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1:59 mins
I had a husband of a dermatologist reach out saying, “Hey, my wife never really comes home for family dinners. Can we please try this and see if it works?” So he set his wife up fully, and she went on. I called them three months later and he said, “Yeah, she’s coming home at 5:30 now.”
There’s a momentum you feel — like it hooks. It builds and builds. As I started working with students and seeing the outcomes, it really landed. Something like 97% of them got professional development they never received through traditional school. About 77% increased their financial output within six months of the program.
We were seeing economic growth. People were starting businesses, hiring others. And honestly, it’s who you become along the entrepreneurship journey — and the people you meet — that’s the golden stuff.
We talk about bringing your kid on stage, which is such a smart idea, but really, there’s emotion in startups and in entrepreneurship. You’re bringing something into the world that didn’t exist yesterday — and that feels frickin’ great.
It doesn’t necessarily have to be your life’s work, but you do have to like your customers. You’ll spend a lot of time with them.
If you’re building a product for people you don’t actually enjoy spending time with, don’t do it. For example, we don’t lend to startups; we lend to scale-ups. I enjoy spending time with founders, asking them hard questions about their businesses, probing their financials. But if that’s not your jam, then you definitely don’t want to run a business like mine.
The true payoff of entrepreneurship isn’t found in funding announcements or revenue milestones – it emerges in those quiet moments when you realize your product is genuinely changing lives. Kai’s story captures this perfectly: a dermatologist’s husband reached out because his wife “never really comes home for family dinners,” asking if their product could help. Three months after implementing Lyrebird, the husband reported that “she’s coming home like 5:30.” This transformation from a doctor working endless hours to someone who can prioritize family dinner represents the kind of impact that makes every sleepless night and failed pitch worthwhile.
Jeanette describes how momentum builds when you start seeing tangible outcomes: “97% of them get learning for their professional development that they don’t get through traditional school” and “77% increased their financial output within six months.” But the real magic happens when these individual successes compound into something larger – “we’re actually seeing economic growth, we’re seeing people start businesses, we’re seeing them hire other people.” The payoff isn’t just solving one problem; it’s creating ripple effects that transform entire communities and industries.
The personal transformation that occurs during the entrepreneurial journey often becomes as valuable as the business outcomes. “It’s the person that you become as you’re doing the entrepreneurship journey, it’s the people you meet during the entrepreneurship journey that’s the golden stuff,” Jeanette reflects. This evolution happens gradually – through countless difficult decisions, relationship-building, and problem-solving – until founders realize they’ve developed capabilities and perspectives they never knew they possessed.
There’s also a unique emotional reward that comes from creation itself. “There is this emotion to startups and an emotion to entrepreneurship where you’re bringing something into the world that didn’t exist yesterday and it feels frickin great,” Jeanette explains. This creative satisfaction goes beyond traditional career achievements because entrepreneurs aren’t just excelling within existing systems – they’re building entirely new solutions, markets, and possibilities.
Matt Allen adds a crucial insight about sustainable entrepreneurial happiness: you don’t necessarily have to be building your life’s work, “but what you do have to like is your customers because you’re gonna spend a lot of time with them.” This wisdom highlights that the real payoff comes from aligning your work with people and problems you genuinely care about. If you’re building something for people you don’t enjoy spending time with, even success can feel hollow. The ultimate reward is creating value for people you respect while becoming the person you were meant to be through the journey itself.
Jeanette Cheah – Co-founder & CEO of HEX. A leading alternative education company. Left corporate banking after 14 years to build something meaningful.
Matt Allen – Co-founder of Tractor Ventures. Built Australia’s leading scale-up lending platform from scratch, despite having “the least entrepreneurial family on earth.”
Bennett Merriman – Co-founder & CEO of Rosterfy. Scaled from university side-project to managing 120,000+ volunteers for global events including the Super Bowl.
Kai Van Lieshout – Co-founder & CEO of Lyrebird Health. Engineer-turned-founder solving healthcare’s biggest inefficiencies through technology.
Dr. Anushi Rajapaksa – Founder & CEO of Misti. MedTech innovator. From hospital corridors to building life-changing medical devices, including taking her daughter on stage at demo day.
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