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Jesse Di Lillo

@jessedilillo

11.3K
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Helping entrepreneurs & athletes allocate capital.
Commercial real estate investor + advisor.
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Yesterday already happened. Tomorrow isn’t here yet. The only day you can actually do something about is today. So stop replaying the deal you missed. Stop spinning on the one that hasn’t closed. Do the next right thing in front of you. Win or learn. That’s the whole game. Which one are you stuck on right now, yesterday or tomorrow? by @jessedilillo
4
a month ago
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I wrote most of this somewhere between airports. It reminded me of a lesson that took me years to learn... For a long time, I wore free underwriting like a badge of honor. Someone would text me a rent roll and a T-12 at 10 p.m., and I'd spend my evening running the numbers. No invoice. No equity. No engagement letter. Just, "Happy to help." I convinced myself I was building relationships. In reality, I was teaching people that my highest-value skill had no price. Over time, I realized something uncomfortable: I was spending a significant portion of my calendar underwriting other people's deals, answering follow-up questions, stress-testing assumptions, and helping them avoid costly mistakes. Many of those deals eventually closed. Sometimes I found out through LinkedIn. Sometimes I wasn't even included in the thank-you text. The biggest lesson wasn't about underwriting. It was about boundaries. The work I was giving away for free is the same work underwriters and investment professionals at private equity firms are paid hundreds of thousands of dollars to do because good underwriting protects capital, uncovers risk, and improves decision-making. I wasn't undervaluing the work. I was undervaluing my own time. Today, I still love helping operators and investors. That's never changed. What has changed is understanding the difference between being generous and becoming someone else's free analyst. Those aren't the same thing. Once I started protecting my calendar and charging appropriately for the value we deliver, two things happened: • My income increased. • My peace of mind increased. Interestingly, the people who genuinely valued the work stayed. The people who were only looking for free labor quietly disappeared. That alone made the decision worthwhile. If you're an underwriter, capital advisor, consultant, or operator who keeps saying yes because you genuinely care, I understand. I've been there. Just remember: Your expertise is valuable because it helps people make better decisions with millions of dollars. Don't be afraid to treat it that way. by @jessedilillo
0
2 months ago
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How many deals did you underwrite last week? I analyzed 60 deals in the last 7 days with DealWorthIt. Not every deal deserves hours inside a spreadsheet. Sometimes you just need to identify the obvious issues, pressure-test the assumptions, and decide whether it is worth deeper underwriting. How many did you analyze last week? dealworthit.com by @jessedilillo
1
2 months ago
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Tired of wasting hours manually copying T12s & rent rolls into spreadsheets? With DealWorthIt 2.0, underwriting multifamily deals takes seconds. 1️⃣ Drag & drop your T12 and rent roll files 2️⃣ Review auto-extracted income & expense data 3️⃣ Get instant property analytics Stop fighting Excel and speed up your deal flow today. 👇 Try it out now below! by @jessedilillo
0
3 months ago
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A broker sends you a multifamily deal asking $60 million. You upload the T-12 and rent roll. Seconds later, you see: • 1.02 debt-service coverage\ • 0.23% cash-on-cash return\ • $4.6 million required at refinance You do not need to spend the next three hours underwriting it. Deal Worth It helps multifamily investors quickly identify obvious issues, pressure-test opportunities, and determine whether a deal deserves deeper underwriting. Bad deal? Save it, watch for a price reduction, and mov by @jessedilillo
0
3 months ago
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Making Money and Allocating Money Are Different Skills Making money and allocating money are two completely different skill sets. A lot of athletes, entrepreneurs, and high-income earners spend years mastering how to earn. But deciding where capital should go, how risk should be evaluated, and how disciplined investment decisions are made is a separate skill entirely. That is where Pinnacle One helps bridge the gap. Educational only. For accredited investors only. Not investment advice or an offer to sell securities. by @jessedilillo
3
4 months ago
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Most passive investors only understand the LP side of a deal. They invest, wait for distributions, and hope the operator executes. But when you understand the difference between the LP and GP position, the structure starts to matter a lot more. At Pinnacle, we’re investing through an allocation fund designed to access stronger economics than a traditional LP position. That means our investors can benefit from the deal-level returns plus early fee income that can help boost IRR and return capital sooner than a standard limited partner structure. Same real estate thesis. Better alignment. Stronger economics. More ways to win. That’s the difference. #PinnacleOneCapital #RealEstateInvesting #MultifamilyInvesting #PassiveInvesting #AlternativeInvestments by @jessedilillo
0
4 months ago
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Great deals don’t need endless extensions. If the numbers are truly compelling, the capital usually shows up. But when the deal keeps needing more time… Another extension. Another delay. Another reason the raise is not done yet. That usually tells you there is a problem with the story. Maybe the price is too high. Maybe the risk is being underwritten too lightly. Maybe the investor base is not buying the assumptions. A great deal creates urgency. A questionable deal creates excuses. Before you keep extending timelines, step back and ask the real question: Is the market slow… Or is the deal just not strong enough? by @jessedilillo
0
4 months ago
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One of the biggest mistakes I see operators make is confusing conviction with validation. Just because you're confident in a deal doesn't mean you're right. Institutional investors understand this. That's why they rarely rely on a single opinion before deploying capital. They have analysts, investment committees, third-party reviews, and multiple layers of diligence designed to challenge assumptions before money gets wired. Yet I regularly see operators making $5M, $10M, and $20M+ decisions based primarily on their own underwriting and perspective. That's not confidence. That's concentration risk. The goal isn't to eliminate risk. Every investment carries risk. The goal is to eliminate avoidable mistakes. The larger the transaction, the more valuable independent review becomes. What's your process for pressure-testing a deal before you close? #CommercialRealEstate #Multifamily #PrivateEquity #RealEstateInvesting by @jessedilillo
0
4 months ago
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This is where bad operators expose themselves. When the deal starts falling apart… When multiple people are pointing out red flags… When the underwriting no longer makes sense… When the assumptions are clearly wrong… And they still push forward because they already wired the deposit. That is not conviction. That is ego. Losing $50,000 hurts. But risking millions of dollars of investor capital because you don’t want to admit you were wrong is unacceptable. Sometimes the best investment decision is walking away. Take the loss. Protect the investors. Move on to the next deal. Before you wire money, ask yourself: Would this sponsor protect my capital… Or protect their own ego? #RealEstateInvesting #MultifamilyInvesting #InvestorProtection #DueDiligence #DealReview #PassiveInvesting by @jessedilillo
0
4 months ago
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Everybody gets paid when a deal closes. The broker gets paid. The lender gets paid. The attorney gets paid. The seller gets paid. The question is: Who's getting paid to tell you not to do the deal? That's often the missing seat at the table. Every acquisition should have someone whose job is to challenge assumptions, pressure-test the numbers, and protect the downside. The larger the transaction, the more important that role becomes. #CommercialRealEstate #PrivateEquity #MultifamilyInvesting by @jessedilillo
0
4 months ago
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The most dangerous person in your next acquisition might be you. Not because you're inexperienced. Because once you fall in love with a deal, objectivity disappears. I've seen operators justify bad assumptions, overlook red flags, and ignore obvious risks because they wanted the deal to work. That's why institutional investors use investment committees. They don't rely on one opinion. They challenge assumptions before capital gets deployed. Before you buy the deal, try to break it. If it survives, you may have found something worth pursuing. #RealEstateInvesting #PrivateEquity #Multifamily #CommercialRealEstate #DueDiligence #CapitalRaising #PinnacleOneCapital by @jessedilillo
0
4 months ago
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