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.
Why This Episode Matters
This episode reinforces the mindset required to move forward: learning constantly, working hard, and embracing discomfort when necessary. When you combine grit with thoughtful planning and strong partnerships, you create the environment where meaningful growth and opportunity can happen.
In this Episode, We Discuss:
- Success starts with intention.
- Relationships drive growth.
- Growth lives outside your comfort zone.
- Grit matters more than fear.
Conversation Takeaways
- 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.
A Quote To Remember
“When you’re first starting out, all you have is time. Make the most of it and put yourself in a position to get lucky.” – Jay Leonard
Light Bulb Moments – Episode 91
Make It Happen: Grit, Growth, and Getting Lucky with Jay Leonard
The Light Bulb Moment of This Episode
Success is built on learning, grit, and intentional action. When you embrace fear, protect your time, and build strong partnerships, you create the conditions where opportunity and “luck” can appear.
Light Bulb Moments & Reflections from the Episode
- Learning is foundational to success.
Continuous learning drives growth and new opportunity.
- Don’t try to be everything to everyone.
Focus creates stronger businesses and clearer direction.
- Build through strategic partnerships.
Collaboration expands what you can accomplish.
- Time is your most valuable asset.
Protect it and use it intentionally.
- Grit and hustle matter.
Persistence and hard work move ideas into action.
- Fear can be a motivator.
Being afraid is natural — use it to push forward.
- Trust grows through connections.
Relationships strengthen business and opportunity.
- Step outside your comfort zone.
New experiences can build confidence and self-awareness.
- Take advantage of opportunities.
Opportunities often disappear if you hesitate.
- Everything starts with planning.
Clear planning helps turn ideas into results.
Connect with Jay Leonard:
Website: https://www.bernstein.com/about-us/locations/chicago/jay-leonard.html
LinkedIn: https://www.linkedin.com/in/jayleonardbernstein/
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