Alex Harrington is an accomplished technology founder and executive with 20+ years leading start-ups and growth technology enterprises. Prior to SecureCo, Alex was Chief Executive Officer and board member of PeerStream, Inc., a public communications technology company.

Alex previously served as CEO of MeetMoi, LLC, a mobile social platform, prior to its sale to Match.com. Prior to that, Alex served as the Senior Vice President of Strategy and Operations for Zagat Survey, where he oversaw a transformation of the digital business which ultimately culminated in the company’s sale to Google.

Alex holds a MBA from the Wharton School and a BA from Williams College.

Where did the idea for SecureCo come from?

SecureCo’s co-founder and I ran PeerStream as CEO and CTO, a business that provides live video communication apps to hundreds of millions of end users around the world. In the Middle East and Asia, we had become a political speech platform, which began to elicit cyber-attacks from nation-state actors who wanted to block or take down our service and go after our end users. We had to develop military-grade defensive capabilities in order to maintain uptime, protect the privacy and identity of our users, and penetrate through national firewalls intended to block our service. We had conviction that the knowhow that protected PeerStream would be valuable to other organizations, so we bought out the IP and the team to launch SecureCo as an independent company.

What does your typical day look like and how do you make it productive?

As the CEO of a small growing business, I wear nearly every hat. In a single day I will be working on product, technology, marketing, sales, finance and customer service. A versatile skill base is must, time management skills and the ability to switch context are all critical. One you get used to a start-up environment, it’s hard to go back to a role with a narrow scope and long planning cycles.

How do you bring ideas to life?

Inspiration for new business ideas comes from many sources. Startups are unbounded by a long operating history, freeing them to explore nearly all avenues of opportunity. Decision-making is extremely agile in a startup environment, and the organization can turn on a dime to capitalize on an opportunity or new customer requirement. However, the temptation to chase every bright shiny object has been the undoing of many promising young companies. Large organizations have checks and balances against reckless course changes, but this can also snuff out innovation. The challenge of a start-up is to figure out when to exercise the capacity for agility and innovation, and when to stick to your focus or niche.

What’s one trend that excites you?

AI-enabled, self-driving cars are not very far out in the future. I believe this will be even more transformative to our lives than the advent of the smartphone. Traffic will flow much, much faster once human error is removed. People will travel and commute much longer distances, because the driver is now a passenger who can spend time productively. Cars will be designed with seats that fold flat for sleeping. Urban street parking becomes obsolete since cars would find some inconspicuous underground parking until summoned. On the downside, driving as a career or side gig becomes superfluous, which will cause economic displacement for millions of people.

What is one habit of yours that makes you more productive as an entrepreneur?

I am a compulsive list maker, to keep tabs on and prioritize the dozens of simultaneous work streams and the associated tasks.

What advice would you give your younger self?

Be bolder. Overcome the imposter syndrome – most people will give you the benefit of the doubt. Youth and inexperience can be an asset – older, more experienced people are often seeking to partner with energetic, coachable talent. Seek out experienced mentors and don’t hesitate to share your insecurities. Forcing yourself to confront your limitations will clarify that most of them are surmountable.

Tell us something that’s true that almost nobody agrees with you on.

Conventional wisdom says that effective people clear out their inbox or complete their to do list. I believe the opposite is true. At all times we are swamped with rather unimportant tasks that are easy to accomplish. It’s very tempting to clear the decks and push off the difficult, yet very important stuff. The truly disciplined thing to do is prioritize what truly creates value and push off those hundreds of minutiae until failure to complete them has consequences.

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

Spread your bets out, preferable at large scale. I wasn’t trained in sales but learned the hard way what every entry level salesperson knows. Most things in business are a numbers game, and you can’t count on any one opportunity coming through for you, no matter how certain it seems. Figuring out how to scale your outreach and widening the top of your prospect funnel is a big part of making sure that your outcomes line up with your expectations.

What is one strategy that has helped you grow your business?

Invest in relationships. To some people this comes naturally. But to others who are more introverted, and would rather work with code or numbers, other than people. The fact is all opportunities come from people and the goodwill you generate with them. Making a personal connection with your business associates can make a world of difference, since the conventional wisdom is true – people don’t remember what you said, they remember how you make them feel.

What is one failure you had as an entrepreneur, and how did you overcome it?

Taking the long view on your life and career, failure is a much more effective learning experience than success. But it usually feels awful when you are going through it. Still, even in the moment of failure, there are almost always ways of making lemonade out of lemons. Twitter and Slack were originally both pivots from failed ventures. Often, even in failure, there are some great things that you’ve created that can form the nucleus of a new, potentially much more successful venture. Twice in my career I have built successful startups by extracting assets and IP out of another struggling business.

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

There is a huge gap between the current state of cybersecurity awareness and training needs. This goes for consumer awareness, non-technical employee training, staffing and training for entry level cyber jobs. Presently there are approximately 600,000 unfilled cyber jobs in the U.S., but this figure will grow into the millions in a few years. Businesses that support the pipeline of personnel to fill these jobs should do quite well.

What is the best $100 you recently spent? What and why?

Airpods. I’m on the phone constantly, and absolutely need to be hands free and to be able to move around, potentially out of range of a speakerphone. I also use the downtime I have, while doing perfunctory tasks to listen to podcasts and audiobooks. They are as indispensable to me as shoes.

What is one piece of software or a web service that helps you be productive?

It’s tough to choose only one. Calendly is a scheduling solution that I’ve found to be very useful, especially to allow third parties to schedule the mutually available time of my partner and me.

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

A brilliant finance professor I had at Wharton recommended The Remains of the Day by Kazuo Ishiguro to all his students. Strangely, it’s not a business book at all; it’s about a seemingly trivial set of occurrences in the life of an English butler. But the narrator meditates profoundly on topics like dedication to a professional craft, work-life balance, and perceiving the impact of your work on the broader world around you. It is utterly captivating – the only novel I’ve ever read in a single sitting.

What is your favorite quote?

“No one can make you feel inferior without your consent.” This is such a powerful statement by Eleanor Roosevelt, which applies to both personal and professional life. Building a business up from nothing means you are the smallest company on the block and will be for a long time. It’s easy to feel inferior when you have no market power and are sometimes scratching to survive. But the innovation and entrepreneurial audacity of small businesses can be a superpower, and big company leaders admire and seek alignment with these characteristics.

Key Learnings:

• Successful entrepreneurship requires not just bold thinking, but bold execution. Key thoughts from this interview:
• The superpower of entrepreneurs is their ability to boldly embrace innovation and sell a compelling vision of the future. These qualities will draw admiration that compensate for other shortcomings of your startup.
• Nelson Mandela said, “I never lose, I either win or learn.” This is true in entrepreneurship if you take measured bets and fail fast. There is no better teacher than failure, and often successful businesses emerge from failed projects.
• Never place your bets on one or two big deals – diversify your risk by scaling your outreach.
• Confidence and resilience are so important in facing off with larger competitors or surmounting the imposter syndrome. While some people have these as inborn traits, I do believe that you can cultivate these attributes.