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The 11 important lessons that 10 Venture Capitalists (VCs) taught me

 In the past 14 years of being a digital entrepreneur, I have met lots of VCs. And I have learnt a lot from them. Here are my 11 favorite lessons:

Lesson 1 – “Let’s see how long your entrepreneur stamina lasts.”

Who taught me this lesson?

Abhay Havaldar – Then at Draper International and serving on the board.


At the office at Kemps Corner – Off Peddar Road, Mumbai


Circa December 1998

The context:

I launched in August ’98. In December ’98, I received a call from a stock broker who said that someone from wanted to meet me.

I excitedly went for the meeting and met Ajit Balakrishnan (founder of and Abhay Havaldar. This was my first ‘important meeting’ as a digital entrepreneur, and it turned out to be an exploratory meeting for to acquire!

I was totally charged up!

Ajit asked me, “Alok, what’s your business model?”

I did not understand the question because I had not heard the term “business model” before.

Abhay grinned at me (he has a great grin) and explained the meaning of what Ajit had asked me.

I mumbled some stupidity.

Ajit looked at Abhay and said, “Alok is running a passion business. This is not for us.”

Abhay agreed and then told me, “Alok, you have something going for you. The passion in you to create c2w is awesome! Now, prove to me that you have entrepreneurial stamina to make your passion last and make a business out of this. Best of luck!”

I left the meeting crestfallen and challenged. Of course the advice imparted to me was priceless.

Abhay became a great friend and my first ‘VC’ contact. Eight years later, when I sold mobile2win to Disney, I met him and told him, “I am still running the bloody marathon.”

He flashed his zillion $$$ grin and said, “Yeah, I noticed that.”

I love Abhay for what he taught me and he remains one of my favorite VCs.

Lesson 2 – Are you a service company or a media company? Who are you??

Who taught me this lesson?

Rajesh Jog – Then Partner at eVentures India


At the eVentures office at Khaitan Bhavan – Churchgate – Mumbai


Circa November 1999

The context:

If you’ve met Rajesh Jog once, you can’t forget him.

He makes his presence felt. The big shuffle, the immaculately dressed banker, the smile and the Dara Singh handshake make their mark. Yeah, to add to the credits, my wife also thinks he looks like George Clooney ☺

I learnt this lesson in the first informal meeting I had with Rajesh around the time eVentures was investing in

Rajesh understood the contests2win business quickly. We were creating games and contests for brands. Lots of contests and games that involved lots of brands.

A little while later, Rajesh looked me in the eye and asked, “Is this a services business or a media model?”

In 1998, the reference to online media was and everyone wanted to be a ‘media’ Company.

Almost without thinking and with a bit of condescension, I said, “We are a media Company. We put content out there. Consumers come to consume our content.”

Rajesh grinned (yeah – he and Abhay have some stunning ‘Grin DNA’) and said, “Okay, just think about it.”

Now Rajesh Jog is a really jovial person and coined the words “All is well?” way before some movie came along and made it popular.

A few years ago, when he asked me, “All is well?” I replied, “Yes. It’s just that I now I understand your question … contests2win is a services play, not a media play.”

Rajesh grinned and gave me a Dara Singh handshake.

Many businesses later, I have realized what services, product, platform and media businesses really mean. Now, everytime an entrepreneur claims he is ‘something’, I remember Rajesh, his question and immediately grill the entrepreneur. I even created this PPT in honor of his immortal question.

Lesson 3 – Think Vertical, Horizontal and Diagonal!

Who taught me this lesson?

Neeraj Bhargava – Then Managing Partner at eVentures India


At the first c2w board meeting at a Cyber Café on Marine Drive (next to the Compaq showroom) – Mumbai.


Circa February 2000

The context:

Neeraj Bhargava is really intense.

He quickly absorbs everything about your business, your industry and the business model. He is like a Super Sponge. I guess it’s his sheer intelligence, coupled with his McKinsey training. (As I remember him up to 2001). Of course post eVentures, WNS and a lot more, I guess he is close to being God.

Neeraj is best seen in action in a Conference Room, with a white board and a few markers. What he draws out (charts, diagrams and strategy), leaves ignoramuses like myself spellbound.

On that fateful day, after we began speaking about contests2win, Neeraj looked at me and said, “Alok, this can easily become polls2win, surveys2win and lots more… You have a winner in 2win.”

What he said then made no sense to me. Dumbly enough, we did start a small polls2win section on contests2win that was nothing but a poll of the day.

A few years later, when mobile2win was incorporated in China, it dawned upon me – this was what Neeraj was talking about!

mobile2win China, mobile2win India, media2win and games2win later, I am a bit wiser. But Neeraj had the inspiration, vision and foresight to think vertical, horizontal and diagonal 12 years ago!!!

Thank you Neeraj for inspiring me.

Lesson 4 – Stumble, Fall, Get up and Move…

Who taught me this lesson?

Renuka Ramnath – Then Managing Partner at ICICI (Venture Team)


On the small sofa facing the piano in the Trident Lobby (Mumbai).


Circa May 2001

The context: had raised seed capital from ICICI and eVentures in 1999 and that money had been used up to build the teams, etc.

Now in 2001, we had 6 months of cash left to survive. eVentures had closed down their operations. I was desperate. I knew we had a great idea and we had to somehow survive this storm. The agenda was to beg Renuka for some more funding.

I began the conversation and rambled a bit on how great an idea c2w was and then told Renuka, “Ma’am, we need more money to survive.”

Renuka looked at me, smiled and said, “Alok, when we have children, they fall down sometimes when they begin walking. As parents, we can easily hold them, but we don’t. Allowing them to fall is what teaches them to walk.”

Renuka then left the meeting.

I was shattered and almost crumbled. Any chance of getting ‘easy money’ was destroyed. We were destroyed as we walked out. Yet something had been triggered inside.

We struggled, beat ourselves to death and survived. Almost 11 years later, we are miles ahead of those horrid times, and that advice remains unbelievably hard to beat.

The Lesson learnt was to fall, stumble, get hurt, BUT survive. And in the process, become strong!

Lesson 5 – We want to make you comfortable.

Who taught me this lesson?

Sumir Chadha – Then Co-Founder and MD at WestBridge Capital

Where? office – Tardeo – Mumbai


Circa Feb 2005


The dotcom bust of 2001 and the ensuing years had been tough and very painful.

As 2005 began, things started looking up for us. contests2win had survived, mobile2win China was in full motion and mobile2win India had started up. As a group we had proved to be the first successful “Indian Start Up Export to China”, and media2win (a full service ad agency I co-founded with KK) had also begun operations.

The buzz was back and we were in action!

The challenge facing the group was capital. The past 4 years had left us battered. We were surviving on a hand-to-mouth basis. While we had steady cash flow, there was no ‘capital’ in the bank.

Just around that time, I began meeting VCs and had the opportunity to meet with the founding team of WestBridge Capital. I met SK Jain, Sandeep Singhal (the other Sandeep Singhal is the founder of Nexus) and Sumir Chadha.

I got comfortable with SK and he visited us a couple of times.

The discussion was an ‘overall’ investment in the 2win Companies.

That day, SK told me that Sumir was in town and was happy to come over and meet me. I was delighted to meet Sumir given that most of the time he was overseas; and maybe this meet could broadly seal a deal.

In the meeting Sumir asked me about the business, what our plans were, etc. He then abruptly asked me, “Alok, what about yourself? Are you happy? How are you doing? Is there anything we can do to make you happy?”

It was a very unusual question that I had never been asked before. I cracked and almost instantly said, “Sumir, to be honest, I feel like I have worked 7-8 long years and have received nothing. I feel poor. It’s very tough.”

Sumir chuckled and said, “Sure Alok, we understand! How about we give you 500k US$ for yourself and buy some of your personal shares? Would that make you feel comfortable?”

I was stunned. I was drawing a meager salary at that time and a 2-2.25 crore personal payout seemed like a lottery to me!

I gladly accepted and was amazed to see that promise convert itself into a section in the term sheet that we received later!

The lesson I learnt was that VCs are kind. They are human and understand entrepreneurs – sometimes even better than how entrepreneurs understand themselves. They get the emotional side of people as much as they get the business and the financial side!

(The WestBridge deal did not happen because I began to fall out with my mobile2win management team and the investor team became uncomfortable with their behavior. In that bargain, I did lose out on receiving 2+ crores ☹ at that time.)

Lesson 6 – The value of 1 million US$ and putting ‘Family First’.

Who taught me this lesson?

Vab Goel– Then a partner at Norwest Venture Partners


Over a phone call at Kamini Banga’s House – Carmichael Road – Mumbai.


Circa February 2006


Vab Goel represented Norwest Venture Partners and the fund wanted to acquire my personal stake (held via contests2win) in mobile2win India.

mobile2win was in the VAS (Value Added Service business) and was a hot Company in early 2006 because it had implemented the mobile voting platform for the Indian Idol show, and the money was rolling in! Also the business seemed massively scalable.

I had a major situation with the mobile2win management team and with Norwest who came in – all documented as ‘The Toughest Decision of my life’ blog. But the lesson that Vab taught me while all this was going on, was something else.

In that phone call (he called me without intimation or appointment), Vab began to persuade me to sell my mobile2win shares and then just like that said, “Alok, do you know what 1 million dollars looks like?

I understand from the math that if you take my deal, you will personally make more than 1 million; with more to spare for your other investors.

Let me tell you that many entrepreneurs work all their lives and never see that kind of money, so if you are getting it just like this, take it. Also, remember, while making your decision on selling or holding, you should always put family first and everything including investors, later.

Take my offer and put your family first.”

I ‘had’ to take the deal, but today after 6 years I look back and really appreciate what Vab said. A million US$ is NOT easy to make. And yes, it does make you feel more comfortable about your family!

Lesson 7 – You are important. You are the entrepreneur. We are only the investors.

Who taught me this lesson?

Nandini Satam – Then AVP at ICICI Venture Funds


The ICICI Venture Funds office – Prabhadevi – Mumbai


Circa September 2006


My ‘forced’ exit from mobile2win made me hit a low note. It seemed that the BIG mobile opportunity was no longer available to me because I was also forced to sign a 3 year non-compete agreement with mobile2win, barring me to do ‘anything mobile’.

In semi-despair, I began scouting for ideas and met a couple of VCs who suggested looking at PC and Online Gaming.

One VC told me, “Alok, just quit your businesses and let your managers run them. Start a new Company and we will invest 500k US$ in it. You can keep the majority of the equity. All your old VCs need not come into this new Company. And you can experiment with all your ideas via this funded Company.”

It was bad advice and I was influenced by it.

I met Nandini Satam at the ICICI office to tell her what was on my mind. ICICI was my investor in

While I spoke my mind, Nandini listened patiently. Then she said, “Alok, we are your investors, and you are the entrepreneur! The brand 2win is yours, not ours! Why would you ever quit and walk away from what you have built over such a long period of time, just to start a new unknown venture?

Instead, start doing what you want within contests2win, and we will support you completely! We have received a decent chunk of money from the mobile2win sale (mobile2win China + India) and we can easily risk some of the money based on your vision. And then, when you are successful, you can retire us, not yourself!!”

I cannot thank Nandini enough. She was the inspiration for I got board approvals to put 1 million US$ into games2win from the contests2win bank account and we started the business.

Within a few months, after observing our commitment to the business, Clearstone funded us and we even got our 1 million $ back, as part of the deal!

To complete the story, a few months ago, we managed to impress Nirvana Ventures to invest in games2win. In that process ICICI Venture Funds did receive a nice return on its original contests2win holdings!

Nandini simply taught me that the Entrepreneur was the King of the Castle, and Kings never run away.

Lesson 8 – Why? Why is ‘what you do’ so important?

Who taught me this lesson?

Sumant Mandal – MD of Clearstone Venture Funds


At the games2win office – Tardeo – Mumbai


Circa September 2007 and December 2007


Clearstone Venture Partners had invested into games2win and we had just launched an MMOG (Massive Multiplayer Online Game) in India called CT Racer. It was Sega game that we had licensed from Sega and Hyundai.

Since this was the first of its kind of game ever in India (another Company called had launched a dancing MMOG game), there were no ‘industry’ metrics to measure what was going on. There was no way to ‘report’ the business performance of this game to investors, using established benchmarks.

I remember the two most embarrassing board meetings of games2win where I learnt this lesson. These were in Sept and Dec 2007.

Since I had done lots of research on the MMOG games and had ONLY come across ‘concurrent users’ as the measure of success (users playing together at any instance), that was the only metric, I assumed, was important.

I wasn’t thinking of what was relevant to games2win in the Indian context – I was just aping Companies in China and Korea and how they expressed themselves.
So, in the first board meeting, I aggressively presented that we had reached ’14’ concurrent players in the game. In the second board meeting I was even more proud in declaring that we had reached ‘30’ concurrent users.

I still remember Sumant smiling at me and asking, “Alok, what kind of numbers does Shanda do in China?” (Shanda was the largest games Company in China at that time.) I gulped and said, “Between 1 and 1.25 million concurrent.”

Sumant then questioned the relevance of concurrent users in the Indian context given that broadband connections, gaming cafés, etc, did not exist and hence was not a justified comparison.

I did not have an answer.

In retrospect, I should have thought of expressing a percentage of users in India that we had converted to ‘paying from playing’ and proven our ability to monetize gamers early on in India.

Sumant taught me that the ‘why’ was more important than the ‘what’ or the ‘how’.

Even the ‘when’ did not matter. This theme of introspection is an indelible lesson that Sumant has taught me. Even as we move into mobile games, Sumant urges me to try and prove ‘why’ is valuable and how to measure that, not so much ‘what’ we are doing and ‘how’.

Lesson 9 – Do you have a personal brand?

Who taught me this lesson?

Sumant Mandal – MD of Clearstone Venture Funds


At the games2win office – Tardeo – Mumbai


A couple of times in 2008


In each of my interactions with Sumant in the year 2008, he would ask me, “Alok, do write a Blog? How are you building your personal brand?”

I wasn’t writing a blog. I merely relied on my PR agency to get me featured in any media that we could lay our hands on. That was my personal brand building strategy, and it wasn’t a very predictable or well planned one.

All through 2008 I did not pay attention to what Sumant was telling me. In a quirky co-incidence, the Nov 2008 night when Obama was elected, I was in New York and I dreamt of a name called Rodinhood. When I woke up at 3 am, I registered the domain.

Then one day in early 2009, when Sumant reminded me again, I got a ‘jhatka’ and wrote my first blog (now that I read it, it really sucks ☹).

But 3 years later, the world has changed for me. Sometimes I feel that if I had not started blogging, writing and sharing, I would have been demolished by now.

The fact is – you are reading this because Sumant inspired me to start writing and sharing!

The big lesson I learnt is that sometimes VCs come to you not as financiers and partners but as Angels and Gurus – to guide you to a higher cause, beyond business, money, creating and selling companies. They come to lead you to the path that you have missed all along.

Lesson 10 – There are no rules.

Who taught me this lesson?

Karthik Reddy – Managing Partner – Blume Ventures


In the media2win conference room – Tardeo – Mumbai


April 2011


In 2008, media2win (a business I co-founded with KK) had invested and incubated a start up called ‘Hover’.

Hover’s business was to create a platform for ‘in-text’ advertising that could generate advertising revenues for web publishers and seamlessly allow advertisers to buy ‘contexual keywords’ on those media properties, via the Hover platform. The business was supposed to be a next generation of the established player in this niche industry – Kontera

There were lots of struggles in getting that business off the ground. Finally, after a lot of blood, sweat, tears and money, Hover was launched and managed to gain some traction.

A few months later, Blume Ventures invested in the business and we had the first Board meeting in the media2win office. That board meeting definitely ranks in my experience as the ‘most bizarre board meeting I have ever attended.’

In the meeting, in the middle of the regular slides, one of the Hover co-founders made an extremely mind numbing proposition. He said, “I have found a Head of Sales for our business and I have promised that person 15% of the business as ESOPs.”

At first, all the board members thought our ears had developed an infection and that we heard wrong. Maybe the co-founder wanted to say 1.5% and we had heard 15%. But the co-founder insisted that it was 15% that he wanted to carve out.

I was stunned and shocked. Quietly and keeping my composure, I tried to reason and explain the outrageousness and stupidity of the proposal to the Hover co-founder.

Just then, Karthik who was present said, “Hey, no problem! 15% is almost half of what we own (and for which we have paid lots of money), but that’s okay.

Let’s figure what the Sales Head will do. In fact, if he manages to generate X, Y and Z revenue targets for the next 3 years, I propose that WE DO give him this equity.”

The room fell quiet and I learnt an amazing lesson in my life – that when VCs are proposed the most stupid, mind boggling and unconventional deals and ideas in their lives, some hyper alert and intelligent VC like Karthik will be nimble, quick footed and smart enough to TRY and turn that terrifying moment into something that could work for them and the Company!

Karthik that day taught me ‘never to say never’.

(Hover turned sour and we returned the money received back to Blume. The business was purchased out by media2win and has been mothballed for a future release.)

Lesson 11 – Be Audacious!!!

Who taught me this lesson?

Jim Armstrong – MD of Clearstone Venture Funds


In the Clearstone Conference Room in Santa Monica – CA – USA


October 2010


I was presenting the games2win business update to the Clearstone Venture Partners top bosses in 2010. In the large conference room sat Bill Elkus (founder of Clearstone), Jim Armstrong and Sumant Mandal.

I had drawn a large circle on the whiteboard – representing our business of g2w. Within the circle I started carving out areas (think pie charts) that defined the business lines of the Company. The carve outs showed online games, portals, social games and virtual worlds. It quickly looked quite crowded. Yet I had a marker in my hand to fill in new sections representing our forthcoming iStore games and Android games.

As my marker approached the circle once again, I was nervous. This was the classic ‘doing too many things’ syndrome.

My marker touched the white board and just as another line began to appear, Jim Armstrong, hollered at me in a rather stern voice and said, “Alok – don’t tell me you have more offerings to explain to us?” I calmly said, “Yes Jim, we have these new lines rolling out as we speak and…”

Before I could complete my sentence, Jim suddenly sat upright on his chair, broke into a big smile and exclaimed loudly – ‘That’s audacious Alok – and we love you for your audacity!!”

The lesson I learnt in that SATORI moment was to be audacious.

Audacity perfectly captures the concept of VENTURE CAPITAL. It represents the transaction of money that is controlled by the really smart and experienced investors, who give it to buccaneers like me to do anything to find gold and treasures. In this case, my lead VC was telling me – Alok – go out there, be bold and ambitious and kick butt (and not start another mail service)!



I hope I added some value to you, via these examples.

To summarize, these are the 11 incredible lessons I learnt from 10 incredible VCs:

1. Cultivate infinite entrepreneur stamina – Abhay Havaldar

2. Try and understand your own DNA – Rajesh Jog

3. Think horizontal, diagonal and vertical – Neeraj Bhargava

4. Stumble, fall, survive and live – Renuka Ramnath

5. Become comfortable with yourself – Sumir Chadha

6. Put family first – Vab Goel

7. Never dilute your own efforts – Nandini Satam

8. Measure what matters and ask ‘why’ – Sumant Mandal

9. Cultivate your own Personal Brand – Sumant Mandal

10. Never say never – Karthik Reddy

11. Be audacious – Jim Armstrong

Thank you VCs for these invaluable lessons. At the outset, I will admit that I am not your “Poster Boy” cover success story and instead may have pained you, but sometimes your own rewards may manifest themselves in many other ways than you may have imagined.

In my case, I hope via these stories and many more, I will inspire young entrepreneurs to actively seek you out as well as other VCs, appreciate the good that VCs do, respect and admire them and go on to create Companies that the world salutes.

Pardon me for any mistakes, errors and omissions.

Photographs are from various sources. I hope the content owners pardon me for using them.

Entrepreneurs, please go out there and make us all proud!



First Published on: Oct 30, 2012


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  1. Entrepreneur is the King of the Castle, and Kings never run away…. Wah !!! Maza aa gaya … 

  2. I guess its a whole big lesson for all the Start Ups who are preparing their pitch out their. Guys/Gals make a checklist and prepare your positions for each of the learning in this post. Excellent post Alok though we have read some of these lessons before in few blog posts of yours earlier but composing all of this in one post gives it a unique value especially for someone like me who is keen to know what one needs to prepare to pitch. 

  3. The Following has been Copied-Pasted=Printed and Pinned.

    1. Cultivate infinite entrepreneur stamina – Abhay Havaldar

    2. Try and understand your own DNA – Rajesh Jog

    3. Think horizontal, diagonal and vertical – Neeraj Bhargava

    4. Stumble, fall, survive and live – Renuka Ramnath

    5. Become comfortable with yourself – Sumir Chadha

    6. Put family first – Vab Goel

    7. Never dilute your own efforts – Nandini Satam

    8. Measure what matters and ask ‘why’ – Sumant Mandal

    9. Cultivate your own Personal Brand – Sumant Mandal

    10. Never say never – Karthik Reddy

    11. Be audacious – Jim Armstrong

    Alok Sir….Can NEVER thank you ENOUGH for these Lessons.
    Need to point out “”Cultivate your own Personal Brand from Sumant Mandal Sir” is the best and thousands of us have gained from this Advice. Thanks to you for Following THIS!!


  4. How did you managed to get all these appointments…..I think thats the key thing for me to know.

  5. Maza aa gaya indeed! Awesome awesome post…loved it…

  6. Loved every bit… We don’t have VCs for us, but definitely Alok ji on our side. Thanks for sharing such wonderful lessons!

  7. Great and very helpful post. These 11 points are more than tips to young entrepreneurs like us … Thanx for sharing 🙂

  8. Manav, I think its got to do with Lesson 11 – Be Audacious!

  9. Reading this was one of the most well spent minutes of my life… thanks a lot…:)

  10. I am glad to be a part of this community!!!

  11. Amazing post Alok.. becoming member of Rodinhood is the one of the best part happened recently as I have started my Entrepreneurship Journey !! 

  12. Great Post Alok..Liked it…

  13. i had read this piece probably 10 months back or so and it made some sense ! today i am reading this again and i find a whole new level of meaning in it ! guess this is what masterpieces are like , which instigate new thoughts to the evolving minds !

  14. Thank you so much for the valuable lesson you have shared with us Alok. Truly incredible.

  15. Hi Alok ,
    Nice Post Thanks For Share

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