How Can I Sell My Business? A 5-Exit Founder's Playbook

Why Most Business Sales Fall Apart (And How Mine Didn't)

I've sold five SaaS businesses. Three went smoothly, one took 18 months longer than expected, and one deal died two weeks before closing because the buyer's financing fell through. The difference between successful exits and failed ones isn't luck-it's preparation and knowing what buyers actually want versus what you think they want.

Most founders asking "how can I sell my business" are really asking three different questions: Am I ready? Who would buy this? And how do I not get screwed in the process? I'm going to answer all three based on what actually worked when I sold my companies, not theoretical advice from consultants who've never closed a deal.

The average business sale takes 6-12 months from initial conversations to closing, but I've seen deals drag on for two years or collapse in the final week. The founders who get the best outcomes are the ones who start preparing at least a year in advance, understand their business's actual value in the current market, and have the discipline to walk away from bad deals.

Before You Even Think About Selling: Is Your Business Actually Sellable?

Here's the hard truth: most businesses aren't sellable at the price the owner wants. Not because they're bad businesses, but because they haven't been built with an exit in mind. If your business can't run without you for at least three months, it's not a business-it's a job. Buyers pay for assets that generate cash flow without requiring the founder's daily involvement.

I made this mistake with my first company. I was the only salesperson, the only one who understood the technical architecture, and the only one customers wanted to talk to. When I got an acquisition offer, the buyer's first question was: "What happens to revenue if you leave?" I couldn't answer confidently, and the valuation reflected that risk. I sold for 2.1x ARR when comparable companies in my space were getting 4-5x.

Ask yourself these questions honestly: Can someone else close deals? Can someone else handle customer escalations? Can someone else make product decisions? If the answer to any of these is no, you're not ready to sell at a premium multiple. You need to build systems, document processes, and hire people who can operate independently before you talk to buyers.

The second question is whether your financials tell a clean story. Growth is great, but erratic growth raises red flags. If your revenue was $400K, then $800K, then $600K, then $900K over four years, buyers will discount your valuation because they can't predict future performance. Consistent growth-even if it's slower-commands higher multiples than volatile growth.

Get Your Financials Clean (Six Months Before You Even Talk to Buyers)

The first deal I tried to sell nearly collapsed because my books were a mess. I was running personal expenses through the business, my revenue recognition was inconsistent, and I couldn't clearly explain a $40K expense from two years prior. The buyer's accountant flagged it, and we spent three weeks untangling everything while the deal almost died.

Here's what buyers will scrutinize:

• Revenue documentation: Every invoice, every payment, every refund. If you say you did $500K in revenue, they'll verify every dollar. I use accounting software that integrates with my bank accounts so there's a clear paper trail.
• Profit margins: Separate your personal expenses from business expenses immediately. Buyers won't give you credit for profit you can't prove. Clean financials mean higher multiples.
• Customer retention metrics: They want to see churn rates, lifetime value, and recurring revenue stability. For my SaaS exits, I had to provide cohort analysis showing how customers from different acquisition periods performed over time.
• Contracts and agreements: Client contracts, vendor agreements, employee/contractor paperwork, IP assignments. Everything needs to be documented and filed properly.

If your books aren't clean, hire a fractional CFO or accountant who specializes in preparing companies for sale. It cost me $5K and saved one of my deals. Don't cheap out here.

One specific issue that kills deals: commingled personal and business expenses. I've seen founders lose $100K+ in valuation because they couldn't prove which expenses were truly business-related. Create a separate business credit card, separate bank account, and never run personal expenses through the business. If you've been doing this, spend six months cleaning it up before you list the company.

Tax returns need to match your internal financials. Buyers will pull your tax returns during due diligence, and if the numbers don't reconcile with what you've been showing them, the deal dies or the price drops. I've never seen a buyer overlook significant discrepancies between tax filings and management financials.

Build Systems That Run Without You

Buyers pay more for businesses that don't require the founder to operate. When I sold my third SaaS company, I hadn't personally handled a support ticket in eight months. The business ran on documented processes, and my team knew exactly what to do without asking me.

I documented everything in a central system-sales processes, customer onboarding, support protocols, product roadmap decisions. If you're still the only person who knows how to close deals or solve technical problems, your business isn't sellable at a good multiple. It's a job, not an asset.

This is especially critical if you're running an agency or service business. Buyers want to see that revenue continues without you answering every client email. I cover the exact process documentation framework I use inside my coaching program, but the short version is: record yourself doing tasks, have someone else document the process, then have a third person follow the documentation to test it.

Here's the test I use: Can you take a two-week vacation without checking email and come back to a business that performed as well or better than if you'd been there? If not, you have work to do. Start by identifying the five tasks only you can do, then systematically train someone else to handle four of them.

Standard operating procedures (SOPs) aren't just documents-they're proof that your business has transferable value. For my last exit, I had 47 documented SOPs covering everything from how we qualified leads to how we handled billing disputes. The buyer specifically mentioned this in their valuation memo as a reason they were comfortable paying a premium multiple.

Understand Your Valuation (And What Actually Drives It)

Most founders overvalue their business by 2-3x because they count the hours they've worked or their vision for what it could become. Buyers don't care about your effort or your dreams. They care about cash flow and risk.

Here's the math that matters:

SaaS businesses: Private SaaS companies are currently trading at 3-10x annual recurring revenue (ARR), depending on growth rate, churn, and profitability. The median is around 4.8x for bootstrapped companies and 5.3x for equity-backed companies. A SaaS company growing 40%+ year-over-year with monthly churn under 3% can command 7-10x multiples. Flat growth or declining growth? You're looking at 3-4x, sometimes less.

The Rule of 40 matters more than ever. Add your growth rate to your profit margin-if it's above 40%, you're in premium territory. If you're growing 30% annually with a 15% EBITDA margin, that's a 45% Rule of 40 score, which puts you in the top quartile for valuation. Companies below 20% on the Rule of 40 struggle to get decent multiples because they're either burning cash without growth or profitable but stagnant.

Service businesses and agencies: Usually 2-4x EBITDA. Lower multiples because they're harder to scale and often founder-dependent. If you've systematized it and removed yourself from operations, you might push toward the higher end. I've seen well-documented agencies with strong client retention sell for 4-5x EBITDA, but that's rare.

E-commerce: Generally 2-4x net profit, depending on product differentiation, customer concentration, and supply chain stability. Dropshipping businesses get lower multiples (1.5-2.5x) than brands with proprietary products and owned inventory (3-5x). Subscription e-commerce models can command higher multiples if retention is strong.

One of my SaaS exits sold for 5.2x ARR because we had strong unit economics, low churn (under 3% monthly), and a growing market. Another sold for only 2.8x because growth had stalled and the product needed significant technical debt addressed.

Customer concentration kills valuations. If one customer represents more than 10-15% of your revenue, buyers see that as a major risk. I've had buyers drop their offer by 20% when they discovered a single customer made up 30% of revenue. Diversify your customer base before you sell, or accept that you'll take a haircut on valuation.

Don't guess at your valuation. Look at actual comparable sales on marketplaces like Flippa to see what businesses in your category and revenue range are selling for. Filter by your industry, revenue size, and business model. The data is public and far more reliable than a broker's opinion of value.

Finding Buyers: Four Channels That Actually Work

When I sold my companies, I used a combination of direct outreach, brokers, and marketplace listings. Here's what worked:

Business Brokers (For Deals Over $500K)

If your business is worth over $500K, a broker is usually worth the commission. They have buyer networks, handle the paperwork, and keep the process moving when things stall. I used a broker for my largest exit and they found a buyer I never would have connected with on my own-a private equity firm looking specifically for B2B SaaS in my niche.

Broker commissions typically range from 8-12% for businesses under $1M, and they use tiered structures like the Double Lehman formula for larger deals. For a $5M sale, you'd pay roughly $300K in fees (10% on the first $1M, 8% on the second million, 6% on the third, 4% on the fourth, and 2% thereafter). That sounds like a lot, but a good broker can often increase your sale price by more than their fee through better buyer positioning and negotiation.

Interview at least three brokers. Ask for references from sellers they've closed for. Make sure they specialize in your business type-don't hire an e-commerce broker to sell a SaaS company. Check how many deals they've closed in the past 12 months in your valuation range. A broker who specializes in $10M+ deals isn't going to prioritize your $800K sale.

Red flags: brokers who charge large upfront fees (retainers over $15K for small deals), brokers who promise specific multiples without seeing your financials, and brokers who push you to list at a price far above market comps. Some brokers charge upfront fees and then don't prioritize your deal because they've already been paid. I prefer brokers who work primarily on success fees-they're incentivized to close.

Online Marketplaces (For Deals Under $500K)

For smaller exits, I listed on Flippa and similar platforms. These marketplaces have built-in buyer traffic, escrow services, and standardized processes. The fees are reasonable (usually 2-5%), and you can often close in 30-60 days if your business is clean.

The key is having all your documentation ready before you list: profit and loss statements, traffic analytics, customer data, growth trends. Buyers move fast on these platforms, and if you can't answer questions immediately, they move to the next listing.

Your listing needs to be comprehensive. Don't just list revenue-show profit, explain your customer acquisition strategy, detail your tech stack, and be transparent about challenges. The best listings I've seen include video walkthroughs of the business, detailed growth charts, and honest assessments of what the next owner needs to do to scale.

Marketplaces work well for online businesses, SaaS products under $500K, and e-commerce stores. They're less effective for agencies, local service businesses, or companies with complex financials that require extensive due diligence.

Direct Outreach to Strategic Buyers

For two of my exits, I directly contacted companies that would benefit from acquiring my customer base or technology. I identified competitors, adjacent product companies, and private equity firms investing in my space, then sent cold emails explaining why an acquisition made sense.

This approach takes longer but can result in higher valuations because strategic buyers pay for synergies. A competitor might pay more to acquire your customers than a financial buyer would pay for your profit stream. I built targeted lists of potential acquirers using ScraperCity's B2B database and then personalized outreach explaining the strategic fit.

The email template that worked for me: "We built [product] serving [market]. We have [number] customers paying [revenue]. I know you're focused on [their market], and I think there's a strategic fit. Would you be open to a conversation about an acquisition?" Short, direct, specific. No attachments on the first email-just gauge interest.

Strategic buyers often pay 20-40% more than financial buyers because they're buying market share, technology, or talent-not just cash flow. But the process is slower and more unpredictable. You might reach out to 50 strategic buyers and get two serious conversations.

Your Own Network

Don't underestimate telling people you're exploring a sale. I sold one business to someone I met at a conference who mentioned he was looking to acquire in my space. Another founder I know sold his agency to a former client who wanted to bring the service in-house.

Post about it (carefully) in founder communities, mention it to peers in your industry, and let your lawyer or accountant know you're open to offers-they often know buyers. I'm part of several founder groups where acquisition opportunities get shared regularly, and some of the best deals happen through these informal networks.

The key word is "carefully." Don't announce publicly that you're selling until you have a signed letter of intent. Tell people you trust, in private conversations, that you're open to the right opportunity. Frame it as exploring options, not as desperation to exit.

The Letter of Intent: Your First Real Commitment

Once you have a serious buyer, you'll negotiate a Letter of Intent (LOI). This is a non-binding document that outlines the basic terms of the deal: purchase price, structure (asset sale vs. stock sale), payment terms, due diligence timeline, and exclusivity period.

The LOI is critical because it sets expectations for everything that follows. If you agree to unrealistic terms in the LOI-like a 90-day close timeline for a complex business-you're setting yourself up for problems. Most LOIs give buyers 30-90 days for due diligence, during which they'll verify everything you've told them.

Key terms to negotiate in the LOI:

Purchase price and structure: Is this an asset sale or stock sale? Asset sales are cleaner for buyers (they don't inherit your liabilities) but can have different tax implications. Stock sales transfer everything-including potential liabilities-to the buyer. Most small business sales are asset sales.

Exclusivity period: Buyers will ask for 60-90 days where you agree not to talk to other buyers. This protects their time investment in due diligence, but don't agree to exclusivity periods longer than 90 days unless you're getting something in return. I've had buyers ask for six-month exclusivity, which is absurd-they're taking your business off the market while they decide if they want it.

Due diligence scope: What exactly will they examine? Financial records, customer contracts, legal documents, technical infrastructure? Define this clearly so you know what to prepare. Vague due diligence clauses lead to endless requests and delayed closings.

Conditions to closing: What has to happen for the deal to close? Financing approval? Regulatory approval? Key customer retention? The more conditions, the more likely the deal falls apart. Push back on conditions that are outside your control.

LOIs are usually 2-3 pages and written by the buyer. Read it carefully with your attorney before signing. Just because it's "non-binding" doesn't mean it's inconsequential-the terms in the LOI typically make it into the final purchase agreement with only minor changes.

Structuring the Deal: Cash, Earnouts, and Seller Financing

The deal structure matters as much as the price. I've seen founders celebrate a $2M sale only to realize only $800K was cash upfront, and the rest was tied to earnouts they'd never hit.

Here's what to negotiate:

Cash at closing: Push for as much upfront cash as possible. This is the only guaranteed money. For my exits, I aimed for at least 70% cash at closing. Anything less and you're taking on significant risk that the business performs post-sale. The current market standard is 60-80% cash at closing for small business acquisitions, with the remainder spread across earnouts, seller notes, or holdbacks.

Earnouts: These are payments tied to future performance-hit certain revenue or profit targets and you get additional payments. Buyers love earnouts because they reduce risk. I hate them because you no longer control the business but your payout depends on decisions the new owner makes.

Earnouts typically represent 15-50% of the total purchase price and last 1-3 years. Anything longer than three years should be viewed with extreme skepticism-too many variables can change. If you accept an earnout, make the targets realistic and based on revenue rather than profit. Profit can be manipulated through accounting decisions, but revenue is harder to game.

Also negotiate what happens if the buyer makes major changes that impact your ability to hit targets. What if they double the price of your product? What if they lay off your sales team? What if they merge your business into another division? These scenarios kill earnouts, and you need contractual protection against them.

I've seen earnout disputes destroy relationships and end up in litigation. One founder I know had an earnout based on EBITDA targets, and the buyer immediately increased "allocated corporate expenses" that reduced EBITDA below the threshold. He got nothing. If you must accept an earnout, hire a good attorney to draft protective language.

Seller financing: Sometimes buyers ask you to finance part of the purchase-they pay you over time instead of giving you all the cash upfront. This can make sense if it closes the deal and the buyer is creditworthy, but get a personal guarantee and security interest in the business assets so you can take it back if they default.

Seller notes typically carry interest rates of 5-8% and have terms of 2-5 years. If a buyer asks you to finance more than 20% of the purchase price, that's a red flag about their access to capital. Either they can't get bank financing (why not?) or they're trying to minimize their risk at your expense.

Holdbacks and escrow: Buyers often hold back 5-15% of the purchase price in escrow for 6-18 months to cover any issues that arise post-closing. This is standard practice and protects both parties. Make sure the escrow terms are clear-what triggers a claim against the escrow, and what's the process for releasing it?

Employment agreements: Some buyers want you to stay on for 6-12 months post-sale to transition the business. Negotiate your salary and responsibilities clearly. I did this for one exit and regretted it-I was contractually obligated to work for a new owner whose vision I disagreed with. Make sure you can live with the terms.

If you're staying on, clarify your authority. Are you running the business independently, or are you reporting to someone? Who approves major decisions? What happens if you disagree with their direction? These seem like minor details until you're three months into a miserable employment situation and can't leave without forfeiting part of your payout.

Due Diligence: What Buyers Will Dig Into

Once you have a letter of intent (LOI), the buyer starts due diligence. This is where they verify everything you've claimed and look for reasons to renegotiate or walk away. Expect this phase to take 30-90 days depending on business complexity.

They'll examine:

• Financial records for the past 3-5 years
• Tax returns and any audits or issues
• Customer contracts and concentration (if one customer is 40% of revenue, that's a red flag)
• Employee and contractor agreements
• Intellectual property ownership (make sure you actually own your code, brand, and content)
• Any legal disputes, liens, or liabilities
• Technology stack and technical debt
• Marketing channels and traffic sources
• Vendor relationships and key supplier contracts
• Insurance policies and coverage
• Permits, licenses, and regulatory compliance

For my SaaS exits, buyers brought in technical auditors to review the codebase. For one deal, they found security vulnerabilities that I had to fix before closing. For another, they discovered I didn't have IP assignment agreements with early contractors, and I had to track those people down and get retroactive signatures.

The cleaner you are going into due diligence, the less the buyer can use issues to renegotiate the price. I've had buyers try to knock $50K off the purchase price for minor issues they found. If your documentation is tight, you have leverage to push back.

Create a data room before due diligence starts. This is a secure folder (use Dropbox, Google Drive with restricted access, or a proper virtual data room service) containing all the documents buyers will request. Organize it by category: financials, legal, customers, employees, technology. The faster you can produce documents, the faster the deal closes.

Common due diligence red flags that kill deals:

• Revenue discrepancies between what you reported and what financial records show
• Customer contracts that are month-to-month with no commitment (high churn risk)
• Key customer relationships tied to you personally with no transition plan
• Outstanding legal issues or threatened litigation
• IP ownership disputes or missing assignments
• Undisclosed liabilities or off-balance-sheet obligations
• Regulatory compliance issues or expired licenses
• Technical debt so severe the product needs to be rebuilt

If buyers find material issues during due diligence, they'll either walk away, renegotiate the price, or ask you to fix the issues before closing. Small issues are expected-every business has some warts. Material issues that you didn't disclose will destroy trust and often kill the deal entirely.

Be proactive about disclosing problems. If you know there's an issue-a key customer is unhappy, a technical vulnerability exists, a legal dispute is brewing-tell the buyer upfront. It's better to control the narrative than to have them discover it and wonder what else you're hiding.

Negotiating the Purchase Agreement: Where Deals Get Real

After due diligence, you'll negotiate the definitive purchase agreement. This is the legally binding contract that governs the sale. It's typically 30-80 pages and covers every aspect of the transaction.

Key sections you need to understand:

Representations and warranties: These are your promises about the state of the business. You'll represent that your financial statements are accurate, you own all the IP, there are no undisclosed liabilities, etc. These reps and warranties survive closing, meaning the buyer can sue you if they turn out to be false.

Negotiate caps on your liability. Standard language says you're liable for any breach of reps and warranties, which could mean unlimited exposure. I always negotiate a cap at 10-20% of the purchase price, with a "basket" or threshold before claims can be made. For example, the buyer can only make claims if damages exceed $10K, and my total liability is capped at $200K (on a $1M sale).

Indemnification: This spells out who's responsible for what problems that arise post-closing. You'll typically indemnify the buyer for pre-closing liabilities, and they'll indemnify you for post-closing issues. Make sure the indemnification provisions are mutual and reasonable.

Non-compete and non-solicitation: Buyers will ask you to agree not to compete with the business for a certain period (usually 2-5 years) and not to solicit employees or customers. These terms are generally reasonable, but make sure they're not so broad that you can't work in your industry at all.

I've seen non-compete clauses that prohibited founders from "working in software" or "providing services to businesses." That's unreasonably broad. A fair non-compete is specific: you can't build a competing product in the same niche for the same customer base for three years. You can still work in software, just not in direct competition.

Working capital adjustments: The purchase price is usually based on a specific level of working capital (cash, receivables, inventory minus payables). If working capital at closing is different from the agreed-upon level, the price adjusts up or down. Make sure you understand how this calculation works-it can significantly impact your net proceeds.

Conditions to closing: These are things that must happen before the deal closes. Common conditions include buyer financing approval, no material adverse changes to the business, key contracts remaining in place, and regulatory approvals if needed. Don't agree to conditions you can't control.

The purchase agreement negotiation is where deals often fall apart. Attorneys get involved, egos clash, and small points become deal-breakers. Stay focused on the economics and don't let your attorney kill the deal over legal nuances that don't materially impact you. I've seen deals die because lawyers couldn't agree on indemnification language that differed by one word.

Closing and Transition: The Final 30 Days

Once due diligence is complete and the purchase agreement is signed, you'll close the deal. Money gets wired to escrow, documents get signed, and ownership transfers. For my exits, closing took 1-3 days once all parties agreed to final terms.

Then comes the transition period. Even if you're not staying on as an employee, plan to spend 2-4 weeks helping the new owner understand the business. Introduce them to key customers, walk them through systems, and hand over all logins and documentation. Do this professionally even if you're burned out and ready to move on-your reputation matters, and the buyer might still be holding earnout money or could come after you for misrepresentation if things go wrong.

I created a transition checklist for my last exit that included every login, every vendor contact, every process document, and every customer relationship. The new owner appreciated it, the transition went smoothly, and I got a strong reference for future deals.

Specific items to hand over during transition:

• All admin logins and credentials (use a password manager to share these securely)
• Banking information and financial account access
• Vendor contacts and contract details
• Customer list with relationship notes
• Employee information and HR files
• Marketing materials and brand assets
• Technical documentation and source code access
• Process documentation and SOPs
• Introduction emails to key customers and partners

If customers need to be notified about the ownership change, coordinate messaging with the buyer. Some buyers want to notify customers immediately, others want to wait until integration is complete. I prefer getting ahead of it-customers will find out anyway, and it's better they hear it from you in a controlled message than through the grapevine.

Plan for the emotional side of transition. You've built this business, and handing it over to someone else is harder than you think. I felt relieved after my first exit, then weirdly empty for about two weeks. By my fifth exit, I knew to expect this and had a plan for what came next. Don't underestimate the psychological impact of selling something you've poured years into.

Common Mistakes That Kill Deals

Based on my exits and deals I've watched fall apart:

Waiting until you're burned out to sell: Buyers can smell desperation. If your business is declining and you're trying to exit before it gets worse, you'll get lowball offers. Sell from a position of strength when the business is growing and you have options.

Not having an exit strategy from day one: I structure every business I start as if I'm going to sell it. Clean books, documented processes, separated finances. Even if you plan to run it for 20 years, building it to sell makes it more valuable and easier to operate.

Overvaluing emotional attachment: Your business is not your baby. It's an asset. Buyers don't care about the late nights or the challenges you overcame. They care about cash flow and growth potential. Price it based on market comparables, not your feelings.

Negotiating directly without legal help: Hire a lawyer who specializes in mergers and acquisitions. The purchase agreement is the most important document you'll sign. I've seen founders lose hundreds of thousands because they didn't understand indemnification clauses, escrow terms, or earnout structures. Don't be cheap here. A good M&A attorney costs $15K-$30K but can save or make you multiples of that.

Talking publicly about the sale too early: Don't announce you're selling until the deal is done. Employees get nervous, customers start asking questions, and competitors smell blood. Keep it quiet until the money is in your account. I've seen deals fall apart because a founder mentioned they were selling to the wrong person, and word got back to employees who then started looking for other jobs.

Accepting the first offer: Just because someone offers to buy your business doesn't mean it's a good offer. Get multiple bids if possible. Run a competitive process. Even if you're not talking to other buyers, never let the current buyer think they're the only option. I increased my sale price by $300K on one deal simply by mentioning that I'd been approached by others (which was true).

Ignoring culture fit: If you care about what happens to your business, your employees, and your customers after the sale, evaluate the buyer beyond just their offer. Some buyers will gut your team, others will nurture what you built. I turned down a higher offer once because the buyer's plan was to offshore my team and automate everything-I didn't want that for the people who'd helped build the company.

Failing to plan for taxes: The tax bill from selling your business can be 20-40% depending on your structure, deal type, and state. Set aside money immediately for taxes and talk to a CPA about strategies to minimize the hit. There are approaches like Qualified Small Business Stock (QSBS) exclusion, installment sales, and opportunity zone investments that can significantly reduce taxes if planned correctly.

Different Types of Buyers (And What Each One Wants)

Not all buyers are the same. Understanding what different buyer types care about helps you position your business correctly.

Individual buyers: Often first-time business owners looking for a lifestyle business. They care about cash flow, stability, and simplicity. They don't want complex tech stacks or processes that require specialists. They'll pay 2-4x EBITDA typically and want you to stay on for transition. Best for: service businesses, agencies, small SaaS products under $500K.

Strategic corporate buyers: Companies in your industry or adjacent markets. They care about customer acquisition, technology advantages, and market share. They'll pay premium multiples (20-40% above market) because they're buying synergies, not just cash flow. They move slowly due to corporate bureaucracy. Best for: businesses with unique IP, strong market positions, or complementary customer bases.

Private equity firms: Financial buyers looking for returns. They care about growth potential, defensibility, and management team. They want to buy, improve, and sell your business in 3-7 years. They'll push for earnouts tied to growth and want you to stay on to scale it. They typically pay 4-8x EBITDA depending on size and sector. Best for: businesses doing $1M+ EBITDA with clear growth pathways.

Competitors: They know your space and will do deep diligence. They care about eliminating competition, acquiring customers, and consolidation plays. Pricing can be unpredictable-they might overpay to keep you off the market or lowball because they know your challenges. Be careful about sharing sensitive information with competitors during diligence. Best for: businesses with strong customer bases or market positions that complement theirs.

Search fund buyers: MBAs or career switchers who've raised money to buy and run a business. They're buying a job as much as an investment. They care about stability, trainability, and businesses they can understand. They move quickly and often overpay because they're using other people's money and are personally motivated to close. Best for: established, stable businesses where founder involvement isn't critical.

When NOT to Sell Your Business

Sometimes the right answer is not to sell. Here are situations where you should wait or reconsider:

If your business is declining and you're trying to exit before it gets worse. Fix it first or accept that you'll get a distressed valuation. I've seen founders try to sell during downturns and end up accepting offers 40-50% below what they could have gotten a year earlier.

If you're getting lowball offers that don't reflect your business's value. Don't sell out of frustration. Either improve the business to command better offers, or wait for market conditions to improve. SaaS valuations dropped 60% from 2021 peaks-sellers who waited and kept growing are now seeing multiples recover.

If you don't have a plan for what comes next. Selling your business without a clear vision for what you'll do afterward leads to regret and boredom. I've seen multiple founders sell, realize they miss the work, and start competing businesses within a year (often violating their non-compete and ending up in legal disputes).

If the only buyers are strategic competitors who will destroy what you've built. Money isn't everything. If you care about your team, your customers, and your legacy, don't sell to someone whose plan is to gut the business for parts.

If you're within 6-12 months of a major milestone that would significantly increase valuation. If you're about to close a big partnership, launch a new product line, or hit a key revenue threshold, waiting might make more sense. I delayed one sale by six months to cross $1M ARR, which moved me into a different valuation tier and resulted in a $400K higher sale price.

Alternative Exit Strategies Beyond Full Sale

Selling 100% of your business isn't the only option. Consider these alternatives:

Partial sale/minority stake: Sell 20-40% to an investor or strategic partner, get liquidity, but maintain control and upside. This works well if you want to keep running the business but need capital to scale or want to diversify your personal wealth. Private equity firms often do minority investments in growing businesses.

Acquihire: If your team is more valuable than your revenue, consider an acquihire where a buyer acquires your company primarily for the talent. Common in tech when products haven't found product-market fit but the team is strong. Valuations are typically $500K-$2M per key employee.

Merger: Combine with a competitor or complementary business rather than getting acquired. You own a portion of the combined entity and participate in future upside. This works when two businesses together are worth more than the sum of parts.

Management buyout: Sell to your existing management team. They know the business, transition is easy, and you maintain good relationships. Financing can be tricky-they'll need bank loans or seller financing since they typically don't have cash to buy you out.

Employee stock ownership plan (ESOP): Transfer ownership to employees over time through a structured program. Provides tax benefits and maintains company culture, but complex to set up and not suitable for all business types.

Holding and extracting cash: Instead of selling, optimize the business to throw off maximum cash flow and pay yourself distributions. If your business generates $500K/year in profit and you can't get a good valuation, maybe it's better to own it and extract cash for 5-10 years rather than selling for 3x.

What to Do After You Sell

After my first exit, I had no plan. I took three months off, got bored, and started another company without thinking through what I actually wanted. By my fifth exit, I had a clear plan: invest the proceeds, take time to evaluate what kind of business I wanted to build next, and avoid rushing into anything out of habit.

Here's what I recommend:

First, handle the taxes. Depending on your deal structure and entity type, you could owe 20-40% in taxes. Set that money aside immediately and talk to a CPA who specializes in exit tax planning. There are strategies to minimize taxes if you plan ahead-QSBS exclusions, opportunity zones, charitable remainder trusts, installment sales. Don't wait until April to figure this out.

Second, resist the urge to immediately start another company. Take at least 60 days to decompress and think about what you actually want. I've seen founders sell, start a new venture within weeks, and repeat the same mistakes because they didn't take time to reflect. You just executed a major transaction-give yourself time to process it.

Third, if you're thinking about what to build next, focus on systems and processes from day one. The lessons from preparing for an exit apply to running a better business even if you never sell. I document everything now, separate my finances, and build teams that can operate without me-not just to make the business sellable, but because it's a better way to operate.

Consider investing the proceeds rather than starting something new immediately. I put exit proceeds into index funds, real estate, and angel investments in other founders' companies. Diversifying your wealth after a sale is smart-you've just converted an illiquid, concentrated asset (your business) into liquid cash. Don't immediately reconcentrate it in another single venture.

If you do want to start another business, pick something you're genuinely excited about rather than just repeating what worked before. My most successful companies came from solving problems I was personally frustrated by, not from trying to replicate previous successes.

Think about non-financial goals. Now that you have liquidity, what do you actually want from the next phase? More time with family? Geographic freedom? Working on harder problems? Building a team? I know founders who sold companies, traveled for a year, then came back and built something completely different because they had clarity on what mattered.

If you want structured help building a business that's both profitable and sellable, I go deeper into these frameworks inside Galadon Gold. You can also grab my 7-Figure Agency Blueprint for specific processes around scaling and systematizing service businesses, which directly impacts sellability.

Tools and Resources That Help You Prepare

Specific tools I've used across my exits:

For finding potential buyers, ScraperCity's database helped me build targeted lists of strategic acquirers and private equity firms. For one exit, I identified 40 PE firms that had invested in my space, reached out to 12, and got three serious conversations that drove up my eventual sale price.

For valuation research, spend time on Flippa looking at comparable sales. Filter by your revenue range, industry, and business model. Look at what actually sold, not just asking prices. This gives you realistic expectations.

For process documentation, I use a combination of Loom for recording processes, Notion for documentation, and Trainual for building training systems. The key is having everything centralized and searchable so when buyers ask "how do you handle X," you can send them a link to documentation.

For financial cleanup, hire a fractional CFO or bookkeeper who understands acquisitions. They'll know what buyers look for and can help you structure your financials correctly. This is not the time for your cousin who "knows QuickBooks."

For legal help, find an M&A attorney, not a general business lawyer. M&A deals have specific structures, terms, and pitfalls that generalists don't understand. Ask other founders who've sold for referrals.

For finding brokers, ask for referrals from founders who've successfully exited in your space. Don't just Google "business broker"-find someone with specific experience selling businesses like yours in your valuation range.

The Reality of Multiple Exits: What I Learned Selling Five Companies

Each exit taught me something different. The first was messy-I overpaid on taxes, underestimated how much work transition would be, and didn't negotiate protective terms in the purchase agreement. I learned.

By the fifth exit, I had a system: start preparing 18 months before I wanted to sell, clean financials monthly, document everything, build a team that could operate without me, reach out to strategic buyers early to gauge interest, negotiate from strength, and never accept the first offer.

The biggest lesson: selling a business is a skill, just like building one. Founders who treat the exit process as seriously as they treat product development or sales get much better outcomes. Founders who wing it or rely solely on advisors leave money on the table.

You don't need five exits to get this right. You just need to prepare properly, understand what buyers actually value, and be willing to walk away from bad deals. Build something people want to buy, clean up your operations and financials, find the right buyers, and negotiate intelligently.

The Bottom Line

Selling a business isn't a one-time event-it's the result of running a clean, systemized, growing operation that someone else wants to own. The founders who get the best exits are the ones who prepare years in advance, not the ones scrambling to clean up their books and processes when a buyer shows interest.

I've sold five companies because I built them to sell from the beginning. Clean financials, documented processes, separated operations, and realistic valuations based on market data. If you're asking "how can I sell my business," start by making it worth buying. Everything else is just execution.

The current market favors prepared sellers. Valuations have stabilized after the volatility of recent years, buyers have capital to deploy, and there's strong demand for quality businesses with predictable cash flow and growth potential. If your business checks those boxes and you've prepared correctly, you're in a strong position to get a good exit.

Start now. Even if you're not planning to sell for three years, begin building the systems, documentation, and financial cleanliness that will maximize your valuation when the time comes. Future you will thank present you for the discipline.