There is a version of every life that almost happened. The path we were on before we turned, suddenly, toward something we couldn't yet see. Most of us never talk about that fork in the road, or what it cost to walk away from the safe thing. This conversation is about exactly that moment, and what unfolds when you trust it completely.

Mike Erlin is the co-founder and CEO of AbilityMap, a company built to answer a question that followed him across three countries and twenty years: why do organisations keep getting it wrong on people, and why does nobody seem able to fix it? Before any of that, he was a footballer at the University of Oregon, a stranger on a yacht club dock in San Francisco, and a young man standing at a literal crossroads in Salt Lake City.

Highlights

The paper route that funded a household. When Mike's parents divorced in 1975, his mother was left with two boys and no income. At nine years old, Mike was lending her money from his paper route savings — the first lesson in a belief that would define his life: there is no option but to move forward.

Two worlds in one childhood. After the divorce, Mike's mother packed her sons into a Datsun station wagon and drove them to Guanajuato, Mexico, for eighteen months. He lived in a wealthy compound but crossed daily into a poorer part of town to play with friends who had dirt floors — an early, formative lesson in seeing people for who they are, not what they have.

The decision at the crossroads. Mid-route delivering a boat part to Salt Lake City, Mike faced a literal fork: turn one way back to his football team at Oregon, or the other way toward an America's Cup campaign in Australia. He turned toward the unknown — and has carried the guilt of leaving his team behind for years since, even knowing it changed the entire direction of his life.

The full circle nobody could have planned. Mike's America's Cup campaign brought him to Australia, where he met his wife. Decades later, he discovered that the same psychometric science used to help Australia win the Cup in 1983 had been pioneered by the man who would become his AbilityMap co-founder — a connection neither of them saw coming until it was already true.

Building lean, on purpose. AbilityMap ran for four years without sending a single invoice while Mike and his co-founder tested the science. They've taken minimal outside funding, survived a fifty percent revenue drop during COVID, and twenty-one months without income — choosing to do the job right over doing it fast.

Anchor Quotes

"There wasn't some huge spreadsheet that I used to weigh everything. I think I just looked at it and I felt what was going to be — I tend to do this, and it's definitely not always right."

"AI amplifies that which we have. If we have people who are misaligned from a capability standpoint, it's going to amplify that misalignment."

What stays with me from this conversation is how rarely the biggest decisions in our lives come with certainty attached. Mike didn't have a spreadsheet at that crossroads, he had a feeling, and the willingness to live with what it cost. If you're sitting at your own fork in the road right now, I hope this conversation reminds you that clarity often comes after the turn, not before it.

Connect with Mike Erlin: LinkedIn

Connect with Ability Map: LinkedIn | Website

Connect with Kirsty Ghahramani (Gee): LinkedIn | Instagram | Website

Most of us think reinvention happens in a single, dramatic moment. Jacqui Bloom's story proves otherwise. Hers happened in the kitchen, in hospital corridors, in a car stuck in traffic when she finally admitted she couldn't keep doing what she was doing. Across thirty years and multiple businesses, one question kept finding her: how can I help? This conversation is about what happens when you stop waiting to be ready and start answering it.

Jacqui Bloom started selling shoes at a Melbourne market at eight years old and was running her family's multi-million dollar fabric business by twenty-four. She has since built and lost businesses, walked through profound personal loss, and rebuilt herself into one of the most connected investors in the Australian startup ecosystem. Today she is Head of Investment at Backable and a Non-Executive Director at NASDAQ-listed Mobilicom.

Key Highlights

From the market stall to the boardroom. Jacqui's entrepreneurial instincts started at eight years old, selling shoes at her local market with her cousin. By twenty, she'd turned down a graduate role at a major bank to join her parents' fabric business instead. By twenty-four, she was running it.

The cost of carrying it all. At twenty-four, Bloom Fabrics went into administration. Jacqui talks candidly about what that meant for her father, the responsibility she carried as a young leader, and the perfectionism it left behind, the belief that there was no room to get things wrong.

When grief became the turning point. In the space of a few years, Jacqui lost her brother-in-law to cancer and watched her mother go through the same illness while she was having her own children. She talks openly about what it cost her to keep showing up, and how that experience became the seed of The Helping Hub.

Rebuilding an identity from scratch. Jacqui speaks with rare honesty about her divorce, what it meant to lose a twenty-year relationship and the version of family life she'd planned for her children, and the piece of advice from a school psychologist that changed how she carried herself through it.

Backing the next generation. From founding Shepreneur to building a fund inside Startupbootcamp to her current role at Backable, Jacqui has spent the back half of her career helping founders, particularly women, get access to capital. She shares an unflinching, sometimes provocative view on what is actually holding female founders back.

Two Anchor Quotes

"They decided that showing up was the credential."

"I couldn't ask people, can you come and wash my underwear? And that's where the idea for The Helping Hub was born."

What stays with me from this conversation is how many times Jacqui's life asked her to start again, and how many times she did. Not because it was easy, but because, as she told her own son during her divorce, we always have a choice in how we meet what happens to us. That's the thread running through every chapter of her story. I hope it gives you permission to find yours.

Connect with Jacqui Bloom: LinkedIn

Connect with Backable: LinkedIn | Website

Connect with Kirsty Ghahramani (Gee): LinkedIn | Instagram | Website