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Entrepreneurship Through Acquisition: The Search Fund Playbook

The fastest path to owning a profitable business isn't starting one-it's buying one that already works.

Why Buying Beats Building

I've started five SaaS companies from scratch and sold all of them. And I'll tell you this: if I could go back and do it again, I'd seriously consider buying an existing business instead of building the first one.

Here's why entrepreneurship through acquisition makes sense: you skip the hardest part. No product development hell. No finding product-market fit. No burning cash while you figure out if anyone actually wants what you're selling. You buy a business that already has customers, revenue, and proven unit economics.

The traditional search fund model works like this: you raise money from investors to search for and acquire a business, then run it for 5-10 years before exiting. But there's also the self-funded model where you use your own capital, SBA loans, or seller financing to buy smaller businesses.

Both paths work. The question is which one fits your situation.

The numbers back this up. Recent data shows that 63% of search funds successfully acquire a company, and of those that acquire and exit, the aggregate pre-tax internal rate of return stands at 35.1% with an average 4.5x return on invested capital. Compare that to startups, where roughly 90% fail within the first seven to ten years. The math isn't even close.

The Search Fund Model Explained

A traditional search fund starts with capital raising. You pitch investors on your background and ability to find, acquire, and operate a business. The median search fund now raises around $500K for the search phase-that's your salary and operating costs while you look for the right company to buy.

Once you find a target, you go back to those same investors plus new ones to raise acquisition capital. Recent deals show a median purchase price of $14.4M in enterprise value, down slightly from previous years due to higher interest rates, but still substantial. You become CEO, typically own 20-30% of the equity (with potential to earn up to 25% through performance), and run the business for years before selling.

The success rate? About 63% of search funds successfully acquire a company. Of those that acquire, roughly 69.5% generate positive returns for investors, with the majority falling in the 2x-5x return range. Those aren't bad odds if you have the pedigree-most successful searchers come from MBA programs (particularly Stanford, Harvard, or similar tier schools), investment banking, or consulting. Investors want to see that you can analyze deals, run operations, and lead a team.

The typical search lasts about 20 months before a deal closes. During that time, you're living off investor capital, reviewing hundreds of businesses, making dozens of offers, and getting rejected over and over. It's mentally exhausting, but you're not risking your own money during the search phase.

Self-Funded Acquisitions: The Smaller, Faster Path

Here's where it gets more accessible. You don't need to raise millions or have an MBA to buy a business. The self-funded search space focuses on smaller deals-businesses generating $200K-$2M in seller's discretionary earnings (SDE).

These deals typically cost 2-4x SDE. So a business throwing off $500K per year might sell for $1.5M-$2M. You finance it with some combination of:

The advantage? You can own 60-100% of the business from day one. The disadvantage? You're signing personal guarantees on SBA loans, and if the business tanks, you're holding the bag. That's a very different risk profile than the traditional search model where investors absorb most of the downside.

I know operators who've bought $2M revenue service businesses with $150K down and an SBA loan. They run them for 3-5 years, grow them to $4M-$5M, then sell for 5-6x EBITDA. That's a $3M-$5M exit on a $150K initial investment. Not bad math.

Self-funded searchers also have complete control. No board to report to, no investors questioning your decisions. You're the owner, not just the CEO. That autonomy is worth something, especially if you have strong operational instincts and don't want to be managed.

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The Key Differences: Traditional vs. Self-Funded

The choice between traditional and self-funded isn't just about deal size-it's about risk tolerance, equity ownership, and lifestyle.

Deal size and capital requirements: Traditional search funds target businesses with $2M-$5M+ in EBITDA, requiring $10M-$50M in total capital. Self-funded deals focus on $500K-$2M EBITDA businesses, requiring $150K-$500K in down payment capital. If you don't have access to half a million in investor capital or personal savings, self-funded might not be realistic.

Ownership and upside: Self-funded searchers typically own 60-100% of the equity. Traditional searchers start with 20-25% and can earn up to 30% through performance milestones. In dollar terms, the traditional model often creates more absolute wealth because you're operating a larger business, even with smaller ownership. A 25% stake in a $50M exit beats 100% of a $3M exit.

Risk and downside protection: This is the big one. Traditional searchers have their downside capped at zero-if the business fails, they lose their equity stake but aren't personally liable for debt. Self-funded searchers personally guarantee SBA loans, meaning a failed acquisition could cost you hundreds of thousands of dollars out of pocket. That's a gut-wrenching reality if you have a family and a mortgage.

Search capital and runway: Traditional searchers get paid a salary (typically $130K) during the 12-24 month search phase. Self-funded searchers either search part-time while employed elsewhere or burn through personal savings. You also eat all dead deal costs-legal fees, travel, QoE reports-which can add up to tens of thousands before you ever close a deal.

Investor support and accountability: Traditional searchers gain experienced mentors who've done this before. Your investor group becomes your board, offering guidance on operations, hiring, and strategy. The flip side? They can fire you if performance tanks. Self-funded searchers have complete autonomy but no safety net. You figure it out as you go.

Exit expectations: Traditional search funds have a clear expectation: you will sell the business to create liquidity for investors, typically within 5-8 years. Self-funded searchers can hold indefinitely, extracting cash flow as personal income and never selling if they don't want to. That optionality matters if you're building a lifestyle business versus maximizing IRR.

What Types of Businesses Work Best

You want boring businesses that print money. I'm talking about:

What you don't want: restaurants, retail stores, businesses dependent on the founder's personal relationships, anything in a dying industry, or businesses with 1-2 huge customers representing 50%+ of revenue.

The best acquisition targets have these characteristics:

I look for businesses where the current owner is checked out or doesn't know how to grow. If I can see three obvious ways to double revenue in 24 months, that's a business worth buying.

Valuation multiples vary significantly by industry and business size. Service businesses typically sell for 2.5-4x SDE. Software companies with recurring revenue command 3-6x SDE or higher. Larger businesses with over $2M in EBITDA might trade at 5-8x EBITDA, especially if they have strong margins and recurring revenue. Understanding these benchmarks helps you spot overpriced deals and negotiate effectively.

How to Actually Find Deals

Deal sourcing is everything. The businesses listed on BizBuySell and similar marketplaces are picked over, overpriced, or have problems. You want off-market deals.

Here's how to find them:

Cold outreach to business owners. Build a list of target companies in your chosen industry, then reach out directly. Use ScraperCity's B2B database to find contact info for business owners in specific industries and revenue ranges. Your pitch: you're looking to acquire a business in their space and want to have a conversation, even if they're not actively selling.

Most owners who sell weren't planning to sell until someone made them an offer. Reach out to 500 businesses, get 20 conversations, and maybe 2-3 serious opportunities emerge. If you need to verify those email addresses before sending, an email validation tool will help you maintain good deliverability.

Work with business brokers. Yes, brokered deals are more expensive. But brokers also handle a significant portion of the deals that actually close. Build relationships with brokers who specialize in your target industry and deal size. Tell them exactly what you're looking for. When the right deal comes in, you want to be their first call.

The key with brokers is standing out. Most buyers who contact brokers never close a deal. Show proof of funds, demonstrate you understand the industry, and respond quickly. Brokers will prioritize serious buyers who can actually execute.

Network in industry associations. Every industry has conferences, trade associations, and online communities. Show up. Tell people you're looking to buy. You'd be surprised how many deals happen because someone knew someone whose brother-in-law wanted to retire.

Partner with accountants and lawyers. CPAs and business attorneys know which of their clients are thinking about exiting. If you can become the go-to buyer in your niche, they'll send deals your way. Offer a referral fee if a deal closes-that aligns incentives.

Direct mail and targeted advertising. Some successful searchers send physical letters to business owners in their target demographic. A well-crafted letter to 1,000 business owners aged 60+ in your target industry might generate 5-10 responses. It's old school, but it works because so few people do it anymore.

I cover the entire outbound process for this inside my Discovery Call Framework-the same techniques work whether you're selling services or buying a business. The psychology of the initial conversation is identical: build trust, understand their situation, position yourself as the solution.

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The Baby Boomer Opportunity

Here's the macro trend that makes this the perfect time to pursue entrepreneurship through acquisition: baby boomers own approximately 12 million businesses in the United States-roughly two-thirds of all companies. About 10,000 baby boomers turn 65 every single day.

These owners are sitting on an estimated $10 trillion in business value. Most have no succession plan. Studies show that over 58% of small business owners have no transition or exit strategy whatsoever. Only about 15% have undergone professional business valuations.

Why don't they have plans? Several reasons:

This creates a massive opportunity window. In many cases, you're not competing against other buyers-you're competing against the owner doing nothing and continuing to run the business until they physically can't anymore.

The businesses with the best opportunities are often those where the owner is in their late 60s or early 70s, checked out operationally, but the business still runs profitably because of strong systems and employees. You're not buying the owner's expertise-you're buying a cash-flowing asset that's been on autopilot.

The flip side? If millions of businesses hit the market simultaneously, could valuations drop? Some predicted a buyer's market, but it hasn't materialized yet. Deal flow has increased, but so has the number of searchers and private equity firms moving down-market. Quality businesses with strong financials and recurring revenue still command premium multiples.

Due Diligence: Don't Skip This

Once you find a business you want to buy, due diligence is where deals die-or where you discover you're buying a lemon.

You need to verify everything the seller told you:

Hire a quality of earnings (QoE) report from an accounting firm for any deal over $1M. It costs $10K-$25K but will save you from buying a disaster. The QoE digs deeper than standard financials, adjusting EBITDA for one-time items, normalizing owner compensation, and identifying risks.

I've walked away from three acquisition deals during due diligence. One had undisclosed IRS tax debt. Another's financials didn't match bank deposits by 40%. The third had a key customer accounting for 65% of revenue who was planning to churn. Walking away is painful-you've invested time and money-but necessary.

Budget 4-12 weeks for due diligence on a typical small business acquisition, longer for complex deals. Don't rush this phase to meet a seller's timeline. Any seller pressuring you to skip diligence is hiding something.

Structuring the Deal

Deal structure matters as much as price. A $2M deal with seller financing and earnouts is very different from $2M all cash at close.

Here's what I typically see in lower middle market deals:

Seller financing and earnouts align incentives and reduce your upfront capital needs. They also protect you-if the business underperforms, you're not fully out the purchase price. The seller stays invested in your success during the transition period.

On SBA deals, you'll need 10-15% down payment, the SBA loan covers 75-90%, and seller financing covers the gap. The SBA limits how much seller financing you can have (typically 5% of the purchase price on a standby basis for 24 months), so work with an SBA-experienced attorney and lender. SBA 7(a) loans can finance up to $5M with terms up to 10 years for working capital and acquisitions, or up to 25 years if the loan includes real estate.

Current SBA loan default rates hover below 3.5%-dramatically better than startup failure rates-which is why lenders are willing to finance acquisitions for qualified buyers. That said, you're personally guaranteeing the debt. If you default, they can come after your house, your savings, everything. Don't take that lightly.

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Operating the Business Post-Acquisition

You bought it. Now what?

The first 90 days are critical. Your goals:

Don't come in swinging with major changes. I've seen acquirers lose 30% of staff in month one because they immediately reorganized everything. That kills the business. Employees are nervous about new ownership. They're worried about layoffs, culture changes, and whether you actually know what you're doing.

Spend weeks shadowing every role. Understand why things are done the way they're done. Most processes exist for a reason, even if they seem inefficient at first glance. Then make strategic improvements: fix pricing, improve marketing, add new services, streamline operations.

The best growth levers in acquired businesses are usually obvious and under-executed:

If you know how to generate leads and close deals-which you should if you've read this far-you can bolt that onto almost any service business and grow 30-50% in year one. Most small business owners are great operators but terrible at marketing and sales. That's your competitive advantage.

I break down the exact outbound playbook in my 7-Figure Agency Blueprint. The principles apply whether you're growing an agency or a newly acquired HVAC company. Build a list, create an offer, reach out systematically, close deals, deliver results, repeat.

Common Mistakes New Acquisition Entrepreneurs Make

I've watched enough acquisitions (both successful and disastrous) to identify patterns in what kills deals post-close.

Overestimating your ability to grow the business quickly. You see three obvious growth opportunities and assume you can double revenue in 12 months. Then reality hits: the owner tried two of those ideas and they didn't work for reasons you didn't uncover in diligence. The third requires capabilities you don't have. Growth takes longer than you think.

Underestimating the importance of the seller transition. The seller knows where all the bodies are buried. They have relationships with key customers, know which employees are critical, understand seasonal cash flow patterns. If they leave immediately and you're scrambling to figure everything out, customers get nervous and employees start looking for other jobs. Negotiate a 3-6 month transition period where the seller is available to answer questions.

Changing too much too fast. You're excited about improvements. You want to prove you can grow the business. But customers bought from the previous owner because they liked how things were done. Employees have routines that work. Rapid change creates chaos. Make changes incrementally, communicate clearly, and bring people along.

Ignoring company culture. This sounds soft, but it matters. If the previous owner ran a family-oriented culture with flexibility and you come in demanding 60-hour weeks and rigid accountability, people will quit. Understand the culture you're inheriting and decide what you want to preserve versus change.

Running out of working capital. You financed the acquisition with maximum leverage, leaving minimal cash buffer. Then a large customer pays 60 days late, or a key piece of equipment breaks, or you need to hire someone urgently. Suddenly you're scrambling to make payroll. Always maintain 3-6 months of operating expenses in reserve.

Not building your own deal flow engine. One acquisition is great. But the real wealth in this space comes from doing multiple deals. The skills you develop in your first acquisition-sourcing, diligence, negotiation, operations-compound. Many successful searchers acquire one business, run it for 3-5 years, sell, then do it again with a larger target. Build relationships with brokers, investors, and sellers even after you close your first deal.

Exit Strategy: When and How to Sell

Your exit starts the day you buy. Every decision should be made with the eventual sale in mind.

Buyers pay premiums for businesses that:

Most operators hold for 3-5 years. That's enough time to implement growth strategies, realize value, and still exit before you're burned out. Traditional search funds typically exit after 5-8 years to provide liquidity to investors.

Typical exit multiples are higher than acquisition multiples if you've executed well. A $500K SDE business you bought for 2.5x ($1.25M) could easily sell for 4-5x if you grew it to $1M SDE. That's a $4M-$5M exit on a business you bought for $1.25M. Do that with 80% leverage and your actual cash-on-cash return is absurd.

EBITDA multiples for exits vary by industry and business characteristics. Technology and software businesses command 7-12x EBITDA. Professional services typically see 5-10x. Manufacturing and distribution fall in the 4-7x range. Businesses with over 20% EBITDA margins, recurring revenue, and low customer concentration consistently get premium multiples.

I've exited five companies. The ones where I had clean books, documented systems, and wasn't needed in daily operations sold for the highest multiples with the least friction. The one where I was still the primary rainmaker and operator? That was a nightmare to sell and got a garbage multiple. Buyers discount heavily for owner dependency.

When you're ready to exit, your options include:

Work with an M&A advisor or business broker for any exit over $2M. Yes, they take 5-10% of the sale price, but they'll get you a higher multiple, manage the process, and bring multiple buyers to create competition. The extra 1-2x in multiple they generate more than pays for their fee.

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Alternative Models Worth Considering

Beyond traditional and self-funded search, several hybrid models have emerged:

Search fund accelerators. Programs that provide seed capital, training, and investor introductions in exchange for an equity stake or fee. They compress the learning curve and provide community support. Typical programs last 6-12 months. The trade-off is less autonomy and potential dilution, but you gain structure and mentorship.

Independent sponsor model. You identify and negotiate a deal first, then raise equity and debt financing on a deal-by-deal basis. This offers flexibility for experienced operators who have strong investor networks but don't want to commit to a traditional search fund structure. You maintain more control over deal selection and timeline.

Crowdfunded search. Raising capital from many small investors via equity crowdfunding platforms. This democratizes access but creates complexity in managing a large investor base. Roughly 30% of crowdfunded searches close an acquisition within the planned timeframe-lower than traditional search, but viable for certain situations.

Sponsored search. A single wealthy individual or family office funds your search and acquisition. You get capital and mentorship from one source, simplifying governance. The sponsor typically takes a larger equity stake than in a traditional search fund, but the relationship can be more flexible and long-term oriented.

Each model has trade-offs in capital requirements, equity ownership, autonomy, and support. The right choice depends on your network, experience, risk tolerance, and deal size targets.

Skills That Matter Most

What actually determines success in entrepreneurship through acquisition? After watching dozens of operators over the years, a few skills separate winners from losers:

Deal sourcing persistence. You'll hear "no" hundreds of times before you close one deal. Most searchers give up after 50 rejections. The ones who succeed treat deal flow like a numbers game and systematically work through lists of targets without taking rejection personally.

Financial analysis. You need to read financials, spot red flags, build models, and understand how different deal structures impact returns. If you can't build a sources and uses table or calculate normalized EBITDA, learn now. This is table stakes.

Operational improvement. Identifying growth opportunities is easy. Actually executing them is hard. Can you build and manage a team? Implement systems? Hold people accountable? Allocate capital effectively? These blocking-and-tackling skills determine whether you grow the business or run it into the ground.

Sales and marketing. Most small businesses suck at generating new customers. If you can systematically create pipeline through outbound, paid ads, content, or partnerships, you have an unfair advantage. This is my background, and it's made every acquisition and business I've touched significantly more valuable.

Negotiation. You'll negotiate with sellers, lenders, lawyers, key employees, and customers. The ability to structure win-win deals, hold your ground on key terms, and build trust through the process directly impacts your success.

Emotional resilience. Searches are mentally exhausting. Deals fall apart after months of work. Businesses underperform post-acquisition. Key employees quit. If you need constant validation and can't handle ambiguity, this path will destroy you. The operators who succeed embrace uncertainty and keep moving forward.

Building Your Search Funnel

Think of your search like a sales funnel. You need volume at the top to get one deal closed at the bottom.

Here's what a realistic 24-month search funnel looks like:

These numbers vary based on your industry, deal size, and approach, but the principle holds: you need massive top-of-funnel activity to close one deal. Most failed searchers don't contact enough businesses. They spend months perfecting their investment thesis and building financial models, then reach out to 50 companies and wonder why nothing materializes.

Build your list using tools that compile B2B data filtered by industry, revenue range, company age, and geography. Then work that list systematically. Track every interaction in a CRM. Follow up persistently. Build relationships even when someone says they're not ready to sell-they might be ready in six months.

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The Financial Reality Check

Let's talk money. What does a typical self-funded acquisition actually return?

Say you buy a business for $2M at 3x a $667K SDE. You put down $300K (15%), take an SBA loan for $1.5M (75%), and negotiate a $200K seller note (10%). Your debt service on the SBA loan at 8% over 10 years is roughly $18K/month or $216K/year.

In year one, the business generates $667K in SDE. After debt service, you have $451K in cash flow. From that, you need to pay taxes (assume 30% effective rate), leaving you $316K in after-tax cash flow in year one.

Not bad for a $300K investment, right? That's a 105% cash-on-cash return in year one. But remember, you're working full-time as the operator. That cash flow includes your salary.

Now assume you grow SDE 20% per year through operational improvements, pricing increases, and new customer acquisition. By year five, SDE is $1.39M. Your debt balance is down to $1M. After debt service ($216K) and taxes, you're clearing roughly $800K per year in cash flow.

You decide to sell in year five. At 4x SDE (higher than you paid because you've de-risked the business), the sale price is $5.56M. After paying off the $1M remaining debt and $200K seller note, you net $4.36M. Plus you've taken out roughly $2.5M in cumulative cash flow over five years (after debt service and taxes).

Total return: $6.86M on a $300K investment over five years. That's a 23x multiple or roughly 110% IRR.

This is aggressive but achievable if you buy right, operate well, and sell at the right time. Mess up any of those three things and your returns look very different.

Resources and Next Steps

If you're serious about entrepreneurship through acquisition, here's how to actually get started:

Educate yourself. The Stanford Search Fund Primer is essential reading. Study the annual Stanford Search Fund Study for performance data and trends. Join communities like Searchfunder.com where active searchers share deal flow strategies and war stories.

Pick your model. Traditional or self-funded? What deal size can you realistically pursue given your capital and network? Don't try to raise a traditional search fund if you don't have the pedigree and investor connections. Conversely, don't go self-funded if you can't afford to personally guarantee $1M+ in debt.

Build your network. Connect with search fund investors, business brokers, SBA lenders, and other searchers. Go to ETA conferences. Join LinkedIn groups. Most searchers underestimate how much of this game is relationships and pattern recognition from others who've done it before.

Define your investment criteria. What industries do you understand? What geography are you willing to search in (and relocate to)? What revenue and EBITDA range makes sense? Narrow your focus-industry-specific searches outperform generalist approaches because you build expertise and deal flow in one vertical.

Start building your list. Don't wait until you've raised capital or quit your job. Start identifying target businesses now. Reach out to owners. Have exploratory conversations. You'll learn more from ten real conversations with business owners than from six months of reading case studies.

If you need help systematizing your outreach and lead generation-whether for acquiring a business or growing one post-acquisition-I walk through the entire framework inside my coaching program. The same principles I use to generate sales meetings for agencies apply to deal sourcing for acquisitions.

Is This Right for You?

Entrepreneurship through acquisition isn't for everyone. You need:

But if you have those things, buying a business is one of the fastest paths to owning a real, cash-flowing asset. You skip the startup risk, start with revenue from day one, and can focus on growth instead of survival.

I still build businesses from scratch because I enjoy it and know how to de-risk the early stages. But if I were advising someone who wanted to be an entrepreneur and had $100K saved up? I'd tell them to buy, not build.

The opportunities are there. Baby boomers own 12 million businesses and most have no succession plan. Private equity has moved down-market but still largely ignores sub-$2M EBITDA deals. That's your window.

The next decade will see the largest transfer of business ownership in American history. Trillions of dollars in business value will change hands. Some of those businesses will close because no buyer stepped up. Others will sell to operators who saw the opportunity and positioned themselves to capitalize.

Which side of that equation do you want to be on?

Go find a boring, profitable business. Buy it. Grow it. Sell it. Repeat.

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