By Nile Livingston, Founder of Creative Repute
From May 13th to 16th, I had the pleasure of attending the 3rd annual 21 Hats Small Business Community Conference in Ann Arbor, Michigan. This marked my second time participating in this inspiring gathering of entrepreneurs from across the country. I was thrilled to reconnect with many of the familiar faces I met two years ago at the inaugural event in Chicago, including some of the community’s most insightful business leaders.
A Space for Real Conversations
The 21 Hats community, founded by journalist and entrepreneur Loren Feldman, is unlike any other. Through his podcast, newsletter, and peer network, Loren has cultivated a space where entrepreneurs openly discuss the true challenges and triumphs of building and running a business. As someone who has tuned in since early 2020, I can say with confidence that the podcast is more engaging than most reality shows—it’s raw, honest, and incredibly valuable.
I first discovered the podcast after receiving a cold email from Loren. I clicked the link out of curiosity and quickly became a loyal listener. Wanting to show appreciation, I emailed him a note of encouragement—never expecting a reply. To my surprise, Loren responded with genuine interest in Creative Repute, the design agency I founded. That interaction marked the beginning of an ongoing relationship, which later included Creative Repute designing the official cover art for the 21 Hats Podcast. Since then, I’ve continued to grow with this community and feel deeply connected to its mission.
Highlights and New Connections
This year’s conference was full of meaningful conversations and new insights. I was especially happy to see Dr. Tricia Groff, an executive psychologist and business consultant, as well as Jay Goltz, a serial entrepreneur whose company, Artists Frame Service, received a comprehensive website audit from Creative Repute with actionable recommendations to boost it’s conversion rate. I also caught up with Liz Reisch Picarazzi, founder of CITIBIN, which creates durable and modern outdoor enclosures—one of the most practical and design-forward solutions I’ve seen for city living.
I also met several inspiring entrepreneurs for the first time. One was Jaime Echt, founder of The Crafter’s Workshop, a company that creates art stencils and supplies for the craft community. Jaime is navigating the challenge of retailers placing large orders but delaying payment—a tough spot that many small business owners can relate to.
Then there was Channon Kennedy, inventor of the Morgan Square, a patented tool that simplifies the framing process in construction by combining measuring and marking. Her startup, Kiwi Vision LLC, is a true example of innovation in a niche market.
I also connected with Chris Campbell, an entrepreneur from Miami who is in the process of opening a new ice cream shop. He’s currently tackling the challenges of securing commercial real estate in a competitive market. Each of these stories reminded me of the grit and creativity it takes to build something from scratch.
A Shoutout to Zingerman’s
One of the standout experiences during the conference was the warm hospitality we received from Zingerman’s Community of Businesses. From the delicious dinner at Zingerman’s Roadhouse to a casual lunch at their iconic Deli, every meal was memorable. A special thanks goes to Brandon Gray, partner at CRI Simple Numbers, who generously gifted us merch and a meal at Miss Kim’s, a cozy boutique Korean restaurant in downtown Ann Arbor.
Equally memorable was hearing from Ari Weinzweig, Zingerman’s co-founder. His leadership approach is deeply human—despite his status, he still engages in the day-to-day, pouring water for guests and mentoring his team with humility. Ari’s story reminded me that strong leadership starts with empathy and presence. I was also impressed by Zingerman’s commitment to inclusivity, including tasty vegan options on a traditionally meat- and dairy-heavy menu.
A Visit to Motawi Tileworks
As someone with a background in fine art—I hold a BA in sculpture—visiting Motawi Tileworks was a personal highlight. Founded by Nawal Motawi, the studio produces stunning ceramic tile art inspired by Frank Lloyd Wright and Art Nouveau. What fascinated me most was their use of a physical Kanban board for project management. At Creative Repute, we use similar tools digitally, so seeing this tactile version was not only fun, it reinforced the idea that good design and organization are universal principles—digital or analog.
Discovering Ann Arbor
Ann Arbor turned out to be a charming and energetic college town. I didn’t have time to explore as much as I’d hoped, but I did start my day at Juicy Kitchen, a local juice bar that offered great dairy-free breakfast options. A few shops away, I picked up vegan desserts at Kasoa Africa Market.
Every local I spoke to recommended the University of Michigan Museum of Art (UMMA). Although I didn’t make it in person, I was able to explore their current exhibitions online. Their website features high-resolution images and detailed write-ups, allowing visitors to engage with the art virtually. I was particularly intrigued by two exhibitions: Strange You Never Knew by Jarod Lew, which explores Asian American identity through photography and multimedia, and Post No Bills, a showcase of Burhan Doğançay’s work, highlighting urban walls as ever-evolving canvases for protest, expression, and cultural commentary.
Speaking of Accessibility and Websites…
Access to information like that from UMMA’s website is exactly why great web design matters—and it’s what we specialize in at Creative Repute. Whether you’re a museum, resturant, or growing business, a well-structured digital presence allows you to tell your story, engage your audience, and convert visitors into loyal customers.
If you’re looking to build or refresh your website, Creative Repute is here to help. Mention “21 Hats” and ask to speak to me, Nile Livingston, when you reach out and we’ll include exclusive extras such as branded behind-the-scenes content, design mockups, or a social media-ready reel showcasing your brand’s transformation. Just send us an email at sales@creativerepute.com and let’s talk about how we can help you grow.
What’s New at Creative Repute?
Attending the 21 Hats Conference helped confirm that we’re on the right track. Right now, we’re finalizing a new client portal that will make it easier for clients to get started, manage their projects, and access resources. The portal will allow clients to digitally sign agreements, process payments (including recurring billing), and view onboarding materials—all in one place.
We’re also training an AI chatbot that will offer real-time support in areas like SEO, branding, and design. These tools are part of our larger mission to make design and brand strategy more accessible, intuitive, and impactful for businesses of all sizes.
We know that off-the-shelf solutions don’t always fit unique workflows. That’s why Creative Repute builds custom digital systems for businesses that need tailored tools—whether that’s for inventory management, internal communication, or customer engagement. And yes, we travel globally for on-site collaborations when needed.
Let’s Work Together
If you’re a small business owner or organization looking to elevate your digital strategy, Creative Repute is ready to partner with you. Our work is rooted in design thinking, equity, and sustainability. We believe in empowering entrepreneurs, businesses, nonprofits, and creatives through bold, effective design.
Reach out to info@creativerepute.com to learn more, ask questions, or just say hello. Our team will make sure you’re connected with the right specialist.
Thanks for reading—I’m grateful for this community and excited about what we can build together.
Warmly,
Nile Livingston, founder of Creative Repute, Inc.