Three things you'll learn in this episode: Why Matt says the biggest mistake he made wasn't working too much — it was not taking enough risks early when he still could bounce back How his wife's unconditional support became the silent foundation of everything he built — and what happens to founders whose partners don't have that belief What it actually feels like when your kids leave the house and go build their own lives — and why they never really leave your mind, they just occupy it differently What we cover: 00:00 — Introduction Matt, CEO of Hunter, husband, stepfather turned biological father, and the guy who went from bachelor to dad of a four-year-old in a very short window of time 00:00 — From San Francisco to Kansas Why two young people in one of the most expensive cities in the world packed up and moved back to a small town — and what that culture shock actually felt like 00:00 — The dot com bubble with a toddler at home Navigating a bursting industry, a career change, a new baby, a house purchase, and a relocation — all inside a two-year window 00:00 — What he gave up Sleep. Friendships. Art. Photography. The personal stuff that quietly disappears when you're building a career and raising kids at the same time 00:00 — The night shift strategy How Matt structured his days — work hard all day, come home for dinner and the kids, then grind again from nine until whenever — and whether he'd do it the same way now 00:00 — The risk he wishes he took Why he played it safe early in his career and why he'd go back and bet bigger if he could — even with kids at home 00:00 — His wife's role in all of it What unconditional support actually looks like. Why he says the partner question is binary — either they support it or the relationship breaks 00:00 — Building Hunter Ten years bootstrapped. Profitable. Built to fight for small businesses that everyone else ignores. Where the idea came from and what keeps him going 00:00 — When the kids leave How fatherhood changes when your kids stop being physically present and start building their own lives — and why they somehow take up just as much space in your head 00:00 — What success looks like for his kids Not what Matt built. Not what he earned. Just that they're living life entirely on their own terms. 00:00 — The risk envelope Why the best thing an entrepreneurial parent can give their kids isn't money or connections — it's a healthy relationship with risk About Matt Matt is the CEO of Hunter, a bootstrapped and profitable software company helping small businesses with lead generation and outreach. He has spent over two decades building companies and leading teams, starting with Bold Chat — which was acquired by LogMeIn — before founding Hunter. He is a husband and father of two grown sons, one of whom followed him into tech and one of whom became a tattoo artist in New York. He lives in Massachusetts. Website: hunter.io LinkedIn: https://www.linkedin.com/in/matttharp/ About Working Dads Working Dads is the podcast for fathers figuring out work, family, and everything in between. Every week host Johnathan Grzybowski sits down with working dads — founders, executives, investors, and everyday fathers — for honest conversations about the guilt, the grind, the marriage, the money, and what it actually takes to build a career and a family without dropping the ball on either. No gurus. No highlight reels. Just real talk. 🎙 New episode every week 📩 Subscribe to Built During Bedtime — our weekly newsletter for working dads 💬 Join the community — Slack and Facebook group For dads figuring out work, family, and everything in between. Nobody prepares you for this. Not the guilt of leaving for work when your kid is still asleep. Not the pressure of providing for a family while trying to build something that actually matters. Not the identity crisis that hits when you realize you're not just the guy who grinds anymore — you're somebody's dad. And that changes everything. I started Working Dads because I lived that. I'm co-founder of Penji, husband to Emily, and dad to a two-year-old who already has more energy than I do. I've been bootstrapping a company for over a decade and I still don't have it all figured out. But I've learned that the most dangerous thing a working dad can do is try to figure it out alone. So every week I sit down with founders, executives, investors, and everyday dads who are in the thick of it. We talk about the real stuff. The marriage conversations you keep avoiding. The financial pressure nobody admits to. The moment your kid looks up at you and you realize you've been somewhere else even though you've been standing right there. We've also got Built During Bedtime — my weekly newsletter for working dads. The one thing I write after my daughter goes to sleep. 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