Black Excellence: Faith, Grit & Second Chances — The Comebacks Behind Chris Wilson, Tracey Syphax and Trent Griffin-Braaf

Chris Wilson

Founder & Owner, Barclay Investment Corporation — Baltimore, MD

Official links: Website · Instagram · X

Chris Wilson grew up in Washington, D.C., in a violent neighborhood and a volatile home, and at 17 he was sentenced to life in prison after a shooting in which a man died. Behind bars, the book-loving teenager who once sold lollipops for profit refused to accept that his story was over.

He wrote what he called his Master Plan — a list of everything he intended to accomplish — earned his GED and college degrees, learned languages, and studied how businesses actually run, from bookkeeping to taxes. After 16 years inside, Boston College reports, he convinced a judge to grant him his freedom, on condition he finish the plan.

He came home to Baltimore and did exactly that, founding Barclay Investment Corporation, a residential and commercial contracting social enterprise, alongside a furniture restoration company, and writing the memoir The Master Plan: My Journey from Life in Prison to a Life of Purpose.

"Everyone else thought I was crazy, but I chose to believe this master plan was what was going to set me free."

Wilson built Barclay to work the way his second chance worked for him. Boston College notes the company works closely with local workforce and social service providers to connect unemployed Baltimore residents with clients who need services, and other profiles stress that his businesses seek to employ formerly incarcerated people.

Through his book, university talks — including Boston College's 2019 First Year Convocation keynote — and speaking and media appearances, he now teaches other people, including people still inside, how to write and live their own master plan.

Boston College — “'The Master Plan' author Chris Wilson to address BC Class of 2023”
Bond Street — “Second Chances: Finding Entrepreneurship After Prison”
The Johns Hopkins News-Letter — “Entrepreneur guest lectures at class on Baltimore public health”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Onyi Odunukwe  ·  Dawon Matthews

Dawon Matthews

Owner, Goodies Soul Kitchen — Houston, TX

Official links: LinkedIn · Instagram

Dawon Matthews, a Philadelphia native, excelled in high school, then, as CNBC Make It reported, was charged with aggravated assault after a college party brawl, was expelled, served six months in jail, and, while on probation, was charged with a DUI. He describes going in and out of the system after that.

He still earned an associate degree from Manor College and a bachelor's in business from La Salle University — and then applied to more than 200 jobs with no luck. So he built his own work.

In 2017 he co-founded Wonderful Cleaning in the Philadelphia area, which reached about $12,000 a month by its second year; R&R Junk Removal followed in 2020 and brought in more than $100,000 in its first year.

He reinvested in real estate, building a portfolio of 16 Philadelphia-area properties bringing in about $11,000 a month in profit, before moving to Houston in 2024.

"Once they see a felony behind a person they don’t even care about what credentials you got. You’re just not accepted in that society,"

In Houston, after losing more than $170,000 on a failed nightclub venture, Matthews took a $40,000 loan and launched Goodies Soul Kitchen in August 2024 with partner Jessica Ahwash.

He had no restaurant experience and had to learn to cook when his chef quit a month in, yet the downtown truck brought in just over $1 million in gross revenue in 2024, according to documents reviewed by CNBC Make It, and more than $665,000 more in 2025.

CNBC also reports he is committed to employing recovering addicts and people with criminal records, and he has since opened a second truck, Birds and Buns, while planning a brick-and-mortar Goodies.

AfroTech — “Employers Wrote Him Off After Incarceration, So Dawon Matthews Became An Entrepreneur And Launched A Food Truck That Has Made Over $1.6M”
CNBC Make It via NewsBeep — “How this 32-year-old's Houston food truck brings in over $1 million a year”
BlackBusiness.com — “From Prison to Profit: Black Entrepreneur Builds $1 Million Food Truck Business”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Chris Wilson  ·  Keidrain Brewster

Keidrain Brewster

Founder & CEO, Brewster Logistics — Dallas, TX

Official links: Website · Facebook · Instagram · X

Keidrain Brewster entered the Texas Department of Criminal Justice at just 17 and served 13 years, released in 2014. While he was inside, Orijin reports, he lost his younger brother and his mother — losses that became turning points.

He earned his GED and, in Orijin's words, took every course available, deciding to invest in himself while he was still incarcerated. After release he earned his CDL and started Brewster Logistics with a single truck — Face2Face Africa describes it as one dually truck with a flatbed trailer that he drove himself.

From that one truck, Dallas Doing Good reports, the company has grown into a fleet of ten trucks employing more than 15 people. Along the way he became a bestselling author, writing From the Rec Yard to the Streets and From the Streets to the Suites about the journey from a prison yard to a CEO's office.

"I don’t tell you these stories as a victim, but as someone who understands the significance of change,"

Brewster's work now runs in both directions: a business, and a movement to bring others home well. He founded the Big Reform Movement and, per Voyage Dallas, a nonprofit, From the Rec Yard to the Streets, providing resources, CDL training and mentorship to people coming home from prison.

He speaks inside correctional facilities — CoreCivic reports he addressed more than 300 residents approaching release at its Whiteville, Tennessee facility — advocates for educational tools in the penal system, employs people with criminal backgrounds, and in 2025 became a Texas Certified Re-Entry Peer Specialist, according to his official site.

Dallas Doing Good — “Turning Trials into Triumph: Keidrain Brewster's inspiring journey from prison to social impact”
Orijin — “How Keidrain Brewster Drove His Life from Prison to Prosperity” (Second Chances@Work)
CoreCivic — “Motivational Speaker Keidrain Brewster Inspires Residents in Tennessee to Embrace Positive Change”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Dawon Matthews  ·  Tracey Syphax

Tracey Syphax

Vice President & COO, Phax Group Construction & Design LLC — Trenton, NJ

Official links: Website · X

Tracey Syphax writes, in his own JustLeadershipUSA essay, 'I spent seven years in prison, 17 years in the street, and 23 years in business and I count all of those years as experience.' JustLeadershipUSA's summary of an Axios interview describes him as a drug-addicted hustler who remade himself after prison.

When he came home in 1993, that summary says, he found work as a roofer, worked his way up, and later became CEO of his own company, which generated $1.8 million seven years after he founded it.

In his essay he says he founded two million-dollar corporations — Phax Group Construction & Design LLC and Phax Group, LLC, a Trenton real estate development company — after attending the Million Man March in 1995 and taking its message to heart: if you couldn't find a job, go home, create one, and build economic power in your community.

"My job is to put a new face on reentry by mentoring returning citizens on how to start and operate a business."

Syphax was selected as a 2014 White House Champion of Change for reentry and employment, from an unprecedented 900 nominees, and in December 2017 Governor Chris Christie pardoned him.

He authored the memoir From the Block to the Boardroom, founded the Minding Our Business program mentoring sixth- and seventh-graders on starting businesses, and created Reentry Ventures, an entrepreneurship program for returning citizens whose pilots, he writes, produced jobs and businesses.

JustLeadershipUSA lists him as a board member of the African American Chamber of Commerce of New Jersey, and notes he was the Princeton Regional Chamber's first African American Entrepreneur of the Year, in 2011.

JustLeadershipUSA — “My job is to put a new face on reentry.”
JustLeadershipUSA — “Tracey Syphax” (leader profile)
PR Newswire via ForImmediateRelease — “Gov. Chris Christie Grants Clemency to Trenton Businessman Tracey D. Syphax”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Keidrain Brewster  ·  Trent Griffin-Braaf

John Imah

Co-Founder & CEO, SPREEAI — Los Angeles, CA

Official links: Website · LinkedIn · Instagram · X

John Imah grew up in Dallas as the son of Nigerian parents who, TechMoonshot reports, pushed him toward lawyer or doctor — tech wasn't even on the radar. At seven, he dismantled the family computer out of curiosity and put it back together.

One syndicated profile notes that as a kid he sometimes felt like an outsider for being the 'nerd' who also loved art and fashion, enduring bullying for that blend of interests. By his early teens he had taught himself to program.

Wikipedia and his official biography agree on the sequence: he launched and sold his first technology business at 15, followed by a second venture, in mobile gaming, at 16. He went on to the University of Texas at Arlington and to roles at Samsung, Take-Two Interactive, Amazon's Twitch, Meta and Snap, where he was Head of Partnerships for gaming.

In 2023 he co-founded SPREEAI to merge that technology career with his lifelong passion for fashion.

"I was always looking for a way to merge tech and fashion,"

SPREEAI, which builds photorealistic AI try-on and fit technology for fashion retail, reached a reported $1.5 billion valuation by 2025, with Naomi Campbell on its board and partnerships including the Council of Fashion Designers of America. In 2025 Imah was named to Observer's AI Power Index and AfroTech's Future 50 and was an Inc. Best in Business honoree.

Wikipedia notes that, following his mother's death from breast cancer, he has supported the American Cancer Society and STEM education initiatives in Nigeria and the United States, and BusinessDay reports he established a scholarship fund at the University of Texas at Arlington.

Wikipedia — “John Imah”
JohnImah.com — “John Imah Press & Media | Interviews, Biography & Photos” (official)
TechMoonshot — “From Teenage Prodigy to $1.5B Unicorn: How John Imah Is Solving Fashion's Most Expensive Problem”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Jhalesa Seymour  ·  Karlton Dennis

Karlton Dennis

Founder & CEO, Tax Alchemy — Orange County, CA

Official links: Website · Facebook · Instagram · X

Karlton Dennis first chased a professional sports future. He earned a degree in kinesiology from California Polytechnic State University, San Luis Obispo, where he played Division I college football, according to All American Speakers.

When injuries ended his football plans, his own book site says, he entered wine sales and quickly realized the downside of high-tax W-2 income — and the School of Hard Knocks podcast description adds that he found himself broke, working odd jobs as a personal trainer and wine salesman.

That detour sent him back to the family business: he joined his mother's firm, Karla Dennis and Associates, developed a talent for simplifying advanced tax strategy, and earned his Enrolled Agent credential, which authorizes him to represent taxpayers before the IRS in all 50 states.

From that start in his mother's office, he founded Tax Alchemy and, in roughly six years, grew it into a multi-eight-figure firm.

"Every dollar you overpay in taxes is a dollar that can’t be invested, can’t buy back your time, and can’t be passed down to your children. Keeping more isn’t greed—it’s stewardship"

Tax Alchemy now employs more than 50 professionals and, per his book site, has helped more than 2,000 high-net-worth clients collectively save more than $100 million in taxes; All American Speakers puts his wider client work at more than 10,000 clients.

Dennis has made teaching the second half of the business: he hosts the Tax Free Living podcast, built what his book site calls the largest tax strategy channel on YouTube, with over 1.1 million subscribers, and authored The Art of Legal Tax Avoidance — all aimed at making elite tax planning accessible to everyday entrepreneurs, not only the wealthy.

The Art of Legal Tax Avoidance — official book site (Karlton Dennis biography)
All American Speakers — “Karlton Dennis” (biography)
School of Hard Knocks Podcast via Podcast App — “Karlton Dennis | Makes $10M/Year, Pays Nothing in Taxes, and Teaches You How” (episode description)

More from Bourgeois Society: Faith, Grit & Second Chances  ·  John Imah  ·  Lynnwood Bibbens

Lynnwood Bibbens

Founder & Executive Chair, ReachTV

Official links: Website · X

Lynnwood Bibbens grew up in a working-class New Jersey town where, the School of Hard Knocks newsletter recounts, he learned the value of hard work from his grandfather, who held a 9-to-5 job and ran a garbage route on the side.

In college he was brought in to fix a friend's chaotic shipping department, became its top sales rep within six months, then an equal partner; three years later they sold the company to its biggest customer.

In the mid-1990s he launched an internet company, scaling it from six deals a day to $40 million in revenue in 18 months and $100 million 18 months after that, exiting before the dot-com crash, then grew New England Technology to $100 million in three years and built businesses to a $250 million run rate.

He later moved into film finance, helping finance film and TV projects, before founding ReachTV in 2016, per Ad Age.

"Live sports in general, whatever platform it’s on, live sports is going to dominate because that’s the one thing that you have to watch then,"

ReachTV became the leading travel media network in the country: NATPE lists more than 2,500 screens, 50 million-plus monthly viewers and 90-plus U.S. airports, as the preeminent Black-owned, MBE-certified airport television network.

When CNN exited the airport business in 2021, ReachTV took over its screens, Ad Age reports, and Bibbens has since pivoted the network to live sports — he told Beet.TV that live sports now accounts for about 60% of programming.

In the company's next phase, Stagwell announced Rachel Jacobson as CEO of ReachTV, with Bibbens transitioning to the newly created role of Founder/Executive Chair to continue building the company's future.

Beet.TV — “ReachTV’s Lynnwood Bibbens: Live Sports Now Accounts for Majority of Airport Networks’ Programming”
School of Hard Knocks (Beehiiv) — “How Lynnwood Bibbens Turned Hustle Into a $2B Empire”
NATPE Global — “Speaker Lynnwood Bibbens”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Karlton Dennis  ·  Onyi Odunukwe

Trent Griffin-Braaf

Founder, GB Logistics & Tech Valley Shuttle — Albany / Capital Region, NY

Official links: Website · LinkedIn · Instagram

Trent Griffin-Braaf was born in the Bronx, lost his father at about nine, and moved upstate with his mother. The Center for Community Alternatives says that after a regrettable decision as a teenager involving narcotics sales after high school, he served a prison sentence and faced felony discrimination on release.

What he did next is the heart of his story: he started in the hotel industry as a part-time houseperson — Jails to Jobs describes the first job as cleaning toilets at a Marriott — and rose to general manager within six years.

In 2016 he founded Tech Valley Shuttle, turning a hotel shuttle into a community transportation provider aimed at combating poverty, and during the pandemic he launched GB Logistics, which held an Amazon last-mile delivery contract until 2023. He was named a Forbes Next 1000 entrepreneur and the SBA's 2023 Small Businessperson of the Year for upstate New York.

"I like to think of myself as a hope dealer, I understand the importance of going back and letting people know what's possible. If you have hope, you have something you're striving for, and you know it's possible for you,"

Griffin-Braaf built second chances into his hiring model. The Center for Community Alternatives reports his companies employ 100% underserved individuals — 80% with justice involvement and 20% with disabilities — and that Tech Valley Shuttle became the first Black-owned business named one of the best places to work by the Albany Business Review.

He created the Roadmap to Success program to help justice-involved people achieve socioeconomic mobility, provides mentorship to minority entrepreneurs and free rides for people who are unhoused and veterans, per the Rensselaer County Chamber, and still travels to correctional facilities to coach residents approaching release.

Center for Community Alternatives — “Trent Griffin-Braaf” (board profile)
CoreCivic — “Entrepreneur with Lived Experience Provides Residents a Roadmap to Hope and Success”
Jails to Jobs — “Trent Griffin-Braaf creates Roadmap to Success to help formerly incarcerated individuals succeed”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Tracey Syphax  ·  Jhalesa Seymour

Jhalesa Seymour

Founder, Salt.XO — Miami, FL

Official links: Website · Instagram

Jhalesa Seymour's mother raised five kids on about a $30,000 salary — a fact Seymour returns to again and again.

In her Business Insider as-told-to essay, quoted by Moneywise, she says that when she was offered a college teaching job paying about that same $30,000, she knew she needed more, because her mother had always exposed her to a better way of life.

As a senior at the University of Central Florida, frustrated by feminine hygiene products loaded with synthetic chemicals that irritated her, she started handcrafting all-natural soaps and washes, handing them out free on campus. Urban Magazine confirms she launched Salt XO in 2018 with no investors and just $67.

In 2018, she told Business Insider, she made $154,000 making soaps out of her apartment; the next year, the company made $1 million in profits, and since then it has had more than $16 million in sales — and she became, Moneywise reports, a millionaire by 25, the first in her family story she tells.

"I didn’t see products on the shelf that felt like they were made with me in mind,"

Today Seymour pays herself a salary from Salt.XO and reinvests the rest of the profits into the team and the business, rather than treating company revenue as personal money — a discipline she teaches publicly.

As a mother of two boys, she told Business Insider that teaching her kids about money is as important as literacy, raising them with habits she had to learn on her own, sometimes through mistakes.

In April 2025 Salt XO marked seven years with its 'Sacred Seven' anniversary event in Miami, building on the 'SaltBaes' customer community that propelled the brand by word of mouth.

Urban Magazine — “Salt XO Celebrates Seven Years of Feminine Wellness and Empowerment”
Moneywise — “She turned $67 into an 8-figure business”
Business Insider via AdvisorStream — “I own a multimillion-dollar business and believe teaching my kids about money is as important as literacy. Here's how I'm doing it.”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Trent Griffin-Braaf  ·  John Imah

Onyi Odunukwe

Founder & CEO, Glo Tanning — Dallas, TX

Official links: Website · LinkedIn · Facebook · Instagram · X

Onyi Odunukwe is a Dallas-based entrepreneur, the son of Nigerian immigrant parents, who made an unlikely bet in an industry with almost no Black representation.

COSIGN Magazine recounts that, while attending the University of Arkansas in Fayetteville, he noticed how normalized tanning culture was there — and how inconsistent the customer experience was — while he was already operating a supplement store in a space too large for its original purpose.

He signed his first lease at 21 and opened at 22, committing fully to one business rather than scattering his attention. Rather than testing the waters with something minimal, COSIGN says, he invested roughly a quarter of a million dollars into the first build-out to create the most premium tanning salon in his market.

That single, focused bet — a salon concept first called Glow — became the foundation for everything that followed, including commercial real estate ownership.

"Eliminating ego has undoubtedly been one of the most impactful changes I’ve made, and it has played a pivotal role in our business’s growth and improvement."

That foundation is now Glo Tanning, founded in 2010 per the company's releases, with 105 locations open and 250 in development, offering tanning, red light therapy, infrared sauna and skincare in spa-like studios, and franchising since 2020.

In Shoutout DFW, Odunukwe says he began franchising so others could learn from the mistakes he made in his early 20s, and that his focus is empowering staff to become strong leaders and potential future owners. COSIGN reports his portfolio has grown into nearly 30 commercial properties across several states, built on owning the spaces his businesses operate in.

COSIGN Magazine — “Onyi Odunukwe Built a $100M+ Empire Starting With a Tanning Salon (26 Businesses Later)”
Shoutout DFW — “Meet Onyi Odunukwe | CEO and Founder of Glo Tanning”
ACCESS Newswire via FinancialContent — “Glo Tanning Brings Luxury Wellness and Skincare Experience to Little Rock”

More from Bourgeois Society: Faith, Grit & Second Chances  ·  Lynnwood Bibbens  ·  Chris Wilson