From co-founding OnMilwaukee to leading marketing and civic ventures across Wisconsin, Jeff Sherman has built a career around connection and community. In this Q+A, he reflects on the mentors and risks that shaped his path, the deeper purpose behind entrepreneurship, and why curiosity, curation, and consistency still matter more than ever in a fast-changing media world.
You’ve built your career across media, marketing, entrepreneurship, and civic leadership. Looking back, what early decisions or risks most shaped your trajectory?
I listened more than I talked, asked questions and had mentors that were - thankfully - listening to me and putting up with me while pushing me through curtains, getting me seats at the right tables and truly helping me realize that life should be planned but that it plays out as a musical score. And, my parents anchored and reinforced this with encouragement and the right balance of love and accountability.
From co-founding OnMilwaukee to launching multiple start-ups, what’s the most important lesson you’ve learned about starting and sustaining a venture?
Yes, it’s about the people—but deeper, it’s about purpose. Build something that isn’t about the founder’s ego; build for a mission bigger than any one person. And when great teammates grow into leaders elsewhere and start their own businesses, celebrate it as proof the culture works, not as a loss. OnMilwaukee was always a calling to make Milwaukee better.
How did your early work in government and civic projects prepare you for leadership in media and business?
My early government work crystallized how progress often depends on three pillars—public, private, and nonprofit — working in concert. Seeing how policy, capital, and community align made later leadership decisions more grounded and system-aware.
What skills do you consider essential for young professionals entering media, marketing, or community-focused careers today?
Curiosity, curation, creativity, and connection-building still differentiate. These are uniquely human skills—and remain resilient alongside AI—especially the discipline of curation: synthesizing the what, the how, and the why into insight that moves people to act.
You’re known for “connecting dots” between people, organizations, and ideas. How can someone intentionally build that kind of networking ability?
Make networking a place to give, not get. A former boss, Joe Sweeney, taught a simple cadence: Be a wingman, ask “How can I help?”, follow up with handwritten notes, set daily outreach goals, and make it enjoyable so consistency sticks.
With so many hats—radio host, CMO, CEO, board chair—how do you personally stay adaptable and keep learning?
Another Joe Sweeney-ism applies: “If you stop, you die.” Keep swimming with persistence, passion, and purpose. Let enthusiasm—“En Theos”- the God within fuel the work, learn from mistakes without losing identity, and trust that what’s on the plate is there for a reason.
Media and marketing have shifted dramatically over the last two decades. What do you see as the biggest opportunities for early-career professionals right now?
“Be yourself” is the typical advice, but you really have to be an amplified version of the best you. Figure this out - and you’ll soar. Be distinctive, not generic. Three lanes are compounding: AI-powered creative and growth, first‑party data activation, and the creator/streaming ecosystem; learn the business models beneath them, not just the tools.
You’ve been a leader in digital content since before it was mainstream. What advice do you have for someone trying to stand out in today’s saturated content environment?
Again, be an amplified version of the highest and best you. Have a personal mission statement, a board of directors that can provide feedback and create for the best version of you - don’t try to be someone else. Take tips and advice from those you admire.
But in a world where everyone is a media company - we all need to find content lanes that matter to many and few at the same time. Does this make sense? Great brands are local and national at the same time because they know their why and it’s baked into their culture. Borrow tactics from admired creators, but ship work that is locally resonant and broadly relevant. Standing out in a saturated content environment takes a diligent, consistent branding approach.
What’s the best career advice you’ve ever received, and how has it guided you?
Free advice is worth what you pay for it—seek skin-in-the-game counsel. A city is only as good as the stories it tells—choose to tell good ones. And, live the 1/3 rule: one-third amazing, one-third okay, one-third challenging; build habits to navigate whichever third today is. I’ve been blessed to have amazing friends, parents and family (thank you, Stephanie, Jake and Pierce) who have supported my craziness and embraced the life-work synch that’s needed to “do it all.” Having a family that’s open to this makes work not feel like work and makes life that much more meaningful.
If you could give one piece of advice to your younger self at the start of your career, what would it be?
People are people. I knew this, but when you’re younger you have a tendency to think someone is more important than another - and, while this can be the case - people are always just people. Be willing to share fears and failures, know that we all have them. And, to not fear detours; they often became the foundation for many of my best opportunities.
For professionals in the Midwest who want to make an impact locally but think opportunities are only in bigger markets, what would you say?
Be an evangelist -- a passionate evangelist for where you live. Position and promote whenever you can - recruitment and retention is about all of us - getting off the sidelines and getting involved in causes helps create impact - doing the unglamorous work of community building has an impact that is often faster and more durable in smaller markets precisely because participation compounds.
How do you define success now, compared to when you started your career?
Ah, the define success question. I love it!
I hope - through the years - that I’ve stayed true to my definition that’s a bit of a spin on something some people say Churchill once said - success is going from failure to failure with enthusiasm as we live with and for others. A good Jesuit principle too - Marquette University taught me well. Onward.
Jeff Sherman is one of Big Shoes Network's leaders to follow on LinkedIn
