Prateek Dayal

Breaking the silence one random blog post at a time

7 Things I Have Learned by Doing Startups for 7 Years

I have been fortunate to be doing startups full-time for about seven years now. I say fortunate because it’s easy to quit and move on. Financially and emotionally, startups can be challenging and require almost a mad belief in the early years, while you are still figuring out what the heck they are all about. But like most things in life, you start seeing the point of them after you have done them for a while. I feel the urge to write this blog post so I can look back at it seven years from now and compare notes with the future me. Also, when I say ‘you’ below, I really mean ‘I’ (can it be any other way?). Before I write down what I have learnt, let me briefly talk about the three distinct phases of my (startup) life

Chaos and Confusion Era (2007 – 2010)

I started my entrepreneurial journey with Muziboo (which we finally shutdown this week). It was my first experience in building a product that other people used. Eventually 600K users signed up for Muziboo uploading a total of 250K tracks and posting over a million comments. For most part in this phase, I was confused about what was going on. I got a lot of contradictory advice but if I think about it, no advice could have really helped me. I had to spend some years and figure this out on my own. During this phase I felt like a rebel without a cause. My key takeaway from this phase was to build something you can use yourself everyday (Muziboo didn’t fit that profile!).

Build a Company, not just a Product Era (2011 – 2013)

After Muziboo, I knew that I wanted to build a company, not just a product. I was very inspired by companies like Balsamiq, 37Signals and Github. I wanted to build a culture of great engineering. So when I started SupportBee, I used my skills from Muziboo to focus all my energy on our engineering culture. I think I largely succeeded in building what I had imagined. SupportBee is a great place to work and I am incredibly proud of the team and the workspace Avinasha and I have built together. Remote work is a big part of our work culture and SupportBee set me on the nomadic path and I spent a good part of these three years in Chile and Vietnam. I also traveled to Cambodia, Singapore, Indonesia and Hong Kong and some cool spots in India (including the beautiful Kohima, in Nagaland). My key take-away from this phase was that it if you want to create an outstanding company, you have to work with the great people and put all your energy in enabling them to do their best.

Who am I and What the Heck am I doing Era (2014)

In 2014, I played a relatively passive role in SupportBee. I felt quite burnt out after running companies and going through the grind and decided to take it slower. I spent three months in Vietnam, including a quiet three week phase on a remote island. It gave me a lot of time to think about life but I still felt burnt out and un-inspired when I got back to India. That’s when I decided to move to San Francisco for a few months in search of some answers. My key take-away from this phase is that if you need mental clarity, it’s going to cost you money (in terms of missed opportunity, time and real money) and that it’s worth it.

So that’s been my life in the last seven years. Here is what I have learnt

Three years to learn a domain

Probably because I started up very early on, I didn’t have much domain expertise in anything (including living life). Three years after starting up on Muziboo, I finally understood what I should have been building. Three years after starting up on SupportBee, I understood what the domain of support software is all about. Running a company for a few years gives you a lot of data points. You see tons of use-cases and then you can sit down and come up with a model that can coherently address most of them. It’s no wonder that some of the best companies in the world are built over half a decade or longer. It’s worth noting that I bootstrapped all my startups (which means we could not spend money on some experiments back in the days) and so my timeline may seem off to some of you.

Importance of keeping it sustainable

Following from my last point, if you burn yourself out in the first few years, then by the time you get to a clearer understanding of your domain you might not have the energy left to start afresh. It certainly happened to me. I now know first hand that entrepreneurship is a lifestyle. Keeping it sustainable is the most important thing. It’s important to not overly romanticize the grind and 80 hour work weeks.

More like an Athlete, less like a Hacker

I have realized that being a startup founder is like being an athlete. You need to perform consistently and that comes from a disciplined life. That’s why they call this a lifestyle. Not because you have to work all the time but because what you are doing when you are not working is as important. In my opinion, consistent performance trumps short unpredictable bursts. For me consistent performance comes from understanding myself well, crafting a life that helps me stay in the zone and staying mindful of how things are going. Understanding this has helped me find a new love for endurance sports. It’s a great way to train your mind and keep yourself fit.

People skills don’t come naturally

This one took me by surprise. I have always been a pretty good individual contributor. I somehow made the mistake of assuming that being a good team enabler naturally follows from that. Well it doesn’t! Thanks to my buddy Miles for a discussion we had in the heritage city of Hoi An earlier this year that got me thinking more about it. People skills can’t be learnt by writing code in front of a computer. Ironically, the CEO job is a people job. You interact with your team, customers, investors, press and a lot of other people. You need to get really good at understanding different people, compensating for your bias and making every relationship a mutually beneficial one. These skills are learnt on the road, during travel and in other life situations. Not just in the office. Like anything else, if you want them, you have to consciously spend time on acquiring them. I have huge respect for CEOs that manage teams across different cultures and regions. Understanding people in your home country is hard enough and when you are dealing with people from many countries, it gets exponentially harder.

Don’t be the bottleneck in your company

It sorta follows from my last point. As a CEO of a small company, it’s easy to be the limiting factor in your company. You can hire the best people and create a great environment but it’s easy to let your personal bias and limited thinking on issues limit other people. There is no easy answer to this one. Staying humble and listening to others are again skills that you have to consciously pick up. Traveling and living in new environments is a great way to shake up some of your deep rooted assumptions about people and life. The bottom line for me is to stay aware that if I want to hire the best people and push them to be better, I need to keep putting myself in environments where the same is happening to me. In many ways, that’s what I love the most about being in San Francisco. No matter where you look, you find incredibly talented and passionate people and that push you to be better at whatever you are doing – from biking to doing companies, from music to partying, from hiking to tripping you always find someone to inspire you here.

Changing your relationship with failure/mistakes/not knowing

Long back, as a kid when I moved to a new city and school, I hung out with some friends and picked up a bad habit. If they found out that they didn’t know something or had made a mistake, they would get very defensive. This robbed them of the opportunity to get better. This handicapped me for a long time. In startups, you are always doing things and making mistakes. You are constantly learning what you don’t know. If your reaction to that is to be defensive, you have a problem. You are slowing your growth down. After I realized this, I worked consciously on changing my reaction. If you surround yourself with great people, you will constantly find yourself falling short of your (and their) expectations. You want to look at that as an opportunity to learn something new. If you make this mistake as a CEO, very soon the rest of your company would be doing the same (since culture self re-enforcing).

Mindfulness is the key to sustainable development

Finally, the most important thing I have learnt in the last seven years is that mindfulness is the most important asset you can have. If you know clearly what’s going on, you can fix it or improve it. If you have an incorrect reading of what’s going on, then no matter what you do, it is going to give you sub-optimal results. Before you can go out and build a great company or help other people achieve their potential, you need to become a fully aware of what’s going on in your own mind. To me this clarity is priceless. To most of us, it doesn’t come naturally. It takes time and practice to become and stay mindful. Just like any other skill, you have to believe that it is going to help you and then work on acquiring it. It’s not going to fall in your lap! Being mindful is not something you can decide to be and start being. It requires a commitment to practice and discipline. I believe that meditation is Life Skill 101.

I am thankful to Avinasha and the rest of my team that I could take a lot of time off this year to put all the data points in my life in perspective and build up a model of what’s going on. I spent a significant part of this year meditating and finding answers to my questions in deep silence. To me, all the hard work of the last seven years has been worth it. I could not be happier running a privately owned company that gives me the space to understand myself better. I hope to create the same exploratory space for everyone else in the company in the coming years. I look at a great company as a playground where smart and motivated people can learn more about themselves and their relationship to others. After all, what’s more important than understanding yourself and being happy?