Talking to $1 Billion CEO’s

Posted on November 18, 2009. Filed under: Uncategorized |

Auren Hofmann (CEO of Rapleaf) wrote an interesting blog post recently about the common traits of “A-Players”.  Along with hard work, resourcefulness, rule-hating, punctuality, and a few others, Auren has observed that top level talent tends to be highly responsive.  He writes:

“Most A-Players get back to people quickly.  Usually within 24 hours. On the few occasions that I have emailed Steve Jobs, he’s gotten back to me in about 2 hours.”

While Hofmann was largely referring to speed of response, it has been my observation that frequency of response and willingness to engage are both directly correlated to level of success.  In other words, the most successful entrepreneurs and executives are the most likely to respond to cold calls, solicitations for advice and guidance, and even business propositions.  This is an extremely important piece of data for early stage entrepreneurs, as it is a bit counterintuitive.

Let’s take an example.  Jumpost is building a business around online classifieds in the real estate vertical.  There are probably 20 companies housing executives who could add outsized value to our efforts, whether in the form of unique domain expertise (advice), distribution (partnership), talent (recruiting), capital (investment), or credibility (mentorship).  The shortlist off the top of my head might be Craigslist, Ebay, Redfin, Kayak, Prosper,, Zillow, Facebook and Twitter.  I’m sure if I put a little more time into it, this list would change, but it’s relatively accurate.  As a very early stage startup (probably pre-product, definitely pre-scale), you are typically on the “need” side of any interaction you might have with executives at companies of this size.  You are not capable of delivering value to people at established companies before you at least partially turn your early vision into reality (whether reality means a product/service that will enhance their business, or a customer base that they are interested in reaching).  That said, I wrote in a previous post about the importance of learning from people who have achieved that which you aspire to, so what is an entrepreneur to do?

Intuition would say that the guys at the top of these companies have so many people calling on them with “needs” and not “gives,” that it is not worth trying.  So two options seem apparent: 1) move down the org chart at these companies, and see if you can get in front of the guy under the guy under the guy you really want to speak with, or 2) target less successful versions of the companies that you really want to connect with (so if the $1 Billion classifieds CEO seems inaccessible, maybe his counterpart at a $10M company will be easier to reach).  Both of these “networking” strategies are effective and should be implemented, but not before or in place of taking your shot at the “big dogs”.  I have found that the $1 Billion stars are more likely to respond and engage than are their $10M counterparts.  Why?  I don’t really know, to be honest.  I have hypothesized a few reasons:

1) The guys at the top have been around long enough that they have learned that networks are unpredictable.  Value mysteriously emerges from an executive’s network and even extended network in impossibly serendipitous ways.  Members attempting to enter an executive’s network may not present any immediate value, but for every piece of good will one builds, there is a decent chance it will yield fruit 1, 5, or 20 years later.  The fledgling entrepreneur in 2009, becomes Mark Zuckerberg in 2012.  Ambition and effort are strong postive indicators of future success, so if you have the balls to email Sergei Brin and ask for a meeting, there’s a good chance you are gonna make something of yourself down the line.

2) The guys at the top have nothing to prove.  There is a bizarre currency that exists between executives at all stages of business.  As human beings, we use a series of metrics to measure our success relative to our peers.  Compensation is one metric that many rely upon (I am making more than Jim, so I am successful), but the “company you keep” is definitely another.  Executives want to interact and associate themselves with professionals they perceive to be of a similar caliber or quality, and tend to avoid association with those they perceive to be less successful than themselves.  This phenomenon is largely influenced by a voice of insecurity, and frequently manifests itself in the mentality of “I’m too important to take calls, meetings, emails, etc…).  Granted, successful people are also extremely busy, so this is not always the case, but often the guys who still have something to prove take this tact.  Once you “arrive” and you are the CEO of Ebay, you don’t have anything to prove to anyone, and that’s when insecurity doesn’t influence accessibility.

3) Fundamentally “good guys” tend to get to the top more frequently then ass holes.  If you’re a good guy, sometimes you just make time for people when there is little to no value in it for you.  Call it charity, giving, volunteering, etc…if you’re in a position to help, and your a “good” guy, more often than not you do.

Whatever the reason, or combination of reasons, my advice to entrepreneurs is “don’t be shy.”  This is not to say you should go out and spam John Donahoe at Ebay (who by the way, is an example of someone who is responsive, albeit hard to reach), when you have an idea for a new online marketplace.  It is critical to be responsible with this strategy.  Create a context that is extremely thoughtful, and explain exactly why the person you are trying to reach is uniquely capable of providing the value you seek, AND…be extremely respectful of the that person’s time and accomplishments.

Lastly, if you do decide to call on the type of people I’m talking about, you damn well better give back as much as you take.  Someday, whether presently, or in the future, there will be a class of people who are in “need” of your attention.  When those people present themselves, and ask for your value, do everything you can to be accessible and give.  It’s sort of a goes around, comes around kind of thing…and who knows…maybe there is even a causal relationship between giving and becoming a “top dog.”

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4 Responses to “Talking to $1 Billion CEO’s”

RSS Feed for Jordan Cooper's Blog: startups, venture capital, etc… Comments RSS Feed

Couldn’t agree more. A year spent interviewing CEOs lead me to the same conclusion: successful people are surprisingly accessible. Here are a couple more stories and 4 more reasons why:

BTW. Random that you mentioned Auren at the same time i sent you that link!

hmmm. extremely similar post…6 months prior…I can’t tell if I read this and subconsciously plagiarized…or if I made this point to you and contributed to your original post…regardless, glad we are on the same page 🙂

it’s hard for me to get back to everyone in 24 hours. but it sure is a goal

Good post and good advice. I highly recommend reaching out to CEO’s of big companies, but only if you have a solid plan in place for the conversation and you keep it interesting. Purely pitching your wares is not going to get much of a response, but asking for genuine advice or feedback is something that elicits interest. Generally, my response rate has been about 15%, which is much better than the response rates on typical cold calling initiatives. So when someone tells me they cannot reach the CEO of such and such company, I tell them to stop being a wuss and just call. There is nothing to lose in that scenario, but a ton of upside if you connect.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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