Today we’d like to introduce you to Gary Wilkerson.
Hi Gary, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I spent more than 20 years chasing my entrepreneurial spirit. I knew how to work hard, I knew how to build, and I tasted both success and failure along the way. But nothing prepared me for what happened when my last business collapsed just before the mortgage crisis of 2008. My wife and I lost almost everything—our home, our cars, our belongings. It was the hardest season of our lives. We would have ended up homeless ourselves if it had not been for our church and our family stepping in.
Work was nearly impossible to find. Customers were suing me, filing charges for work we could no longer complete, and I suddenly found myself fighting not just for stability, but for my freedom. In the middle of that chaos, I began doing community service and volunteering. What started as something I had to do became something I wanted to do. It opened doors to employment, but more importantly, it opened my eyes. I realized that serving others was not just meaningful—it was my calling.
I fell in love with the nonprofit world and the incredible work happening in our community. In 2010, I was hired to mentor men exiting the criminal justice system, which led to another opportunity working with people experiencing homelessness at MHMR of Tarrant County, and then became a mentor for Fathers with an organization called New Day Services for Children and Families. During that same period, two of our teenage daughters began their own painful journey through addiction and homelessness. Walking through that with them, combined with our own near‑homelessness, changed me forever.
Those experiences are what led me to start When We Love in 2012. I wanted to build an organization that didn’t just offer temporary relief, but one that walked with individuals and families through the hard work of rebuilding their lives. I worked a full‑time job for ten years while building When We Love so that I would never be a financial burden on the mission.
Today, we are entering our 14th year of serving, leading, and growing in our community. Everything we do is rooted in one vision: to teach individuals and families how to Beat Homelessness. My journey has been anything but easy, but every step—every loss, every lesson, every moment of grace—has led me to the work I was created to do.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It has definitely not been a smooth road. In fact, this has been one of the hardest things I have ever done, but also the most rewarding. I still remember telling my wife after my last business failure, “I will never own another business again.” Yet here I am, seventeen years later, running a nonprofit organization.
The early years were especially difficult. I had very little—virtually nothing—to fund the organization with, and at the same time I was trying to rebuild my reputation. That takes time. It takes consistency. It takes showing up day after day and proving to the community that I was capable of doing this work with integrity, transparency, and good stewardship of every dollar entrusted to us.
One of the biggest lessons I have learned is that nonprofit work is far more challenging than anything I ever experienced in the for‑profit world. In business, you have products or services that generate income. In nonprofit work, you rely solely on the goodwill and generosity of people who believe in your mission. You have to continually seek out individuals whose hearts move them to open their wallets—not for something they will receive, but for someone else’s chance at a better life.
That is not an easy task. But it is meaningful. It is sacred. And every struggle along the way has shaped me into the leader I needed to become for this work. The road has been hard, but the impact has made every step worth it.
Alright, so let’s switch gears a bit and talk business. What should we know?
When We Love is a nonprofit organization dedicated to serving individuals and families experiencing and recovering from homelessness. At our core, we believe that homelessness is not just a housing issue—it is a human issue. And the most powerful tool we have to address it is love expressed through consistent, practical, dignifying action.
What we do is simple in concept but profound in impact. We walk alongside people who are in crisis or transition and help them stabilize, rebuild, and ultimately learn how to Beat Homelessness. Our work includes meeting immediate needs like food, clothing, transportation, and emergency support, but it goes far deeper than that. We focus on long‑term solutions: teaching life skills, helping people reconnect with family, supporting employment efforts, and guiding individuals through the difficult steps of rebuilding their lives.
What sets us apart is our relational approach. We do not operate as a transactional service provider. We operate as a community. We know people by name. We listen to their stories. We walk with them through setbacks and celebrate their victories. Many of our team members, including myself, have lived experience with homelessness or have walked through it with family members. That gives us a level of empathy, understanding, and authenticity that cannot be manufactured.
Brand‑wise, I am most proud that When We Love has become known for dignity. People trust us because we treat every person with respect, compassion, and honesty. We do not shame people for their circumstances. We do not give up on them when things get hard. Our brand is built on the belief that every person deserves to be seen, valued, and supported as they work toward stability.
What I want readers to know is this: When We Love is not just a name. It is a way of operating. It is a commitment to show up, to care deeply, and to help people move from crisis to confidence. We specialize in the kind of work that takes time, patience, and heart. And after nearly fourteen years, we have seen lives transformed, families reunited, and futures restored.
We are here to teach individuals and families how to Beat Homelessness—not just for a night, but for a lifetime.
We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
Luck has certainly shown up in my story, but not always in the way people expect. If you look at the surface, you might say I had a long stretch of bad luck. My last business collapsed right before the mortgage crisis. My wife and I lost almost everything. Work was scarce, lawsuits were piling up, and I found myself fighting battles I never imagined I would face. Then, as I stepped into nonprofit work, two of our daughters entered their own painful journey through addiction and homelessness. None of that felt like luck at the time.
But looking back, I can see that what felt like bad luck was actually shaping me. It was refining me, humbling me, and preparing me for the work I do today. Those experiences gave me a level of empathy and understanding that no classroom or training ever could. They allowed me to sit with people in their darkest moments and truly understand what they are facing.
And then there has been what some might call good luck—doors opening at just the right time, people stepping in when we needed help, opportunities appearing when I had nothing left to offer. But I see those moments less as luck and more as grace. The right people showed up. The right mentors believed in me. The right opportunities came when I was ready to say yes.
So yes, luck has played a role in my life and in When We Love. But the truth is, both the good and the bad have worked together to shape the mission we carry today. The hard seasons gave me purpose. The unexpected blessings gave me strength. And together, they led me to build an organization that exists to help others find their way through the very struggles I once faced myself.
Contact Info:
- Website: https://www.whenwelove.com/
- Instagram: https://www.instagram.com/whenwelove1/
- Facebook: https://www.facebook.com/whenwelove.org
- Youtube: https://www.youtube.com/@WhenWeLove
