Ex-Prisoners: The Builders Behind Chris Wilson, Dave Dahl, Tracey Syphax and Weldon Long

Dave Dahl

Co-founder, Dave’s Killer Bread — Milwaukie, OR

Official links: Website · Facebook

Dave Dahl started working at his family’s Portland bakery at nine years old — and then walked away from that life into drug addiction, crime and prison.

The record, as The Takeout reports it, is four prison terms totaling about 15 years, on convictions that included armed robbery, assault, burglary and drug possession, served across Oregon, Massachusetts and Wyoming between 1987 and 2004.

During that fourth term, something shifted: he asked for psychiatric help, entered a computer-aided drafting program at Snake River Correctional Institution, excelled at it and ended up tutoring other prisoners in it.

He was released in late December 2004 — and within a week he was filling in for absent workers at the family bakery, NatureBake, because his older brother Glenn gave him the chance nobody else would.

“I was a four-time loser before I realized I was in the wrong game.”

That line — Dahl’s own, once printed on the back of every loaf — became the most honest packaging in the bread aisle.

In August 2005 he and his nephew Shobi took the first loaves of Dave’s Killer Bread to the Portland Farmers Market’s Summer Loaf festival, and they were an immediate hit; local grocers picked the bread up that year, Costco followed in 2009, and Inc. named the company one of America’s fastest-growing in 2011.

The company built its brand on second chances, hiring people with criminal records as a matter of policy. In 2015 Flowers Foods acquired Dave’s Killer Bread for $275 million — the four-time loser’s name still on every bag, his story still doing the selling.

The Takeout — “From Behind Bars To Baker: The Inspiring Story Of Dave’s Killer Bread”
Capital Research — “This Multi-Million-Dollar Company Built Its Success by Hiring Ex-Convicts”
Wikipedia — “Dave Dahl (entrepreneur)”

More from The Bourgeois Society: The full list  ·  Chris Wilson  ·  Dawon Matthews

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 The Bourgeois Society: The full list  ·  Weldon Long  ·  Dave Dahl

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 The Bourgeois Society: The full list  ·  Dave Dahl  ·  Marcus Bullock

Marcus Bullock

Founder & CEO, Flikshop — Washington, DC

Official links: Website · X

We’re inspired because Marcus Bullock was sentenced at 15 to eight years in an adult maximum-security prison — and what saved him was mail call. His mother wrote or sent photos every single day. He came home determined that no incarcerated kid would wait for a letter that never comes.

“My mom made a promise to send me pictures and letters and she saved my life with those letters and photos.”

Bullock came home to 41 job rejections. He built a painting and construction company that deliberately hired returning citizens, and its revenue launched Flikshop — the app that turns phone photos into real postcards delivered to any prison in America for about a dollar.

Flikshop now counts more than 180,000 registered users, has shipped over 500,000 postcards, and reaches some 2,700 facilities; it graduated from Techstars Anywhere and won backing from John Legend’s Unlocked Futures accelerator. His Flikshop School of Business teaches returning citizens entrepreneurship and coding, and Flikshop Angels lets supporters fund postcards so children can reach incarcerated parents.

Nasdaq — “Faces of Entrepreneurship: Marcus Bullock, Flikshop”
Black Enterprise — “Success Beyond Bars: Marcus Bullock and Flikshop”
Engine, #StartupsEverywhere — “Washington, DC: Flikshop”

More from The Bourgeois Society: The full list  ·  Dawon Matthews  ·  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 The Bourgeois Society: The full list  ·  Marcus Bullock  ·  Michael O’Connor

Frederick Hutson

Co-founder & CEO, Pigeonly — Las Vegas, NV

Official links: Website · LinkedIn · Instagram · X

We’re inspired because Frederick Hutson used his sentence itself as his market research. Released to a halfway house, he co-founded a company that hires other formerly incarcerated people and makes staying connected affordable for the families prison usually prices out.

“I was given an opportunity. I was given an opportunity to turn something around. I have to make this successful at this point or else it was all for nothing.”

Hutson, an Air Force veteran raised in Brooklyn, ran a marijuana operation grossing about $500,000 a year and lost it all to a federal sentence at 23. Serving 51 months, he found his business plan in the prison mail room.

Released to a halfway house, he co-founded Pigeonly with Alfonzo Brooks — the platform that forwards photos, letters and printed web content to incarcerated people and runs low-cost prison phone calls.

Pigeonly went through Y Combinator and raised $3 million; it has connected more than 300,000 incarcerated people with over 1.5 million loved ones and saves their families an estimated $10 million a year against legacy prison-communication prices. Hutson speaks and writes for second-chance hiring and reentry reform.

NPR Illinois — “Ex-Inmate Uses His Sentence to Create Successful Business Plan”
Yale Center for Business and the Environment — “From Prison to Pigeonly”
Verizon Newsroom — “Pigeonly CEO Shares Experience”

More from The Bourgeois Society: The full list  ·  Keidrain Brewster  ·  Shannon Ross

Shannon Ross

Co-founder, D’s Trucks; Founder & Executive Director, The Community — Milwaukee, WI

Official links: Website · LinkedIn

Shannon Ross did his freshman year at UW-Milwaukee, and then, in his own words, he “made a life-altering decision that led me to spend 17 years in the Wisconsin prison system.” Seventeen years is long enough to disappear.

Ross used them the other way: he wrote about his experiences, built a Buddhist meditation practice, designed and ran a coping-skills program at Stanley Correctional Institution, and fought through systemic obstacles to finish the bachelor’s degree in business administration he had begun before his arrest, graduating in 2017.

From inside, he founded The Community, an organization dedicated to fostering and showcasing the successes, humanity and agency of people with criminal records. Toward the end of his sentence he won a fellowship to a master’s program in sustainable peacebuilding at the University of Wisconsin-Milwaukee — and began his first semester a week before his release in 2020.

“My ultimate goal is to create a world I’d want my son to grow up in—a world I wish I had grown up in.”

A few months after coming home, Ross reconnected with his childhood friend Brian Adams, who had just left his job and wanted to start a business.

In March 2021 the two began operating D’s Trucks, with Adams behind the wheel and Ross overseeing business development — a trucking company built to hire system-impacted people and destigmatize the record so many employers stop reading at.

Ross still runs The Community alongside it, pushing pre-entry resources to people who are still incarcerated so that, as he learned the hard way, nobody has to figure reentry out alone. The man who once took from his community, as he puts it, has spent every year since giving back to it.

Fundbox (Small Business DNA) — “Shannon Ross of D’s Trucks and The Community”
Represent Justice — “Shannon Ross”
ListenNotes (Small Business DNA) — “Episode 1: Growing a Business and Hiring System Impacted Employees”
ActionCOACH Milwaukee — “Business Spotlight with The Community”

More from The Bourgeois Society: The full list  ·  Michael O’Connor  ·  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 The Bourgeois Society: The full list  ·  Shannon Ross  ·  Trent Griffin-Braaf

Weldon Long

HVAC Founder, Author & Sales Trainer — Colorado Springs, CO

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

Weldon Long describes his younger self in words we would not choose for him, so we will use his: a ninth-grade dropout who was in and out of state and federal prisons from 1987 to 2003 — 13 years inside in all, a three-time convicted felon.

The turn came on June 10, 1996, as he was starting a seven-year sentence, when he learned his father had died. He remembered their last conversation — Long complaining, blaming everybody else — and his father’s answer: “Your life could be worse… You’re still breathing.

And as long as you’re breathing you’ve got a shot to change your life. But you’ve got to do it.” Within hours, Long decided he would become a man his father could have been proud of, and the father his little boy deserved. He spent the rest of that sentence studying what successful people actually do.

“I was a ninth-grade dropout. I was a punk and a thug and a first-class loser.”

In January 2003 Long walked out for the last time, 39 years old, broke, to a halfway house and a homeless shelter. A small heating and air conditioning company hired him into sales; within about a year he had opened his own HVAC company, in 2004, knowing, by his cheerful admission, nothing about the mechanical side to this day.

He grew it from zero to $20 million in revenue in five years and onto the Inc. 5000 list of America’s fastest-growing private companies, bought Wright Total Indoor Comfort along the way, and went on to build and sell six companies in all.

The dropout became a New York Times bestselling author — The Power of Consistency, Consistency Selling, The Upside of Fear — and one of the home-services industry’s most sought-after sales trainers. His whole curriculum is the distance he traveled: from a cell to a shelter to a company of his own, one kept commitment at a time.

ServiceTitan (Toolbox for the Trades) — “Weldon Long: How an Ex-Con Became a Sales Superstar”
ACHR News — “Rags-to-Riches Speaker Weldon Long Motivates HVAC Dealers”
Becoming Your Best — “Breaking Free from Defeat and Despair with Weldon Long” (Ep. 351)

More from The Bourgeois Society: The full list  ·  Trent Griffin-Braaf  ·  Chris Wilson

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 The Bourgeois Society: The full list  ·  Tracey Syphax  ·  Weldon Long