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From Hopes and Dreams to The Real Thing


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I’ve lived the ups and downs and downs and ups of entrepreneurship and my experience has been that when you look back on those days when you were in the trenches fighting for survival, you’ll see them, through the lens of nostalgia, as the “good old days”. By contrast, scaling a fast growing startup that has found its market fit is stimulating and exciting but, at least for me, sits nowhere near as prominently in my minds list of proud moments.

My last entrepreneurial run went from 2000 to mid 2006 with a true “go to the light” near death experience throughout most of 2002. The business ultimately found its market fit and had a high growth phase from 2003 to 2005 (from 7 people to more than 200 during that time). Through the miracle of memory, I now remember 2002 very fondly as a source of pride, learning, and character building. But at the time it was not fun – on the contrary, it was as scary as I would let it be.

I’ve been watching and reading about startups since I was in high school and knew it would be what I tried to do when I read Startup by Jerry Kaplan while in college (still a great book for entrepreneurs). I’ve observed again and again that for every rapid success like Facebook, there are 100s of overnight moderate successes that took 10+ years and will never make it to the business papers and blogs. It’s really a marathon, not a sprint and sometimes your worst enemy is your own psychology or the psychology of the naysayers who inevitably crawl out of the woodwork. After all, it’s easy to be a critic and when things don’t follow a perfectly straight curve to success, if you allow yourself to, you’ll hear plenty of them.

On the hard days, I sometimes look to Parson’s rules of life:… They are all great but number 2 and number 3 are, to me, the things that ring true on all too many days of the entrepreneurial endeavor.

2. Never give up. Almost nothing works the first time it’s attempted. Just because what you’re doing does not seem to be working, doesn’t mean it won’t work. It just means that it might not work the way you’re doing it. If it was easy, everyone would be doing it, and you wouldn’t have an opportunity.

3. When you’re ready to quit, you’re closer than you think. There’s an old Chinese saying that I just love, and I believe it is so true. It goes like this: “The temptation to quit will be greatest just before you are about to succeed.”

And the last comment – startups are uncertain until they are not and when they stop being uncertain, they are no longer really startups. If you sign up for being an entrepreneur or working in startups, that’s what you are signing up for. On the particularly hard days I ask myself whether there is anywhere I’d rather work (or anything I’d rather be doing including sitting on a beach) even if it meant more money or less uncertainty. And on those days I realize that I really do have the best “job” in the world.

Two thoughts from my father to close the comment, the first of which he told me when I was a teen: “There will always be someone smarter, richer, more accomplished, or better looking so to find satisfaction and meaning, you’ll have to look within”. Nothing truer could be said about entrepreneurship. I’ve never had a huge homerun – the kind of thing that gets you into the business press. But I don’t value my contribution to innovation and creation any less than the names and stories I read about in the press. All entrepreneurs – large and small – push the ball that is society and humanity just a bit forward. Larry and Sergei are the ones we read about in the press but their insights – large as they were – were built on the shoulders of countless unnamed others who are mainly not rich and certainly not famous. Entrepreneurship and innovation is a “noble profession” (borrowed from Randy Komisar’s recent comments… ) for all of the people who are involved in it – those with their names in lights and those who grind away anonymously. Society and humanity benefits very little – or not at all – from the untold numbers of rich people who became truly rich by hacking the financial system (to quote Mark Cuban) – and benefits massively from the countless numbers who – despite stress and lack of financial reward – devoted their working lives to innovation. The failures matter by the way. The iPhone for which Steve Jobs gets credit was built on the backs of countless other handheld computers that were before their time and whose investors and employees “failed”.

And closing with a joke from my dad “what’s experience?” “It’s what you get when you don’t get anything else”


Reposting this brilliant comment by Elie Seidman on Fred Wilson’s blog. I can’t say I’ve really been able to cross the chasm so to speak yet. That’s a really hard thing to do, and I have increasingly more respect for those who have. The truth is more entrepreneurs don’t make the leap from hopes and dreams to the real thing. Entrepreneurship is difficult.

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