Short Answer

No.

Long Answer

It’s complicated. Let’s dive deeper.

How is my life different

If I had taken up a job after B-school, I would have joined either a non-McKinsey, non-BCG consulting company or an investment bank on the back of my strong arithmetic skills. I would have made the switch to a growth stage startup in 5 years. I would have taken a VP, Strategy / Chief of Staff role. Most importantly, I would have made around INR 6 Cr in gross salary and would have had savings of ~4 Cr.

Instead, I worked on a non-tech Education startup for 4.5 years and a tech heavy Education startup for 3 years. The first one is still operational, but I barely made any money from it—less than 10% of what I would have made as Salary over those 4.5 years. I stepped out operationally, but my co-founder still runs it. I raised some money for the second one which ran out before we could find product-market fit. While looking for an exit, an entrepreneur made me a job offer to join his company as CEO. I have been moderately successful in that role and the startup is worth ~3x of what it was when I joined a little less than 3 years ago. (It was flat for 2 years before I joined). I make good money in this role, which is lower (but not by that much) than what I would have made in a more conventional role for someone who followed my path.

The money

I am worth less than 20% of what my peers are worth. I was in the top 15% of my batch at IIM Ahmedabad. People with similar profiles make lots of money. However, I make enough money that it is not a reason for any of my lifestyle decisions (e.g. home I stay in, city I live in, places I vacation etc.). While I am not rich, you wouldn’t call me a failure (you could, but my wife doesn’t, so it’s fine).

The career

I really enjoy what I do, and as an entrepreneur (and now as a CEO), I have reasonably deep expertise across many domains - tech, marketing, sales, design, product, training, teaching. I really am a generalist. I have had deep exposure to business having been in the arena. Unless you’re the guy calling the shots, it’s really difficult to understand the challenges of building a business (note, I did not say start-up or company). This makes me more valuable for higher profile/high pressure roles like CEO, Business Head, P&L Leader, Head of Growth. To be honest though, I have not gone deep into the interview process of many of these roles as a result of my lack of extra-ordinary success until recently.

However, on the flip side, my experience in a particular domain (e.g. product/marketing) is not as deep as my peers. As a result, I am not a good fit for a lot of conventional roles which fit my level of seniority. If someone is hiring a VP, Product, they would look for someone who has been a product manager for many, many years. That doesn’t mean that I don’t get offered those roles. I do, but not at top tier companies and the compensation is lower than what my peers make. I have been offered roles across a wide gamut of areas - product, marketing, strategy and funnily enough - engineering despite not possessing many hard skills. These roles are also more abundant in number.

This “generalist penalty” hits hardest when looking at opportunities abroad. Standard expat hiring paths favor deep specialists—companies sponsor visas for Senior Engineers or Investment Bankers, not for “guys who are pretty good at everything but master of none.” While my peers move to EU, Canada or Dubai with relative ease, my unconventional background makes that transition incredibly difficult. I am effectively geographically locked unless I take a massive step down in seniority, which I am too deeply invested in my current role to do.

Miscellaneous challenges

The final struggle is less about what I do, and more about who I am. I might not derive my identity from my religion, but my country has gotten more polarized than ever, and an average person ascribes my identity to my religion anyway.

There are regular moments where people make me feel lesser because of my last name. People I respect have not removed themselves from WhatsApp groups where ugly things are amplified. This is why I even bother about the “generalist penalty”

Would I make the same choices again?

If I knew the outcomes beforehand, definitely no. This question is hard to answer since no one can travel back in time. However, I didn’t know the outcomes going in, so I don’t regret my decision at all. I do know that I wanted to build something important, and if I hadn’t tried, I would have 100% regretted it.

Should you build something right out of college?

Yes, if you’re high agency enough to take advantage of the new LLM technologies which could effectively 10x your output.