Today we’d like to introduce you to Sterling Sherwood.
Hi Sterling, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
In January of 2025, my father passed away. Losing a parent, especially the first one, changes something in you. It really made me step back and reflect on my life and what I was doing with it.
I had been a stay-at-home dad for about 14 years, which I’m proud of, but I also started to feel like I hadn’t built something of my own or made the kind of impact I wanted to make in the world.
My dad left us a small inheritance. Nothing life-changing, but enough where I had a choice. I could either let it sit, or try to build something meaningful with it.
For about five or six months, I was honestly just navigating grief and thinking. I explored different ideas like starting a food truck or setting up vending machines around town. I knew I wanted to do something better for my family, but also something that could help others.
Then one night, something simple clicked.
We had an unexpected expense come up and needed about $500. I remember thinking, “If 500 people each gave just $1, we’d be completely fine.”
That thought stuck with me.
It made me realize how powerful small contributions could be when people come together. That idea became the foundation for HopeWin.
HopeWin was built on a simple belief: that even the smallest act of giving can create real impact when it’s shared across a community. What started as a moment of stress and reflection turned into something much bigger, a mission to help families while showing that every dollar truly does build something meaningful.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It definitely hasn’t been a smooth road.
In the early stages, before HopeWin ever launched publicly, there was a lot of trial and error. The idea you see today went through several versions before we landed on something that was both meaningful and legally sound.
Believe it or not, the very first concept actually started closer to a sweepstakes-style model. As we dug deeper, we quickly realized there were serious legal and compliance concerns with that approach. That forced us to step back and completely rethink the structure.
From there, it became a process of constant iteration. We consulted with legal professionals, worked through the requirements for 501(c)(3) status, and rebuilt the model from the ground up to make sure everything aligned with nonprofit regulations and long-term sustainability.
At the same time, I was learning everything as I went. My background wasn’t in business or nonprofits. My last job before this was delivering pizzas. So stepping into something like this meant figuring out systems, finances, compliance, and operations from scratch.
There were definitely moments where it felt overwhelming, but I stayed focused on the bigger picture. I just kept setting small goals, solving one problem at a time, and moving forward.
Looking back, those challenges were necessary. They shaped HopeWin into what it is today and made the foundation much stronger than it would have been if everything had come easy.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
My background isn’t what you’d typically expect for someone starting a nonprofit. Before HopeWin, I worked jobs like delivering pizzas and doing seasonal work for a pool company. I didn’t come from a business or nonprofit background, so stepping into this world was completely new for me.
In a lot of ways, I’ve had to learn everything from the ground up. Building systems, understanding compliance, and figuring out how to run an organization were all things I had to teach myself as I went.
That said, what I’m most proud of isn’t a job title. It’s being a stay-at-home dad for the past 14 years and being present for my family. That time shaped who I am and ultimately influenced why I built HopeWin in the first place.
None of it would have been possible without my other half. She’s been the one holding everything together behind the scenes, supporting our family and giving me the space to grow into something like this. HopeWin may have started with an idea I had, but it’s absolutely built on the foundation we created together.
What sets me apart is that I didn’t come into this with a traditional path or expectations. I’m building this from real life experience, from understanding what families go through, and from a genuine desire to create something that actually helps people in a practical way.
If we knew you growing up, how would we have described you?
Growing up as a kid in the ’90s, I enjoyed a lot of the simple things most kids did. I spent a lot of time outside playing with the neighborhood kids, and when we came inside, it was video games on the N64, sleepovers, and just hanging out. I also loved watching comedies, and I’ve always been someone who enjoys making people laugh.
That part of me has stayed the same. Even now, I still play video games with my son, which has been really special.
Personality-wise, I’ve always been pretty easygoing. I’m not someone who gets worked up easily. I tend to look at situations for what they are and focus on what I can control. If something goes wrong, I try not to let it take over my mindset. I’d rather deal with it, move forward, and keep things in perspective.
I think that outlook has shaped a lot of how I approach life today.
Pricing:
- Memberships start at $1 per month – designed to make giving accessible to anyone
- Supporters can choose to give more, but all members are treated equally regardless of contribution level
- One-time donations are also available for those who prefer to give without a subscription
- 75% of funds go directly toward charitable impact, with 25% supporting operations and sustainability
- Donations are optional and never required to participate in HopeWin or apply for assistance
Contact Info:
- Website: https://www.hopewinofficial.org/
- Facebook: https://www.facebook.com/profile.php?id=61582231483085
