Podcast Summary: Black Entrepreneur Experience – Episode 533
Title: AI for Social Justice: Roger Roman's Mission for 1 Million Expungements
Host: Dr. Frances Richards, Chief Encouraging Officer
Guest: Roger Roman, CEO & Co-founder of Legalese
Date: January 21, 2026
Main Theme & Episode Overview
This episode highlights tech entrepreneur Roger Roman’s journey and mission to use AI for radical social impact, focusing especially on expungement of criminal records. Roger, CEO and co-founder of Legalese, shares his personal backstory, the vision behind Legalese, and his goal to facilitate 1 million expungements by 2030. The conversation covers entrepreneurship lessons, funding challenges, the intersection of AI and justice, and actionable advice for Black founders.
Key Discussion Points & Insights
Roger Roman's Story and the Birth of Legalese
- Personal Journey: Grew up on Chicago’s West Side, with high expectations for academic achievement. Was pushed towards law but found entrepreneurial passion in tech after a circuitous journey through real estate and failed startups.
- Founding Story: Legalese was co-founded with Lawrence Blackmon, originally sparked by Lawrence’s own experience needing an expungement, and his realization (as a practicing attorney) of the inefficiency and expense of existing expungement processes.
- "Expungement as Justice": Emphasized that expungement is a right, enshrined in law, but not widely accessed due to lack of awareness or resources.
"Expungements are something that a lot of people don't know about. But a third of the population, over 70 million people, have a criminal record or some, some blemish. [...] And it's not a loophole or workaround—it's written into law."
—Roger Roman [03:09]
Lessons from Failure; The "Failing Forward" Mindset
- Serial entrepreneur with several failed startups: Critical to learn and adapt from failures.
- Resilience vs. Pivoting:
- Importance of knowing when to persist and when to pivot:
"There's a point between persistence and resiliency and knowing when to pivot... If you can figure out that, you can have success as an entrepreneur. Resiliency is probably the strongest muscle you need."
—Roger Roman [09:31]
Leadership & Funding Challenges for Black Entrepreneurs
-
Delegation as a Key Skill: Early tendency to try to do everything himself led to stress and limited growth.
"You can't do it all by yourself. You're going to need a team, you're going to need to empower people and trust people."
—Roger Roman [24:10] -
Funding Journey:
- Bootstrapped initially; joined Techstars accelerator, then funded by a mix of grants and investments (total ~$1.1M).
- Stresses necessity of homework and targeting "warm intros" over cold pitches; chose investors aligned with Legalese's mission.
"In my previous experience, I've struggled to raise... When you come with the right solution and do your homework on investors... you save yourself rejection."
—Roger Roman [19:45] -
Advice for Aspiring Founders:
- Work on your business outside of a 9-to-5 before quitting
- Keep personal financial stability until the business is viable
"Until it's generating revenue, it's more of a hobby than a business... focus on making sure you have some stability before you leap."
—Roger Roman [27:38]
AI, Social Justice & Mission-Driven Tech
- AI is at an inflection point—potential for harm, but even greater potential for good in the right hands.
- Legalese leverages AI to automate and scale expungements, removing complexity and cost barriers.
"We're using AI to kind of solve this problem and help a lot of people out. Used correctly, I think it can be incredibly empowering—it's like the calculator for the legal system."
—Roger Roman [13:27] - Cautions against blind adoption—treat AI as a tool, not a crutch.
Legalese's Customer Base & Expansion
-
Ideal User:
- Anyone with a criminal record blocking social mobility (employment, housing, volunteer opportunities), usually unable to afford a lawyer or daunted by process complexity.
- Some want the record cleaned simply for peace of mind.
"It's the person who is looking to remove this blemish... maybe it was 10 years ago, maybe they weren't convicted—most people don't know any interaction with law enforcement can come up on your record."
—Roger Roman [16:03] -
Rollout & Demand:
- Initially launched in Mississippi; huge demand led to acceleration of plans (upcoming: CA, TX, GA, IL, MD).
- Over 3,000 sign-ups nationwide after initial PR.
"We thought we’d get a few hundred people... to our surprise, we had over 3,000 sign up from all over the country."
—Roger Roman [40:43]
Impact Stories
- Helped a Mississippi CNA clear a minor domestic violence record, enabling her to pursue becoming a registered nurse.
- Assisted a small business owner in clearing old charges so he could volunteer as a youth football coach for his son.
"Those are real people, faced with real things, and for some it’s even more extreme—these records hold back whole lives."
—Roger Roman [39:11]
Mental Health & Work-Life Balance
- Stresses importance of downtime and presence with family; warns that ignoring mental health (and physical health) can lead to burnout.
"You're not going to survive if your mental health isn't taken care of... find those moments of peace, zoom out, and be fully present with your family."
—Roger Roman [33:20] - Admits meditation often turns into naps for him—a bit of humor that lightened the tone.
Legacy & Empowerment
- Roger wants to be remembered as someone who not only achieved, but empowered others and built things that lifted people up.
"Empowerment—that’s the word. Did I build something that actually helped people? Did I empower? That’s the legacy."
—Roger Roman [36:46]
Notable Quotes & Memorable Moments
- On AI & Access:
"I like to think of us as the TurboTax for justice tech—helping you do what you could only do with a lawyer in the past."
—Roger Roman [43:24] - On Entrepreneurship:
"Keep that day job. Learn from me—keep that steady foundation and build slowly."
—Roger Roman [28:40] - On Failure:
"Failing forward is the correct term. If you’re not taking something from it, it’s really a loss."
—Roger Roman [09:33] - On Inspiration:
"Malcolm X... is the embodiment of what we're building—someone who had a rough start and changed his life. Second chances are our ethos."
—Roger Roman [11:56] - Favorite Tool:
"Used to be Notes. I would say ChatGPT at this point, I’m just being honest."
—Roger Roman [45:11]
Important Timestamps
- [02:30] — Roger’s entrepreneurial journey & Legalese origin
- [09:31] — "Failing forward": Lessons from failure and how to pivot
- [13:22] — How Legalese uses AI and a vision for ethical, empowering artificial intelligence
- [16:03] — Who is Legalese for? Defining the ideal expungement client
- [17:32] — Overcoming funding barriers, Black founder funding realities
- [19:45] — How Techstars accelerated Legalese and fundraising strategies
- [23:19] — Leadership lessons & the dangers of doing it all yourself
- [27:38] — Funding realities, creative solutions, and advice on starting part-time
- [32:43] — The importance of mental wellness as an entrepreneur
- [35:28] — Building a legacy of empowerment
- [37:27] — Customer success stories and direct impact
- [40:33] — Legalese expansion plans
- [42:42] — Roger’s vision for the future of Legalese
- [44:22] — Rapid fire round
Rapid-Fire Round Highlights
- First thing in the morning: "Drink a cup of water." [44:44]
- Book that changed your life: "The Autobiography of Malcolm X." [44:48]
- Favorite app: "ChatGPT, if I’m honest." [45:11]
- Most admired entrepreneur: "John H. Johnson." [45:31]
How to Connect with Roger Roman & Legalese
Website: legalease.com (all social links there)
Roger on LinkedIn: Roger Roman (Founder of Legalese)
Final Thoughts
Roger Roman’s approach fuses tech innovation with a deep commitment to justice and accessibility. Legalese’s mission—to automate and democratize expungement—serves as a powerful example of technology tackling entrenched social barriers. Roger’s story offers inspiration, practical strategies, and candid insights for other Black entrepreneurs and founders breaking new ground.