What founders say is the hardest part of selling their business

We’ve interviewed nearly 300 founders who’ve sold, and this comes up most often as the biggest challenge. Is it what you'd expect?

Alexis Grant

December 18, 2025

Biggest challenge when you sell? Due diligence.

Episode Length: 6 minutes

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When we ask founders what surprised them most when selling their companies, their answers rarely match what most people assume about acquisitions.

It’s almost never the negotiation, the LOI, or even finding the right buyer. Instead, nearly every founder points to the same stage as the hardest part of the entire process: due diligence.

For many, diligence becomes a second full-time job — one that has to be done while still running the business and keeping performance strong.

It’s also where buyers ask for documentation most founders have never needed before, from financial detail to operations, team structure, and even lists of tools and plugins.

Here’s what founders who’ve sold wish they’d known sooner.

What you’ll learn:

What buyers really look for once the LOI is signed
Why this phase can unexpectedly impact revenue
How founders can delegate and prepare before entering this stage
Steps sellers take to make the process smoother and faster

Plus, a resource for due diligence preparation

Curious what your buyer might ask for during due diligence? Download our due diligence checklist (it’s free) and get prepared.

Transcript

We’ve interviewed nearly 300 founders who’ve sold, and this comes up most often as the biggest challenge.

We’re interviewed nearly 300 founders now, and we ask every single one:

What was the biggest challenge when you sold your business?

Now, I think if we all guessed what this was, we’d guess things like… finding the right buyer, or maybe negotiating the deal… but those pieces rarely get mentioned.

Hands down, the challenge that comes up the most often, is due diligence.

Founders almost always say the due diligence phase was far more work than they expected.

Due diligence happens after you and the buyer sign an LOI, or a Letter of Intent, which outlines their intent to buy the business, as well as many of the details that would go into that transaction.

Now the buyer gets to look under the hood. So they’re checking out all aspects of your business, to see that it matches what you’d promised, and to get a real feel for this company that they’re hoping to acquire.

They will want to see your processes for doing the work, your detailed financials, eventually your client list and team makeup… everything that makes your business tick.

There are two reasons why due diligence ends up being harder than most founders expect.

The first is because buyers often ask for far more documentation than founders have kept.

We saw a simple example of this in the story we wrote about Packhacker, a content site. The founder, Tom, said his buyer asked for a list of all software packages and plugins they used, and it took him an entire weekend to put it together.

Buyers will ask about things you never would’ve thought of. And if you’re selling to a public company, diligence can be even more intense.

The second reason DD can be really hard, is because you have to maintain the performance of your business at the same time.

Imagine diligence becomes a full-time job, which is common, ON TOP of your full-time job as CEO of the company.

You really need to focus on keeping the company moving in the right direction, so performance doesn’t slip during diligence, as that could affect the terms of your deal. But diligence also requires a lot of your focus. So many founders say it’s like having two full-time jobs.

We wrote a story recently about a founder who said he KNEW diligence would be hard work, but he just did not account for how much time he would lose to it – and that took away from the sales he usually brought in, which ended up having a negative impact on business revenue.

So I think knowing this, knowing that due diligence might require a lot of effort, is really the best way to prepare for it. You don’t want to be caught off guard.

But there are a few specific things we’ve seen founders do, that will help you navigate the due diligence process.

First, delegate as much of your day-to-day as possible AHEAD OF TIME, free up your plate. Build in some space, so you’re not already at 90% or 100% capacity when you go into diligence.

This has the added benefit of making the business less reliant on you as the founder, which is always appealing to a buyer as well.

If you have a co-founder, sometimes we see one co-founder focuses on diligence, while the other keeps the business running smoothly; that’s a great way to break up responsibilities as well.

Or, you could bring in another team member to help with diligence. This can be tricky, depending on when you plan on letting your team know about the sale, but if you have a trusted team member who can help, that goes a long way.

And then, get your house in order early. Sure, there will always be documents you hadn’t thought to compile.

But if you cover your bases on the easy stuff – make sure your financials are in good shape, for example, and that you have all your client and employee contracts in order – that means you’ll have more time to focus on unexpected asks.

Finally, collaborate with an M&A advisor early – between 6 months and up to even a year in advance. Work WITH them to prepare the business. This is why you hire an advisor or a broker, this is their job, to prepare you. They’ll help you think about what a buyer might ask for, for your type of business, so you have more of your ducks in a row when it’s time to sell.

OK, so knowing this, you’re not going to be surprised about any curve balls that come at you during diligence, right?

And maybe, as you work toward your sale, you can look to make improvements now, that will make diligence down the road, just a little bit easier.

Thanks for joining us, and we’ll see you next time.