Hi Krish,
Thanks so much for the question – I’m hugely in awe of what you’re doing at Chargebee, and I’ve always had a really positive experience every time I’ve met someone from the Chargebee team.
I could talk all day about things we’d do differently, but this question is great – what calls would I make the same if I could revisit them?
There are three really fundamental decisions we’ve made in the history of GoSquared, and each of them, if made differently would almost certainly mean the company wouldn’t exist today:
1. We started the company when we were still at school.
We didn’t know what we were doing. We knew NOTHING about running a company.
But we had an urge to create something, and to follow our hearts, and we went for it. Generally, in life, I have learnt to not regret taking action – the easiest decision is to postpone and delay and find excuses not to start something.
So I don’t regret for one minute that we started early, we made a ton of mistakes, and we grew a business from a young age. If we’d waited we would barely have been any wiser, but instead have wasted years in indecision.
2. We were had a critical decision to make when leaving school and heading off to university.
We were approached by angel investors with an offer. The condition was to drop out of university that we had barely started and build the business in London. 50% of everyone I spoke to said I’d be stupid to not go to university.
The other half of everyone said I’d be stupid to say no to the opportunity. I think my main conclusion is that everyone I kew thought I was stupid 
– ultimately, we made the jump. We didn’t particularly want investment, but we certainly wanted to grow the business and take it to the next level. I am so glad we did – if we hadn’t, I believe GoSquared would have fizzled out, and be a footnote of my life so far.
3. We were offered the opportunity to sell the company more recently, and we said no.
It was another extremely difficult decision to make, but one that we were honoured to have the opportunity to even consider answering.
It made us think long and hard about what we wanted GoSquared to be, and I truly believe the outcome has made GoSquared stronger and the team wiser. I couldn’t bare the idea of writing one of those clichéd blog posts announcing we’d be acquired, and that we’d be stronger than ever, only to see the company fade away and be forgotten.
I also don’t know if I’d make a good employee! I have no regrets about the decision we made to not sell – and that played a factor in our decision at the time – we didn’t want to look back for the rest of our lives and ask “what if we had stayed the course and built GoSquared by ourselves?”
I hope those are of interest, Krish. Happy to expand as much as I can on any of them if wanted.