About Jessica
Built on Relationships, Driven by Legacy
I'm Jessica Lepore — a business owner, financial advisor, coach, and community builder. I'm on a mission to acquire and grow one exceptional small business, and to do it the right way.
My Story
From Family Business to Acquisition Entrepreneur
I grew up in the world of small business. For over a decade, I helped run Chili Discount Liquor — a family-owned retail business in Rochester, NY. I learned firsthand what it takes to build customer loyalty, manage a team, and keep a community business thriving year after year.
That experience gave me something no MBA can teach: a deep respect for what business owners build. The relationships, the reputation, the culture — these things matter. They're not line items on a balance sheet.
After graduating from SUNY Buffalo State College, I expanded my expertise into financial planning and wealth management as a Financial Advisor at New York Life Securities LLC. This gave me the analytical tools to evaluate businesses rigorously — and the perspective to understand what sellers are really giving up when they hand over the keys.
Throughout my career, I've also been a coach — youth soccer, basketball, and lacrosse. Coaching taught me how to develop people, build teams, and lead with patience and purpose. These are the same skills I bring to every business I consider acquiring.
Core Values
Legacy First
I believe every business has a story. My job is to honor that story while writing the next chapter. I don't acquire businesses to strip them — I acquire them to grow them.
Transparency Always
I say what I mean and mean what I say. No games, no lowball offers, no surprises in due diligence. Sellers deserve honesty at every step of the process.
Continuous Learning
I'm a student of business. I read, I study, I seek mentors. I bring intellectual curiosity and a growth mindset to every business I evaluate and operate.
Career Timeline
Experience That Shapes My Approach
SUNY Buffalo State College
Bachelor's Degree
Graduated with a foundation in business and leadership. The academic rigor complemented the hands-on business experience I was already accumulating in the family business.
Retail Operations Manager
Chili Discount Liquor (Family Business)
Led day-to-day operations of a family-owned retail business for over a decade. Developed deep expertise in inventory management, customer relationships, staff leadership, and community engagement.
Youth Sports Coach
Soccer, Basketball & Lacrosse
Coached youth athletes at Churchville-Chili High School, Webster Thomas High School, and Chili Soccer Association. Built leadership, teamwork, and community roots that inform how I lead businesses today.
Financial Advisor
New York Life Securities LLC
Advising clients on financial planning and wealth management. This role deepened my analytical capabilities and gave me a sophisticated understanding of business valuation, deal structuring, and financial due diligence.
My Philosophy
Business is About People
I believe the best businesses are built on relationships — with customers, employees, and the community. When I acquire a business, I'm not just buying assets. I'm inheriting relationships that took years to build.
My approach is to listen first. Every business has a unique story, and every seller has a unique set of goals. Some want to retire. Some want to pursue a new venture. Some want to ensure their employees are taken care of. I take the time to understand what matters most to you.
I'm passionate about teaching and inspiring others to create lasting success. Whether it's coaching youth athletes, advising financial planning clients, or leading a business team — I lead with empathy, clarity, and a genuine commitment to the people I work with.
I want to be the kind of buyer that sellers feel good about — someone who honors what they built and takes it further.
Jessica LePore
Founder, LEAP Acquisitions
Let's Connect
I'd Love to Hear Your Story
Whether you're ready to sell or just exploring your options, I'm always happy to have a confidential conversation. No pressure, just an honest dialogue.