Entrepreneurship is often romanticized as a straight path to wealth and freedom. Build something valuable, sell it, and make a lot of money. But what most people fail to talk about is what happens after the sale.

In a LinkedIn post, serial entrepreneur and philanthropist Simon Squibb opened up about the moment “after” selling his dream, and it is not exactly a picture of happily ever after that most people envision.

Rather, it reveals a deep truth about the lesser known side of entrepreneurship, the emotional and psychological upheaval that comes after selling your company.

Here is a reflection from Simon Squibb as seen on his LinkedIn page;

“Selling my company was supposed to be the best moment of my life.

It wasn’t.

After I sold my company, I did exactly what you think I’d do.

I bought a Porsche. A big house. A personal trainer five days a week.

And for the first time in my life, I was spending money on me instead of pouring it back into the business.

I thought I’d made it. All the years of hard work and risk, had been for this.

But something felt off.

For two years I drifted, I played golf, ate at nice places. And was spending more and more money to try and feel less empty.

I was only in my early 40s but had no real reason to wake up early anymore.

I’d realised, that when I was poor, I was a lot happier.

Not because having money made me unhappy. But because I’d sacrificed it for my purpose.

Money doesn’t bring happiness. It brings options. And if you don’t already have purpose, those options just amplify the emptiness.

So I sold the Porsche and stopped all the meaningless spending.

Now if I buy something, it’s because it means something.

I try and live like I’m poor and I’m happier that way. And before I die, I will give all my money away.

Purpose first. Money second.

That’s the way to a happy life.”

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At first glance, this may seem like just another post from a billionaire. But look closer, it contains a set of lessons that many founders only learn after years of chasing success. Here’s a breakdown of the key lessons from the post.

1. The Moment Many Founders Dream About

For entrepreneurs, selling a company is often imagined as the peak of the journey. It represents validation, security, and the reward for years of uncertainty. Friends congratulate you, the numbers look impressive, and from the outside it appears like you’ve won.

But Squibb’s experience highlights something rarely discussed: the moment you remove the mission from your life, you also remove the structure that gave your days meaning.While building a company, life revolves around solving problems. You wake up with urgency. Decisions matter. Progress is visible. Even the stress has a purpose.

Once that disappears, freedom can feel less like victory and more like drift.

2. Purpose Matters More Than Comfort

Here is another line founders should ponder on: he realized he was happier when he had less money. That statement isn’t really about poverty. It’s about purpose.

During the early stages of building something, every effort is tied to a goal. Sacrifice makes sense. Long hours feel justified because they move something forward. That sense of forward motion gives life energy. Without it, comfort alone rarely satisfies.

This is a pattern many founders eventually recognize. The struggle that once felt exhausting turns out to have been the very thing that made life engaging. Purpose creates momentum. Comfort does not.

3. The Difference between Money and Meaning

Another insight hidden in Squibb’s reflection is the difference between money and meaning. Money can remove limitations and open doors, but it cannot decide which door is worth walking through. That responsibility still belongs to the individual.

When someone already knows what they care about, financial success can amplify their impact. But when direction is missing, more options can actually make the emptiness louder. In that sense, money behaves less like a solution and more like a magnifier.

It expands whatever already exists in a person’s life. For founders, this realization is important because many believe success will eventually answer deeper questions about purpose. In reality, those questions usually need answers long before success arrives.

4. The Lifestyle Illusion

The period Squibb describes - buying expensive things and trying to enjoy the rewards - is also familiar to many people who achieve sudden financial success.

At first, the upgrades feel exciting. But human psychology adapts quickly. What once felt extraordinary becomes normal, and the emotional return from new purchases shrinks over time. When fulfillment is missing, spending can quietly turn into an attempt to recreate excitement.

Eventually Squibb stepped away from that pattern, simplifying his life again. That decision reflects a lesson experienced founders often discover: possessions rarely replace purpose. They can enhance life, but they cannot define it.

5. Living With the Same Mindset That Built Success

His decision to “live like he’s poor” is really about maintaining the mindset that existed before the exit. Scarcity forces clarity. When resources are limited, people focus on what truly matters. They think carefully about how they spend their time, energy, and money.

Success can blur that clarity if someone isn’t intentional. Many seasoned entrepreneurs eventually realize that keeping a simple lifestyle helps protect the habits and perspective that made them successful in the first place. It keeps attention on building, learning, and contributing rather than simply consuming.

6. Redefining What Winning Looks Like

The deeper message behind Squibb’s post is not that money is bad or success is disappointing. Instead, it challenges the idea that financial achievement alone is enough to create a meaningful life. Entrepreneurship is fulfilling largely because it gives people something to build, something to improve, and something to care about deeply.

Remove that, and even success can feel incomplete. That’s why his final statement - purpose first, money second - resonates with so many founders. It flips the usual order of priorities. Money becomes a tool rather than the destination.

A Lesson Worth Learning Early

The irony in stories like this is that many entrepreneurs spend years chasing the exact outcome Squibb describes, believing fulfillment will appear on the other side of it. Yet the real insight is much simpler. The part of the journey that feels meaningful is often the building itself. The challenge. The progress. The mission.

Founders who understand this earlier tend to design their lives differently. They pursue ideas that matter to them, build teams around shared purpose, and measure success by more than financial results. And ironically, those are often the people who end up building the most valuable companies anyway.

Because when purpose drives the work, success becomes a byproduct, not the only reason for starting.

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Read - The Dark Side of Sudden Success: Why Founders Often Need Failure Before They Scale

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