Investor | Capital Advisor | Strategic Consultant | Milwaukee, WI | I’m an investor, capital advisor, and business builder with a portfolio spanning 2,000+ multifamily units, self-storage, short-term rentals, and high-margin consumer brands.
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Hello, I'm
Jesse DiLillo
Investor | Capital Advisor | Strategic Consultant | Milwaukee, WI | I’m an investor, capital advisor, and business builder with a portfolio spanning 2,000+ multifamily units, self-storage, short-term rentals, and high-margin consumer brands.
? About Me
I’m an investor, capital advisor, and business builder with a portfolio spanning 2,000+ multifamily units, self-storage, short-term rentals, and high-margin consumer brands. Through Invest with JSJ, I help operators raise capital, structure deals, and scale with confidence.
My work spans:
- Private equity real estate
- Digital marketing + growth
- AI-based underwriting
- Startup investing
Whether it’s structuring investor-ready offerings or launching multi-channel campaigns, I partner with founders and operators to accelerate growth and increase enterprise value.
? Open to co-GP partnerships, strategic consulting, and equity-based marketing collaborations.
? Off the Clock
Former hockey, soccer, and lacrosse goalie — I bring the same focus, grit, and calm-under-pressure mindset to every deal I touch.