What it's really like selling your business

note - this was originally posted on my LinkedIn April 21, 2026

Five years ago I felt on top of the world. I’d taken a big risk in leaving my corporate job, and it was paying off handsomely.

With RORA I felt like I'd found the perfect business model and perfect role for myself. I was like the maverick of accounting. Solving old problems with new solutions that weren’t supposed to work and somehow carrying it off. Each less logical and somehow more successful than the one before.

I felt like Bradley Cooper’s character in Limitless. When I was in a corporate I was only using 10% of my brain. Now, running a startup, I could see in colour for the first time. Everything I touched turned to gold.

Then, one day, it stopped.

Staring into the chasm

For the first few years, things were going great. Our fractional finance team model felt like it came at the perfect time for the market. We were doubling in size every year. We grew our team from 1 to 20 really great people within 24 months.

Then in 2021 we got hit by some headwinds.

• The VC market slowed down, and our competition caught up

• My cofounder stepped away, and needed to be bought out

• We reached a scale where all of our systems started to break

Elon Musk famously said running a startup is like chewing glass. I realised that he was actually right about something.

Overnight, my dream role turned into a firefighting nightmare. I went from doing whatever I wanted each day, to a packed schedule of firefighting and papering over cracks. But there was never enough time or margin to properly fix anything. The gap between what I was accountable for and what I could control felt like a chasm I could never escape.

I developed a constant hyper-vigilance and anxiety - where was the next disaster going to come from?

I knew that some of my team was working really hard. But sometimes it felt like some others were happily playing running a startup.

“Don’t worry about those problems Dan, they always seem to get solved!”

“Yeah because I stay up all night solving them (you lazy bastards)” I wanted to scream.

For a time I was stuck here, feeling totally confused. For a long time my response was ‘just try harder’. I worked harder and harder but nothing seemed to change. Instead I got more of the same.

Finding a way through

After a lot of burnout and false starts, I realised we needed a totally different approach.

In order to get back to doing what I loved, I had to build the best operating system a people-based business had ever seen. I had to destroy the role I’d built myself and replace it with a machine that worked without me.

I always like to overreact to problems, so we tackled this one by having no fewer than four COOs.

1. Me, designing the new process and overseeing the new hires

2. A COO coach, guiding us on the journey with occasionally outlandish suggestions from her time working with unlimited VC money

3. The actual COO, learning to operate and codesign the system whilst patiently submitting to massive micromanagement

4. Our Head of Operations, who quietly ran the business in the background whilst I distracted everyone else

There were setbacks. I put my trust in several hires that didn’t work out. Each one exhausted me.

Eventually it felt like time to step back. Both to recharge and to see what the system was capable of. To really evaluate how it was working, I needed to remove myself from the picture altogether. It was a scary move and I feared the worst.

Disaster, or relief

I was pretty terrified at first. Trying not to check Slack I imagined the messages that were no doubt piling up. ‘Dan, its all going wrong, our clients hate us, please come back!’

But instead, when I checked in I found something unexpected.

Things didn’t get worse. If anything they got quietly better.

We’d reached an inflection point. Before we didn’t have good systems, so problems got solved by sheer effort and force of will. Now things seemed to be clicking into place. Everyone knew what steps in the process they were responsible for and when they had to be done by.

In fact the only problem we had was one I hadn’t seen coming. We had too many COOs. There was some duplication of effort. In contrast to what went before, this was a delightfully easy problem to solve.

Removing myself and the COO coach meant that my COO could step into my role and our Head of Operations could step into COO territory.

Back to basics

With childish glee, I realised I could finally get back to what I loved. Doing crazy unexpected initiatives that somehow made us loads of money.

Except, I couldn’t. The time off had shown me something.

What I wanted from the business and what the business wanted from were no longer the same thing. RORA didn’t need a slightly crazy maverick. It needed stable, consistent management.

I dragged the team to Milton Keynes (business capital of the UK) for a strategy session and took myself out of the equation fully.

What would the ideal strategy look like for RORA if I wasn’t involved at all?

It didn’t look like crazy new initiatives. In fact, it looked a lot more predictable. Building the essential (but boring) compliance services that our clients kept asking for.

And so, I started building a compliance division myself But I think we all knew my heart wasn’t in it.

At that point, a potential acquirer came along with an offer to buy our business. They had an impeccable track record of delivering those exact services and a funnel of new opportunities for RORA. The logic clicked very quickly.

Breaking up

After many months of back and forth, the deal was done. I went into London in February to break the news to the team.

Everyone was equal parts surprised, apprehensive, and excited.

Tthat is, everyone except for me. With all the focus on what these changes meant for the team, there was a quiet footnote:

“This is my last day. Goodbye.”

There was no cake, and I made no grand speech. I just... quietly slipped away.

The human side

“Congratulations on selling your business, you must be so happy!”

I hear a version of that a couple of times a week.

But honestly, happiness isn’t the main feeling. It’s much more complicated.

I didn’t sell because that was always the plan. I sold because I had changed, and because my business had changed. We were no longer right for each other.

It’s a classic breakup.*

A breakup with something I loved. A breakup with the future I’d imagined for myself.

When you see a founder who looks less happy than you’d expect with their exit, maybe this is why. Because in real life, endings usually aren’t happy. They’re complicated and bittersweet.

But through the pain, you evolve and grow. The loss of one future clears space for you to become the next version of yourself.

So it's not happiness, no. But there is definitely a sense of satisfaction. I’m proud that I took risks, did work that I cared about with people that I loved, and made money doing it.

I embraced the challenge, took a battering but I came out with my head held high.

*Although admittedly, receiving lots of money as a sweetener does help the breakup blues. I wish some previous girlfriends who dumped me had tried this.