Welcome to the Chicago Business Leaders Podcast. Each month we bring you insights from Leaders throughout the Chicago Middle-Market Business Community. Listen in as we discuss leadership styles, industry trends and topics, and other key items affecting the Business community.
How Listening Transforms Leadership with Jessa Baker
In this episode, Scott Moran sits down with Jessa Baker, CEO of Levenfeld Pearlstein, to discuss her career journey and the leadership lessons she's learned along the way. From her early ambitions as a determined ten-year-old to leading high-performing teams and flying across continents as a law firm strategy consultant, Jessa shares how a passion for organizational development and a commitment to listening have shaped her leadership style.
Jessa sees leadership as a dynamic, evolving practice that's about asking the right questions, listening intently, and taking decisive action. Her biggest breakthrough was embracing authenticity, especially through direct engagement with her team. One innovative approach is her "Jamming with Jessa" sessions, where every member of the firm can submit anonymous questions for open discussion. She shares times when simply hearing people out made all the difference, especially in high-stress consulting environments.
At Levenfeld Pearlstein, this people-centered yet business-driven ethos distinctly sets the firm apart. Attorneys are accountable for legal outcomes and cultural stewardship, which translates into a consistently exceptional client experience. Culture is embedded in daily practices, from meaningful feedback and high expectations to charitable involvement, such as their support for the Greater Chicago Food Depository.
Connect with Jessa at Levenfeld Pearlstein:
🌐https://www.lplegal.com/
Email: jbaker@lplegal.com
Jessa Baker on LinkedIn: https://www.linkedin.com/in/jessa-baker-a182b28/
Connect with Scott:
🌐 https://sutkermoran.com/contact-us/
Email: smoran@sutkermoran.com
📍 Presented by Sutker Moran — Chicago's trusted partner for business consulting and CFO services.
28 Jul 2026
Leading with Purpose with Scott Rudin
In this episode of the Chicago Business Leaders Podcast, Scott Moran sits down with Scott Rudin, Managing Partner at MDR Law and Co-founder and President of Helping Hands Network. They discuss the journey of building a leading litigation firm in Chicago over the past 22 years, including the values, relationships, and leadership strategies that have sustained its success.
Scott Rudin shares the story behind founding MDR Law, sharing how the firm was built on word-of-mouth referrals, and a client-first approach that prioritizes personal involvement at every stage—from initial consultations to trial. He discusses what sets MDR Law apart in a highly competitive market, including strong regional expertise and a track record of building cross-state partnerships to handle complex cases.
Scott also reflects on some of the lessons learned from his early mentors and discusses how investing in staff, fostering an environment of respect and input, and promoting from within have contributed to the firm's stability and growth. He also describes his evolution from a more hands-on manager to someone who empowers his team, emphasizing the importance of trust and openness to new perspectives.
The episode also shines a spotlight on Scott's passion for philanthropy. He shares the origins of Helping Hands Network, a charity that supports children and young adults with developmental disabilities. Their conversation also dives into how personal experience fuels his ongoing commitment to community work.
Connect with Scott at MDR Law:
🌐https://www.mdr-law.com/
🌐https://www.helpinghandstoday.org/
Email: scott@mdr-law.com
Cell Number: 312-730-7292
Scott Rudin on LinkedIn: https://www.linkedin.com/in/scott-rudin-01851b45/
Connect with Scott Moran:
🌐 https://sutkermoran.com/contact-us/
Email: smoran@sutkermoran.com
📍 Presented by Sutker Moran — Chicago's trusted partner for business consulting and CFO services.
28 Jul 2026
Leadership as Stewardship with Robert Meyers
In this episode of the Chicago Business Leaders Podcast, Scott Moran is joined by Robert Meyers, newly appointed CEO of Republic Business Credit, for a conversation all about leadership, career pivots, and building trust with clients and teams. Rob shares more about his unlikely path from a pre-med biology major headed toward neurosurgery to twenty years in asset-based lending and factoring, and shares how questioning his own motivations at 22 years old set the direction for the rest of his career.
We discuss how Rob's outsider background in an industry dominated by finance and accounting professionals shaped his leadership style which is rooted in a constant willingness to ask "why" rather than assuming he has the answers. He reflects on his volunteer leadership roles as past president of both the Secured Finance Network (SFNet) and the Turnaround Management Association (TMA), and describes his commitment to stewardship and leaving each organization better than he found it.
Rob offers his advice to young professionals and emerging leaders: make mistakes early, seek outside perspective before reacting in the heat of the moment, and recognize that asking for help is a strength, not a weakness. He shares personal stories of early-career missteps and the mentors who helped him course-correct, along with practical strategies for managing emotional decision-making under pressure. We also dig into why Rob personally interviews every new hire at Republic Business Credit, and the firm's "no jerk policy" for building a culture people want to be part of.
Connect with Rob at Republic Business Credit:
🌐https://republicbc.com/team-bio/robert-meyers/
Email: rmeyers@republicbc.com
Rob Meyers on LinkedIn: https://www.linkedin.com/in/robmeyers2/
Connect with Scott:
🌐 https://sutkermoran.com/contact-us/
Email: smoran@sutkermoran.com
📍 Presented by Sutker Moran — Chicago's trusted partner for business consulting and CFO services.
30 Apr 2026
Building a Trusted Brand: Howard Ankin's Approach to Leadership and Building a Brand
In this episode of the Chicago Business Leaders Podcast, Scott Moran is joined by Howard Ankin, co-founder of Ankin Law, for a conversation tracing the evolution of a leading Chicago law firm over the past 29 years. Howard reflects on starting his journey with just himself and a computer, and walks through the firm's growth into an organization with nearly 90 professionals, including 28 lawyers.
Our discussion highlights the persistent drive required to scale a professional services practice, the strategic decisions behind brand-building, and the ways in which market and societal shifts.
Howard shares his leadership philosophy, rooted in leading by example and a genuine commitment to supporting career-long employee growth. He describes the adaptation in management style prompted by changing workforce dynamics, flexibility with remote work, and an openness to new ideas as key pillars of his approach. You'll hear some great insights into balancing traditional values with the need to remain responsive to modern expectations, all while building lasting trust and engagement within the organization.
Connect with Howard at Ankin Law:
🌐 https://ankinlaw.com/
Email: Howard@ankinlaw.com
Howard Ankin on LinkedIn: https://www.linkedin.com/in/howard-ankin-9671743/
Connect with Scott:
🌐 https://sutkermoran.com/contact-us/
Email: smoran@sutkermoran.com
📍 Presented by Sutker Moran — Chicago's trusted partner for business consulting and CFO services.
30 Mar 2026
Defining Moments: A Leader's Turning Point with Sean Gallagher
In this episode of the Chicago Business Leaders Podcast, Scott Moran sits down with Sean Gallagher, Executive Vice President and Regional President at Busey Bank, to explore what leadership really looks like after 30 years in the banking industry.
Sean shares a powerful perspective on leadership, built around trust, accountability, and curiosity. He breaks down the idea of having a "strong back, soft front, and wild heart", balancing empathy with the ability to make tough decisions and lead with integrity.
The conversation dives into one of the defining moments of his career, a major financial downturn that reshaped how he thinks about risk, due diligence, and relationships. Sean explains how failure became his greatest teacher, reinforcing the importance of doing things the right way, even when it's hard.
They also discuss how Busey Bank differentiates itself through a high-touch, relationship-driven approach, combining commercial banking with top-tier wealth management services. Sean highlights the importance of seeing clients holistically and building long-term trust.
Finally, Sean shares his outlook on today's economic environment, emphasizing the impact of global uncertainty and why business leaders should stay focused on fundamentals, control costs, and lean on trusted advisors.
This episode is a thoughtful look at leadership, resilience, and navigating uncertainty in today's business world.
Connect with Sean at BMO:
🌐 https://www.busey.com/ (https://www.busey.com/)
Email: sean.gallagher@busey.com
Sean Gallagher on LinkedIn: https://www.linkedin.com/in/sean-gallagher-7148199/
Connect with Scott:
🌐 https://sutkermoran.com/contact-us/
Email: smoran@sutkermoran.com
📍 Presented by Sutker Moran — Chicago's trusted partner for business consulting and CFO services.
24 Nov 2025
Why Most Banks Miss the Mark on Client Relationships — and How BMO Gets It Right
Host Scott Moran interviews BMO Managing Directors Rob Hallberg and Matt Stefani about BMO's client-centric approach and leadership strategies for building trust and driving growth.
31 Oct 2025
Building a Best Place to Work: Chris Gallagher on Leadership, Culture, and Growth at Green Office Partner
Host Scott Moran interviews Chris Gallagher, co-founder of Green Office Partner, about building a top workplace through leadership, culture, and strategic growth.
1 Aug 2025
Future-Proofing Your Business: Succession, Tax, and Talent Strategies from FGMK’s Lee Singer
Host Scott Moran interviews FGMK partner Lee Singer on future-proofing businesses through succession, tax, and talent strategies.
16 Jun 2025
Why Strategic Planning Is Essential for Business Growth
Andy Hartlieb, CEO of American Community Bank & Trust, discusses strategic planning and leadership with Scott Moran, highlighting the importance of team culture and personalized service in Chicago's evolving banking sector in this interview.
19 May 2025
From Startup to 100+ Lawyers: How Patrick Croke is Redefining Big Law with Servant Leadership
Host Scott Moran interviews Patrick Croke, founding partner at Croke Fairchild Duarte and Beres, about scaling a law firm through servant leadership and entrepreneurial thinking.
23 Apr 2025
Leadership That Lasts: How Wintrust’s Bob Shanahan Built a Team That Stays and Clients That Trust
Wintrust's Bob Shanahan shares with host Scott Sutker how his people-first leadership builds loyal teams and enduring client trust through transparency and proactive planning.
13 Mar 2025
The Chicago Business Leaders Podcast - Coming Soon
Host [Host Name] interviews Chicago business leaders, sharing insights from their successes and failures to inform listeners.
9 Sept 2024
Intro to the Chicago Business Leaders Podcast
Host John Smith interviews industry experts for actionable business advice and strategies.
Who has been a guest on Chicago Business Leaders
Names identified in recent episode analyses. Showing up to five guests.
Rob Hallberg
Matt Stefani
Chris Gallagher
Lee Singer
Andy Hartlieb
Reach and audience
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Apple Podcasts (US)
5.0 / 5
2 ratings
Podcast Authority Score: 13 / 100
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Quality
14
Social presence
0
YouTube
0
Engagement
32
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