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Comment “SHOPIFY” for a link to this episode! Shopify President Harley Finkelstein (@harley) explains why the most successful modern brands are no longer just selling products. Founders like Sara and Erin Foster of Favorite Daughter (@favorite.daughter) are building worlds people want to be part of, where media, retail, entertainment, storytelling, and community all work together to create culture 🦄.

This episode is live everywhere you get your podcasts! 👀

The best cold email I ever sent had nothing to do with me.

Most people pitch by talking about themselves. What they built. Why it matters. Why you should care.

That’s just another email in the inbox.

Want someone’s attention? Lead with what they want. Not what you want.

@shopify just reported on Q1 and the numbers speak for themselves.

$101 billion in merchant sales. The second consecutive quarter our merchants crossed $100 billion. Four straight quarters of 30%+ growth. At a scale where Shopify now represents over 14% of US ecommerce.

Behind those numbers is something that’s hard to replicate. Twenty years of commerce data. Millions of merchants, billions of transactions. All of it now powering AI tools, new shopping channels, and the next generation of billion-dollar brands. That advantage only compounds from here.

The highlights:
→ $101B in merchant sales, up 35% YoY
→ $3.2B revenue, up 34% YoY
→ $476M free cash flow, 15% margin
→ Sidekick usage up 4x YoY
→ Orders from AI-powered searches up nearly 13x
→ Merchants now selling inside ChatGPT, Copilot, and Google
→ @Shop Pay GMV up 59% YoY
→ Iconic brands across fashion, luxury, and retail all joined this quarter

No job will be more accelerated by AI than entrepreneurship. More entrepreneurs means more people who need Shopify.

Two words separate people who build things from people who just think about it.

What if.

“What if” keeps people stuck. “Why not” builds empires.

Lew Wolff built a real estate empire, owned 2 different sports franchises, and made deals most people wouldn’t dream of. And it started with one shift, from fear to curiosity.

Every setback gave him something. A lesson, an edge, a better way forward. That’s not failure. That’s fuel.

If you’re sitting on an idea right now, paralyzed by “what if” think “why not.”

He owned the A’s. The Warriors. Built cities.
But his real edge? You’d never see it coming.

Lew Wolff didn’t win by being the loudest in the room. He won by playing a completely different game.

In this episode, you’ll learn:
• Why not being attached to outcomes can become your biggest advantage
• How partnerships (and sharing success) actually create more wealth
• The power of “shadow + substance” to open doors most people can’t
• Why kindness, patience, and long-term relationships quietly outperform aggression

From a Midwest kid to owning major franchises—this is a masterclass in a different kind of ambition.

Watch the full episode with the link in our bio.

#billionairemindset #entreprenuer #chutzpah #jewishpride

🎙️OUT NOW

Shopify president Harley Finkelstein wasn’t always outspoken. Now? He’s one of the loudest Jewish voices in Canada. So what changed? 🤔

In this conversation with Jonah Platt, we dive deep:
• From Holocaust survival → building Shopify
• Losing everything after 9/11
• Why “flying under the radar” no longer works
• And the responsibility of Jewish leaders right now

Plus — his 93-year-old grandparents, still in love after everything ❤️

This isn’t just business. It’s identity. It’s resilience. It’s now.

⚡️Stream NOW on Being Jewish with Jonah Platt website, YouTube, Apple Pods and Spotify.

The best founders don’t guess what their customers want. They already know. Because they’re paying attention every single day.

@rhode put a lip balm slot in a phone case.

That’s not just product innovation. That’s audience empathy. @haileybieber and her team are so locked into their community they knew exactly what their customers would use every day.

That’s the difference between a good brand and a great one.

He started with $1,800 from his father…
and built one of the largest apparel empires in North America, turning Montreal’s Chabanel district into a hub of global fashion.

Joseph Schaffer is almost 105 years old and his mindset is sharper than most founders today.

This episode is full of old-school wisdom that still wins:
• “Be honest. That’s what gets you somewhere.”
• Why he gave partners equity (and never fired one)
• How he built trust with banks before he ever had money
• And the philosophy that made everyone around him rich

This isn’t just a business story. It’s a masterclass in trust, partnership, and playing the long game.

Joseph puts it best by saying, “Honesty is the best policy.”

Watch the full episode with the link in our bio.

#billionairemindset #entrepreneurship #chutzpah #jewishpride

Failure matters less than how you respond to it.

In the gym, failure isn’t a problem. It’s the whole program. The rep you can’t finish is the one that makes you stronger.

Nobody quits the gym because they couldn’t finish a set. But in business, people treat failure like a stop sign.

It’s not. It’s the signal to keep going.

Shabbat Shalom friends,

I recorded a very special (and very personal!) @bigshotshow episode with my grandparents. My Bubby and Zadie, who are in their 90s.

I’m not sharing the full episode. I really made it for my family, especially my children.

But I wanted to share a few moments from our conversation.

They’re not famous entrepreneurs. But everything I know about hard work, love, relationships, and living a life of purpose, I learned from them.

They are my role models for life.

Shabbat Shalom friends,

I recorded a very special (and very personal!) @bigshotshow episode with my grandparents. My Bubby and Zadie, who are in their 90s.

I’m not sharing the full episode. I really made it for my family, especially my children.

But I wanted to share a few moments from our conversation.

They’re not famous entrepreneurs. But everything I know about hard work, love, relationships, and living a life of purpose, I learned from them.

They are my role models for life.

Shabbat Shalom friends,

I recorded a very special (and very personal!) @bigshotshow episode with my grandparents. My Bubby and Zadie, who are in their 90s.

I’m not sharing the full episode. I really made it for my family, especially my children.

But I wanted to share a few moments from our conversation.

They’re not famous entrepreneurs. But everything I know about hard work, love, relationships, and living a life of purpose, I learned from them.

They are my role models for life.

Shabbat Shalom friends,

I recorded a very special (and very personal!) @bigshotshow episode with my grandparents. My Bubby and Zadie, who are in their 90s.

I’m not sharing the full episode. I really made it for my family, especially my children.

But I wanted to share a few moments from our conversation.

They’re not famous entrepreneurs. But everything I know about hard work, love, relationships, and living a life of purpose, I learned from them.

They are my role models for life.

Add this to must-watch list 💌

Have you ever wondered who powers your favourite brands? 👀

Today on @hotsmartrich we have the President of Shopify @harley

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, this episode is packed with all the juicy nuggets of insider gossip.

Comment ‘HSR’ and we’ll send you the full episode ❤️

Add this to must-watch list 💌

Have you ever wondered who powers your favourite brands? 👀

Today on @hotsmartrich we have the President of Shopify @harley

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, this episode is packed with all the juicy nuggets of insider gossip.

Comment ‘HSR’ and we’ll send you the full episode ❤️

Add this to must-watch list 💌

Have you ever wondered who powers your favourite brands? 👀

Today on @hotsmartrich we have the President of Shopify @harley

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, this episode is packed with all the juicy nuggets of insider gossip.

Comment ‘HSR’ and we’ll send you the full episode ❤️

Add this to must-watch list 💌

Have you ever wondered who powers your favourite brands? 👀

Today on @hotsmartrich we have the President of Shopify @harley

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, this episode is packed with all the juicy nuggets of insider gossip.

Comment ‘HSR’ and we’ll send you the full episode ❤️

Add this to must-watch list 💌

Have you ever wondered who powers your favourite brands? 👀

Today on @hotsmartrich we have the President of Shopify @harley

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, this episode is packed with all the juicy nuggets of insider gossip.

Comment ‘HSR’ and we’ll send you the full episode ❤️

Add this to must-watch list 💌

Have you ever wondered who powers your favourite brands? 👀

Today on @hotsmartrich we have the President of Shopify @harley

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, this episode is packed with all the juicy nuggets of insider gossip.

Comment ‘HSR’ and we’ll send you the full episode ❤️

Comment ‘HSR’ and we’ll send you this entire conversation.

50 years ago becoming an entrepreneur meant risking everything, but today because of platforms like Shopify, you can become an entrepreneur with less than $100, and a whole lot of grit.

We sat down with the President of Shopify @harley to get the tea on what the most successful brands are doing right now and what we can learn from them.

Here’s everything we cover:

💸 How Rhode keeps consistently killing it right now. What’s their secret?

💸 The non-negotiable personality trait every entrepreneur needs to succeed

💸 Why Kylie Cosmetics has more longevity than standard beauty brands

💸 Does your friend group decide if you will be an entrepreneur

Whether you’re an aspiring entrepreneur or obsessed with consumer brands, you need to listen to this episode.

This is your chance to learn from the President of a $150 billion company that is spearheading the creator economy.

Harley Finkelstein, are you ready to get Hot Smart Rich?