Does pre-LOI dilgience help or hurt my chances?

searcher profile

October 28, 2025

by a searcher from The University of Chicago - Booth School of Business in Santa Cruz, CA, USA

I keep losing bids to what I assume are less educated offers I have a pretty efficient approach - I spend a few days to identify any major risks, make a structure that mitigates those, and ensure I can secure debt. I have strong confidence I can close and try to convey that. The risks I find are quite obvious and material to anyone that has any depth in the industry. But... I keep on losing to higher bids. (I am something like 0 for 10) It is clear to me that other buyers are not as deep as me and are going to discover issues post LOI. I am not sure if this is an intentional strategy (to re-trade) or accidental (ignorance / exuberance) Note I am mostly at the low end (500-800K) these days and stay our of overheated verticals. I am bidding at the high end of what a leveraged SBA buyer can afford. I am not using outside equity but I doubt these deals are using. I am genuinely of the belief that it is better for all parties to discover and deal with issues pre LOI, but it seems like whether true or not, the market doesn't reward that behavior. Should I stick to my guns or is my conservatism just shooting myself in the foot? For brokers - do you value diligence pre-LOI, and how can buyers convey the benefits of that versus less prepared buyers? EDIT: thanks all for the input! It's always good to hear that others are in the same boat. I hope all the new buyers coming into the market get quickly informed on affordability and we can get a little more rational. Best of luck all!
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commentor profile
Reply by a lender
from Cornell University in Los Angeles, CA, USA
Hi Joshua nice to meet you. Pre-LOI diligence helps you build confidence with lenders but can make you less competitive when sellers prioritize price and speed. Most brokers and sellers value momentum and certainty of close more than analytical depth. You don’t need to drop diligence entirely. Keep your pre-LOI work focused on confirming SBA eligibility (if that's what you're aiming for), major risks, and financing readiness. Then, in your LOI pitch, highlight that financing is pre-qualified and you can move quickly. That signals confidence instead of caution. The LOI is not binding, and it can always be modified to suit the parameters of what's needed to get the deal done. We have a lot experience financing various companies via the SBA. If you ever need help talking through a deal or crafting the LOI - I am happy to help. We work with all the major SBA lenders. The bank pays us after your loan closes, so this is a 100% free service for you. You can email me directly at redacted or schedule a meeting with me: https://cal.com/francodeguzman/30min. Look forward to chatting!
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Reply by an investor
from McGill University in San Diego, CA, USA
Totally get the frustration. Doing real pre-LOI work can feel like it isn’t rewarded when higher, thinner offers win the day. A couple things I’m curious about (and might potentially help you diagnose why you’re 0-for-10): How are you submitting your LOIs: by email, by phone, in person? Do you walk the seller/broker through your offer live? Are your LOIs customized to the seller priorities: wondering how often you are capturing and reflecting any non-price must-haves (keeping insurance? company car? an office?) What steps do you take to show the seller/broker you can close a deal? Are the LOIs in industries you have plenty of experience in? Do you know who you’re losing to: industry operators, financial buyers with equity, or other SBA searchers? Are you getting any concrete feedback (pre- and post-decision) from brokers/sellers on why the other offer won? DM me if you want to chat about this in greater detail. Maybe I can help.
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