Archive for July, 2010

When The Dragons Emerge

Posted on July 16, 2010. Filed under: Uncategorized |

I feel like partnering with an investor is a bit like searching for your dragon in the film Avatar.  There are many dragons out there, all of which are capable of connecting to your strange hair braid or whatever that thing is, but there is only 1 dragon that perfectly complements you.  You have to approach a bunch of dragons, look them in the eye, most will turn away, but one will get a crazy look in their eye and decide that they want to tangle.  At that point, you need to fight them for a while, deflect their various attacks and attempts to kill you dead (they are just testing you), and then, if you survive the tussle, and earn their respect, you’ve learned how each other operate, and you can form a bond.  That bond is a partnership.  From that point forward, you communicate without effort, and fly or fight through your market as a team.

One of the most important things to look for in finding your dragon is a common language.  You need to find investors who can process your thoughts in the language that you think in.  If all of your ideas, learnings, and plans need to be translated into a different language that your investor thinks in, you are not going to benefit from the full brilliance or value of that investor.  Something will be lost in translation, and re-translation when they guide you in their framework and you need to input their guidance back into your own.  Frictionless information flow between you and your investors (or advisors for that matter) is key to maximizing such a relationship.

If you are building a syndicate of investors, not every member of the syndicate needs to have this frictionless transmittance.  Different investors can offer you help in various facets of your business, but your key investor, or the guy/girl who sits on your board, or maybe a non-board member but your closest strategic confidant, must be someone who speaks and thinks in the same language as you.

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It Takes Confidence to Become King, but Humility to Stay King

Posted on July 11, 2010. Filed under: Uncategorized |

I was talking to a very close friend yesterday who was pretty down, having fallen short of his own professional expectations of himself.  He is an extremely high achieving guy, years ahead of himself in the professional realm, and like many folks in our world, he expects to crush any challenge in his path.  After 4 or 5 months trying to turn a business around, the numbers aren’t what he hoped, and we talked about how to deal with professional disappointment.

Dealing with disappointment and executing both personally and professionally through it, is one of the few skills that I don’t think you can shortcut at a young age.  For the most part, I like to believe that a brilliant 25 year old is capable of performing at the level of a less brilliant 35 year old, but there are some parts of business that require an emotional maturity that may only come with experience and time.

Specifically related to disappointment, what I’m starting to realize is that it is IMPOSSIBLE to never fuck up or fall short.  If you don’t experience any disappointment in your professional pursuits, you are playing it way to safe.

The first time or two that you disappoint with a lot on the line, it feels like the end of the world.  In fact, sometimes the consequences can be quite serious.  Jobs are lost, money is lost, respect is lost, and without the benefit of 10 or 20 years seeing a healthy sample size of disappointments and how they pan out, those consequences are extremely hard to work through.  As I approach the 6th year of my professional life, I think I am getting a little better at dealing with disappointment.  My guess is when I’m 40 I will know exactly how to deal with it.

Disappointment is a part of life, no matter how good you are or how good you will become.  We do our best to prevent it, and hopefully we achieve more than we disappoint, but with disappointment we also develop humility.  It is this humility that allows us not to be shocked by future disappointment.  Without shock, we become better at executing through the bad, and toward achievement.  I’d be interested to hear from older guys/girls, but my sense is great operators learn over the course of their careers how to address disappointment effectively.

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Thoughts on classifieds, Craigslist and local

Posted on July 6, 2010. Filed under: Uncategorized |

For no particular reason, I’ve been thinking about a question.  If you wanted to become the next Craigslist, build a better matching mechanism between local supply and demand, and present local sellers, whether they be individuals, or independent service providers, with a better vehicle for finding buyers, what would you do?

1)  You wouldn’t try to take down Craigslist out of the gate.  Craigslist doesn’t topple in 12 months, craigslist slowly dies over 10 years.  As long as they represent a high volume of local consumers, they will attract local suppliers.

2)  You would build your UX under the assumption that your users will touch both your product and Craigslist in the same search for a local supplier or local buyer.  You’d respect the incumbent.

3)  You would focus on amassing an audience of local consumers that is large enough to provide incremental selling opportunities to local suppliers not achieving 100% success through competing channels (read: all local sellers)

4)  You would develop a toe hold in a single vertical, and then start “inviting” that audience down adjacent vertical funnels (Craigslist started w local event listings)

5)  You would buy traffic.  I can’t see anyone becoming liquid fast enough without paying for audience.

6)  You would take that bought traffic, and make sure each purchased user perpetuated your product beyond his own consumption.

7)  You would figure out what socializing listings really means, and what incremental value consumers get from engaging their graph in their own local buying and selling.

8)  You would figure out how to promise local suppliers higher close rates with less work.

9)  You would create a user experience that engages local consumers, not only at the point of buy/sell, but across points where they seek to engage with a local population (whether they seek to communicate, publish, ask, answer, meet, watch, etc…that population).

10)  You would recognize that buy/sell is not just buy/sell, but also search/find, speak/speak, give/take, trade/trade, and any other iteration of match between two complimentary local needs.

11)  You would not require local buyers or sellers to repeatedly return to your destination.  You would capture and categorize whatever they were buying and selling, go out, find the other half of their match where it existed, and deliver their match to them wherever they are engaged online.

12)  You would not try to “own” your users.  You would certainly service your users and build a relationship around that service, but you would allow anyone who is helping local buyers and sellers get together to pull your data into their environments.  You’d be happy when one of your local sellers found their buyer, independent of who delivered it to them.

13)  You would build a brand that focuses on the people behind the listings.  A neighborhood or city is not defined by geography, but by the people that inhabit it.

Not that Jumppost is doing this, we are JUST focused on local real estate.  Seriously. is not just a revenue generating local funnel that pays back in 30-45 days and allows us to cost effectively buy a large local audience (see #5)…

If you want to change how people in a local environment find each other based on need, you should come work with us.

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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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