We caught up with the brilliant and insightful Matt Fogarty a few weeks ago and have shared our conversation below.
Matt, looking forward to hearing all of your stories today. Let’s kick things off with talking about how you serve the underserved, because in our view this is one of the most important things the small business community does for society – by serving those who the giant corporations ignore, small business helps create a more inclusive and just world for all of us.
My business comprises both for-profit and nonprofit entities dedicated to supporting individuals experiencing homelessness. I founded Cherry Willow Apparel, our nonprofit arm, to symbolize unconditional love. Wearing Cherry Willow signifies hope and advocacy, fostering a community passionate about supporting the homeless.
A common misconception is that homelessness results from unemployment. However, studies reveal that approximately 53% of sheltered and 40% of unsheltered homeless individuals are employed. Reference ENDHOMELESSNESS.ORG for the study. This underscores that homelessness is often due to systemic issues like wage exploitation and a lack of affordable housing.
For instance, major corporations like Walmart and McDonald’s employ numerous staff who rely on food stamps, indicating that wages are insufficient to cover basic living expenses. This taxpayer-subsidized corporate profit highlights the need for policy change. Through Cherry Willow, we aim to educate the public on such systemic issues, advocating for solutions that address the root causes of homelessness.
Matt, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I have been involved in service work since I was young, instilled with the belief that giving back is essential. My parents led by example, volunteering for church functions and supporting migrant workers in our community. Though I didn’t fully grasp the sacrifices these workers made at the time, their dedication to providing for their families left a lasting impression on me.
When I founded Cherry Willow Apparel, I wasn’t entirely sure how I would contribute to ending homelessness, but I knew I could serve those affected. With my experience in business, I was confident in creating value through apparel, having done so successfully before. More importantly, I was deeply committed to the mission, which drives me to give it my all. I used a Japanese Philosophy called Ikigai to come up with the idea. Ikigai is a symbol and is the intersection of “what you are good at,” “what you love to do,” “what the world needs,” and “what you can get paid for.” It is a worthy pursuit and a way to find alignment in our capitalist society.
My journey into entrepreneurship began with a strong work ethic and financial discipline. My first jobs as a teenager—working concessions at a drive-in theater and detasseling corn—taught me the value of hard work and saving money. This discipline led me to study Finance and Sports Management at Loyola University Chicago, though my career ultimately took a different path.
A pivotal moment in my life came during my first year of college, when I was assigned 50 hours of community service after getting in trouble for drinking. This experience introduced me to volunteering with people experiencing homelessness in Chicago. Seeing the circumstances that people living on the streets of Chicago faced, I was always impressed by how they found things to be grateful for!
After college, I initially planned to work in sports, but life had other plans. When my girlfriend at the time became pregnant just before my graduation, I quickly pivoted my focus to financial stability. I took a commission-only sales job in the auto industry, where my ability to succeed directly impacted my ability to provide for my family. This experience mirrored entrepreneurship in many ways—I had to bet on myself, and failure wasn’t an option. I thrived in this environment, winning multiple awards for my performance, but after years without growth opportunities, I sought something more fulfilling.
My entrepreneurial instincts developed even further when I joined a French startup supporting small business owners. I discovered that I approached work with an entrepreneurial mindset and felt a deep connection to the small business community. I also gained exposure to the apparel industry through a local business I was prospecting. What started as a side commission-based role turned into a realization—I wanted to build something of my own.
Cherry Willow Apparel was born from this desire and my long-standing commitment to service. I wanted to create a community of advocates using apparel to be a visible sign of hope in communities across the country for people experiencing homelessness. The name comes from the streets I grew up on in Dayton, Ohio, and symbolizes the beauty in all stages of life. Just as nature is beautiful beyond its moments of full bloom, so too are people—especially those experiencing homelessness, who are often overlooked and misunderstood.
At Cherry Willow, we aim to empower people experiencing homelessness by sharing their stories and challenging misconceptions. Homelessness is not just an individual issue—it’s a systemic problem, often tied to wage exploitation and lack of affordable housing. Too frequently, the focus is placed on struggling individuals rather than corporations paying unlivable wages and forcing employees to rely on government assistance. We focus on blaming people who can’t afford housing rather than blaming real estate development companies who have prioritized increased profits from a fundamental human right to housing. We aim to shift this narrative through education and advocacy and push for meaningful change.
I am most proud of what Cherry Willow stands for: unconditional love. Please follow us on social media to keep up with our work. If you are interested in reading more about me and my journey, I am working on publishing a book titled “Ego Death & Enlightenment,” where I go into more depth on the experiences, learnings, and philosophies that led me to found Cherry Willow Apparel.
We’d love to hear a story of resilience from your journey.
Before I decided to found Cherry WIllow Apparel, I took a job on the Go-To-Market team for a French-based Business Intelligence start-up. I was one of their first ten employees in the US. I was excited about the opportunity to bring this product into the US market despite having no experience selling business intelligence products or having in-depth knowledge of the industry. Things were going well. I was starting to generate opportunities consistently and was being asked to mentor other reps on the team and show them what I was doing to be successful. Then, one morning, about 6 months after I had taken the job, I got a call from my VP of Sales. He told me there was a disagreement between the CEO, whom I worked under, & the CTO (founder), & the board of directors. The founder had the board’s backing and decided to pull out of the US market. That meant that my co-workers and I were all laid off. We received 3 weeks’ pay and were sent on our way. It’s never a good time to be laid off, but it was terrible for me. At the time, I was going through a divorce and had lawyer bills I needed to pay. Despite that, during those weeks I was laid off, I was the most free I had ever felt. That is when I decided I wanted to work for myself and become an entrepreneur. I started Cherry Willow in January 2024 and have worked on it ever since!
How’d you meet your business partner?
When I got laid off, I reached out to a connection I had made on LinkedIn. We connected over working for early-stage start-ups, I told him the experience of getting laid off had cemented my decision to be an entrepreneur, and I shared my idea with him about Cherry WIllow Apparel. He immediately put me in touch with my now co-founder, David Gray. David and I have worked together every week since that initial introduction on LinkedIn. We have become good friends, and I can’t thank him enough for his support and guidance throughout the entrepreneurial process. David is a multiple time start-up founder and now uses his experience to help other entrepreneurs build their start-ups and get their businesses off the ground.
Contact Info:
- Website: https://www.cherrywillowapparel.com/
- Instagram: https://www.instagram.com/fog2foge/
- Facebook: https://www.facebook.com/CherryWillowApparel
- Linkedin: https://www.linkedin.com/in/foge/
- Twitter: https://x.com/CherryWillowApp
- Youtube: https://www.youtube.com/@CherryWillow_Apparel
Image Credits
Personal Photos taken from my phone