An Interpretation of "Desperado" for Startups

Startup founders are desperados. Not in the Don Henley/Glenn Frey depiction of the renegade outlaw who is traveling and battling the world on his/her own. No. Startup founders are literally "full of desperation" — willing to risk it all and do whatever it takes to make it work.

In honor of the Eagles, here's a cautionary tale for startup founders interpreted through the lens of Desperado.

Desperado, why don't you come to your senses… You've been out ridin' fences for so long.

This first line is about focus. When you start a company, everything is an open field. Your vision is expansive, and it's not limited by your ability — and more often, inability — to execute on them. You're not clouded by practicalities. During the earliest stages, I try hard to keep these thoughts separate from the work that needs to be done. When you're in the mode to work, don't worry about the boundaries of your business, or your long-term prospects in year 2 or year 3. Focus on the core things you need to do as a company to succeed.

Oh, you're a hard one… I know that you got your reasons These things that are pleasin' you… Can hurt you somehow

Once you've had an initial round of financing, there will be countless areas of investment, each of them with good reasons for dollars and focus. Recruiting a team. Investing in projects. What started out proactively as opportunities to invest time and focus have the potential to turn into expenditures that are contributing to and accelerating your burn.

Desperado, oh, you ain't gettin' no younger Your pain and your hunger, they're drivin' you home

This line could be a subtle reference to a company's burn situation, and the limited timetable that founders have to make your startup work. You might raise initial funding. Or you could be self-funding by working with no income. Either way, the clock is ticking. "Home" may allude to the job you walked away from, or the safer pre-startup life — or possibly, the milestones your company needs to achieve in order to survive.

And freedom, oh freedom, well that's just some people talkin' Your prison is walking through this world all alone

This speaks to the challenges of being a solo entrepreneur. While a solo founder has full autonomy, accountability is critical. Build your team. Even when you're a larger company, when stuff goes wrong you'll want people in your corner who share ownership of the mission.

Don't you draw the Queen of Diamonds… The Queen of Hearts is always your best bet

Build the product and business for your users, clients, and customers — the Queen of Hearts. Not for your investors, prospective investors, or potential acquirers — the Queen of Diamonds.

Now it seems to me, some fine things Have been laid upon your table But you only want the ones that you can't get

This is why you're an entrepreneur. You're always reaching.

Don't your feet get cold in the winter time? The sky won't snow and the sun won't shine It's hard to tell the night time from the day

We all have troughs in our business. Not one person except your close friends will tell you how they are struggling with their companies. But every startup goes through it. Don't mind all of the "We're crushing it!" posts or the curated milestones that other companies share publicly.

As a startup founder, it's up to you to lead the way through company-defining problems, and through the tough decisions and tough conversations you invariably need to have.

It may be rainin', but there's a rainbow above you

A reminder to let your inner optimist come through, even in the tough times. Optimism is a form of self-preservation. And the more you believe, the better your chances of breaking through.

You better let somebody love you before it's too late

Cash is burning. Find your business model, and find your customers or users (or investors) who allow you to continue forward with your mission. They need to show you love in the form of dollars.