Why You Need a Founding Legend

By Neil St. Clair

This article was originally published on Forbes.com (January 7, 2015)

I’m here to tell you a story about sacrifice. Normally I preach on marketing philosophy: e.g. "How Digital Marketing is Destroying Your Business," but I want to step back and reflect as a founder. I’m offering a cautionary tale for both current, first-time founders and those thinking of stepping up to the entrepreneurial plate. I want to bring you to the realities of the world you’re entering — not scare you off, mind you— and hope to offer a humble suggestion about how you might build loyalty amongst all those you’ve asked to come on your startup journey.

Are you willing to make sacrifices?

I’ve started several companies, and for each of them I’ve had to sacrifice something. In one instance, I gave up my comfortable six-figure-a-year-job. Another time, I put an Ivy League education on hold. As founder of AlleyWire, I temporarily stopped funding my  daughter’s college fund to put it towards a company that I think will be her larger legacy.

As a founder I’ve missed dinners, birthdays, anniversaries and a lot of the “fun” things in life. I’ve been threatened with lawsuits, physical harm and even damaged (temporarily) some of my most important relationships (oh, and I’ve put on 20 pounds since becoming an entrepreneur, but that might just be a part of getting older). I’ve maxed out credit cards, credit lines, and friendships.

In the simplest of terms, I’ve sacrificed time and money in the honest belief that I would make my companies thrive—sometimes it’s worked, and sometimes it hasn’t.

As a founder you will win, but often you will lose. And that loss can be profound.

Life is all about telling an effective narrative to drive action and results. 

Now that I’ve got your eyes wide with fear, I’m going to bring down the hammer: What I’ve described are just the table stakes for becoming a founder. These are things you must do to make your company survive past its first few months. And guess what? No one will say thank you. They will be annoyed when payroll is late, they will question if you’re working hard enough, and they will leave to go to a more stable endeavor—despite your personal sacrifice.

Does it sound fair? You’re damn right it is. You’ve taken on this risk, and asked people to risk alongside you. Don’t expect sympathy or compassion. But there is something you can do to help engender loyalty. And loyalty, above all else, is what you will need to make your sacrifice worthwhile.

Why you need a founding legend

Now aside from the sacrificial “must dos,” and having the requisite honesty, intelligence, and sprinkled-with-a bit-of-pixie-dust-luck, loyalty derives from some type of sacrifice that you as a founder make. Not a manufactured sacrifice, but distilled from an honest conviction and passion. This will become part of your founders’ lore—a personal creation myth, wrought from reality, so to speak.

The founding legend of Rome--Romulus, Remus and the She-Wolf--sustained an empire. Will your story sustain yours?

Life is all about telling an effective narrative to drive action and results. All the “famous” founders have a narrative of “sacrifice” that evinces this:

  • Zuckerburg dropped out of Harvard and moved to California

  • Fred Smith gambled the last $5,000 of FedEx money to pay a fuel bill (by the way, he played blackjack and won around $30,000).

  • Steve Jobs was the sacrificial lamb at Apple and pushed out of the company he founded before coming back as their Knight Errant.

What story will you tell when there’s a chance you could lose it all?

My founding legend

My founding legend at AlleyWire came in February 2014. We were invited to pitch at Ultra Light Startups, which I considered a great privilege.

I usually split my time between New York and Boston; however, one of the worst snowstorms of the year hit the Northeast the night before the event. The roads were a mess, and it certainly wasn’t advisable to be on I-95 for 200-plus miles.

My wife and mother were both against the trip, and they were right. But, I’m impetuous, obstinate, and also passionate about my company—so I decided to go.

I left Boston at noon and arrived at the ULS pitch event around 8 p.m. (a trip that usually takes about four hours). On my way down I had spun my car out no less than three times (once with our Director of Strategy on the phone to prep her on the pitch if I couldn’t arrive).

To say that I was stressed and in need of a stiff drink or some Colorado Courtesy is an understatement. But still I arrived 15 minutes directly before my pitch. Awaiting me was a crowd of unforgiving contemporaries, my AlleyWire teammates and a slew of steely-eyed investors. Do I believe that this death-defying personal sacrifice was worth it? Channeling my inner Robert Evans: You better believe I do.

Now this might be some wishful thinking, but I like to think that this moment brought a sense of camaraderie and loyalty to our team. We’re all risk-takers rowing together in the AlleyWire long boat.

I’ve never outrightly asked any team member for loyalty, but hopefully this little piece of entrepreneurial theater shows them that I’m worth being loyal to. That, in some way, I’ve earned their respect, and if a day comes that I need to ask them to sacrifice, they'll oblige and carry on once more unto the breach.

So stiffen the sinews...

So now I turn this question to my Forbes readers. Are you worth being loyal to? Are you willing to sacrifice above and beyond? To create your own founding legend no matter the cost? If so, then maybe, just maybe, you are, to paraphrase O'Shaughnessy: a music-maker and a dreamer of dreams.


Neil St. Clair is a respected social entrepreneur, journalist, and philanthropist. He is currently CEO & Founder of social change consultancy, NES Impact as well as fear-focused venture studio, Notimor. An advocate for children and gender equity, he founded and chairs The NextMen Foundation. Follow him on IG @neilstclair

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N.B. Regarding certain quotations used on this site: I recognize the modern controversy following some of the quoted figures. I further recognize the potentially harmful beliefs these figures held in their time. In quoting them, it is not my intention to glorify or demonize. Rather, I cite their discrete thoughts, which represent a moment of interesting thinking, as separate from their total biography.

© Neil St. Clair, 2020-2025

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