Oliver Roup - Founder and CEO of VigLink

[quote style=”boxed”]I just did a formal exercise to try to map this out. There is a 90-minute focused block in the morning to get a big task done and there are two 60-minute email blocks. Outside of those two time slots, I try not to do email. I also have another 90-minute block set aside for one-on-one meetings with my team. I meet with each team member once a week, alternating between a 30-minute and 60-minute check-in. The reality of the day is messier, but as the company grows, implementing a framework for how I spend my time has been critical.[/quote]

Oliver Roup brings more than 15 years of software experience to VigLink. Previously, he was a director at Microsoft, in charge of products for various media properties including XBOX Live Video Marketplace, Zune Marketplace and MSN Entertainment. Oliver was also an early employee at Internet Radio pioneer Echo Networks and has worked for Paul Allen at Vulcan, for iPlayer at the BBC and for the Founders Fund. Oliver has patents issued and pending; covering micro-transactions, media and metadata. He received his bachelor’s and master’s degrees in computer science from MIT and his MBA from the Harvard Business School.

What are you working on right now?

VigLink, a content monetization solution that pays online publishers when readers click on a link within their content to buy or learn more about a product or service.

Where did the idea for VigLink come from?

The company started when I wrote a crawler to count links to Amazon on the web and found that less than 50% were enrolled in the affiliate program (meaning the publisher would be compensated if a purchase resulted from the click). It was an indicator that there was room for improvement in the space. Publishers either weren’t aware that affiliate programs existed or found them too time consuming and difficult to use. Both problems were interesting and worth solving.

What does your typical day look like?

I just did a formal exercise to try to map this out. There is a 90-minute focused block in the morning to get a big task done and there are two 60-minute email blocks. Outside of those two time slots, I try not to do email. I also have another 90-minute block set aside for one-on-one meetings with my team. I meet with each team member once a week, alternating between a 30-minute and 60-minute check-in. The reality of the day is messier, but as the company grows, implementing a framework for how I spend my time has been critical.

How do you bring ideas to life?

The key task of the entrepreneur is to pitch, which is just a fancy way of saying “to sell.” First you pitch co-founders, then customers, then investors, then employees, then lots more customers then partners and one day, from what I hear, acquirers. Actually VigLink started by pitching investors, which is not recommended but somehow worked out for us. It is much better to have a team and customers first.

You have to become great at telling your company’s story. The process, at least for me, has been critical in helping to mature the company. You notice what works well, what doesn’t and you refine.

What’s one trend that really excites you?

A number of startups I admire are improving the utilization of resources that otherwise are under-utilized. AirBnB, Uber and ZeroCater are all good examples of companies promoting better utilization of existing resources. I think there is a great deal of opportunity there. VigLink is pursuing a similar strategy by monetizing the ordinary hyperlink, which until now has been largely ignored.

What was the worst job you ever had and what did you learn from it?

I spent about 4 months in 1999 at a developers-for-hire consulting company. It had a ton of hype but I knew about 10 minutes in that it was the wrong job for me.

If you were to start again, what would you do differently?

I’d start with a co-founder. Being a sole founder is a mistake and you basically can’t get a co-founder later. It’s easy to underestimate the mental burden of being on your own. It’s not so much that you can’t make decisions, but that sometimes you don’t even realize the decisions you aren’t making. The right co-founder provides another perspective and another set of hands to get things done early on.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I’ve already mentioned this, but without a doubt, it is pitching. Sometimes I feel like I spend my whole day talking about VigLink to customers, prospective employees, investors and partners. It’s critical that an entrepreneur become great at telling their company’s story. Nobody can sell the company like the CEO.

What is one business idea that you’re willing to give away to our readers?

VigLink is reinventing the publisher side of affiliate marketing. I think a huge opportunity exists on the merchant side. Small merchants are dramatically underserved by the existing providers.

What are your three favorite online tools and what do you love about them?

  • Rapportive: I can quickly learn more about the people I’m interacting with over email and easily connect with them on social networks.
  • Asana: It’s simple shared to-do list management that lets me track my own work, as well as others.
  • CloudFlare: It’s a free (or low cost) service that makes your website safer and faster.

What is the one book that you recommend our community should read and why?

Founders at Work by Jessica Livingston. It provides real insight into the less “Hollywood version” of startup foundership.

If you weren’t working on VigLink, what would you be doing?

I’d go work for SpaceX. I grew up dreaming of spaceflight and Elon Musk is making it happen. People will be walking on Mars in the next 10 years and I’d love to be a part of that.

Three people we should follow on Twitter and why?

  • @JonathanMendez: Founder of YieldBot, a fellow disciple of the value of the click and someone who always has insightful things to say.
  • @Nivi: Author of Venture Hacks and Founder of AngelList. He reads everything and he’s great at extracting the most insightful 140 characters out of almost anything.
  • @NielRobertson: Founder of Trada and my CEO mentor. He really shows how it’s done operationally.

Who is your hero?

Lately I’m a big fan of Christopher Nolan. Everything he touches is brilliant and original.

Any advice to the aspiring founders out there?

Don’t forget to have fun. It’s a marathon not a sprint; if you are clenched the whole time you aren’t going to make it.

Connect:

Oliver Roup on Twitter

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