How To F*ck Up & Overcome Depression As A University Student ft. TribalScale’s CEO Sheetal Jaitly

A student is the career-food-chain equivalent of a startup. One of the most obvious things we have in common with startups is our proneness to failure. Therefore it makes sense to gather wisdom from people in the trenches–startup CEOs and founders and leaders–in hopes of avoiding even just one of their mistakes.

I wanted to interview Sheetal, CEO of TribalScale (one of Toronto’s hottest tech startups), because I heard his team openly talks about their failures at work. That it’s part of their workplace culture to talk about screw-ups and lessons learned.

And if you can speak openly about your low points to your manager and teammates, what is failure then? I wanted to learn how to turn failure into a positive, and pass that lesson on to you guys.


This interview covers a lot of ground:

  • How to earn respect after failing at work
  • Sheetal’s rock-bottom-low point in university and how he climbed back up
  • How to be a boss
  • Why school isn’t for everybody
  • If you want to work at TribalScale as a co-op/intern, how you can get in and what you should know


If you don’t have the time to read:

Download this audio file instead. It’s a recording of the interview. Happy listening!


The Interview:

DI: Take us back to your YorkU days. Imagine you’re trying to build yourself up, and it’s not winning the same success you see your classmates achieving. What do you tell yourself?

SJ: Too many classmates chased prestige of the title and of working at big companies, or buying a bottle at a club and driving a nice car. But if I look at them now, they’re still in the same BS position they were in, and their pay grade went up maybe 10%. They’re pigeonholed where they are.

And then there’s Adam [TribalScale’s Marketing Manager who sat in on the interview—you’ll hear a bit of him in the recording]. He comes out of school, realizes he’s not growing as much as he wants to be at the current job he’s in. So he comes over and starts working with us. It’s not for his paycheque (I know how much he makes). But he works day and night because he’s learning. Fast forward 10 years and it’s Adam I’m writing the biggest cheque to, because he’s running his own firm. He’s gone and done the hard steps.

Hard work is hard work, there’s no substitute for that.

DI: How have you failed in your 20s?

SJ: I worked all the way through university and made really good money, so I thought my parents are stupid, everybody in this university is dumb, I figured out the world.

Harsh reality hit when the internet bubble burst in ’07 and I was laid off. I had someone who was very close to me, like an older brother, pass away. I went from being on top of the world to almost failing out of school, creating a mountain of debt, and feeling like I hit rock bottom and can’t get up.

DI: What was going through your head during the depression?

SJ: You hit this low as a student when you think you figured out the world and then it’s closed on you. That depression was crazy. I was spiralling.

I thought, I don’t know what to do. I can’t explain it. Tactically I was doing all the things—staying in my room, sleeping a lot, not leaving during the day, not being able to get up—that were the regular signs of depression.

DI: How’d you get out of that?

SJ: I remember my father coming to me and saying, “you haven’t shaved in a little while and you’re kind of moping around the house. This is not your personality. You’ve just gotta get out there. Get any job.”

So I took his advice, and decided that it’s not about the title or the paycheque, but it’s about going out there and finding my way and trusting that I would. Many times we look for the answer to the equation, but we don’t know what the variables are.

So I went back to the company that laid me off. I walked into the President’s office, and said “I need to get back in here. I’ll do it for free.”

DI: As a student feeling low like that, what can you do to get back up?

SJ: Look at time as the variable. It’s the one that you have. Don’t waste it not doing the Type A activities [things that you must get done that really matter to you]. Whether that’s studying, or spending quality time with your family, or taking a vacation when you feel you’re about to burn out. Figure out what your Type A activities are and don’t let one be more than the other. Structure your life.

DI: School…

SJ: School isn’t for everybody. But hardship in life is for everybody. If you’ve been fed with a golden spoon your whole life you haven’t learned shit and you’re probably not going to make it on your own. Doing the hard work is a good thing.

And you have to have faith in the process. I remember sitting in algebra class wondering when am I going to need this? I don’t do hard math at TribalScale, but it had a purpose. It taught me the mechanics of figuring out what the variables are in decisions I’m making and cutting to a conclusion. So the correlation to your real life doesn’t have to be direct for it to be useful.

DI: The word “failure” has been used a lot lately in the conversation about startups. What is it, exactly?

SJ: You’ve got to go above and beyond the expectations you set for yourself, and anything short of that’s a failure. And that’s ok. Because you’ll fail 15 times, and then you’ll learn how to be more than perfect the next time.

DI: As a co-op student, how do you win respect after messing up?

SJ: Come to me and say “I fucked up, here’s why I fucked up, and here’s what I’m going to do to fix it.” Or, “here’s what I learned so it doesn’t happen again.” Once you get called on your bullshit, it’s game over—that’s when you lose the respect.

DI: What is success to you?

SJ: It means happiness, and having a sense of self-worth. Feeling like I’m actually making an impact. And that’s a big thing to be able to say. My goal with TribalScale was to band together and have this culture of people who want to be the best at everything they do. Were we successful at that? Yeah. Is our job done? No because now the goal is even bigger.


How to get hired at tribalscale:

Listen to the podcast at 30:45 to hear Sheetal’s exact advice.

Another coffee down, I hope you guys learned something. Big thank you to Sheetal for opening up and sharing his wisdom.

P.S. Have you read the previous 100 Cups of Coffee interview?

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