Outliers

Entrepreneurial journeys mean different things to different founders. For some, it’s a way of creating wealth. Many others do it to achieve their “change the world” ambitions. But at its core, entrepreneurship brings a deep personal transformation. Past Outliers episodes with Kailash Katkar, Aneesh Reddy, Manav Garg and K Vaitheeswaran are among conversations that underscore the personal transformation of entrepreneurs while building their startups. For Sanjay Parthasarathy, a Microsoft veteran who quit the company to build Indix, an AI-powered catalog for all of the world’s products available online, entrepreneurship is all about patience. And what taught him patience? Running. “I used to play cricket, squash all kinds of sports. Now, I don’t play any sport, but run. Running is the ultimate sport for patience.” “A job at a company like Microsoft or any large company is about career development, much more outward focused. Whereas a startup journey is much more about character development and is much mor

Sunil Abraham of the Centre for Internet and Society (CIS) has been a digital warrior much before online privacy and data security became fashionable battles to fight in India. Abraham founded CIS in 2008 and established the organization as an important voice for explaining privacy in the social, digital age in India. Over past decade, Abraham has questioned projects -- most famously, Aadhaar. Many in the country, especially those in the technology ecosystem, have found him difficult to comprehend. And that has a lot to do with the ironies he lives with. For instance, despite being a vocal critic of Aadhaar, he counts Rohini Nilekani -- wife of Nandan Nilekani, architect of the citizen ID project and a passionate backer -- among the top donors at CIS. Then, around the time there were raging battles against Facebook’s controversial Free Basics program, which many argued violated Net Neutrality, there were different views within CIS. “People would ask what’s the CIS position on net neutrality,” says Abraham

What do Dropbox, Spotify and DJI have in common? Great founding teams, obsessive focus on details and, of course, their core products. Another common factor across these and several other successful companies of this decade is venture investor Sameer Gandhi who’s now a partner at Accel. (Disclosure: Accel India is the lead investor in SourceCode Media, the owner of FactorDaily). Over past two decades, Gandhi has had the front row seats in some of the most important startups. He’s also sat through “the situation room” at these companies. “Founders are the spiritual core of their startups,” he says. Successful founders aren’t afraid to go get people on board who are better than them in certain areas “I talked to one of my founders at one point in time. He was running the company as a founder—very inspirational,” he recalls. “I told him to come back as the CEO after a break and not the founder.” According to Gandhi, it’s this transition from being a founder to a great CEO that makes startups such as

In March this year, we published an Outliers podcast with Ryan. it also gives you a sense of how long we’ve been working to get these conversations:). We’re sharing it again as part of “How AngelList works” story to give you a complete inside view. In many ways, Product Hunt completes AngelList’s quest to become the one-stop platform to help startups focus on their core product and not bogged down by funding, hiring needs. From a small email list launched in November 2013 by Ryan Hoover, Product Hunt has now helped discover over 100 million products with more than 100,000 new product launches on its platform.

With Naval becoming the chairman and moving away from day to day running of AngelList, Laws has perhaps the toughest job in the startup investment world. For many, it’s difficult to even think of anyone else as the face of AngelList. It’s a challenge that Naval himself recognizes. Globally, AngelList moves about $175 million every year into startups, which is about 600-700 startups annually. And more than have of them use AngelList for their hiring too, according to Laws. “There is a misperception that we make it easier for startups to raise money. Not any more likely that you will get to “yes” if as a startup you’re using AngelList. That said, the time that you spend to get to the same answer you would have got any time…..that’s a lot less,” says Laws. “Same thing for hiring. The idea is to make that time much smaller proportion of the total time spent to get to a good match.” “The biggest challenge for us is that people think AngelList is a place where if they go, suddenly the startups get funded. That’s

Most organisations have separate engineering, product and business teams. At AngelList, engineers are the owners of the product too. When AngelList started building out a product for India, Sridhara led the product development. “That doesn’t mean you have to do all that (product, business, legal) all by yourself, but it’s pretty much like running your own company,”says, Sridhara, a University of California, Berkeley graduate in computer science.

Organisations, like people, can be outliers too. Since December 2016, I have had conversations with 59 individual outliers; a journey where me and hopefully you too, have learned with each episode. With this episode of Outliers podcast, we’re kind of breaking away from the mold and expanding these conversations to companies and organizations that are outliers in the way they behave, their mission, and so on. AngelList has been an outlier from the start in February 2010 when Naval Ravikant along with his co-blogger at Venture Hacks Babak Nivi, started with a group of investors. “AngelList was started to help startups with their most difficult tasks, helping them do that with internet at scale and with the matching engine that makes it possible,” says Ravikant. “AngelList can stumble, AngelList could fall, but I don’t think that will be because technology stops being interesting. It will be because of us,” he adds. So how does AngelList keep relevant? “Relevance just means you change with the times. It’s

When he was 19 years old, Kailash Katkar started fixing calculators and even drew screen paintings for living. Then, one day, he saw a computer for the first time while repairing calculators at a bank. “I asked what’s inside the glass walls and why was it air conditioned. They said it was to keep the computer cool,” he recollects. That encounter changed everything for Katkar, especially after learning that the computers were soon to replace calculators among several other jobs. In the age when the ability to learn new skills is considered the most important capability for anyone seeking to build a sustainable career, Katkar’s entrepreneurial journey offers great learnings. From fixing calculators to writing code to fight computer viruses, Katkar’s hunger to learn new things has helped him navigate all career disruptions. As for education, Katkar hardly managed to pass 10th standard. That’s how far he went with formal education. Over decades, Katkar along with his brother Sanjay, has built Quick Heal

This isn’t the first time we’re discussing entrepreneurial journey and how it’s lonely, and filled with failures and self doubt.But unlike the do’s and don’ts in entrepreneurship dished out byexperts and mentors who have absolutely no experience in building anything. When a veteran entrepreneur such as Harsh Mariwala openly shares his biggest entrepreneurial failures and how he handles critique, the insights are far more valuable. “I can talk about my failures all this podcast,” he says. As for wealth, Mariwala calls himself a caretaker of all he’s earned in his career. “The first 25 years are about learning, the next 25 is when you earn. And the next 25 about sharing that wealth.” Please do listen in.

“Things became so bad around 2012 that one of my co-founders came to me and said I was bullying everyone around,” Aneesh Reddy, co-founder of Capillary Technologies, told me while recording this episode of Outliers podcast. With over Rs 60 crore in the bank raised from investors such as Sequoia and a secondary share sale of around $5 million (more than Rs 26 crore then), Reddy, then 25, became his own biggest enemy. “With all that, it (money and success) starts getting to your young mind,” he told me. I first heard about Aneesh’s journey at fixing his bully image over a year ago. His boldness in accepting his problems, fixing it, and sharing the story with everyone so they learn makes Aneesh an outlier. That and the growth of Capillary. Capillary now counts Walmart and other top retailers among its top customers and earning nearly $5 million in revenues a quarter currently. While Aneesh wouldn’t disclose financials himself, a person familiar with his company confirmed the numbers. Listen in to Aneesh.

After quitting his job as Microsoft India chairman, Ravi Venkatesan spent few months working with a core team of former colleagues on a startup idea. Just before an investor was about to write a cheque, he realized he wasn’t passionate enough and backed out. It was the second time he was bitten by the startup bug in his career. “Let’s say I had gone ahead and flamed out, so what, what’s the big deal? In the cosmic scheme of things, these don’t matter. What matters is you live a fulfilling life, you figure out the way you’re really going to make a difference,” he says. Ability to learn new things, to lead and not just manage and the ability to manage self, are three timeless skills and traits that can help ride through the disruption, according to Venkatesan. “The biggest obstacle to your success is you. If you look at what has been happening around the world, the number of amazing people who’ve crashed and burned because they did something incredibly stupid ranging from Rajat Gupta at Mckinsey to many o

At 59, Uday Kotak banks on his over three-day decades old business acumen in the financial services world for building the future, and keeps awake at night wondering if he will have his bank the next morning. For incumbent entrepreneurs such as Kotak, the forces of technology disruption are not science fiction anymore. In this episode of Outliers, i sit down with Kotak, who combines the old world business acumen with a sense of paranoia for the future in a way that very few leaders do. What makes him an outlier is his hunger to learn the new, new thing and still keep the faith in the core principles of financial services based on trust and risk management. Here are edited (and abridged) excerpts from the conversation. Please do tune in and enjoy the full podcast.

The first time I heard about Gourav Jaswal was some time in 2003-2004 when I was early in my career and working with technology media group, Jasubhai Digital Media. “You must meet him,” Maulik Jasubhai, the group’s CEO had told me while hiring me. And then there were legends about how Jaswal would turn obscure ideas and aimless pursuits into meaningful and impactful journeys. Finally, I met him few weeks ago when he walked into FactorDaily office one afternoon. Over past few years, he’s been running Prototyze, a new age business incubator. Jaswal is not on WhatsApp, Facebook, Twitter, you name it. But he still manages to stay ahead of the information clutter, thanks to “the human and interpersonal networks” he so passionately curates. For me, I believe more of us should learn from the way Jaswal has built and evolved with his own “human networks”, far from the clutter and pretentious worlds of Twitter, Facebook and Instagram.

Manav Garg is clearly an outlier in the Indian startup ecosystem. Coming from Moga, a town in Punjab, Garg conquered his inability to speak English and fear of failure to set a launchpad for himself. Also, he never went to an IIT. After finishing his graduation from the Indian Institute of Foreign Trade, Garg joined G Premjee Trading on its commodities desk starting with coffee in 1998. From around $50 million worth of trading, he became part of the team that scaled it to over half a billion dollars in three years. Later, in 2001, Garg started building Eka. He’s among a bunch of rare few entrepreneurs who come from core business backgrounds to build a software company. “A lot of time my wife and family ask me why I’m going to work all the time, working so hard. It’s not really about work, but it’s the mission for me,” he says. “For me, it’s a mission. You’ll always have enough to survive. I want to change the entire agricultural space in India.” Garg has also learned to use meetings over a cup of cof

Deepak Shenoy was one of the early professionals to start algorithmic trading in India, way back in 2009. It required sifting through patterns of data and using software-based decision-making systems to trade and make stock calls. While I have been following his Twitter handle @deepakshenoy for past couple of years, some of his recent writings have clearly been outliers, especially in terms of fresh perspective and incisive analysis. “How The 11,400 cr. Import Ponzi Scam at PNB Unfolded” published in February is an example of that. Shenoy, a computer science graduate from the National Institute of Technology, Karnataka, started his career as a coder maintaining mainframe computer systems during 1996-1997. Before formally launching Capitalmind in 2010, Shenoy launched two startups--Moneyoga and Agni Software. “When you are in a job, it’s difficult to harness opportunities. It’s not just being your own boss,” he says. “At some point, you start getting tempted to take up a job because of the cash flow. A

In the mad, mad world of tech, discovering the next big thing is a holy grail for everyone – from investors to startup founders looking for their next pivot and even large tech companies hunting for the disruption in their core markets. From a small email list launched in November 2013 by Ryan Hoover, ProductHunt has now helped discover over 100 million products with more than 100,000 new product launches on its platform. In this week’s Outliers, we have for you a conversation with Hoover who talks about the ProductHunt journey, its $20 million acquisition by AngelList in 2016, and some deep lessons in building communities and keeping them alive. Hoover, 31, eats, breathes and lives the ProductHunt community. “I still love what I am doing and I still see so many opportunities to experiment and grow,” he says. “I am really weird when I wake up in the morning, far too early like 4.45 am today. My mind starts turning on and truthfully, I want to get back to the bed, but my mind gets excited, starts work

Every time we spot a hugely successful entrepreneur (either multi-billion dollar exit or an IPO), there’s a rush to analyse what went behind the success and whether there’s a playbook that can be replicated to create more successful exits for startups. Everyone from investors to existing and wannabe entrepreneurs are looking for “deep insights” that will catapult their idea into the big league. If you read some of the top learnings shared by Jyoti Bansal and even listen to the entire podcast, I bet you will get a feeling that none of this is something you haven’t heard before. However, if you can learn from Bansal’s insights by contextualising everything he says against his startup journey, the AppDynamics story, and so on, there’s a lot to learn. One of the things that stayed with me since I had this conversation with him, for instance, is what he said about the kind of people he will hire for his next startups. “I will try and avoid hiring people who have been part of big exits.” This is because exits

K Vaitheeswaran’s entrepreneurial journey lacks all the fanfare, glory and gyaan that make some of the most visible startup journeys of today, including Flipkart and Ola. It’s a story that underscores how lonely it’s to be a startup founder and how ugly the lows in the journey can get. On the midnight of December 31, 2012, Vaitheeswaran opened the door of his house to find a bunch of drunk and abusive guys demanding monies his company Indiaplaza owed to several vendors. “One of the reasons we all enjoy December 31 and look forward to January is because we believe it’s going to start something new and great,” he tells me. “That day was the most depressing because all sorts of thoughts crossed my mind. I have no shame in saying the thoughts (of ending my life) did cross my mind. I didn’t even want to see January 2nd.” “How much can you really take after you expose your family to all the abuse?” “You realize then that perhaps becoming an entrepreneur is not worth anything,” he tells me. I’ve always wan

The first time I heard of LoveDoctor, a SnapChat-based counselling service for teenagers, women and even pre-teen kids seeking sex advice, I was blown away. Not just because it’s rare to find a savvy SnapChat user in my peer group, but the whole idea of serving such a real world need, unaddressed largely, fascinated me. Few days ago, I emailed Avani Parekh asking for updates about LoveDoctor and checking if she would help me explore a deeper narrative on its evolution and the road ahead. “Well, it’s not alive anymore,” she told me. Parekh who joined Sheroes last year, is now back in that discomforting zone where many startup ideas are born. She wants to revive LoveDoctor. But this podcast is not just about LoveDoctor’s future. It’s about some hard entrepreneurial lessons on building a community on a new social platform and watching it fail to take off.

Anand Deshpande, 55, and the founder of Pune-based Persistent Systems has been an outlier for nearly three decades. Since he founded Persistent in 1990, he has watched lucrative opportunities in low-end software services come and go across different cycles. Over years, he’s steered Persistent away from low-end outsourcing business towards high-end software product development work for the likes of IBM and so on. With revenues of nearly $500 million in 2017, it’s been a long, slow journey for Persistent and Deshpande, a former Hewlett Packard engineer. “It’s not so much about founders. What everybody needs to learn is how to delegate, and that’s a very tricky part for the founders because by mentality all of us believe we know how to do things, and we find it difficult to believe somebody else could do the same thing,” he says. “There’s a little bit of arrogance that most founders have, including me. How to delegate is the biggest challenge.” As I sat down with him for this episode of Outliers, I listened t