John M. Dillard is the CEO of ThreatSwitch, a software plaform that helps companies get and stay compliant with security regulations and defend against insider threats. Throughout his career at the CIA, U.S. Navy, and several Fortune 500 companies, John helps leaders understand the threats to both their security and their business models. John is also the author of Microslices and runs workshops to help entrepreneurs adapt to disruptive change to white-collar work. From the CIA to NASA, from ChevronTexaco to Entrepreneurs’ Organization, John has helped top leaders and top entrepreneurs adapt to rapid change in technology, threats, and competition. Follow him @johndillard.
Who is your hero? (In business, life, or both.)
Not too many people have had a hand in transforming three different industries, but Elon Musk has. His mix of dissatisfaction with the status quo and optimism for the future is exceptional. He’s also kind of a geek, which I can relate to.
What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?
Crowds are stupid. Once I began to engage with other entrepreneurs in peer-to-peer learning, I quickly learned that the best ones watched where the herd was going, and then went in the opposite direction (or, chose a different route). The courage to see what most people are doing, and then choose a better way, is the single most important trait for entrepreneurial success.
What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?
Failing to build a strong sales culture. In my first company, a security-focused consulting firm, I was laser-focused on hiring the sharpest security and operations analytical talent available. What I failed to realize is that those same people often never develop sales traits like empathy, listening, and fearlessness. That mistake cost me several key contracts and almost killed the company. I learned that to grow, the team has to have a “personality” for growth that makes us wake up in the morning wanting to talk to anyone who will listen.
What do you do during the first hour of your business day and why?
I read, and then I read some more. Any day that I don’t spend at least 1-2 hours reading is a bad day. If you’re not learning, you’re dying.
What’s your best financial/cash-flow related tip for entrepreneurs just getting started?
You can build an MVP (or any basic business idea) without taking anyone else’s money. Build that basic viable product or service, prove that it works, line up the first few customers, and then figure out what capital you need. Otherwise, you’re going to take on dangerous debt, give away too much equity, or ruin a friendship or family relationship.
Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?
Figure out how your company will be disrupted, because it will be. I know, it’s a buzzword, but the pace of change driven by automation, data science, and culture means that every company (and I mean every company) is vulnerable. The difference between winners and losers in the next 20 years will be defined by which companies attack themselves versus those that wait for someone else to do it for them.
What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?
A wise mentor once told me that everyone’s success is a Venn diagram composed of satisfaction, compensation, and recognition — and the secret to achieving it is to know the shape of yours and that of everyone’s around you.
My Venn diagram is heavily weighted toward satisfaction, which means that I am successful when I love what I’m doing and why I’m doing it. The bad news is that I’ll never be “finished.” But the good news is that I’m already there!
