How to Dad with Tyler Ross

Above: Podcast host, Tyler Ross, with the top two reasons he loves being a dad. Photo by Caitlin Scott.

Wouldn’t it be nice if, along with the delivery of your bundle of joy, you were handed a manual on how to own and operate it? Any parent knows that’s hardly the case. Don’t share this with the kids, but we parents are winging it, every single day. Just when we think we understand the stage or phase a child is in – BAM – they switch it up. And if you have more than one child, you might know to expect curveballs, but no two children, or people, are alike.

The phrase “it takes a village” refers to more than just helping hands. Parents need to lean on family members, friends or colleagues for mental and emotional support and advice. Moms tend to have a larger base of support when it comes to parenting; whether it be a playgroup, books geared towards moms, or just picking up the phone to kvetch with another mom, it’s well within the social norm for women to talk about child rearing. But what about dads? Not so much, right?

Enter local businessman, owner of Ross Real Estate, and podcast host, Tyler Ross.

Tyler is an avid student of life and one of those high achieving types that make the rest of us mere mortals feel like, well, mere mortals. He’s also the father of two young children. As someone who constantly pushes himself to grow, he began to explore his role as a father and thought it would be enlightening to talk with other dads, too. Tyler has no problem connecting with other people who, like himself, push themselves, and he clearly enjoys straight talk with the new and old acquaintances alike.

I’ll tell you what… Being a dad is the hardest thing I’ve ever done. Every day I leave the house thinking, “Did I do the right thing?” “Should I have said that?”
–Learning to Dad Guest Curtiss Weinstein, Orlando, FL

Lifestyle talked with Tyler recently about the kinds of people he likes to interview on his popular podcast, “Learning to Dad with Tyler Ross,” what he’s learned from those interviews, and what the future holds for…

Lifestyle: When you’re considering who to have on “Learning to Dad,” what are some of the criteria you use?
Tyler Ross: I look for people who are wildly successful. People who are hard on themselves as well as being highly analytical, realize that to fill in the gaps, you first have to know where your holes are.

L: Which of your guests have been the most interesting and thought-provoking?
TR: I really can’t narrow that down; each guest has offered such different perspectives. If I had
to give an answer, I’d say Jesse Straight, owner and operator of Whiffletree Farm in Warrenton. Jesse is the father of seven children who live and assist on their working farm and his perspective is so different from mine. He is with his children constantly and their dynamic is different. His perspective on how his family interacts has incredible depth. And it might sound strange, but in today’s technology age, it was refreshing to speak with a ‘man of the earth.’

By Kara Thorpe

L: Is there a piece of parenting advice you’ve received that has changed your way of parenting?
TR: Absolutely! When I spoke with Ike Broaddus (co-founder of Old Bust Head Brewery), he shared his philosophy of always being honest. Whether it’s about previous relationships before you met your
children’s mother, extracurricular activities in your younger days, or even seeing consequences for punishments through – actually taking away the phone, or grounding if you threatened to – if you are
honest with your children, they will always know that they can rely and depend on you.

L: Why do you think the show is so popular?
TR: I believe it’s because there’s a lack of open and thoughtful communication among men. And we’re changing that. In a world where we have input coming at us from every direction, and constant stimulation, I wanted to share and start thoughtful dialogue. I started it in an effort to be genuine. We all have insecurities; this podcast is an exercise for me to let go of mine and be more comfortable in my own skin.

L: What are your future plans for the podcast?
TR: I have grand fantasies, but for now my plan is to continue to expand the network of people I speak with, drawing in different perspectives and experiences and sharing them for the benefit of other parents, and myself. I get to talk to really cool people.

L: What advice would you give to other dads?
TR: We can play a better role; we can be more deliberate. It’s all work, it’s all an effort, but you get back what you put into it. Stop trying to be perfect but do be authentic. Being perfect is impossible, but when you are authentic, it exposes you to genuine love and friendship.

When Tyler talks about work, he doesn’t mean that parenting is a job, per se. He warmly shares stories about his wife and children and the many activities they do together. His children inspire him daily, and were the inspiration his first children’s book, “Donkey and the Farm Team.”

Tune in to the thought-provoking conversations Tyler gets into with his lineup of great guests on “Learning to Dad with Tyler Ross.” Visit

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