Archive for July, 2014

When to walk from a deal

Posted on July 15, 2014. Filed under: startups, venture capital |

Negotiating a deal is an exercise in reasonability. As long as the other party continues to be reasonable and as long as you continue to be reasonable, the odds are good that you will get to a deal both are satisfied with. Giving a little and getting a little back and forth are expressions from either side of reasonability. Drawing a hard line in the sand is an unreasonable action unless it is absolutely real and you are prepared to walk if your terms are not met. I have no problem employing this tactic in a negotiation and do it all the time. The good part of this negotiation method is that you can clearly articulate your needs and they are often met. The unpleasant part is that you often have to deal with the pain of walking from something that you genuinely wanted to happen. Even when you sit down rationally and say “this deal doesn’t make sense at any terms beyond x” when you face the operational reality of not doing it there is a cost. You already decided you were willing to incur it when you drew the line in the sand…but it’s unpleasant to pay it nonetheless.

I was having dinner a few weeks ago with a friend 30 years senior to me who runs a company in a very different field from ours, and we were talking about this dynamic of “being willing to walk.” When all posturing is put aside, there exists the point where any CEO/investor/whatever is willing but doesn’t want to walk from a deal they value. I asked him about a big deal he was working on in which he had clear leverage “when it really comes down to it, are you willing to go through the pain in the ass and inefficiency of finding an alternative if they don’t agree?” and his answer was I think what most CEOs feel in these situations…he made a snake like motion with his hands as he said “nooooo….but maybe yes.”

We have this natural instinct to avoid the pain of walking…it’s a more basic instinct…lower level in the emotional stack…if you will…than the optimizing/strategic mind…and there is a dance between this preservation instinct and optimization that is probably healthy. Instinct governs you to be reasonable and work toward a shared goal at the cost of optimization…and the strategic mind is the kill switch that can override preservation instinct when the avoidance of pain has a smaller absolute value than the gain in optimization from walking.

So when do you actually walk from a deal? When your strategic mind tells your preservation instincts to shut the fuck up and go find the better deal that’s out there…

p.s. this post has nothing to do with Wildcard….be cool

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Wildcard Recruiting Secrets

Posted on July 10, 2014. Filed under: startups, wildcard |

Wildcard is 16 full time people right now and 4 or 5 part time…any given day we have about 20 people in the office…and we’ll double in the next year. To do that effectively while keeping our bar for talent as high as we have managed to date…it requires the effort of our entire team…not just founders…not just engineering leaders…everyone needs to become an effective recruiter for our company. To teach folks who haven’t built teams before, we talk a lot about tactical process and taking a methodical approach to pulling the people we want into our company. I just sent a note to our team in this vein that I thought might be helpful to other founders…it also touches on some interesting conversations we’ve been having about the importance of diversity at our company…so I thought I’d open source it:

Subject: Recruiting Samples and a note on diversity at Wildcard

Guys, as promised in yesterday’s gathering, here are a few real emails i’ve sent in the past that you can work off of for your recruiting outreach. Let me know if you have any q’s. I find the most effective stuff is straightforward and genuine with some supporting info about the company…

Also, we didn’t touch on this yesterday, but I’ve been talking with Doug and Khoi a bit about diversity at Wildcard. We know there’s a lack of women and minorities at Wildcard. Today’s makeup doesn’t fully reflect the way we want the company to look as we grow. Recruiting is very hard; recruiting for diversity is even harder, but we’re going to work very hard on this and try to get to a place that is more representative of what we want to become. I can’t say I have a wonderful playbook on how to bring more diverse candidates from all walks of life in the door, but as you begin your outreach, please take whatever creative steps you can to help us improve here. If there are things we can be doing internally as a culture and company to differentiate us and attract the most talented people from underrepresented backgrounds, please let us know or take the initiative to get them going yourself. We’ve got to do better here. We are missing out on game changers from communities we aren’t reaching or speaking to.

SAMPLE EMAILS BELOW Take whatever bits and pieces you like, or roll your own:

this was a real email i sent yesterday to a potential office manager +

Hey [redacted], I heard some things are changing at [redacted] right now and that you are awesome and potentially a free agent? I run a company called Wildcard here in New York that is going through a growth period and I think you have a really interesting background to help us upgrade on the operational side of things. Hope you don’t mind my reaching out, but I’d love to meet if you are interested in learning more.

A bit of background on our company. Wildcard is building a replacement to the mobile web on your phone. You could think of as a new type of browser that delivers native app experiences in response to your searches instead of slow, clunky web pages…It’s pretty cool stuff. We have 3 founders who all built a company called Hyperpublic together before this which was successfully acquired by Groupon about 2 years ago, and now we have a wonderful team of about 16 awesome people…mostly engineers and designers…working out of a great space on Grand St. Our main investor is General Catalyst Partners, where our board member is the founder of the firm and is responsible for their investments in Kayak, Airbnb, Warby Parker, etc.

Would you like to hang sometime next week?

And this is just a generic paragraph i guess you could attach to any email with a sentence at the end of a personalized paragraph that says “I’ve included a little background on Wildcard below”

Wildcard is building a replacement to the web on your phone. We’re focussed on a new technology called “cards,” and we are building a browser that displays native cards instead of webpages on mobile. The founding team (Jordan Cooper, Doug Petkanics, and Eric Tang) built and successfully sold their previous company, Hyperpublic, to Groupon, and our Design leader is Khoi Vinh who ran design at the New York times for a number of years and then founded Mixel, which was acquired by Etsy. Our core engineering team hails from Penn, Stanford, Carnegie Melon, MIT, Columbia, U Chicago, etc…and everyone here is incredibly ambitious and kind. We’re backed by a great group of investors led by General Catalyst Partners, where our board member runs the fund and is responsible for their investments in Airbnb, Kayak, Groupme, Venmo and Warby Parker. And most importantly…our product and technology are awesome 🙂

This was a mail i sent to a good full stack front end guy who i played on a soccer team with and know a bit (so had a little context going in):

could i persuade you to come see a demo of what we’re building at wildcard? I’d value your feedback and maybe it will wow you to the point where you’d leave the mothership of ebay and come build it with us…

This was the first email I ever sent the illustrious Max Bulger 🙂

any chance i could persuade you to come interview for a PM gig with me? I caught your background via twitter…i like what you’re putting out into the world

Typical/effective subject lines include “Hey” or “Yo” or “reaching out” 🙂


(p.s. in case you can’t tell, we’re hiring the best and brightest:

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Give it a minute

Posted on July 3, 2014. Filed under: startups, venture capital, wildcard |

On Tuesday night I went for a bike ride with my friend Pierre. He runs a company called Sunrise which I very much admire. We were talking about getting featured by Apple and he had a very astute comment. He said “of course, it’s wonderful, when Apple features you, but no matter how well you do with features in the App store, that is not going to make you successful…building a great product that people value is.” As we drilled down on the “that people value” half of that sentence, he mentioned Evernote as having created and effectively communicated 3 clear pieces of value that it reminds users of every session. I can’t remember them exactly, but it was something like 1) your information everywhere, 2) instant search, 3) easy capture. I may have gotten that a little wrong…i’m not actually an evernote user…but the gist was that Evernote has 3 concrete pieces of value that it’s users know and can clearly articulate as “what Evernote gives them,” and Pierre said every company should be able to articulate those 3 pieces of value. He said, “when you know those 3 things…the product roadmap writes itself.” The more interesting part is that Pierre felt he had only identified 2 at Sunrise, and that the 3rd had not yet been built. I commented that having the patience for the 3rd to present itself in the future is a leap of faith that is required to get to the promised land. I suggested that he had already made the decisions that would determine if Sunrise finds it’s three and becomes the megasuccess he hopes it will…and now all he needs is time for those decisions to play out.

My belief is that the team you assemble in the early days of a company either is or is not capable of building the product that reaches the promised land…and then as a CEO your job is just to create enough time and space for them to realize their potential. People often think that when you make an incredible new hire or bring on someone very special…that the company realizes her gain or value overnight…in reality, I believe that you invest in exceptional people and you don’t yield the results or “the return” on that investment for years. Brilliance takes time to express itself…that 3rd feature or piece of value…that product tweak or insight…that growth feature…or performance shattering technical breakthrough has a gestation period…and it requires an incredible leap of faith on behalf of a CEO or founder to simply be comfortable that the people he or she has assembled are the right people…and that if given enough time and space to express themselves deeply, they will find the promised land for you. There is this fable or false archetype in startupland that the CEO is out in front…leading a team of people in a direction that he or she sees…and that if they find the promised land it is because he navigated them to it…As I mature as a CEO myself, I am increasingly aware that it is actually the team that is out in front…collectively leading smaller interlocking efforts, that in aggregate set the path toward the promised land…and it is the CEO…pulling up the rear…making sure there are no sprained ankles, everyone is properly hydrated, and that with so many people confidently expressing themselves…nobody is breaking from the pack and going in a direction that is at conflict with the whole and the Company’s vision. Maybe this is not everyone’s approach, but at Wildcard I am certain that if we are to achieve our ambitious goals, it will be because we were able to stick around long enough for the people already sitting in this room to fully express their potential.

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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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