Few companies show up on "best place to work" lists as consistently as Canva despite running at a level of ambition that would flatten most teams. Jennie Rogerson is the person responsible for holding that combination together.

She's Canva's Chief People Officer but she didn't come up through HR. She started as an EA to founders Mel and Cliff, became their chief of staff, then was handed the job of making Canva the best place to work.

She's openly sceptical of the high-performance-culture language most of Canva's peers reach for. She's made caring an explicit, unembarrassed part of how the company operates. And despite around 300,000 job applications a year, Canva still won't anchor its hiring to credentials.

Kate sits down with Jennie to talk about the interview challenge that got her the job (it involved the founders' anxious dog), why she thinks culture is never a system, "cheese grating" her own ideas with the people most likely to shred them, and what it actually takes to scale a culture people want to stay in.

🎧 [Apple Podcasts] | [Spotify] 📸 [@wildheartspod]

Danielle Strachman has built her whole career around a hard question: how do you spot someone who's going to do something extraordinary before there's any proof they will? She started as a school principal, helped build the Thiel Fellowship, and now runs 1517 Fund, backing founders without degrees and scientists most institutions won't go near. What she looks for is almost embarrassingly simple. Can this person not stop talking about the thing they're obsessed with? If the answer's yes, she'll ask for a Venmo handle and send $1,000 before the call is over.

It's an instinct with a track record. Ethan Thornton was seventeen when 1517 handed him a small grant to tinker in his garage. A year later, that became a $100,000 grant to start his defence tech company, Mach Industries. A year after that, Sequoia was in.

Most of our Wild Hearts guests this season are founders and builders. This one sits on the other side of the table, with the person who decides who gets backed. There's another twist: it's Joel Connolly, Creative Director and Head of the Blackbird Foundation, behind the mic. Back in June 2025, 1517 flew him to San Francisco to open their Fellowship Summit. Earlier this year, Blackbird flew Danielle out to speak at their startup festival, Sunrise.

Joel and Danielle get into what actually makes a weirdo worth backing, why she won't measure the return on last month's grant, how 1517 makes a call when the whole team disagrees, and why she thinks of the job as "homeschooling CEOs".

🎧 [Apple Podcasts] | [Spotify] 📸 [@wildheartspod]

Before Phoebe Saintilan-Stocks had a website, a company name, or a single piece of content published, she cold-messaged the COO of the Gates Foundation on LinkedIn. And they funded her.

It’s a pattern that runs right through both this episode and everything Phoebe has built since. The media company reaching 3.5 million people a month, the women's sports show on TV, the podcasts in categories nobody expected young women to care about, and the book built on cold emails to the chiefs of staff of Nelson Mandela, Jacinda Ardern, Justin Trudeau, Tony Blair, and Kamala Harris.

Most of us have started something without knowing quite what we were doing - no map, no contacts, figuring it out as we went - that part is familiar. The difference with Phoebe is what she did next. Because when her finger was hovering over the send button, she pressed it. And that one habit repeated relentlessly is how Missing Perspectives got funded, how The Right Hand got written, and how a blog on Squarespace became one of ANZ's most interesting media companies.

In this conversation with Kate, Phoebe talks about what the beginner's mind actually unlocks, why data will force you to kill the things you love and why you should let it, and what the chiefs of staff to the world's most powerful leaders taught her about trust, loyalty, and the one quality that makes or breaks any working relationship.