Overview
The energy is high. The conversation is engaging. The vibe is positive. No gotcha questions or surprises. We send guests questions in advance and invite our guests to suggest questions that allow them to tell their story. We want our guests to proudly talk about their purpose, accomplishments, and legacy. Willingly host Will Holmes invites and interviews extraordinary leaders who have created successful careers, built businesses, led communities, and who have found happiness and meaningfulness while making a positive impact on others. Through these candid conversations, we examine how these individuals found the courage to pursue their passions, fulfill their purpose, and achieve remarkable success. We believe their journeys will motivate and inspire our audience to reach their highest potential.
The Willingly audience demographics are business owners, aspiring entrepreneurs, elected officials, and government leaders in the DC, MD, VA area and beyond. These are high-income individuals who want to acheive greatness in their personal and professional lives.
Willingly Webcast Sample Guest Questions
- Before you had a title, a business, or a platform, what was an early experience in your life that quietly set the trajectory for why you care about serving others today?
- Leadership always requires a personal toll. What is one quiet sacrifice you’ve willingly made behind the scenes that the public rarely sees or understands?
- When pressure mounts from politics, competition, or public opinion, what is the one core conviction you refuse to compromise on, no matter what?
- Can you tell me about a moment when walking away or choosing the easy route would have made total sense—and what made you decide to stay in the fight instead?
- What’s a personal habit, passion, or quirk about you that would completely surprise people who only know you through your professional persona?
- Forget the headlines, major deals, or official awards. What is one small, quiet moment of impact you made for a single person that you will carry with you forever?
- When you have to make a choice that you know won’t be popular, where do you go internally to find the clarity and courage to step forward anyway?
- When you look around our community today, what is the specific problem or gap that gets you up early in the morning and keeps you fighting?
- Decades from now, when you look back on this chapter of your life, what do you want people to feel when they remember the work you did?
- Leadership and public service can often feel thankless and relentless. Why do you willingly step into the arena every day to carry burdens for people you may never even meet?
Past Guests
So far, our guest include:
Anne Arundel County Executive Steuart Pittman
Logistics
We work with you and your team to schedule a one hour session. That includes, our equipment set up, a 30 minute interview, and break down of our equipment. We can come to you, or you can come to us in Baltimore, MD. We share the footage with you after the recording and we invite you to share the final interview on social media.
About Willingly Host, Will Holmes
Will Holmes is Founder of Will Holmes Consulting (WHC), an award-winning firm that has guided over 12,000 entrepreneurs since 2006. WHC’s 8-week entrepreneurship curriculum has developed over 1000 graduates across 11 programs, including numerous accelerators in Baltimore City and counties including Anne Arundel, Caroline, Charles, Dorchester, Prince George’s, and Talbot, with over 80% increasing revenue and creating jobs in their communities. Our curriculum won a 2026 Silver Award from the International Economic Development Council. Additionally, WHC’s economic impact has been recognized by the U.S. Small Business Administration and WHC was selected as the 2024 Maryland Minority Business of the Year. Will Holmes has developed technical and economic development solutions for federal, state and local government agencies, financial institutions, and universities across the globe.
Next Steps
Contact Will Holmes at will@whcusa.com to discuss details and scheduling. Thank you!