From Open Waters to Red Oceans: T.A. McCann’s Adventure as a Successful Sailor and Entrepreneur

T.A. McCann is one of the few people on the planet who can claim astronomical success in not one but two areas; in his case, sailing AND entrepreneurship. But are they that different? I sat down with the tech company founder and America’s Cup winner about both bouncing back from failure and tips for achieving success.

Watch the full interview with T.A. McCann here:

Adventures in Entrepreneurship and Sailing with T.A. McCann

sailing and entrepreneurshipMcCann got the entrepreneurial bug around the tender age of 12 when he started a lawn care business: “The feeling of independence and being able to control my own destiny has always been important to me.” Perhaps that’s why, after graduating from Purdue (which is still going strong when it comes to shaping entrepreneurs!) and becoming a mechanical engineer, he quit to pursue the freedom of the open waters. An accomplished professional sailor, he won the America’s Cup in 1992.

What do Sailing and Entrepreneurship Have in Common?

Quite a lot, in fact! In his blog post on the subject, McCann observes that the skill, engineering excellence and perseverance shown by Larry Ellison and his victorious Oracle Team USA are “all things that go into a building a successful startup.” From finding a competitive advantage to working under a deadline, watch McCann draw all the parallels →

“If you’re only achieving at 20%, the goal is too hard. If you’re achieving at 100%, then the goal is too easy.”

-T.A. McCann, Sailor / Entrepreneur / Investor

Resetting the Goal Posts.

TA MccannMcCann’s sailing career was not without some setbacks. When competing in the Whitbread Round the World Race (now called the Volvo Ocean Race), his team was closing in on victory when suddenly, the mast fell down. Bitterly disappointed, almost everyone on the team wanted to quit. But in the three days it took to get back to land, a transformation from despair to hope took place: “We tried to find what we could salvage. Could we still win the last leg? Could we actually complete the race?” After resetting the goal posts, the team did in fact win the last leg handily and achieved a lot of reset goals.

“We just showed up at the wrong time.”

Not every entrepreneurial venture was a success, either. McCann returned to the tech world from sailing in the late 90s – in the midst of the dot-com bubble – with a startup called Helpshare: “It was a reasonably good idea, and we had built the company properly, but right when we were planning to go raise money, the crash happened.”

The Case For Corporate Experience.

ta-mccann-americas-cupThe loss was devastating, and McCann ended up joining Microsoft. During his three years there, he financially and emotionally recharged while still innovating and learning skills on the scale of a large company, “things that are different than what you need to learn for a startup,” like how to build software for hundreds of millions of customers in 123 languages. Eventually, a venture capitalist McCann had worked with through the product he had built for Microsoft Exchange invited him to become an entrepreneur-in-residence.

Entering a Red Ocean.

In 2008, McCann launched Gist amid several competitors already in the content discovery space. It started with the goal bringing users relevant news but evolved, using integrations with Google’s and Twitter’s APIs, into a social address book: “If I have all of my contacts in one place, and the system can give me news both about them and by them, then I can use to better understand them, and by understanding them I can build better relationships with them.” Through consistent customer feedback, Gist evolved into a relationship manager and caught RIM’s eye, which acquired the company in 2011.

The Importance of Building Relationships.

rival iq ta mccannWhen I asked him for advice he would give to entrepreneurs, McCann underscored the importance of building relationships for recruiting, reaching thought leaders, courting investors, and finding customers: “The stronger a relationship is, the more likely someone is going to do something for you or recommend you or your product to somebody else.” His most recent tech venture, Rival IQ (which we use at Verge, and I highly recommend), can help you learn how to best build relationships with customers through data-driven marketing. McCann also shared his 5-3-2 Rule for building relationships on social media. Watch him explain the strategy →

Want to learn even more from T.A. McCann?

Join 1,000 founders, investors, and builders at this year’s Innovation Showcase in July! A limited number of Early-Bird tickets are available for the full conference with more than 70 fundable companies. Reserve your spot here →

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About Matt Hunckler
Matt Hunckler
Matt's a founder and organizer at Verge. He's a connecter, writer, and habitual start-upper.
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