“This episode was So good!! Loved Harley’s advice about building to solve problems.” - HSR Angel

ICYMI

Hi HSR!!

It’s the final week of our honeymoon and I’ll be back in LA soon! Honestly, I was anxious going into this trip, which now feels crazy to say because it ended up being exactly what I needed after probably the six most stressful months of my life. Pressure is a privilege, yes. But so is knowing when you need to reset.

I’ve also been back on my French grind, which is always humbling. One angel made me laugh so hard this week when she said, “Wait, are you the girl that said ‘regular lait’?” And yes. That was me. And yes, I’m still out here giving it 110% every time I’m in a French-speaking country trying to become bilingual.

This week on the podcast, I had Harley Finkelstein, President of Shopify, on, and honestly, so much of what he said sums up who I am to a tee and how much I’ve always believed in HSR. A lot of people talk about entrepreneurship like it’s some elite club or personality trait you either have or you don’t. I just don’t see it that way. Harley talked about the nine-person rule: spend time with nine entrepreneurs and you’ll be the tenth. The opposite is also true, obviously. If you are surrounded by people who are pulling you away from your goals, your standards will start matching theirs too.

He also said something that really stayed with me: even as the president of Shopify, he is still getting rejected by people he wants to meet with. A man running a $155 billion company is still hearing no. Which is such an important reminder because I got really vulnerable in this episode too and shared that before I moved to the U.S., I applied to Shopify HQ in Toronto 11 times. Eleven. Rejected 11 times. And I still never stopped. I never let myself get discouraged enough to quit on the bigger vision.

That’s probably the thing I keep coming back to most right now. What would you do differently if you knew you were just 11 rejections away from the meeting, the job, the life, the company, the version of yourself you actually want? The cost of failure is so low now. Embarrassment is not death. Rejection is not death. So why not just try?

A few of my favorite takeaways from the episode:

I also thought a lot about some people I still really want to meet, just because I’m genuinely fascinated by how they think and operate. Starting with Cait Bailey, who I find one of the most interesting women in business full stop. Then Natalie Massenet, founder of Net-A-Porter and Imaginary Ventures, because founder to investor pipeline women will always do it for me. And Paige DeSorbo, because people tell me I’m funniest when I’m not trying, which is maybe offensive but probably true, and I feel like she’d be a very fun person to study in real time.

The other thing on my mind this week was family. But not in the way you think. In the last few days, three separate creator business launches and I noticed the same thing in all three of them. I’m breaking it all down in this week’s case study below!

Why is Hailey Bieber turning Rhode into a $1B empire while so many celebrity brands flop?

Last week on Hot Smart Rich, Shopify President Harley Finkelstein unpacked what actually separates iconic brands like Rhode, Skims, Kylie Cosmetics, Gymshark, and Chamberlain Coffee from the rest, and it’s not fame, it’s execution, discipline, and a deep understanding of the customer. From mindset shifts that help you finally start, to why most people stay stuck in self-doubt, to smart strategies for getting attention and building something meaningful, this episode dives into how top founders really think and win. It also explores the future of AI, creators, and commerce, plus real talk on money, life, and career decisions. If you haven’t watched it yet, this is your sign to do it.

all the brands, people, places, things we’re gossiping about this week

Women’s Health & Beauty

Media, Entertainment & Creator

Consumer, E-Commerce & Retail

Tech, Business & Investing

Why more founder-led and creator brands are keeping it in the family

This past week I found myself watching three separate creator business launches and noticing the same thing in all three of them.

Alix Earle's highly anticipated skincare brand, Reale Actives. Maureen Kelly of Tarte's second act, Finnsul. Nabela Noor's new Tubi lifestyle series. Three completely different categories, three completely different formats, and one undeniable commonality running through all of them.

Family is at the center.

Alix's manager is her father. Maureen's two co-founders are her Gen-Z sons. Nabela's director on her Tubi series is her sister. I noticed it and could not stop thinking about it, because not long ago, this would have been considered a liability.

I remember when I started investing, even five or six years ago, the prevailing wisdom was essentially: do not co-found with family. It was treated as an immediate credibility problem. A signal that you had not built the network, the discipline, or the professional boundaries to run a real company. VCs would quietly set it aside.

Something has shifted. And I do not think it is accidental.