We recently connected with Chris Wysong and have shared our conversation below.
Chris, so great to be with you and I think a lot of folks are going to benefit from hearing your story and lessons and wisdom. Imposter Syndrome is something that we know how words to describe, but it’s something that has held people back forever and so we’re really interested to hear about your story and how you overcame imposter syndrome.
Entrepreneurship is a daily balancing act between confidence and doubt. Some mornings I wake up feeling unstoppable. Other days, I sit in a room full of other founders and wonder if I somehow walked into the wrong place. That little voice in my head, the doubt monster, can be relentless. Over time, I’ve learned it’s not about silencing it. It’s about keeping moving forward.
For me, it all started at local farmer markets. Sharing Bucket of Bread repeatedly didn’t just help me memorize a pitch; it let me hear my own words, refine my message, and build real confidence. Every interaction, every question from a customer, helped push away that little voice that whispered, “Do you really belong here?”
Opportunities began to grow. Invitations to culinary-focused radio shows, state-sponsored small business resource events where I represented my city and introduced our Mayor, panels at universities and Veteran-centric organizations, and multiple other stages for live-audience pitch contests all reinforced that what I was building mattered. Each opportunity was a chance to practice, refine, and validate my ideas. These moments weren’t about ego. They were proof that my work resonated and that my voice deserved to be heard.
I remember Wisconsin’s “Project Pitch It,” a televised Shark Tank-style competition. I walked in feeling like the underdog, but by the end, I had earned the top prize for concept, presentation, and delivery. That moment taught me that belief in your story can carry you through even the loudest doubts.
Along the way, Chef Angie Ragan, a semi-finalist from Gordon Ramsay’s Next Level Chef, invited me to Lubbock, Texas, to teach baking classes at her event. Appearing together on a live morning talk show and being introduced as a celebrity chef was both surreal and affirming.
The latest and biggest business adventure came at the Verizon Small Business Training Camp in San Francisco, a three-day immersive event at Verizon’s Innovation Lab. Surrounded by founders who seemed miles ahead and learning directly from experts like Drew Brees and Kristin Juszczyk, doubt tried to creep in again. But by then, I had enough evidence of my own capabilities, including sales, invitations, and audience engagement, to know I belonged.
Imposter syndrome never fully disappears, but I’ve learned to let it sharpen me instead of paralyze me. Every time I question myself, I check the proof: the work I’ve done, the people I’ve impacted, and the opportunities I’ve earned. Showing up, doing the work, and bringing what only I can bring has become my daily practice.
It’s a process that works itself out over time. Confidence doesn’t appear overnight. It comes from starting, from constant improvement and adaptation, from paying attention to your delivery, and from simply committing to doing the work. Time and experience build that confidence naturally. But if someone is feeling stuck before even starting, the best thing they can do is jump in. There’s no shortcut—action is the only way forward.
That is how I live with imposter syndrome, not as a limitation, but as a constant reminder to keep climbing, keep proving, and keep growing.
Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?
At Bucket of Bread, I create versatile organic baking kits that make homemade bread and baked goods simple, fun, and approachable. Each kit is filled with certified organic, non-GMO ingredients and contains no added sugars, preservatives, or artificial junk. What makes it exciting is how flexible it is—one kit can turn into loaves of bread, pizza crusts, pretzels, bagels, cinnamon rolls, and so much more. It sparks creativity in the kitchen, whether you’re a seasoned baker or just starting out.
What’s really special, though, is that every kit also does good beyond the kitchen. A portion of our profits helps combat food insecurity, and customers can even choose to send kits directly to food banks across the U.S. I started this company with the idea that baking could not only bring people together, but also make a real impact in our communities.
Right now, we’re excited about new merchandise and seasonal recipe releases, plus expanding into more partnerships where Bucket of Bread can show up at fundraisers, events, and in collaborative spaces. The latest “big adventure” was attending Verizon’s Small Business Training Camp in San Francisco, where I gained new tools to grow Bucket of Bread into a household name. Looking ahead, I’m continuing to build ways for more families to discover the joy of baking while making sure every purchase contributes to something bigger.
If you had to pick three qualities that are most important to develop, which three would you say matter most?
Looking back, there are three qualities that have made the biggest impact on my journey. The first is resilience. Running a small business is full of ups and downs, and learning to push through doubt, setbacks, or even just everyday challenges is critical. Resilience doesn’t mean you never feel fear or uncertainty. It means you keep moving forward anyway, learning from mistakes and adjusting along the way.
The second is adaptability. Things rarely go exactly as planned. Whether it’s a new sales channel, a product tweak, or responding to customer needs, being willing to pivot and experiment has kept Bucket of Bread growing. I’ve learned to pay attention to data, listen to feedback, and try new approaches without getting stuck on a perfect plan.
The third is confidence in your voice and vision. Confidence doesn’t mean ego or thinking you’re always the smartest person in the room. It’s knowing that your perspective and your work have value, even when doubt creeps in. That confidence grows with experience, repetition, and proof points, whether it’s positive customer feedback, winning a pitch contest, or seeing an idea actually work in practice.
For folks just starting out, my advice is simple: start doing, keep learning, and keep showing up. Build resilience by facing small challenges and learning from them. Develop adaptability by trying new approaches and being willing to pivot. And cultivate confidence by putting your work out into the world, listening to results, and using that feedback as proof that you belong at the table. None of these qualities appear overnight, but if you commit to the process, they compound over time and become your greatest assets.
How can folks who want to work with you connect?
Beyond a future customer, I’m always looking to connect with like-minded partners and collaborators who share a passion for creativity, community impact, and making quality baking accessible to more people. That could be fellow entrepreneurs, culinary professionals, food-focused brands, Veteran or community organizations, micro-influencers, or anyone interested in creating experiences that bring people together through baking. Micro-influencers who are interested in creating a win-win scenario that benefits both their audience and Bucket of Bread are welcome to reach out as well.
The real effort for me is growing Bucket of Bread, because the bigger the company becomes, the greater the impact our profit-sharing charitable mission can have. One key focus is scaling into retail and grocery channels, and I’m very open to connecting with experts in these arenas who want to provide mentorship, guidance, or strategic collaboration to help us get there. Collaborations can also take many forms, including co-hosting events, creating unique product offerings, or developing programs that give back to the community. I’m particularly interested in partnerships that align with our mission of supporting food security while sparking joy in the kitchen.
If this resonates with you, I’d love to hear from you. The best way to connect is through our website at BucketofBread.com, where there’s a contact form, or by calling the Bucket of Bread hotline at 1-844-627-3237. I welcome conversations, ideas, and collaborations that help both sides grow and make a positive impact.
Contact Info:
- Website: https://bucketofbread.com
- Instagram: https://www.instagram.com/bucketofbreadllc/
- Facebook: https://www.facebook.com/BucketofBread
- Linkedin: https://www.linkedin.com/company/bucketofbread
so if you or someone you know deserves recognition please let us know here.
