Jesse di Lillo

About Jesse di Lillo

Building real wealth - one patient decision at a time. For 17+ years, I’ve focused on acquiring, improving, and holding investments to build lasting equity - not chasing the next hot deal.Early on, I learned “quick wins” rarely compound into anything meaningful. Seeing cycles play out in real time made one thing clear: patience isn’t passive - it’s strategic. That realization shaped how I invest and how I evaluate opportunities.My approach is simple: Time in the market beats timing the market.I believe in: • Buying well • Improving fundamentals • Holding through cycles • Exiting when value is fully realizedThese are 5–10 year plays - guided by judgment, structure, and discipline - not hype or constant motion. The goal isn’t to be the loudest or the fastest, but to build something that endures and compounds over time.As a result, I’m often brought in by operators and investment groups when high-stakes decisions are on the table - capital allocation, strategy, and execution. Not to reinvent what already works, but to pressure-test assumptions, strengthen structures, and help ensure decisions stand the test of time.I don’t optimize for attention.I optimize for outcomes.If this resonates, a conversation tends to follow.InvestWithJSJ.com

Experience

1. Partner

   Dealworthit

   May 2023 — Present · US

   Streamline Your Deal AnalysisOur AI-powered software simplifies underwriting and analyzing multifamily deals, saving you time and increasing accuracy. Move from weeks of manual analysis to minutes with our all-in-one solution.Experience Efficient Deal Analysis with DealWorthItStop wasting time on spreadsheets and inaccurate data. Use our AI-driven software to quickly underwrite and analyze your multifamily investments.

Education

• Northland College

  Bachelor of Science (B.S.)

  2012 — 2016

• Danville High School

  High School, College Prep

  2008 — 2009

Skills

• Roofs
• Lead Generation
• Investment Properties
• Marketing
• Microsoft Office
• Sales
• Facebook
• Project Tracking
• Oil & Gas Services
• Management
• Team Building
• Gas Distribution
• Business Management
• Social Networking
• Customer Service
• Teamwork
• Whole House Renovations
• Gas Distribution
• Auto Detailing
• Mechanical Fusion
• Progress Tracking
• Painting
• Social Media
• Sustainable Business
• Working with Investors
• Sustainable Energy
• Spreadsheets
• Materials Management
• Green Building
• Rental Real Estate
• Leadership
• Dump Truck
• Electrofusion
• Time Management
• Real Estate Transactions
• Basic Gas
• Natural Gas
• Field Mapping
• Residential Homes
• Butt Fusion 1"-8" Pipe