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Avoiding the Downside Vs Achieving the Upside

How to achieve success by focusing first on not doing the wrong things than doing the right things.

For the past few months, I have been taking Tennis lessons. It’s a group setting and all students are at the intermediate skill level. Last week, during a typical drill session, all of us were hitting the ball into the net more often than hitting it across the net. Finally, the coach paused the drill and advised us –

“Just try to hit the ball across the net. It doesn’t matter if it’s IN or OUT. If you hit it across the net, there is a 50% chance that at least it will be IN. And there is another 50% chance that your opponent might make a mistake. So you have a 25% chance to win a point.

But if you hit the ball into the net, there is a 0% chance you will win a point. Your opponent doesn’t have to do anything to win points. She just needs to wait for you to continue to make mistakes.”

Unlike professional players, who play and place their shots wherever they want, amateur players make endless mistakes of hitting the ball into the net. Professional players win points. Amateur players lose points.

As our coach advised, to achieve success (i.e. to win a point), avoiding the downside (i.e. not hitting into the net) is probably more valuable technique than achieving the upside (i.e. hitting across the net and IN the court).

It is a step by step journey. In every step, you first try to avoid your downside and improve your chances of moving to the next step. The better you get at avoiding your downsides, the longer you stay in the game, and the closer you get towards your destination.

As you get better at avoiding downsides, and as it becomes the skill, you transition from being an amateur to being a professional. And when you become a professional, you start controlling your shots and focusing on achieving the upside.

As you begin the journey, at every step, it is quite clear what downsides you should avoid going to the immediate next step compared to what upsides you should achieve as it becomes apparent very sooner what is not working than what is working. The downside always looks clear. The upside always looks hazy.


As a startup founder, I can also correlate this advice on how we should run our business. The step one is always about what to avoid i.e. what not to do in your business to reduce the risk.

Some examples of things I carefully avoided since we started Avoma

  • not starting a company without co-founders
  • not jumping to building a solution without extensive customer research
  • not picking up a small market, etc.

I believe to win in the hyper-competitive market, you simply need to figure out a way to stay longer in the game. As long as we avoid making stupid mistakes of burning cash too quickly, building products that no one wants, etc., we will keep increasing our chances of winning in the market.

As long as you systematically avoid the downside in your life, you will continue to increase the chances of achieving your desired success.

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12 Questions to Ask Before Starting a New Business Venture

A framework to choose which problem you should solve

Yesterday I met few friends after many years. After everybody sharing their whereabouts, it was my turn to share what I’m working on. I explained I’m working on a new venture and also shared the details of the problem we’re solving. The first question one of the friends asked was — “why did you decide to solve this problem?

It was a great question. As they say, as a startup founder, you should be able to answer these 3 questions with high clarity and conviction –

  • Why this? (Focuses on problem statement and opportunity)
  • Why now? (Focuses on market and technology landscape)
  • Why you? (Focuses on founding team)

The good part was, I had thought a lot about why I want to solve this problem from various perspectives, so it was easy to answer my friend’s question.

So I thought I should share a framework with you all that I used to decide which problem I want to solve.

As mentioned in my previous post

I researched and brainstormed a couple of problems extensively, discussed it with other people too, and eventually decided to solve a problem that I faced every single day in my professional life as a knowledge worker, and is also applicable to pretty much most of the knowledge workers in the world.

I want to fix the productivity and information loss problem that happens during every “meeting” — the necessary evil of a corporate life.


While it was a simplistic overview of why I picked up the problem that I’m currently working on, here is a list of questions I used to choose the problem I want to solve and start my next business venture —

  1. Do I personally face this problem? If yes, do I face this problem very frequently and how frequently?
  2. Do other people also face this problem? If yes, how many such people exist? Is it a very large population?
  3. Do I have the basic understanding of the problem and the solution domain?
  4. Is there a lot of progress happening in the larger space of that domain?
  5. Do I have initial thoughts on what will be the differentiation compared to competitors?
  6. Is it a hard problem to solve such that it will not be easy for too many competitors to enter into this space?
  7. If I make it affordable and at the same time deliver high value, will people pay? If yes, who will pay and how much will they pay?
  8. Will a single user receive a value from this solution or will it require more people using this service (e.g. entire team or organization) to receive basic value?
  9. How will I sell this solution? Can I sell this using bottom-up B2C2B model or will I need a typical top-down enterprise sales model?
  10. How will I distribute this solution? Are there any viral/referral distribution opportunities? Are there any platforms/partners that I can integrate with to distribute this solution?
  11. Do I believe by solving this problem, will I be making a positive impact in many people’s lives and the world a better place?
  12. Finally, if I fail to solve this problem, will I learn something new that will prepare me for the next wave/demand in the technology space?

The current problem I’ve decided to solve met all above requirements and had very compelling answers for each of the question.

I hope this framework and a list of questions will be useful to you too to choose your next business venture.


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Starting up… a new chapter

Today is my birthday. Birthdays are generally a good milestone to start something new, to have new resolutions and goals, to reflect on the past and think about the future — very similar to the beginning of a new calendar year.

Today is that day for me. I’m starting a new chapter of my life — one of the most important chapters of my life for the next several years — I’m starting a new company.

A day before y’day, I resigned from my current employer, [24]7 and jumped off the cliff again to start a new venture.

4 years ago, my co-founder and I had sold our previous startup Shopalize to [24]7 Inc. As a part of the acquisition, I joined [24]7 and worked there for the past 4 years. During my stay there, many people (friends and acquaintances) used to ask me when am I starting my next startup?

As they say, once an entrepreneur, always an entrepreneur. So their question was quite valid. But I didn’t have a satisfactory answer. I knew it was not going to be “soon”. Very honestly, it was partly because we had some payouts over the period of 4 years, but largely also because I didn’t want to rush into a startup rat race for the sake of doing it and because it’s a fad.

While I had to wait there for 4 years for the full payout, I enjoyed every bit of this period on both work and personal fronts. Overall I had fun working at [24]7. I enjoyed working with some of the smartest people, built some great relationships, learned a lot of about Enterprise space, built some cutting edge innovative products, failed in getting traction for some of the products and made some mistakes too.

One of the most fulfilling reasons I enjoyed working at [24]7 is — I was able to contribute and make a direct impact in the company’s strategy and vision. It was a full package experience — I not only learned what to do in my next company but also learned what not to do. But overall, it was a great experience.

But for the past 6 months or so, I started feeling plateaued. I wasn’t able to make the progress I wanted. I wasn’t learning something new. And at that moment, the decision became stronger to start something new on my own and accelerate the learning process in pretty much everything.

Once it was clear I wanted to start my venture, I didn’t have a shortage of problems I wanted to solve. The question was — which problem should I pick to solve — and dedicate the next several years of my life for it.

For the past 3–4 months, I researched and brainstormed a couple of problems extensively, discussed it with other people too, and eventually decided to solve a problem that I faced every single day in my professional life as a knowledge worker, and is also applicable to pretty much most of the knowledge workers in the world.

I want to fix the productivity and information loss problem that happens during every “meeting” — the necessary evil of a corporate life.

I don’t hate meetings. In fact, I love them — but when they are productive. So much knowledge gets shared, so much progress is made, and so much alignment is achieved when you have good meetings.

But there is a downside to it the way how meetings are getting conducted today. So much of time is wasted and so much of knowledge that gets discussed in the meetings gets lost. And I hate that part. And that’s what I want to fix.

I’m teaming up with few other people who are equally passionate about solving this problem. It’s a hard problem and it will take many years until we achieve our final vision. But every attempt to reach towards that vision will be worth taking to make a positive impact in knowledge worker’s life.

We’re barely getting started, so the more details will get shared very soon and very frequently on this blog. So stay tuned…


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