On Not Cashing Out

I just read Ryan Carson’s Selling Your Company Doesn’t Make You Happy and it reminded me of Phil Libin’s philosophy on running a startup. When I first read Phil’s thoughts on running a 100 year company it was a refreshing and unexpected change of pace from the usual “build a company and cash out” modi operandi that seems to be the standard in the startup world.

(I wonder if Zuckerberg has the same intention with Facebook. If he still sees himself running it 20 years from now.)

It’s an interesting perspective to consider – a curious question to ask…

What could I be happy doing for the rest of my life?

And is there even a single project that could encapsulate my real desires and be a source of fulfillment for the remainder of my days?

I look at Phil’s mantra (which I sum up as “I’m gonna be doing this for the rest of my life”). There’s gotta be something freeing about a commitment like that. I used to view commitment and freedom as opposites on a continuum. However, maybe there’s even greater freedom when you’re bounded by a commitment of this magnitude. I experienced this first hand when I asked Ashley to marry me.

So applying that to “what could I see myself doing for the rest of my life” is a curious mental exercise, even if I don’t answer it (yet).

I met Ryan Carson in San Francisco in 2006 (Future of Web Apps) and have always admired his ability to build a great team – he surrounded himself with great people and it really showed throughout the event. I met Phil Libin in a restaurant at the Wynn in Las Vegas, commenting on his Evernote shirt, before I even knew who he was. Both of these guys are cool cats. There’s a peace about them – a cool, calm demeanor – and their heart is in the right place – which you can feel. It comes across.

Enjoying the Game

I cashed out of my company last year. It was a relationship I stayed in for too long. It was surprisingly a lot like breaking up in a romantic relationship, with similar amounts of drama. I recently placed myself in a position again where I’m hungry, driven (with my financial and emotional future at stake – to make it interesting).

I’m now playing a game of “let’s go get it” and loving the process. I, like Ryan, learned that despite the assumed popular opinion, that it’s not really about the money. It’s not about creating something, selling it, and making your life passive. Well, it could be – but that looks too much like fools gold.

To that end, I’ll leave you with Ryan word’s:

Enjoy the adventure that you’re currently experiencing and realize the daily highs and lows are what actually make your life meaningful.

photo credit: carolyntiry via photo pin cc

Posted 12 years ago on 09 August 2012

About Parker

Parker Benjamin is the owner of DMAD and has been writing for the web for over 10 years. He is passionate about design, Wordpress, travel, language learning, fine dining, and online marketing. Note: Some links on this site are monetized by affiliate programs - see disclosure for more details.

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