Henrik Werdelin will be speaking live at Percolate’s first industry conference: Transition. Come to the Times Center on July 16th to join a conversation about how technology is reshaping marketing, the enterprise and the world. Learn more.

Hernik Werdelin is one of the most prolific people in technology. Part of the founding team at the video streaming company Joost, he’s been an EIR at Index Ventures and runs Prehype, a startup-incubator-as-a-service company for big enterprise. He is also the founder of Basno, a digital badging company, and Barkbox, a subscription service for dog owners — the latter has well over 100,000 subscribers and is on track to do $100M in sales in 2014.

He dropped by the Percolate offices last week to share some of his lessons building great products and creating beloved brands. Below are some excerpts and ideas from that conversation.

Take a big view of your mission

BarkBox’s main business is a monthly shipment of toys, bones, treats, hygiene products, and innovative new gadgets. But the product line has extended to content: BarkPost gets 5M unique visitors per month, to veterinarian services: BarkCare connects dog owners with vets for $199/mo, to rescuing shelter dogs: BarkBuddy is a “Tinder for Dogs” mobile app featuring photos of dogs that need a home which has garned 5M swipes since launching earlier this year.

These product extensions make sense because the team has always thought broadly about their mission. Henrik says when they evaluate new options, they focus on three things:

1) Will this help make dogs happy and healthy

2) Will this help us stay financially independent?

3) Will we be able do this in a unique way?

To get a hit, you have to try a lot of things

“Momentum is the driver of most things. It’s hard to predict the success of things. You can help prevent it from being a failure but at some point, you just have to cross your fingers. The answer then is high quality output. Lots of it.” — Henrik

Optimize for a 60 year career

“One realization I’ve had is that life is long. People have optimized their careers on an incorrect timeline – trying to hit a senior position at 50, coast till 60, then retire. With the way things are going, we’ll probably live to 100, which means we may be working until we are 80. And so I try to take better care of myself given that I’m only a third the way through my career.” — Henrik

Don’t ignore trends you find silly

Have you heard of Menswear Dog? A couple in Brooklyn has turned their dog into a minor celebrity, with over 97k followers on Instagram, by dressing the four year-old Shiba Inu in mens clothing. While some might laugh it off as just another goofy Internet meme, Henrik sees an opportunity to jump on the celebrity dog movement.

He envisions creating an agency to represent these celebrity dogs (yes, there are others) and showed us a preview of an photography app Barkbox has developed to help turn your dog into a celebrity. What’s the unique twist? They’ve solved the toughest part of photographing a dog: getting it to look at the camera.

Dog owners know that it’s basically impossible to get your dog to look at the camera. So the app has a preloaded set of sounds, from a squeaky toy noise to a quack that go off right before you hit the snap button, catching your dog’s attention and helping you get the perfect shot.

The new model for internet companies

“What other ‘box companies’ that do subscription shipments are facing are a lack of momentum. And that’s because of the structure of the company. Building internet businesses used to be like crafting a pop band: there was a formula. Build the right team, have a catchy chorus and hook, etc. Now it’s more like doing a jazz band. The leader gets cool people together, they have a bit of a theme. A rhythm. Then you start to jam and see where it takes you.” — Henrik

The Burden of Entrepreneurship

“An innovator’s first role is to lie to everyone and get away with it. Investors. Employees. Spouse. Yourself. We take the anxiety away from everyone around us so that they can do great work and you hold it inside yourself. If you are a sensible person you don’t do a startup.” — Henrik

Heavy Hitters vs Insecure Overachiever

“Over the many positions I’ve worked , I have hired hundreds of people. What I’ve realized is that it’s not about their CV. I am looking for people who are self starters — people who identify solutions and add value just by being here. One question I like to ask is – ‘Tell me your life story starting at when you were 6 years old.’ People aren’t prepared for this question so their answers end up being more authentic and revealing.

There’s a “heavy hitter vs insecure overachiever” debate that I often have with my business partners and in general, I believe in hiring people who are slightly under qualified and giving them a big job.” — Henrik

Setting the course

Henrik mentioned research has shown that there’s a critical window for a child’s brain and body development that’s set in the first 1000 days. He believes similarly a company’s DNA and trajectory are set in the first 1000 days. Much of what determines a company’s success or failure are shaped at the beginning.

On creating a brand

“When the Brits invaded Germany, they convinced the Germans they were going to hit Pas de Calais instead of Normandy . They didn’t call up Germany and tell them this, but they took actions that allowed Germany to infer it, which made it that much stronger. Because they thought they had figured it out and so they were much more convinced.

Branding is the same thing. I ask myself two questions:

1) What do we want people to say about our brand?

2) How can we create signals to make people think or realize these ideas?” — Henrik



Subscribe for more smart thinking on content and audience.