Midwest Leadership Speaker: Khary Penebaker
TL;DR: Khary Penebaker is a Midwest-based leadership speaker available for keynotes, workshops, and panel discussions across Wisconsin, Illinois, Minnesota, Michigan, Iowa, Indiana, and Ohio. His talks on leadership under pressure, resilience, and team building draw from 20+ years of business ownership and national media experience.
Leadership speaking for the Midwest
The Midwest builds things. Manufacturing, construction, agriculture, healthcare, logistics. These industries run on practical leadership, not corporate buzzwords. Khary Penebaker speaks to Midwest audiences because he is one. He has built and run companies in Wisconsin, managed teams across multiple states, and understands the work ethic and values that define this region.
His keynotes connect with Midwest audiences because they are grounded in real experience. No motivational fluff. No recycled TED Talk material. Khary shares hard-won lessons from growing a $1.5M company to $15M, managing 180+ employees, running for Congress, and turning personal tragedy into national advocacy.
Core speaking topics
- Leadership Under Pressure – Decision-making when the stakes are high and the margin for error is thin. From construction job sites to political campaigns, Khary has led through situations where failure was not an option.
- Building Resilient Organizations – How to create teams and cultures that survive setbacks and come out stronger. Based on his experience rebuilding after business loss and personal tragedy.
- Workforce Development in the Trades – The skilled trades face a generational talent crisis. Khary brings perspective from years in construction, roofing, and sheet metal on how to attract, train, and retain skilled workers.
- From Adversity to Advocacy – Turning personal pain into public purpose. Khary lost his mother to gun violence at 20 months old. His story of channeling grief into action resonates across any industry.
Midwest markets and regions
Khary speaks at events throughout the Midwest. Based in Pewaukee, Wisconsin, he regularly travels to:
- Wisconsin – Milwaukee, Madison, Green Bay, Waukesha, Racine, Kenosha, Fox Valley
- Illinois – Chicago, Rockford, Naperville, Springfield, Peoria
- Minnesota – Minneapolis, St. Paul, Rochester, Duluth
- Michigan – Detroit, Grand Rapids, Lansing, Ann Arbor
- Iowa – Des Moines, Cedar Rapids, Iowa City, Davenport
- Indiana – Indianapolis, Fort Wayne, South Bend, Evansville
- Ohio – Columbus, Cleveland, Cincinnati, Dayton
National engagements are also available. Khary has spoken at events across the country and appears regularly on national media including CNN, MSNBC, NPR, and PBS.
Industries and audiences
Khary has delivered keynotes and workshops for audiences across these sectors:
- Construction and Trades – Industry conferences, safety summits, workforce development programs
- Corporate Leadership – Executive retreats, management training, annual meetings
- Nonprofit and Advocacy – Fundraising galas, board retreats, community events
- Healthcare – Wellness conferences, leadership development, resilience training
- Education – University commencements, faculty development, student leadership programs
- Government and Public Sector – State agency conferences, legislative forums, public safety events
What sets Khary apart
Most speakers fly in, deliver a talk, and fly out. Khary lives in the Midwest. He runs businesses here. He is raising his family here. That connection to the region shows in every keynote because he is not talking about Midwest values from the outside. He is living them.
His combination of entrepreneurial experience (growing companies from startup to $35M+ revenue), political experience (Congressional candidate, DNC representative), media savvy (regular contributor on national networks), and personal story creates a speaker unlike anyone else on the circuit.
Book a Midwest speaking engagement
Planning an event in the Midwest? Request availability or call 414-349-5009. Early booking is recommended for peak conference season (September through November and January through March).
Frequently asked questions
Do you charge travel fees for Midwest events?
Events within driving distance of Pewaukee, WI (roughly 4 hours) typically have no additional travel costs. For events requiring air travel or overnight stays, travel expenses are discussed during the booking process.
Can you speak at multi-day conferences?
Yes. Khary can deliver a keynote on day one and facilitate a workshop on day two, or participate across multiple sessions. Multi-day engagements are available at a packaged rate.
What size audience works best for your talks?
Khary has spoken to audiences from 20-person executive retreats to 2,000+ conference attendees. The content and delivery style adjust based on audience size and format.
Do you offer virtual speaking options?
Yes. Virtual keynotes and hybrid events are available. Khary has delivered virtual presentations for national organizations and can accommodate remote audiences with professional production quality.
Based in Wisconsin? Visit the dedicated Wisconsin Keynote Speaker page for state-specific information. View all speaking topics.
Last updated: March 9, 2026