At 17 years old, when his father was arrested for white-collar crimes, Finkelstein experienced a foundational trauma that pulled the rug from under him and forced him to grow up overnight, profoundly shaping his drive for achievement and his relationship with security.

Shopify runs 12% of all US e-commerce, making it the second-largest checkout platform after Amazon, and AI will accelerate the trajectory of business growth because small entrepreneurs can make better decisions faster with less human capital.

Stress comes from misalignment between what you say you want and what your calendar shows you actually doing; the calendar never lies about priorities.

Finkelstein's family carries multigenerational trauma from his Holocaust survivor grandparents and his father's financial struggles, which manifests in his own scarcity mindset and belief that he never has enough, has done enough, or is enough—despite his professional success.

Being happy requires being excited by all the elements of your life, and Finkelstein is excited by all the elements of his life, which is why he has high energy and doesn't experience Sunday scaries.

Finkelstein created 'Firebelly Tea' with David Seagull (founder of David's Tea) because Seagull is the most passionate person about tea; once you identify someone deeply passionate about something, they should build a company in that domain.

Finkelstein believed his father took massive personal risks and risked 5–6 years of federal prison time to provide a better life for him and his siblings, which shifted his emotional relationship from anger and disappointment to deep admiration and empathy.

Finkelstein aspires to be world-class at storytelling—specifically at taking brilliant things Toby built and communicating their value to investors, media, merchants, and partners—which he believes is the greatest value-add he brings to Shopify.

Finkelstein also wants to be a world-class father and husband, which is more difficult to measure than storytelling because he can't get objective third-party feedback, but it's deeply important that his kids and wife believe he excels in these roles.

In Street Fighter, characters have trade-off attributes—some are great at defense but bad at offense, some great at jumping but bad at kicking—and life is similar: you cannot be good at jumping, defense, offense, and kicking simultaneously, so you must choose what you want to be good at.

Toby is the source of the re-qualification energy at Shopify—he relentlessly pushes himself to be the very best at product and technology, and this pushes everyone else to continuously ask 'is there another gear in me?' and improve.

Finkelstein wears James Perse t-shirts every day because James Perse himself is obsessed with Japanese cotton, American cotton, GSM counts—he made the products for himself first, so thousands of others now want them too.

Finkelstein recently started DJing again and developed mentorship with Alex at Moog Audio shop in Montreal, learning modern DJing techniques like stem isolation (separating drums, bass, vocals, and instrumentals) rather than the beat-counting approach he learned 20+ years ago.

Some people (like Finkelstein) find detailed, scheduled planning energizing; others find it anxiety-inducing; knowing yourself and structuring life accordingly matters more than any universal system.

Young brands (Viori, Alo Yoga, Figs) that didn't exist a decade ago are now billion-dollar public companies and category leaders, proving the acceleration of entrepreneurial success timelines.

Toby gives compliments sparingly and only when someone has clearly exceeded industry expectations and reset what's possible in their domain, treating baseline performance as non-complimentable and exceptional performance as the only worthy of recognition.

Finkelstein became visibly unhappy and 'non-exothermic' as COO—not energized as usual—and lost his signature high energy when meeting merchants, causing Toby to notice and suggest a transition to a role better suited to Finkelstein's strengths.

Finkelstein has coaches and mentors for specific skill areas, but at some point you stop learning new frameworks from any given coach—you've seen the entire 'toolbox'—and that's a good time to move on to the next coach, which is not a criticism but a natural lifecycle.

Finkelstein's father created business cards for every business idea he proposed as a child, embodying a message that he absolutely had the capacity, willpower, and permission to pursue any entrepreneurial venture, which became foundational to Finkelstein's confidence and willingness to take action.

Being a world-class husband requires overriding his natural tendency to go into problem-solving mode when his wife shares a problem; instead, she often just wants to be listened to, so he created a mnemonic device where he asks her 'Do you want me to solve this or do you want me to listen?' to interrupt his reflex.