A question to all wannabes, startuppers and entrepreneurs: Does taste drive ambition or ambition drive taste for you?

In other words, Do you have a passion for Ferrari and hence want to become rich, or do you want to become rich and then perhaps buy something like a Ferrari? [1]

On a related note, a friend of mine told me about his theory about the generations of entrepreneurs:

• The first generation entrepreneur works hard and has no time or is not interested in other things – they just want to prove themselves.
• The second generation entrepreneur has the best of both worlds – having money to enjoy as well as being inculcated with the learnings of the first generation.
• The third generation onwards, it goes downhill – because they are too pampered and they don’t need to earn any money since their ancestors have made enough money for next five generations.

Do you think this is a valid hypothesis?

[1] Don’t take Ferrari literally. You can substitute it with money to travel around the world, money to buy all the books that you ever wanted to read, etc.

Update (on Feb 23): After 51 votes, there is an equal split between the poll choices! So I guess my question could not lead me to any kind of answer. Nonetheless, it was an interesting discussion. Sometimes the question is more important than the answer.

- Work -

Resolutions

Life is what happens to you when you’re making other plans. I got sidetracked by struggling to make a business. But don’t regret it for even a moment. Learned a lot about the real world. Changed from being a meek guy who liked to hide behind email to someone who has now learned to “work the room.”

Business

Reinforced, the hard way, that “you’re not here to write code; you’re here to ship products.” — JWZ

Job

Ironically, after a startup experience, I think I will be a far more cooperative person in a corporate environment, because now I realize the problems and hardships faced in each role in a company.

Psychology

Realizing that it all boils down to psychology. Understand the other person’s psychology and only then you can navigate through life.

Rationality

My new law: “Never ever assume that people have made their decisions rationally.”. People take decisions for all sorts of reasons, just don’t assume that the reason was rationale.

Confidence

Realizing that self-confidence comes from within. Everybody has their own talents. So what if I can’t code like geniuses? When I work with intensity, I can get the job done. Good enough, I think.

- Life -

Decisions

You don’t make decisions, decisions make you.

What Matters

What matters to me is force and family.

Friends

(Drawing by Jessica Hagy)

Realizing how often you lose friends that you care about. Good friendships last ~2 years only.

Real Troubles

Don’t worry about the future.
Or worry, but know that worrying is as effective
as trying to solve an algebra equation by chewing bubble gum.
The real troubles in your life
are apt to be things that never crossed your worried mind,
the kind that blindside you at 4 pm on some idle Tuesday.

– Baz Luhrmann

Pursuit

As humans, we will always be in the pursuit of something.

At the end of the day, all we want is to be missed and to know that we have made a difference.

Yesterday was my last day at IonLab, the company that I built with a few friends. It has been a wild ride but I could continue no longer. I am leaving due to internal differences on the progress and transparency in the company.

We have been well-supported in our experience, right from a Govt. of India grant to being one of the few to be selected as a TiE Entrepreneurship Acceleration Program mentee. We owe special gratitude for the people who made that happen and supported us.

But as any been-there-done-that startupper would expect, we delivered on technology, but we sorely lacked in maturity of management skills.

Simply put:

“Shipping is a feature. A really important feature. Your product must have it.” — JWZ

I can’t explain more because it would then amount to washing dirty linen in public.

Anyway, time to move on. Hopefully second time will be better!

I have been reflecting on many of the experiences I’ve had. So I thought I’d jot down the biggest lessons I learned as a startupper:

Stop reading. Start doing.

For every hour that you read, you must gain 3 hours of experience.

I read so much about entrepreneurship, although only after jumping into the startup. One and a half year later, we had made all the mistakes that those articles warned us about. The problem is not in the reading or understanding, the problem is in internalizing what you read. Wannabe startuppers read all the Paul Graham essays and say “Nah, that’s not going to happen to me, I’m going to be awesome and successful”, but when I read his latest essay What Startups Are Really Like, it felt like he crept into my head at night, stole my experiences and wrote a letter to me. Yes, really, it felt like that. But, of course, you won’t believe me. Until it happens to you.

What was the most common response from the YCombinator startups to Paul Graham?

When I look at the responses, the common theme is that starting a startup was like I said, but way more so.

Read those last few words repeatedly 6 times.

And I repeat, my warning to you is that simply reading A-Z of books and essays is not important, you have to internalize the learnings by testing it out on the field and realizing the value for yourself instead of saying “that makes sense” and forgetting about it a few minutes later.

Empathy matters

It is funny how most people will discourage you from doing a startup, and, today, perhaps because things have changed now because of all the media hype, most of my friends were discouraging me from leaving it now!

There are two aspects to this. First, read The Dip and you will know why I decided to quit. As Seth Godin says in the book, “The old saying is wrong – winners do quit, and quitters do win. Winners quit fast, quit often, and quit without guilt – until they commit to beating the right Dip for the right reasons.”

Second, as one of my friends observed, I talked to about 7 people (both acquaintances and friends) whose judgment I trusted. 3 of them sympathized and agreed with my decision and 4 of them admonished me and asked me to “hang in there.” You know what was the clincher? The first 3 had done startups themselves and the latter 4 had not. The latter 4 did not really understand the context, even though they meant well and are intelligent folks.

Imagine that a decision like this was so hard for friends-who-know-you to understand. Imagine how much empathy you should have for the motivations and work life of your customers!

Business is not a big deal, it’s only a mindset

The day I realized that I had started to think in terms of business was this conversation:

Friend: Hey, I wanted to talk to you about a gadget idea. Most phones have large storage space and bluetooth facility. Most cameras have small storage space. I have both of them on trips. I usually run out of space on the camera. So can there be a gadget similar to a bluetooth dongle that can move photos from the camera to the phone?

Me: Interesting… there is much to evaluate there (for example, I want to understand how much battery power it would eat up, which is the major concern when on a trip). But if you’re thinking about such a product, I think we should skip bluetooth and talk about peer to peer WiFi^*.

Friend: What? Bluetooth is there on every freakin’ phone out there!

Me: Yes, but by the time you build this new gadget, all the devices would have moved to p2p wifi because it means supporting only one standard. Right now, phones have to support two standards – both wifi and bluetooth which is additional hardware and headache for the manufacturers. Since p2p wifi builds on top of the existing wifi standard, it makes business sense for them to standardize on that. Comparatively, the only advantage of bluetooth, AFAIK, is low power consumption, and that factor will reduce with increasing battery life. So, in 1 or 2 years, bluetooth won’t be the in-thing, and that is when the product will be ready if you start now.

Friend: stunned silence

Me: Did I say something wrong??

Friend: You really are a businessman now.

Me: Heh

See? It’s not a big deal, you just have to learn the right mindset. Note that I didn’t say it was easy, I’m simply pointing out it’s simply a different mode of thinking, and it is doable.

I realized that doing a tech business means you should know both tech and business really well (duh). And since I’m not there yet w.r.t. tech, I’m going to stick to that as my core for the next decade. Or at least, that’s the plan. Coding is still my first love. Update: After some thought and discussions with close friends, perhaps I can contribute in additional responsibilities such as product manager-type responsibilities as well.

^* Also see What’s next for Wi-Fi?

Focus matters

A great advice I got from Muki, an entrepreneur was: “Start focusing on three things from day one – relationships, cash flow, balance sheet. You already know how to handle the rest.”

Notice he doesn’t talk about innovation, technology or all those other things. On the same note, the best explanation I’ve seen is that “Innovation is the by-product of a well-executed product”, which brings me to my next point.

“Focus” in the context of startups can be interpreted as good product management skills, which I strongly referred to in my StartupDunia guest post on the recent NASSCOM Product Conclave.

Maintain good relationships with partners, vendors, mentors, and all other folks that you meet in the course of your business. Don’t look at these relationships as opportunistic, look at it as an opportunity to co-create and learn.

Track your cash flow. Yes, you will earn millions later, but if you don’t have money now, you’ll die. You may not realize that the single highest factor why startups die is because of bad cash flow.

Don’t trivialize any aspect

Anything that is not managed will deteriorate, said Bob Parsons.

And it’s very true in this case, whether it is your legal company paperwork (yes, those stuff that you don’t want to be bothered with) or your project timelines (yes, tracking what’s on the critical path is very important, but you already knew that, didn’t you?) or thinking long-term as well as short-term, or networking with similar folks.

We, as tech people, think technology is everything and other people have it easy. I was like that. I learned it the hard way that “Easy is a term you use to define other people’s jobs.” I have a lot of respect for marketing and sales folks now. They have a really tough job, because it is about tenacity and psychology, compared to tech work which is write-once and scalable. Pop quiz: Did you really understand the signifance of that last sentence? If not, go back to my first point.

Have a sense of urgency

For every decision (and you will have a lot more of them than you realize), make sure that you do due diligence but at the same time, have a sense of urgency.

As Tecumseh Sherman said: “A good plan violently executed today is far and away better than a perfect plan tomorrow.”

Bottom-up always wins

This is the single most important learning, if I had to pick one.

Time and again, I’ve observed that bottom-up always beats top-down approach to problems. Note that I’m not discouraging you from planning, but I’m discouraging you from focusing purely on the plan. The plan is a guide to your actions, you should not spend more time on the plan vs. the actions and results!

And you can observe the power of bottom-up thinking time and again, whether it is in terms of societal change or productivity paradigms like GTD or the reason why Wikipedia and open source software are successful. As Linus Torvalds says “Software is grown, not built.” Mull that!

How does this apply to startups? Let us take one specific example: You have a new idea to solve a problem and you want to test if your idea works. If the prototype takes a couple of weeks, then you should go for the prototype. If it will take longer, how do you know that it is worth investing the time? Simple, use Adwords to assess demand for your new product/service. Same thing for doing market research.

Notice that in this example, we first start top-down by ideating and brainstorming, but then switch to bottom-up thinking once the initial plan is done – immediately jump to action by a real evaluation about the need that you are trying to solve. Then decide the second action based on the results of the first action.

How to define failure

This is how I explained failure to a friend: You walk into a new restaurant, and try the food. It can be good or bad. But you still have to pay the bill! You don’t know whether your effort is going to succeed or not, but you still have to put in the effort.

And the friend replied: The problem with most people is, they don’t want to risk eating bad food, that’s why they keep going to the same restaurant, even if they are bored of it!

When to call yourself an entrepreneur

I have this personal demarcation that I will call myself an entrepreneur when I have (1) created something new (2) made money. Until then, I’m a startupper (someone who has done or been in a startup).

This is the End

Hope these reflections are useful for future startuppers and entrepreneurs. All the best! (also see 10 things I wish I was serious about before starting a startup)

As for me, I’m cash-strapped (Didn’t I say lessons learned?), and hence looking for a job (product manager or senior technical role). Do let me know if there are any interesting opportunities out there.

The irony in this world is that “To get somewhere, you already have to be there.”

From an individual perspective:

• If you want to make money, you need to already have money.
• To get a job, you need to be one-year experienced and not a fresher.
• If you’re experienced and want to apply for a job that you really want to work on, you should already have the background of working in that area, and you should already know how to do all that the job entails.
• If you want to write a book, publisher expects you to have already written a book before.
• To be listened to, you need to be an expert, not an amateur, but how do you eventually become an expert if you’re never listened to?

From a startup perspective:

• If you want to get funding, your startup should be in a position to not need funding.
• If you want to stock your product in ezone, you should not be a 1-product company, but a 5-product company.

And on and on.

To get somewhere, you already have to be there.

P.S. I’m not condemning, condoning or approving of the situation. Just making an observation.

The world is no place for a logical/rational person.

— Swaroop C H

Two things are infinite: the universe and human stupidity; and I’m not sure about the the universe.

— Albert Einstein

A fool may be known by six things: anger, without cause; speech, without profit; change, without progress; inquiry, without object; putting trust in a stranger, and mistaking foes for friends.

— Arabian Proverb

Question for you: How do you distinguish incompetence, laziness and unprofessionalism?

“People are good and trustworthy and generally just concerned with getting through the day,” Newmark says. If most people are good and their needs are simple, all you have to do to serve them well is build a minimal infrastructure allowing them to get together and work things out for themselves. Any additional features are almost certainly superfluous and could even be damaging.”

– Craig Newmark (of CraigsList fame)

So what are there real needs?

I’m trying to (naively?) boil down all the successful software, websites and web applications out there and see if it can be mapped into as few categories as possible:

1. Communication (Social networks, Basecamp, etc.)
2. Organization (Google Docs, Flickr, Backpack, etc.)
3. Information (Content websites, News websites, Search engines, etc.)
4. Entertainment (YouTube, Nautanki.tv, Blogs/Journals/Twitter, etc.)
5. E-Commerce (Amazon, Paypal, etc.) (Category added thanks to Ankesh)

Note that the website that you use may fit into different categories in different circumstances.

The idea is to not search for a comprehensive or accurate classification.

The idea is: If you brainstorm an idea or come across someone else’s idea, can you trace it back to one of these categories? If yes, what does it mean? If no, what does it mean?

Is this a useful angle to evaluate an idea, or not?

1. Everything gets magnified. Whether it is minor differences or personal shortcomings or the multitasking required. What you think of as a small weakness, will become your biggest weakness. What you think of as a small strength, will be a very big strength.
2. It is an emotional rollercoaster ride. You can never be prepared for it. But realize what you’re going through.
3. Expect rejection. Good ideas alter the power balance in relationships, that is why good ideas are always initially resisted.
4. Shut up, make a core working version first. And get people to use it, even if you have to beg or force people. And keep iterating. After the first few iterations, you will figure out what is the interesting part that makes it work for the user. Focus on that, not on the list of features. Otherwise, you’ll end up like Zahdoo.
5. Have a plan in writing. Be clear starting from things like how long you can survive, open understanding of when each individual would want to quit, open understanding of why each person in this, etc. right up to imagining you’re going to be doing this for the next ten years, does your plan still remain the same?
6. Short-term wins are important. Psychological boosts can keep your startup alive. Plan for short-term tangible goals. And keep iterating over your plan with weekly reviews. If you don’t see progress three weeks in a row, the alarm bells should be ringing.
7. Always start with one person fully dedicated to the business side of things, especially a marketing/sales person or a product manager. Working part-time tech and part-time business is a disaster-in-the-making.
8. When you’re making a six-month plan, understand what parts are on the critical path that will make or break your startup. And make sure things on that critical path are in your control. Pay attention to dependencies on outsiders, whether they are web designers or outsourcing companies.
9. If you don’t have enough funds, find people who can fund you before you jump in, or start your own services/consultation business to keep the cash flow going. Otherwise, you’ll end up skydiving.
10. Do not be wrapped inside your own bubble. Go out and talk to interesting people, find mentors, know what is happening in the field that you are working on. You have to know where dangers for your startup lurk, and you never know where unanticipated opportunities for your startup will come from.
11. Bonus: If it’s a problem, it’s always a people problem. Learn to understanding each others’ psyche.

Let me tell you something you already know. The world ain’t all sunshine and rainbows. It’s a very mean and nasty place and I don’t care how tough you are it will beat you to your knees and keep you there permanently if you let it. You, me, or nobody is gonna hit as hard as life. But it ain’t about how hard ya hit. It’s about how hard you can get hit and keep moving forward. How much you can take and keep moving forward. That’s how winning is done! Now if you know what you’re worth then go out and get what you’re worth. But ya gotta be willing to take the hits, and not pointing fingers saying you ain’t where you wanna be because of him, or her, or anybody! Cowards do that and that ain’t you! You’re better than that! I’m always gonna love you no matter what. No matter what happens. You’re my son and you’re my blood. You’re the best thing in my life. But until you start believing in yourself, ya ain’t gonna have a life.

Rocky Balboa: Yo, don’t I got some rights?
Boxing Commissioner: What rights do you think you’re referring to?
Rocky Balboa: Rights, like in that official piece of paper they wrote down the street there?
Boxing Commissioner: That’s the Bill of Rights.
Rocky Balboa: Yeah, yeah. Bill of Rights. Don’t it say something about going after what makes you happy?
Boxing Commissioner: No, that’s the pursuit of happiness. But what’s your point
Rocky Balboa: My point is I’m pursuing something and nobody looks too happy about it.
Boxing Commissioner: But… we’re just looking out for your interests.
Rocky Balboa: I appreciate that, but maybe you’re looking out for your interests just a little bit more. I mean you shouldn’t be asking people to come down here and pay the freight on something they paid, it still ain’t good enough, I mean you think that’s right? I mean maybe you’re doing your job but why you gotta stop me from doing mine? Cause if you’re willing to go through all the battling you got to go through to get where you want to get, who’s got the right to stop you? I mean maybe some of you guys got something you never finished, something you really want to do, something you never said to someone, something… and you’re told no, even after you paid your dues? Who’s got the right to tell you that, who? Nobody! It’s your right to listen to your gut, it ain’t nobody’s right to say no after you earned the right to be where you want to be and do what you want to do!… You know, the older I get the more things I gotta leave behind, that’s life. The only thing I’m asking you guys to leave on the table… is what’s right.

– Rocky Balboa 6 movie

Reading a book is fun. If you have to do a review on the book for the newspaper by Friday, it becomes work.

Writing code is fun. If you have a deadline next week, it becomes work.

Spending time with that special someone is fun. After tying the knot and having no other choice makes it work (or so I’m told).

Calculating sports match statistics is fun. Spending the same amount of time to balance your checkbooks is work.

Is commitment the difference between fun and work?

P.S. Yeah, I had a Godin moment.

Update : After reading all the interesting thoughts by you folks in the comments section, maybe spontaneity is one of the major differentiatiors?

It has been exactly one year since I quit my last job.

The good

Things that I thought was important but didn’t turn out to be:

It has been one year since:

• I had to do something because I had no choice.
• I had a boss.
• I had to attend meetings.
• Since I have been answerable to someone.

Things that turned out to be important:

Discovering things about myself that had been previously masked. For example, discipline is about doing things even when there is no one watching you. I realized how bad I was at this, and a year later, I’ve significantly improved.

Equally important, I’ve discovered many of my strengths. And learning how to build on those.

For example, I ended up jumping in full-time into our own startup – we have three guys in our little company, and I’m learning how to leverage each of our strengths as a team. Why is this different from previous experiences? Because I was told to do things. Here, we are the ones deciding what to do and the guys actually doing it. In all this decision making, I realized what areas I have a good nose for, and which ones I don’t.

The bad

One year flew by and I don’t even know how. Definitely not a good thing.

I’m simply not satisfied with the results.

Back to the drawing board…

The ugly

It has been one year without a salary.

Thoughts

Like a wise man once said “Only when you’re truly lost do you begin to find yourself.”

This is exactly what happened to me. When I quit, I had all sorts of visions that my freedom would be exciting and I can do anything I want. In fact, the first month was exactly that and I had lot of fun. The second month was disastrous, it is amazing how depressing one can get if there is nothing to do. An idle man is a DevD’s workshop.

I started thinking about what it is that I want out of life and what it is that I can do. Even though I still don’t have an answer, I have a far better understanding of what the answer would be like, than I previously did.

I have many things to look forward to, especially some exciting things coming up with our company. Lots of things to learn. And most importantly, focusing on lots of things to do.

Still a long way to go.