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27 Extraordinary Adventures and the ONE that Dwarfs Them All

Stefan Loble

Sailing across the Atlantic


A little ways back - in a moment where running Bluffworks felt particularly hard - I scribbled down a short list of some of the adventures I've taken on during my life.

Before starting Bluffworks I had:

  1.   Sailed across the Atlantic.
  2.   Walked barefoot for weeks alone in the jungle of Irian Jaya.
  3.   Narrowly dodged getting nabbed by some nasty guys in Eastern Turkey.
  4.   Hopped a freight train down the Columbia River Gorge.
  5.   Married a girl who had a dog that bit me.
  6.   Ran naked in front of Nike Town wearing only a pair of Nikes.
  7.   Convinced Barbara Corcoran to launch my Kickstarter project.
  8.   Worked so hard, I kept a sleeping bag under my desk.
  9.   Let spell check miss-correct "warehouse" into "whorehouse" in client-facing documentation.
  10.   Messed up a software configuration that caused a whole team of programmers to chase their tails for a day.
  11.   Cried at work.
  12.   Fathered a son whose energy eclipses mine.
  13.   Wrote software overseas for $4 an hour.
  14.   Stomped grapes all night for a ride out of wine country.
  15.   Went on business trips where I shared a bed with my boss.
  16.   Went on business trips where I shared a bed with bed bugs.
  17.   Sat in first class without a ticket.
  18.   Shoveled piles of cookies on the Oreo production line.
  19.   Bought a black market video camera that turned out to be wet newspaper.
  20.   Had my camera stolen right out of my pocket in Morocco.
  21.   Dated a woman twice my age.
  22.   Convinced my father-in-law I'm not a bad guy.
  23.   Cheated on an exam to become nationally ranked in Latin.
  24.   Knocked-out a bully with one punch.
  25.   Learned to survive speaking only Vietnamese.
  26.   Crashed a car driving the wrong way down a one way street.
  27.   Went head to head in corporate politics and lost.

I wrote this list as I thought to myself, "If I've done all of these grand things, than why is entrepreneurship so damn hard?"


In my view, the answer is chiefly related to the fact that making a company go requires a founder to be good at so many things. You can't just play to your strengths. As challenge mounts, it can feel like a mirror is held up against your capabilities. And, no one is good at everything.

How hard was it?

I feel a little sheepish revealing that it's been tougher then anything I've ever taken on. That's the point of the above list. And also that, I had no idea what I was getting into by starting a company like Bluffworks. This years longer journey has been harder than them all. Sometimes people ask me...

Can I do it?

Absolutely. With any luck, you'll avoid some of the missteps I've made. Doing it by becoming an entrepreneur at over 40 is harder than when you're young. But, it's possible. You just have to face the mirror that calls you to account for the weaknesses you were dealt alongside your strengths.

I wish you Godspeed.

Stefan Loble



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