An anecdotal encounter with a Product Visionary CEO

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W-SF-logoDuring my trip to San Francisco for Google I/O 2013, I have an unexpected encounter with a CEO of an notable Internet company in the lobby of a hotel where I stayed. The date is 15 May 2013 (first day of Google I/O), and he was meeting with someone (a lady who I suspected to be a journalist) between 4-7 pm in the bar area. I have told this story only to my wife in the same evening and concluded that I won’t talk about this encounter after something major was happening for this CEO and his company at that instant of time.

It’s one of those days I bumped into someone unexpected.

Let me reveal who he is by the end after I tell you the whole story here. Around 4.30 pm, I came back from the Moscone Centre to W Hotel San Francisco to put my new Chrome Pixel back in the hotel room. After dropping the Chrome Pixel, I stopped by the bar to pick up a pint of beer at the counter. When I got seated, I saw this guy dressed with a hoodie with jeans talking to someone. Immediately, I recognized who he was, based on a video from fireside chat he did with his investor in TechCrunch Disrupt. However, I thought that it might not be a good idea to speak to him. So, I walked back to the Moscone Centre to catch up with a couple of friends who were attending the Google I/O.

You may think that it’s the end of the story. Two hours later, I walked back to the hotel and this time, it was to drop my computer bag. I saw the same CEO who was in the same location again, alone this time but he was busy looking at his smartphone. Since I have been actively using his company’s product and really liked it, I decided that I should go and speak to him. After all, what’s there to lose? The worst is that I got it wrong or get shunned away.

I plucked up my courage, walked up to him and asked if he was the person and I told him that I saw him on a video in TechCrunch Disrupt from Singapore.

My first words were,

“Hello <his first name>, my name is Bernard and I am from Singapore. I have been using <your company name> for a while. I thought that it will be great to have the opportunity to tell you that I have enjoyed using the product.” I said and probably paraphrased some of the words, and I usually don’t converse very well with famous people. I was ready to walk away after this one minute introduction.

He caught me by surprise as he turned out to be a gracious and polite guy. I have read stories about him from his former co-workers. He told me that he was happy to hear that I am a customer of his product, and started asking me what I thought about the product itself. What happened in the next fifteen meetings, was a learning for me that I will never forget. I realized that I was miles away to where I want to be.

What ensued was that we discussed about various features of the product, for example, the discovery feature and how he was happy about the communities that are built from his product. I also conveyed that I liked the fact that I can make purchases seamlessly and build my page better. He drilled deep down to some of my nuances about his company’s product and asked me how I have been using the product, from photo uploads and the mobile experience (whether I was using the company’s mobile app or using a third party app to do so).

It was happening really fast and throughout the conversation, I never felt that he was patronising me but there is a genuine eagerness to learn about my experience as a user. We ended the conversation fifteen minutes later. I did not ask him for a name card nor a contact. I don’t think that we will ever meet again and he probably did not know that I write about technology trends in Southeast Asia.

This fifteen minutes conversation have taught me about how to engage users and carefully tease out feedback from them. It’s something that I am still learning while building products out here in Southeast Asia. He did provide some thoughts on why certain features on the product are built centred on how the user would use the product.

What I learned from him through this conversation is priceless, as I explained to my wife an hour later on the same day, is that how he engaged his customers and his empathy and willingness to spend the time and speak to me. I also commented that the rumors circulating about his company being acquired by an Internet giant were probably true. I told my wife that I will talk about this encounter when things have died down. Very few CEOs I have met have ever done that. It is a good lesson that I learned and will bear that in mind for the future.


A few days later, his company was acquired by Yahoo! for US$1.1B and the CEO I have spoken to @ W Hotel, San Francisco is David Karp, the former CEO of Tumblr.


You can also read these articles from his former CTO, Marco Arment and his investor, Fred Wilson’s thoughts about him as a product visionary, and I can concur that it’s true after this encounter with him.

Originally published in Tumblr and then Medium. :)