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Dr. Kylea Woodley-Jones
She Joined TSP as a Full-Time Teacher. Four Years Later She Has a Team of 12.
She Joined TSP as aFull-Time Teacher. Four
Years Later She Has a
Team of 12.
Dr. Kylea Woodley-Jones was already posting six figure years when she found TSP. She was also drowning in them, with no systems, no team and a full-time teaching job. Here is what four years in the room changed.
Dr. Kylea Woodley-Jones was already posting six figure years when she found TSP. She was also drowning in them, with no systems, no team and a full-time teaching job. Here is what four years in the room changed.
At a glance
Founder
Business
From Craft to Cash: custom apparel and crafting, plus coaching and a design club
Before TSP
Full-time teacher with a doctorate in education, running the business nights and weekends
In TSP since
Team today
12. Two in the craft house, one on service and maintenance, the rest remote
Status
Full-time entrepreneur since leaving teaching earlier this year
Founder
Business
Before TSP
In TSP since
Team today
Status
Dr. Kylea Woodley-Jones
From Craft to Cash: custom apparel and crafting, plus coaching and a design club
Full-time teacher with a doctorate in education, running the business nights and weekends
June 2022. TSP Mastermind, moved up to the TSP Collaborative in January 2026
12. Two in the craft house, one on service and maintenance, the rest remote
Full-time entrepreneur since leaving teaching earlier this year
The numbers
Kylea is the first to admit she was not tracking closely: "I wasn't a number watcher. I just did what I was supposed to do." What she does remember:
Point in the journey
Before the TSP Mastermind
Where the business was
Six figure years, while teaching full-time
Point in the journey
Year two
Where the business was
A jump of roughly $200,000
Point in the journey
Year three
Where the business was
Over $500,000
Point in the journey
A breakout month
Where the business was
$84,000, a $30,000 jump she credits to people in the room pushing her
Point in the journey
The month that decided it
Where the business was
Her entire annual teacher salary, earned in one month
Point in the journey
Before the TSP Mastermind
Year two
Year three
A breakout month
The month that decided it
Where the business was
About $20,000, enough to clear all her credit card debt
$63,000
$1.08 million
$84,000, a $30,000 jump she credits to people in the room pushing her
$84,000, a $30,000 jump she credits to people in the room pushing her
More recently, in her own words: "You literally just made a month worth of your teacher salary times two, in 90 minutes."
Where she was when she walked in
Kylea taught entrepreneurship, and she taught it with an unusual rule for herself: every single year, she started a brand new business from scratch so her students could watch her do it.
"I didn't want the students to look at me and say, well, you're successful because you're already successful. So every year we pick a new topic, and every year I would turn that business into another six figure business."
One year the new thing was t-shirts. The orders poured in and did not stop. She was building the business at night while teaching full-time, working on her doctorate, pregnant, and planning a wedding.
"I was a psychopath. I definitely didn't have the systems. I didn't have the structure. It was bootstrap, just grinding all day."
This is the opposite of the usual case study setup. Kylea was not failing. She was posting six figure years as a full-time teacher, and she was drowning, because success at that volume with nothing underneath it is its own kind of trap.
How she decided
Kylea was not shopping for a mastermind. She was at a marketing conference, and she noticed something nobody around her seemed to be tracking.
"Every person that spoke on the stage at that conference, no one actually said where they were from. But they were like, 'my coach, my coach, my coach, my coach.' And I was like, well, I want to figure out who is coaching all of them."
Lamar was one of the speakers that day. She had never heard of him and thought nothing of it. Afterward she could not let it go, so she went through every speaker's social media until the same name kept surfacing, found the website, and found the TSP Mastermind.
"I don't know what this means, but I need it. My business needs it. I'm drowning. I don't care what it takes. I'm in."
Then she got on a call and heard the investment.
"I about passed out."
Her husband told her she had lost her mind. Her argument back was that you cannot take perfect credit with you when you die, and underneath the argument was a conclusion she had already reached:
"Either I give up my business, or I get help so that my business is sustainable."
She did not wait for the next intake. She joined mid-cycle and went straight into her first session.
What the four years did
Kylea describes her time in the TSP Mastermind the way you would describe college. The framing is hers.
"I made it through my freshman year. I got out a little bit more my sophomore year. I started jogging my junior year. Senior year, all in, let's go."
"I actually slowed my business down to speed it up."
She stepped back and rebuilt how the business ran, which for a creative was painful. It was also the year she cried the most, and not for the reason you would guess.
"I wasn't crying because of the failure. I cried from relief, because I understood why my business was functioning so poorly."
Year two: the $44,500 detour
Year one she was a great student. That turned out to be the problem.
"Year one I was a great student, but I wasn't a great executor, because I was trying to be a great student."
It was also the year she hedged. Unsure whether she was growing fast enough, she asked herself whether to renew TSP or go try other programs, and decided to do both.
"I went and dropped $20K on another program, $12K on another program, $5K on another, $7,500 on another. Real life numbers. And it was bad. It was really, really bad.".
Roughly $44,500 spent testing the alternatives. Her conclusion was the opposite of what she expected going in:
"Then I couldn't afford to leave TSP, because I need to make sure that I get everything I need and that I show up and execute."
Year three: getting off the sidelines
The hinge was a woman in the room pulling her aside and asking for her elevator pitch. Kylea gave it. The woman stopped her, because she had overheard Kylea mention at the table that she also manages an eight figure real estate portfolio with her husband.
"I was like, yes I do, but that's a different business. And she said: so what? When you introduce yourself, you're going to introduce yourself as Doctor, your name, I manage an eight figure real estate portfolio with my husband, and I also x, y, z."
"That changed the game for me. Taking ownership of my own accomplishments and releasing imposter syndrome, that's what year three looked like."
It was also the year she moved into the Craft House, and the year she stopped saying I can't do this because and started saying I have to do this because.
"Year three was the year where I said: this is real. I have a real business."
The reframe underneath all of it:
"We associate growth with working harder. Scaling is about strategy that most entrepreneurs just don't even know about."
Your Turn
Her one sentence description of the room:
"TSP is where black businesses go when they want to grow their business, in an ethical and community based way."
Four years ago Jennifer Jasper had a good product, real hustle behind her, and a growth plan that was never going to get her there. What she was missing was not talent or effort. It was people close enough to her business to see what she could not.
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