Mar 11, 2022 · 59m · news
Shopify President, Harley Finkelstein on What is Being a Good Husband | Full Interview · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this 20VC interview, Shopify President Harley Finkelstein discusses his career journey, the evolution of his empathetic leadership style, his advocacy for vulnerability, and the intentional strategies he uses to maintain successful professional partnerships and family relationships.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 12.7% of the talking time here. How this is scored →
Harry as informed peer 2.0 Guest teaching 2.8 Guest disagreement 0.7 Harry pushing back 0.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 26:47 Harley reframes Harry's premise on storytelling
Harley politely rejects Harry's assertion that founders lack storytelling skills, clarifying that the true core required is mission articulation rather than narrative craft alone.
Hardest push from Harry ▶ 26:14 Harry challenges modern founder narrative capabilitiesHarry takes a firm stance against prevailing founder communication habits, declaring that 99 percent of founders today can no longer build enticing narratives.
Biggest teaching moment ▶ 39:40 Harley teaches a operational framework for relationship listeningHarley educates Harry on how to suppress reflexive problem-solving by explicitly asking a partner whether they need solution mode or simple listening.
Harry holds his own ▶ 10:05 Harry highlights shift in venture capital round namingHarry demonstrates keen venture capital market awareness by instantly interjecting that a historical $7 million Series A round would be considered a pre-seed today.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Harley's Entrepreneurial Roots and Shopify Journey | 1 | 1 | 0 | 0 | Harry opens with an admiring welcome and asks a broad origin question about how Harley and Tobi met. Harley responds with high praise for Harry's growth as a host before detailing his early entrepreneurial path. | |
| Overcoming Setbacks, Resilience, and Empathy in Leadership | 2 | 2 | 0 | 0 | Harry shares personal family background to connect with Harley's setbacks and later notes that Shopify's historical $7M Series A would be a pre-seed round today. Harley elaborates on evolving from a fast-paced bull in a china shop to an empathetic leader. | |
| The Power of Vulnerability and Managing Insecurity | 2 | 3 | 0 | 0 | Harry openly shares his own insecurities about managing a quarter-billion dollar fund and fearing irrelevance. Harley offers educational insights on distinguishing eustress from distress and managing anxiety openly. | |
| Storytelling, Mission, and Building Complementary Teams | 3 | 4 | 2 | 2 | Harry asserts a bold premise that 99 percent of modern founders have lost the art of storytelling. Harley gently counters by reframing storytelling as mission articulation and illustrating with examples like Gymshark. | |
| Partnerships, Marriage, and the Dynamics of a Successful Relationship | 2 | 4 | 1 | 0 | Harry asks for relationship advice to avoid mediocrity in his personal life. Harley educates Harry on actionable marital strategies, including trust batteries and asking whether a partner wants active listening or problem solving. | |
| Mindful Fatherhood, Quick-Fire Insights, and Future Outlook | 2 | 3 | 1 | 1 | Harley breaks down mindful fatherhood and his calendar discipline, sparking light banter when Harry calls calendar invites unromantic. The segment closes with a rapid-fire Q&A on leadership and book recommendations. |
Statements from this episode (16)
Tobi Lütke launched Shopify when his software outgrew his snowboard business
“By 2005, it became clear to him that the software behind the snowboard business was more valuable Than the snowboard business itself. And so he launched Shopify.”
Finkelstein was one of Shopify's earliest e-commerce merchants
“And so I became one of the first merchants to use Shopify.”
Law school serves as a finishing school for entrepreneurs
“So law school for me was really more like finishing school for entrepreneurship.”
Shopify raised its 2010 Series A at a $25M post-money valuation
“He was in our Series A, first market in our Series A back in, in 20, 20, 10. It was actually, it was a seven million Series A, I think on a twenty-five million dollar post valuation.”
Finkelstein: Communication clarity depends on the listener, not the speaker
“I think that that is all about empathy, which is like, okay, you think you're being clear. What does the other people person think? If they don't think you're clear, then it doesn't matter what you think.”
Harry Stebbings manages $250M five years after having £50 to his name
“Manage a quarter of a billion dollars, which is a joke, considering when we were five years ago, I had about 50 quid to my name.”
Shopify processes 10% of all e-commerce in the United States
“10% of all e-commerce in the United States is done via Shopify.”
A new entrepreneur makes their first Shopify sale every 28 seconds
“Every 28 seconds, a new entrepreneur gets there for sale on Shopify.”
Finkelstein: 4.6 million new US businesses registered in 2021
“I think the numbers were like 4.6 million new business registrations happened in 20, 21 alone in the United States, like this massive jump from a decade earlier.”
Finkelstein: Tobi Lütke is the greatest product mind on Earth
“I mean, Toby, I think is probably the greatest product mind on the planet.”
Finkelstein: Great founding teams have non-overlapping skill sets
“I think that a lot of people start businesses with people that are just like them. People that they would be friends in high school with. But if you look at some of the best teams out there that have built incredible companies they are really different. I mean…”
Shopify starts all new employees with a 50% trust battery rating
“Everyone that comes to Shopify starts at a 50% trust battery.”
Harley Finkelstein attends couples therapy with his wife every two weeks
“We've been seeing a couples counselor almost since like day one. We've been seeing, we've been going to couples therapy and we initially did it because on the advice of someone that one of these mentors that I think has a great relationship who only started se…”
Asking "listen or solve" improved Finkelstein's marriage tenfold
“That small, those two lines do you want me just to listen or do you want me to help you solve it? I think has increased our dynamic and our marriage and frankly, like the romance and love of our relationship probably tenfold.”
Shorts cut from this episode
▶ Do you know the concept of IKIGAI? · 20VC with Harry Stebbin (@51:32)
▶ Do you know the concept of Ikigai? 🇯🇵 #shorts · 20VC with (@51:32)
▶ The origin story of GymShark 🏋️🦈 #shorts · 20VC with Harry (@31:15)
▶ Operation HOPE: To creating a million more Black Entrepreneu (@53:54)
▶ The X-Factor to great partnerships! 🎉 #shorts · 20VC with H (@35:23)
▶ The KEY to being a Great Father · 20VC with Harry Stebbings (@45:22)