How to Choose Your First Startup Acquisition

Is there anything more exciting than acquiring your first startup?

You get to apply your hard-earned skills and experience to transform an established business and ultimately sell it for a life-changing sum.

However, all “firsts” have the capacity to disappoint as well as delight. Many prefer to think of your first acquisition as a trial run rather than an all-in bet on your first hand.

Consider your goals, which startups would be a good fit for your expertise, and how you’ll generate a return on your investment.

If it doesn’t work out, you can apply what you’ve learned to your next acquisition. But if you bite off more than you can chew now, you risk everything with no guarantees.

First, Identify Your Strengths

Before you even look at startup listings, start with some self-reflection.

What are you good at? What are you passionate about? What makes you different from other entrepreneurs? Where do you add the most value?

If you’re an ex VP Sales, for example, who loves building relationships and hitting targets, your shortlist will differ from that of a full-stack engineer who adores APIs and algorithms.

You’d be surprised how few entrepreneurs ask these questions before acquiring a startup, only to later realize they lack the skills to grow the company, or hate the industry, or work so much it’s a chore to do so. 

A real-world example:

Chan Yerneni was an entrepreneur from India who’d previously run a small school before moving to Canada to work in tech. Though he managed to work his way up the corporate ladder in Toronto, he craved to run his own startup free of the bureaucracy of larger businesses.

Browsing deals on Acquire.com, Chan stumbled upon a business earning $8,000 a month helping teachers grade essays using AI. He saw a product with traction selling to a demographic he knew intimately and bought in. Read our story on how Chan grew Essaygrader from 400 to 100,000 users here. We hope it inspires you to do something similar.

Start Small and Work Your Way up

The same wisdom applies to building companies as it does to acquiring them. Your first few won’t do that well, but later on, when you’ve learned from your mistakes, they’ll do much better. The same is true of acquisitions.

Start small until you’re comfortable with the acquisition process. Smaller businesses require less capital, reducing risk and leaving you with more funds to play with post-acquisition. It’s easier to recover from a failed acquisition at $20,000, for example, than one at $200,000. 

Before your first acquisition, you’re a rookie prone to mistakes. But once you’ve dealt with LOIs, due diligence, negotiations, and so on, you’re a veteran capable of acquiring bigger startups without getting lost in the process. You can then pounce on opportunities your “greener” peers might’ve missed.

A real-world example:

Back in 2022, we had the fortune of interviewing founder Daniel Chu right after he’d bought his startup, Emojics, on Acquire.com for five figures. While we haven’t followed up, it seems he has since sold off the domain to another business. Listen to his thought process behind buying Emojics on Acquire. 

Keep It Simple

Your first acquisition should be simple, too – an easy fit for your current expertise. What are you capable of now? Your chances of a return on investment dwindle when you have to learn new skills, declutter your schedule, or hire new teams. 

Your first acquisition is tricky enough without adding a sprawling, labor-intensive technical product or service you may know little about. Even if you possess the right skillset, give yourself time to understand the acquisition process. The simpler the startup, the easier it is to transfer ownership, leaving you more time for post-acquisition planning.
Want to know more about what kinds of businesses attract strategic buyers? Check out the article we wrote on that

Be Patient Until You Find the Right Business

Knowing what you want is vital if you want to acquire the right business. The more specific you are, the less likely you are to be surprised or disappointed. Don’t rush into acquiring a startup just because it’s got an attractive ARR, asking price, or tech stack. Think about size, product, market, customer acquisition strategies, and so on. 

When you need a new outfit, you don’t walk into a store and grab the first clothes you see. Instead, you browse by color, style, and fit. If you find the right match, you buy, you walk away empty-handed. The same applies to acquisitions: don’t acquire until you find the right fit – even if it means walking away from otherwise attractive deals.

A real-world example:

We sat down with a serial startup buyer, Pascal Levy-Garboua, after his fifth acquisition on Acquire to hear a bit about what he looks for in an acquisition. He told us he always looks at metrics like:

• High levels of inbound traffic
• Growth
• Ability to 2x growth in 2 years
• Good rapport with the seller

Check out the rest of his podcast here.

Choose a Business in Which You Can Make a Difference

Think of a startup as a jigsaw puzzle missing its last piece. Do your strengths align with the business? Does your expertise fill any gaps? Your skill set should be the key to unlocking growth, which means choosing a startup that dovetails with your experience.

For example, you might be a fantastic marketer but have zero coding experience. It would make more sense, therefore, to acquire a business that either needs a marketer or sells a marketing product than one that needs technical expertise or to communicate in developers’ language.

That’s not to say you can’t acquire a company for other reasons, but it’ll be harder to generate a return on investment. You might think, “Oh, I’ll just hire an operator to run the business,” but this adds complexity (keep it simple, remember?), and no operator in the world is a substitute for you being able to roll up your sleeves and do the work.

A real-world example:

In 2026, we interviewed one serial founder (and acquirer), Zach Simmons, when he’d recently bought a property assessment SaaS called Appraiva. He chose his acquisition primarily  because:

• He liked the team
• The app was hard to copy
• He had experience in other verticals in which he could adapt his app.

Zach regularly acquires businesses, and he gave quite a few good tips for buyers that you can listen to here.

Does the Acquisition Help Achieve Your Goals?

You’re an entrepreneur with an exciting career ahead of you. What’s the plan? What do you want to achieve in the next five years? The next ten? Your goals dictate which startups to acquire, but have you seriously thought about them? 

You might want to operate a number of smaller startups or acquire and sell them one at a time. Or perhaps you’ll assemble a new product or service from several Acquired technologies. You might also acquire missing expertise or customers in new markets. It all depends on you. 

If you want your first acquisition to move you closer to achieving your goals, which it should, think carefully about the size, type, and industry of the business. Otherwise, you might find you take a step backward or sideways, delaying your ambitions. 

Many successful buyers, for example, end up making acquisitions because it lets them enter the world of remote work quickly, freeing up time for things like taking care of a newborn.

A real-world example:

In 2026, we interviewed entrepreneur Joel Graber after he’d recently purchased a small design agency on Acquire, even though he already had a successful growth marketing agency.

Why did he do it?

While his marketing agency saw decent success, he invariably hit a bottleneck when his clients asked for design work, and he had to refer them to other agencies. With a design agency in his belt, he was able to grow both his own marketing agency and use his growth agency to get more clients for his design agency. It was a twofold success.

Read our article to find out more about what Joel looked for in his agency acquisition, like EBITDA and time in the market.

What’s Expected of You Post-Acquisition?

Acquiring companies is hard work. You must win the loyalty and trust of employees, customers, suppliers, and partners. Just keeping everyone happy and motivated post-acquisition is a job in itself, and you’ll certainly experience some uncomfortable conversations. This is on top of any growth strategies you have in mind to generate a return on investment. 

Spinning all these different plates can be a strain on the mind and body. But it’ll be worse if you haven’t understood what’s required of you post-acquisition. Will you enjoy the work? Will you get along with the people? Are you ready to field challenging questions on your plans for the business? Once you can say “yes” to these questions, you’re ready to Acquire. 

Learn More About Buying Startups on Acquire

Still not entirely sure how to choose a good startup to acquire? Not to worry, we’ve got links to a couple of different webinars we’ve created, helping buyers like you pick the business that will change their future.

• Entrepreneurship Through Acquisition: Why Buy Rather Than Build?
• An Expert’s Guide to Buying Your First Business
• An Acquire.com Guide to Buying the Best Startups

Are you ready to buy? Sign up for your free buyer account and start browsing listings from hundreds of sellers.

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When you’re ready to pull the trigger, you can upgrade your account to paid to see more data and start chatting with founders. We’ll give you a full refund if you cancel your account within the first seven days.

Happy hunting!