Blog Post

Risk Everything

My story evolved over the course of eight years, but can be summarized in very few words. I founded a software company with technology I developed at NASA. I licensed the software, raised two rounds of venture capital, and ran the company for seven years. Then, as a result of increasing differences with my investors, it became clear that I needed to leave. End of story.

That was two years ago. I am often teased by the prospect of returning to business. But since then I have been dedicating time to things I never made time for before. I have invested in my personal relationships. I learned Spanish. I bought a half interest in a 50’ sailboat, and I am learning to sail.

*I have another story to tell,* one that is chronologically short. It transpired in less than an hour but it requires more words. It isn’t a story about me, but it left a mark on me. *We were sailing the boat to Belize* from Fort Lauderdale, in my first blue water trip.

With a *two person crew,* we had to take two-hour night watches. That meant two hours of sleep in between. REM was out of the question. At night, alone on deck, I developed an urge to whirl around and see who was behind me. Of course there was never any one there, we were hundreds of miles out to sea. I had heard that people get weird after days spent out of sight of land, and I was getting paranoid as a result of sleep deprivation.

Two days from Key West, just after dawn, *I saw a rock out in the distance off the starboard bow.* Had I added hallucinations to paranoia? We were in deep water; no islands or rocks charted anywhere. I peered through the binoculars. The rock looked like small boat. I hurried below to wake up my sailing partner, Dave, who has crossed many oceans and would know what to do. By the time we made it back the cockpit, there was not doubt: This was a small boat, with people inside, waving a red flag.

The prevailing wisdom for this seafaring situation is *“Don’t Stop.”* The possibility of armed pirates makes it unsafe, particularly for a small crew. But Dave and I hardly ever follow conventional wisdom. So we changed course to allow them to approach us.

When we were within 10 or 15 yards of the little boat, we saw that *there were actually 10 men on board, packed in like sardines.* Some lay in the bottom of their craft, the rest were standing. They were disheveled, dirty, a wild-looking bunch, and appeared in age from 20 to 40. They screamed hoarsely above the noise of their engine, which seemed to have been converted from a piece of farming equipment and was missing any semblance of an exhaust system.

*“Water! Agua! Water! Agua! Agua….”* There was a hysteria in those shouts of mixed Spanish and English that made me strangely uncomfortable. Something didn’t feel right about it, we both noticed. We prepared the can of mace, just in case. Dave tossed them a line, and indicated that they were to take it but hold their distance without coming closer than ten feet.

The conversation was limited, but we learned that *they were six days out of Havana.* They’d had no water in 24 hours. Five other vessels had passed them without stopping since they drank their last drops. That inexplicable ‘something’ in their shouts that didn’t ‘feel right’ was the sound of terror – the terror of those who believe they might die. Dave filled their five-gallon water jugs, urging them to drink at least one jug on the spot. We needed my Spanish to convince them that this was ok, that we would refill it. *They were in the mindset of conservation–or preservation.* They believed our water supply was limited.

*I asked if they needed food, they declined.* But we didn’t see any food in their boat, so I rushed below for provisions that, orginially packed for two, might be suitable to share between ten. I sorted through packages of gourmet cheese, piles of fresh vegetables (what were they going to do with a bag of arugula, an artichoke, or asparagus), bags of chips and roasted tomatillo salsa, microwave popcorn… I settled on fruit – to feed ten, I needed all of it. I poured a dozen apples and some oranges into one of those plastic grocery store bags, and added a box of saltines, and some chocolate. When we handed it over, they took it gratefully, with looks of wonder. They declined fuel, pointing proudly at their reserves. One made a gesture of lighting a cigarette. He still had some smokes, but no lighter. We found him one.

The only other thing they needed was to confirm their course. They were headed for Cancun. “Why Cancun?”, I asked. The response was simply, “Los Estados Unidos no son buenos para nosotros…” The U.S. Congress was debating legislation to build a wall across the Mexican border at the time, so they weren’t going to American shores. The GPS told us we were 60 miles due east of Cancun. Our Cuban friends had no GPS. They had no nautical chart. They had only a simple hiking compass, but they were more or less on course.

With water in their bellies and food in their boat, the men were beginning to sound friendly rather than frantic. A few kept asking about direction. *I began to discern that it was the youngest among them who was in charge.* He had a quiet confidence: He only needed to confirm his course _once._ The rest were less certain, maybe less familiar with the sea and the currents. Maybe a little less confident in their captain than when they had first set out. But with 60 miles to go, at four knots they would arrive in Cancun a few hours after dark. The luminescence of the city lights over the water would guide them after sunset.

When they set off again, releasing our line with smiles, renewed hope in their eyes, and calls of “Vayan con Dios”, my eyes filled with tears. (They sometimes still do when I think about it.) I wonder what has happened to them. I hope they made it.

*I think of myself as a risk-taker. An inventor. A dreamer even:* I sail open water; I scuba dive with sharks; I founded a company; I am an entrepreneur. But I re-learned a few things about risk-taking and dream-seeking from those men, in that hour, on the open ocean. I think these are things valuable to all risk-takers or dreamers — to all founders.

*Boldness* is risking everything, meaning that which you _cannot affford to lose_, to pursue a dream.
*Inventiveness* is finding the will to be creative when necessity demands it– not when it comes to you.
*Motivation* is finding the spirit to hang together when resources are depleted and plans run awry.
*Honor* is maintaining a sense of fair play and not asking for more than you need–even when it would be excusable.
*Leadership* Real leadership is demonstrated when one at the ‘helm’ finds the confidence not to waver, even when the confidence of the team has wavered.
*Luck* On a day when it really counted, they had some of it. But it dawns on me that luck is just the product of all these other qualities. (Think about this the next time you feel ‘lucky,’ or dismiss someone else’s success as ‘lucky.’)

When I share this story with other sailors, they are universally aghast that we helped these refugees. But I’m proud that we took a risk to alter a situation that might have meant life or death to someone else. I didn’t know I was capable of that before. And I’ve never stopped thinking about the qualities of these men: the intense drive to achieve something better and to risk everything to do so. *I can’t help wondering if my own business venture might have turned out differently* if I had been able to instill in my team more of a make-it-together-
or-die-trying attitude…or maybe if we had had just one more lucky day.

9 Responses to “Risk Everything”

  1. Great story, Ursula.

    One of the measures of risk, which we rarely examine closely, is relevant to your story, and this the full extent and meaning of the risk being taken by a person (people) in a given situation.

    A venture fund may be willing to take risks on unproved startups, but how much risk are they really taking, using OPM spread across multiple investments?

    An angel or entrepreneur may be risking their own funds or savings, but they aren’t risking their lives or even their future ability to earn a living should they fail.

    Your story tells of people willing to risk everything, including their lives, not even for financial reward, perhaps, but only to live in freedom or to have access to expanded opportunity.

    This view of risk helps explain why the hardest person to compete against is one who has nothing to lose. When you have nothing to lose but your life, then you’re risking the most valuable thing of all.


  2. gvenkatesh

    I wonder how realistic it is to compare a start-up do-or-die-trying to these people on the boat where it is the literal truth. There is no practical way to create the sense of desperation, despair and loss of hope that drives such feats nor is it necessarily the right thing to do for a startup. All entrepreneurs have viable choices to make unlike these people. There is no such thing as “risking everything” for educated people in the land of opportunities (unless you become a test pilot for an experimental aircraft company or something similar).

    The relevance to entrepreneurship and risk taking that I noticed in your story actually has to do with the quick decision you had to make whether to approach the boat. We are all faced with making these kinds of decisions every day, especially as a founder or an executive. It could have turned out very badly for either boats based on that decision. This is where a good mix of intuition, courage, lack of fear of failure, wisdom and blind luck can result in good decisions (in retrospect). You don’t always have the information to make a fully-informed decision.

    Building a team of people that individually can make such decisions in their respective roles from top to bottom would be the “dream team” for a startup. And if I knew how to do it….}

  3. yousurftubes

    Ursula, simply courageous. It is so inspiring to read your experience. Kudos to both you and Dave for your faith in the human spirit! I wish we could all have such conviction. I only wonder what became of the ten men on the boat. What a tale they must be telling about you two.

  4. mistone

    Kind of took my breath away.

    While act of leaving a +100k job to risk making millions does not have the same heroic undertone anymore, your leadership quality takeaways are potent.}