I went to Y Combinator’s Startup School on Saturday (that’s YC-founder Paul Graham, in case you don’t know) even though most people in Silicon Valley see the material there as “too basic.” My goal is to perpetually learn and apply and to learn as much from the audience as from the killer line-up of speakers Y Combinator recruited.

What I learned I posted to Twitter. My notes are in my facebook album.

Anyway, these are The 9 YC-Types that I met that day — and a fewof the things you can learn from them:

1. Mr. Never Woken Up Before Noon. Codes and compiles well into the early morning. Only wakes up at 9AM for killer content. Fresh in from Europe. Is full of wonderment that 12 zip codes in Northern California contain 90% of venture money. Doesn’t know about the 9 VCs you’ll want to avoid meeting, but gosh darn they have great accents.

2. Mr. Silver Bullet Detector. A.K.A, a VC. Wants to find the next Google, Myspace, Yahoo!,

and get his carry (you-know-what) popped with the this 3rd fund.

3. Mr. DDSS Founder Presenting. DDSS stands for Dumb-Down-Sandbag-for-Success. During AM presentation said stuff like, “money matters with how many people you hire. The more money you have the more you can hire.” No where near as dumb as the things he says — even though he pretends he didn’t present during lunch. Continue »

I’m a repeat founder and YCombinator groupie. I’m the wrong age group to apply to YCombinator, but I’ve still learned a lot from the incubator from afar — like, the virtues of micro-loans and “entre-sumers.” This is my story.

More than a decade ago, for my first startup, I was fortunate to have found a successful but semi-retired former VC as a Board member and a mentor. As I learned more about his background, I discovered that my low-key friend was actually quite famous and had made seed investments in Sun Microsystems and a few other pioneer semiconductor and networking companies in the late-70’s to late-80’s.

One day I asked him how he managed to find these choice companies, almost all of which had become the pillars of Silicon Valley. He smiled and said, “We were lucky”.

I believed him. Many successful entrepreneurs and investors were successful because they were at the right place at the right time. It helps too that when the right opportunity presented itself, they also had the right skills, right experience, right circle of acquaintances and the right financial resources.

So I constantly ask myself, “What made him so lucky in the past?”

And more importantly, “Would I ever be so lucky in the future?” Continue »

I don’t think of myself as a serial entrepreneur since the terminology is most commonly used to describe someone who has had multiple successes (which I haven’t). But I also cannot pretend to be a first-timer — without having to explain the tread marks on my forehead.

So I am a hybrid. As such, I do have a few lessons that I can share which I have been writing up as a book, entitled “Survival Guide for Bootstrapping Entrepreneurs”. I have finished five of the planned ten chapters and I have posted them online on my blog, StartupForLess.org.

10. Why Startups Fail and Why Gigamon Should’ve Too

9. How to Turn Your VC into Your Worst Enemy

8. What I Learned From My Dad Who Taught Me How To Ride A Bicycle

7. Make Money Then Make Meaning

6. Team Building versus Bread Making

Given that Tuesday was the deadline for applying YCombinator summer funding, I imagine right now there must be at least a few hundred aspiring entrepreneurs (founders and cofounders) waiting to jump in with both feet. At the risk of being presumptuous, I’ve distilled my lessons-learned into the following three points and offer them to the contestants of the YC contest with my best wishes.

Remember: There are no losers in entrepreneurship except those who stop trying.