2 Ponies, Minimum

I’ve taken on a new role: options oracle.  I’m getting more and more letters like this one, seeking advice:

Dear George,

I’m totally bored with my job. It’s safe. I make an OK salary. My bosses love me, and I have no big performance pressures. Work is uncomfortably comfortable.
My dream is to grow my app-development business. It generates revenue.  It has proven its validity. I love it. But it’s still a startup with no long-term performance history.

My divorce (my one and only, trust me) at age 56 reduced me to financial rubble. I have a lot of fiscal recovery to do, and I don’t know how long that will take.  Is it prudent to be 100% vested in a startup versus landing a more challenging, better paying full-time job, and using some of my salary hike to hire a sales & marketing person to grow the startup?

At the moment I have 1.5 income-stream ponies on the track. What are my odds of winning?

Confused In Chicago

Dear Confused,

I think you’re being smart by looking into ways to hedge your bet.
This is what you have going for you:

• You’re not staking your entire financial future on an unsure payoff.
• You’re not waiting until you are in your 60s to begin developing a second revenue stream.
• You understand the risk/reward calculus, and know that some sort of sacrifice is a prerequisite for the next step.

In my opinion, you actually have three choices, not two.  Run the financials for each. You could:

• Stay where you are for as long as you can until your own business generates enough revenue to pay you a sustainable salary.  Think of boredom at work as an interest-free way to finance your startup.
• Go to a much higher paying job and hire someone else to sell, knowing that a new job will sap some of your energy and introduce uncertainty.
• Get enough financing to work in your startup full-time and hire one great salesperson to help the business grow. Be aware that while banks will care about your divorce because of its impact on your personal finances, investors may not.

Of course it’s up to you, but I think it isn’t a question of having 1.5 ponies indefinitely.  I think it’s a question of the smartest way to have two.

Best of luck,
George

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