Uncle Saul

Need straight-talking advice from a serial entrepreneur? Ask Uncle Saul and the answer may be posted here.

Last week’s question:
Dear Uncle Saul, How far should I go with developing my new business before seeking to raise venture capital?
- Brian

Go as far as you can! By bootstrapping your business during the early stages you will attain a far greater valuation enabling you to raise more money while giving less equity away. For more advice about VCs read "Brian Epstein is Not John Lennon, and Neither is Your VC."
- Uncle Saul


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What If?

By Uncle Saul | September 19, 2007

Did I ever tell you about the young Zoad
Who came to two sides in the fork in the road?
He looked one way then the other way, too.
So the Zoad had to make up his mind what to do.

If I go to place one, that place may be hot.
So how will I know if I like it or not?
On the other hand though, I’ll feel such a fool,
If I go to place two and find it’s too cool.

Play safe, cried the Zoad, I’m no dunce.
I’ll simply start off to both places at once.
And that’s how the Zoad who would not take a chance
Got no place at all with the split in his pants.

Dr Seuss – Excerpts from the poem The Zoad in the Road

Don’t Be a Zoad

Many would-be entrepreneurs struggle with the first step of the startup journey. In the hopes of mitigating their risk, they attempt to take multiple paths at the outset of their startup’s life. Starting off for two places at once is not playing it safe. Rather, this decision to not make a decision is a recipe for split pants and a failed venture.

As noted in The MBA Education And Other Oxymorons, launching a venture is similar to jumping off a cliff - without a parachute. A startup requires you to build your parachute while you are free falling. Once you make the jump, there is no turning back. The jump is tough enough to make under the best circumstance, it is even more difficult if you are surrounded by naysayers and well meaning relatives who cannot bear to see you fail.

The Entrepreneurial Shuffle

The next time you suffer a Zoadian moment of self-doubt, rent the movie Hollywood Shuffle. Irrespective of the particular fork in the entrepreneurial road that you are pondering, Hollywood Shuffle will help you see the startup world from its proper perspective. Not only will its humor help you through your emotional soul searching, its underlying message of pursuing your dreams in lieu of a near-term, steady paycheck will inspire you.

The making of Hollywood Shuffle is an entrepreneurial saga in its own right. Robert Townsend, who stars as a struggling African American actor who refuses to be cast in stereotypical roles, is also the film’s Co-writer (along with Keenen Ivory Wayans), Director and Producer.

On a paltry budget of $100,000, Townsend’s drive and vision resulted in a classic comedy that ultimately netted over $5M in gross proceeds. In absolute terms, this is a meager haul for a major, big-screen release. However, in relative terms, this percentage return on investment would arouse the interest of even the most jaded Venture Capitalist.

As a busy entrepreneur, you may not have time to watch the entire movie. No worries. Simply skip to Scene Nine, entitled “What If?”

In this scene, Townsend’s character, Bobby Taylor, stops by his Uncle Ray’s barbershop, just as his Uncle (played by David McKnight) is closing up for the night. Booby has just quit his job at the Winky Dinky hotdog stand. Throughout the film, he has been told by various well-intentioned people, “They are hiring at the Post Office”. Nearly everyone he encounters prior to this scene encourages him to relinquish his dream of becoming an actor.

I quit my job. I was working it for three years.

You should have quit three years ago. That job was just a waste of your time. (heavy sigh, dramatic pause)

You got to do it when you are young Bobbie. Before you fall in love and get a family. Cause if you don’t, time has a way of creeping up on you. Kicking you in your ass.

What if I’m not that good? What if I don’t make it?

What if you do make it? And what if you are that good? Bobby, you will never know until you try. You’ve to give it your all Bobby. You’ve got to give it everything you got.

I know. Cause it happened to me. I stopped believing in me. Started listening to all those other people telling me what I couldn’t do. I kept listening and listening. Until one day, I started believing it. And I quit. Lost my chops.

(Cue haunting soul music… Uncle Ray gets a faraway look in his eyes…)

Man. When I was singing, I was the happiest man alive. On stage, doing it.

(Kill music, back to reality)

Bobby, there ain’t nothing to it, but to do it.

Gotta believe in yourself Bobby. Don’t play yourself cheap. Don’t ever let anybody take away your dream.

Enter The Dream Killers

The decision of which fork in the road you should take is often complicated by the Dream Killers, which come in two distinct flavors.

Bitter Dream Killers are hapless souls which revel in destroying the dreams of others. Residing within the boring but safe confines of a Big Dumb Company or Soulless Government Entity, these corporate losers do / did not have the courage to pursue their own dreams. To assuage their self-contempt and guilt, they aggressively attempt to derail the dreams of others.

One Bitter Dream Killer stands out among the hundreds I have encountered, primary because of the extent of his vitriol. He was a senior member of Oracle’s Management Information Systems (MIS) group. We were discussing my company’s software solution that allowed users to gain remote access to their desktops without requiring them to involve their MIS personnel. Clearly the Bitter Dream Killer saw our innovative solution as a threat to his technological fiefdom.

He ranted on and on in a very animated and condescending tone regarding how, “no company will ever allow their employees to install your solution”. I listened patiently, thanked him for his insights and immediately made it a personal Jihad to close Oracle as a customer.

Rather than allowing his negativity to impair my attitude or confidence, my energy and resolve was renewed. His derisive tone motivated me to prove him wrong. It took nearly 18-months of hard work, but we eventually sold Oracle a seven-figure, multi-year software license. Although it was tempting, I did not follow-up with my brilliant Bitter Dream Killer and rub his face in his stupidity. Closing the deal and validating the efficacy of our technology was satisfaction enough.

Every successful entrepreneur encounters Bitter Dream Killers. As they spew their ill-informed negativity, just smile, channel their nay saying into a personal challenge and be sure to retain their contact information just in case you choose to later apprise them of your success.

Well-intentioned Dream Killers have altruistic motives. In order to protect the entrepreneur from the unpleasantries of failure, they attempt to dissuade to them from following their dreams. These well-meaning Dream Killers are often family members who cannot reconcile the child that they knew in her youth with the entrepreneurial adult who is now capable of pursuing their startup dreams.

This phenomenon is understandable. For a parent who changed countless diapers and cleaned up gallons of puke, it is difficult to realize that the former snotty-nosed kid is now an accomplished entrepreneur in the making. Even though their intentions are understandable, it can still be a formidable challenge for some entrepreneurs to reconcile their love and respect for the Well-intentioned Dream Killer and their desire to avoid a career at the Post Office.

An effective way to deal with Well-Meaning Dream Killers, is to follow Dr. Seuss’ advice; “Be who you are and say what you feel cause people who mind don’t matter, and people who matter don’t mind.”

Bank Robbers Unite

Karl Marx, bitter corporate weasels and loving relatives be damned. You have the means of production in your hands. There are no reasonable excuses for you to live your life as an ATM Operator, all the while secretly asking yourself, “What if?”

In David Kishner’s book, Masters of Doom, John Carmack, co-founder of id software and creator of the bestselling video games Doom and Quake, had the following to say regarding making the leap into an adVenture:

There Ain’t Nothing To It, But To Do It

Every entrepreneur faces the same challenge as Bobby in Hollywood Shuffle. Should they join The Herd and always wonder “What If?” or should they take a chance, pick a fork in the road and, in the words of Uncle Ray, “give it everything they’ve got”.

If you take Uncle Ray’s advice, no matter the outcome of your adVenture, you will never be haunted by the toughest of life’s questions, “What if?” nor will you have to suffer the Zoad’s indignity of splitting your pants.

Topics: Entrepreneur, The Fringe |

One Response to “What If?”

  1. David Schwartz Says:
    October 10th, 2007 at 1:59 pm

    As an additional comment to the part from Hollywood Shuffle- Out of all my friends (mostly around age 24), by far the most successful people I know are actors.

    I would have been an actor in an instant if I had any inclination to be on stage- I don’t however.

    My main reason for being (or wanting to be) an entrepreneur is that I want to be in a start-up environment, and I want to be able to make money based upon how hard I work. I like the start-up environment because I am a big fan of both creativity and multi-tasking.

    I think that being a broke college student has given me a strong motivation to succeed. My plan is to find opportunities that interest me and pursue them, wherever that takes me.