Home Advice For The Young At Heart Entrepreneurs: Create A Founding Legend

Entrepreneurs: Create A Founding Legend


by Neil St. Clair, CEO of  AlleyWire

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I’m here to tell you a story about sacrifice. Normally I preach on video storytelling: “How to Tell a Meaningful Story on Video” or “3 Steps for Successful On-Camera Interviews,” for example, 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 — and I want to offer a humble suggestion about how you can 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 my Ivy League education on hold. As founder of AlleyWire, I’ve stopped funding my four-month-old daughter’s college fund to put it towards a company that I think will be her 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 in my life (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 to make my companies thrive—sometimes it’s worked, and sometimes it hasn’t.

As a founder you will win, but sometimes you will lose. And that loss can be profound. 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 pissed 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” above, and being honest, smart, and sprinkled with a bit of pixie-dust-luck, loyalty derives from some type of sacrifice (not manufactured, but distilled from an honest conviction and passion) that you as a founder make. This will become part of your founders’ lore—a creation myth so to speak.

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

Remember, just like making a video, life is all about telling an effective narrative to drive action and results. All the “famous” founders have a narrative of “sacrifice” that they can point to from their company’s early days:

– 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 White Knight.

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

My founding legend.

My founding legend at AlleyWire was just a few months back. 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 three times (once with our Director of Strategy on the phone to prep her pitch if I couldn’t arrive), ran off the road once, and averaged about 40mph the entire drive.

To say that I was stressed and in need of a beer is an understatement. But I arrived 15 minutes early before my pitch to a crowd of unforgiving contemporaries, my AlleyWire teammates and investors, and I believed that this death-defying personal sacrifice was worth it.

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.

My story above will be news to some of my team members reading this article. I’ve never asked for loyalty, but I hope this shows my team that I’m worth being loyal to. That in some way, I’ve earned their respect, time and effort, and if a day comes that I ask them to sacrifice, they will want to stick around.

So now I turn this question to my readers. Are you worth being loyal to? Are you willing to sacrifice above and beyond? Create your own founding legend.


neil st clair

Neil St. Clair is the Founding Correspondent & CEO of innovation-focused media outlet AlleyWire, as well as president of AW/CS, AlleyWire’s creative agency. He was previously an on-air correspondent for NY1and YNN, and is the founder of several other media and startup ventures.