Sheetal Jaitly

Sheetal Jaitly is the Founder and CEO at TribalScale, a software design and development company in Toronto. Sheetal is a 13 year veteran of the tech industry. In the late ’90s Sheetal worked in mobile right out of high school where he was part of the Palm Pilot launch with USRobotics in Canada.

When Sheetal joined Xtreme Labs as the Director of Business Development for Media, he quickly expanded the Media vertical for the organization. As Xtreme was acquired by Pivotal Software, he expanded his reach as he took Telecommunications and IoT under his belt. In his current role as CEO of TribalScale, Sheetal is applying his business development skills to quickly scale the young IoT and mobile development company. Outside of his day-to-day role, Sheetal is an avid investor in the technology space as well as a volunteer and member on the BoD for the Ontario Association of Food Banks.

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Sheetal Jaitly talks about his unconventional journey as a founder, along with his personal experiences around depression and grief. He shares why we need to be honest with each other and what founders can truly do support their employees.


Yeah. Thanks again for being willing to do this. When I was first thinking about who I wanted to feature in the platform, you were one of the first names that came to mind. You and TribalScale just welcomed me as family, so I just wanted to convey that.

For sure. I'm happy to do it. Any way I can help. I love the initiative you're doing. I think it's completely underserved with the magnitude of the issue. If I can be that one little piece that helps, I'm happy to be that person.


You're so active in Toronto, so a lot of people know about your work. I'm still curious about who you are as a person. What's your story?

My story is I'm a grinder. I'm not the most polished CEO. I think that's the first fault that I may have. I've been a business development guy almost my entire career, but I was exposed to tech at an early age.

My story starts right out of high school. I started working for a company that represented micro-computer companies here in Canada. One of the companies they represented was US Robotics. I remember playing with a Palm Pilot 1000 when I was 17 years old. I worked on the logistics department of the company. I was the guy responsible for packaging warrantied units. I was this amazing device, but my curiosity led more, “How does this device work? What could it do for you?” My natural curiosity started taking over.

To fast forward, there was a point in 2002, 2003, where the tech bubble burst. I got laid off because the tech dollars were drying up really fast. The sense of business and the business ride really hit me.

At the same time, I ended up losing a really close family member. Very similar to your situation; you've been there. It's really hard to take in. That started affecting my school. I just wasn't passionate about school anymore. I ended up dropping out of school. I felt I was a lost soul. I didn't know where to go next. I couldn't even see where my next foot should go.

That comes with a lot of things. You don't have a sense of purpose anymore. You're not in school. You don't have a job anymore so you try to figure out what you should do with your life. You've got family that's really close and cares for you, but you're so fixated on the major loss you had.

When I say I'm a grinder, it's because I think back to the way I felt that day. I feel like I've grinded inch by inch, by my nails, and just crawled my way at a very slow pace to get away from that spot.

It's not that those feelings don't come back. It was my father that actually came to me and was like, "Hey man, you're not yourself. You're not leaving the house. You're just laying here all day. This is not you. You're a social guy. Just go get any job. Go do anything. You'll figure it out.” So I went and said, “Okay, I got to make a change."



I started talking with a bunch of other mentors and people around me. In a year where I lost multiple family members, one super close to me like a brother, then losing grandparents that lived with me.

That year, I felt like the whole world… I could only just see black. I couldn’t see clearly.

Some really close people came to me and said, "Hey, Sheetal, you've always had a knack for sales. If you want to get your MBA in sales, go in the photocopy business." I started selling photocopiers door-to-door for very little money.

Everything was upside in commission. I went through this formal sales training which legitimized a lot of the things I did, taught me a lot of the stuff I do wrong. I started my business development career from that point. I started working with an amazing group of people. It was very male-dominated. Think about alpha males. There was a whole bunch of chart paper all over the wall. It'd be for the month and every time you close a deal, you'd put your deal up on the wall.


It's all public?

All over the office.


Very competitive.

It's competitive, you're competing against yourself. We would cheer up the guys or the girls who would have nothing on the wall. Then the cool thing that started happening was when you were struggling with a deal, everyone would come and help you. They’d be like, "What can we do to help you get a deal? Why are you in the slump? Here's some things you can change. Let me go on call with you. Let me try to help you close a deal."

To come out of the depressive state I was in and to go into that was very difficult. You get told to F off and get the heck out of my office. Cold calling is not picking up the phone and calling. It's going door-to-door in businesses and smooth talking reception into letting me speak to a decision maker who could actually buy from you.

The rejection part wasn't what was scaring me. What would scare me to go back into depression was the risk of failure. The society that we live in, especially with the dates I'm talking about back then, it's like failure was not embraced. Failure was, “You suck.” That company was a great experience.

Then there was a point when I said, "Hey, is it time for a career change?" I ended making a career change and I went into software services. A lot of cool things happened at that place. The place I was working taught me was okay to fail fast, to mess up, to take chances, and that it's okay. You still have a job at the end of the day if you go do that.

I started growing so much more as a person. That was really something that helped catapult me.

As you know, I have a couple friends that started Extreme Labs and my curiosity again for tech led me to them. I started working with them and heading up the Media division, which was the largest share of the revenue we made. We got acquired and then I went on to Pivotal. I saw where the company needed to go to IPO and it was really hard for me to find my footing there. I saw a huge need in the market that allowed me to start TribalScale.

Here we are, and now this journey has been. What a roller coaster. The ups and downs are crazy. Everybody who thinks growth happens in a linear way, where it just goes from bottom left to top right is out of their mind. That is not how growth happens and that's not how anybody gets to where they are.

You have your ups and you have really a lot of downs.

As entrepreneurs, when we share stories, we share only the up moments. Not enough people talk about the down moments. The down moments are the ones we learn from. We started this organization. We knew we had product-market fit, which was a lot more than a lot of startups have. Then you start going on the rollercoaster of how you're going to make this thing grow.

Every day there's an up and down battle that happens. There's challenges that you never thought you'd have to face as an entrepreneur that you have to face. There's things that become personal and people say something about you or write a bad review about you or whatever it may be. It's tough not to take that stuff personally, but at the end of the day, you gotta look and say, "What can I do to make myself better? Who can I confide in to take some my mental stress off me?"

Which is why it's so important to talk about your down moments. How could you create an organization that's going to be better for everyone? Our mission statement is, "Write the future." We see the future going wrong in so many ways and we want to be the ones who actually write it the right way.

I got to say though, Cherry Rose, there's mornings where you don't sometimes want to get out of bed. I think once you face that depressive mindset, it never really goes away. I call it my ball and chain. It's that weight that always pulls me back sometimes. I sit on a CEO forum group and have open, very candid conversations with them. We actually have one today.


Thank you for being real with me, by the way. I felt so much of your tenacity, despite the hardships you have experienced. Especially when you mentioning being the grinder.

Well, I am the grinder. I grinded all the way here, I dropped out of York University. I flew back all the way from Dubai for less than 24 hours just so I could. I had a talk on my calendar to go speak to the students and entrepreneurs at York. What an amazing thing to have happen.

Here's a dropout who grinded his way and learned a lot of lessons the hard way. Like I said, pay it forward. Put all that knowledge back.

What I will say though, I think everybody should be an entrepreneur. In my mind, every time I work for a company, I was an entrepreneur. I got a desk, I got a phone, I got a computer, and I'm tasked with a running goal. You got to think outside of the box.

I tell all the young people that we work with here, "If you don't see opportunity for yourself to grow, it's not the right place for you. You should throw away the titles, throw away the money, throw away everything else. Focus on what's going to be the opportunity for you as an individual to actually grow, so that you can be where you want to be in five years." Naturally, if you start doing those kinds of things, I think it starts making you happier.


Right. I feel a lot of gratitude even just the last 14 years, my brother and I started off in entrepreneurship pretty early. We came from generations of entrepreneurs.

Which is a great example [Sheetal and my brother used to work at Xtreme together]. He was always an entrepreneur. When he worked beside me, he didn't look at the business like, “I'm working for someone.” He looked at everything we're doing in business at Xtreme as, "This is what we gotta do because it makes sense."

He was like a sense of ownership he took with the role that he had. Right?


Yeah. I love that perspective that you took because from the ups and downs, we get to find our truths. We get to know who we really are and take ownership of our lives.

There's times I lie in my bed and I'm like, “I've got to get up because I've got these ten things to do.” Sometimes you just don't want to. I'm being self-destructive. You know you are, but you still don't want to do it.

Those are the moments you really got to reflect and go, "Stop. What are you doing? What's going to make you happy? Get up. What is the root cause of you not wanting to go do this right now? What's your vision of what's going to make you happy?" Follow that.

That's one little thing that works for me. When you're in that moment, wait a second. Get up and go face this meeting and do whatever you gotta do, but look to your vision to where you want to be. It won't be overnight. There's no overnight success. I've been grinding my ass off. I've been working more than part-time so more than three days a week since I was 13 years old.

Nothing happens overnight. But if you stick to that vision and walk towards that light at the end of the tunnel, you'll naturally be happy and get there.

I don't have the secret recipe. If you've talked to someone who does, I'd love to listen to that. Every day is a struggle.


What's really humbled me about mental health is that it doesn’t discriminate. Even people at the highest experience it, like when I was an educator teaching the richest families in the country.

I think it gets worse. My parents were not super successful. They worked their ass off, they still work their ass off. I contributed to paying bills at home. We lived a good life. We lived a good life and they did what they did.

I can only imagine if you have parents that are super successful, everything you do you think has to be at the bar at where they are. That's impossible to do as a young person. I can imagine the stress that goes for someone who's trying to live up to those big shoes.


That is a real problem for people at the top of the mountain.

Loneliness for a founder is, there's a saying. It's funny. I was talking to another founder who also worked at Xtreme. I gotta love what that place did; he knows me very well. He was like, "You're just not the same. What's going on?"

I was like, "I just feel lonely. I don't know what it is." He's like, "You know it's not a cliché term saying it's lonely at the top. I get it."

I started looking at it. If you look at a founder, you're not with your family, you're never with your family. You're always working. Your job almost ends up defining you. Every time you talk to someone, it’s always goes to business first.

All the sudden, you start losing your self-identity. Is my job at TribalScale define me? Is that all I am now? That's a struggle. I can only imagine if it got ripped away from you if I didn't have it. Let's say I didn't have it. Who am I now?

You see founders trying to find the self-awareness after they've been acquired or whatever it is. It does get very, very lonely. You're always traveling. I'm pretty lonely right now and you just want that real meaningful connection with someone. You can't even do that because those things take time and you just haven't put the time or effort into that.


Yeah. Thanks for sharing that. It is so important that people to share their experiences, so that we can learn from them.

Sometimes, I think one of the solutions is doing what we're doing now. Letting people know that it's okay that this happens too. Having a safe space to just get it out sometimes takes a lot of the burden off your shoulders.

The more and more people talk about it being okay, I think we'll drive a lot of happiness to founders and A, make their day to day lives better, and B, reduce the risk of suicide amongst founders. That's huge. Even if we save one or two lives, that's massive.

At least we're talking about it. Hopefully the more conversations we have, we'll start coming up with more solutions.


Yeah. This is the optimist in me. I want to see founders really feel like they're seen and heard. Not just you as CEO, but you as a human being.

Yeah. I was with Janet [who we shared a mental health panel with at CIX] and we were judging this women founders’ competition. They went through a whole program at DMZ and Janet said, "How are things going? I see and hear about you guys all the time."

I told her, "Actually Janet, really shit. Personally, Janet, really shit. I felt like I needed to get away, so I got away for a little bit with a good friend. Wanted to talk things out and clear my head." And she said, "I'm so proud of you for saying that."

Most people would be terrified to say that out loud. You've got to show your vulnerability more and more. If you think it's going to be used against you for ill will or anything like that, I'll tell you from my own experience, it doesn't happen as much.

Be vulnerable, just be you. Hopefully they get to see through you and actually get to see the real you. Then you're not the founder, you're not the CEO of some company. Then they actually get to know who you are, once you take that first step in vulnerability. From there, you can actually start building a real personal connection with people.

If you look even in the Valley, if you look at a bunch of the CEOs that are up there, could you really tell and know who Jeff Bezos is? Probably not. Do you know who Steve Jobs really was? Probably not.


I feel like the pretending is quite exhausting too. At CIX, I saw a keynote where someone was talking about chronically stressed employees. For those people, they spend 25% of their total brain power, the total cognitive load is on pretending. That's crazy.

Crazy. It's crazy.

At the founder level, I'm telling you, you gotta walk around all the time with a big smile on my face like everything's okay. It's not though. If everything's not okay, it's okay to walk around and be like it’s not okay. You just gotta do it in a way that doesn't harm others.


I wonder about it a lot. There's a book I've been reading. It's called Dare to Lead by Brené Brown. Someone had referred it to me. There was this really interesting model she had about leadership. How vulnerability breeds courage, while armour breeds avoidance.

Even being a founder, there's a couple of things. You care about executing on your vision and the second biggest thing is you care about your people. You want to do both. You're not going to execute your vision without your people and vice versa.

Those are the two things. If you don't create the safe space for everybody else to be like, “Okay, he can be vulnerable, then it's okay for me too.” It's tough.

That's something that as a society, as whole, until you start going initiatives like this, it doesn't get said. Which is why you're getting people who are coming up to you because I didn't even realize it was a safe place to go to talk about this.

Again, I said this on the panel, it's the level of stress you may be going through. The topic or the issue doesn't matter. It's what you're actually going through in the minute.


The actual feeling.

The actual feeling. Anything we can do to help each other when we're feeling those feelings that we don't want to have. We should be very sensitive and listen, rather than trying to fix. It's actually sitting to you, listening to you, understanding where you're coming from.


I love that. When I was teaching Special Education, my kids often dealt with things like depression, anxiety, and self-harm. You don't judge what they say; you help them see the good in themselves. I would ask questions like, "Tell me what you’re feeling. I know you feel low right now, but you think something about yourself that's really special? Can you think about something about yourself that inspires you everyday?"

We all go through it. 100% of people on this planet go through it. There are varying degrees to how people handle it. The top anxiety that the happiest person experiences, it's still the same feeling that I feel when I have top anxiety. When we both hit that moment, it's the same.


I’m humbled because I hope more founders will come together in support of mental health.

Yeah. At TribalScale, I encourage founders to talk about mental health, so we have a bunch of initiatives on mental health. We have Inkblot here, which goes above and beyond to going online and speaking to someone in a confidential way. We have employee assistance programs (EAPs) that allow you to go seek professional help. Last but not least, we wanted to make it a safe place where you can go to HR, especially if you're actually suffering. There's been cases where that happens.

Sometimes, someone needs additional help that goes above and beyond. We get to be the ones to say, "Hey, we'll take care of our people. We'll front the bill for them and put them down the right path." We'll do that. Or someone may need time off that they don't even have and we'll just go make the time for them.

That's the right thing a founder should do for their people.


Thank you for just leading by example. To have someone who is leading such a fast-paced company, someone who's been such a pillar in the tech community, I think is commendable.

Yeah. Nobody has to go work 80 hours a day, but I think if you believe in the vision and it becomes your passion, then you're naturally going to go work hard at it anyway.

We all have our ups and downs and it's okay to be vulnerable. Why don't we solve the problem together is my approach.


Love it.

Awesome. I'm happy to do this. That was great.

Cherry Rose Tanwave1