I arrive at the Heskett household on a gorgeous Saturday afternoon, greeted with a text message from Jennie reading: “I’m feeding my baby, just come on in!”  Opening the back gate, I enter a courtyard with a lovely pool and trappings of family life that warm my heart.  Dave Heskett, whom I’ve never met, is in the side yard and gives me a friendly wave.   He’s standing with a group of people, including neighbor Dr. Steve Kucera, and a crew of tree trimmers, looking up with furrowed brows at a damaged oak.  Dave tells me to let myself in the house, saying, “Jennie’s just inside!”

I used to walk by this stately 100-year-old house every day when taking my son to Southside Elementary, and I always loved the look of it.   Inside the gates, Jennie and David Heskett are carving out an extraordinary life together, and it was a happy accident I got to meet them both.

Earlier that day, I had inadvertently forgotten my interview with Jennie because I mis-calendared our meeting for Sunday.   She had arranged for childcare and had been waiting for me alone at the Morton’s bakery by the time I realized my error. Filled with chagrin at my mistake, she was gracious to offer that I stop by her house later that day, and I’m very glad I did.  I loved every second of meeting this family and seeing their sweet and happy home.

FYI, she was really cool about being stood up, texting me, “It’s okay! I haven’t had a cup of coffee by myself in months lol.”

So that’s how I find myself chatting with Jennie as she feeds baby Robby.   Jennie has an affable, breezy way about her, a warmth that radiates.  I’ve interviewed a lot of folks over the years, and I find Jennie remarkably easy to talk to, like we are old friends.

Robby cooing contentedly in her lap, she tells me how the Hesketts came to be.  

“I first moved here in 2004, during college,” she begins, “My summer jobs were scooping ice cream at the Kilwin’s on St. Armands and also coaching gymnastics.”  Jennie’s older sister lived in Sarasota, and, that summer, she “occasionally” mowed the grass in exchange for room and board before heading back to Arkansas Tech in the fall.

When she was 16, Jennie’s family relocated to Arkansas from her native state of South Dakota, which drove her choice of college and graduate school: she earned her Doctor of Physical Therapy  degree from University of Central Arkansas before heading off to New York.  In the city, she shared a cramped apartment with a handful of other people, musing, “My closet now is bigger than my room was in New York.”

Looking for somewhere to spread her wings, both literally and figuratively, she came back to Sarasota, where, by then her mom and her brother also lived.

Jennie and Dave met when a yoga buddy of Dave’s introduced them.  “He didn’t expect to meet the woman of his dreams in Sarasota,” she says, with palpable mirth.

A Chicago native, Dave was then serving as the interim CEO of a company in Lakewood Ranch at the behest of his employer, a Midwest private equity firm.  When the temporary assignment ended, he had a big reason to remain in Sarasota.

Jennie and Dave moved into a condo at 1350 Main before buying in our neighborhood in 2016 and then getting married.  “He proposed right in front of that fireplace,” Jennie says, gesturing to the mantle across the room, “on Christmas.”  

By this time, Dave and Dr. Kucera, who is introduced to me as “Chef Steve” have come in from the activity outside, and now chainsaws are buzzing from the yard.  Jennie lowers her eyes, saying, “The tree is too damaged to be saved.  We’ll really miss it.”  

The couple got married in a small ceremony in Jackson Hole, Wyoming, where Dave’s parents now reside.  Jennie says, “We love trees and nature, so it was just the perfect place for us.”  After getting married, Jennie transitioned from physical therapy to a remote sales position so she and Dave could adventure together, as Dave’s job (still with the same private equity firm that brought him to Sarasota) now entailed being away from home almost every week.   

Eventually, now two-and-a-half-year-old Olive joined the family, followed by baby Robby.  The entire time I’m with Jennie, Robby is on her lap, grinning, gurgling at her or me. “He’s an easy baby during the day,” she says, then laughs, “but I wish he slept better at night.”   These days, Dave still travels during the week, and Jennie juggles weekday family life and her current career in real estate.

Dave comes over and offers us wine.  Over the glasses, Jennie tells me about her latest career turn and her business partner, lawyer and fellow realtor Nick Gard, who hang their realty hats with Coldwell Banker.  

Of the new venture, she offers, “I love change and trying new things!  I thought I might be good at real estate given my sales and marketing experience, combined with the listening skills I was fortunate enough to inherit from my parents.   Plus, I love homes!”   

She tells me how she and Nick bring out the best and complement each other as a team, and it’s obvious she means it.  She talks happily about a showing she’s hosting later in the afternoon around the corner from the Heskett house.  

Jennie and Nick specialize in West-of-Trail residential sales. “I feel so at home here,” she adds, “We love going to dinner at someone’s house, or hosting in our home, or having wine with neighbors.”  Looking over at Chef Steve, who is still chatting with Dave in the kitchen, she says, “This guy and his wife —Dr. Jennifer Kucera— have been working on the perfect dough recipe for five years, and pizza nights at their house are amazing.”  

Later, Dave and Jennie give me a tour of the thoughtful renovations of the house they did in 2019 and talk about the travels they’ve loved most (the Duro Valley, Portofino) and what new places they’re looking forward to visiting when the kids get just a bit older (Bordeaux).

I’ve never been happier leaving an interview.  We trade hugs, and the baby smiles at me for the millionth time.  The Hesketts are so warm, and so real and welcoming.  We’re truly blessed to have them in the neighborhood.