Episode 91: Make It Happen: Grit, Growth, and Getting Lucky with Jay Leonard

Jay Leonard is a Managing Director in Bernstein Private Wealth Management’s Chicago office, where he helps lead strategy and growth in Chicago and the Midwest markets. As a Principal of the firm & co-leader of the business owner and entrepreneur task force, he also advises clients and their professional advisors regarding asset allocation, investment strategy, tax & estate planning, cash management, business transactions, and charitable giving plans. In advising the complex needs of business owners, entrepreneurs, and corporate executives, Jay and his team are fully supported by the breadth and expertise of Bernstein’s wealth strategies group and family engagement team. He has extensive experience working with Foundation & Institutional clients as well. Before joining Bernstein in 2009, Jay was a private wealth advisor at Morgan Stanley Private Wealth Management, advising the firm’s largest private clients. Earlier, he was a strategy consultant with Marsh & McLennan, and before that, a research & trading analyst with the global equity derivatives group at Credit Suisse. Jay earned an MBA from Kellogg School of Management at Northwestern University and a BA in finance and economics from Bucknell University, where he also competed as a Division I swimmer. Jay serves on the board of directors for YPO Chicago-Windy City Chapter and on the membership engagement committee for the Economic Club of Chicago. Additionally, he serves on the board of Entrepreneurial Youth Experience (E.Y.E) at Chicago Hope Academy and is chairman emeritus for the Boy Scouts of America, National Eagle Scout Association (NESA)-Chicago. He lives in Wilmette, IL, with his wife, Tyra, and their two children. Jay is an avid triathlete, cyclist, and loves to surf the oceans whenever offered the opportunity outside of the Midwest. Despite his Chicago ties, Jay can often be found rooting for Philadelphia sports teams, his hometown.

In this episode, we discuss:

Success starts with intention.
Relationships drive growth.
Growth lives outside your comfort zone.
Grit matters more than fear.

Lightbulb Moments:

Planning, focus, and the willingness to say no help clarify your path and protect your most valuable asset—time.
Strategic partnerships and genuine personal connections are powerful tools for building trust and expanding your business.
Whether it’s trying stand-up comedy or seizing an unexpected opportunity, stepping into the unknown fuels learning and resilience.
Fear can motivate, but it’s grit, hustle, and a commitment to continual learning that sustain long-term success.