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

McCann 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.

McCann’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.

The 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.

When 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 →

Raw notes/timestamps:  [spoiler]

Raw Notes and Time Stamps

Founder of several tech companies
Gist – sold to Blackberry
RivalIQ
Started successful companies – succeeded wildly
Failed – willing to share learnings
America’s cups – sailing

1:05 When did you first get that entrepreneurial bug?

I got it very, very early. Around 12. I had my own grass-cutting and yard work business. “I recently found a business card that I made in printing class on a real hand-printing press by setting my own type in middle school.” I started another company when I was 15 around boat maintenance – grew up in northern Indiana on Lake Michigan. “The feeling of independence and the feeling of being able to control my own destiny is something that has always been important to me.”

2:06 After graduating in Purdue and becoming a mechanical engineer, he quit to do professional sailing, leaving the technology space for the mid 90s. Very successful at that.

The Internet was happening and I was starting to get a little bit bored with sailing so I started my first real technology company which was a web development company. Built a lot of the early sites for the marine industry. Mid to late 90s. The ideas for my first real software startup came in that time frame. We started that in 1998 and it wasn’t even venture backed, it was angel funded.

3:21 Sailing “open waters” – blue ocean

A lot of people in the startup community have actually had a similar background of doing some sailing. Ted Turner.

Parallels with entrepreneurship? – 4:00 – Blog posts. “How Winning the America’s Cup is like running a successful startup.” Funny enough I wrote that inspired by Larry Ellison and the Oracle team winning the last America’s Cup. He hired me and five other guys off the ‘95 America’s Cup team to get him into sailing and we went on to win five world championships for Larry, and then from there he wanted to step up to the biggest game in sailing which is the Americas cup.

Answer – 4:57.

• That you have to have a hypothesis on the areas where you want to innovate. In sailing – it could be the sail design or the boat design or the crew
• The more money you have the more different areas you can experiment in so you can run many different experiments at the same time
• Once you have a hypothesis you go try to hire the best engineers you can. If you can hire those engineers ahead of your competition you can gain an advantage.
• Figure out how to align all those different experiments so that you don’t get overly confused in one category or another and line them up from a timeline perspective
• And in the case of the America’s cup or any competitive situation you have a timeline. When is the thing going to happen?
• Parallels with startups – when am I going to run out of money or when do I have to raise more money?
• What are the things I think I need to achieve by that time – how do I measure those?
• Where do I run the experiments and for how long – keep running an experiment, call that category off in a category or that category becomes my competitive advantage. 

6:12 – Ever on a boat and felt like quitting might be dangerous?

A few times when it was dangerous – really dangerous.  The Sydney Hobart race – 2nd deadliest sailboat race ever. Seven people died. I was on Sayonara with Larry Ellison and a bunch of guys We probably had the best team on the water, all pros, lots of experience and it was challenging for us. – won

6:49 I was doing the Around the World race, and we had it effectively wrapped up. We had created a huge advantage, and the mast fell down. Once they came back to safe, where we weren’t of sinking, almost everyone on the team wanted to quit. Like, “I’m done.” Because we were gonna win, then we didn’t get to win. Took us about 3 days to get from where to the mast fell down to where we got to land. But in that time the skipper, and “all of us went through this transformation of wanting to quit and give up and go home to finding something we could salvage. Could we still win the last leg, could we be the top of the bottom pack? Could we satisfy our sponsors? Could we achieve our own personal goals of actually completing the Around the World Sailboat race?”

“Slowly but surely the team made this 180 degree turn to be really enthused about how do we achieve those things. A resetting of the goal posts. We in fact did go on and win the last leg quite convincingly and achieved a lot of those goals.

8:12 Did you take that same strategy during your first internet venture, Helpshare?

Didn’t know what I was doing very much, I was inexperienced, didn’t know what we were building, did know how to build it, certainly didn’t know how to raise money very well. In the midst of the dot com boom – late 90s. To be inexperienced in that time – parallels to today. to see Uber, Airbnb, Snapchat, Whatsapp – companies going from nothing to being worth billions of dollars in a short period of time. In that situation as a first time entrepreneur you have this sense like, what am I doing right, what am I doing wrong? At least I’m happy to be in the space. At least I’m happy to trying  innovate

9:16 “Helpshare was a reasonably good idea, the implementation was reasonably good, the go-to-market strategy was okay. We really kind of missed out on timing. We had built the company properly, we had planned to raise venture money, and we just showed up at the wrong time. Right when the dot com crash happened was when we were planning to go raise money.

Now I’m 10 or 12 years older, this is my 5th startup I’m on with RivalIQ, I’m a lot smarter and have surrounded myself with lots of other smart people in Seattle. With a lot more experience we’re doing a lot differently now.

10:08 “Failure and success and resetting what success looks like – I think that is something that goes into software startups.”10:30 “The people who can both set the appropriate level of goals – because if you’re only achieving at 20%, the goal’s too hard. If you’re achieving at 100%, the goal’s too easy. The process of resetting the goals is really important. Building a rhythm and a team where it’s okay to fail a little bit. It’s okay for individuals to fail here and there, the team has to pull everybody up together. The team also has to push everyone to keep setting their own individual goals and the collective goals a little higher every sprint you put together.”

11:12 How were you able to move on from the lack of success with Helpshare?

11:45 “It took a long time.” “We needed time to recharge.” Had spent savings,. Founded with brother – both families were overextended financially and emotionally. Ended up at Microsoft. recharged financially and emotionally.

3 years. The whole first year was overwhelming since I’d never worked in a big software company. I learned a tremendous amount. Recharged intellectually – learning things that are different than what you need to learn for a startup.

13:31 But – I was doing my own innovations. I was building new businesses around the core exchange product I was working on. I was thinking about new international markets. My manager and team were quite supportive of that effort of staying entrepreneurial within the constructs of a big company with a big product. Within Microsoft a few of us built a program to offer venture capitalists the opportunity to introduce Exchange’s 125 million global customers to their companies who could build something to fill a niche within Exchange.

One thing led to another and I was invited by one of the VCs that we worked with to become an entrepreneur-in-residence.

16:52 How did you go about starting Gist, knowing that competitors out there in that space?

Slightly different premise in mind – bring me relevant news. Hypothesis, prototypes

– Connect to the inbox – find all the companies and people that matter to me – then hit the Google news Api and bring me back a bunch of news. Finding me news about people I cared about. Then broadened to Content about or BY someone.

– Understand customers and what they care about – build stronger relationships – more than just news discovery engine – evolved into personal relationship manager

All those first wave in that space are gone – acquired

Contact management – the problem is still there

20:47 On board of FullContact – first trying to solve the contact management problem. Started next wave – socially enhancing them – here’s their photo and their Linkedin and their last 5 tweets – super valuable

Next wave of social crm/social contact managers

21:41 What would you say to someone who is too busy building product to go out and network?

“Success in business is directly correlated to the size and strength of your professional network.”

Size+strength. “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.”

Recruiting – recruit great people. 2nd and 3rd degree connections

22:56 Key Influencers – who will drive that conversation. Build a relationship with them. Identify them and what they care about, then figure out how you add value to what they’re doing. They will be important part of product development cycle – and/or in your marketing and customer acquisition.

Fundraising/investors category – same thing – understand who they are, what they care about. Build a relationship before you ask for money. You have to ask for advice before you ask for money

25:22 – Is there a recent example you can think of where a contact turned into a relationship and that resulted directly in a new hire, a new customer, a investor.

Customer success

27:59 What is your grand vision for RivalIQ

Premise that digital marketing is really challenging – what channel to use, how am I doing? Am I doing a good job? What is a good job? Many different choices for where they spend their time and where they spend their money. Easy to compare to how competitors – web presence, search, social. What it does today.

29:21 -Long term vision – how do we continue to help you make the right decisions. Where to focus. Organic search – “For sure, almost every company is going to have to do a decent job on SEO and organic search.”  Next, probably 2 channels – what matters. What post content is resonating, how frequent.  That problem will never go away – there will always be more complexity and more channels.

31:45 – Recommend that entrepreneurs go to channels where their competitors are, or go to channels that are underutilized and dominate there?

Depends on skill and interest of the company. 32:36 “It’s an 80/20 rule. 80% of your effort has to be in support of the normal channels because all your competitors have already built a customer base there. If you’re not there, then you’re missing out. You have to do enough to play along. The other 20% is experimentation. Let’s try something different.”

RivalIQ – 2 landscapes – competitive and comparative – latter that are awesome at marketing to your customer but are not your competitor. Who markets to my audience, or look at channel.

Long term vision – drive best practices – here’s who you should compare to, here’s what you should do differently to win with your marketing. Do it in a very data-driven way.

36:01 – What have you seen successful entrepreneurs do when it comes to social and content?

Very small company – pick a couple of keywords that matter to us. Then, find the key influencers about each of those keywords. Now I know 5 or 10 twitter people who are influencers for those keywords. Then, build into twitter list then you have a stream of content which is relevant to the keywords I care about.

37:29  The T.A. McCann 5-3-2 Social Media Rule – “for every 10 posts that I make (on Twitter, LinkedIn, Facebook, or whatever your most important channels are), 5 of them should be about the space by one of those influencers. Retweet that stuff to my audience. Building relationships [/spoiler]