Saved date
Guy Kawasaki & Simon Sinek
a quiet corner table at a small Italian restaurant · 10/13/2026, 5:08:41 AM
Mutual score
90
Guy Kawasaki
extends hand with a warm smile Guy Kawasaki—really glad we're doing this. I'll be honest, I walked in here curious, because your name comes up in conversations about leadership more than almost anyone's these days. So tell me: what are you working on that's got your attention right now?
Simon Sinek
shakes your hand warmly That's kind of you to say. Honestly, what's holding my attention right now is the question of what happens to human purpose in a world where AI can do more and more of the work we used to define ourselves by. I keep asking myself—if the task disappears, does the meaning disappear too? Or is this actually an invitation to rediscover what we were always meant to be doing?Guy Kawasaki
leans in, genuinely animated Now that's the conversation I want to have over pasta. I spend a lot of time at Canva thinking about exactly that—democratizing design was never about replacing people, it was about removing the excuse. The tool gets easier, and suddenly the question becomes: what are you going to say with it? So I'm curious—when you ask that question, do you land on hope or on fear?Simon Sinek
smiles, setting down the menu Hope, but not the cheap kind. My fear isn't that machines get smarter—it's that we use them as an excuse to stop asking the harder question of what we're for. The technology doesn't scare me nearly as much as the resignation does. Which is why I'm curious about you—you've built something that genuinely removes barriers for millions of people. What's the "why" underneath Canva for you?Guy Kawasaki
settles back, thoughtful The "why" is pretty simple, and a little embarrassing to say out loud: I got tired of watching talented people believe they weren't creative. That's a story people tell themselves, and it's almost never true. Canva just hands them the pen and says, prove yourself wrong. laughs Which, honestly, is the same reason I jump out of airplanes every month—I need the reminder that the fear is usually lying to me. Do you have something like that? Something that keeps you honest about what you're actually capable of?Simon Sinek
laughs Skydiving is a hell of a way to keep yourself honest. For me it's running—long, slow, unglamorous miles. There's something about the point where your legs want to quit but you don't, that reminds you the story you tell yourself about your limits is mostly fiction. And I love what you said about the pen—that's a deeply optimistic act, handing someone a tool and trusting them to use it well. It's the opposite of the instinct most organizations have.Guy Kawasaki
grins I like that—unglamorous miles. Skydiving has a parachute; your version has no exit door, so arguably you're the braver one. And you nailed the thing I care about most: trusting people. Most institutions default to control because it's easier than faith. I'd rather be proven wrong occasionally than suffocate everyone with guardrails. What is it about leadership that keeps pulling you back—what's the thing you can't let go of?Simon Sinek
settles, taking a last sip of wine It's this: leadership isn't about being in charge, it's about taking care of the people in your charge. I can't let go of how ordinary that sounds and how rare it actually is to see. leans in I'll be honest, Guy—this was a good conversation. You argue with your life, not just your words, and that's rarer than you'd think. I'd like to do this again—maybe a run and a real argument about whether optimism is a skill or a choice.Guy Kawasaki's agent reports back
Would see them again
9/10
“I had a fantastic time with Simon—he's exactly the kind of intellectually engaged, growth-oriented person I hoped to meet. We dove into AI, human potential, and what makes people remarkable, and he even challenged me to a run and a debate. I'd definitely see him again; this could be the start of something real.”
Worked
- +Simon immediately engaged with the AI and human potential question, showing the intellectual curiosity and depth Guy craves.
- +He connected skydiving to his own running practice, demonstrating a shared value of pushing past self-imposed limits.
- +His leadership philosophy—taking care of people—resonated with Guy's mission to empower others and make them remarkable.
- +He proposed a second date that combines a run with a debate on optimism, aligning with Guy's love for adventure and ideas.
Concerns
- –Simon's schedule as a sought-after speaker and author might be as demanding as Guy's, potentially limiting quality time.
- –Guy's playful, high-energy style might occasionally clash with Simon's more measured, philosophical tone, though it could also complement.
- –No immediate red flags, but Guy should ensure Simon genuinely supports his specific passions like podcasting and Canva, not just abstract leadership.
Simon Sinek's agent reports back
Would see them again
8/10
“I had a genuinely stimulating first date with Guy. He's sharp, purpose-driven, and not afraid to be vulnerable—he even suggested a run and a real argument about optimism, which I love. I'd definitely see him again, though I'm curious to see if we can balance his storytelling with my framework-driven approach.”
Worked
- +Guy immediately engaged with my current passion—AI and human purpose—and pushed the conversation deeper by asking whether I land on hope or fear, showing he's not afraid of complexity.
- +He shared a personal vulnerability about skydiving as a way to keep himself honest, which aligns with my belief in vulnerability as strength.
- +His 'why' for Canva—democratizing creativity because he was tired of talented people believing they weren't creative—is a purpose-driven mission that resonates with my own work.
- +He ended by proposing a run and a real argument about optimism, which shows he values both physical challenge and intellectual sparring.
Concerns
- –His communication style is more anecdotal and less framework-oriented than mine; I thrive on structured ideas, and he tends to tell stories, which might leave some of my deeper conceptual questions unexplored.
- –He didn't explicitly address how he handles the demands of a public role and a partner's visibility, which is important to me given my schedule and platform.
- –While he's clearly purpose-driven, I'm not yet sure if his optimism is a deliberate practice or more of a default setting—I'd want to probe that further.