permission to try,
to experiment, to chase our dreams.
And he's not just talking about it.
He's living it.
Remember, he's running a multi-billion dollar company
while still tinkering with his own side hustles.
Talk about walking the walk.
It really goes to show that the entrepreneurial spirit
can thrive at any level.
And it's never too late to start.
So as we wrap up this part of our deep dive
into Harley Finkelstein's world.
I'm already feeling inspired.
I am too.
And I'm excited to continue unpacking his wisdom
in the next part of our deep dive.
Can't wait.
So it's about more than just launching the next big thing.
Yeah.
It's about supporting entrepreneurs
who are trying to make a positive impact
and create opportunities for others.
And building businesses that can weather any storm.
Oh, right.
He talked about building an anti-fragile company.
Did he explain what he means by that?
He did.
It's a company that doesn't just survive challenges.
It actually gets stronger because of them.
Exactly.
Which goes back to his point about embracing failure.
Seeing it as a learning experience.
It's like building resilience into the DNA of the company.
So how do you actually create an anti-fragile company?
Well, he talks about the importance
of attracting and retaining entrepreneurial talent.
Those folks who are naturally curious and ambitious, right?
Yeah.
And he also emphasizes the importance
of fostering a sense of community.
Which is super important, especially
in the age of remote work.
And it's something he's struggled with personally.
You know?
What do you mean?
He's talked about feeling lonely during the pandemic.
Even though he was at home with his family.
It's a good reminder that even the most successful entrepreneurs
are human.
They need connection and support.
Yeah.
Just like everyone else.
Absolutely.
And he admitted that he waited too long
to open up to his wife and colleagues
about what he was going through.
It's easy to get caught up in the hustle
and forget to take care of yourself.
And he actually frames vulnerability
as a magnet for connection.
Not a repellent.
I thought that was such a powerful statement.
It really goes against the grain of that tough it out
mentality.
Which is so common in the entrepreneurial world.
It's more like embrace your vulnerability
and connect with others.
And it aligns with his overall message of authenticity
and transparency.
He's all about being real, right?
Yeah.
He encourages entrepreneurs to be honest
about their struggles, their failures,
and the hard work that goes into building a successful business.
Because it's not all sunshine and rainbows.
Definitely not.
He really debunks that myth of overnight success.
It's a process.
A journey.
With ups and downs, twists and turns.
And it's important to acknowledge that.
You know, he doesn't just focus on the practical side
of entrepreneurship.
He also delves into the emotional and psychological aspects.
Which can be just as challenging, if not more so.
He's very open about his experiences with therapy.
And the importance of self-awareness.
Especially in such a high pressure environment.
He also stresses the importance of work-life balance.
Making time for things that truly matter.
Like spending time with family, taking care of your health.
These are things we often neglect when we're in hustle mode.
He actually schedules these things in his calendar.
What a great idea.
It's all about being intentional with your time.
And not letting work consume your entire life.
Now Finkelstein's interview is packed
with these amazing insights.
But his closing remarks really stuck with me.
I'm curious.
What did he say?
He said, the cost of failure is lower than ever before.
Wow.
It's such a simple statement, but it's so profound.
What makes it so powerful for you?
It's like he's giving us permission to try.
To experiment.
To chase our dreams.
Without fear of failing.
Because the consequences of failure are not as dire
as they used to be.
Exactly.
And he's not just talking about it.
He's living it.
Running a multi-billion dollar company
and still tinkering with his own side hustles.
Talk about walking the walk.
It just goes to show that the entrepreneurial spirit
can thrive at any level.
And it's never too late to start.
So true.
It's inspiring, isn't it?
Totally.
He's a living example of what he preaches.
Right.
Leading Shopify and still making time for his own projects.
It proves you can be entrepreneurial at any stage.
And that's what I find so encouraging
about Finkelstein's story.
It makes you want to get out there and try something new.
He really does leave us with that feeling.
But he also leaves us with a really thought-provoking
question.
Oh yeah, what was it?
In a world that's so reliant on technology,
how do we as entrepreneurs build genuine human connections?
How do we foster a sense of community?
That's a big one.
Something we all need to be thinking about.
Absolutely.
And as we wrap up this deep dive, I
want to put that question to you directly.
OK, shoot.
What's one small step you can take today, right now,
to turn your hobby into something more?
Or to connect with another entrepreneur who
can support your journey?
It doesn't have to be a huge leap, just a small step forward.
Because remember, the cost of failure
is lower than ever before.
So why not take a chance?
Exactly.
And we'll be here to cheer you on every step of the way.
Until next time.
Keep diving deep and never stop learning.