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Interview with Braintree CEO Bill Ready: So You Want To Be An Entrepreneur?

Oct. 6, 2012
Personal Finance
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CEO Bill Ready is a veteran of the startup scene – Braintree is his fourth early-stage company. Braintree provides online and mobile payment technology to companies like OpenTable,, Airbnb, Uber, Angry Birds, and Living Social. We were fortunate enough to catch Bill for a peek into his entrepreneurial journey.

Tell us a little about your career so far.

BR: I began my career as an engineer. I was a computer science major at the University of Louisville, and became the first engineer at Netzee, a banking software startup. Netzee ultimately went public in November 1999, in the midst of the dot com boom. I  later joined emphesys, a digital health plan company, that merged in 2002 with Humana. That’s when I took a break from the entrepreneurial world by going to Harvard Business School, to sharpen my pencil a little and get smarter. After HBS, I joined McKinsey. But I still loved early stage, and left McKinsey after three years to run iPay Technologies, a bank payments processer, before selling the company. After iPay, I joined Accel as an Executive in Residence, and after they invested in Braintree, came on as CEO.

Wow – that’s quite a career so far. What did the HBS and McKinsey experiences add to your entrepreneurial toolkit?

BR: Before I went to HBS, I was a decent engineer and a good product guy. I had been scrappy and resourceful, and these traits had helped me succeed. HBS and McKinsey helped bring a structured approach to looking at a business and thinking through growth plans in a more refined and analytical way. The analytics alone are not enough to be successful – you have to be willing to roll up your sleeves to build a great business, but without HBS, I would have remained a good product and engineering guy, rather than becoming someone who can run a business.

Before the Accel investment, Braintree had been bootstrapped. Talk us through the pros and cons of bootstrapping vs. taking investor money. 

BR: Bootstrapping pushes you to be more thoughtful about efficient ways to grow the business, e.g. using viral vs. traditional expensive marketing. When you have funding immediately, you may delay or neglect monetization. But if you have a big idea or opportunity, funding can really accelerate your progress. The Accel investment brought both resources and a great partner to Braintree. Accel has been very helpful in recruiting and helping us build out the team. A bootstrapping mentality, coupled with resources and a great partner are like have having an entrepreneurial spirit coupled with the rigor of HBS/McKinsey training. It maximizes your chances for success.

Braintree is taking on a pretty ambitious goal, in trying to unseat PayPal as the payments platform of choice for ecommerce. What are some of the key features that differentiate your product? 

BR: The best way to think about this is by using what happened in the mobile space as an analogue. Before the iOS and Android platforms came along, you could build a mobile app, it was just much more complicated because in order to do so, you had to deal with the underlying complexity of the telecom model. Once iOS and Android came along, 2 guys in a garage could build something that used complex GPS functionality without having to know anything about cell signals. And the 2 guys in a garage are using the exact same platform that large companies like Facebook use to build their mobile apps. The platform allows you to abstract away the underlying complexity.

In the payments space, if you’re a startup, you go with PayPal because there’s nowhere else to go. PayPal started as a payments solution for eBay sellers, so it’s aimed at small businesses. Let’s say you start getting more volume, or want to have more control over your checkout process. You then migrate to which owns the middle market in payments. Your company then grows more, and you want the ability to start taking international payments. You then migrate again to Cybersource or Paymentech, which are both owned by large corporations (Visa and Chase respectively) and generally won’t talk to you unless you’re above a certain size. At Braintree, we don’t think your access to tools should be a function of your company size – there should be no need for multiple migrations. We offer the rapidity of setup that PayPal has, with the features of bigger systems. And then we pair it with Zappos-like customer support. 95% of your problems we solve through better software, and that last 5%, we take care of with exceptional service because when there is a fraud problem, you want to talk to a real live person!

You’ve had a lot of success in your entrepreneurial career. What advice do you have for folks who are starting out? 

BR: Any time you pursue something entrepreneurial, you’re going to be taking a meaningful risk and incurring the opportunity cost of a regular salaried job. You need to make sure you’re passionate about the opportunity – if you can’t sleep at night because you’re not pursuing it, that’s when to take the plunge. Because there are a lot of ups and downs and failures to deal with. There is no “sure thing”. You’ll have to toil through challenges to get there. I’ve had some successes, but dealt with tough times – the dotcom bubble burst soon after Netzee went public, the September 11 attacks occurred soon after I joined emphesys, and I started at iPay, a business that sells to banks in Jan 2008, right before the financial crisis. If you have conviction about what you’re doing, it makes it easier to weather the ups and downs.