Category Archives: Focus

The 5 emotions you go through as a #startup founder

I love tinkering and trying to do new stuff. It helps me figure out what entrepreneurs are going though. Whether it is learning a new language (Javascript again), a framework (Angular.JS) or new technique to get customers (Instagram FTW). Some of these projects take a few months and others a year.

For e.g. we are trying to build a periscope camera to help you take photos when you are a concert and are not tall enough or have arms that are not long enough to take them. This will be connected to your smartphone so you can look at the lens from your phone before you take the photo.

This project was my attempt to launch and manage a kickstarter campaign. We have 2 college students who have the capability to build the Raspberry Pi  based controller and I was the marketing and kickstarter campaign guy.

There’s a point in time when you fantasize about these side-projects becoming your “$19 Billion exit”. Then reality hits you daily every hour. Even if you have cofounders, you will realize quickly that being an entrepreneur is a long and lonely journey. That means you will have several conversations with yourself.

I tried to capture my own “self-conversations” or “selfies” over the last few projects to understand the moments of doubt, fear, exhilaration, stress, joy.

Lets start with the idea. Most people get exhilaration, but I get doubt as well. It seems to me that having listened to 1000’s of ideas as a judge, VC and investor, there are no new great ideas any more. Then again, if you are unable to sleep at night and want to write down, code or document all your thoughts, this is the best stage of emotion.

Then you get to joy – for me that comes from a shipped product (call it MVP, beta, alpha, anything). Not necessarily the point when customers or users are using the product, but just when you get it “out there”. The time when you can declare on your FB profile or on your Twitter stream that “Product X is live” or “Launched Product X”, followed by a call for people to try it out.

Fear hits next when you either a) get a lot of users and many complain on Twitter or a Blog post you have written that they dont “get it”. Most people rarely get version 1 of anything. You as a founder tend to then worry about whether all the time and energy you spent over the last few weeks / months / years was even worth it.

Stress comes after that when you try to pivot and change multiple times to figure out “product market fit”. The stress comes from your own internal battles to tune, fix, change and modify your project in a race against time to keep your “self funded” project from dying.

Finally this stage ends with doubt – on funding, market, customer validation, hiring, investments, a whole entire host of self critical analysis and paranoia that results in hopefully a finish that comes back to exhilaration – of the funding round, the customer traction or a new, smart hire.

Going by the numbers in my own entrepreneurial network, I’d say exhilaration post these 5 emotions is on the rise. That’s a good thing. A very good thing.

Is it a bubble? I have been asked. I usually reply – Who cares.

There’s an “orgy” going on next door (Silicon Valley) we are busy arguing the size of “condom” we are trying on. Dive in, the water is warm.

When does serendipity play a role and when does it not?

M. E. Graebner describes serendipitous value in the context of the acquisition of a business as “windfalls that were not anticipated by the buyer prior to the deal”. source.

As the new buzzword in the startup world is serendipity I thought I’d take a few minutes to share the fear I have of many folks engineering serendipity.  Put many interesting (or intelligent) folks in a room they say and serendipity happens.

I do though unfortunately feel many folks are taking it to the extreme. Given the many conferences, meetups and events that occur for startups, I am sure its very tempting for entrepreneurs to make sure they are at all of those meetings, to ensure they dont “miss out”.  If you are however meeting the same people again and again and doing the same things, talking about the same 10 startups, there’s little room for serendipity.

At most startup events, I see the same folks who make up 50% (increasingly) of the audience both on the investors side and the entrepreneurs side. While its good to see many familiar faces, I am doubtful that there’s much serendipity and goodness that will come out of it.

As an entrepreneur the one thing you have on your side is time, besides your ideas and intentions. I dont believe you can really waste any time and much worse, attend meetings just to make serendipity happen. I would highly recommend a very strict discipline of attending events that you believe you will have a good chance to get something done, and then hope for more serendipity to happen.

If your sole purpose of attending events is to make magic happen just because you are there, then you are going to likely waste more time and get little done.

My discipline will beat your intellect

I meet 4-5 new entrepreneurs every week as part of my office hours on Go-to-market help for young startups. Most are based in Bangalore, but surprisingly some are from other parts of the world (Chennai, Singapore and Estonia, even, via Skype).

I have an observation about work ethic that I wanted to highlight among startup entrepreneurs from various parts of the world.

Most every entrepreneur will tell you they work extremely long hours. That’s par for the course. Some “older” entrepreneurs (usually over 35 years of age) will share their ability to “strike a balance” between work and life. Practically speaking (I hate to break this to them) that does not exist in a startup. If you have that balance, you are not serious enough about your startup.

I understand they have families and kids, but I have come to the realization that both smart work and hard work are necessary (but not sufficient) to run a successful startup.

For purposes of this post lets define success as a company that’s growing significantly and rapidly, but does not have an exit yet.

The difference between a rapidly growing startup and one that’s growing “well” is productive (smart) hard work, not just long hours.

If you mistake activity (# of lines of code, # of code check-ins, # of customer discussions) with progress (shipping product, usable and must-have features, or # of active users) then you are just doing long hours.

If you mistake milestones (funding secured, new employee hired) for achievement (# of paying customers, churn rate of existing customers) then you are just doing smart hours.

What then makes smart and hard work such a potent combination? And what really is “smart work”? And how many hours make up “hard work”?

I define “smart work” as a combination of 3 things – asking the “right questions“, having a plan and maximizing the number of experiments in unit time.

I define “hard work” as the most amount of productive work time, with limited to no distractions and ability to do it consistently, for years (not bursts of weeks, not months and certainly not just for a few hours).

Lets look at both smart and hard in detail. Smart, first.

The smartest people I know have learned the art and science of asking the right questions. They usually start with asking a lot of questions, and having literally, no or very few answers. Each answer leads them to more questions. Asking the “right questions” is what they derive from experience.They have assumptions that need validation, hypothesis that need testing and results that need to be measured.

They are also willing to conduct a maximum of 2-3 experiments and have a DIY (Do it yourself) approach towards conducting those experiments to see if their assumptions and hypothesis were valid.

Finally they have a plan to approach their experiments. Not just a “lets try this and if not lets try that”. They rarely “wing it”.

Its very easy to spot smart teams. They have a sense and measurement of what “Continuous Visible Productivity” is. They come to me with a list of 2-3 questions that they want to address in a meeting. They dont just come to the meeting and pick up the whiteboard and start to “brainstorm”.

Now lets look at teams that work hard.

Hard working teams dont ever mention “how many hours they did put in last week or yesterday or that they hardly got “any sleep”. They realize and are aware of their physical limitations and are usually well within those limitations. Rarely do I hear from them “We work the hardest of all the teams” or “We have not slept for 2 days”. They keep looking for time they can cut away from unproductive work to do more questioning, experimenting and planning. In other words they dont brag about their long hours. They assume its a given.

Hardworking teams also tend to compartmentalize very well. Some people call this “bucketing” or “chunking”. Just because they work hard, does not mean they dont give their brains a rest and goof off for a while. Rather, they “compartmentalize” their goofing off or exercising to derive the benefits of a relaxed mind and body.

Finally hardworking teams are consistent. They show up day after day, week after week and go through questioning, experimenting and planning with rigor and consistency.

I realize a that being smart at work and working hard as I have laid out is extremely difficult. In fact its rare. That’s why successful startups are rare.

The combination is what I call startup discipline. Which is why I firmly believe one startups discipline will beat another’s pure intellect (given that hard work is assumed) any day.

The power of active observation for entrepreneurs

There’s an awesome stand up act that Jerry Seinfeld does in his “I’m telling you for the last time”. In that he tells the audience a secret about men.

The question on many women’s mind is “What are men thinking about?” is his premise. He goes on to say “Let me clue you on to the secret women. Here’s what men are thinking.”


We are just walking around, looking at stuff.

Its pretty funny and mostly true. Its also true of most people, not just men. Most of our “thinking time” is spent thinking about nothing.


That’s such a waste of time.

What I think it really means is its not worth sharing what we are thinking about.

We are “constant dreaming” about mundane useless stuff and our thoughts wander to more useless stuff.

While we go about some daily routines, we are still thinking and less “observing”.

Most successful entrepreneurs I know have a heightened sense of observation.

They watch everything. I mean they observe at least 50-80% more than the average person.

Most non-entrepreneurs people see the same things an entrepreneur does, but they dont observe.

A technique I use is active observation. It is seeing, then asking questions. As you know, questions are the root of solving interesting problems.

To discipline yourself to constantly keep observing, you have to train your mind to look, then ask. Not keep looking and neither keep thinking.

There is a downside to active observation. Its that you are not in the “present”. Critics will point to the mind-rest that your brain needs which helps it recuperate and rejuvenate. They might also say you should go with the flow to generate great results.

I prefer active observation when I am thinking about ideas and problems to come up with which need solving.

P.S. Post a few comments on facebook, I wanted to clarify that active observation is observing then doing. By default I assume most entrepreneurs are doers. Many though confuse doing (action) for progress.

Solve meaningful problems as a startup

Back in the 90’s and better part of last decade, most of the smartest folks from the top colleges would go and work at Wall Street. Lured by high salaries and fat bonus checks, they used their wizardry to create CDO’s, asset backed securities and derivatives to create billions for hedge funds, investment banks and trading desks of large financial organizations.

We all know where that ended up – the subprime mortgage crisis.

We thought there was a turn of events when one of them started to build a meaningful startup.

That prompted Bill Gates to say

“I’d say we’ve moved about 160 IQ points from the hedge fund category to the teaching-many-people-in-a-leveraged-way category. It was a good day his wife let him quit his job”

I get a sense that, “founding an Internet startup” is the new “joining a hedge fund” in the 90’s.

We are getting an amazing number of very smart people who are joining these startups in droves and applying for incubators, accelerators, hackathons and startup weekends.

There is a massive movement of high level IQ points from old-school consulting and “IT services backend for a large Indian outsourcer” to startups. That’s awesome news.

I have attended and judged 3 startup hackathons and prototype creation sessions over the last 1 month. I am absolutely thrilled that there are so many people turning out for these events in India. Over 650 attended the Yahoo Open Hack day. It was amazing to see such a diverse group of young talented developers and programmers solve some very interesting problems.

The part we have to work on is why the brightest minds are solving the most trivial of problems.

Startup IQ
Startup IQ

I think the problem with Indian startups is they think we are in the US.

There are rich people problems (The pictures from my mobile phone dont look good, can we build a “pimp my photo” app”) and there are real world problems (how can I make sure new grads from college learn to develope real apps, so they can get a job and reduce the jobless rate).

My humble request to Indian entrepreneurs is ‘Please dont build any more “I’m bored” apps’.

I am not trivializing the need for “fun” apps.

All I am requesting is that the highest IQ folks should be working on the highest impact problem areas to aid most humankind.

The art of disciplined experimentation

Being a hobbyist is an awesome way to keep learning and test “theories” you have. Most cases, when I have a theory I’d like to prove or disprove, I’ve found the best way is to just try it out. That applies to a new product idea, new marketing technique or a new sales strategy that I have either a hunch for or have overheard from someone else.

The key part that I have learned from my experiments, is that you need a framework (or a model) to clearly outline what you intend to learn from it, what assumptions you made, what steps you took and what you learned from the experiment.

If you dont have a framework, you end up with a lot of experiments whose results might suit you at a later date, but you “forget” about those experiments.

The thing about experiments is you have to understand clearly why they succeeded or failed. 

If you do that and internalize the learning, it becomes a part of your decision making for the future. Experiments without learning is just wasting time – which is also a valid reason to experiment in itself, but you have to be clear about that upfront.

To be disciplined in my experimenting, I have found that doing one at a time suits me best. I found out from a expert in SEO about a much simpler way to track the keywords you want to rank for and a quicker ethical way (than the usual 2-3 months) to appear on the first search engine results page.

My immediate thought process was “that’s just not right” and “wont work all the time”. But it was right and it works, and the only way I would be convinced of it, was if I did it myself.

I also put a time frame for my experiment, to determine if its worth the result. Many of these experiments take several months, so doing nothing but that one experiment during that time, is hard. The results from that learning better make up for more than the time and effort.

Which is why I developed for myself a list of questions so I can be disciplined about my experimenting. These questions are fairly straightforward, but my lens for the questions is based on three criteria:

a) Will it be fun?

b) Will I learn something I dont already know?

c) What new things will I learn and where can I use the learning from the experiment?

May you be blessed enough to make a thousand mistakes once, not one mistake a thousand times

I have a good friend (lets call him Bob) who worked at a Fortune 50 IT technology company for 21 years. After reaching the top of his organization (partnerships), he then left, for a startup to head up their partnership and business development efforts. He was their first “suit” / “business guy”. The startup was funded by a very well known venture firm in Sand Hill, had 21 people (mostly engineers, product managers and the like) and a hot product in the networking (infrastructure) space. The interview and courting lasted many months, so he was confident he made the right choice.

He could not have been more excited during the first week at work. There was creative energy and fresh thinking daily, new and yet unsolved problems that had no obvious solutions and he felt he was finally “learning again”.

In in the 2nd week the cofounders and he had a catch-up lunch, when they told him “they needed to go another direction and his position was to be eliminated” and they’d like him to leave. No other reason was given, but just that they were not ready for a BD person at this time, since the company was going to pursue another route.

I recall him telling me over lunch a few weeks later, when he mentioned that he was not totally shocked, but it surprised him for sure. We did some Monday-morning quarterbacking and figured it must have been either his inability to fit into their “culture”, which was very developer-centric or his relatively higher salary.

A few years went by and he continued to be friends with the co-founders and met one of them for a catch-up lunch.

The conversation was enlightening for sure. The co-founder was more candid and particularly said “most of the engineers said the amount and breadth of experience that my friend possessed was narrow and limiting”. Which shocked Bob, since he had really “21 years of experience”. He had dealt with all types of ISV‘s – small and large, had experience with all the system integrators, from consultants to outsourcers and had connections at every level.

The cofounder then said “Yes, but you did practically the same thing for 21 years, not 21 different things in a year”, which skewed your thinking to solving every problem literally the same way.

Bob was shocked for sure, but he took it in stride and in the meanwhile had started his own BD consulting company, helping many startups navigate the large ecosystem of partners.

Over the next 2 years of his consulting he claimed to learn a lot more than he had in his 20+ years at the F50.

What did he learn that he did not know before?

“I found more ways I could be wrong and more mistakes I made daily” he said. “With a large brand name on my business card, those mistakes were largely ignored. They were a lot more magnified when you are dealing with others who now have that large brand name on their business card.”