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Upcoming Event Chicago ETA Happy Hour Thursday, July 16 · 4:30 – 8:00 PM CST at Randolph Tavern, 188 W. Randolph Street, Chicago, IL 60601. Pioneer Capital Advisory is co-hosting alongside Grant Hensel (Entrepreneurial Capital) and Alex Hinch (Rejigg) - an ETA investor, an acquisition-financing team, and an ETA deal marketplace in one room. Andrew Hoffman of the Search Fund Coalition will be joining as well, along with Lisa Forrest and Sarah Andrews of Live Oak Bank, who are generously sponsoring the drinks. Appetizers are on us. Whether you are just exploring, full-time searching, or already under LOI, come meet the team and other serious buyers. Preferred vs. Common Equity 101Every few weeks I go back through my call notes and look for the question that keeps coming up. Lately two of them travel together, and they show up the moment a buyer decides to raise money from outside the deal. “Should I bring my friends-and-family money in as common equity or preferred equity?” And right behind it, the one that actually scares investors off: “If my investors put money in, do they have to personally guarantee the SBA loan?” Deal in Focus: the $4M Trades Business A buyer acquiring a roughly $4M trades business wanted to raise $300K–$500K from friends and family, hold on to the vast majority of the common equity, and run the business himself. His three questions were the ones I hear every time: does the raise count toward his equity injection, does it help his coverage, and does anyone other than him have to sign a personal guarantee? Watch how the answers play out as we go. So this issue is the 101 on preferred versus common equity: what each one actually is, where it sits in the capital stack, the SBA rule that quietly turns “preferred” into debt, and the one thing that decides who signs a personal guarantee. Start with the capital stackBefore the labels, picture the order of who gets paid in an SBA acquisition. The diagram below reads top to bottom; and three things move together as you go down it. Read it top to bottom and three things move together. Repayment priority is highest at the top and lowest at the bottom. Risk and return run the opposite way. And control sits at the very bottom, with the common equity, the person actually running the business. Common equity is the owner’s seatCommon equity is you, the buyer-operator. In most of the deals we advise on, the searcher owns the vast majority of the common, almost always the controlling stake. It is the residual claim: you get paid only after every lender and every preferred holder is made whole. That is the worst seat in a bad outcome and the best seat in a good one. Common holders run the business and make the decisions. They are first to absorb losses if the business underperforms, and they keep all of the value created once everyone senior is paid off. Highest risk, unlimited upside, full control. Why the buyer almost always holds the vast majorityNote that I said the vast majority, not all of it. Bringing in common-equity investors is perfectly normal, and the buyer rarely ends up owning literally 100%. But the operator almost always keeps the controlling stake, and two forces push in that direction:
Quick Primer: the Step-Up, in 60 Seconds
The step-up is a pricing tool for outside equity. It awards investors a percentage of the common that is a multiple of the percentage of the deal their cash funded, their compensation for backing an unproven operator and for riding the leverage in the deal.
The formula is simple: Step-up = investor’s % of common equity ÷ investor’s % of the total cash funded
Run it backward to size a raise: investor’s % of the cash × the step-up multiple = the common they receive. A 1.0x step-up is just dollars-for-ownership with no premium; the multiple above 1.0x is the credit investors get for the leverage and the risk.
The trades deal, by the numbers. On the $4M purchase, the equity injection is about $400K - 10% of the deal. Say investors fund the full $400K. At a market 2.0x step-up, they receive 10% × 2.0 = 20% of the common, and the operator keeps the other 80% - despite putting in little or none of the cash himself. That is the searcher being paid in equity for sourcing the deal, securing the financing, signing the personal guarantee, and running the business day to day.
The step-up is not the whole deal. That 20% governs the split of distributions only after investors are made whole on two senior claims: a liquidation preference (typically 1.0x - their capital back first) and a preferred return (market is roughly 8–14%) that accrues before any common is paid. So investors get their money back, then their pref, then their stepped-up share of what is left; the operator’s common sits behind all of it.
Where the multiple lands. Step-ups generally run 1.5x–2.5x, with 2.0x widely treated as the market standard; a 1.5x is often seen as operator-friendly enough to scare off experienced investors. A pricier business, a slower-growth industry, or a more equity-heavy structure pushes the multiple up; a clearly underpriced deal can justify a lower one. Either way, the result is the same shape: investors get a fair risk-adjusted return, and the operator lands on the vast majority of the common while writing a light check. (One naming note: this self-funded step-up is a different concept from the traditional search-fund step-up that rewards search-phase capital).
Preferred equity is debt-like capitalPreferred equity is for the investor who wants a defined return and priority over the owner - but not the keys to the business. It gets paid before common: a preference means the preferred is made whole before common sees a dollar. The return is a set rate (say a 15% coupon) and it is often structured as PIK, which means it accrues instead of paying cash. There is usually little or no voting, so the investor acts much like a lender. The trade is a capped upside for a safer position.
Back to the trades deal. The plan was $300K–$500K of preferred from friends and family at a 15% coupon, PIK, on full standby for the life of the SBA loan, with each investor kept under 20% of the class. PIK matters here: no monthly payment competing with the SBA loan means no cash drag in the early years. In the example, that structure nudged DSCR from roughly 1.45x to roughly 1.55x - while letting the buyer hold on to the vast majority of the common and write a lighter personal check at close. The two side by side: The SBA nuance: when “preferred” is really debtThis is where the 101 gets real - and where I see buyers get tripped up. The SBA does not care what you call it on the term sheet. It cares about whether the money behaves like equity or behaves like debt. Straight from the source: Whether called “search funding” or by some other name, SBA will consider any investment subject to an agreement to repay equity or make distributions to recover an investor’s investment prior to release of the guaranty (e.g., certain types of redeemable preferred stock) to be debt and not equity.
— SBA SOP 50 10 8, Section B, Ch. 1 (Standard 7(a) Loans), p. 137 (eff. June 1, 2025)
In plain terms: if you promise your investors a buyout or repayment before the SBA loan is gone, the SBA treats that money as debt. It will not count toward your equity injection. Flip that around and you get the affirmative rule - the one that tells you how investor equity distributions actually have to work for the money to count. The SOP defines eligible equity this way:
An equity investment not subject to an agreement to repay equity or make distributions to recover an investor’s investment prior to release of the guaranty. — SBA SOP 50 10 8, Section B, Ch. 1 (Standard 7(a) Loans), “Source of Equity Injection,” p. 137 (eff. June 1, 2025) What that means for your raise: your investors can absolutely receive distributions - their preferred return, their return of capital, and their stepped-up share of the upside. What they cannot have is a contractual right to be repaid or redeemed before the SBA loan is paid off. Distributions paid out of real cash flow when the business can afford them are fine; a mandatory redemption or a guaranteed buyout on a fixed date is what flips the investment from equity into debt in the SBA’s eyes - and disqualifies it from counting toward the injection. Standby money can count, but only one flavor of it: Only debt that is on full standby (no payments of principal or interest for the term of the 7(a) loan) may be considered as equity for SBA’s purposes.
— SBA SOP 50 10 8, Section B, Ch. 1 (Standard 7(a) Loans), p. 137 (eff. June 1, 2025)
So: full standby, life of the loan, documented on SBA Form 155, and capped at half of the required injection. The other half has to be your cash. And keep real skin in the deal, on a change of ownership the injection is 10% of the purchase price; full-standby paper can cover up to half of that, and you bring the rest. Banks get uncomfortable when the operator’s own cash drifts toward 5%, so do not engineer yourself down to nothing. The question that scares investors off: personal guaranteesDoes choosing common or preferred change who has to guarantee the loan? Short answer: no. The SBA keys the personal guarantee off ownership percentage of the business, not the label. The rule: any person who owns 20% or more of the business being financed must provide an unlimited full personal guarantee. The threshold is measured at a beneficial ownership level, the bank looks through any LLCs or holding entities in the cap table and asks who ultimately owns the equity underneath. Spouses and minor children have their interests combined. And if no single owner crosses the 20% line, at least one owner still has to step up as guarantor. Every loan needs at least one. What that means when you are raising money
What lenders need, and whenYou do not need every investor’s name on day one. In underwriting, the lender wants the structure: who owns what, how much cash comes from you versus your investors, and the size and basic terms of the raise. The full cap table: with every owner named at every level, is required at closing to pull the SBA loan number, and all owners and guarantors must be U.S. citizens or nationals.
The one thing I will stress: lock the structure before underwriting. Switching from “just the buyer” to “buyer plus investors” mid-stream triggers a change memo and delays the deal. Decide first, then go to the bank.
The 60-second version
Thanks for reading! If you're working on an acquisition, or are in the pre-LOI phases, you can book a short, informal call here to meet our team and learn how we can help you. For pre-LOI buyers ready to explore opportunities: Schedule a meet & greet call Already have a deal under LOI and need financing help: Schedule an LOI consultation Until next time, Matthias Smith President, Pioneer Capital Advisory www.pioneercapitaladvisory.com Disclaimer: The information in this newsletter is for informational purposes only and should not be considered legal or financial advice. Business buyers are encouraged to consult with their legal counsel and accountant to ensure the proper structuring of their transactions and to fully understand the tax implications of seller financing. Thanks for reading. Feel free to reply directly to this email with any questions or thoughts. |
Former SBA lender turned founder of Pioneer Capital Advisory, a seven-figure brokerage guiding entrepreneurs through SBA 7(a) acquisitions. Closed $250M+ in financing in 3.5 years. Practical, data-driven insights for buyers.
Upcoming Events Office Hours Session 2: The Personal Financial Statement Thursday, July 9 at 1:00 PM Central, live on Zoom with open Q&A afterward. I am covering everything in this issue live, so bring your deal questions. Save your seat here Chicago ETA Happy Hour Thursday, July 16, 4:30 to 8:00 PM Central at Randolph Tavern, 188 W Randolph Street, Chicago, IL 60601. Pioneer Capital Advisory is co-hosting alongside Grant Hensel (Entrepreneurial Capital), Alex Hinch (Rejigg), Andrew Hoffman...
We have three events coming up: Office Hours: Thursday, June 25 at 1 PM Central. Join us on Zoom for an informal Q&A. Bring a real deal or a real question. Register here Chicago ETA Happy Hour: Thursday, July 16, 4:30–8:00 PM CST at Randolph Tavern, 188 W. Randolph Street, Chicago. Co-hosting with Grant Hensel (Entrepreneurial Capital), Alex Hinch (Rejigg), Lisa Forrest & Sarah Andrews (Northwest Bank), and Andrew Hohman (Searchfunder Coalition). RSVP here ETA Happy Hour: Thursday, August 20,...
We have two events coming up: Live office hours on June 25 at 1pm: I am kicking off the Pioneer Buy-Side Brief office hours with a discussion on the exact topic in this newsletter. I'll walk through everything in this issue live, work the diagrams in real time, and take your questions as we go. Register here. Chicago happy hour on July 16, 4:30pm to 7pm: Come meet the searcher community in person. RSVP here What a seller note actually does Nearly every SBA acquisition we advise on includes...