How Kelsey Charles Used her Nurtured Resilience to Create Her Own Success in Real Estate

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Top-selling millennial Realtor and Founder of The Kelsey Charles Team, Kelsey Charles CRS, MRP, CLHMS, has gone from battling addiction and financial turmoil to selling millions in the Hawaiian real estate market.

When Charles was 18 years old she lost her family, friends, job, most of her money, and her home. Feeling hopeless and a bit reckless, she bought a one-way ticket to Hawaii, planning to go to a college there that she couldn’t afford.

Charles earned Rookie of the Year from her previous brokerage in her first – and generated $55 million in sales before her third year of real estate. How did she get from point ‘A’, a homeless opioid addict, to point ‘B’, the successful real estate business woman she is today? Read on to find out more about her story.

A Rocky Start

Charles was born in Janesville, Wis., and fell into opioid addiction, shockingly, at age 12. She fell in love and started a family later in life, but not before getting sober. Charles went through opioid replacement therapy and was able to heal. She has been clean for over 10 years.

A Studious Woman

She has never been lazy nor shy of strenuous work and managed to graduate high school with honors, even though she often skipped school to help her mother make money. Her mom needed help paying rent, and Charles was determined to be supportive.

At 18, Charles left the continental United States and traveled to Hawaii with a scholarship to Pacific University. That is where she met her soon-to-be husband, but after getting pregnant, would later have to drop out to take care of their first child.

A Loving Mother

A hard worker and a harder-working mother, Charles was no stranger to tough times.

“It was like Soviet-style poverty,” she said of her new family’s lifestyle during her second pregnancy. “We made bread out of flour and water – couldn’t afford yeast – for a few nights.”

She started work as an Uber driver to try and make a few dollars a day, just so her family could afford to eat. Her second pregnancy also caused hyperemesis gravidarum (severe nausea and vomiting) during this time. But she pushed through because she is made of that kind of never-give-up drive that only living through a childhood like hers can teach.

A Stellar Realtor

Her decision to go into real estate in 2019, after the birth of her second child, was out of necessity, and she wasn’t going to fail at this new venture.

“The vast majority of people leave the real estate profession in their first few years and never really make a sustainable income, but I knew that I was just going to find a way to do it,” she explained. “So, I enrolled in a pre-licensing course. I just gambled on myself, hoping that I could figure it out.”

She definitely figured it out, and then some. She needed to help her Navy Veteran husband make ends meet. Speaking of her husband, his status as a 10-year Navy Vet inspired her to get into the home sales profession.

“I basically helped people buy houses using their VA loan. It allows them to buy a million-dollar house zero down. Military families often do not know the advantage they have in this brutal market. Many local families unfortunately never save up enough to afford their needed down payment,” she explained. “And Hawaii has the lowest property taxes in the nation, which makes it a prime investment.”

Charles created a Facebook page called Buying Home, Hawaii, and used her own lead generation system under The Real Broker, LLC.

What Does Kelsey Charles Want Next?

Charles is one of the top realtors in her area and sold $12 million in her first year, $25 million the next, and has sold a total of $55 million since she got her license.

Her clientele target has switched its focus in recent months, and her ideal customers are entrepreneurs who own multiple properties, looking to invest in luxury vacation homes in Oahu.

Charles is in the Top 10 realtors in The Real Broker, LLC, and is their No. 1 agent in Hawaii. The company operates in 40 states, DC, and Canada. It is continuing its binational expansion and is now a publicly-traded company. Because of this multi-locale format, real estate agents under their umbrella with licenses in multiple states can, theoretically, not incur repeated fees.

The brokerage offers a $12,000 cap and an 85/15% split compensation package. They aim to produce agents with a competitive revenue share and equity program that exceeds competitors.

What Kelsey Charles Wants to Show the World

“There are so many transferable skills learned when you have to work hard and hustle. You learn to be resilient and put in the effort to be successful,” said Charles. “I want people to know there’s hope out there, especially if they were an addict … you can still have an amazing life. You do not need to be a statistic.”

About Kelsey Charles, CRS, MRP, CLHMS

Kelsey Charles works with veterans and second-home clients to buy and sell homes in Hawaii. Since becoming a real estate agent in 2019, she has sold over $55 million worth of lucrative real estate investments. For more please visit her website,

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