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 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
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
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
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/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.
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