9 Blunders of VCs Turned Entrepreneur

Nov 17, 2009 · 6 mins read
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Our guest blogger, Larry Chiang, is an instructive humorist and blogs at Business Week. If you liked “10 Things They Don’t Teach You at Business School“, How to Work a Cocktail Party and “10 VC Mistakes,” you’ll like this submission on some all-important mistakes VCs make when they become entrepreneurs themselves.

By Larry Chiang

Jumping from venture-capitalist-board-member to “start-up founder and CEO’ is near impossible for the HBSer / GSBer to successfully do. The b-school molded HBS-Harvard Business School / Stanford Graduate School Business (GSB) need to navigate eight pitfalls.

-1- Too self indulgent.

Being smarter than a billionaire you met during b-school show-and-tell, does not make you a better entrepreneur. This fundamental fact sinks many want-preneurs.

Stop the ego massaging and set aside all 170 IQ points and dumb it down. Robert Downey Jr recommends going, “partial retard” in his character from Tropic Thunder.

Look at the biggest hits:

“eBay” – pretty retarded selling beanie babies and Pez dispensers in the 90s

“Yahoo” – a dumb but cute-funny, pre-orgasmic sound upon discovering a search result on a Stanford server with the same name.

“Google” – please. The site (and campus) still looks like romper room time with Barney. No not that one…


“Duck9″ – are you effen kidding? The whole site is a logo with a dumb riddle.

-2- Too focused on perfect formula vs market pain.

What do you call a mish-mash or under experienced payment executives doing peer-to-peer payments? The payPal founding team.

You can bet, the PayPal mafia (since their $1.5B exit) focuses on market pain.

-3- Too cerebral.

They do not pay you to be smart. They do not pay you for researching a silver bullet technology. They pay you to promote. They pay you to raise the $0.02/share stock price by promoting adoption of your

Another trapping of too cerebral-palsyness is knowing too much about too many things. Entrepreneurs hone in like a laser beam. Heck most entrepreneurs do not even know what a credit FICO score is or a credit crisis or have talking points on the impending Obama Presidency [insert pic here]

VCs read coverage and this rss habit needs to be KICKED when you put the CEO hat on.

-4- Too unproductive.

Why are VCs turned entrepreneur lame-duck?! Maybe it is the ex VC’s pedigreed family. Maybe it is the blue blood family money… Maybe criticizing and producing are too different from each other. Maybe consulting and executing are too different from each other.

Also, meetings taken by VCs for your new upstart can not be logged as productivity. Those charity meetings are taken as a hedge because they think you will fail and be a VC again.

Fire the wife. Fire the girlfriend. Your new wife and your new mistress have a new name… and it is called D-u-c-k-9. Or Asse9. Or Buck9. Or elephant9 if you are stealing my URL (yes “Elephant9″ is
registered to a Sand Hill Road squatter).

-5- Too talentless.

Academic talent does not usually translate into entrepreneurial talent — some would argue academic talent NEVER translates into entrepreneurial talent, but then they’ve never met Tom Chiang (dad).

SOLUTION. Re-gear, retool and start sandbagging for success. I mention sand-bagging because it is defined as deliberately misleading someone to think you NEVER did b-school. You can not ramp up entrepreneurial talent while clutching your tier one MBA status.

-6- Too inflexible.

Welcome to beta male-ness. You were an alpha (sort of) back when you were quoting the size of Fund XIX. Live, embrace AND WALLOW in your new tier two status.

Mr. Ex-VC, want an exercise in ego flexibility? Hand out slices of pizza at the next blogger meet-up that WordPress produces. Kiss blogger ass (or Asse9) right near the butt crack.

SOLUTION: sell your condo and go “native”. I own three homes but live in a dorm room on University Avenue… Eff you, because this advice is falling on deaf ears.

-7- Too non promotional.

Sell it. Rarely does something sell itself. I can not repeat this point enough.

Sell it don’t smell it

“The key to sales is to get them to sign on the line which is dotted,” Alec Baldwin in Glengarry Glen Ross.

-8- Too historical.

Majors from the last war that are now Generals historically fight to re-win lost battles. B-school does something similar to us when we pour over HBS (Harvard Business School) case studies.

So you are damned if you know case studies, and you’re damned if you don’t. But the biggest factor VCs have in not making the jump to entrepreneur is…

-9- Too unable to weather a storm.

Entrepreneurship is 90% crap so weathering a first storm motivates most exVCs into “cutting their losses”. Get ready for a future storm with my litmus test…

Can you handle a mutiny?
Can you ramp up while 70% of your staff is severed?
Can you buy your assets back in BK court and restart?
Does the thought of that make you cringe?
Can you sell your way out of a wet paper bag?
Can you charm you suppliers and vendors for 2-10 net 90 terms after you
signed docs for net 30?
Can you negotiate your debts with collectors minutes before you go on a
Tony Perkins panel?

Most entrepreneurs wither-and-wilt during the third storm they face. The over-under on the number of “storms” a VC HBSer can handle: 1.3. Smart money bets the under. TRANSLATION. An over under but is when the “house” calls out a prediction that is eerily spot on. You place your “bet” and pick ‘over’ or ‘under’. Easy, weasy, Chin-easy. Gawd I just made that up.

The one hit wonder has an over under number of 1.8. Being more fragile than a one-hot wonder is NOT a good position to be in.

Stay tuned. When I cover (err crash) the SAG Awards and Oscars, I’ll cover the four mistakes of actors turned directors.

My focus is, “What They Don’t Teach You At Stanford Business School” and I have a book coming out 09-09-09. The next conference I am going to is Tony Perkins VC Conference

Larry Chiang is the founder of duck9, which educates college students on how to establish and maintain a FICO score over 750. He is a frequent contributor to GigaOm’s Found Read. His earlier posts include: How to Work The Room; 8 Tips On How to Get Mentored ; and 9 VCs You’re Gonna Want To Avoid. You can read more equally funny, founder-focused-lessons on Larry’s Amazon blog.