When was the last time he pulled a sickie? How far does he ride his bike each week? And why he gets out of bed in the morning? (Oh, and also the secret to business success, what he looks for in a start-up and which industries are set to boom). 

Idealog: You’ve seen the internet grow from its infancy to maturity. What has surprised you most about the way things have turned out? 

Wenokur: That’s an interesting question. Obviously mobile. You always knew it would happen, but the extent to which it’s happened is shocking. I don’t need a computer anymore; I can do pretty much everything I could do back in 1998 on my phone – and I can probably do it better. That’s pretty amazing, because if you look at the form factor back then, I didn’t think that would happen. That’s amazing to me. 

The other thing is how quickly it’s been adopted over the world and how it’s changed the way people do things. You look at things like Amazon which was, back in ’98, a bookseller. People were like ‘Oh my god, they’re going to put Barnes & Noble out of business’, but nobody thought they were going to put Walmart out of business. Most people around the world will start shopping online before they will start shopping in other places, so that’s also a big surprise to me. 

And I would say, additionally, the fact that Google has gotten into so many other things is surprising. When the charter of the company was to make all the world’s information easily accessible, you can see YouTube and Gmail – those things make sense – but the fact that they’ve now moved into self-driving cars and robotics [although Alphabet has just put Boston Dynamics up for sale] and artificial intelligence is also a little bit surprising. 

So it’s the sheer pervasiveness of digital’s influence that’s the most surprising to you?

Yeah, a little bit. It’s amazing to me that a company I went to go work for in 2000 – and that I’d known from when they were founded in 1998 – suddenly became the most valuable company in the world, for a brief period of time. I knew everybody would use it for search, that wasn’t a question, but the fact that it does so much is really amazing to me. 

And you think about Apple, if you go back to 1998 and the dawn of the internet, that company was almost bankrupt. 

But now, their success seems almost self-evident, right? 

Yeah, and think about how little we speak of Microsoft now. You go back to the early days and Microsoft was it. They were trying to put Netscape out of business, trying to make AOL irrelevant, trying to put Google out of business, and now people don’t even think about them. That’s a big change in a pretty short amount of time. 

So you’re known as a ‘business guy’. Would you consider your business achievements as your greatest achievements?

No, I don’t think my greatest achievement is in business. I would like to think that my greatest achievement would be something that I did for the community. Business is something that is interesting to me, but it’s also a means to an end. You would hope that if I’m lucky and successful and make money then I can use that money to do something good for the community. That’s what I would hope would be my greatest achievement. 

If I could take credit for my kids then that would definitely be my greatest achievement. 

So you can’t take credit for your kids? 

My wife would probably be better off taking credit for them. 

That’s a good answer. And a prudent one too. Looking back on your career, was there a definite moment when you thought, wow, I’ve made it? 

No. Because in Silicon Valley there’s always someone who’s doing something bigger and better than you are, so I don’t think that thought crosses your mind. You really never know.

I joined Google in 2000, the dotcom era blew up in 2001 and you really never knew that it was going to take off to the extent that it did. You never really know what’s going to happen when you start one of these things. Even now, when we invest in companies – I’m a partner in a venture capital fund in India – you think you’ve done your due diligence and you think it could be really successful, but it’s not until you actually see money back in the bank that you know it’s working. There’s really just too many things to worry about that could go wrong. 

So if there’s all this tension around everything that could go wrong, where is the release? Where is the moment you can say ‘well that’s a job well done, now I can relax’?

Me personally?

Yes. 

Me personally, I probably should celebrate successes more than I do. 

And what’s the price of that success? Have you done things that others wouldn’t do? What’s the difference between you and the also-rans?

For a lot of it, you can’t really point to anything other than luck ­– being in the right place at the right time. I know that’s a bad answer, but there’s definitely an element of luck that plays a part in this. There are a lot of really smart, hardworking people that never ‘made it’, never get their big win in Silicon Valley, never get that big promotion, never get recognised and toil away, and I think for a lot of it you have to point at being in the right place at the right time. 

And we can’t talk about success without talking about failures. Have you had grand designs that were close to your heart, you worked on them but just couldn’t bring them to fruition?

I’ve worked on projects that have failed. I haven’t founded anything that was a failure – not that that’s a bad thing to do – but I’ve worked on a lot of projects that haven’t succeeded. You obviously learn something new from each one and hopefully you can use what you learned from that failure with the next thing. But there hasn’t been any huge failures.

Either that or I’ve blocked them out. 

Do you actually block them out? Or do you have regrets about things that didn’t go as planned?

Oh, there’s no question I have regrets. I think people lie when they say they don’t have any regrets. It’s a learning experience, sure, but there’s a lot of things I look back at and go, ‘Man, I really wish I had have invested in that’ or ‘I should have got into that deal’. I can’t imagine people don’t sit there kicking themselves over opportunities they missed. 

I don’t sit and dwell on it, though – ‘Oh, I should have invested in Uber’. I have my own investments right now so I sit and go ‘Thank god I invested in that one’. 

When it comes to investing in start-ups, what’s the one thing that’s non-negotiable for you? What are you willing to walk away over?

You know, it’s a cliché, but really the most important thing is the team, because at the end of the day that’s what you’re investing in. The idea may change and the company may pivot, so it’s really a question of ‘can the team handle adversity and figure out a way to make this successful?’ Even though you’ve got to look at other things, it really comes down to the people. 

So what drives you? Why bother? Why not stay in bed? 

Why not stay in bed? Well it’s fun to invest in companies, to help them grow, to watch them succeed. It’s a lot of fun. It’s a hard thing to do, but it’s so much fun when they’re actually successful, especially when they do something different. When they change people’s behaviour or the way business is done in that industry, that’s great. That’s why I do it. And as much as I love to ski and ride my bike, you can only do it for so many hours a day. 

What’s the one thing you’ve always wanted to own, but don’t?

I would really like to have a bicycle made by Dario Pegoretti who is a custom bicycle frame builder. 

How many hours do you spend on the bike per week?

Seven or eight hours. 

And what’s the furthest you’ve biked in a single day?

125 miles. And it wasn’t so much the distance, it was that it  involved about 16,000 feet of climbing. It was a bicycle trip across the Pyrenees over six days. 

Sounds dreadful.

It was okay. 

Alright, time for some hot tips. What’s about to blow up? Where should I put my hundred bucks?

Globally you’re going to start seeing a lot more in education. I think part of globalisation is that people need better education, especially in the US. I do a lot of stuff in India, and people there need more access to education and better training. I think education start-ups are going to start getting really interesting. Healthcare start-ups are starting to explode here – we’re looking at a lot of stuff in Asia for that. Those kinds of things are interesting. In the US we’re starting to see insurance start-ups, offering different types of insurance using technology. Those are the broad themes right now, and obviously the internet of things. 

So you’re actively investing in these things – edutech and e-health – right now?

We have an education start-up in India that we’ve invested in, which helps with online test prep. In India, when you graduate from high school and you want to go to engineering school, you have to take the entrance exam. There’s a million kids a year that take it and basically that determines their life, so we’ve invested in this company to help kids train for that exam. It gives them access to information and instruction on how to study better and we think that’s going to change the way kids prep for all exams in India.

On the healthcare side we’re still looking but we haven’t found anything. 

Last question, but still on the subject o health: Have you ever called in sick when you weren’t really sick? Be honest. 

Um…

Be honest. 

Yes. But it was a long time ago. 

I’ll be sure to include that it was a long time ago.  

Okay, but you don’t have to. I don’t have to call in sick anymore.