Startup Founder Kevin Rose

Kevin Rose

Generally speaking, Kevin Rose would consider himself a technologist. Since he has been working in technology for all his life. He moved out to the Valley in 2000, when dropped out of college and came to the Bay Area to start working at a couple of startups. In 2004 he launched Digg, and in 2006 he started doing some angel investing. He also launched a couple of other startups, sold a few, and a few have failed. Overall, Rose likes to build things, and as he said during our meeting “I probably should start over and say I’m just a builder”.

This passion for building also evoked an entrepreneurial mindset. He reminisces, “I couldn’t afford the Nike Air shoes that would show the ‘air’ on the side. It said Nike Air but I wondered ‘why don’t they just show the air pocket’. So I cut open one of my shoes with a hacksaw to make sure it had the air inside it, and it did. My dad wasn’t happy with that, but I told him it was because I wanted to install springs in it so I could slam dunk like Michael Jordan. So I put springs into my shoes, and then tried to hot glue it back together. But all that glue fell out, it didn’t really stick that well. But that was when I started experimenting with stuff.” Another anecdote Rose shares is how he learned to type via a racing car game that he was playing. And then he started to do some basic programming and editing games.

We met Rose, in his role as venture partner at True Ventures and founder of his soon-to-launch meditation app Oak, at the Next Web 2017.

What inspired you to become an entrepreneur?
My parents would try things; my mom had a couple of different businesses that she would do. And my dad had a couple of different businesses that he created. They were very small kind of like family run businesses, but just seeing that you could do that sounded so cool to me. Also, I like the idea that you don’t have to go work for someone. You can just think of something and go do it. So, why wouldn’t I just go create a business and try my own ideas? To me, that that was the better path. Especially once I’d had a couple of jobs. I was like ‘why am I working for someone else if I could just go build what I want to build?’. So I think that that helped out a lot, but also I learned to understand failure.

Failure means that you tried the hardest thing, which is amazing. The best things are often the hardest to do emotionally, and as a person. Whether that means working on your marriage rather than getting a divorce or admitting you’re not good at something and taking additional schooling years after you get to finish school: these hard things are the best. You’re at your strongest when you’re trying these hard things. So I think that failure means that you tried something really difficult. It’s actually a really cool thing because not many people do that. Most people are just happy to go and work for someone else and take the very easy path.

I meet so many founders in this line of work, especially in the investment side. And if you see a young founder and they talk about something that didn’t work out it’s often met with like a kind of odd glance at the ground like ‘oh you know’ like they’re ashamed of it. And I’ll be like, ‘that’s awesome, life’s a learning’.

Can you remember what the biggest barriers to entry entrepreneurship were for you?
A lot of barriers that I hear about from people is that they are working a full time job already, have kids, and therefore can’t break away and find time to do something like that.

People will often cite time as being an issue. And I think that it’s really [dependent] on how you frame what time is and what it means to you and how you use your time. I also still continue to build stuff on the side. And the reason I’m able to do that is because I don’t watch television. We forget that we can take back an extra four hours every night if we just don’t watch television. Every decision in life is just a series of tradeoffs.

When you say yes to something, you’re also saying no to something else. I tend to say no to things that aren’t helping me achieve my goals when I have something I want to build. One way to start is to write down all the things you do throughout the day, throughout the week. If you’re telling yourself you have no time, take this weeklong log of life and then you’ll quickly see trends emerge about things that are really not so important. Those you can cut out to go and build.

A second thing is that people say ‘I don’t have any money to do it’ and ‘I don’t know how to raise venture capital’. The good news is, that it is so inexpensive to launch, especially software. Everybody can learn how to code and to host and launch a project these days. There are tools out there that can help you setting up things. So the cost thing is kind of taken out of the equation. I once met a very creative founder that couldn’t afford and didn’t want to raise venture funding and so. He worked out a deal with a co-founder that they just did an equity split and he didn’t have to pay the engineer. There’s ways to even do it with very very few dollars.

So, I think that if someone says they’re having a barrier, it’s typically a mental one. It’s not really a physical one. Make a checks and balance of your everyday life and see where you can miss out on something, and things you should invest in. The investment doesn’t have to be in building your startup right away. It has to be in the education required to understand the sector that you want to build in. Understand a wide variety of different topics at a high level but enough to where you won’t be fooled or make the wrong decisions.

What does success look like to you personally?
I consider something a success when it’s launched. The day that it’s launched: that is a very concrete point. That’s the only successful day, because what you build with your vision is now public and out in the world. That’s as good as it gets, because you took your idea and that either works for a thousand people or a hundred people, or 10 million people or whatever it may be. You can hope and say ‘I hope my idea resonates with a large group of people’, and if it does that’s like icing on the cake. If it eventually becomes a wild success in terms of usage, that’s something different.

Success is getting the idea out there because you actually did it. You got that thing that you’ve been working so hard away on, for so many months, that is now a reality and I think that that’s success right there. Part of the joy of launching something is daring to put it out there, and that’s a difficult thing to many people. A lot of people have a hard time getting wrapped up in their head about what other people think of their idea. But you have to understand that you can never read other people’s minds. You can get your idea in front of people in early stages, so they can gauge what’s working and what’s not to help you refine the product. But ultimately… You shouldn’t worry about launching it. As long as you put all of your effort into: Understanding everything you could possibly understand and refine things to the point where you’re ready for a version 1.0 then you’re good to get it out there. You should take pride in that’s the best you could possibly do. Because that’s really what we should be proud of: the fact that your idea was created.

“What’s funny is that I would not go back and tell my younger self anything, because I think that I wouldn’t be where I am today if I hadn’t made those mistakes.”

What does a productive day for you look like?
A productive day is one that combines a good amount of effort and a healthy amount of distraction. My most productive time is during my first cup of coffee. So I tend to focus a lot of the heavy lifting in the very first part of the day. Then I try to get some physical activity to kind of break up the day. And then I use the last part of the day for reflection and also setting up for the next day. And there can be some work in there as well.

But I’d rather do a better-focused effort, where I’m not letting my brain become fragmented and distracted. Startups often say you have in a limited amount of time to work in each day, meaning that it’s just like their time and work is never ending. The problem with that is that it’s easy to check a website for few minutes, or some tweets from a friend, or a funny YouTube video. That’s easy to do when there’s no set hours. But if you set a structure, you say ‘I only have this many hours to actually work and I can do that stuff later and that’s fine because it’s part of my structure — but right now I’m in work mode and I find that I can get a lot more done that way’. [13.6]

Work-life balance is so important. You’re not going to find true happiness in your work. I mean, that’s just a part of life. And if you neglect your relationships or friendships… There are these studies based on centenarians, like the people who live over 100 years old, the common kind of backbone and fabric is the amount of social connections that they have. Real deep intimate social connections with other human beings. That rings true for me like that. That certainly gives you gives you an outlet to talk about you know what’s going on in your life, and your emotional health. It can’t just be all about work all the time. Balance is key.

Which one thing would you love to tell your younger self?
What’s funny is that I would not go back and tell my younger self anything, because I think that I wouldn’t be where I am today if I hadn’t made those mistakes. If a starting entrepreneur had a question about what’s the one thing they should do right, I would say that one thing — that a lot of entrepreneurs overlook — is the hiring process.

Some people seem to think of it as a chore, they don’t put enough time and effort into really fully vetting candidates and making sure that they fit the culture, have the right skill sets, or have the kind of depth of knowledge that the company needs. Then they hire the wrong person. I think that you have to really spend a lot of time and effort on that hiring process. Google is notorious for having a very challenging process: Our hiring process was very lengthy and cumbersome and it took a lot of time. But the good news is that if you got through and you got hired you were given the keys to the castle from day one. So you could make big sweeping decisions that would impact tens of millions of people on your first day. People were trusted. And I think that’s one of the keys to their success. The hiring process is certainly something I don’t think enough entrepreneurs put effort into.

Is that also what would you highly recommend aspiring entrepreneurs to do?
Absolutely. Also, I would I’d recommend they read ‘Work rules!’, done by Laszlo Bock who was the head of H.R. at Google for many many years. He’s the one that helped create a lot of these different processes, did a lot of the science behind it to validate it. Part of the hiring process has to include a culture piece, so that you know that one day you will get these new employees in on what you’re trying to achieve. And so I tend to include that as a big chunk of the overall process when talking to candidates.

What has been your biggest failure?
I’m failing at a lot of things. The better way to put it, is that it’s something I’m currently learning. Because I really don’t think of it as failing. I think of it as something that I still need to learn. I would say that this there’s a whole slew of different things.

One of the things that I’m trying to wrap my head around these days is going even deeper on understanding all of the data; how to make sense of data. I think understanding how to really use data to impact and change products is something that we did a lot of Google, and it certainly is kind of this evolving industry. So I’m trying to get better at figuring out how to properly instrument applications so that I can get at the right data to understand these problems. So I’m building a meditation app right now. And one of the things that I want to do is eventually use some of this machine learning to help build dynamic meditations based on some of that data. And this is a world that I just don’t really understand. So right now all I’m doing is making these revisions based on what I do understand, which is how to go out and collect survey data, how to use the emergent trends out of that sort of data, to make tweaks to our scripts and things like that. Eventually, once we get to enough users in scale, I’d like to do that in a more automated fashion. So that’s something I’m still trying to learn.

Another interesting thing is, that when you start [a startup] these days I don’t think you necessarily need to raise venture capital. And so, I’m trying to figure out kind of what impact that has on traditional VCs. Also, there’s this trend around ICO’s, initial coin offerings, that are people using spun up versions of cryptocurrency as a way to crowdfund their kind of platforms. So trying to figure out what ways and how that might impact venture capital, and how that can also be used to fund and fuel projects is interesting. Right now, I self-fund on my little side projects, but I’ve been fortunate enough to be able to do that based on smooth angel investments and stuff that I’ve done. But it’s certainly something to pay attention to.

I think one of the things I’m still trying to work on, as I tend to avoid conflict a lot, is trying to get better at that in a very peaceful way. It’s something I’m failing at. I think that the issue is when you have the right people in place, everything works perfectly. You don’t need to micromanage people. What’s difficult for me is when you don’t have the right person in place. How do you address that and confront that and manage through that? It’s certainly something I think that is unique to every individual because everyone is different. And to be able to sit down and have those tough conversations and to coach people through things like that is still like a challenge.

“What I didn’t realize is that I wouldn’t have realized those were even issues unless I had failed. That was how I grew as an individual.”

So, what has then been your biggest learning?
I would say it’s been in the way that I reframe that thinking from failure to learning. After Digg failed, I was really upset about that whole process and thinking about what I should have done differently, or if I could go back in time I would’ve done X, Y and Z, and we should have implemented this feature, we should not hire that person and … What I didn’t realize is that I wouldn’t have realized those were even issues unless I had failed. That was how I grew as an individual. Later I realized that it was not really a failure.

Once I heard that being described as being thrown into the ocean. You’re tying to grab on to stuff and try to swim, and you’re trying your hardest to, but you go in ten different directions. The reality is that you shouldn’t be trying to do that at all and you should really just stop. Look around, and take a deep breath, and maybe you tend to like it. All these products that we build, everything that we do, they’re all waves and cycles. Almost every startup we talked about here, in 10 years that will be gone. Almost every single one. Only a couple will still be around. Once you understand that, you start trying to grasp these things and you don’t look at it as something you need to hold on to.

When you can float then you can relax and do your most creative work. I feel that creativity comes from being relaxed. Not when you’re freaking out about your company failing. And so that’s been my greatest learning: how to reframe all this so that I can look at the launch as my most exciting moment, and that’s the pinnacle for me. It’s not getting millions of users that are going to come and go, because that’s out of my control.

How long did it take you to reach that state?
Since 2004 till about a year ago. Really. I mean you just have to. You get a little bit older and become comfortable in your own skin to where you are. You don’t take it personally anymore. You cannot direct the future.

What makes you worry?
I don’t like turbulence and flights. I’m not a big fan of that. That’s definitely one thing. When you start to feel the turbulence on flights. I worry a lot about my investments. Like Uber. It’s one of the deals we did at Google Ventures, ninety nine percent of my net worth is tied up to it. So I worry about that. I hate to see such a great idea lose its way. I hope that there’s some compassion that comes to that company for the drivers and for the people using the service.

I mean there’s a lot of little things that they’re not really tied to tech though. You know like standard stuff like health and family, and there’s a really bad homeless problem in San Francisco that nobody can figure out. It’s really tough. Some people say that there’s too many social services, which is attracting more homeless people from other cities. But there’s all these different points of view and no one can figure it out. And there’s limited space here, so it’s not like you can just go and build these massive shelters. That’s one of the things that we’ve got to figure out.

Mental health is also a huge one. So I’m excited about that and that I have see more entrepreneurs like Dave Morin, and some other folks, that are tackling mental health. I think that that’s going to be a huge push of them and also opening up about mental health. It’s had such a bad stigma associated with it, but in reality we know that entrepreneurs are probably some of the people that need the most mental health. Because they are very creative people. And I would say generally in creative fields we see a lot of mental health issues. I don’t know why, but it seems that creative people have, whether it be comedians or musicians, tendencies for depression and just mental issues in general.

Who is your favourite super hero?
Philip Rosedale, he created Second Life. What I like about him, his ideas are just so crazy, they’re just nuts, but fun to listen to. You’re like ‘wow, what if that would work” and every idea that comes out of his mouth is brilliant. He spits out so much creativity. In term of creative mind, I really like his mind. I get the most enjoyment of like big bold ideas that nobody has thought of and that are just like the ‘what if’ scenario’s. My brain has a lot of fun with those ideas.

What’s your favourite emoji?
It has to be the thinking guy… 🤔

Challenges expressed are in no way meant to solicit commercial acquisition.

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