How to Sell My Business: 5 Exits Taught Me What Works

Why Most Business Sales Fall Apart

I've sold five SaaS companies. Three deals closed smoothly. Two nearly imploded because I didn't understand what buyers actually cared about versus what I thought they wanted to hear.

Here's what nobody tells you: selling a business is less about your revenue numbers and more about proving the revenue will continue without you. That's the gap where most deals die. The buyer gets cold feet when they realize your business is held together by your personal relationships, your specific expertise, or systems that only exist in your head.

If you're thinking about selling, start by asking yourself one question: could this business run for 90 days if you disappeared tomorrow? If the answer is no, you're not ready to sell. You're ready to start preparing to sell.

The average business sale takes six to eleven months from first contact to wire transfer. That's after you've spent 12-18 months getting your house in order. Most sellers underestimate this timeline by half, which is why they end up accepting lowball offers or watching deals collapse three months into due diligence.

Start Preparing 12-18 Months Before You Want to Sell

The biggest mistake I see is sellers who wake up one morning, decide they're burned out, and want to sell within 90 days. Buyers can smell desperation from a mile away, and desperate sellers get terrible multiples.

The businesses that command premium valuations didn't start preparing to sell last quarter. They were built to be sellable from day one. That means documented processes, a team that doesn't need you for daily decisions, clean financials, and predictable revenue.

If you're serious about selling in the next 12-24 months, here's what you need to focus on right now:

Document everything that lives in your head. Your sales process, your customer onboarding, your vendor relationships, how you handle support tickets, where the passwords are stored. If you're the only person who knows how something works, that's a liability that will crater your valuation.

Reduce customer concentration. If your top three customers represent more than 30% of revenue, you have a problem. Buyers see that as existential risk. If one customer leaves, your revenue drops by 15% overnight. Start diversifying your customer base now, even if it means turning down some large contracts.

Clean up your financials. Stop running personal expenses through the business. Separate your books completely. Get a real accountant who understands accrual accounting and business sales. This isn't the time to DIY your QuickBooks.

Build a management layer. If you're still the lead salesperson, the primary customer contact, and the person who approves every decision, you don't have a business - you have a job. Buyers are purchasing a business, not hiring you. Start delegating aggressively.

I started preparing my fourth company for sale 18 months before I went to market. By the time I talked to buyers, I had three years of audited financials, documented SOPs for every department, a management team that ran daily operations, and zero customer concentration above 8%. We closed at 4.5x SDE in under four months. My third exit, where I started prepping 60 days before listing? That took nine months and closed at 2.8x because buyers found problems during every stage of due diligence.

I learned this the hard way with my first exit. I was so focused on closing deals and growing revenue that I didn't think about what buyers would actually look at. When I finally sat down with serious buyers, they ripped apart six months of financials because I hadn't separated my personal expenses properly. That mistake cost me probably 60 days in the process and definitely hurt my valuation. Start cleaning up your books now, not when a buyer asks for them.

Get Your Financials Bulletproof Before You Talk to Anyone

Buyers will audit everything. I mean everything. Bank statements, tax returns, customer contracts, refund rates, churn numbers, payroll records. If your bookkeeping is a mess, they'll either walk away or slash their offer by 30% to account for discovered risks.

Before you approach a single buyer, get this sorted:

• Three years of clean profit and loss statements
• Balance sheets that actually balance
• All business expenses separated from personal expenses (yes, they'll notice that vacation you wrote off)
• Customer contracts in writing, not just email agreements
• Churn data broken down by month, not averaged across years

I hired a proper accountant for my second exit after nearly losing my first deal over sloppy QuickBooks records. Cost me $3,000. Saved me at least $50,000 in purchase price erosion.

Here's what buyers are specifically looking for in your financials:

Revenue recognition that makes sense. If you're booking annual contracts as revenue in month one, that's going to raise flags. Buyers want to see how you actually recognize revenue and whether it matches standard accounting practices.

Margin consistency. If your gross margins swing wildly from quarter to quarter, buyers assume you don't understand your unit economics. They'll spend weeks digging into cost of goods sold, and every inconsistency will become a negotiation point.

Proof of recurring revenue. If you claim 80% of your revenue is recurring, your financials need to prove it. That means tracking monthly recurring revenue separately from one-time project work, showing renewal rates, and documenting customer lifetime value.

Understand How Buyers Actually Value Your Business

Most sellers obsess over revenue multiples. "I heard SaaS companies sell for 5x revenue!" Sure, if you're growing 100% year-over-year with negative churn and investors knocking down your door.

For the rest of us, here's the reality:

Small businesses (under $1M in revenue) typically sell for 2-4x annual profit, not revenue. Service businesses trend toward the lower end. SaaS and product businesses with predictable recurring revenue trend higher. If your business requires specialized expertise that only you have, expect the multiple to compress.

Buyers calculate what they call Seller's Discretionary Earnings - basically your profit plus your salary plus any personal expenses you ran through the business. That's the number they multiply. If your SDE is $150,000 and they offer 3x, you're looking at $450,000.

The multiple itself depends on:

• Revenue stability (recurring revenue beats project-based)
• Customer concentration (100 customers beats 5 customers)
• Growth trajectory (flat is okay, declining kills deals)
• How dependent the business is on you personally
• How easy it is to operate (documented systems beat tribal knowledge)

I sold one agency for 4.2x SDE because we had documented systems, a team that could operate without me, and 18 months of consistent growth. I sold another for 2.8x because I was still the primary salesperson and lead strategist. Same industry, different multiples, entirely because of operational maturity.

For SaaS businesses specifically, the math shifts once you cross $1M in annual recurring revenue. At that point, buyers start caring more about ARR multiples than SDE multiples. Current market data shows private SaaS companies trading between 3x and 10x ARR depending on growth rate, churn, and profitability. A SaaS business growing 40% year-over-year with strong retention might command 7-8x ARR. One growing 15% with high churn might only get 3-4x.

The Rule of 40 matters more than most founders realize. This metric adds your growth rate to your profit margin. If you're growing 30% and have 15% EBITDA margins, you score 45. Buyers see that as healthy and efficient. If you're growing 20% but losing 10%, you score 10, and buyers assume you're burning cash without a clear path to profitability.

What Is Seller's Discretionary Earnings and Why It Matters

SDE is the single most important number in small business sales, yet most sellers don't know how to calculate it correctly. Get this wrong and you'll either overprice your business (scaring away buyers) or underprice it (leaving money on the table).

Here's the formula: Start with your pre-tax income, then add back your salary, interest expense, depreciation, amortization, and any one-time or discretionary expenses that a new owner wouldn't incur.

Let's say your business shows $200,000 in pre-tax income. You pay yourself a $100,000 salary. You have $30,000 in interest expense from a loan. Depreciation is $40,000. You spent $10,000 on a one-time legal issue and $20,000 on personal expenses run through the business. Your SDE is $400,000.

That's the number buyers care about because it represents the actual cash benefit a new owner-operator would receive from running your business.

Common SDE add-backs that sellers miss:

• Owner health insurance and benefits
• Personal vehicle expenses
• Family members on payroll who don't work full-time
• One-time professional fees (legal, accounting, consulting)
• Non-recurring marketing expenses
• Above-market rent if you own the building

Buyers will scrutinize every add-back. Don't try to add back your kid's soccer expenses or claim your personal gym membership is a business expense. Stick to legitimate costs that a new owner wouldn't incur, and be ready to document everything.

Finding Buyers Who Actually Have Money

You have three main buyer categories, and they behave completely differently:

Individual buyers are usually looking to buy themselves a job. They're using SBA loans or seller financing. They'll scrutinize every detail because they're betting their savings. Expect 70+ questions, multiple calls, and requests to shadow you for a week. These deals take 4-6 months minimum.

SBA loans are popular because they allow buyers to purchase businesses with as little as 10% down. The loan can cover up to $5 million, with terms stretching 10 years for working capital or 25 years if real estate is involved. Buyers using SBA financing will need to show the business can support debt payments, which means your cash flow needs to be at least 1.25x the annual debt service.

Strategic buyers are companies in your industry or adjacent to it. They want your customer list, your team, or your technology. They move faster than individuals but will want non-competes and earnouts. They'll pay more if you have something they can't easily build themselves.

The best strategic buyers are competitors who are one or two tiers larger than you. They see your business as a way to expand into a new market, acquire talent, or eliminate competition. These deals often close at higher multiples because they're buying strategic value, not just cash flow.

Private equity and aggregators are buying portfolios of businesses. They're fast and professional, but they're also ruthless about valuation. If your EBITDA is under $500K, most won't return your email.

I've found buyers through business brokers, direct outreach to strategic acquirers, and marketplace sites like Flippa. Brokers charge 10-15% of the sale price but handle all the screening and paperwork. Worth it for larger deals, overkill if you're selling a $200K business.

For direct outreach to strategic buyers, I built a list of companies that could benefit from acquiring us. If you're selling an agency, that might be larger agencies looking to expand service offerings or geographic reach. If you're selling a SaaS product, look for competitors or companies selling to the same customer base. You can use a B2B lead database to find decision-makers at target companies, or scrape LinkedIn for M&A executives and corporate development teams.

Finding qualified buyers is exactly like finding qualified clients through cold email-you need outbound, not just inbound. I've seen agency owners sit around waiting for someone to magically offer to buy their business, just like they wait for referrals instead of doing outreach. One client I worked with used a targeted cold email campaign to reach 50 private equity firms in their niche, got 12 responses, and had 3 serious conversations within two weeks. You can use your lack of traditional connections as an advantage if you're willing to be direct and personalized in your outreach.

How Business Brokers Work and What They Cost

Hiring a broker is one of the biggest decisions in the sales process. Good brokers earn their commission. Bad ones waste six months of your life and deliver zero qualified buyers.

Broker commission rates vary by deal size. For businesses under $1 million, expect 10% of the sale price. Some charge up to 12% for smaller deals. For businesses between $1M and $5M, most brokers use a sliding scale called the Double Lehman formula: 10% on the first million, 8% on the second, 6% on the third, 4% on the fourth, and 2% on everything above that.

For a $3 million sale, that's $100K + $80K + $60K = $240K in broker fees. Worth it if they bring qualified buyers and handle negotiations. Highway robbery if they list your business on a website and disappear.

Good brokers do the following:

• Create a detailed CIM (confidential information memorandum) that makes your business look professional
• Pre-qualify buyers so you're not wasting time with tire-kickers
• Run a competitive process with multiple buyers to drive up the price
• Handle all the paperwork and keep the deal moving through due diligence
• Negotiate on your behalf without getting emotional

Red flags that you're dealing with a bad broker: They want a large upfront retainer before the business sells. They can't name three similar businesses they've sold in the last 12 months. They promise valuations that are 30% higher than market comps. They don't have a clear marketing plan beyond listing on BizBuySell.

I've used brokers for two of my five exits. Both times, they justified their commission by bringing multiple buyers to the table and running a competitive process that increased the final price by more than their fee. But I've also talked to sellers who paid $50K in retainers to brokers who delivered nothing. Do your homework.

The Letter of Intent: Where Deals Get Real

Once a buyer is serious, they'll present a letter of intent. This is where things shift from casual conversation to legal commitment.

An LOI is mostly non-binding, but certain provisions - like confidentiality and exclusivity - are legally enforceable. The document outlines the proposed purchase price, deal structure, key terms, and timeline for due diligence.

Here's what should be in every LOI:

Purchase price and structure. Is it all cash at closing? Part earnout? Seller financing? The LOI should spell out exactly how you're getting paid.

Included and excluded assets. What's part of the sale? Customer contracts, equipment, intellectual property, inventory? What are you keeping? Cash in the bank, personal vehicles, real estate?

Due diligence period. Typically 30-60 days. This is when the buyer verifies everything you've told them. Be realistic about the timeline - rushing due diligence leads to surprises that kill deals.

Exclusivity clause. The buyer wants assurance you won't shop the deal to other buyers during due diligence. This is binding. Once you sign, you can't talk to other buyers for the specified period, usually 60-90 days.

Contingencies. What needs to happen for the deal to close? Buyer financing approval? Key customer renewals? Transfer of licenses or permits? List everything that could derail the deal.

Transition period. How long will you stay on to train the new owner? 30 days? 90 days? What are you responsible for during that time?

The LOI sets the framework for everything that follows. Once you sign, you're locked into that buyer for the exclusivity period, and renegotiating terms gets harder with every passing week. This is why you need a lawyer to review the LOI before you sign. I've seen sellers agree to terms in the LOI that came back to haunt them during closing - vague earnout provisions, unrealistic contingencies, transition requirements that kept them working full-time for six months post-sale.

Take the LOI seriously. Negotiate the terms you care about. If the purchase price is contingent on hitting revenue targets you know are unrealistic, say so now. If the transition period is longer than you're willing to commit, push back. The buyer expects negotiation. Don't just sign because you're excited someone wants to buy your business.

Due Diligence is Where Deals Die

Once you have a letter of intent, you enter due diligence. This is where the buyer verifies every claim you made. It typically lasts 30-60 days and feels like a proctology exam performed by a team of accountants and lawyers.

They'll request:

• Three years of tax returns
• All customer contracts and renewal rates
• Employee agreements and org charts
• Marketing analytics and traffic sources
• Product roadmap and technical documentation
• Any outstanding legal issues, disputes, or liabilities

The biggest mistakes I see sellers make during due diligence:

Hiding problems. If there's a major customer threatening to churn or a key employee planning to leave, disclose it upfront. Buyers will find out anyway, and discovering it late kills trust and tanks deals.

Being slow to respond. Every delayed answer makes buyers nervous. Set up a shared folder with all documents organized before due diligence starts. When they ask for something, send it within 24 hours.

Getting defensive. Buyers will question everything. It's not personal. Answer clinically, provide evidence, and move on. The moment you get emotional, they assume you're hiding something.

In my third exit, the buyer found a bookkeeping error that overstated revenue by $8,000 for one quarter. I immediately sent the corrected financials, explained what happened, and offered to adjust the purchase price proportionally. They appreciated the transparency and we closed two weeks later.

Due diligence is also when buyers start finding reasons to renegotiate. A key customer didn't renew. Churn was higher than you disclosed. Your largest vendor just raised prices. Expect the buyer to use anything they find as leverage to lower the price or add earnout provisions. This is why clean financials and honest disclosure matter - the fewer surprises during due diligence, the less room buyers have to renegotiate.

Due diligence dies when you haven't been honest with yourself about your business first. For the complete picture, watch this:

The biggest lesson from closing deals faster applies directly to selling your business: give buyers a reason to move now. When someone says "let's revisit this in Q3," I tell them "it takes 60 days minimum for due diligence and transition, so if you want to close by Q3, we need an LOI this month." Create urgency based on their timeline, not yours.

Deal Structure Matters More Than Purchase Price

A $500,000 offer isn't always better than a $400,000 offer. Deal structure determines how much you actually take home and how much risk you're carrying.

All-cash at closing is the cleanest. You get paid, you walk away, you're done. Buyers with this kind of liquidity are rare for smaller deals.

Seller financing means you're lending the buyer part of the purchase price. They pay you over 2-5 years with interest. You're basically the bank. If the business fails after they take over, you stop getting paid. I've done this once for 30% of the purchase price. It closed a deal that wouldn't have happened otherwise, but I wouldn't do it again unless I was desperate.

Earnouts tie part of your payment to future performance. "We'll pay you $300,000 now and another $200,000 if the business hits $X revenue next year." Sounds fair, but here's the problem: the buyer now controls the business. They can underinvest, change pricing, or shift strategy in ways that hurt short-term revenue. You have no control but all the risk. I've turned down deals with earnouts above 20% of the total price.

Equity rollovers are common with PE buyers. They pay you partly in cash and partly in equity in the new combined entity. You're betting on their ability to grow and eventually sell the portfolio. Can be lucrative if they know what they're doing. Can also leave you holding worthless shares if they don't.

My rule: I want at least 70% cash at closing. The rest can be structured however they want, but I'm not betting my entire outcome on their ability to run my business better than I did.

Negotiating Without Leaving Money on the Table

Most sellers either cave immediately or dig in on every detail and blow up deals over nothing. Neither works.

Here's how I approach it:

Know your walk-away number before you start talking. What's the minimum you'll accept to actually sell? If you're not sure, you're not ready to negotiate.

Ask for 20-30% more than you expect to get. Buyers expect to negotiate down. If you anchor at your real number, you'll end up below it.

Give on small things, hold firm on big things. They want you to stay on for six months instead of three? Fine, if the price is right. They want to restructure the deal with a big earnout? That's a dealbreaker unless they're adding significant cash up front.

When a buyer makes an offer, never say yes immediately even if it's great. Ask for 48 hours to review. Buyers who think you're considering other options will sharpen their offer. Buyers who think you're desperate will lower it.

I've found that having a strong discovery process when vetting buyers early on saves time and helps you negotiate from a position of strength. You want to know what they're actually looking for before you start talking numbers.

The other negotiation lever most sellers ignore: competitive tension. If you have multiple buyers interested, you have leverage. If you're negotiating with one buyer in isolation, they control the process. This is why brokers who run competitive processes often justify their commission - they create artificial scarcity that drives up prices.

Here's what I wish someone had told me: you're going to be criticized during negotiations, and you can't take it personally. When I was doing cold email, someone once told me I'd sent the worst email they'd ever read. They still booked a call, lectured me about it, and then bought. In an exit negotiation, buyers will tear apart your business model, your customer concentration, your growth rate-that's their job. The only thing you can trust is that if you keep calm, respond to feedback like a scientist, and believe in your business's value, you'll get to the finish line.

Closing the Deal: The Final 30 Days

You've negotiated the LOI, survived due diligence, and agreed on final terms. Now comes closing - the last 30 days where everything can still fall apart.

During this phase, lawyers are drafting the purchase agreement, the buyer is finalizing financing, and you're transferring licenses, permits, and contracts. Expect at least a dozen documents to review and sign: asset purchase agreement, bill of sale, non-compete agreement, transition services agreement, lease assignments, vendor notifications.

Common closing killers:

Financing falls through. The buyer's SBA loan gets denied, or their investor backs out. This is why you want proof of funds or financing approval before you invest months in a deal.

Key customer doesn't consent to assignment. Some contracts require customer approval before they can be transferred. If your largest customer says no, the deal value drops and the buyer renegotiates or walks.

Seller gets cold feet. I've seen this more than you'd expect. The seller realizes they're actually selling their business and panics. They start finding reasons the buyer isn't qualified or the terms aren't fair. Don't waste six months of your life if you're not actually ready to sell.

On closing day, assuming everything goes smoothly, you'll sign a stack of documents, the buyer's attorney will wire funds to escrow, and your attorney will confirm receipt. That's when you officially stop being a business owner.

The feeling is strange. Relief mixed with loss. Even if you were burned out, even if you wanted to sell, there's a moment of "what the hell did I just do?" I felt it after every exit. Give yourself a few days to process before you jump into the next thing.

The Transition Period: Don't Screw This Up

Most deals include a transition period where you train the new owner. This typically lasts 30-90 days. How you handle this determines whether you get your final payment and preserve your reputation.

Be available but not hovering. Answer questions thoroughly, introduce them to key customers and vendors, document anything that's not already written down. But don't second-guess their decisions or undermine their authority with employees.

I've seen sellers sabotage their own transitions by constantly telling the new owner how they're doing it wrong. Even if you're right, it's not your business anymore. Give advice when asked, otherwise stay out of the way.

The other extreme is disappearing completely. If you agreed to 60 days of transition support and you stop returning emails after two weeks, you're breaching the agreement. They can withhold earnout payments or even sue you.

Set clear expectations upfront: how many hours per week you'll be available, what communication channels to use, and what you're responsible for versus what they need to figure out themselves.

Exit Planning: Legal and Tax Considerations

The structure of your sale has massive tax implications. An asset sale versus a stock sale can swing your tax bill by six figures. This is where you absolutely need professional help.

In an asset sale, the buyer purchases specific assets of the business - equipment, contracts, intellectual property, customer lists. You retain the legal entity and any liabilities not explicitly assumed by the buyer. Most buyers prefer asset sales because they can pick what they want and leave behind liabilities they don't.

For sellers, asset sales typically result in higher taxes because some assets may be taxed as ordinary income rather than capital gains. Consult a CPA who specializes in business sales before you agree to deal structure.

In a stock sale, the buyer purchases the entity itself - all assets and liabilities transfer automatically. Sellers prefer this because the entire gain is usually taxed as capital gains, which is significantly lower than ordinary income rates.

Beyond the sale structure, you need to consider:

Capital gains tax. If you've owned the business for more than a year, you'll pay long-term capital gains tax on the profit from the sale. Depending on your income and state, that's 15-23.8% federal plus state taxes. Some states like California add another 13%. Plan accordingly.

Depreciation recapture. If you've been depreciating assets, you'll owe recapture tax on the difference between the depreciated value and the sale price of those assets.

Installment sales. If you're doing seller financing, you may be able to spread the gain over multiple years through an installment sale, which can reduce your tax liability.

Don't wait until closing to think about taxes. I've met sellers who were shocked to learn they owed $200,000 more in taxes than they expected because they structured the deal wrong. Hire a CPA early in the process.

Should You Use a Business Broker or Sell Yourself?

This depends entirely on the size of your deal and your experience selling businesses.

For businesses under $500K, you can probably sell yourself through marketplaces like Flippa or by reaching out directly to strategic buyers. The broker commission (typically 10% or $50K minimum) might not be worth it.

For businesses between $500K and $5M, a broker often makes sense. They'll pre-qualify buyers, run a competitive process, handle due diligence, and negotiate on your behalf. Good brokers pay for themselves by driving up the final price and preventing deals from falling apart.

For businesses over $5M, you want an M&A advisor, not a main-street broker. M&A advisors work on larger deals, have relationships with PE firms and strategic buyers, and charge upfront retainers plus success fees.

I've sold businesses both ways. When I sold directly, I saved the commission but spent 20+ hours per week managing buyers, answering questions, and pushing the deal forward. When I used a broker, I spent maybe 5 hours per week and the broker handled everything else. The broker also brought three competing buyers, which drove the price up by more than his commission.

If you're going to hire a broker, interview at least three. Ask for references from sellers whose businesses were similar in size and industry to yours. Ask how many deals they've closed in the last 12 months. Ask about their marketing process and how they find buyers. And get everything in writing - commission structure, exclusivity terms, what happens if you cancel the listing.

How to Maintain Business Performance While Selling

One of the hardest parts of selling a business is keeping it running at full speed while you're distracted by the sale process. Revenue drops or customer churn during the 6-month sale process will kill your valuation and give buyers ammunition to renegotiate.

Here's what worked for me:

Don't tell your team you're selling until the deal is nearly done. I know this feels dishonest, but telling employees early creates uncertainty that hurts performance. Key people start looking for other jobs. Productivity drops. Rumors spread to customers.

I typically told my leadership team once I had a signed LOI and was entering due diligence. For everyone else, I waited until two weeks before closing. Yes, some people were upset I didn't tell them sooner. But the alternative - watching revenue drop for six months while people panicked - is worse.

Keep signing new customers. Buyers watch your sales pipeline closely during due diligence. If you stop signing new business because you're checked out, they'll assume the business is declining and renegotiate the price downward.

Don't let key customer relationships slip. If your biggest customer has a problem during due diligence and you're too busy to address it, they might churn. That single event can tank your deal or cost you $100K in purchase price.

Block time for the sale process. Treat due diligence like a part-time job. Block 10-15 hours per week to respond to buyer requests, talk to attorneys, and review documents. Don't let it consume your entire schedule or your business will suffer.

Common Mistakes That Cost Sellers Six Figures

After watching dozens of deals as a buyer, seller, and advisor, here are the mistakes that hurt the most:

Starting the sales process when you're desperate. If you need to sell in the next 90 days because you're burned out or the business is declining, buyers will smell it and lowball you. Start preparing to sell 12-18 months before you actually want to close.

Overvaluing your business based on best-case scenarios. Your business is worth what someone will actually pay for it, not what you think it should be worth. Get a real valuation from a broker or M&A advisor before you set expectations.

Talking to only one buyer. If you don't have leverage, you don't have a negotiation. Talk to at least 3-5 serious buyers simultaneously. The best way to get a good offer is to have a better offer to compare it to.

Letting your business slip during the sales process. It takes 4-6 months to close a deal. If your revenue drops or your team falls apart during that time, the buyer will renegotiate or walk. Keep running the business like you're not selling until the wire hits your account.

Skipping legal counsel to save money. A good M&A attorney costs $10,000-$25,000 for a small deal. A bad purchase agreement can cost you hundreds of thousands in taxes, liabilities, or failed earnout payments. This is not where you cut corners.

Not understanding the tax implications. The difference between an asset sale and a stock sale can swing your tax bill by 20% of the purchase price. Talk to a CPA who specializes in business sales before you agree to deal structure.

Accepting earnouts over 25% of the purchase price. Earnouts sound fair but they're risky. Once the buyer takes over, they control everything. They can change strategy, underinvest in marketing, or fire key employees - all of which hurt your earnout. Keep earnouts under 25% or walk away.

The biggest mistake I see sellers make is the same one that keeps agencies stuck at $20 million when they could be at $60 million-they rely on inbound and hope instead of outbound and control. If you're only talking to the one buyer your broker brought you, you have zero negotiating leverage. But if you've personally reached out to 30 qualified buyers and have multiple term sheets, suddenly that purchase price multiplier goes up. I've watched this play out dozens of times: the seller who does their own outreach in addition to using a broker walks away with 20-30% more money.

What Happens After You Sell

The wire hits your account. The business is no longer yours. Now what?

Most sellers vastly underestimate the emotional impact of exiting. Even if you were burned out, even if you wanted to sell, there's a strange emptiness that follows. Your identity was tied to being a business owner. Your daily routine revolved around that business. Suddenly both are gone.

Give yourself time to decompress. Don't make any major decisions for at least 30 days. Don't start a new business, don't make big investments, don't buy a boat. Just sit with the discomfort for a few weeks.

Some sellers jump immediately into their next venture because they can't stand the void. I did that after my second exit and burned out within six months. After my fourth exit, I took three months off. Traveled, read books, spent time with family. When I was ready to start the next thing, I had clarity and energy.

Financially, you need a plan for the proceeds. Unless you're experienced managing large amounts of capital, hire a financial advisor who works with business owners who've exited. They'll help you structure things to minimize taxes and avoid stupid mistakes like dumping everything into a single investment or lending money to friends who have "great business ideas."

The non-compete you signed will limit what you can do for the next 1-3 years. Read it carefully. If you signed a 2-year non-compete in your industry, you can't start another business in that space without risking a lawsuit. Some sellers use this time to consult, invest in other businesses, or pivot to adjacent industries.

What I Wish I'd Known Before My First Exit

My first sale took eight months and nearly killed me. I was still the lead salesperson, so I had to keep closing deals while negotiating with buyers, going through due diligence, and managing a team that didn't know the business was being sold.

Here's what I'd do differently:

Build the business to sell from day one, even if you never plan to sell. That means documented processes, a team that can operate without you, and clean financials. If you do this, selling becomes easy. If you don't, selling becomes a 12-month project to unfuck everything before you can even talk to buyers.

Tell your team earlier. I waited until the deal was almost done, and two key employees felt blindsided. They stayed through the transition, but the trust was damaged. If you have people who are critical to the business, bring them into the conversation earlier and consider retention bonuses tied to the sale.

Take the first good offer more seriously. I turned down an offer that was 15% below my target because I thought I could do better. The next offer was 25% lower. Markets change, buyers disappear, and timing matters. If you get an offer that hits your walk-away number from a qualified buyer, take it seriously even if you think you can get more.

And finally: the moment the wire hits your account, take two weeks off before you start your next thing. I jumped into a new business three days after my second exit and burned out within six months. Selling a business is emotionally exhausting even when it goes well. Give yourself time to process it before you chase the next thing.

If you want hands-on help preparing your business for sale or navigating the actual process, I work through this stuff in detail inside Galadon Gold. But whether you work with me or figure it out yourself, start earlier than you think you need to. The businesses that sell for the best multiples didn't get ready to sell in 90 days - they were built to be sellable from the beginning.