Quitting is for Winners. And So is Starting Over.
This tech outsider ditched his ad job to found a startup, only to leave it and learn to code — eventually consulting for tech’s giants.
Suraj Kapoor is one of those product leaders that, well, you just can’t define — he’s a jack-of-all trades. Leaps of faith define his journey: from advertising exec, to co-founder of a company that didn’t make it, to coding bootcamp (while living on a couch), to junior engineer at a VC, to Product Director at WayUp, to a short burn out stint in Indonesia teaching yoga, to where he is now — in London, working for himself, helping product mangers build better products. Check out the top 4 insights from our interview with Suraj.
Insight 1: Do things that give you energy.
“I was working in advertising at the time — that was my first profession after college — and I never really loved what I did. It took me a bit of time to realize that inside me, there was an entrepreneur.
I think it just goes back to to to doing the things that give you energy in life — that’s kind of how I frame it in retrospect. We all have had that job where we get up and we just don’t want to go to work, and that’s just not a way to live for me. And I felt like that, just to be very candid.
Just the idea of creating an entity, an organization, that could provide value for other people was just an exciting journey. I really liked the idea of doing something unknown, even if it could result in failure — I’m impulsive like that.
I met a co-founder, and we started a company together building an online fashion company — and it was a four year journey of just trying to build a company. And yeah, as soon as I started it, it was such a big challenge, but I loved it there. It was so much harder, and obviously I had no money, living in New York on a couch. But I just loved it I didn’t care. And that to me was was a sign, you know, I was working twice the hours, getting paid less than half the money. But I enjoyed every minute of it. It brought me energy.”
Insight 2: Always ask, “Is this working for me?”
“I think one of the biggest mistakes that I made was that I spent too much time building my company before realizing, “this isn’t working for me.”
After building my company for four years, I kind of took a step back and admitted to myself for the first time that things weren’t working. One of my challenges was that I didn’t know how to code — very problematic at the early stage of a tech company.
As soon as I admitted to myself, that this wasn’t working, I took a break from my company and learned how to code. Everything started to make sense. It felt so immensely powerful to me to be able to program —like I could unlock so many doors. I enjoyed waking up. I enjoyed building random apps, just to see if I could build them. And I was again, spending 12 to 14 hours just doing stuff I loved.
There are two different conversations that are happening in our heads. Conversation 1: “This is stupid — this is not rational. What are you gonna do, leave a company that has investment? And you’re just gonna start a new career as an engineer?” Conversation 2: “Life is a journey and it’s part of your duty to embrace that.”
Whatever you do has a cost. You may not realize the costs vs. the benefits at that point. But in retrospect, the end benefit could be much larger than you could’ve even imagined. For me, it was.
So sure the cost at that point of dropping my company and becoming an engineer was a lot, but I think in retrospect it was a lot less because the benefit of learning to be an engineer was much larger than I could have even imagined. So that that’s just another way to look at things.”
Insight 3: Know your story. Tell it. Even the vulnerable parts.
“To land clients, you need to sell yourself — what’s your story? And before you can sell it, you have to realize you have a one in the first place. You need to know yourself and know how to package your experiences and skills into a story. If you’re an amazing engineer or you’re product person, and you have all these amazing skills — figure out how to package them up and put them in front of people and talk about them.
I didn’t realize I had a story — I felt like a jack-of-all-trades until I started being asked about my professional experiences and then I realized, “Actually, I have a story, I just didn’t realize that it was valuable because I didn’t know how to package it.
Part of having a good story is being genuine. Authenticity — I believe that to be true in life, just as much as in work. And vulnerability is an important part of that. Throughout our journeys, we’ve all learned, and we’ve made mistakes. And the vulnerable parts of your story are just as important as the strengths. To be able to talk about your failures from a position of learning from them and conquering them is a strength, not a weakness.
Be transparent about those vulnerabilities — how you grow, how you learn, how you feel. I think that’s relatable, it’s how we connect to one another as human beings. And I think it’s a good way to sell your story. And yourself.
Insight 4: Want to know someones values? Ask them why they built their product.
“You know, when you ask a company why they built what they’ve built, it is a very telling way of learning what their values are. It can be a whole range of things but you know — I find myself now gravitating towards companies that have a very strong social angle because of what’s happening today.
And they’re more of those companies out there — those companies are going to start attracting more and more talent because of values. And if you’re a company and you don’t have values, or you haven’t thought about them, or they’re not important to you — you’re going to start losing power. It won’t happen immediately but it’s going to happen over time.
To that point, values shouldn’t be treated as a strategy —they should be treated as a right for a company. Because you know, companies have seen as ways to make money, but they have a social role, and I think we are starting to realize it.
It’s important that any company that is being born or is existing right now really truly deeply thinks about how do they want to represent themselves, in a holistic sense. You look at a product, you look at the hiring process, you look at the employees that are working a company — there are so many signs as to what the value is and if it will continue.”
Like what you read?
If you like topics like these and hearing from modern independents like Suraj, join the A.Team community & future events by applying here! And if you’d like to to hear more from Suraj, check out his reading club, Pointer — it’s geared toward developers, offering a window into what other current and future CTOs are reading and thinking about.
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