Connor Willoughby
Independent investor, builder and writer
United Kingdom
1 August 2026
An open letter
This is where I stop pretending to be the future version of myself.
A personal letter about identity, ambition, money, mistakes and the decision to build honestly from where I am today.
To anyone who has ever wondered who Connor Willoughby is,
To whom it may concern,
If you have arrived here wondering who Connor Willoughby is, then you have asked the same question I have been asking myself for years.
A name on its own tells you very little. Until you understand a person’s history, ambitions, mistakes and fears, they can feel like anybody else: another unfamiliar name with no real meaning attached to it.
For a long time, I worried that Connor Willoughby meant nothing.
I looked at successful founders, investors and entrepreneurs and wondered how their names became associated with achievement. I admired people who had built remarkable companies, managed enormous portfolios or created products used by millions.
Without fully realising it, I began presenting the person I hoped to become rather than the person I actually was.
I did not do that because I wanted to deceive or manipulate anyone. I did it because I struggled to believe that the person I was at the beginning was worthy of being seen.
I thought that if I appeared successful enough, perhaps I would eventually become successful.
The truth behind the image
I was diagnosed with Asperger’s syndrome in 2009. It has influenced how intensely I pursue my interests and how vividly I imagine the future. When I become interested in investing, technology, space, photography or building websites, I rarely engage with it casually. I immerse myself in it.
At times, I have become so focused on the person I might become that I have lost sight of where I actually am.
Since I was eighteen, I have lived with debt. I have received more than 120 debt collection letters. I am not proud of that. It affected how I saw money, success and my own worth, and at times it felt like descending a staircase with no obvious end.
While other people might spend their money on holidays, hobbies or possessions, I often spent mine chasing the next idea: a company, a device, a project or a possibility that I hoped might change the direction of my life.
The uncomfortable truth is that I sometimes confused ambition with appearance.
Buying the appearance of success
Comparison has influenced some of my worst financial decisions. If I heard that somebody was getting a new phone, computer or other expensive device, I could feel an immediate urge to have it too, or even to have it first.
I did not always know whether they were buying theirs outright. I only knew that I had signed another contract, despite already owning devices that worked and despite not genuinely needing the new one.
I was not really buying the product. I was buying the feeling of appearing rich.
Today, my investment portfolio is worth just under £1,500. It is not a multi-billion-pound portfolio, an institutional fund or a vast financial empire. It is a small personal portfolio belonging to somebody who enjoys investing, remains inexperienced in many areas and is still learning.
I want that truth to be visible. If the portfolio grows substantially in the future, I want people to be able to see where it honestly began.
Compassion and financial vulnerability
Money is also an area in which I can be emotionally vulnerable. When I see somebody who appears homeless or distressed, my instinct is to help. I have given food, drinks and support to people whose circumstances I later had reason to doubt.
Those experiences were disappointing, but I do not want them to erase my compassion. I would rather occasionally help somebody whose story was not genuine than become so cynical that I ignore somebody who truly needs kindness.
I am also learning that compassion needs boundaries. Helping another person should not mean repeatedly placing myself in financial difficulty.
My instinct to take control
I have recognised that I sometimes rush to solve other people’s problems before asking whether they want my help.
When my mum needed a new phone, I bought one without properly involving her in the decision. When my brother wanted a PlayStation 5 for Christmas, I arranged finance through O2 instead of listening to my mum and allowing her to manage the situation in her own way.
My intention was to help, but good intentions do not remove consequences. By acting first, I sometimes removed other people’s opportunity to make their own choices while adding another financial commitment to my life.
I am learning that leadership is not the same as taking over. Sometimes helping means listening. Sometimes it means waiting. Sometimes it means accepting that the decision is not mine to make.
Building an identity of my own
I admire founders, investors, writers and builders whose work has become associated with their names. For too long, however, I tried to borrow the appearance of other people’s success instead of developing an identity of my own.
I do not yet have a grand answer to the question, “Who is Connor Willoughby?”
I am not a billionaire. I do not manage a vast fund. I do not have decades of celebrated achievements behind me.
I am interested in markets, technology, space, public affairs, sustainability, education and design. I build websites. I invest modest sums. I write. I make mistakes. I sometimes act impulsively. I am trying to understand those patterns instead of disguising them.
That is why ConnorWilloughby.com is changing.
I no longer want this website to be a monument to an imagined future or a façade designed to make me look wealthier, more established or more important than I am. I want it to become an honest record of the work: the investments, projects, open letters, ideas, successes and failures.
I do not know whether I will ever build a company worth millions. I do not know whether my portfolio will become substantial. I do not know whether my name will become widely recognised.
What I do know is that I would rather people meet the real Connor Willoughby than a version carefully constructed to impress strangers.
This does not begin with wealth, influence or success. It begins with honesty.
Yours faithfully,
Connor Willoughby
connorwilloughby.com