Thank you!

At 11:58pm on October 13, 2015, Flipkart’s product and engineering teams were assembled in a series of war rooms. It was the eve of ‘The Big Billion Days,’ the Indian e-commerce giant’s annual blockbuster event. Mobile phones were about to go on sale, and the stakes were incredibly high — the team knew that this event that could bring in many months worth of revenue in a span of five days.

At the stroke of midnight, however, the site promptly crashed. With traffic dropping precipitously, each second that ticked by meant thousands of dollars lost. As stress skyrocketed and panic set in, Punit Soni was in the proverbial hot seat. As Flipkart’s Chief Product Officer, the team was looking to him and his engineering counterpart, Peeyush Ranjan, for their marching orders.

“It was the clearest illustration of the paradox of scale. You have hundreds of people at your disposal to attack the problem. But where are you going to point them? What should they actually go do?” Soni says. “My immediate instinct was to tell the senior leadership to back off so the engineering team could put their heads down and work — we’d follow their lead.”

Seven minutes later, the culprit was identified— a DDoS hack from abroad that directed a giant traffic surge to overload the servers and disrupt the big day. How would Flipkart respond?

Soni was no stranger to making the tough calls at large companies. Before joining Flipkart, he came up through Google’s school of product management, eventually leading the mobile apps group before moving on to serve as the VP of Software Product Management at Motorola. But at midnight in Flipkart’s Bengaluru office, he realized that leading on a massive scale sometimes requires starting small.

"What we decided to do was actually pretty crazy," Soni says. "We shut down all traffic coming into Flipkart from outside of India. We would, of course, lose some revenue, but it was worth it to cordon off the country where the majority of purchases would be coming from,” he says. “It was an insane, weighty decision to make in the moment, but I’m glad we pulled the trigger, because if we went down and ran it by the senior executives first, we would have debated it for an hour."

In a sense, this bold gamble might have foreshadowed the role that Soni would take on next: startup founder. After leaving the behemoth that is Flipkart (which has since been acquired by Walmart), Soni struck out on his own to co-found and lead Suki, a healthcare startup that offers an AI-powered, voice-enabled digital assistant for doctors.

In this exclusive interview, Soni reflects on the lessons he learned as he transitioned from the scale of helming product at large companies to the rollercoaster ride of founding a startup. He shares his observations on the differences between the two experiences, noting what surprised him, what he felt unprepared for, and what aspiring entrepreneurs should consider as they look to make a similar leap from big to small.

THE STRENGTHS — AND CHALLENGES — OF PROBLEM-SOLVING AT SCALE

Before Soni left the world of large, established empires to build his own startup, he had a front-row seat to the advantages of working at a massive organizations. While leading software product at Motorola, for example, Soni was awed by his team’s ability to leave a vast and immediate impact.

“We decided to push OS software and core feature updates in real-time, instead of doing a big splash with new devices every two years,” he says. “So when we flipped the switch, it directly affected millions of people with our phones. They woke up to a new feature, on the most intimate device they used. It's an example of what scale and speed can do when you put them together, and that's an exciting aspect of working in bigger enterprises.”

Large companies are elephants — they move slow, but they can clear the jungle. A minor tweak here and there, and suddenly you’ve made a fundamental difference in people's lives.

Of course, sheer scale brings on frustrations as well. “The biggest issue in large companies is the random politics that is created out of ego, insecurity and miscommunication. The challenge for leaders is figuring out how to tackle it,” Soni says.

As with most organizational problems, he found the solution came down to communication. “Whether you're in a big company or a small startup, a leader's first job is to create a communication map. Without that, the business can’t run — culture goes to dogs and bad decisions get made,” he says.

Embracing the role of communications cartographer, Soni spent his first few weeks in new roles at Motorola and Flipkart interviewing everyone from the ground floor up to the executive suites to gather insight on what was working and what wasn’t. “Like most companies, there were too many meetings. Decisions were being made in 50 different meetings in rooms across the organization. To solve for that, we created a four-hour, weekly product decision session, where anyone in the company could sign up for a slot to get a decision made. If someone showed up with data, context and a few slides, my promise to them was that we wouldn’t leave the room until they had a decision,” he says.

Even with new initiatives and mandates, roles at large companies can seem limiting compared to the many hats a startup founder wears. To assess whether discontent is within the normal range or whether it’s time to move on, Soni recommends a key ratio.

HOW TO TAKE THE STARTUP PLUNGE: TIMING, PREPARATION AND PUTTING IN THE WORK

By the spring of 2016, Soni felt the siren call of entrepreneurship was too loud to ignore.

“I reached a point where I felt that in my next role, I wanted to solve a problem that had a clear and direct value to society. And I also wanted to flex muscles that haven't been used in a long time. Putting those two factors together, it sounded like doing a startup would be a good idea,” says Soni. “At that point in your career, you can keep being the VP of something or take a C-Suite role at another large company. So I felt that if I was going to leave to take a big risk, then the right way to do it was to take on something really ambitious. For me, spectacular failure and spectacular success are both better than mediocre middle of the road outcomes.”

Here’s Soni’s advice on what aspiring startup founders should consider before diving into the waters of company building:

Time it right and prepare your pack.

Aspiring entrepreneurs often dwell on the question of timing — there’s a delicate balancing act between soaking up experience at other companies and striking while the iron is hot enough for a venture of your own.

For people early in their careers, Soni's advice is simple. "If you're a 22-year-old who just got out of school and really has nothing to lose, go knock yourself out," he says. "Because as soon as you get further into your career, even just two or three years in, the stakes just feel higher mentally.” But for those who are already midway through the flight plan of a successful career, as Soni was, the prospect of transitioning from big to small can feel much more daunting. "To be completely honest, for me to do a startup at this point in my career, in terms of opportunity costs, is potentially several millions of dollars," he says.

To put himself on the path to entrepreneurship, Soni started planning. “I promised that I was going to work towards giving myself the permission to do a company, so I started methodically running through what I needed to make that happen,” Soni says. “I knew I needed to build a good network so that when I actually left, I’d have strong connections with investors, as well as relationships with other entrepreneurs and engineers who would mentor me, help me and also join me. Spending time laying down all of that track can of course be a multi-year effort, and that’s okay. Continue to chip away at it, even if your startup idea isn’t whole yet.”

In Soni’s eyes, this dogged practicality is a counterweight to the somewhat fanciful notion required to start a company in the first place.

“Doing a startup isn’t a sound financial decision. Logically, the odds are so stacked against you that it doesn't make any sense. Jumping into life as a founder is a romantic decision. It's the kind of move you make when you want some adventure,” he says. “But that doesn’t mean you have to leap off a cliff. Starting a company is like climbing a steep mountain — you need to take the time to prepare your pack. Fix your finances first. Make sure that you can survive a couple of years without any income coming in. Build those connections. Vet your idea. Prepare your loved ones for the rollercoaster that’s about to come.”

The best advice I can give you is to start a company from a position of strength. The time you invest in preparation now will boost your startup's sustainability, not to mention your own well-being, further down the line.

Put in the work to find the idea.

Would-be founders looking to shore up that position of strength can tinker away and spin their wheels endlessly while searching for the perfect idea to go after.

“There’s this false narrative that founders are just walking on the street, and they have this light bulb moment of ‘This is it.’ In reality, you have to put a lot of intellectual vigor into figuring out exactly what you want to do. You need to carve out time specifically for that task by reading up, doing diligence, exploring different spaces,” says Soni.

While budding entrepreneurs might feel tempted to look up to the dropout-to-billionaire stories of Bill Gates and Mark Zuckerberg, Soni is here with a warning. "Those are exceptions. Don't confuse the exception for the rule. We know that in life, along with genius and smarts, you need dollops of luck. If you actually want to do a startup, it's better not to bank on luck. Prepare and plan thoughtfully,” he says.

More broadly, Soni recommends keeping your mindset in check. “Remember that doing a startup is a privilege. You want that privilege? Work to put it together. It’s just like getting into a top school or amazing company. If you want the chance to start your own company, work for it — don’t wait to get inspired.”

Worry about go-to-market, not product.

When an idea is finally in sight, it may be tempting to jump feet first into product building. According to Soni, founders need to resist the impulse to obsess over product to the exclusion of everything else at the very beginning. “It’s tempting to slip into a ‘build it and they will come’ mentality, especially if you’re convinced of your own product prowess. Now I’m a product manager through and through, but I’ll be the first to tell you that product usually isn’t the issue,” he says.

Instead, tackle go-to-market, working through who’s going to buy, why and what they would pay. “Product is more binary in that, either the tech will allow you to do it or it’s not possible. Making sure that you can build a sustainable business model around that product is a far tougher task,” Soni says. “Figure all of that out before you start a company, not as you go along. Once you check that box, then you can become a product-focused company.”

Startups die at the mercy of go-to-market, not at the hands of product.

Serve the user, not yourself.

Soni eventually landed on the idea of starting a healthcare company, but he didn’t have much direction beyond that. “I had zero experience in healthcare, so I spent six months just shadowing doctors and embedding myself in large health systems to learn what kind of issues they were facing,” he says. “Nothing replaces in-person observation as a tool for figuring out both go-to-market and product.”

At one point, he thought he might have stumbled onto a winning idea. “It was essentially what Slack did for healthcare. There’s so much communication in a hospital, it seemed like there was a desperate need for it. And I knew I could build a great consumer product,” Soni says.

Over lunch in the break room with a group of nurses, he pitched his big idea. "They looked at me and said, 'Punit, I use a fax machine, pagers, Microsoft Outlook, electronic medical records, and paper documents on top of that. I will not use another communication protocol. In fact, if I see anybody else using it, I’ll actively try to stop them,” Soni says.

The criticism stung, but the nurses' brutal honesty was eye-opening. “It was an idea that I was personally very excited about. But it's an example of how you need to understand what the user is going through when you’re coming up with these Silicon Valley ideas to solve their problems,” says Soni.

When founders find themselves wedded to an idea, they run the risk of refusing accept any information that seems to contradict or diminish it. “You have to spend the time asking a lot of questions and truly listening, but also translating,” Soni says. “Most users don't necessarily know what they want, but they do know what's hurting them. It's your job as an entrepreneur to convert what's hurting them into a product.

If you’re open to having your ideas challenged, you'll have a far greater chance of creating the product that your users actually want — not the one you think they want.

Visualize writing your own check.

As a final box to check before preparing for launch, Soni recommends taking a step back to truly evaluate the idea — and your commitment.

“Take your net worth, whatever it is. Then picture yourself writing a check for a chunk of it. If a smart founder pitches you this very same idea, would you give her that check? If you can see yourself investing, then you should go do that company,” Soni says. “The day I felt I would take a million dollars of my own personal money, dump it into my startup and think it was a good investment is when I decided to accept venture funding.”

Punit Soni, co-founder and CEO of Suki

POST-STARTUP PLUNGE: LEADERSHIP OBSERVATIONS FROM THE OTHER SIDE

With idea in hand, funding secured and startup in motion, Soni next had to turn to the nuts and bolts of life as a founder: hiring, team building and leading. Suki has raised $20 million in funding, grown to a team of nearly 40 people and notched a few notable successes along the way — but that doesn’t mean Soni felt he had a handle on everything.

As he transitioned to his new role as co-founder and CEO of an early-stage startup, Soni quickly realized that his understanding of his a role as a leader had to adapt. “I definitely felt unprepared in many ways. But it wasn’t necessarily about the size. It’s a common fallacy to say that if you’ve worked with 50-, 500-, or 5000-person teams, then you can handle it all. That’s bullshit,” he says. “It's not about the size of the team, it's about the state and context of what they're going through, and the set of considerations facing a seed-stage startup are incredibly different.”

In Soni’s experience, these four challenges were the most surprising — and most difficult — adjustments he had to make as he transitioned from high-profile positions at large companies to startup CEO.

1. Get comfortable under the cultural microscope.

Many first-time founders report that they underestimated the magnitude of taking up the mantle as startup CEO. For Soni, it was no different, although he didn’t feel out of his depth in terms of the functional expertise required to run a company. For him, it was more personal.

“What’s hard is that you truly have to be the best version of yourself. If you want to have any shot at creating the kind of organization you want to build, every step you take and comment you make is absolutely critical,” he says.

As an early-stage founder, I have never felt more observed. But that’s also energizing — I’ve never felt so challenged to be a better person.

Of course, companies such as Flipkart, Google and Motorola are pressure cookers of a different sort, with thousands of employees watching a leader’s every move. But for Soni, the difference at a startup is palpable.

“When you have thousands of people around you, you could walk into a room and people know you're showing up to do something. You can make quick decisions. You have a heavy hammer that you can wield,” he says. “At Google or Motorola, I could actually bang my hand on the table and say, ‘No, we're not going to do that. Let's move. This is where we're going to go.’ But if I did that at Suki, I'm giving permission to the five other people in front of me to do that in that same room with other people. That’s what our culture is going to be.”

For many, shaping culture at a startup seems easier because it's a clean slate; at large companies, changes require a slower turning of the ship. But in Soni’s experience, there's a common current between the rough waters that companies of all sizes are bound to encounter. “Whether it's at a big company or a small startup, there are only three reasons culture breaks: A bad actor is promoted, a good actor is overlooked or leaders aren’t exemplifying the culture themselves. Everything else is just a side effect,” he says.

2. Don’t look down — there’s no safety net.

According to Soni, the challenge of leading a 500-person org and building a 40-person team weren’t much different in terms of intensity and stress. But he has found startups stakes to be much higher.

“In big tech, you only think the stakes are really high. No question there are some tough calls, but you have enough buffer, support and craft to get by — there are fewer chances of disaster striking. If you make the wrong product decision, it’ll most likely be fine. Somehow, people will pick it up and we'll figure out a way to bounce back,” says Soni. “But at a seed-stage startup, the stakes are actually unbelievably high. If you make the wrong product decision in a small company, you're dead. It's over.”

It’s not just a matter of product either — risk is raised on the people front as well. “The five people in some corner of the company that got frustrated and left, because you made a decision they didn't like? That’s not as relevant if there are 15,000 people,” Soni says. “But in an early-stage startup, that would be catastrophic. Every single person is a measurable representation of your entire company. That weighs on you in a different way.”

3. Drink from the firehose of feedback and swallow the humble pie.

The transition to leading a startup has been a humbling experience — and Soni isn’t afraid to pull back the curtain. “You're a nervous wreck many days. Some days it's hard to sleep because everything looks like an existential crisis and then you spend all night thinking about it,” he says. “You're already doing a lot of emotional state management, and on top of that, you’re getting intense feedback from every direction: your investors, your team, your customers, your family.”

That’s because everyone has a point of view on what the CEO of a not-yet-successful startup can do better — and they also have the access to say it directly to the founder’s face. “You might have had 50 thoughts on what Sundar could’ve done better at Google, but he’s the CEO of this successful company so maybe you kept it to yourself. Or you didn’t even have the ability to tell him directly. But Punit hasn’t proven himself yet, and I’m sitting right here in this conference room with him, so I might as well tell him,” Soni laughs.

As a founder, you dwell endlessly on all the things you don't do well. You also have to swallow the humble pie quite a few times — nobody gets more feedback than a startup CEO.

4. Hire fellow founders — and be the friend convincing the candidate not to join a startup.

Counter to conventional wisdom, for Soni, the hardest part of startup hiring isn't convincing people to join. The best candidates — the ones who have the miraculous combination of skills, drive, and belief in the idea — often don't need convincing. But they’re difficult to find.

“What’s hard about hiring at early-stage startups is sifting through the variety of people who show up at your door to find the ones with common motivations. For the first 40 to 50 hires, hunt for a founder mentality,” Soni says. “I don't need employees. I need fellow founders who care deeply about the company and are invested in making it work. As an early employee, you need a similar level of humility, tenacity and passion, and financial preparation — a startup will never be able to pay the kind of money you could get elsewhere. Every time I find someone that clears those hurdles, it’s better than adding 10 employees who don’t feel that way.”

Interrogate whether an early-stage company is the right fit for you — just as rigorously as if you were founding the startup. The very same rules for mental health, finances, network, and passion for the problem apply to the first 40 employees.

When he interviewing candidates, Soni typically spends an hour sussing these qualities out. (For more senior hires, it can be more than five hours of conversation over meetings, dinner and long walks.) During those chats, he uses these tactics to make sure there’s mutual fit:

STEP OFF THE DIVING BOARD INTO THE DEEP WATERS OF THE UNREASONABLE

By all accounts, a larger company is the safer bet. It provides stability and scale in a way that makes it hard for fledgling startup to compete. Still, many future founders and early employees alike feel compelled by the irresistible pull of building something from scratch. For those looking to land on their feet in the startup ecosystem, take the time to prepare for the trek. Vet and validate your idea by focusing on go-to-market and the user’s needs, not purely on the product you’re itching to build. Hold off on fundraising until you’d feel ready to pick up your own checkbook. Be conscious of the cultural microscope and make fast friends with feedback. When hiring, find employees with a founder mentality by trying to convince candidates not to join. And above all, recognize the romantic streak of the entrepreneur’s journey.

“The most enjoyable moments of building startup are when you can see the pieces start to come together, when strategy, careful diligence, a humble and passionate team, and that dollop of luck all converge. But you can’t see that before you set off, you just have to take the leap of faith that it’ll all be there on the other side,” says Soni.

“And much like that moment before you dive into ice cold water, your mind resists that first step. It’s not logical. You're putting yourself, your team and your family through a lot more stress in exchange for very uncertain outcomes. When I was on the edge of that startup diving board, I kept returning to the George Bernard Shaw quote, that all progress depends on the unreasonable person. So if you’re mulling over a similar leap, here’s my advice: Don't be afraid, the water’s fine. Get out there and start something that might grow and make things better, one small unreasonable dent at a time.”

Photography by Brandon Smith.

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