Sheetal Jaitly gives his employees stickers that say “Fail Fast”.

And he’s completely serious about it, though he doesn’t take failure lightly.
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Fail Fast &
Fight Hard:
Sheetal Jaitly’s
Self-Made Story

Scaling A Tribe

“I had the money to make the home with a white picket fence dream a reality. But I wasn’t happy. I was just one person at a desk in this big machine where I didn’t feel like I made an impact.”

Jaitly started TribalScale in November of 2015, walking away from a solid career that he knew could provide the financial security he fought for so desperately since watching his parents’ financial foundation crumble. Instead, he saw a gap in the market and was excited about the potential to produce five-star digital products and transform enterprises in Agile ways.

He didn’t need to wait long for TribalScale to land its first big client. Jaitly was half-way through his pitch for one of the world’s largest media companies when the decision-maker – a former client of his from Pivotal – told him to stop the presentation.

They told him bluntly: “We’ve been working together for five years. You once could have sold me a big product that I would have bought with no hesitation, but you didn’t. You said I wasn’t ready for it and coached me on why it wasn’t right for my business. I realized that you rejected the opportunity for a huge commission just to do what was right by me.”

The client handed Jaitly a $1.2m contract and TribalScale was suddenly in big business.

“A lot of people in business – and in life in general – look to take, take, take as opposed to looking at life through an empathetic lens and doing what’s right for nothing in return. What they don’t realize is that doing what’s right comes back to you exponentially when you develop the right bonds.”

In three years, TribalScale earned just over $50m in revenue, grew the staff to 250+, and had seven offices around the world. Then, they imploded.

“Boy doesn’t life hit you in the face when you think you’re doing everything right.”

Jaitly said that TribalScale grew too big, too fast. Their culture was ruined. Their fundamental practices weren’t followed. They were doing business in areas where they had no business being in.

“It’s easier to walk away and start over, but I looked at this mountain of a task in front of me and decided to start moving it rock by rock.”

Restructuring a business is never easy, especially when there’s a pandemic on the horizon. The first months of 2020 saw TribalScale lose 80 percent of their customers. Instead of severing ties, Jaitly did the unthinkable: he reinvested in his clients at no charge.

“Shit hit the fan for the whole world but we stood by and did what was right for our clients.”

We all know the end of this story: budgets came back quickly as digital products and services became more important than ever. TribalScale met these challenges with a Tribal mentality: taking care of the weak in your group brings strength to everyone.

Removing Rotten Strawberries & Transparency From TribalScale

Sheetal Jaitly has removed ‘transparency’ as one of the three core values that act as TribalScale’s north star.

“We’re still transparent – we can’t solve problems or do our jobs without transparency – but we made the choice to remove it from our core values. The term was used to attack people.”

He used an example that anytime someone would start a sentence with “In the interest of transparency…”, it would almost always be followed by a negative remark that was more politically motivated than professional.

“Taking out transparency as an official core value took away a free pass to be a prick.”

Transparency was replaced with resiliency, a term which complements the other values (empowerment, and challenge and collaborate) quite well. Jaitly believes that his team should feel empowered to create the company that they desire, even if that means creating a safe space where healthy friction through debate can pave the way for new perspectives to thrive.

“A company should be a platform for people to succeed in their careers and in their personal lives,” he said.

“People aren’t clocking into TribalScale just for a paycheck; they want to use their minds in a way that benefits them and the big picture. We look at our staff through a humanitarian lens and wonder how we can help each other excel.”

That being said, Jaitly is quick to point out just how important it is to remove the bad apples – or, in his case, strawberries.

“One of my peers told me about the rotten strawberry theory: if you don’t remove the rotten strawberry from the pack then it spoils the others. I never got rid of employees, especially those who were great performers with bad attitudes. I wanted to work through it, but now I see that to be mission-oriented for the company’s sake, I have to be friendly – not friends – with my employees.”

Jaitly understands that the high-pressure start-up environment isn’t right for everyone, and that’s more than acceptable. He’d rather help them get a job that they’ll love elsewhere.

“You’re not a bad person if you don’t agree with our vision or want a steady nine-to-five job. Let me coach you to get a job you’ll be excited about. Let me hook you up with a different job so then we all win, are successful, and are happy.”

Today, TribalScale is building five-star digital products, transforming organizations with their TribalDNA, and running a start-up studio to create solutions to tomorrow’s problems. Jaitly is currently enrolled in the OPM Program at Harvard Business School where he’s learning how to be a better CEO.

“I don’t want to let down the people that are with me,” he said. “I want to make sure their families and careers are on the right track and challenge them to do better for themselves.”

When looking at a future that may include other forms of failure, Jaitly admits that his failures at TribalScale have encouraged him to diversify his risks and constantly look for leaks in the boat. More importantly, he acknowledges that success and survival depend on one important factor that’s not born of the business.

“You don’t get anywhere without having people in your personal life be your rocks. We too often talk about individuals in the organization and the impacts they make, but I’m also cognizant that I have a supportive family that challenges me. Those who work with me also have personal units that are supporting them. There is no ‘me’ without most people in your life. We are successful because of the ones making sacrifices to support us at home.”

Advice From The Tribe

You invest in employees who want to quit; you’ve invested in clients who don't have the budget to spend. Why take on these unnecessary risks?

I don’t need a payoff for my actions. We’re in the people business; we all have different motivations. If you’re working with me and it’s not the right place, I’ll still do what’s right by you. I’m not looking for a transactional relationship; I’m looking to do what’s right for all of us. When employees self-select out, I get to help them flourish elsewhere instead of outright letting them go. If you can’t have transparent conversations with your employees or clients then your company won’t get the ancillary benefits that create a healthy company culture.

What’s the worst piece of advice you’ve ever given?

It’s not advice, but I blame myself for my past temperament and not being patient enough. It’s been a long process over these last five years, spending time trying to not overreact to situations. I grew up a fighter so my first instinct was to react. Now, I try to approach a problem or conflict with a clear mind, determine how to get to the root of the problem, and figure out a solution. In business, we’re taught to act rigid and formal as leaders but it’s more beneficial to interact with employees on a human level.

How can an entrepreneur stay focused on their risk areas while swept up in success?

Having someone you trust — someone who you can go to openly with humility – is key. You need someone to talk to about your weaknesses; preferably someone outside of your business who really understands your business. You need to have confidential conversations with those who will tell you when your shit may stink.

I may know where some of my failure points are but I love it when the people I trust point out my blindspots.

What are you too “old” in your entrepreneurial journey to do right now?

I started this company in my 30s and would always put big goals on the board. When naysayers didn’t think it could happen or when I saw someone not making it happen, I’d do it myself just to prove that I could get it done. In my 40s, I won’t do that. It’s rewarding bad behavior. In my role, I should be the one to jump into the task with an employee who’s struggling, but they’re going to do the work. My ego once drove me to do all of the work myself just to say ‘I told you so’. Now, I want to be a better coach and delegator.


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