- K
- Aug 16, 2024
- 5 min read
Updated: Nov 26, 2025
“All I ever wanted was the freedom to make my own mistakes.” - Mance Rayder [1]
Chasing a pipe dream.
Years back when we entered the advisory business, we had a whole bunch of M&A and capital raising deals. It was thrusted on to our plate by someone who claimed to know important people from all over the world.
On our plate were companies looking to raise capital or those trying to get into new markets, early stage start ups looking for venture funding, or investors who were simply trying to put capital to work. It was a buffet of deals.
We had spent a considerable effort evaluating each and every one of them. Most times it involved a systematic way of filtering and deciding whether or not to proceed. Other times we ended up having to do 'favours' such as meeting brokers of the deal as part of the process, sitting mindlessly in a lecture for days. When ever we hit an impasse, felt it wasn't cost-effective or disagreed with going ahead, someone would say:
"When starting up, sometimes you just have to do the things that you don't like to do."
But our deal pipeline had been so full - full of long shots and losers. Projects that had a low probability of closing, clients that likely couldn't pay, or simply just a waste of our time. Listening to our "elders and betters", we almost never had any decision-making authority to kill the deal or proceed with what we felt made more commercial sense.
It was probably only over a year later that I had begun to realize the ironic and toxic dumbness of it all:
The idea of starting up had been ours, us bearing our own costs, but somehow suffocating under a blind workload, executing a totally different agenda that belonged to someone else, just to heed conventional wisdom, that it was part of the entrepreneurial journey, and we had to "do the things that we didn't like to do."
A lesson about vulnerability.
I couldn't remember exactly when it started to dawn on me, but one day amidst the frenzy of calls and meetings, I woke up, subconsciously dragging my feet out of the house and feeling that morning anxiety of arriving at the office before 9:30am.
I was also checking my emails and text messages in the same way I used to check my Blackberry on a Friday evening (yes we used Blackberry in those days), hoping that you don’t get a nasty email from the ‘boss’ to turn round a slide deck by Monday.
And in any job, the moment you start counting down to Fridays or dread Monday mornings, you are basically f****d.
Back then I had been ‘working’ on several leads. I had no full context to these projects, no direct connection to the source, no tangible resources to mobilise.
Perhaps, more importantly, no autonomy in dictating any of the commercial terms. It wasn’t even a client that I originated. I was stuffed to the neck with work that wasn't mine and was simply churning slides and spreadsheeting numbers.
At every discussion, I found myself mostly on the receiving end, listening to fluffy ideas and being fed with lofty dreams, all the while being told to follow up on execution in the background.
A lot of these didn't have any commercial mandates tied to it. It was basically a bunch of stuff that was done in goodwill, in the blind hope that would one day convert into a billion dollar opportunity. We were being played. And as the popular Chinese saying goes, I was being led by the nose.
In that whole process, I think no one had really considered what I wanted for myself.
It was a weird setting.
Why? Because my intention of starting a business was to unshackle myself from a corporate job, but I ended up in a situation whereby I was working on someone else’s projects and providing the ‘weekly reports’ on a regular basis.
Suddenly I was an employee all over again.
The reality of it hit me hard when I ran this through my head and played it out right till the very end: I was no longer the owner of my business, whatever form it had evolved into:
No say, no control, no money, no visibility, all of the downside and none of the upside.
That whole process taught me something:
In any moment of vulnerability, if you are not careful in protecting your dreams, someone else will show up and make you build their dreams for them.
Sometimes people turn to those who are more “successful” without really aware that everyone is simply just trying to validate their own narrative, and what works for them may not work for you.
Takeaways.
In any enterprise with more than one shareholder, it is almost inevitable that decision-making and relationship dynamics get relatively complex. Everyone brings a set of different resources to the table.
Some bring sweat, some bring relationships, some open doors, others bring influence. Regardless of no matter what you put into the pot, there are always some cardinal rules to abide by:
Integrity and transparency above and before economics, always.
Respect the money and capital i.e. everyone has the right to their opinion, but only those with skin in the game get to decide.
In any deadlock or impasse, refer to point number 2.
Whenever you feel that you are getting the short end of the stick, refer to point number 2.
If you find yourself doing the things that you don't like to do, refer to point number 2
Doing business can be complicated, but everything fundamentally defaults to point number 2.
You can bring up grey hairs and sweat from decades of experience, or show off selfie photos with the big shots. But none of that really matters until you put money on the table. That is all there is.
And so, I still remember the January of 2020 (just before COVID), when I was walking to my usual morning coffee hangout in Singapore around the neighborhood, while reflecting upon decisions that were made over the last four years.
On hindsight, I should have been panicking given the unnerving amount of cash in my bank account and thinking about what lies next. But even in those dark moments, I had found a quaint inner peace, taking responsibility of all the good and bad decisions that were made.
It was a liberating feeling of sorts.
Perhaps all I really wanted out from starting a business was the freedom to do what I wanted, including the freedom to make my own mistakes.
[1] Adapted from Mance Rayder, leader of the free folk, from the HBO series "Game of Thrones"