Matt Tharp built Hunter into a 10-year-old bootstrapped, profitable company that helps small businesses grow through lead generation and outreach. He has worked alongside some of the sharpest operators in the SaaS space. He sold his first startup, Bold Chat, to LogMeIn after building it from three people.
But ask him what he would do differently?
It is not a business decision. It is not a missed market opportunity. It is not a hire he should have made sooner.
It is the communication he did not have with his wife during the hardest stretch of building.
On the Working Dads Podcast with host Johnathan Grzybowski, Matt opens up about going from bachelor to stepfather of a four-year-old practically overnight, what he gave up to build his career, why he would take more risks if he could go back, and why the partner question is binary: they support the vision or the relationship breaks.
He Gave Up the Right Things — And One He Didn’t Mean To
When Johnathan asked Matt what he sacrificed during the early years of building his career alongside a young family, the answer was honest.
“I gave up personal things. Sleep. Friendships. Things like: I grew up as an artist. I painted. Took photography seriously. A lot of that went by the wayside for many, many years.”
Sleep, he could spare in his twenties. Friendships, he chose consciously. The art — the creative identity that predated his business identity — he suspended, not permanently, but for long enough that it became one of the things he noticed was missing.
For working dads who are in the building phase: the things you suspend are not always the things you intend to suspend. Know the difference between a deliberate tradeoff and a slow drift. The former you can reverse. The latter builds distance that is harder to close.
The Communication He Wishes He Had Managed Better
Matt did not manage the communication with his wife well during the hardest stretch of building. He said this plainly and without qualification.
“I didn’t manage that part well.”
He was working constantly — going from a two-thirds work, one-third family balance to something closer to three-quarters or seven-eighths during the most intense seasons. His wife was supportive. She never pushed back on the career endeavors. She saw the opportunity and believed in the mission.
But the communication — the honest ongoing conversation about what the sacrifice was costing both of them, what the plan was, what the endpoint looked like — fell short.
“If you’re gonna start a business and you really want it to be successful, and the bigger the idea the bigger the commitment, your family unit has to support that endeavor or it will tear you all apart.”
For working dads who are building something significant: the support of your partner is not a given — it is earned through communication. Not just the big strategy conversations. The daily ones. The honest check-ins. The acknowledgment of what your partner is carrying while you build.
He Would Have Taken More Risks — Even With Kids at Home
This is the counterintuitive insight that defines Matt’s perspective on the early years.
Most working dads who look back say they wish they had been more present. Matt says that too. But he also says something fewer dads admit: he wishes he had taken more professional risks earlier in his career, even with young children at home.
“In hindsight, that’s what I would have changed. I would have taken way more risks, even with kids, because it’s so much easier to bounce back from those things in your twenties.”
He played it relatively safe during those early family years — building steadily, not overextending, protecting the household. He does not regret the outcome. But he recognizes that the reasoning was partially fear-based, and that the resilience available to a young entrepreneur with low overhead and high energy is a resource that does not get easier to access as you get older.
For working dads who are delaying the big move because the timing doesn’t feel right: the timing never feels right. And the version of you with a 2-year-old and a mortgage may actually be more resilient than you think.
What Working Dads Can Take From Matt Tharp
Matt went from bachelor to stepfather of a four-year-old in a very short window of time. He built two companies, sold one, and is now leading a bootstrapped SaaS business that has been profitable for a decade. He managed a lot of it well. The communication piece — the honest, ongoing conversation with his wife during the hardest stretch — he admits he got wrong.
That honesty is the most valuable thing he offers on the Working Dads Podcast.
His advice: if your partner isn’t willing to support what you’re building, either you’re going to quit or the relationship will break. It’s binary. Which means choosing the right person — and then communicating with them honestly throughout the build — is the most important business decision you will ever make.
Working Dads is the podcast for fathers figuring out work, family, and everything in between. Hosted by Johnathan Grzybowski, co-founder of Penji. New episodes every week.
