Frequently Asked Questions

This question is worth considering every year to ensure an optimal sale, and three sets of factors are at play: personal factors are all about you and your journey; business factors are primarily about business readiness; and macroeconomic factors are all beyond your control but should not be beyond your attention.

The personal factors come first. We start with what do you want to do after closing? Most business owners are Type A personalities, and we don't “retire” well. Make sure that you have a “Why” to focus your energy…it will keep you out of trouble. “Why” could also be to de-risk your personal situation, which is perfectly reasonable. The other personal factor is what is your number? If you've found your “Why” then you can create a budget to accommodate it and, working backwards and considering your other assets and income streams, figure out how much you need to take away from a sale after taxes.

Business factors come next: is your company actually ready to sell, with clean books, assignable contracts, and a team that doesn't depend on you being in the room every day? When you are the chief cook and bottle washer, your company is much harder to sell.

The macroeconomic piece may be beyond your control, but recognizing and understanding macroeconomic trends can pay off in a big way. Buyers finance most acquisitions with debt. When interest rates are low, they can pay more and still hit their return targets. When rates climb, their cost of capital rises and offers get more conservative. We saw the same pattern compress multiples in past tightening cycles, in 2000 to 2001 and again in 2007 to 2009, so it's worth knowing where we sit in that cycle before you set your expectations. As I write this, both the US National Debt and the 30-year Treasury bond rate have hit historic highs, a sure sign that buyers will expect higher rates of return in the future, forcing lower valuations. But uncertainty is a double-edged sword, and there are times when foreign investors flock to the US to decrease their risk, increasing demand for US companies.

No aspect of this discussion overrides your business fundamentals. Recurring revenue, a diversified client base, and a business that runs without you are what actually drive your multiple. Macro conditions mainly tell you whether now is a good moment to cash in the multiple you've already built, not whether you've built one.

My best and most honest answer: don't wait until you're ready to sell before you start preparing. Owners who get the best outcomes start eliminating friction, cleaning up contracts, standardizing their books, building out a second layer of management, etc. two to three years before they expect to go to market. That's true whether the market favors sellers or buyers on the day you finally list.

Most buyers of an IT company don't write a check for the whole purchase price. They finance 60% to 90% of what they pay with debt, a pattern Paul Daigle at BizAdvisoryBoard and I have tracked across the deals we see come through. That debt carries a cost, and that cost rises and falls with interest rates.

The math buyers run is simple, even when the paperwork isn't: the cash flow your business throws off has to cover debt service and still leave enough profit to justify the risk. Raise the interest rate on that debt and something has to give, and usually it's the price. When rates are low, buyers can borrow cheaply, bid aggressively, and still hit their return targets. When rates climb, their cost of capital climbs with them, and both banks and buyers get more conservative.

As I write this (early September 2026), the effective federal funds rate sits at 3.63%, well off the highs of 2023 and 2024, and the prime rate is 6.75%. Buyers financing a deal through an SBA 7(a) loan, the route most individual buyers and searchers use to acquire a smaller IT company, are paying somewhere around 10% to 13% APR depending on loan size. Lenders have gotten more competitive again too: some are raising how much leverage they'll extend and loosening covenants to win deals. All of that points the same direction: easier credit than the market saw a couple of years ago, which tends to support higher multiples. [September 19, 2026 note: The pendulum is starting to reverse directions with the recent Federal Reserve rate hike.]

None of this happens in a vacuum, and the rate cycle is only one input. Recurring revenue, a diversified client base, and a business that doesn't depend on you being in the room every day still do most of the work in setting your multiple. The rate environment mainly determines how much a buyer can afford to pay for the multiple you've already earned.

My honest takeaway: you don't control the rate cycle, and trying to forecast it is a game nobody actually wins…ask ten economists where rates are headed next year and you'll get eleven answers. What you can control is being ready to sell when the cycle turns in your favor, so a rate move works for you instead of catching you flat-footed.

Source: Current rate figures: Federal Reserve H.15 Selected Interest Rates release (effective federal funds rate and prime rate, Sept. 9, 2026, federalreserve.gov/releases/h15/); Baystreet Lending's September 2026 SBA 7(a) rate report (baystreetlending.com); lender-competitiveness note from Capstone Partners' Q1 2026 Middle Market Leveraged Finance Update (capstonepartners.com). Rate figures will need periodic refreshing as the cycle moves.

The honest answer is: it depends on which company you're asking about, and that answer is more useful than it sounds.

For well-prepared, recurring-revenue MSPs, this is very much a seller's market. Deal volume is up: 466 MSP and MSSP transactions closed in 2025, a 20% increase over 2024, and 2026 deal flow is already tracking ahead of last year. Private equity showed up in 69% of publicly disclosed MSP deals last year, and PE funds raised back in 2021 to 2023 are sitting on dry powder they're under real pressure to deploy before their investment windows close. Add in the easier credit conditions covered above, and buyers competing for good targets are, if anything, getting more aggressive.

But that demand is not evenly distributed. Premium MSPs, the ones with clean recurring revenue, diversified clients, and management that doesn't depend on the founder, are commanding 10x to 14x EBITDA. Sub-$5M operators without that positioning are getting 4x to 5x. Same macro environment, two completely different markets. Which one you're in has far more to do with your business fundamentals than with Fed policy.

There are longer-term forces working the other direction, too: a wave of baby boomer owners hitting retirement age is adding sellers to the market faster than buyers are showing up for them, especially among commoditized, less differentiated companies. That doesn't flip the whole market overnight, but it's one reason I don't expect this seller-friendly window to stay wide open forever. Another is the ever-expanding US debt. This will be a crisis in my lifetime, I just can't say when.

So: seller's market, if you've done the work. Buyer's market, if you haven't. The macro conditions matter, but your own preparation decides which market you're actually competing in.

Source: MSP deal-volume, PE-participation, and EBITDA multiple figures from the 2026 MSP M&A Report (M&A Signal), as summarized by JFS Partners' 2026 MSP M&A analysis. Demographic countervailing-force note draws on the boomer-succession research covered in FAQ-A4. Rate and credit context from FAQ-A2.

“Silver Tsunami” is the name people in my industry use for a simple demographic fact: an enormous number of baby boomer business owners are hitting retirement age at roughly the same time, and most of them are going to need to sell or close within a similar window.

How big the wave is depends on how you count it, and I'd rather give you the range than pretend there's one clean number. A Project Equity study headlined that 2.3 million privately held employer businesses, 44.7% of all such businesses nationally, are owned by boomers preparing to retire. A February 2026 McKinsey Institute for Economic Mobility report suggests that 6 million small and mid-sized businesses face ownership transitions by 2035. They both project the overall value around $5 trillion. Different methodologies, different scopes, but the same shape to the supply/demand curve.

The succession numbers behind that wave are sobering. Fewer than 15% of these businesses get passed to family. Roughly a third of owners over 50 report real difficulty finding a buyer. A meaningful share of the rest, by several accounts, just quietly close down rather than sell, which is about the most value-destroying outcome an owner can have after decades of building something.

The good news for IT and MSP owners specifically: recurring revenue and sticky clients insulate you. Buyers still want defensive, predictable revenue streams, wave or no wave. The businesses most exposed are the “good enough” ones sitting in the middle of the pack: not distinctive enough to be a premium asset, not small enough to be a quick, simple transaction.

What this means for your timing: don't wait until you're the same age, in the same boat, as every other owner in your cohort trying to sell at once. The earlier in this wave you go to market with a genuinely ready business, the fewer competing sellers you face for the same buyer pool. Getting ahead of the wave, rather than riding it in with everyone else, is the whole game.

Source: Project Equity, “2.3 Million Small Businesses Nationwide Owned by Aging Boomers...” (2026 study); McKinsey Institute for Economic Mobility, “Navigating the great small business ownership transition” (Feb. 2026). Estimates vary by methodology and scope — presented here as a range rather than a single figure.

Yes to both, and increasingly so, as buyers, especially private equity and strategic acquirers, get more sophisticated about what they're actually underwriting when they buy an MSP.

Let's start with cybersecurity. Your security posture is a direct proxy for two things Buyers care about, how exposed your clients are to a breach that could trigger churn or liability, and how much they'll need to invest post-close to bring your security stack up to their standard across a broader portfolio. Sophisticated Buyers will look at: your internal security stack and practices, whether you're delivering security services to clients rather than just IT services, your documented incident response history, and your cyber insurance coverage and claims history. Strong security positioning doesn't just avoid a discount, it's increasingly a genuine value driver, since it signals a more mature, defensible business regardless of what's in your financials. If security has been an afterthought in how you talk about your business, that's worth fixing well before a Buyer's due diligence team asks about it first.

AI adoption is the newer version of the same underwriting instinct, again particularly from larger, more sophisticated buyers who are actively evaluating how automation is going to change MSP service delivery over the next several years. They are assessing whether you're using AI effectively in your own delivery model for ticket triage, monitoring, and/or first-line support, not whether you have an “AI strategy” slide in a pitch deck. Buyers can tell the difference quickly. If AI and automation are already compressing your delivery costs, or clearly could with modest investment, that shapes their view of your margin trajectory and your defensibility against undercutting by AI-native competitors.

One honest caveat on AI specifically: this is a newer, faster-moving factor than something like recurring revenue or security posture, so I don't understand how cleanly it's priced yet. It's both a differentiator among otherwise similar businesses right now and an undefined multiple driver without a clean, cited number behind it. That will likely change quickly.

Both are worth doing regardless of a sale, security because it protects your clients and your business, AI because it protects your margin, and both happen to be things a Buyer will notice and reward.

“Optimal” isn't a marketing strategy. I define it as the sale that gets you the outcome you actually want, not just the biggest number on the closing statement.

Your after-tax takehome is still important, obviously. But I've been through this process twice, and I can tell you that chasing the highest payout often doesn't pan out. [If you're curious, ask me about my spectacular first sale failure and the lessons I learned from it.] This is where the personal factor comes back in: if your “why” includes taking care of your employees and your clients as you move to the next phase of your life, and it almost always does, then selling to the right buyer is often more important than the deal's structure.

For a thoughtful take on this from someone who's actually lived it, listen to Episode 6 of my "From Startup to Sale" podcast, where Willis Cantey of Cantey Tech Consulting talks about sellers who focus on money to the exclusion of everything else, and why that often backfires.

The other key aspect of optimal, in my opinion, is risk management. Clearly you will want a sale where the after-tax proceeds (after any holdback risks) fund the life you want next on a timeline and structure you can live with, but a smaller headline price with cleaner terms and less risk often nets you more, both in dollars and in how well you sleep. So “optimal” isn't about whether you're happy signing the closing documents, but whether you're even happier a year later.

Congratulations, sort of, and also, so what. Agentic AI prospecting has my email box flooded with offers to buy, and I'm a one-person shop. What all of these potential buyers have in mind is avoiding the one thing that will create an optimal sale for you: competition.

The buyer who approached you knows exactly what they're doing. They would much rather negotiate with an owner who has no other options, no market comps, and no advisor in the room than against a broker running a real process. That doesn't make them shady. Honestly, it's a good playbook, and one I would use if I were looking to buy, but not if I were looking to sell.

What to do: Get independent representation, even for a single conversation, before you go any further. Someone whose only job is representing you can benchmark this offer against comparable deals, educate you on the advantages and disadvantages of various deal structures, and model the deal in a way that supports effective decision-making.

What not to do: don't discuss numbers or share detailed financials before an NDA is signed, and read it yourself (or get an attorney's opinion) rather than accepting their draft straight up. Especially don't provide financials if you haven't prepared in advance (cleaned up your books) for a possible sale. Never forget that PE firms and entrepreneurship through acquisition (ETA) searchers are specialists with significant finance and negotiating skills; don't let them take advantage of you.

For a first-hand account of exactly this situation, listen to Episode 7 of my "From Startup to Sale" podcast, where Josh Kotler of Canyon Point Technologies talks about fielding a direct approach on his own MSP before eventually selling to CompassMSP, and what he'd want a seller in that spot to know.

If you think you are truly ready to sell your company, one way to protect yourself is to work with a broker who can run a quiet, targeted process. Talking discreetly to a handful of other qualified buyers usually takes a few weeks and tells you quickly whether the direct offer is reasonable or is just banking on you not knowing any better. We make it our business to know who is buying and currently have dozens of buyers in the wings, so we can run this process for you.

Bottom line: a direct approach can turn into a great outcome. It just needs the same discipline, valuation, representation, and competitive tension as any other sale. Skip that and you're negotiating blind against someone who isn't.

Inflation reaches your valuation through two separate channels: what it does to your own bottom line, and what it does to your buyer's cost of capital. They move independently, and buyers underwrite both.

Start with your own P&L. Inflation raises your costs, mainly labor, your biggest expense, plus cloud and vendor costs, and the question is whether you can pass those increases through to clients. As of this writing, CPI is running at 3.4% year over year, moderate by recent standards, but still a real, ongoing pressure on wages and vendor contracts. The real driver of the valuation impact isn't the inflation rate itself, it's your contract structure. MSPs locked into multi-year, fixed-price contracts get squeezed as wage and vendor costs rise underneath a price that can't move, and that squeeze shows up directly in a lower EBITDA and SDE. MSPs with annual price escalators tied to CPI can pass the cost through and protect their margin instead.

Buyers price this difference directly. When your margins compress because you can't pass costs through, buyers adjust their valuation down accordingly, since they're underwriting your future margin, not just your trailing twelve months.

The second channel runs through the wider economy rather than your own numbers. Inflation is a big part of why the Fed moves rates, and rates set your buyer's cost of borrowing (see FAQ-A2 for the full mechanics). If you've modeled this yourself, you may have noticed that the extra annual interest on a given loan amount looks small. That's true, but it's not the main event. First and most important: lenders don't just charge more on the same loan, they size the loan to hit a target debt service coverage ratio, so the same cash flow supports a smaller loan amount when rates rise, not just a bigger payment on the same one. Second, the risk-free rate anchors every buyer's required return, leveraged or not, so as it rises, exit multiples compress market-wide, not just for buyers carrying debt. Third, thin-margin SBA-financed searchers get priced out of qualifying at the margin, which shrinks your buyer pool and the competitive tension that drives up price in an actual sale process.

You can do something about the first channel: a CPI-linked escalator clause is a cheap, high-leverage fix to make well before you go to market, and I go deeper on structuring them in episode 8 of my podcast, “From Startup to Sale” (see FAQ-F2). The second channel, like the rest of the rate cycle, isn't something you control (see FAQ-A2) — the best move is making sure your business is ready to sell whenever the cycle turns in your favor.

Source: your "How Macroeconomic Trends Affect IT Business Valuations" newsletter (CPI escalator vs. fixed-fee mechanics), plus the debt-service-coverage and cost-of-capital mechanics from FAQ-A2. Current CPI figure: U.S. Bureau of Labor Statistics, Consumer Price Index Summary, 12 months ending August 2026 (bls.gov/news.release/cpi.nr0.htm), confirmed current as of Sept. 19, 2026. Restructured per your request to separate the operational (EBITDA/SDE) channel from the macroeconomic (cost-of-capital) channel, and to explain why the borrowing-cost impact is bigger than the raw extra-interest math suggests — it's mainly a debt-capacity and multiple-compression effect, not just a bigger payment on the same loan. Inflation and rate figures will need periodic refreshing. Renumbered from FAQ-F1 to FAQ-A8 as part of the section restructuring (moves into Section A, retitled "Timing & Market Factors," appended after A7); updated the podcast cross-reference from FAQ-G2 to FAQ-F2 to match that FAQ's own renumbering. Added real hyperlinks to "episode 8" (Spotify episode URL) and "From Startup to Sale" (show page URL) in the closing paragraph, per your request on this review pass — same episode and links already established in FAQ-B4/FAQ-F2, reused as-is.

Sophisticated buyers and professional valuations use multiple methods to determine the enterprise value of your company, but Seller's Discretionary Earnings (SDE) multiples and earnings before interest, taxes, depreciation, and amortization (EBITDA) multiples are the two most important. SDE is more commonly used for smaller, owner-operator business, generally under $1M to $2M in revenue, where an individual buyer is the most likely purchaser. As its name implies, SDE looks at how much your company would have earned if it were run “cleanly.” It recognizes that most small operators make tax-efficient decisions, like paying for your extended family's cell phones, and adds back these discretionary expenses to the bottom line.

EBITDA multiples are the metric of choice as you scale. There will still be addbacks, but they tend to be fewer, and the “discretionary” aspect is usually better aligned with business priorities than pushing questionable expenses through the company.

Your add-back schedule matters enormously to both you and the Buyer. Every legitimate dollar added back increases your enterprise value by a factor of your multiple, whereas a sloppy set of add-backs undermines your credibility. These types of not-quite-legitimate uses of company funds can convey the wrong message, specifically that you are not a “mature” company. Understanding the concept of operational maturity level is beyond the scope of this FAQ, but better run companies get better offers. This is why we like to see “clean” books for the three calendar years prior to putting your company on the market.

If you want a quick, free gut-check on where your own numbers stand, Paul Daigle of BizAdvisoryBoard offers an MSP valuation tool — use code “FMSVal24” for the free version. We talked through it on Episode 9 of my "From Startup to Sale" podcast.

SDE and EBITDA aren't interchangeable, and understanding which one is appropriate in your case will help you understand your company's true worth.

Source: EBITDA-bracket benchmarks from your "Selecting the Right Business Broker" guide; SDE vs. EBITDA is a standard M&A valuation convention, not a disputed figure. See FAQ-B5 on add-backs and FAQ-D2 on matching advisor type to deal size. Episode 9 of "From Startup to Sale" (Paul Daigle, BizAdvisoryBoard) and coupon code from Paul Daigle.

The rule of thumb I've quoted for years still roughly holds: mature MSPs trade around 3x to 6x EBITDA in the $1M to $5M revenue range, moving up to roughly 6x to 9–12x as revenue clears $10M. Current data backs that up directionally, though the exact bands shift depending on whose report you're reading and how they've sliced the market. Rather than boil that down to one number, here's how four related domains actually price out right now, table by table. Note that data for companies under $1m is sparse, so that band has been excluded.

IT services, in general

Data source

Under $5M

$5M–$20M

$20M–$50M

$50M+

Aventis Advisors (EV/EBITDA by deal size, 2015–mid-2026, 1,066 IT services deals)

6.7x

7.9x

10.0x

11.3x–12.7x

CT Acquisitions (IT & Managed Services M&A Multiples Report 2026, adj. EBITDA/SDE by revenue)

3.0x–6.0x

6.0x–9.0x

9.0x–13.0x

—

MSPs specifically

Data source

Under $5M

$5M–$20M

$20M–$50M

$50M+

Aventis Advisors / Mergermarket (deal-size EV/EBITDA, via Salt Creek Advisory's 2026 MSP analysis)

5.2x

6.8x

8.9x

9.9x–11.2x

Ada Stra Equity (2026 MSP market snapshot, by revenue)

4x–8x

5x–9x

9x–11x

11x–14x

SaaS / software

Data source

Under $5M

$5M–$20M

$20M–$50M

$50M+

Aventis Advisors (EV/EBITDA by deal size, 2015–2025, 1,325 software deals)

17.2x

12.2x

12.8x

17.4x–26.9x

ClearlyAcquired (2025–2026, by EBITDA size, range across SaaS/B2B/hybrid models)

8.2x–9.0x

10.8x–12.4x

—

—

MSSP / cybersecurity services

Data source

Under $5M

$5M–$20M

$20M–$50M

$50M+

CT Acquisitions (MSSP & Cybersecurity Services M&A Multiples Report 2026, by revenue)

3.0x–7.5x

6.0x–11.0x

9.0x–13.0x

11.0x–16.0x

Aventis Advisors (cybersecurity EV/EBITDA, 2015–2025, 38 deals, not bracketed by the source)

—

—

12.8x (median; range 8.3x–23.1x across all sizes)

—

A few things move you within any of these ranges more than the table alone will tell you. Recurring-revenue businesses consistently price higher than project-heavy ones doing the same total revenue — MSPs with real MRR run 6x to 8x versus 3.5x to 5x for project-heavy shop, and the same 1–2x premium shows up in the general IT services and MSSP data too. Operational maturity level matters too: premium, well-prepared operators in any of these four categories are getting the top of their range or better, while the same size business without that positioning is stuck at the bottom, in the same market, at the same time.

Not every IT subsector prices like the four above, either. Colocation facilities are the clearest outlier: smaller, single-site colocation operators run roughly low-to-mid teens on EV/EBITDA, which is roughly double a typical MSP's multiple, largely because the valuation leans on real estate and secured power capacity rather than cash flow alone. Move up to hyperscale-grade, multi-tenant data center platforms and multiples run dramatically higher still, into the 20s and 30s. That's a different animal entirely from a regional colocation shop, so don't let a headline data-center multiple set your expectations if you're running the latter.

Multiples are a real range, not a single number, and where you land in any of these tables comes down to the same things we keep coming back to on this page: recurring revenue, diversified clients, and a business that runs without you.

Source: my October 2022 marketing letter for the baseline 3x-6x / 6x-9-12x figures. Current-market tables from Aventis Advisors' IT services, software, and cybersecurity valuation-multiples reports; CT Acquisitions' 2026 IT & Managed Services and MSSP & Cybersecurity M&A multiples reports; Salt Creek Advisory's 2026 MSP valuation analysis (citing Mergermarket deal data and Jaken Equities on recurring vs. project revenue); Ada Stra Equity's 2026 MSP market snapshot; ClearlyAcquired's 2025-2026 SaaS/software EBITDA-multiples piece. Multiples move with the market and different firms bracket by revenue, EBITDA, or deal size somewhat differently — treat these as a current, directional snapshot, not a permanent figure.

Buyers apply a “key person discount” when too much of the business's value resides with any one person, but especially the owner. Estimates of the size of that discount vary with severity, but valuation authority Shannon Pratt's widely cited guidance puts a typical key person discount at 10% to 25%. In more severe cases where the owner genuinely is the business, documented discounts have run as high as 20% to 50%, and that's assuming any Buyer is willing to take on the risk.

What actually drives the discount? Operational maturity level. Do client relationships run through you? Are you the only one who can close a deal or fix an escalation? Does institutional knowledge live in your head instead of your ticketing system? None of that shows up on a P&L, but every due diligence team is looking for it.

This is a fixable problem, and it's one of the highest-return projects available to you, but it often requires several years to correct. See FAQ-C3 on the topic.

Source: key-person discount ranges per Shannon Pratt's valuation guidance and severe-case figures as summarized by Website Closers' 2026 owner-dependence analysis. Estimates vary by severity and by appraiser discretion — presented as a range rather than one figure.

Yes, more than almost anything else you can point to, especially when it is buttressed by strong contracts.

Recurring-revenue MSPs are commanding roughly 6x to 8x EBITDA in the current market, versus 3.5x to 5x for project-heavy shops doing comparable total revenue. That's not a rounding difference. On a $1M EBITDA business, it's the difference between a $6M to $8M outcome and a $3.5M to $5M one, for what can otherwise be a very similar-looking company on paper.

Buyers pay for recurring revenue, often referred to as Annual Recurring Revenue (ARR), because

1. It is predictable;

2. Because it's tied to a contract, it tends to survive a change in ownership; and

3. It de-risks the buyer's own financing.

Lenders like it too. Their main lending criteria is payback, and the probability that they will be paid back is much higher with contracted, recurring cash flow.

Keep in mind that the strength of your contracts solidifies the value of ARR. Auto-renewing service contracts with real termination friction (durability) and automatic price hikes (inflation protection) are worth far more than month-to-month arrangements a client can walk away from with 30 days' notice. For an eye-opening discussion of contracts, listen to Episode 8 of my "From Startup to Sale" podcast where we interview Rob Scott and discuss:

• How to collapse the sales and contracting process into one online step

• Why federal and state data privacy laws affect MSPs

• Common mistakes that MSPs make with their agreements

• Why agreements that apply in the general marketplace don't map well to managed services

• How to avoid continuous margin erosion

• Early termination fees vs liquidated damages fees

• Aligning indemnity clauses in your MSA with the provisions of your insurance policy

• Why it's critical to get your contracts right BEFORE you consider a company sale

• HIPAA, PCI, and DSS

• Redirecting liability to your 3rd party providers

• Rob's risk paradigm, a MUST LISTEN for every MSP

If you're not already tracking your recurring-revenue, you may need an accounting overhaul. I have a free project plan for converting to Service Leadership's normalized Solution Provider Chart of Accounts available here.

Source: recurring vs. project revenue multiples from Jaken Equities' 2026 MSP valuation guide; financing mechanics from FAQ-A2.

SDE starts with your business's pre-tax net income and adds back everything that reflects how you personally chose to run the business rather than what the business fundamentally needs to earn revenue.

Standard add-backs: your own salary and the payroll taxes on it; owner perks and personal expenses run through the business (your vehicle, travel that wasn't really business travel, family health insurance beyond what you'd offer any employee); interest expense; depreciation and amortization; genuinely one-time, non-recurring expenses (a lawsuit settlement, a one-off consulting expense, a casualty loss); and any related-party transactions running above or below market rate, such as rent paid to yourself, or family members on payroll at above-market salaries, normalized to what an arm's-length arrangement would actually cost.

What's not legitimate, and what a buyer's advisor will strike immediately: recurring costs dressed up as one-time (that “one-time” software migration you somehow do every year); anything a lender or buyer's accountant can't independently verify against a receipt or an invoice; and double-counting the same add-back in two different places on your schedule. A sloppy add-back schedule doesn't just get corrected during diligence, it damages the buyer's trust in every other number you've given them.

Practical advice: build your add-back schedule as though a skeptical CPA is going to challenge every line, because one will. The businesses that command the best multiples are the ones where diligence confirms the numbers instead of chipping away at them.

One nuance worth flagging: your own salary and benefits get added back whether you're valued on SDE or EBITDA, full stop. What changes is whether a replacement salary gets netted back out. If you're still the one running things day-to-day, a buyer models in a market-rate manager's salary to replace you, which offsets part of that add-back. But if you've already stepped back and have a COO or GM on payroll doing that job, there's no replacement salary left to net out, since the business is already paying for it.

And a second piece of practical advice: well-run businesses command higher multiples. Discipline matters at every size, but the room for aggressive add-backs shrinks as you grow.

In an asset sale, the buyer purchases specific assets and assumes specific liabilities that both sides negotiate and list out. In a stock sale, the buyer purchases the legal entity itself, warts and all, and steps in as owner of the company.

Buyers prefer asset sales, so about 70% of small and middle-market acquisitions are structured that way. The key buyer benefits and disadvantages include:

BUYER ADVANTAGES TO AN ASSET SALE

BUYER DISADVANTAGES

Acquiring only the assets that they want.

Assignability: Every material contract, lease, and license has to be individually assigned to the buyer in an asset sale.

Avoiding historical liabilities, both known and unknown.

IP: If the company owns significant IP, tracking down and solidifying the rights to it can be difficult.

The ability to use Section 179 to immediately depreciate any assets that were purchased, which is significant tax benefit #1.

The ability to deduct amortization from taxes, significant tax benefit #2.

Sellers that own C-corporations generally prefer a stock sale, which gives them the ability to take advantage of the Small Business Stock Exemption (see our FAQ on the topic). The tax benefits and disadvantages of these two methods do not have an identical impact on Buyers and Sellers, so it is critical that the reduced benefits be compared to the advantages to arrive at a win-win middle ground. I.e., financial modeling is required, and our models include this scenario.

In stock sales, though assignability is far less of an issue, unknown liabilities become a much bigger risk. As a result, Buyers usually demand a lower price and more extensive representations, warranties, and indemnification, along with a larger Holdback, to compensate. Stock sales also require an appropriately licensed representative, which may add to transaction costs.

Neither structure is universally better. Which one makes sense for your deal comes down to Buyer/Seller entity types and Buyer/Seller ability to balance tax and liability risks and rewards.

Source: the ~70% asset-sale figure and assignability point from my LinkedIn article "Reducing Transaction Friction." See FAQ-C4 on contract assignability and FAQ-E3 on the C-corp/Small Business Stock Exemption interaction.

A ready-made data room eliminates bottlenecks. Most of what actually kills deal timelines isn't the buyer, it's missing documentation you could have assembled months earlier.

Building and maintaining a due diligence folder isn't complicated, just tedious, which is exactly why so few owners do it in advance. You should include, at a minimum: three years of financials and tax returns, customer and vendor contracts, employee and contractor agreements, license and insurance documentation, IP records, corporate records and governance documents, any major software or service commitments/agreement, a list of all of your subscriptions, your lease or leases, and, if you're expecting a stock sale, your loan documents. If you'd like my more extensive Due Diligence Checklist, just ask.

When you can provide access to due diligence materials on day one, 1) you accelerate any proposed timelines by starting the clock ticking, and 2) you project professionalism, exactly what serious buyers look for. The alternative, assembling documents reactively during due diligence and providing them piecemeal, signals disorganization and gives buyers leverage to chip at price or add conditions.

There are two other things worth doing early: first, think about standardizing your chart of accounts to Service Leadership's Normalized Solution Provider Chart of Accounts (FAQ-C2) — I have a free migration project plan available here; second, confirm that your contracts allow assignment if this will be an asset sale (FAQ-C4).

Treat “transaction readiness” as part of your annual business hygiene, not a scramble after the LOI is signed. See FAQ-C5 on why that timeline matters more than owners expect.

Source: my LinkedIn article "Reducing Transaction Friction: What Every Business Owner Should Do Before Going to Market."

Buyers and their lenders want visibility into how your company creates value, and a homegrown chart of accounts makes that basically impossible to see quickly or trust fully.

A standardized structure, like Service Leadership's Normalized Solution Provider Chart of Accounts, gives you something IT-industry buyers, brokers, and lenders already recognize. Your numbers can be analyzed, compared against industry benchmarks, and translated into an offer without a translation project happening first.

The payoff is direct: when your books are clean and clear, you command stronger offers and shorter diligence cycles, because buyers aren't paying a risk premium for numbers they can't quickly verify.

In practice, the migration looks like this: inventory your current chart of accounts, map every account and lineitem to the standardized structure, decide whether to reclassify historical data or apply the change going forward only, then migrate carefully with a full backup beforehand and a permanent old-to-new crosswalk kept for future audits and tax prep. I've made a project plan with a lot more detail — built around QuickBooks and Autotask, though the underlying process transfers to any setup — available here.

This project takes time to do properly and is most easily accomplished at a fiscal year boundary, which is why it belongs on the years-before-you-sell list, not the month-before list. See FAQ-C5 on timing your preparation overall.

Source: your COA Migration Project Plan and "Reducing Transaction Friction" LinkedIn article, both referencing Service Leadership's normalized solution provider chart of accounts.

Reducing owner dependency isn't one project, it's a body of work. But it comes down to answering one question for every important function in your business: if you disappeared tomorrow, would it still run?

The concrete moves: document your processes instead of carrying them in your head. Build a real management layer with the authority to make decisions, not just people who execute yours. Move client relationships from “you personally” to “the company,” with account managers who have direct relationships of their own. Make sure sales, delivery, and vendor negotiations don't uniquely depend on your personal relationships or expertise.

This isn't a quarter's worth of work. Relinquishing daily operations and moving to a genuinely management-led structure typically takes 24 to 36 months done properly, which is exactly why it belongs on the multi-year preparation timeline (FAQ-C5), not the pre-close checklist.

The payoff is real: this is one of the highest-return projects available to you before a sale. The key-person discount it addresses can run as high as 20% to 50% off your multiple in severe cases (FAQ-B3).

I know letting go feels like losing control. Framed and done correctly, it's the opposite: it's what actually gives you the option to sell on your own timeline, instead of being stuck running the business forever because nobody else can.

Source: "The Great Business Hand-Off" analysis (24-36 month de-risking timeline) and FAQ-B3 on the key-person discount.

It may seem ridiculous to include this as an FAQ, but contract woes are ubiquitous in this industry, and assignability is one of the worst problems to deal with in an asset sale. So read your contract now, while you are still just thinking about selling, because if contract woes are your woes, it will take months to fix.

Many service agreements, especially older MSAs, either prohibit assignment outright, require the other party's written consent before the contract can transfer to a new owner, or ignore assignability completely. In an asset sale, about 70% of small and middle-market deals, that consent requirement can become a literal closing condition for every affected contract (see FAQ-B6).

Assignability is just the most common way a contract turns into a deal problem. When Rob Scott of Monjur and I went deep on this in Episode 8 of my podcast, his central point was that most MSPs are running on a contract template built for the general marketplace, not one written for managed services, and that mismatch is where the other woes hide.

Beyond assignability, the woes I'd check for before you go to market:

• Early termination fees that are actually liquidated damages in disguise, or vice versa — most owners have never checked which one they signed, and a buyer's counsel will.

• Indemnification language that doesn't line up with what your insurance policy actually covers, leaving a gap you'd personally be exposed to.

• No mechanism for redirecting liability back onto your own third-party providers when their outage, not yours, caused the client's problem.

• Silence on HIPAA, PCI, or state data-privacy obligations that apply to your clients' data whether or not your MSA ever mentions them.

• No protection against margin erosion as a client's usage grows without your pricing catching up.

Assignability tends to go wrong in a few predictable ways: a contract silent on assignment, a contract requiring consent from a client who's hard to reach or has had a personnel change since you signed it, or worse, a client who sees the ownership change as a chance to renegotiate or walk entirely. Any one of these can delay, or derail, a closing that was otherwise ready to go.

What to actually do: review every material contract now, not at the letter-of-intent stage. Flag anything missing an assignment clause or requiring consent, and either renegotiate the clause proactively or get ahead of the conversation with key clients well before a deal becomes public knowledge. Structuring as a stock sale sidesteps most of this, but brings its own tradeoffs (again, see FAQ-B6). For a broader gut-check than just assignability, Rob's risk paradigm from that same episode is the closest thing I've found to a real checklist for whether your contract is actually protecting you. [You can also hit the easy button and call Monjur. Please tell them I sent you. And no, I do not get a referral fee.]

Contract woes are a boring thing to worry about, right up until one of them costs you weeks at the closing table, or a price reduction you never saw coming.

Source: LinkedIn article "Reducing Transaction Friction" (the ~70% asset-sale figure and assignability point) and Episode 8 of "From Startup to Sale" (Rob Scott, Monjur — show notes on data-privacy exposure, indemnification/insurance alignment, third-party liability redirection, and margin erosion). See FAQ-B6 on asset vs. stock sales and FAQ-B4, which cites the same episode for its full discussion-topic list.

Three years, as a rule, and I've been saying that consistently since well before it was a fashionable answer.

Why three years specifically: it's roughly the timeline needed to do the work that actually moves your multiple, cleaning up contracts, standardizing your books, and building the management depth that removes key-person risk, all of which I've discussed in other FAQs, and all of which combined can require 24 to 36 months to be done properly. It's also enough time to let a full sales cycle play out before finding the right buyer, running due diligence, and dealing with closing, without you feeling forced to accept a worse deal because you're burned out or in a hurry.

If you need help getting going, start with auditing your contracts (see FAQ-C4), as fixing contract woes can take a lot of time. Then assemble your due diligence folder (FAQ-C1). Now it's time to breathe and think. Have an honest conversation with yourself about your personal "why" and your number (FAQ-A1, FAQ-A6). And ask yourself, if you were buying your business, what would worry you the most. Fix that, too!

None of this requires you to have decided to sell. And all of it will result in a better outcome when the time arrives.

Source: "The Great Business Hand-Off" (24-36 month de-risking window).

Nobody warns you about this part, and it's arguably harder than any of the financial mechanics covered elsewhere on this page.

Most business owners I work with are Type A personalities, and we don't "retire" well. The identity question sneaks up on people who spent decades being "the owner of X" and then, one closing table later, aren't anymore. Although the losses are gradual, losing the daily structure, the sense and responsibilities of being needed, the relationships built around running the business, these are real transformations, not a footnote.

My practical advice: figure out your "Why" before you sign anything, not after. Yes, selling your business closes a door, but it opens up so many others! It could be a next business, a board seat, volunteering for your church or a non-profit, spending more time with family, travel, more golf, whatever. It could also be genuinely nothing planned yet, and that's fine, as long as you've actually thought about it in advance and that's what works for you (more on this in FAQ-A1).

Emotional readiness is critical during the sale process itself, not just after. You are selling "your baby." I've been through this twice, most people would call me logical, but it is nearly impossible to remove the emotions from this process. Don't risk sabotaging yourself because some unconscious part of you just isn't ready to let go.

The three types mostly differ by scale and specialization, not by title. A generalist business broker handles a broad range of businesses, usually under $5M in enterprise value, with a local network of buyers and a standardized sales process. That's a fine fit for a small, straightforward asset sale, but generalists often lack the domain depth that specialists bring to the table, and they certainly don't maintain a list of buyers (I have over 100!) in the space.

A specialized, IT-focused broker like me works exclusively in technology, MSPs, cybersecurity, and similar niches. This is usually the right fit for companies generating $1M to $20M in revenue: we understand recurring revenue models and add value based on both operational experience (we can find and fix the obvious warts that every business has) and our network of strategic buyers, private equity firms, and industry consolidators actively looking for IT acquisitions.

A lower middle market investment banker handles bigger, more complex deals, typically $10M to $200M, sometimes lower for a strategically valuable IT asset. They run competitive, multi-party processes, handle recapitalizations and growth equity placements, and bring a global network of institutional investors and large strategic buyers. Their fees run higher too, often an upfront retainer plus a success fee, reflecting the depth of the work.

So which one do you actually need? There are two parameters that determine that. The first is business type, and I strongly recommend that all companies work with brokers who have experience in their domain. While I am the only broker I know who also ran an IT company, there are other brokers who focus on restaurants, or franchises, or C-stores. The second parameter is deal size, and for that we look at both annual revenue and EBITDA. I think the following heuristic will help:

• EBITDA below $5M: Use a specialist broker in your domain if one exists, otherwise use a Main Street broker.

• EBITDA above $5M: a middle market investment banker becomes increasingly relevant, especially if you have significant IP, rapid growth, or a strategic buyer angle worth running a search process for.

Three quick examples of how this plays out: a local MSP doing $1.5M in revenue, with solid recurring revenue and a strong local reputation, whose owner wants to retire in two to three years, is a good fit for a specialized IT-focus broker who knows MSP multiples and the regional and national consolidators buying them. A SaaS company doing $20+M in ARR with a proprietary, AI-driven platform and global growth ambitions needs an investment banker who can run a competitive search process among venture, private equity, and strategic buyers. A legacy IT consulting firm doing <$500K in revenue, with a loyal but aging client base and not much proprietary technology, can often be served well by a generalist broker, though a specialized broker will still expand the buyer search nationally and better align seller and buyer goals.

None of this is exact science. Your growth trajectory, your intellectual property, and what outcome you actually want (see FAQ-A6 on what "optimal" means) matter as much as raw size. Treat these brackets as a starting point for a conversation with a prospective advisor, not a strict rule.

Source: "Selecting the Right Business Broker: A Strategic Guide for Lower Middle Market IT Companies" — advisor-type definitions, the domain-expertise-plus-EBITDA heuristic, and real-world scenarios A, B, and C (paraphrased here).

Before you sign anything, ever, read the entire agreement. If there is complexity you don't understand, ask your attorney. And, in my humble opinion, run the agreement by your LLM of choice (or two) and ask about the gotchas.

There are a number of key terms to review and understand:

• The exclusivity period: how long you're committed to working only with them;

• The tail period: how long after the engagement ends can the broker still claim a fee if a buyer they introduced eventually closes;

• The scope of services: what exactly they'll do;

• The payment calculations: how is the fee calculated;

• The termination clauses: under what conditions either party can exit; and

• The confidentiality provisions: how your sensitive information gets protected.

Do your due diligence by vetting the broker. Are they licensed? Are they members of reputable associations like the IBBA or M&A Source? Can they show you specific IT deals they've closed, with references you can actually call? What's their average time to close? What is their process, and does that resonate with you? A good broker will welcome this scrutiny.

Source:"Selecting the Right Business Broker" (engagement agreement terms and broker due-diligence checklist).

Yes, plainly.

A broker charging you nothing is being paid by the buyer instead, which means the buyer is their real client, whatever their marketing says. Buyers offer what a business is worth to them. If they're the one paying the brokerage fee, that fee comes straight out of what would otherwise be your offer, so you are in effect paying the fee anyway without receiving any value!

Beyond the incentive problem, no-fee and Main Street brokers usually lack the skills to solve the issues that should be handled before you ever go to market: contract cleanup, chart-of-accounts standardization, owner-dependency reduction, the whole preparation agenda covered elsewhere in these FAQs. Free service is usually free for a reason.

For an optimal sale, bypass no-fee and Main Street brokers entirely. If a broker's fee structure sounds too good to be true...

Source:"Selecting the Right Business Broker" (the "No-Fee Subtype" warning).

Most brokers charge a success fee that is a percentage of the sale price, sometimes alongside an upfront retainer or monthly advisory fee (more common with investment bankers) that gets credited against the eventual success fee.

Yes, a higher fee is often worth it, and the math is straightforward once you focus on net proceeds instead of the headline percentage. A broker charging 10% who sells your company for $6M nets you $5.4M. A broker charging 8% who sells it for $5M nets you $4.6M. The higher-fee, higher-value broker is clearly superior, and choosing solely on the lowest commission is a false economy.

What the fee should actually buy you is a structure that incentivizes the broker to optimize your experience, whether that is maximizing price, minimizing time on market, finding the buyer who will best care for your clients and employees, or something else. Focus your analysis on net proceeds and a demonstrated track record, not the headline percentage. Ask specifically what the fee covers, how any retainer credits against it, and what happens if you terminate before closing. And keep in mind that the cheapest broker on paper is often the most expensive one in practice.

Source:"Selecting the Right Business Broker" (the 10% of $6M vs. 8% of $5M net-proceeds example).

First of all, I am not a banker. You will be better off discussing this question with a real SBA banker, and I'll happily refer you to several of them that I've worked with and trust, just ask.

SBA financing, specifically the 7(a) program, is how most individual buyers and searchers finance the purchase of a smaller IT company. There are two key benefits for buyers: first, the program has a relatively low down payment requirement; second, the loan is insured by the government, increasing the risks that bankers are willing to take in their financing decisions. There are also several key disadvantages: closing costs tend to be higher because the buyer typically pays for that insurance, and there are a whole host of other rules and restrictions that change as the government changes its goals for the program.

The SBA has a separate program for purchasing real estate, called the 504 program. It is possible to participate in both programs, subject of course to various restrictions and limits that are beyond the scope of this FAQ.

The SBA's rate structure, like that of other banks, ties to the federal funds rate with a spread that varies by loan size. Smaller loans carry wider spreads (see FAQ-A2 for the rates as of early September 2026). That puts qualified SBA 7(a) borrowers somewhere around 10% to 13% APR depending on loan size. Because SBA loans are insured, the SBA rate is often less than non-insured loans.

Estimating the true closing cost of SBA loans is complex; the SBA adjusts their fees periodically to meet program goals, so our financial models have to be adjusted with deal-specific and timely data. The fee differs deal to deal, so a rough back-of-envelope estimate is usually wrong, sometimes by a meaningful amount.

For Sellers, there are few implications. How the buyer finances a deal is their prerogative, but note that any time financing is required your financials need to hold up not just to your buyer's satisfaction but to a lender's underwriting standards. That's one more reason clean books and a standardized chart of accounts (FAQ-C2) matter.

If you're a searcher or buyer modeling an SBA-financed acquisition yourself, this project-cost and guarantee-fee modeling is exactly the kind of work I do for clients on the buy side (see FAQ-F3).

Source: my ETA Marketing Bundles document (SBA project cost, guarantee fee mechanics, and the 504 real estate program); current rate figures from FAQ-A2 (Baystreet Lending, Sept. 2026).

An earnout is a piece of your sale price that isn't paid at closing. It's paid later, contingent on the business hitting agreed performance targets, usually revenue-based but occasionally profit-based or even client-retention based, over some period after the sale, typically one to three years.

There are several downsides to earnouts, so I'm generally cautious about recommending them. First and most important: earnouts tie some (or all!) of your payout to performance metrics you rarely have control over. For example, metrics based on profit will be impacted by the new owner's decisions about staffing, pricing, and strategy. Second, earnouts are prohibited in SBA deals, though there are workarounds to that. Third, while financial modeling can show whether the deal's available cash flow supports an earnout; it doesn't guarantee the earnout actually pays out. Thus, if you are going to accept an earnout, try to structure it so that 1) both buyer and seller are aligned in their goals; 2) the metric(s) are not manipulable; and 3) you have the rights to review financial reports on demand.

There are times when an earnout or one of its variants is the only reasonable solution. If your business fails the "desirability test," perhaps you are a break/fix shop with no recurring revenue, you may not have a choice. Or you've learned that your top two clients may be about to disappear. From a Buyer's perspective, earnouts decrease risk. If your choices are lower your price or reduce the risk of the deal, sometimes it's better to reduce risk and hold on to the potential upside that an earnout brings. Another clear case where an earnout makes sense: you have no recurring revenue but plenty of good clients who could be transitioned to that model. You'll make more from an earnout sale by sticking around for a bit and helping the new owner with those transitions. Accepting an earnout can also signal confidence: if you believe your own projections, an earnout is a way to get paid for being right.

An earnout can absolutely be the right tool to close a valuation gap. Just go in with clear eyes about how much of the outcome you're leaving in someone else's hands.

Source: my ETA Marketing Bundles document (deal-modeling framework, including earnout support via available cash flow, the SBA earnout prohibition, and the "desirability test" framework).

If you've set up your business as a C-corporation, it's probably because your accountant or tax advisor has already explained the Small Business Stock Exemption (U.S. Code § 1202) to you, but unlikely that s/he explained the real and complex implications for how your sale gets negotiated. In a nutshell, it lets you exclude some or all of the capital gains tax on the sale of qualifying stock you've held for more than five years, subject to a cap on how much gain you can exclude and eligibility rules tied to your company's size and when the stock was issued. The exact figures have shifted with recent tax legislation, so confirm the current numbers with your own tax advisor before you rely on them.

The upside for you as the seller is real: if your stock qualifies, you can exclude some or all of the capital gain on your sale from federal tax, which is probably why your accountant recommended the C-corp structure in the first place. The catch: that benefit only survives a stock sale, not an asset sale. And a stock sale is worse for your buyer, since it's riskier for them, and it means they get no tax benefit from amortization or depreciation on the assets, benefits that would otherwise be worth real money over the life of the deal.

That creates a genuine negotiating dynamic. We can estimate the net present value of that lost amortization and depreciation benefit to the buyer and use it as a data point in negotiating around the value of the exemption to you. Note that the loss to the buyer rarely equals the gain to you, since tax rates and depreciation schedules differ between the two of you, so this isn't a simple dollar-for-dollar trade.

This is exactly why the asset-sale-versus-stock-sale decision (FAQ-B6) isn't just a legal technicality. It's a real financial negotiation with your buyer, and your C-corp status and 1202 eligibility are a major factor.

Remember that I'm neither lawyer nor CPA, so 1) this isn't legal or tax advice, and 2) if this applies to you, get your tax advisor and your deal advisor in the same room before you negotiate a term sheet, since both sides of this tradeoff need to be modeled together.

Source: my ETA Marketing Bundles document (C-corp / Small Business Stock Exemption modeling), plus 26 U.S.C. § 1202 for the exemption mechanics. Not tax or legal advice.

Three things, really: a defensible forecast, some guidance on the most appropriate deal structure, and a clear answer to whether the deal makes sense.

Let's start with the forecast. Our acquisition models generally use a 10-year, high-quality pro forma covering the P&L, balance sheet, and cash flow. When detailed financials are available, we build the forecast account by account; when they are not, we use percentage-of-sales modeling, which estimates COGS and operating expenses as a historical percentage of revenue. When it is necessary, we use stochastic (probability-based) modeling to make the model more realistic. The pro forma developed here supports the go / no-go purchasing decision; if the decision is to make the purchase, it is delivered to the bank as part of the loan application package. Every aspect of your pro forma should be carefully reviewed, as it needs to be both reasonable, grounded in real experience, and defensible, backed by evidence, in order to get financing.

Regardless of our pro forma modeling technique, be aware that the model is wrong! In fact, all models are wrong. The goal is to make a model that is useful, and that is where deal structure modeling comes into play. Our base model allows you to consider variation in down payment amounts, earnouts, and loan characteristics for both bank loans and Seller-financed loans.

Forecasting and deal structure feed into the decision tab, where logic and finance answer the question "Does this deal make sense?" There are numerous metrics to consider, but three key metrics are the Net Present Value, the Internal Rate of Return, and the Debt Service Coverage ratio. These should be interpreted with your advisors.

Source: my ETA Marketing Bundles document (10-year pro forma, percentage-of-sales vs. account-level modeling, deal-structure modeling, and decision-tab framework, now including named decision metrics: NPV, IRR, and DSCR).

After graduating from the Johns Hopkins University with a minor in computer science, I founded and ran my own IT consulting company for 27 years, from 1986 to 2013, evolving it over that time from software design and development into a managed services model, the same transition a few of my clients are navigating today.

I've been on the other side of the closing table myself, having sold that business twice. The first time was to a roll-up, and it didn't go so well. The second time went better financially, but I wasn't well prepared emotionally. So the advice in these FAQs isn't theoretical, it's lived experience translated into a service for other owners.

Since 2013, I've provided business brokerage and C-level consulting services to IT companies specifically. I'm a licensed Florida business broker (Florida Real Estate Corp. CQ1065684) and hold a recent Master's degree in Finance from the University of Florida. Please connect with me on LinkedIn here to review my other business, volunteer, and educational credentials.

Yes: “From Startup to Sale: A Podcast by MSPs for MSPs,” available on Spotify (or wherever you get your podcasts).

Most episodes feature a rock star from the MSP or IT-services world talking through how they actually built, ran, bought, or sold their own company, or discussing how their product meets your needs. Every episode is listed below, in order, so you can jump straight to the ones that match what you're working through.

Episode

Guest(s) & Company

Key Takeaways

Ep. 1: A Conversation With Peter Kujawa

Peter Kujawa — Service Leadership, Inc.

A free, normalized chart of accounts for IT companies; “Always run your business as if you were going to sell it”; operational maturity levels (OML) and how SLIQ measures them

Ep. 2: A Conversation With David Williams and Tom Raad

David Williams & Tom Raad — Courser

What Courser looks for in an acquisition; how Courser integrates its family of companies; the emotional side of being acquired; the one number to know before you think about exiting

Ep. 3: A Conversation With Christopher Vollmond-Carstens AKA CVC From Ntiva

Christopher “CVC” Vollmond-Carstens — Ntiva

What Ntiva looks for in an acquisition; tips for owners thinking about an exit strategy; being prepared operationally and emotionally; what working capital is and its role in a deal

Ep. 4: A Conversation Stephen Buyze from AG MSP Coaching

Stephen Buyze — Advanced Global MSP Coaching

When to hire a service coordinator or an outsourced NOC; the right tech-team size and structure for early-stage growth; KPIs for service companies; common mistakes MSPs make

Ep. 5: A Conversation Kyle Christensen from K7 and Empath

Kyle Christensen — Empath

The bottleneck to hypergrowth; which KPIs actually matter; risks specific to MSP startups; why to avoid certain marketing spend

Ep. 6: A Conversation with Willis from Cantey Tech

Willis Cantey — Cantey Tech Consulting

Finding the right financial partner for acquisition-driven growth; why your first acquisition is an experiment, not a blueprint; sellers who focus on money to the exclusion of everything else, and why that backfires

Ep. 7: A Conversation with Josh Kotler

Josh Kotler — Canyon Point Technologies

How peer-group membership accelerates organizational change; the pain of transitioning from break-fix to managed services; why smaller MSPs are commanding higher valuations right now

Ep. 8: A Conversation with Rob Scott from Monjur

Rob Scott — Monjur

The biggest mistake MSPs make in their contracts; why federal and state data-privacy law affects MSPs; early termination fees vs. liquidated damages; Rob's risk paradigm — a must-listen for every MSP

Ep. 9: A Conversation with Paul Daigle from BizAdvisoryBoard.com

Paul Daigle — BizAdvisoryBoard

What happens to multiples once you break $100M; why MSPs without cybersecurity will go extinct; how compliance requirements like PCI and HIPAA are driving the industry; the free MSP Business Evaluator tool

Ep. 10: A Conversation with James Allen from Pia.ai

James Allen — Pia.ai

What Pia does and how it works; pricing models; how Pia supports rapid economies of scale during acquisitions; the most common ticket types it automates

Ep. 11: A Conversation with Jeffrey Newton and James Farrow at Cyft.ai

Jeffrey Newton & James Farrow — Cyft.ai

The key problems Cyft solves; its “Speak It, Review It, Submit It” process; how quickly it can be implemented; Cyft as an AI on-ramp for MSPs

Ep. 12: Exit - Stage RIGHT! Optimizing Your Exit

Jeff Greenspan

The five key actions Sellers should take to prepare for a sale, regardless of timing: choosing the right business structure; understanding and communicating how your business creates value; eliminating bad habits that decrease exit valuation; removing impediments to a sale; preparing for due diligence

Ep. 13: Dominating a Mid-size Market

Brian Strong — Ten Hats

Turning around a company that's hemorrhaging cash; Ten Hats' “building block” approach to services; don't micromanage people, micromanage the numbers; why go to peer groups

Ep. 14: A Tight Affiliation of 170 MSPs

Tim Conkle — The 20

How The 20's MSP alliance and rollup model works; the three things MSPs need to do to succeed; how Tim thinks about economies of scale; the benefits of joining an affiliation

S2E1: An International MSP

Ankur Kothari — Olive and Goose

Running an MSP from anywhere; how to create a “beachhead” in a new market; the opportunity AI presents for MSPs helping clients adopt it; his take on rollups for higher EBITDA multiples

S2E2: A Billion Dollar Startup

Seth Helgesen, Zach Watson & Brian Wick — Ionos

Key differentiators vs. AWS, Azure, and Google Cloud; security features built in; how pricing and partner/reseller programs work; support for legacy applications

S2E3: Building an Effective Sales and Marketing Program

Megan Killion — MKC Agency

Why sales needs to be a function of your business, not just outsourced; how to design a scalable sales program; hiring sales talent the right way; how AI will affect your sales process

Each of the five steps in Episode 12 also gets its own short video, which I've published on my YouTube channel (look under Playlists):

1. Creating value by choosing the right business structure

2. Understanding and communicating how your business creates value

3. Eliminating bad habits that decrease exit valuation

4. Removing impediments to a sale

5. Preparing for due diligence

Source: my "From Startup to Sale" Spotify show page (episode titles, air dates, and show notes) and my Podcast Recap workbook (guest/company detail). Guest LinkedIn and company links researched and verified via web search as of September 2026; a few guests have since changed roles or companies since their episode aired.

Yes, but not inside the IT space. My brokerage currently only represents sellers of IT companies, so if you're a searcher or buyer looking specifically at IT targets, I'm on the other side of that table, not yours.

For buyers and searchers outside IT, I offer a separate paid service built around two things: an AI-curated list of off-market acquisition targets, and financial deal-modeling support once you've picked one.

On the sourcing side, I use Apollo.io to select up to 250, or 500, companies and owners matching your search parameters, NAICS codes, geography, revenue range, employee count, and so on, then score them with an AI agent I built that weighs demographic, firmographic, and behavioral signals, things like owner age, company age, and succession signals showing up in someone's LinkedIn or website activity. In practice, somewhere between 5% and 10% of a selected list typically scores above 80 out of 100 on likelihood to engage.

On the modeling side, once you have a target in mind, I help you work through whether a deal is worth pursuing, how to structure it (stock vs. asset, earnout or not, see FAQ-B6 and FAQ-E2), how to finance it including SBA project cost modeling (FAQ-E1), and the tax nuances around things like C-corp status and the Small Business Stock Exemption (FAQ-E3). It all rolls up into a 10-year pro forma and a decision tab that tells you, plainly, whether the deal makes sense (FAQ-E4).

Source: my ETA Marketing Bundles document (AI-curated sourcing and modeling bundles, non-IT restriction, 5-10% likelihood-score figure) and my "Find High-likelihood Clients Using Agentic AI" post.