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Ready to get inspired.

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Today we're taking a deep dive

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into the mind of Harley Finkelstein.

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Oh, Finkelstein, the president of Shopify.

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That's right.

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And we're gonna unpack some incredible insights

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from his interview on the diary of a CEO.

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Sounds fascinating.

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I'm always looking for some entrepreneurial wisdom.

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Well, get ready because Finkelstein

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drops some serious knowledge bombs.

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Whether you're a seasoned entrepreneur

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or just starting out,

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there's something here for everyone.

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I like that, breaking it down for all of you.

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Yeah, exactly.

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And you know what really struck me?

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His definition of entrepreneurship.

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Okay, how does he define it?

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It's all about solving problems.

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Solving problems.

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Yeah, with the resources you have available,

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you know, maximizing your output.

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Okay, I'm following you.

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So it's not necessarily about having a ton of money

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or a perfect business plan.

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That's a relief to hear.

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All right, it's more about that drive

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to find solutions and make things happen.

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I think that's a really empowering way to look at it.

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Absolutely.

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And he even points out how the landscape

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of entrepreneurship has changed.

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In what way?

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Well, the risk is lower than ever before.

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Really?

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He compares it to the cost of like,

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I don't know, a couple of Starbucks lattes.

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Wow, so starting a business is as easy as grabbing a coffee.

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Not exactly, haha,

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but it's definitely more accessible than people think.

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I could see that.

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It takes some of the pressure off, right?

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For sure.

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And he backs it up with some pretty solid examples.

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Like what?

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Things like figs, Jim Shark, all birds.

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Oh yeah, I know those.

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They all started with an idea, not a fortune.

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So it really debunks that myth

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of needing a huge investment to get started.

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Exactly.

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And that brings us to one of Finkelstein's biggest points.

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Embracing curiosity and a mindset of constant exploration.

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I love that.

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It's all about learning and iterating as you go.

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Right.

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He actually shares how his own entrepreneurial journey

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began out of necessity.

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Oh, really?

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His father went to jail when he was younger.

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Wow, that's intense.

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And he had to find ways to support his family.

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Talk about a crash course in problem solving.

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It's a powerful story, right?

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It shows how that entrepreneurial drive

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can come from different places, not just a passion project.

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Totally.

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And Finkelstein even connects it

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to Richard Branson's famous screw it, just do it.

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Right.

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Philosophy.

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Oh yeah, that's a good one.

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There's something to be said for just taking that leap,

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especially when you're fueled by passion.

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I agree.

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But it's not always easy, is it?

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Definitely not.

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He acknowledges the mental hurdles too,

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the self-doubt, the fear of failure.

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That's refreshing to hear him talk about those things.

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I know, right?

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It makes him seem more human, more relatable.

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He even talks about the value of therapy, right?

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Yeah, he emphasizes the importance of self-awareness,

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especially when you're on that entrepreneurial roller coaster.

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It could be a wild ride for sure.

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So, you know, it's okay to seek support

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and guidance along the way.

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Absolutely.

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Now, speaking of guidance,

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he has a pretty interesting take on mentorship.

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Oh yeah, his concept of verticals.

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That's the one.

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So, he's basically saying,

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instead of seeking one all-knowing mentor,

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you should build a network of advisors

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who can offer specialized advice in different areas.

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Exactly, like an informal board of directors.

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I like that analogy, but it begs the question,

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how do you find these mentors?

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Right, not everyone has a role,

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a dex full of industry giants.

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He addresses that.

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He emphasizes the value of connecting with peers.

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People who are at a similar stage in their journey.

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Even if they're in completely different industries.

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It's all about building relationships

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with people who understand the challenges you're facing.

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And can offer support and insights

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from their own experiences.

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Makes sense.

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Now, there's something else I wanted to talk about.

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You should.

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Finkelstein's investment philosophy.

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Oh yeah, he has a great track record

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of spotting entrepreneurial potential.

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So, he poses this really interesting question

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in the interview.

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What's the question?

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If he had $3 million to invest in three

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Shopify entrepreneurs, who would he choose?

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Ooh, that's a tough one.

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I'm curious to hear his picks.

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And his answers reveal a lot

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about what he values in a business.

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Okay, I'm all ears.

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Who are his top three?

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His first pick would be a content creator

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who's going beyond just selling merch.

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Going beyond merch.

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Yeah, he's looking for someone who's creating

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innovative products that truly serve their audience.

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So someone like Kylie Jenner with Kylie Cosmetics.

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Exactly, or Mr. Beast with Feastables.

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They're leveraging their platforms

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to offer something valuable, not just a quick cash grab.

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I see, it's about authenticity

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and building a real brand.

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Right.

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Now, his second pick is an entrepreneur

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who's laser focused on a specific niche.

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Okay, so someone who's really mastered their craft.

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Precisely.

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He uses the example of James Purse

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and his obsession with the perfect black t-shirt.

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What's about quality over quantity?

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Depths over breadth.

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And his third pick is someone who's making

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high quality products accessible to a wider market.

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Interesting, so democratizing access to quality.

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Exactly.

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He gives the example of a company

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that might create a more affordable version

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of a professional microphone.

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So aspiring podcasters and musicians

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could pursue their passions without breaking the bank.

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It's a brilliant strategy.

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It speaks to his mission of making entrepreneurship

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more inclusive.

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And empowering more people to pursue their dreams.

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I love that.

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Now, throughout the interview,

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Finkelstein also talks about the importance

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of building a strong company culture.

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Culture is crucial.

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He even uses this term anti-fragile company.

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Yeah, anti-fragile.

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It's a really fascinating concept.

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He's talking about a company

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that doesn't just survive challenges.

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It actually thrives because of them.

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Right, and this ties back to embracing failure

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as a learning opportunity.

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An anti-fragile company encourages experimentation

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and risk taking.

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And they learn from their mistakes.

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Which is essential for growth.

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Absolutely.

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But Finkelstein acknowledges that building

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this kind of team isn't easy.

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What are some of the challenges?

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Well, it's about attracting and retaining

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entrepreneurial talent.

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People who are naturally curious, ambitious,

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and driven to solve problems.

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Exactly.

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And he stresses the need for genuine connection

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in a sense of community.

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Which can be tough, especially with so many companies

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working remotely these days.

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It's something he's grappled with personally.

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Oh, really?

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He's been open about his struggles with loneliness

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during the pandemic.

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Even though he was at home with his family.

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It's a reminder that even successful entrepreneurs

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are human.

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They need connection and support, just like everyone else.

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He admits that he waited too long

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to open up to his wife and colleagues

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about what he was going through.

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It's easy to get caught up in the hustle

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and forget to take care of yourself.

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And he frames vulnerability as a magnet for connection.

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Not a repellent.

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I love that.

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It goes against the tough it out mentality

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that's often associated with entrepreneurship.

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And it aligns with his message of authenticity

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and transparency.

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He encourages entrepreneurs to be honest

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about their struggles, their failures,

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and the hard work that goes into building a business.

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It's refreshing to hear him debunk

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the myth of overnight success.

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And acknowledge the messy, iterative journey

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that most entrepreneurs experience.

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Now, he doesn't just focus on the practical aspects

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of entrepreneurship.

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He also talks about the emotional and psychological side.

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Which is often overlooked.

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He's open about his experiences with therapy

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and the importance of self-awareness.

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Especially in a field that can be so demanding.

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He also stresses the importance of work-life balance

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and prioritizing the things that truly matter.

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Like spending time with family

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and taking care of your health.

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He actually uses his calendar to schedule these things.

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It's a great tip.

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Being intentional with your time.

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So you're not just caught up in the whirlwind of work.

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And neglecting the things that bring you joy

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outside of business.

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No, Finkelstein's interview is full

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of these amazing insights.

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And his closing remarks are especially powerful.

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He reminds us that the cost of failure

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is lower than ever before.

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In the entire history of the world.

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It's a powerful statement, right?

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It is.

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It's like he's giving us permission to try,

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to experiment, to chase our dreams.

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And he's not just talking about it.

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He's living it.

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Remember, he's running a multi-billion dollar company

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while still tinkering with his own side hustles.

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Talk about walking the walk.

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It really goes to show that the entrepreneurial spirit

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can thrive at any level.

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And it's never too late to start.

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So as we wrap up this part of our deep dive

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into Harley Finkelstein's world.

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I'm already feeling inspired.

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I am too.

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And I'm excited to continue unpacking his wisdom

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in the next part of our deep dive.

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Can't wait.

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So it's about more than just launching the next big thing.

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Yeah.

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It's about supporting entrepreneurs

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who are trying to make a positive impact

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and create opportunities for others.

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And building businesses that can weather any storm.

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Oh, right.

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He talked about building an anti-fragile company.

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Did he explain what he means by that?

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He did.

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It's a company that doesn't just survive challenges.

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It actually gets stronger because of them.

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Exactly.

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Which goes back to his point about embracing failure.

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Seeing it as a learning experience.

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It's like building resilience into the DNA of the company.

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So how do you actually create an anti-fragile company?

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Well, he talks about the importance

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of attracting and retaining entrepreneurial talent.

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Those folks who are naturally curious and ambitious, right?

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Yeah.

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And he also emphasizes the importance

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of fostering a sense of community.

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Which is super important, especially

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in the age of remote work.

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And it's something he's struggled with personally.

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You know?

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What do you mean?

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He's talked about feeling lonely during the pandemic.

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Even though he was at home with his family.

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It's a good reminder that even the most successful entrepreneurs

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are human.

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They need connection and support.

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Yeah.

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Just like everyone else.

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Absolutely.

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And he admitted that he waited too long

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to open up to his wife and colleagues

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about what he was going through.

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It's easy to get caught up in the hustle

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and forget to take care of yourself.

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And he actually frames vulnerability

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as a magnet for connection.

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Not a repellent.

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I thought that was such a powerful statement.

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It really goes against the grain of that tough it out

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mentality.

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Which is so common in the entrepreneurial world.

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It's more like embrace your vulnerability

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and connect with others.

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And it aligns with his overall message of authenticity

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and transparency.

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He's all about being real, right?

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Yeah.

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He encourages entrepreneurs to be honest

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about their struggles, their failures,

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and the hard work that goes into building a successful business.

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Because it's not all sunshine and rainbows.

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Definitely not.

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He really debunks that myth of overnight success.

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It's a process.

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A journey.

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With ups and downs, twists and turns.

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And it's important to acknowledge that.

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You know, he doesn't just focus on the practical side

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of entrepreneurship.

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He also delves into the emotional and psychological aspects.

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Which can be just as challenging, if not more so.

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He's very open about his experiences with therapy.

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And the importance of self-awareness.

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Especially in such a high pressure environment.

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He also stresses the importance of work-life balance.

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Making time for things that truly matter.

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Like spending time with family, taking care of your health.

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These are things we often neglect when we're in hustle mode.

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He actually schedules these things in his calendar.

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What a great idea.

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It's all about being intentional with your time.

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And not letting work consume your entire life.

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Now Finkelstein's interview is packed

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with these amazing insights.

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But his closing remarks really stuck with me.

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I'm curious.

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What did he say?

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He said, the cost of failure is lower than ever before.

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Wow.

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It's such a simple statement, but it's so profound.

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What makes it so powerful for you?

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It's like he's giving us permission to try.

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To experiment.

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To chase our dreams.

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Without fear of failing.

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Because the consequences of failure are not as dire

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as they used to be.

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Exactly.

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And he's not just talking about it.

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He's living it.

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Running a multi-billion dollar company

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and still tinkering with his own side hustles.

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Talk about walking the walk.

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It just goes to show that the entrepreneurial spirit

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can thrive at any level.

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And it's never too late to start.

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So true.

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It's inspiring, isn't it?

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Totally.

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He's a living example of what he preaches.

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Right.

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Leading Shopify and still making time for his own projects.

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It proves you can be entrepreneurial at any stage.

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And that's what I find so encouraging

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about Finkelstein's story.

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It makes you want to get out there and try something new.

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He really does leave us with that feeling.

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But he also leaves us with a really thought-provoking

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question.

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Oh yeah, what was it?

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In a world that's so reliant on technology,

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how do we as entrepreneurs build genuine human connections?

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How do we foster a sense of community?

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That's a big one.

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Something we all need to be thinking about.

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Absolutely.

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And as we wrap up this deep dive, I

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want to put that question to you directly.

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OK, shoot.

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What's one small step you can take today, right now,

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to turn your hobby into something more?

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Or to connect with another entrepreneur who

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can support your journey?

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It doesn't have to be a huge leap, just a small step forward.

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Because remember, the cost of failure

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is lower than ever before.

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So why not take a chance?

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Exactly.

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And we'll be here to cheer you on every step of the way.

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Until next time.

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Keep diving deep and never stop learning.