From Gum-Selling Teen to Trailblazing Coach — Shai Boston
Read time: 4.7 minutes
Welcome back to Spotlight Hustle, where we shine a light on Black women rewriting the rules of leadership, wellness, and business with authenticity and heart.
Today’s feature is on Shai, a leadership trainer, podcaster, and unapologetically real voice in the talent development space. Her story is bold, brilliant, and refreshingly unfiltered — a reminder that freedom isn’t found in perfection, but in truth.
Claim your seat today and join the movement
Feature Story: Raised in the Bay, Built for the World
Born and raised in Oakland, California, Shai’s childhood was steeped in culture, activism, and community. The Bay Area’s rhythm — part Silicon Valley drive, part soulful grit — shaped her outlook on life and leadership.
Her mother and grandmother taught her strength, grace, and self-advocacy. Her teachers — Ms. Thomas, Ms. Wooten, and Ms. Sumler — nurtured her voice, creativity, and confidence.
“They taught me to stand tall in my heritage and never be afraid to take up space,” she says.
That foundation, combined with a fierce curiosity and love for people, shaped the woman Shai became: bold, compassionate, and resilient.
The Moment Everything Changed
Shai didn’t set out to be an entrepreneur — she became one through conviction.
For years, she trained and coached others inside corporate systems that didn’t always honor her boundaries or brilliance. But after one final boundary was crossed, she decided enough was enough.
She walked out of a workshop at 5:00 p.m.
By 5:15, her resignation email had been sent — complete with a photo of her hitting “send.”
“That was my perfect storm,” she says. “When I was done, I was done.”
That bold act birthed her business: a platform rooted in empowerment, strategy, and the belief that everyone deserves to lead from their authentic self.
Challenges & Resilience: From ‘Pushing Through’ to Healing Through
Shai’s honesty about her mental health journey is powerful.
Depression. Anxiety. PTSD. Grief.
She’s lived through them all — and learned not to pretend she’s “fine.”
“The pushing through almost broke me twice,” she shares. “I had to stop performing strength and start honoring my humanity.”
Therapy, faith, and her support system saved her life — literally.
Now, she models a new kind of resilience: one rooted in feeling, acknowledging, and working through pain, not around it.
“When life hits hard, I feel the feels. Then I say, ‘Alright, time to put on the thong and get to work.’”
It’s her signature mix of humor, truth, and self-empowerment — and it’s exactly what makes her story unforgettable.
Mindset & Motivation
Shai stays grounded through faith, medication, and radical self-awareness.
“Faith reminds me who I am. Meds help me manage my anxiety, depression, and ADHD. Together, they keep me peaceful and productive.”
Her “why” is deeply personal:
“Me. Not in a selfish way — but because I deserve to feel good in my work and in my skin.”
She’s late-diagnosed with ADHD and proudly neurodivergent — a truth she embraces as both challenge and gift. Her creativity, big-picture thinking, and hyperfocus have become her superpowers.
And her mindset? Grounded and flexible.
“I’ve learned to do things at my own pace. Flexibility and adaptability are game changers.”
Identity & Representation
In a field where Black women are still rare — especially in talent development and travel training — Shai’s presence is power.
“There are very few of us leading classrooms,” she says. “That’s why I show up. Representation matters. Presence changes minds.”
She shows up where no one expects her to be. Speaks on topics others shy away from.
And she makes sure, in her own words, “when I’m in the room, folks know I was in the room.”
Her definition of success?
“I measure it for myself. If success doesn’t amplify my faith and peace, I redefine it.”
Routines & Practical Hustle
There’s no such thing as a “typical” day for Shai — ADHD doesn’t work like that.
But there’s rhythm in her chaos:
-
The Pareto Method: Timers help her manage focus and avoid hyperfixation.
-
Water & Food Reminders: “As a neurodivergent woman, I will forget to eat. Alarms help.”
-
Spiritual Start: Morning Bible study and journaling clear her mental space.
Rest, for Shai, is sacred and varied — a Korean drama, a long bath, a drive, or total silence.
“Rest doesn’t have to look the same every day. It just has to be real.”
Wisdom & Advice
To her younger self:
“Build your faith and build your tribe. They’ll catch you when you fall and reign you in when you go too far.”
Myth to bust:
“Not everyone is meant to be an entrepreneur. And that’s okay.”
She believes deeply in teamwork — the right team makes the dream sustainable.
“Entrepreneurship is not the soft life. It’s hard work, lonely sometimes, and not for everyone.”
Her biggest lesson to women:
“You can’t fake confidence forever. Believe in yourself for real — the quiet kind that doesn’t need to announce itself.”
Looking Ahead
Freedom is the theme of this next chapter.
Shai is preparing to launch her second podcast, Black Girl, Brown Girl…Squirrel!, the first of its kind for Neurodivergent Black and Brown women.
She’s also revamping her coaching and training programs, developing digital products, and planning two summits in 2026 — all while working toward certification as a Neurodivergent Coach.
Her legacy?
“When people say my name, I want them to feel love, authenticity, and transformation.
I want them to say, ‘She helped change my life.’”
Rapid-Fire Round
Coffee or tea? → Both!
Morning or night? → Night owl.
One word for this season? → Free.
Favorite podcast/book? → The Dating Detectives + The Year of Yes by Shonda Rhimes.
Mantra? → “Make sure of the more important things.” — Philippians 1:10
Favorite activity? → Let’s just say… I plead the fifth! 😉
Discipline hack? → The Pareto Method — for everything.
Why We’re Excited
At this year’s Top 100 Most Powerful Black Women Summit, Shai will bring laughter, insight, and unfiltered truth about faith, freedom, and neurodivergent leadership.
Tickets are FREE.
Spotlight Hustle Insights Newsletter
Mindset, Growth, and Success Stories for Black Women in Digital Business.




Responses