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Jessica Starr, a Keller Williams Agent, shares how she went from 2 transactions per year to a #1 agent amid trauma and turbulence. Jessica shares her story authentically with Caryn Prall on The Messy Empire Podcast.

Hi! I’m Lori Ballen, a Keller Williams real estate agent in Las Vegas, NV specializing in Summerlin.

I’ve taken the time to create an article about Jessica Starr and how she took her 2 transactions first-year real estate business to a top agent during turbulent times – including a PANDEMIC!

Listen To The Podcast

Caryn Prall hosts a fabulous real estate podcast called The Messy Empire, where she, AJ Guzman, and her guests prove that success is all about embracing the chaos and charging into the Unknown.

Caryn Prall hosts a fabulous real estate podcast called The Messy Empire, where she, AJ Guzman, and her guests prove that success is all about embracing the chaos and charging into the Unknown.

Jessica Starr was a guest and talked about her journey from selling two units in her first year of real estate to selling upwards of $45 billion a year in real estate currently. 

“She’s so fascinating because she’s super authentic. She is all about an abundance mindset. She is committed to her family and creating a legacy and memories. And I just think she just has overall her priorities in line.” – Caryn Prall

Jessica Starr is a Keller Williams real estate agent in Connecticut. 

Becoming a Real Estate Agent

She’s a 40-year old mother of 4. Her kids range from ages 6 to 14. She married her high school sweetheart, and they still live in the town where they grew up.

She's a 40-year old mother of 4. Her kids range from ages 6 to 14. She married her high school sweetheart, and they still live in the town where they grew up.

Jessica began her real estate career when she was 23 years old. Right before her wedding, she and her husband to be were both laid off. 

She decided then that nobody was ever going to control her opportunity to earn an income again. She wanted to control how she made money and how much income she received.

Her first year, she sold two condos for $140,000.  

“Everyone has to start somewhere,” Jessica says. 

She kept building her real estate business year over year, having four children along the way.

Jessica had closed 50 transactions before she hired an assistant. This assistant was transaction-based for $200 per real estate transaction.

After leaving Berkshire Hathaway in 2010 as a top-performing agent, she joined Keller Williams. At that time, she was closing about 5 or 6 Million in real estate sales volume.

Learning to Pivot

Jessica Starr, a Keller Williams Agent, shares how she went from 2 transactions per year to a #1 agent amid trauma and turbulence. Jessica shares her story authentically with Caryn Prall on The Messy Empire Podcast.

6-months after joining Keller Williams, Jessica discovered that she was pregnant with her second child. The next day, her husband suffered a traumatic accident at work, falling 16-feet out of a firehouse ceiling. 

Unfortunately, the fall broke his back.

Despite the obstacles, Jessica went to work, building her real estate team. She grew that year by 114%.

By September of that same year, she hired her first buyer’s agent. She was also still working with the part-time transaction coordinator. 

Jessica had learned how to Pivot.  

There’s not always a reason for everything. But here’s always a lesson or a blessing and everything that you go through,”

Jessica Starr

Jessica struggled with the massive growth and still having time for family, 

baseball games, special events. She was overscheduled and found herself on phone calls with clients even when she was physically present.

Time Blocking 

She got her time back, her friendships back, and experiences back, fully. She is grateful to have had a coach to help her learn time management and leverage.

She credits Keller Williams for teaching her time blocking. 

She got her time back, her friendships back, and experiences back, fully. She is grateful to have had a coach to help her learn time management and leverage.

Jessica says that she became learning-based after joining Keller Williams. Someone had given her a “Golden Ticket” while she was at her previous company to attend a Mega camp convention.

She was so excited about what she was learning that she wanted to run to her hotel room and start implementing ideas. She was so inspired. 

“Someone was FINALLY showing me the path,” Jessica exclaimed.

After Mega camp, she still went back to work at her brokerage. But after attending Keller Williams event called BOLD, she knew she had to move to KW, and she did.

That year, Jessica’s Dad suffered side effects from a botched surgery. After a year of travel and treatments, he, unfortunately, passed away. 

Due to Jessica’s inability to truly function at a high level during this time, her real estate team essentially “fired” her. They told her to take care of her family while they worked in real estate as a team. 

Jessica says that was one of the best production years without her physically present much of the year.

Prospecting for Listings

She was a prospector of leads. While her father was in the hospital, she would take her computer with her and prospect while he was sleeping.

As the rainmaker of the team, Jessica was the primary lead generator.

She was a prospector of expired listing leads. While her father was in the hospital, she would take her computer with her and prospect while he was sleeping.

She called expired listings.

She didn’t want to call her sphere of influence, or “book of business because they knew what was happening with her Dad. Most of them were friends on Facebook.

She knew that she couldn’t handle those conversations, so she stuck to calling expired listings.


Big Why

A 'Big Why' is a motivation that keeps you going if everything goes wrong. It's the inspiration that wakes you up in the morning.

Jessica had a “BIG WHY.” 

A ‘Big Why’ is a motivation that keeps you going if everything goes wrong. It’s the inspiration that wakes you up in the morning. 

It’s the one thing you think about again and again that keeps you breaking through ceilings of achievement because it matters.

Her ‘Big Why’ was supporting her Mom and Dad that year. Thanks to Profit Share, which is a benefit Keller Williams Realty Agents earn from bringing other agents into the company, Jessica was able to help them. 

And this was all while her husband was home caring for their four children. 

Something to Prove

That next year, Jessica decided it was time to focus on herself. She realized that she was saying YES to everyone else and NO to herself.

That next year, Jessica decided it was time to focus on herself. She realized that she was saying YES to everyone else and NO to herself. 

Looking back at a picture that should have made her happy, but didn’t, where her team, an all-female group had achieved the first millionaire real estate agent status, she saw sadness.

She saw a tired and unhealthy looking woman. She never wanted to make eye contact with someone. 

“When is it enough?” Jessica asks. “What is it going to take, and what are you trying to prove, and to whom? 

Who do you feel that you failed? 

You have to let go. Freedom comes from within, and then weight does come off. First, you have to become aware and accepting.”, she says.

Jessica realized that it was no longer about “winning.” As soon as she released the need to “prove” something, her business naturally grew, and she broke through the 100 transaction ceiling.

Word of the Year

An easy read, Jessica says the book is about finding a word for the year that symbolizes you and the change you want to see.

A friend gifted Jessica a book that she loves: One Word That Will Change Your Life by Jon Gordon and Jimmy Page.

An easy read, Jessica says the book is about finding a word for the year that symbolizes you and the change you want to see.

A powerful exercise, Jessica and her friends began texting each other: “What’s your word?”

The word that came to her heart was forgiveness. She wore a bracelet with the word: forgiveness. 

She began to forgive people that hurt her, intentionally or unintentionally, and herself. 

Jessica also says that having multiple coaches and a therapist help her on the journey. 

Gaining clarity around relationships helped her realize that she had been attracting the wrong people into her life. She was drawing in victim personalities so she could play the “Hero” that saved them. 

Her need to take care of others meant attracting people that needed nurturing.

A familiar theme for many. 

In a real estate business, attracting people who weren’t self-sufficient and needing constant care wasn’t going to work either.

The change has been remarkable. 

Even during the 2020 Pandemic, Jessica Starr’s team has grown. The blessings have come one after the next.

Family Wealth Building

"Teach your kids about the value of hard work and the value of money," Jessica advises.

Jessica’s Dad was always amazing at teaching her how to think bigger.

Her Dad was from immigrant parents that were from Poland and Russia.

They came over after the concentration camps. They worked tobacco, and they lived in a three-bedroom house with seven people. 

And that kid who lived on a dirt road, worked tobacco, and became a janitor, went on to become the head of the union for the hospital janitorial staff. 

He moved up from there, taking a top position at IBM.

Jessica’s Dad taught them to save. And when Jessica’s kids were barely in 1st grade, she had them open bank accounts. 

They walked in with change and whatever dollars they had and opened their accounts. 

Jessica believes in teaching children about the value of money.

She learned more about how to save and invest over the years through books, podcasts, and mentors. 

Some of the advice she followed, for example:

  • Put $19,500 per year in your retirement plan
  • Open an LLC, Add your husband’s name. 
  • Now put $19,500 per year in his retirement plan. 

Recently, Jessica’s 12-year-old son announced his idea for starting a new lawn mowing business. Jessica encouraged him to save $5,000 and open a retirement fund t 15. 

By 18, she explained, he could buy a house and rent it to his buddies. 

Jessica says that her credit history is 40 years old because she started early, thanks to her Dad.

“Teach your kids about the value of hard work and the value of money,” Jessica advises.

Jessica also invests smart. 

  • Every property purchased was made with at least a 20% downpayment
  • She lives below her means
  • Her rental properties earn enough to cover the mortgage plus her house that she owns and lives in

Jessica suggests that anyone wanting to learn about wealth and investing listens to Ben Kinney’s Win Make Give Podcast. 

She also recommends the book What Would the Rockefellers Do?: How the Wealthy Get and Stay That Way, and How You Can Too

Contact Jessica Starr

Jessica’s team, Starr Realty Group provides real estate services with Keller Williams in Connecticut. She says to reach out to her first for anywhere in Connecticut.

If they don’t cover the area, they will tell you who will. 

Jessica’s team provides Disney level service. You can find her on Facebook and the profit share mastermind. 

The Messy Empire

Caryn Prall is a owner and OP of Keller Williiams Realty Offices in the Chicago Area.
Caryn Prall is a owner and OP of Keller Williiams Realty Offices in the Chicago Area.

Caryn Prall lifts the curtains and gives you a true-view of an empire in the making. 

Caryn and her business partner Pete Economos have been diligently building one of the fastest-growing Real Estate companies in America for years now. 

Caryn shares it all with an astonishing amount of honesty and vulnerability. It’s gritty, hectic, and the most honest case study you’ll ever find on getting massive results out of your business and life.

Listen in

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