The Apprentice – Entrepreneur Version

We are all apprentices in a craft where no one ever becomes a master
Ernest Hemingway

Silicon Valley is built on simple myths – one of the most pervasive is that all winning startups are founded straight out of school by 20 year olds from Stanford or Harvard. The reality is these are the exceptions not the rule.

Too Old at 30?
I was having coffee with an ex-student at the ranch, watching our bobcat hunt in the front lawn. This student had called and said he had to meet  – “I’m having a career crisis,” was how he described it. I invited him to make the drive down.

As the story unfolded, it turned out that he just turned 30 and realized that he hadn’t founded a company yet. “Everyone now starts a company out of school. All my classmates who were interested in entrepreneurship have started their own companies. I’ve just been working my way up the ladder.” He explained that he had a progressively set of better jobs at companies that were in the “build” phase. These ex-startups had found a repeatable business model and were putting the processes in place to grow into a large company. They had hired operating executives and were starting to scale.

“Well what’s wrong with what you’ve been doing?” I asked. “Oh, I’ve learned a ton,” he replied. “If I had started a company out of school I would have made all kind of stupid mistakes.”

Ok I wondered, the problem is what? “So how have your friends done?” We watched as the bobcat patiently stalked a gopher. “Hmm” he said,  “A few did ok, but most of them cratered their startups. For the amount of money they made most of them would have been better off working at Walmart.”

Slow Learner
I told him he wasn’t alone. Early in my career I apprenticed at companies that had recently been startups, hadn’t yet gone public and were still innovative. My career was a slow 20-year progression from training instructor to product marketing manager to VP of Marketing. It wasn’t until my 7th startup that I was a CEO in a startup I co-founded (and its failure left a crater so deep it had it’s own Iridium layer.)

Perhaps the most important part of this non-metoric career trajectory was the mentoring I received. I managed to work for, with, and around people who were truly skilled at what they did. Some of them consciously taught and shared their skills. For others I tried my best to suck out every bit of what they knew and emulate the best of their skills. (At times the learning was painful, but it was never forgotten.)

While the Silicon Valley myth is that all winning startups are founded straight out of school it’s just not true.

No Longer a Startup
In raw numbers, most engineers and MBA’s aren’t founding companies, they’re going to work for others who have; Facebook, Google, Zynga, Four Square, Twitter, etc. While the jobs at these companies are still incredibly challenging, and passion and innovation may still pervade their company cultures, the startup risk (“will we run out of money before we find our customers?”) is gone. As great as these companies may be, they are no longer startups. (A startup is a temporary organization searching for a repeatable and scalable business model.)

But employees in these ex-startups are getting the best hands-on education for entrepreneurship there is – as apprentices.

As we watched the bobcat make a meal out of the gopher I offered that his career was proceeding just fine. Someday, he’ll hear a calling, pull his head out of his computer, look around and say, “I can do this myself.”

And the cycle of creative destruction will begin anew.

Lessons Learned

  • Not all startups are founded by 20-somthings straight out of college
  • Working for companies that were recently startups is a great way to apprentice
  • These companies can you give a lifetime of mentorship hard to achieve in other ways
  • When you’re ready you’ll hear a calling, and it won’t be a job

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9 Responses

  1. I’m 58 and at the helm of a startup that is going bigger than I imagined. OK it’s not Facebook but we’ll do very well.

    I’ve done startups, and I’ve put in the years at Microsoft. And lots of other things along the way.

    The oldest person on my team of ~25 is 32 and refers to the rest as “The Kids”. Youth is critical.

    In your recent video you talk about how “failure aka experience”. I have experience, with a high tolerance for risk. And I can be at this point my own Angel investor – no one is distracting me.

    This is my calling and for the first time, in a long time, it doesn’t feel like a job. It’s hard to explain but the experience, OK the age, gives a clarity to the calling. I don’t need to be known, I don’t need to speak at SXSW. I just need to relentlessly execute on the calling. The experience has enabled me to understand how to do this.

    Looking forward to the exit, so I can do this all over again at least one more time.

  2. You mean I didn’t have to do this right out of school?! Now you tell me. 😉

    Great post, Steve, and great bobcat shots.

  3. Steve – I just came across your blog two days ago. I’m the one in your Google analytics that has a zero bounce rate and is skewing the avg. time on your site. I’ve been on for 48+ hours straight, with about 10 different windows open for various blog posts.

    I started a non-profit that mentors women for three months (free) in starting their own businesses. I’m already implementing your Lean LaunchPad model for one woman as a test case. I’m buying your book today – I already bought Business Model Generation. I’ve been dissecting your posts piecing it all together.

    As a serial entrepreneur myself, I have the deepest appreciation for all the wisdom you share here. I have an almost neurotic need to constantly improve the the business startup process for the women I help, and your methodology is filling an enormous gap.

    I’m giving you credit all over the place in the work I’m implementing. If there is something more you would like me to do, please don’t hesitate to ask.

    Thank you for teaching us all how it should be done!

  4. I appreciate what’s mention in the lesson learn. This is actually the truth when I persuade my career.

  5. Steve, this is very encouraging. It gave me a moral boost after my birthday blues (now about a decade older than your friend). It has been two years since the customer development class and I am still steering what you called “a backward wheel”

  6. Steve that is exactly the kind of post that was missing through all the dust that’s up right now with the startup community!

    Thank you for writing such an insightful and inspiring post 🙂

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