1/ 14 Feb is special to me. My previous startup, Waylo got acquired on 14 Feb 2020.
Financially, it was a good outcome at 200X capital raised.
But, I was disappointed in myself and acted uncharacteristically.
Reminiscing thread + lessons learned.
Financially, it was a good outcome at 200X capital raised.
But, I was disappointed in myself and acted uncharacteristically.
Reminiscing thread + lessons learned.

2/ Strategically, it made sense for both companies....
The first half of the day and was mostly signing documents and code handover.
I resisted an insane urge to pull out when I lost admin access to our 500K+ lines of code and 90K+ prediction models.
The day had just begun.
The first half of the day and was mostly signing documents and code handover.
I resisted an insane urge to pull out when I lost admin access to our 500K+ lines of code and 90K+ prediction models.
The day had just begun.
3/ Waylo developed machine learning-powered price prediction algorithms for perishable inventory e.g. hotel rooms.
The key idea: if you need a fridge on Sep 1, what if you could get the Black Friday deal on Sep 1 instead of waiting until Thanksgiving?
https://medium.com/@kyunbit/attention-spans-are-getting-shorter-should-pricing-strategy-change-95536eab925
The key idea: if you need a fridge on Sep 1, what if you could get the Black Friday deal on Sep 1 instead of waiting until Thanksgiving?
https://medium.com/@kyunbit/attention-spans-are-getting-shorter-should-pricing-strategy-change-95536eab925
4/ Our vision was to bring retail pricing to the era of short attention spans.
It bothered me that our lofty ambitions may not materialize if we went through with the acquisition.
I knew I would fall way short of my goal of positively impacting the lives of 1 billion people.
It bothered me that our lofty ambitions may not materialize if we went through with the acquisition.
I knew I would fall way short of my goal of positively impacting the lives of 1 billion people.
5/ The wire transfer hit the bank account around 3PM. I had never seen so many digits in a bank account balance.
The account was in $1200 overdraft before the wire hit. I nonchalantly paid off the account payables, let the team, parents, wife know that the transfer was done.
The account was in $1200 overdraft before the wire hit. I nonchalantly paid off the account payables, let the team, parents, wife know that the transfer was done.
6/ As I walked back to my hostel, a strange feeling of despair hit me.
I loathed myself for being a sellout and taking up an acquisition offer before accomplishing our mission. The feeling grew intense and I felt I had to scream at myself. Couldn't do that in a hostel dorm.
I loathed myself for being a sellout and taking up an acquisition offer before accomplishing our mission. The feeling grew intense and I felt I had to scream at myself. Couldn't do that in a hostel dorm.
7/ I took a bus to the Barcelona beach and found a relatively secluded spot 10 mins from the iconic Westin and shouted at the top of my lungs.
It was more like a wail timed to mask the sound among the crashing waves.
It was cathartic, but I felt I had failed spectacularly.
It was more like a wail timed to mask the sound among the crashing waves.
It was cathartic, but I felt I had failed spectacularly.
8/ I wasn't done with self-cursing.
For the next 3 hours, I walked around the streets of Barcelona like a madman, shouting expletives at myself, punching one hand with the other, and whatnot.
I am ashamed of how I conducted myself that day. Won't ever happen again.
For the next 3 hours, I walked around the streets of Barcelona like a madman, shouting expletives at myself, punching one hand with the other, and whatnot.
I am ashamed of how I conducted myself that day. Won't ever happen again.
9/ I called up a few people and finally, @AdamDraper calmed me down.
Adam reminded me that I now had the financial freedom to pursue other ideas in future and very few startups even get to where we were. Adam has a way of helping you see the bigger picture. Forever grateful.
Adam reminded me that I now had the financial freedom to pursue other ideas in future and very few startups even get to where we were. Adam has a way of helping you see the bigger picture. Forever grateful.

11/ Over the last year, I have reflected on my actions last year as well as why I entertained the acquisition talks at all.
In hindsight, I am not sure we'd have survived COVID.
But the key reason, I believe was: I had completely neglected my personal well-being for 3+ years.
In hindsight, I am not sure we'd have survived COVID.
But the key reason, I believe was: I had completely neglected my personal well-being for 3+ years.
12/ I worked 100+ hours/week without salary for 4 years and was in ~$250K credit card debt.
I gave up all of my hobbies: traveling, hiking, photography, guitar. My wisdom teeth hurt, but I couldn't afford removal.
The vision kept me going, but I was tired and mentally drained.
I gave up all of my hobbies: traveling, hiking, photography, guitar. My wisdom teeth hurt, but I couldn't afford removal.
The vision kept me going, but I was tired and mentally drained.
13/ I still work long hours. But, I make sure to take care of myself.
My only splurge last year was a Peloton and I work out regularly. I realized, as a founder, I am a key asset of the company, and it is my fiduciary responsibility to take care of myself as well as the team.
My only splurge last year was a Peloton and I work out regularly. I realized, as a founder, I am a key asset of the company, and it is my fiduciary responsibility to take care of myself as well as the team.
14/ Lessons learned:
- Be mindful of founder (mental) health
- Take a break to collect your thoughts, if you can, before deciding on an acquisition offer
- The universe might throw a curveball e.g. COVID
- The line between success and failure is very, very thin
Hope this helps.
- Be mindful of founder (mental) health
- Take a break to collect your thoughts, if you can, before deciding on an acquisition offer
- The universe might throw a curveball e.g. COVID
- The line between success and failure is very, very thin
Hope this helps.
15/ Why am I publishing a deeply personal story of shortcomings?
Founder (mental) health is often overlooked. It seems you are expected to say "I'm crushing it". It's okay to be frustrated. It's okay to have down days.
It's a marathon and to win, you have to stop to hydrate.
Founder (mental) health is often overlooked. It seems you are expected to say "I'm crushing it". It's okay to be frustrated. It's okay to have down days.
It's a marathon and to win, you have to stop to hydrate.