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Reentry Reimagined

AI-assisted planning and support for justice-impacted reintegration

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The Reentry Gap: A Broken System Demands Change

Reentering society after incarceration is challenging and the system meant to support that transition is often fragmented, slow, and difficult to navigate. Many individuals struggle to access stable housing, employment opportunities, essential documents, and coordinated support services, increasing the risk of unemployment, instability, and recidivism.

MyReentry helps bridge this gap by connecting individuals, families, service providers, and community resources through one integrated reentry support platform. By improving access to jobs, housing, and guidance, we create structured pathways for successful reintegration and stronger, safer communities.

Built By Us For Us

MyReentry delivers an integrated, four-component platform

Secure Resident App for Jail/Prison Tablets

Includes smart reentry mapping, a reentry plan builder, readiness tracker, digital wallet, recidivism mitigation and early opportunities to connect with reentry providers.

Support Dashboards

Provides corrections staff, reentry navigators and family with analytics, progress tracking, and support suggestions.

Partner Portals

Connects employers, housing providers, faith groups, and reentry providers to participants profiles in real time.

Post-Release App and AI-Coach

Offers individualized guidance after release, addressing employment, housing, health, and social-support needs.

See Platform Features

Your Digital Bridge to Freedom

Reentry Mapping

Reentry Plan Builder

Mitigation Opportunities (RiskAware)

Reentry Readiness Tracker

Post-Release App Homepage

SmartMatch Connection with Employers, Housing, and Resources

Partner Portals for Reentry Providers

Support Dashboards for Family, Navigators and Staff

AI Companion Coach

Digital Wallet for Essentials

We Are Building the Future

PPA Filed

MyReentry LLC Registered

Silicon Valley - Justice Impacted Partnership

Nationally Recognized Team Assembled

Platform Development Underway

Pilot Program Campaign (Q2 2026)

National Media Campaign (Q3 2026)

MEET THE FOUNDERS

Aaron Edward olson

Co-Chief Executive Officer (Co-CEO)

Product Vision, Platform Strategy, and Narrative Leadership

Aaron Olson is the founder of MyReentry and serves as Co-CEO, leading product vision, platform strategy, and long-term innovation. An award-winning journalist, reentry strategist, and creator of The Abolition Christian Podcast, Aaron brings over 20 years of lived experience inside the prison system, giving him an unparalleled understanding of the structural failures in reentry. From within the carceral system, Aaron operates as the primary architect of MyReentry's system design, shaping:
  • Platform architecture and workflow
  • User experience and human-centered design
  • Core product strategy and feature prioritization
  • The philosophical foundation behind MyReentry's readiness and opportunity-based model
He serves as the bridge between lived experience and technical execution, ensuring that every aspect of the platform reflects the real needs, behaviors, and challenges of people transitioning home. Aaron's leadership positions MyReentry as both product and movement redefining how reentry is understood and built.

tracy michelle olson

Chief Operating Officer (COO)

Operations, Strategy Execution, and Organizational Infrastructure

Tracy Olson serves as Chief Operating Officer, overseeing day-to-day operations, execution strategy, and organizational infrastructure. With over 15 years of experience in social services and a background in business and entrepreneurship, Tracy brings strong expertise in:
  • Administrative leadership
  • Systems coordination
  • Case management and behavioral support environments
  • Organizational development and compliance
A formerly incarcerated professional, Tracy plays a central role in:
  • Business planning and investor readiness
  • Internal operations and workflow systems
  • Strategic coordination across the founding team
  • Partner communications and relationship management
She is the operational backbone of MyReentry--ensuring that vision turns into structured, scalable execution.

Christopher Blackwell

Chief Communications Officer (CCO)

Media Visibility, National Narrative Strategy, and Investor Outreach

Christopher Blackwell serves as Chief Communications Officer, leading media, national narrative strategy, and investor outreach. He is the co-founder and Executive Director of Look2Justice, a grassroots organization that provides peer-led civic education and empowerment programs to impacted persons and their families to navigate legislative, policy, and narrative change. His writing has been featured in:
  • The New York Times
  • The Washington Post
  • and other top publications
Currently incarcerated in Washington State, Chris brings a powerful and credible voice to:
  • Public narrative around incarceration and reentry
  • Media engagement and national storytelling
  • Investor and public-facing messaging
He leads:
  • Brand narrative development
  • Media outreach and strategic communications
  • Public trust and awareness building
Chris ensures MyReentry is not only built--but seen, understood, and supported at scale.

Devon Adams

Co-Chief Executive Officer (Co-CEO)

External Leadership, Partnerships, and Institutional Strategy

Devon Adams serves as Co-CEO of MyReentry, leading external strategy, partnerships, and institutional engagement. As Co-Executive Director of Civil Survival, Devon brings deep experience in: Reentry systems and policy Government and Department of Corrections relationships Community-based program development Equity-driven leadership A formerly incarcerated leader, Devon plays a critical role in positioning MyReentry for real-world adoption, ensuring the platform aligns with:
  • Community needs
  • Institutional requirements
  • Scalable partnership opportunities
He leads:
  • Strategic partnerships (nonprofits, workforce, housing, DOC)
  • Pilot program development
  • Stakeholder engagement and credibility building
  • External representation with funders and agencies
Devon's leadership ensures MyReentry is not only visionary--but deployable, trusted, and scalable.

Massimo Bardetti

Chief Technology Officer (CTO)

Platform Architecture, Engineering, and AI Systems

Massimo Bardetti serves as Chief Technology Officer, leading the design and development of the MyReentry platform architecture. Based in Silicon Valley, Massimo has engineering experience with:
  • Microsoft
  • Amazon
  • Multiple AI-focused startups
He is responsible for building a secure, scalable, and intelligent system that supports:
  • Real-time personalization
  • Cross-platform integration
  • AI coaching and adaptive workflows
  • Long-term infrastructure for national scale
Massimo also leads the development and protection of MyReentry's proprietary algorithmic systems, including:
  • Smart matching
  • Readiness modeling
  • Adaptive reentry planning
His leadership ensures MyReentry is not just functional--but technically differentiated and enterprise-ready.

Were Ready to Scale. You Can Help.

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    From Lived Experience to Lasting Impact

    Aaron Edward olson

    Co-Chief Executive Officer (Co-CEO) Product Vision, Platform Strategy, and Narrative Leadership

    Aaron Olson is the founder of MyReentry and serves as Co-CEO, leading product vision, platform strategy, and long-term innovation. An award-winning journalist, reentry strategist, and creator of The Abolition Christian Podcast, Aaron brings over 20 years of lived experience inside the prison system, giving him an unparalleled understanding of the structural failures in reentry. From within the carceral system, Aaron operates as the primary architect of MyReentry's system design, shaping:
    • Platform architecture and workflow
    • User experience and human-centered design
    • Core product strategy and feature prioritization
    • The philosophical foundation behind MyReentry's readiness and opportunity-based model
    He serves as the bridge between lived experience and technical execution, ensuring that every aspect of the platform reflects the real needs, behaviors, and challenges of people transitioning home. Aaron's leadership positions MyReentry as both product and movement redefining how reentry is understood and built.

    tracy michelle olson

    Chief Operating Officer (COO) Operations, Strategy Execution, and Organizational Infrastructure

    Tracy Olson serves as Chief Operating Officer, overseeing day-to-day operations, execution strategy, and organizational infrastructure. With over 15 years of experience in social services and a background in business and entrepreneurship, Tracy brings strong expertise in:
    • Administrative leadership
    • Systems coordination
    • Case management and behavioral support environments
    • Organizational development and compliance
    A formerly incarcerated professional, Tracy plays a central role in:
    • Business planning and investor readiness
    • Internal operations and workflow systems
    • Strategic coordination across the founding team
    • Partner communications and relationship management
    She is the operational backbone of MyReentry--ensuring that vision turns into structured, scalable execution.

    Christopher Blackwell

    Chief Communications Officer (CCO) Media Visibility, National Narrative Strategy, and Investor Outreach

    Christopher Blackwell serves as Chief Communications Officer, leading media, national narrative strategy, and investor outreach. He is the co-founder and Executive Director of Look2Justice, a grassroots organization that provides peer-led civic education and empowerment programs to impacted persons and their families to navigate legislative, policy, and narrative change. His writing has been featured in:
    • The New York Times
    • The Washington Post
    • and other top publications
    Currently incarcerated in Washington State, Chris brings a powerful and credible voice to:
    • Public narrative around incarceration and reentry
    • Media engagement and national storytelling
    • Investor and public-facing messaging
    He leads:
    • Brand narrative development
    • Media outreach and strategic communications
    • Public trust and awareness building
    Chris ensures MyReentry is not only built--but seen, understood, and supported at scale.

    Devon Adams

    Co-Chief Executive Officer (Co-CEO) External Leadership, Partnerships, and Institutional Strategy

    Devon Adams serves as Co-CEO of MyReentry, leading external strategy, partnerships, and institutional engagement. As Co-Executive Director of Civil Survival, Devon brings deep experience in: Reentry systems and policy Government and Department of Corrections relationships Community-based program development Equity-driven leadership A formerly incarcerated leader, Devon plays a critical role in positioning MyReentry for real-world adoption, ensuring the platform aligns with:
    • Community needs
    • Institutional requirements
    • Scalable partnership opportunities
    He leads:
    • Strategic partnerships (nonprofits, workforce, housing, DOC)
    • Pilot program development
    • Stakeholder engagement and credibility building
    • External representation with funders and agencies
    Devon's leadership ensures MyReentry is not only visionary--but deployable, trusted, and scalable.

    Massimo Bardetti

    Chief Technology Officer (CTO) Platform Architecture, Engineering, and AI Systems

    Massimo Bardetti serves as Chief Technology Officer, leading the design and development of the MyReentry platform architecture. Based in Silicon Valley, Massimo has engineering experience with:
    • Microsoft
    • Amazon
    • Multiple AI-focused startups
    He is responsible for building a secure, scalable, and intelligent system that supports:
    • Real-time personalization
    • Cross-platform integration
    • AI coaching and adaptive workflows
    • Long-term infrastructure for national scale
    Massimo also leads the development and protection of MyReentry's proprietary algorithmic systems, including:
    • Smart matching
    • Readiness modeling
    • Adaptive reentry planning
    His leadership ensures MyReentry is not just functional--but technically differentiated and enterprise-ready.

    Aaron Edward olson

    Co-Chief Executive Officer (Co-CEO) Product Vision, Platform Strategy, and Narrative Leadership

    Aaron Olson is the founder of MyReentry and serves as Co-CEO, leading product vision, platform strategy, and long-term innovation. An award-winning journalist, reentry strategist, and creator of The Abolition Christian Podcast, Aaron brings over 20 years of lived experience inside the prison system, giving him an unparalleled understanding of the structural failures in reentry. From within the carceral system, Aaron operates as the primary architect of MyReentry's system design, shaping:
    • Platform architecture and workflow
    • User experience and human-centered design
    • Core product strategy and feature prioritization
    • The philosophical foundation behind MyReentry's readiness and opportunity-based model
    He serves as the bridge between lived experience and technical execution, ensuring that every aspect of the platform reflects the real needs, behaviors, and challenges of people transitioning home. Aaron's leadership positions MyReentry as both product and movement redefining how reentry is understood and built.

    tracy michelle olson

    Chief Operating Officer (COO) Operations, Strategy Execution, and Organizational Infrastructure

    Tracy Olson serves as Chief Operating Officer, overseeing day-to-day operations, execution strategy, and organizational infrastructure. With over 15 years of experience in social services and a background in business and entrepreneurship, Tracy brings strong expertise in:
    • Administrative leadership
    • Systems coordination
    • Case management and behavioral support environments
    • Organizational development and compliance
    A formerly incarcerated professional, Tracy plays a central role in:
    • Business planning and investor readiness
    • Internal operations and workflow systems
    • Strategic coordination across the founding team
    • Partner communications and relationship management
    She is the operational backbone of MyReentry--ensuring that vision turns into structured, scalable execution.

    Christopher Blackwell

    Chief Communications Officer (CCO) Media Visibility, National Narrative Strategy, and Investor Outreach

    Christopher Blackwell serves as Chief Communications Officer, leading media, national narrative strategy, and investor outreach. He is the co-founder and Executive Director of Look2Justice, a grassroots organization that provides peer-led civic education and empowerment programs to impacted persons and their families to navigate legislative, policy, and narrative change. His writing has been featured in:
    • The New York Times
    • The Washington Post
    • and other top publications
    Currently incarcerated in Washington State, Chris brings a powerful and credible voice to:
    • Public narrative around incarceration and reentry
    • Media engagement and national storytelling
    • Investor and public-facing messaging
    He leads:
    • Brand narrative development
    • Media outreach and strategic communications
    • Public trust and awareness building
    Chris ensures MyReentry is not only built--but seen, understood, and supported at scale.

    Devon Adams

    Co-Chief Executive Officer (Co-CEO) External Leadership, Partnerships, and Institutional Strategy

    Devon Adams serves as Co-CEO of MyReentry, leading external strategy, partnerships, and institutional engagement. As Co-Executive Director of Civil Survival, Devon brings deep experience in: Reentry systems and policy Government and Department of Corrections relationships Community-based program development Equity-driven leadership A formerly incarcerated leader, Devon plays a critical role in positioning MyReentry for real-world adoption, ensuring the platform aligns with:
    • Community needs
    • Institutional requirements
    • Scalable partnership opportunities
    He leads:
    • Strategic partnerships (nonprofits, workforce, housing, DOC)
    • Pilot program development
    • Stakeholder engagement and credibility building
    • External representation with funders and agencies
    Devon's leadership ensures MyReentry is not only visionary--but deployable, trusted, and scalable.

    Massimo Bardetti

    Chief Technology Officer (CTO) Platform Architecture, Engineering, and AI Systems

    Massimo Bardetti serves as Chief Technology Officer, leading the design and development of the MyReentry platform architecture. Based in Silicon Valley, Massimo has engineering experience with:
    • Microsoft
    • Amazon
    • Multiple AI-focused startups
    He is responsible for building a secure, scalable, and intelligent system that supports:
    • Real-time personalization
    • Cross-platform integration
    • AI coaching and adaptive workflows
    • Long-term infrastructure for national scale
    Massimo also leads the development and protection of MyReentry's proprietary algorithmic systems, including:
    • Smart matching
    • Readiness modeling
    • Adaptive reentry planning
    His leadership ensures MyReentry is not just functional--but technically differentiated and enterprise-ready.

    Advisory Board

    Herman Jungbauer

    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur.

    Beth Saidel

    Beth Saidel is a writer and editor living in New York City. For over seventeen years, she served as the senior writer for executive communications at Barnard College, Columbia University, drafting major speeches and strategic communications. Currently, she works as a freelance writer for academic institutions and non-profit organizations. She also coaches high school students on college essays, job seekers on letters and resumes, and anyone in search of the perfect prose. A former professional dancer, Beth graduated from Harvard College where she studied visual arts. Her passion for performance, color, rhythm, and style is evident in her written work. Since 2022, she has spent time mentoring incarcerated aspiring writers and journalists through the Writers Development Program. It was then that she had the great fortune to meet and work with Aaron Olson, who is leading MyReentry. Beth is honored to serve on the advisory board for this vitally important effort.

    Deborah Zalesne

    Deborah Zalesne is a tenured professor of law at the City University of New York School of Law. She has published extensively in the areas of criminal justice, race and gender justice, legal pedagogy, and issues relating to the use of contracts to empower disenfranchised communities. She has authored or co-authored three books and more than fifty scholarly articles, including Ending Isolation: The Case Against Solitary Confinement, co-authored with incarcerated journalist Christopher Blackwell (Pluto Press 2025). She is currently co-writing a book called “Finding Oneself in Solitude,” that provides mindfulness training and practices for people in solitary confinement, and co-editing a book entitled “Dear Teenage Me: Voices from Beyond the Barbed Wire,” that includes essays by incarcerated people in the form of letters to their younger selves. Deborah co-founded and runs a Writers Development Program that pairs aspiring incarcerated writers with inside and outside volunteer mentors who support their writing and help pitch it to media outlets.

    Herman Jungbauer

    Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur.

    Beth Saidel

    Beth Saidel is a writer and editor living in New York City. For over seventeen years, she served as the senior writer for executive communications at Barnard College, Columbia University, drafting major speeches and strategic communications. Currently, she works as a freelance writer for academic institutions and non-profit organizations. She also coaches high school students on college essays, job seekers on letters and resumes, and anyone in search of the perfect prose. A former professional dancer, Beth graduated from Harvard College where she studied visual arts. Her passion for performance, color, rhythm, and style is evident in her written work. Since 2022, she has spent time mentoring incarcerated aspiring writers and journalists through the Writers Development Program. It was then that she had the great fortune to meet and work with Aaron Olson, who is leading MyReentry. Beth is honored to serve on the advisory board for this vitally important effort.

    Deborah Zalesne

    Deborah Zalesne is a tenured professor of law at the City University of New York School of Law. She has published extensively in the areas of criminal justice, race and gender justice, legal pedagogy, and issues relating to the use of contracts to empower disenfranchised communities. She has authored or co-authored three books and more than fifty scholarly articles, including Ending Isolation: The Case Against Solitary Confinement, co-authored with incarcerated journalist Christopher Blackwell (Pluto Press 2025). She is currently co-writing a book called “Finding Oneself in Solitude,” that provides mindfulness training and practices for people in solitary confinement, and co-editing a book entitled “Dear Teenage Me: Voices from Beyond the Barbed Wire,” that includes essays by incarcerated people in the form of letters to their younger selves. Deborah co-founded and runs a Writers Development Program that pairs aspiring incarcerated writers with inside and outside volunteer mentors who support their writing and help pitch it to media outlets.

    Disclaimer: This site is for informal and educational purpose only. All content © MyReentry LLC 2026

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