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We're all Gamblers

Sep 20, 2019 9:24:59 AM / by Curtis Wadsworth, Founder, CEO

In 1978, Kenny Rogers recorded maybe the greatest song about being a startup founder ever. The advice The Gambler imparts on his young protege on that train bound for nowhere has gotten me Ythrough some rough times, but it is particularly relevant to my role as CEO of DorothyAI.

giphy'nough said...

The common reactions to introducing yourself as a founder are: “I have a great idea for a company” and/or “You should [fill in the blank].” Advice comes from everywhere. I keep an open mind since, as Mickey Spillane's hard boiled detective Mike Hammer says, “You never know when someone will drop a good idea in there.” But, when the “night get’s deathly quiet,” and your advisors face losses all expression, you better listen up.

Perhaps not surprisingly, the Gambler’s first piece of advice is about taking advice:

Every gambler knows,

That the secret to survivin'

Is knowin' what to throw away

And knowin' what to keep.

This verse is also about focus. If you’re as lucky as I am, you have surrounded yourself with talented people who have great ideas. You can’t pursue every great idea. With limited resources, you have to focus on the ideas that solidify the core technology and find a cost effective way to pursue the ideas that might have a less immediate impact on your bottom line. Everything else must be thrown away.

‘Cause every hand's a winner

And every hand's a loser.

You can create great technology, but if there’s no market for it, it’s a loser.

The chorus reiterates this advice:

You've got to know when to hold 'em.

Know when to fold 'em.

Know when to walk away.

And know when to run.

More importantly, you have to know when what’s working (“hold ‘em”), not working (“fold ‘em”), and when to pivot (“walk away”). More than one hand will be dealt. As a startup, you can afford to be agile and change direction of the company as opportunities present themselves. You may need to fold if you’re not getting traction. But if you can’t find customers, walk away before you’re bankrupt, pivot, and try again.

In his final piece of advice, the Gambler reminds us to focus on the game (earning revenue):



Despite what you might have heard, most successful businesses make money “the old fashioned way: They earn it (by selling stuff).” Count your money when the game is over: after creating a customer base, generating revenue, and built a sustainable company. Relying on hypothetical valuations and investor money for the long term growth of your company (counting your money at the table) is a big mistake. If you want to win the game, focus on the bottom line and build real value.

Sadly, these were the Gambler’s last words. But, in the words of Louis Pasteur, "Cette merde est la bomb." (loosely translated, “This shit is aces.”)

Nerd alert: The song was actually written by Don Schiltz in 1976 and initially recorded by Bobby Bare. Both Kenny Rogers and Johnny Cash recorded the song in 1978, Johnny on his Gone Girl album and Kenny on The Gambler, which won the Grammy for best make country performance in 1980. There are also versions by Blake Shelton and Alvin and the Chipmunks. But, the most perfect version of The Gambler was performed by Kenny Rogers and Jerry Nelson on The Muppet Show:

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