Will Bunker

By Catherine Lowell
Originally published on EquidateInc.com

“When I told people what I was working on, they would physically flinch. You’d see people back up from the conversation. Even I had a hard time believing it.”

Meet Will Bunker, a prolific investor and maverick entrepreneur. In the 90s, he started the dating site that became Match.com. Now a Founding Partner at GrowthX and co-founder at GrowthX Academy, Will’s mission is to identify companies that will shape the future, accelerate their growth, and train outstanding talent. Will sat down with Equidate to share his biggest insights from his career, and tell us what excites him most in the market today. 

In the 90s, online dating was brand new and a lot of people thought it was a ridiculous concept. How did you spot the opportunity, and what made you confident in it? 

We’ve got an unusual story in that everyone who started the company was already married. We weren’t trying to solve a personal problem at all. Dave and I really wanted to found a tech company, and we both believed the internet was the future. AOLwas the largest internet company of the 1990s, so we started reading their SEC documents. At that time, AOL charged $4 an hour to be on their system. I read that half of their revenue came from ‘chat.’ That’s crazy. I started looking at AOL’s chat system and figured out what everyone was doing—they were trying to get a date! I thought to myself: if half the revenue of the largest company comes from people wanting to get a date, then we should do that on the internet, so when people migrate off AOL, we’ll have something that they want.

You must have encountered a lot of naysayers. 

When I told people what I was working on, they would physically flinch. You’d see people back up from the conversation. Even I had a hard time believing it. I was from a small town in Arkansas and I thought: what kind of idiot would put their name and picture on the internet and say that they needed a date? Part of it was convincing ourselves that people would do it. The need to find a mate is one of the most fundamental human drivers, so on that part of it, I knew I was correct. The part I didn’t know was if people would adopt this method culturally.

You’ve said in the past that your website at the time was terrible. Based on that experience, how do you think through user experience now?

You’ve either got to adopt the conventions that people are familiar with, so that they’ll use your system, or it has to be so revolutionary that they’ll adopt new behavior. But that’s one in a million. Honestly, I never try to overthink it. I just let my users tell me what they want. User experience is less about drawing a pretty screen (which is design) and more about understanding humans well enough that you can solve the right problem for them in a way that works. So a lot of it comes down to learning to listen effectively and ask questions.

What big lesson did you learn about leadership?

The first thing I learned to do was apologize effectively. If you’re going to screw up a lot—which I did—then being able to sincerely apologize and mean it will buy you a lot of time. At the time, my brother was doing the physical networking of the cables, since you had to build your own servers back then. One day, we ended up in a screaming match over something (in the middle of the office, very unprofessional) and the next thing I knew he was crying and running out of the building. I thought: if he quits, we’re screwed. I ran after him, got on my knees, and just said, “look, I realize I’m a bad boss; who have you worked for who’s any good at managing people? Because we’re going to hire him and you never have to talk to me again.” And the guy we hired was one of the best we ever had because he was great at managing people. If I hadn’t swallowed my pride and done that, we’d have been set back three or four of five months.

As an investor, which markets are you most excited about and looking to invest in? What are the biggest opportunities you see?

Machine learning is probably the biggest fundamental shift humanity will ever see. It’s as big or bigger than the internet. When you look at IOT, what it really means is that the cost of collecting information is going to zero. If the ability to interpret information and the cost of collecting information are both going to zero, then anything lost will be found, and anything we don’t know about will be observed. The implications of that are beyond crazy. If I were twenty-five again and looking for an opportunity, machine learning is where I would be searching.

Have you invested in cryptocurrency? 

Cryptocurrency is basically a new tech stack. If you look at it from that point of view, it’s about how to exchange things with people you don’t know without a central agency. Then you think: ok, I wonder what problems humans have that it could solve? That’s where it gets interesting.

But you’ve heard the hype around Bitcoin. Do you know how many Bitcoin transactions the planet can handle? 7 per second. That’s it. You couldn’t run Lake Village, Arkansas, on that rate. So, yes, it’s interesting, and I think it’s breakthrough technology, but bitcoin is only the beginning because it couldn’t run the global economy if it had to.

Is there an area of fintech you monitor closely? 

I struggle with fintech because it’s one of those things where a lot of the capital goes into the regulations. So, the valuations are high even though there’s no user traction. I think it has great value and is super important, but it’s just not something that you can put small amounts of capital into and sell.

Do you have any strong opinions on unicorn IPOs and whether this is something we can expect to see more of or less of? Should unicorns aim to IPO?

My theory is that since there’s so much money willing to invest in late stage tech, why would you IPO? Until that money goes away, companies are acting in their best interest by not IPO-ing. Late stage capital is allowing companies to stay private longer, and being private is easier.

Let’s talk about the founders you invest in. What is the biggest red flag you see?

The inability to talk flexibly about how to get to their outcome. If someone thinks that they already have all the answers and you need to just give them the money and go away, I think that that’s a ridiculous statement. No one survives contact with the marketplace intact. You have to adapt as information comes in.

How do you great founders motivate and retain talent?

The biggest thing is to attract people who can handle your management style. Changing is really difficult. Also, hire people who are better than you, and let them do their job. The best days of my life were when we hired people who could do things I couldn’t, so I didn’t have to even pretend to try.

What would you say are the key skills people need to be amazing start-up employees? 

There are four core skills, in my opinion, that make a start-up work. You can choose one or more of them to add value. First there are the engineering skills to build something. Then there are the sales/business skills—the hustle, if you will—to talk to human beings and make deals and move the business forward. The third is design, extracting from humans what to build and how to build it. Then there’s digital marketing. (Or, marketing in general—I don’t know why people differentiate between the two.)

Let’s talk about GrowthX. Why did you decide to train growth marketers from the ground up instead of being a traditional Venture Capitalist? 

The world doesn’t need another VC fund. There are plenty of them and they do a good job. We looked at incubators as well, but the world doesn’t need another incubator either. So, we said, “well, what is the hole?” The number one reason companies fail is market traction, so we decided to play there, in that no man’s land in between going through an incubator and getting your first venture round. During our first year, instead of a getting a negative return (which is normal in seed stage firms) we had a 21% return. 95% of that was with companies we helped with sales.

When we met Sean Sheppard, one of our founders, he had the most amazing framework for early stage sales I’d ever seen in my life. There’s a way to sell to people which isn’t about tricking them to buy something—but rather figuring out what their problems are. It’s a more humble approach to serving customers. We’ve built the fund around taking that knowledge and interjecting it into startups.

But don’t people always know when they’re being sold to?

At that point, you’re not selling them. You’re solving their problem. It’s such a different conversation. If you don’t solve their problems, they’re not a customer, and you shouldn’t be bothering them. It’s about working for your customers in a genuine way. Your ideal customer is the person you helped the most initially. Find that person who, if they knew you existed, would drive over and shove money into your hands just to get a solution.

What is your advice for digital growth?

In the digital frame, it’s basically mastering social in a meaningful, genuine way. The guy that I think is the genius on this is Gary Vaynerchuk, mainly because he embraces a social channel on its own terms and creates engaging content.

What does it mean, to ‘embrace’ a social channel?

Look at Twitter. It’s a short, ironic, smart-ass format. I like saying smart ass things, so now I have over 10,000 followers. Twitter is a good fit for me. But every brand has a different personality. You need to find a medium where expressing that personality comes off authentically. Then you can build up a dramatic following.

What would you say are the biggest lessons you’ve learned from your career?

The thing that people generally turn to me for is thinking through the “why”—starting with the real goal and then working backwards and trying to maximize the probability that you’ll get it. It’s strategic thinking. We didn’t start the dating site because I thought dating was cool, or that I wanted to get on the cover of some magazine. It was literally this: I wanted to start a successful business, and I didn’t have a lot of capital. I worked back through a series of logical steps, and dating seemed like a reasonable bet. You have to learn to think strategically, and not just do things you want to do.