Nobody warns you about the middle of the night: Vivek's story

This week, I'm back with a guest, who I spent time with in Atlanta last week.

Vivek Venkitaraman is CEO of Undocked, a consulting firm headquartered in Atlanta, Georgia, with offices in India. They help retailers and distributors modernise their supply chains, and they're about 175 people.

We've just spent three days together, working through how to align digital product, marketing and sales behind where he's taking the company and what matters to their customers. I've been amazed how motivated and committed his team are. Everyone turns up, they want to get involved, they want to help.

This written version is a summary of our recording, and our time together over the three days.

You can watch the full video on YouTube, Spotify, or see the embedded video at the end of this post.

"It's a blur now, it was a blur then"

Vivek was 18, had just started college in Bangalore, and was doing a lot of partying. His dad, an "eccentric genius", didn't like where he was heading.

Going to the US for an undergraduate degree was unheard of back then. But his dad decided it would be better character building for Vivek to work his way through college.

Dowling College came to Bangalore to give a presentation. His dad went along, asked at the end what they needed, and had all the paperwork done that same day. They carried his application back to the States with them.

Literally overnight.

"It's a blur now, it was a blur then. But it happened so fast and I was here before I knew it."

He arrived in 1996, studied computer science, interned at Manhattan Associates in Atlanta and joined them full time. He's been in retail and supply chain ever since.

He was on the founding team of Keystone Logic, which was acquired in 2019. He founded Undocked in January 2020.

By March, COVID had hit.

"We were all sitting in our collective basements, wondering what's next."

The first 18 months were slow going. But he put together a team of people he'd worked with before, and that core team is still with him today.

With me, not for me

When I asked what it takes to grow a business that far, his answer was about people.

"I wanted a group of people to come work with me, not necessarily for me."

That means skin in the game. The core team have ownership, equity and the freedom to make decisions themselves.

"My job is super easy because I never have to go and sell."

A lot of the textbooks say a successful company is cutthroat and driven by the numbers, where only the people at the top win. What Vivek's built is a good company looking after its people, and the success comes off the back of that.

He also has a propensity to say yes to everything. Not all the yeses have worked out, but "that for me is akin to making one's own luck."

Nearly every founder I've met who's built something has that same propensity to say yes. And of course, it's also a nightmare at times!

The weight of responsibility

When you hit a certain size and scale, the weight of that responsibility creeps up on you.

"It kinda sucker punches you in the middle of the night sometimes. And nobody warns you about that."

He never calls it a burden. It comes with growth, so it's a good thing, and he reacts to it with gratitude.

"It is lonely at the top, but at the same time there's good people supporting you."

Some time back for ourselves

Vivek does CrossFit. "You go into a pain cave and just stay there for sixty minutes."

Running has the same impact for me. He also talked about the fact adults stop sprinting after a certain age, so he still does sprints to not find himself in that situation.

"I'll be fifty next year. I want to keep doing stuff just to prove to myself that I can."

We went for a run together, and despite the last part being uphill, we sprinted at the end. He beat me. His response: "You didn't forget and you didn't fall on your face."

For me this sums up Vivek's approach to life and work. Lean in, say yes, keep pushing forward, but balance it with kindness and humility along the way. And it seems to have been hugely successful for him.

Our conversation moved onto AI, and the fact that since the industrial revolution, every step was meant to make our lives easier, but somehow we got busier. We built cars to get from A to B faster, and we're still stuck in traffic for hours.

"I'm hoping that AI would be that revolution that would give us some time back for ourselves."

Time with our families, and to be more present. For Vivek, that's the biggest win. Everything else is secondary.

I said right now it feels like it's consuming more of our headspace and time. His view is that nobody has figured out what we want from it yet. "It's gonna get harder before it gets easier."

Perhaps a good reminder for how we should set our expectations.

During my trip, we spent a lot of time together, on early morning drives, over lunches and on our run, talking about family and community. Both near and far.

What's struck me on the whole was how similar our cultures are.

Diwali is coming up, the biggest festival of the year for Vivek, and he shares it with his American and Indian friends. And he can't say enough about southern hospitality.

"This is home to them [his kids] for sure. It's home to me too."

The Friday Takeaway: leave your work behind

Vivek's takeaway is to leave your work behind, get outside, as often as you can, and now is the perfect time of year.

"It's a learning that I have to invest some time and effort in, to be able to just let things go, and take that time off and be completely disconnected from work. Because work's always there and it's a big part of who I am, especially because I'm a business owner."

He admits he doesn't practise it yet all the time.

"I have to train myself to do it. I don't do a good job, but for anybody listening, I think that's great advice."

It's often the thing we least want to do, that we most need to do. I can certainly relate to all of this. And it's a great takeaway for me to reflect on over the weekend!

And I do think it can help with those midnight wake-ups that I experience too!

One question for you. When did you last sprint?

Until next week... here's the full video.

And please do drop me a response to my question above, or simply like / follow if any of this is interesting.