Meet Wesley Holloway

We were lucky to catch up with Wesley Holloway recently and have shared our conversation below.

Hi Wesley, appreciate you sitting with us today. Maybe we can start with a topic that we care deeply about because it’s something we’ve found really sets folks apart and can make all the difference in whether someone reaches their goals. Self discipline seems to have an outsized impact on how someone’s life plays out and so we’d love to hear about how you developed yours?

I think my self-discipline was forged long before I ever stepped into the business world. Growing up in Oklahoma City, the youngest of three boys meant I learned early that if I wanted to be heard, I had to be persistent, and if I wanted to win… I had to work for it.

Sports played a huge role in shaping that drive. My high school wasn’t just about showing up to practice — it was about pushing to become the absolute best version of yourself, on and off the field. In hindsight, this was a huge blessing to me! Having those values instilled in me at such a young age has proven to be invaluble. That mindset carried me through playing football at the next level and later into earning my master’s degree. It taught me that discipline isn’t a momentary push — it’s showing up consistently, even when it’s hard, and especially when no one’s watching.

A lot of credit also goes to my parents. They led by example — working hard as entrepreneurs, treating people right and with respect, and reminding me that how you win is just as important as the win itself. Those lessons stuck.

So for me, self-discipline is less about willpower in the moment and more about a lifetime of community, habits, challenges, and a refusal to cut corners — whether that’s on the football field, in the classroom, or running Benevolent Bakery today.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

Benevolent Bakery started the way a lot of great ideas do — with A LOT of R&D, and finally an “AHA” moment. The breakthrough idea of all ideas! Back in the day, baking “special” brownies was more mystery than science… you never really knew what was in them or how strong they’d be. I wanted to keep the fun and nostalgia of that experience, but strip away the guesswork. That’s how our infused baking mixes were born — consistent, delicious, and easy enough for anyone to make.

What makes this work exciting for me is that it’s not just about a product — it’s about an experience. We’re creating moments people remember, whether that’s friends laughing in the kitchen, couples baking on a quiet night in, or someone discovering edibles in a safe, approachable way for the first time. Every box we sell also supports local nonprofits, so our growth literally means more impact in the communities we serve.

Right now, we’re in an exciting growth phase — expanding into new states and building partnerships with retailers who share our vision. In the next 60–90 days, we’ll be launching in Illinois, and we’ve got a few new treats coming out of the oven: our “Wake ‘n Bake” pancake mix drops in October, and our seasonal hot cocoa will roll out nationwide this Labor Day.

For me, the heart of Benevolent Bakery is simple: do good work, do right by people, and make something worth sharing. The rest — the growth, the launches, the milestones — that’s just the icing on the cake… or, in my case, the frosting on the confetti cake mix.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

1. Humility.
To be successful, you have to fail — it’s not optional. And when you do, being humble in that failure is what allows you to truly learn from it and grow. I’ve made big mistakes in business, and every single one taught me something that shaped who I am as a leader. My advice? Drop the ego. Own your mistakes, ask for feedback, remain open to feedback/criticism and treat every setback as a masterclass you didn’t have to pay tuition for.

2. Relationship-Building.
At the end of the day, business is people. The deals I’ve done, the partnerships I’ve built, and the doors that have opened for Benevolent Bakery almost always trace back to a relationship — often one built long before the opportunity came along. My advice? Treat people right whether there’s something in it for you or not. When you lead with respect and generosity, you create a network that actually wants to see you win.

3. Adaptability.
Markets shift (A LOT), laws change, supply chains break… and sometimes your “perfect” plan needs to be thrown out the window at the last minute. Being able to adapt without losing your vision or confidence is a skill that will keep your business alive when others get stuck. My advice? Stay curious, stay humble, and don’t fall so in love with your original plan that you miss the better opportunity in front of you.

If I had to sum it up, it’s this: be tough enough to keep going, kind enough to bring people with you, and flexible enough to change course without losing momentum. Do those three things well, and you’ll have a fighting chance in any industry. If I could add a 4th, it would be resilience but we covered that earlier!

Awesome, really appreciate you opening up with us today and before we close maybe you can share a book recommendation with us. Has there been a book that’s been impactful in your growth and development?

One of the most impactful books I’ve read is Principles: Life and Work by Ray Dalio. It completely reframed how I think about collaborating, leading, problem-solving, and navigating the day-to-day challenges that come with both business and life.

What stuck with me most was Dalio’s idea of creating a culture of radical transparency — where honest feedback isn’t just tolerated, it’s encouraged. It reminded me that great ideas can come from anywhere, and that ego has no place in decision-making.

The book also reinforced the value of approaching problems like puzzles, not roadblocks. Instead of reacting emotionally, you step back, see all the pieces, and figure out how they fit together. That shift alone has helped me lead more effectively and make better decisions under pressure.

In short, Principles taught me that success isn’t about having all the answers — it’s about building the systems, relationships, and mindset to find the answers together. I would suggest this book to anyone, especially business owners or soon to be business owners.

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