"Just be yourself," she says. "I had imposter syndrome. I was faking it until I was making it. But they appreciated my candor. They appreciated my transparency."
When Alaska Kessel first pulled this family's contact information from the "shark tank" — the archive of old leads at her brokerage that newer Agents can fish through — she had no idea she was opening a chapter that would span years, multiple properties and one of the most meaningful professional relationships of her career.
"I dug them out of the archives," Alaska recalls. "They were leads that had been worked in the past but hadn't really gotten anywhere or maybe hadn't found the right fit with an Agent." The fit, it turned out, was Alaska.
A Big Ask for a Brand-New Agent
The family she connected with wasn't looking for just any home. Their current residence — a four-acre estate in Boca Raton designed as a replica of an English castle — set the bar for what "home" meant to them. They had raised their children there, watched cobwebs give way to character and poured decades of life into its walls. Now, with grown kids and a new chapter ahead, they were ready to explore what came next.
What came next, apparently, was $1.2 million showings on St. George Street and Palm Row in St. Augustine — the kind of historic, architect-designed properties that carry both a price tag and a legacy.
For a newer Agent, the pressure was real.
"It was a little outside of my comfort zone," Alaska says. "I was nervous. I was a newer Agent."
But she showed up anyway, leaning into something she'd have to learn to trust: herself.
The Right Fit at the Right Price
After touring the million-dollar listings, the family landed somewhere unexpected — a $300,000 beachfront condo that needed a little elbow grease but offered exactly what they actually needed: a foothold in St. Augustine without having to fully uproot from Boca. A place to dip their toes in before committing to the leap.
The unit had one quirky detail Alaska still remembers: carpet squares. Individual, replaceable squares of carpet, an old-school, practical touch that the family immediately recognized as genius for a rental or vacation property.
"If you spill something, you don't have to replace the whole floor," Alaska laughs, "just that one little square."
They negotiated, factoring in the work the property needed, and made the deal happen in 2021.
Three Transactions and Counting
That condo was just the beginning. The family came back to Alaska for a second property — something more in line with the vision they'd originally shared, a beachfront vacation spot where the whole family could gather in St. Augustine. And now, in their third transaction together, they're selling that original condo, the one that started it all.
The numbers tell a compelling part of the story: thanks to the 2021 market and Alaska's strategic pricing, the family stands to walk away with nearly $200,000 in net proceeds on that sale.
"I already ran the numbers with the title company," she says. "That's net. We priced it so that they could get that amount."
The Lesson She Carries Forward
When asked what she'd take from this relationship and apply elsewhere, Alaska doesn't hesitate.
"Just be yourself," she says. "I had imposter syndrome. I was faking it until I was making it. But they appreciated my candor. They appreciated my transparency."
She's seen what the alternative looks like, Agents who are "more in it for the sale," less forthcoming, a little too polished to be real. For clients with the means and the discernment this family has, that doesn't fly.
"With clients like these, they do not appreciate that," Alaska says. "They want someone who's going to be upfront with them, honest with them."
And perhaps more than any closing price or commission, that's what Alaska Kessel has built over these three transactions: a reputation as someone this family trusts with their most significant decisions, their portfolio and their next chapter wherever in Florida it leads.