And Then There Were Three

Posted on October 28, 2019. Filed under: startups, venture capital |

For the past 50 days I put way more energy into our Associate recruiting process than I did looking for investments. That may seem out of whack, but I think it was an incredibly important decision for our firm. Yes, the stakes are lower than adding a GP to Pace, but when you are a team of 2 people, any 3rd person you hire will have a profound impact on the culture of the firm. I sort of sketched out the process before posting for the position, but found myself evolving it in a real time as conversations were happening. Here’s how it turned out:

1) We got way more applications than I was expecting. Roughly 300 people applied for the role largely referencing this post:

2) After reviewing everyone’s “cover emails“ and CVs, I took the top 30 applicants and invited them for 30 minute Zoom video screens.

3) In my initial post I encouraged folks from underrepresented backgrounds to apply. Of the candidates who received Zoom invitations, 43% hailed from underrepresented backgrounds.

4) To try to eliminate bias and make the best objective decisions, I structured the Zooms to be identical and asked the exact same questions to all 30 applicants. The primary purpose of the Zoom screens was to evaluate my communication plane with each candidate.

5) Each Zoom was broken into 4 parts:

  • I started with 5 minutes on my background and sharing more on Pace
  • I then asked candidates to spend 10 minutes on their background, focussed on the decision points in their career and how they approached them.
  • Then, I asked candidates to spend about 10 minutes teaching me about a business I might not know about. I asked them to pick a company, explain how it worked at a business level and a technical level, what they found interesting about it, and to the extent they had an investment thesis, to share that as well.
  • The last 5 minutes I asked candidates if there was a single venture investor, irregardless of whether they’d met or not, who they most admired (based on their public body of work, online persona, content, or potential previous interactions). The goal here was to get at a softer read on personal taste in people/businesses/style.
    • Side note: most popular answer wasn’t Marc Andreesen or Mike Moritz. It was Charles Hudson from Precursor (by a lot)

6) As soon as the video call ended, I ranked the candidate on a 10 point scale.

7) Once all 30 Zoom screens were over, I selected the 7 candidates who scored above an 8.5 and invited them for 3 hour in person meetings. For those meetings, I created a structured discussion topic outline, similar to what we use in our GP process, and used it as a rough guide to anchor the conversation.

8) All 7 of those candidates were incredibly impressive. I fully expect to collaborate with all of them in the coming years, but we whittled it down to 2 finalists.

9) Each finalist, neither of whom had any background in blockchain, was given the Ethereum White Paper and asked to read and understand as much as possible. The goal here wasn’t to pick the candidate who would best support Pace in crypto (we are a generalist firm), but rather to understand each person’s system level thinking and mechanical/technical comfort.

10) The last round of interviews was an hour with the candidate teaching me how Ethereum worked, followed by a dinner with Chris and I to get a feel for our group chemistry.

So out of all that, I am so pleased to welcome Blake Mandell to Pace Capital. A bit about Blake: He grew up in Florida and is a first-gen college student. His parents had a friend who attended Northwestern that said it was a good school, so Blake applied to go there. To help pay for school, Blake became a Cutco knife salesman, and at one point was the #1 Cutco salesman in the country (out of 15K people). He spent a year at Northwestern, though it was too vocationally oriented for him, so he took a year off, started a peer to peer storage business, sold it, and then transferred to Brown University, where he double majored in Math and Contemplative Studies. From there, Blake was granted a full scholarship to attend the Yenching Academy at Peking University (China’s version of the Rhodes), where he got his MA in Economics and won awards for his research. Somewhere in there he also had a stint doing applied machine learning research at UPenn. Last stop after Peking University was Boston Consulting Group (BCG), where he worked on some awesome technology and healthcare projects, and now he’s moving to New York to work with us at Pace. He’s a good person, good heart, extremely authentic and self aware, and I encourage anyone to reach out and spend time with him:

If you’re a venture firm looking to bring on an associate or analyst, the other 6 semifinalists were all super impressive. As I said, I plan to collaborate with each of them in the coming years and I’d be more than happy to make intros to anyone hiring for a similar role:

Read Full Post | Make a Comment ( None so far )

Wework for the rest of the country

Posted on November 28, 2018. Filed under: startups, venture capital |

I just took a glance at Wework locations around the world, and it confirmed what I expected to see. Wework has almost 500 locations around the globe, and they are all in densely populated cities. This makes sense. Largest markets, expensive commercial real estate, large young workforces, etc…I get it. That said, i wish that this type of physical infrastructure for remote/independent work existed in some other parts of the country.

My wife and I regularly go to a small town in the Adirondacks with a population of 207. The larger surrounding area within say a 20 minute drive is about 10,000. Every time I go there, I think about the local community and economy and how one could improve it. There are countless stories of small town America dying, younger generations emigrating to larger cities for more opportunity, etc…The industries most prevalent in the region are not surprising. Construction, small retail, car dealerships, outdoor travel services, maybe an occasional bar or restaurant…and that’s kind of it. That’s not fair. I guess there is a lawyer and family counselor and of course school teachers, doctor, etc…but one thing there is not a lot of is connection to the digital and tech economy. Part of that is cultural, part of it is the relative recency of advances in distributed work, and part of it is exposure and what you see around you as your growing up in this environment.

As the wealth gap grows and that wealth concentrates in cities, I often think about how to bring dollars and jobs into these more rural areas. How many large, scaled companies both serve and employ rural communities? I often think of Walmart, which I know has it’s warts, as a hundreds of billions of dollars scaled commercial enterprise that systematically brought “outside dollars and jobs” into these smaller areas(and built something very valuable in the process.) How many other public companies are looking at the map of the United states and putting pins in 10,000 person geographies as a strategic roadmap? Not that many that I can think of.

So back to Wework. My inlaws recently purchased a (very inexpensive) plot of land on the Main Street in this Adirondack town with 2 restaurants and a supermarket. The discussion has been “what does the town need? what kind of businesses could we stand up here to both recoup our investment and contribute to the community?” My favorite idea, which might be dumb but is exciting to me, is to build out a coworking space, with really good internet, decent coffee, basic office infrastructure, and community gathering space. I love the idea of trying to provide some physical infrastructure to support entrepreneurship, remote work, SMB operations, and importantly connection to the rest of the economy. You have to squint to see it, but I think if you want these more digitally native career opportunities to make their way to the small towns in our country, it’s not enough to count on the internet alone to connect everyone. I think there’s some significant education, retraining, and vocational programming that would be required for such a future, and exposure is a big problem in getting that information to at least the one community I know. A physical presence of some form, I believe, is a requirement if you want to gain local exposure…so in some ways I view the “Wework for everywhere else” to be that. My hope would be that there is enough demand for monthly desk space to cover the cost of build out and land purchase/lease, and then with some smart programming alla General Assembly or an integrated Meetup/Wework, but relying much more heavily on video and telepresence, maybe you get a new revenue line item around education and training, and as you provide those services, demand grows for complimentary physical infrastructure, and some kind of virtuous cycle occurs.

Obviously, there are a lot of challenges here. First and foremost, I think, is town/community acceptance. There is definitely a hesitation about embracing outsiders and outside influence at least within the community we know. Getting buy-in and having a positive word of mouth as it ripples through town is hard. I’d imagine the effort is similar to how the Church might have approached such an endeavor decades before. It has to be good for the town. It has to be native to the community. It has to give more than it takes. And it has to be respectful and cognizant of the way things are in any given community. It would be so easy to drop in tone deaf, build out the thing because the model says it works, and have the pillars of the community ice you out of business. So it’s a big ground game effort, and that might be expensive…but maybe the local church or town boards, etc, if alignment is clear (and I think it is)…are a distribution channel to roll something like this out.

A second and real concern is “maybe there aren’t enough people doing this type of desk work to support the Wework model.” I built a chicken scratch model that wasn’t entirely implausible (less people, but remember real estate is cheap), but someone more intimately familiar with real estate and the coworking business model might eviscerate this claim. No idea.

I just think it’s weird that there is no physical infrastructure to support remote work in the communities that are definitionally remote. If it works, and if the local economy improves, not only could you build a profitable P&L, the underlying real estate asset in which you invested should theoretically appreciate. Feels like a win, win, win. I am far from an expert in these matters, please point me to people doing this or problems I’m not addressing, and if you’re building a startup in this vein, I’d love to support you as an Angel Investor:

Read Full Post | Make a Comment ( 4 so far )

Falling in love/hate with Telegram

Posted on December 13, 2017. Filed under: blockchain, startups, venture capital |

Somewhere over the last few months Telegram has become my most used App on my homescreen. A friend invited me to a “secret group” made up of blockchain fancy people, and I dropped into something I had been missing since Twitter changed their @replies and public discourse logic in 2008 or so. At it’s core, Telegram is an encrypted messaging app, but it’s group discussion features have me gaga. I really miss the public conversation of old twitter, the ability to follow a back-and-forth conversation that was lost a long time ago, and Telegram has some really nice features such as public @replies and threading, that enable 200 or so people to all talk and follow along without getting lost. There’s an intimacy to a “secret group” and nice admin permissions that enable the host or creator to boot non-additive or abusive community members while governing new admissions as well. The combination of Telegram’s security profile and these group management features lead to an openness, risk taking, and trust within the groups I see, that is ideal for learning, getting to know and debate new people, and expressing thoughts and feelings that would be less relevant to a large and diverse following on Twitter.

It’s been fascinating to watch these groups find their cadence, build community, and make decisions together as they move from no governance at all, to increasingly structured governance over time. I admin a group that is made up mostly of people who have participated in our Crypto Club reading groups with new invitees joining every so often…and I have a newfound respect for forum moderators, group administrators, etc. Each group I’m in has a different complexion. The Crypto Club Reading Group tends to be pretty analytical, protocol design focussed, and there’s good discussion on emergent projects and individual mechanics within them. Some other groups I’m in tend to be more event driven, trading focussed, and they’ve become some of my best content discovery channels surfacing links and news related to blockchain well before I see things in Twitter or elsewhere.

A carefully curated Twitter feed used to be my primary flow of information and thoughts, but in Telegram I am finding similar properties around discovery of new information, with an added layer of openness, sentiment, analysis, and even entertainment as people get to know each other and personalities come out. I think in my head messaging platforms, encrypted or not, were tools for 1-1 or small group communication…but I’ve come to learn in Telegram that there is a happy place between public microphone, active conversation, and ever-evolving community where strangers and friends can publicly but intimately interact…it’s unique.

I say i’m falling in love/hate with Telegram because it’s quite consuming. My wife has noticed that I’m “always in that new chat app” and the cadence is on par with an active/bad Slack habit, or something to that effect. I deleted Slack form my phone 2 years ago for this very reason, but Telegram has pulled me back into a higher frequency discussion for better but also for worse. I am even in one group that kicks out members who have been inactive for more than 4 days…either you are there and you share the conversation (and addiction) or see you later!

Overall it’s been nice to connect the New York chapter of Crypto Club with the West Coast chapter, and I was looking for a way to do that for a while, and I’ve enjoyed finding new community and thought partners in other groups as well. It’s definitely a give and take, but overall I think I’m willing to succumb to the distraction Telegram brings…said another way “invite me to your best Telegram groups: 🙂

Read Full Post | Make a Comment ( None so far )

“Experts” won’t be first

Posted on November 14, 2017. Filed under: blockchain, startups, venture capital |

I distinctly remember the moment I became enamored with the application layer of mobile computing. The year was 2006…it was pre-iPhone, but I had just gotten a fancy job at General Catalyst Partners, and with it came my very own Blackberry. For the first time I could kind of access all of the internet from my phone, and I got a taste for what native smartphone experiences like Blackberry messenger had to offer relative to the apps on dumb phones.

I started imagining what apps might look like that could be built for a smartphone and began to develop a thesis at the firm around what I was calling “mobile information capture.” This wasn’t an easy path for me to champion at the firm. At the time, GC had built quite a brand and track record investing in the pre-smartphone mobile ecosystem with investments in companies like Jumptap and M-qube, and there were two very analytical, well respected members of the team, John Simon and Brad Hoover (who btw is now CEO of Grammerly…go Brad :), who kind of owned mobile at GC. I remember Brad in particular having talked to thousands of mobile companies…to the point where any new mobile deal that came into the firm would get “Hooved,” and take it’s place in a very intricate mapping of the entire ecosystem. The best things would surface to John, and they would lead our investments in the space.

I worked on my thesis for a while, through the launch of the first iPhone in 2007, and as I built conviction around the investment opportunity I remember presenting it at our annual partner offsite as the most interesting new market for us to focus on as a firm. My ideas were well received, but I remember distinctly being told by our mobile guys that “smartphone penetration was nowhere near where it needed to be to focus on the application layer of these platforms.” I wish I could remember the penetration at the time and the 5 year projections they espoused, but needless to say, those projections were wrong and our very expertise in the pre-app days of mobile investing was what blinded the firm to very valuable investments in the subsequent few years.

I don’t tell this story to brag about my rightness, but rather as a cautionary tale to those that insist that it is “too early to invest in the blockchain’s application layer” today. I should define application layer in this context, less as the thin smidge atop the “fat protocol” that’s been articulated by others, and more as protocols or varying “fatness” and depth in the stack that organize non-technical actors to participate in a network, marketplace, or behavior together. Some of the smartest experts in blockchain, who have been investing in and around the blockchain for 6 or 7 years…will state plainly that infrastructure is in focus and it’s too early for apps. Many followers of their expertise, will parrot such phrases, and the investor ecosystem as a whole will develop consensus around that idea, but I have to say…I hear these statements and they remind me of the “mobile guys” in 2007. It’s not because the analysis is wrong…objectively infrastructure tends to precede applications in developing markets, and there are gating challenges to consumer and business adoption of protocols being developed today…but as the mobile pundits of the early 2000s will tell you…early killer apps have a way of sneaking up on the experts.

Conservative market wisdom says “no applications are really being used today”…and therefore it is going to be a long time before any application is used widely…but that is not how I see things at all. I think it’s more like “no application is being used today (cough bitcoin), but some protocol that traverses the infrastructural & application layers in the stack, simultaneously and in a deeply integrated fashion, will be used widely, by surprise, and quite abruptly to the chagrin of patient experts.”

I could be wrong about this, I often am. I’m no expert, just a dedicated student, but to be closed to the possibility that the market matures in a more uneven way than whatever graph says “wait” seems foolish to me.

I’ve heard similar “wait” narratives, again from very very smart investors, around blockchain protocols that organize human work: “It’s too difficult to invest in protocols that interface with humans, I’m only investing in systems that coordinate machines.” Again, not a dumb analysis, especially given the multiple well respected blockchain systems that organize machine work around storage, compute, or bandwidth, but it’s just not convincing to me in a world where the entire collective consciousness in the space turns over weekly, sometimes with giant step functions on the back of a single creative design…there’s too much horsepower and experimentation and creativity pointed at the possibilities of bottom up organized human/labor systems to negate the possibility that someone is going to get it right, securely, and quicker than expected.

Architectures that usher in any of these “farther out” possibilities may not look like what we see today. Experimentation around offchain vs onchain functionality, the spectrum between centralization and decentralization, and new game theoretic and economic designs for contribution and authentication of value all present the possibility of worm holes into next year’s future showing up tomorrow.

In such a state of flux I prefer to remain quite open to radical and “too early” possibilities…and although I’m not an expert with a fancy brand or firm behind me, I’d be happy to invest in you if you are taking a swing up the stack or out of the bounds of today’s popular protocol flavors:

Read Full Post | Make a Comment ( 1 so far )

The path to billions of “programmers”

Posted on April 5, 2017. Filed under: startups, venture capital |

I have always been fascinated by publishing platforms…I love the idea that a new platform or technology has the ability to give a voice to someone…or many people…that previously did not have one. I try to stay very current on the places that people go to express themselves, and I think overall the internet has done a pretty good job of giving everyone and anyone with a computer or camera the ability to publish. It used to be that in order to have a public voice, you needed to be a journalist. The technical requirement to publish was a journalism degree, and therefore the number of people who both had that credential and were able to get a job at a media outlet limited the universe of potential voices in the world. Along came blogging platforms, and all of the sudden you didn’t need to have a journalism degree or a job at a newspaper or magazine, you just needed to know how to write. The universe of voices expanded to maybe anyone with a high school education or liberal arts degree, and all of the sudden we had more public voices in the world. From there, came microblogging, and now you didn’t even have to know how to construct a 3 paragraph essay…if you could assemble a sentence or a tweet, independent of structure…you too could have a voice. In parallel, publishing platforms like instagram and Facebook enabled visual thinkers to express their voice through photos, even if they couldn’t conjure a thought in text. Each time a new platform came along, the schooling and technical writing proficiency required to publish and have a voice declined…until we arrived where we are today, where let’s say a few billion voices have joined a conversation that a few thousand were previously dominating. I had a post a few years ago that described these successive breakthroughs in publishing platforms and their impact on expanding the universe of people with a voice. I visualized each new platform as unlocking a new and larger rung of publishers in a series of expanding concentric circles. There I focussed on the reduced effort that each new platform required to publish, but here I focus on a reduction in required training to publish because I think there’s an important parallel to be drawn between the history of publishing platforms and the current state of programming and software development.

In a sense, programming and publishing an application, be it a website on your own domain, a mobile app in the Appstore, or really any piece of automation is a lot like publishing an article or blogpost. You write within the guidelines of the platform you are writing for, and if you have the background and understanding of the language you are writing in, you can take something that’s in your head and express it externally. When I started working in technology, most of the programmers I knew had formal computer science degrees. If you wanted to write software, you needed a lot of education, and therefore the number of programmers in our world was quite limited. A few years later, there was even a bubble of sorts in aquihires, as demand for people who could write and publish software far exceed those trained in the field. For a host of reasons, not the least of which was the emergence of more flexible programming languages and frameworks like Ruby on Rails, the schooling required to express thoughts as software and applications declined. Today, instead of 4 years at MIT, 3 months at programming bootcamp can land you a job writing software, and certainly provides the basics required to build a basic web application on your own. Advances in modern programming languages and abstractions of knowledge dependent layers in the development stack have played a similar role in programming to advances in blogging and microblogging in the publishing world. As a result, the universe of software publishers has grown, more people can express themselves through software, and the universe of people capable of writing automation has widened…but still the hurdle to express oneself or an idea through software remains too high.

I find myself looking for the platform or technology that is going to meaningfully increase the number of people who can “write software” and I don’t think it’s going to be an educational platform so much as a much more flexible programming language or platform that more closely mirrors and accommodates natural language. I know we are far from it, but when we get to the point where a person can write automation in plain english, we’ll have billions of people writing software much in the same way as we have billions of people publishing thoughts on today’s publishing platforms. What automation we write will look and feel different than what you see in the Appstore today…early hints of this future might exist in platforms like IFTTT and Workflow…but even these environments are quite rigid and lego-like when compared to a free-text box that any liberal arts student could approach. Yesterday I came across this YC company called Algoriz, which positions itself as free-text based algo trading without the need for programmer…in practice I found the tool far from this promise, but in positioning I was captivated by the idea of unlocking a new concentric circle of programmers…even within a tight vertical like trading…and my mind immediately longed for the more generic version of this promise.

When you go down the actual rabbit hole of approaching something like this, you quickly get into concepts of templates and modules and hardcoded mappings vs generic and broad capability…the state of the art ain’t pretty in this domain…but I’m more than ready to talk to anyone who is trying to grow the universe of “automation publishers” less through education and more through advancement at some platform, technology, or even interface layer. Who is taking the requirement to publish software from a 3 month bootcamp to a plain vanilla liberal arts education…and who’s doing it more flexibly than templatey? That’s something I’d like to back…

Read Full Post | Make a Comment ( None so far )

Vlog #4: new office, new observations, new data, new constraints

Posted on February 18, 2017. Filed under: startups, venture capital |

Happy Saturday. Here’s a ~25 minute update on what I’ve been thinking about and working on over the past few weeks.  I know that’s a little long, but pour yourself a cup of coffee and just imagine we are having a quick coffee together…Please forgive the slightly congested voice…at least I didn’t sneeze during it. Was worried that might happen 🙂

Read Full Post | Make a Comment ( 1 so far )

The nuances of a livestream

Posted on October 31, 2016. Filed under: startups, venture capital |

img_7367Last week I livestreamed my lunch on Facebook…roughly 60 friends joined me as I ate alone in Abington Sq Park, and another hundred or so probably watched a recording of the live lunch that I published to Facebook after the session ended. My sister emailed me the next day and asked if I wanted to meet for lunch because “I seemed kind of lonely on my FB Live lunch.” I tried to explain that I wasn’t lonely at all, that live video is a thing now, and I was experimenting with a new publishing medium…but even after more explanation of the live streaming dynamics in China, why I was doing it, how people are making money doing it, etc…I’m not sure she’s totally on board.

Beyond FB, I’ve spent a time on some of the other livestreaming platforms, both watching the broadcast use case, but also getting a little more familiar with the more nuanced social dynamics at play…and while I understand the power of treating Live as a media opportunity, and why traditional publishers and fast following (or maybe now fast leading) influencers are trying to use it to connect with and grow their audiences, i think for everyday folks there are some more interesting opportunities that Live affords.

As I sat in the park, eating while trying to hold a steady camera in front of my face, I was actually reminded of the most interesting and gripping attribute of my experience in Virtual Reality. In VR, the killer experience for me is “presence.” I’ll define presence as “a feeling of really being there,” and if with others, social presence would be “a feeling of really being there with others who are really there.” In even the most elementary of chat applications in VR (i think v-time is the one I used most), I felt that I was actually with whoever I shared a virtual room with…in a way that most aysnch or near real time experiences, never really achieved. As I streamed live during lunch, while the experience of interacting with those who joined my stream was still quite clunky (comments in 2-way communication in FB Live needs a serious UX overhaul), I did feel a sense of presence and togetherness that certainly doesn’t materialize through any other publishing platform I’ve used to date. Interestingly, when contrasted with say Facetime (which is 1-1), the feeling of streaming to many with lower commitment and expectation of dedicated attention, actually INCREASED the sense of presence I experienced at lunch. With Live, there’s an ability to “be” in whatever environment your in…to remain one foot in the real world…not sucked into the screen completely in the way Facetime requires…and somehow that “being” and “being with yourself” while “being with others” makes for a more realistic and true sense of presence than simply “communicating” through an app like Facetime…there’s a difference between being and communicating…and Live is this weird and perhaps beautiful mix of the two.

From far away I looked at FB Live as just another place to broadcast, but up close it appears to be a place to feel connected, to fight lonliness, to be present with your friends, and maybe even to broadcast your availability (whether in person or virtually) without the stigma of a status update that says “anyone want to go to the movies?”

In some sense, if FB status update is saying “what’s on your mind?” and a Tweet is saying “what’s happening?”, a live stream might be saying “I’m here, I’m present” and the use cases that emanate from that statement push well beyond “listen to what I have to say” into “I am available to talk,” “I am free to meet,” “Let’s be together,”…i guess maybe what i’m saying is that livestreaming feels as much an invitation as it does a statement…and that’s unique in a publishing platform.

Read Full Post | Make a Comment ( None so far )

Life is an experiment

Posted on May 16, 2016. Filed under: startups, venture capital |

Life is an experiment…when I was a bit younger…i lived this way very truly…the world was this fabric that you could touch and bend…and most of what i did…whether professionally, socially, romantically, or otherwise…was try to bend it. I hated the concept of “the path”…I detested highly predictable outcomes and the decisions that would lead to them…all I wanted to do was look at the world as an experiment and fuck with it because I could see it that way, and most other people weren’t trying to. I was not outcome oriented. A successful bend of the fabric, or the discovery of a nuanced wrinkle…these were wins for sure…but not toward any end beyond empirical progress…simply exploring and testing was the reward, and it was everywhere.

When you start to get comfortable in whatever reality you have designed for yourself, you stop trying to bend it. You start to get attached to the notion that one outcome is better than the other…you start to believe that your current understanding or context is better than what might be around the next corner…and this penchant for stability creeps in and starts telling you to run less experiments…or run more outcome oriented experiments…you start to develop a will as to which way you want the experiment to unfold…and maybe you stop taking on experiments that don’t have some purpose beyond a specific desired outcome.

I feel as though I’ve become less plastic..less willing to treat life as an experiment…maybe for good reason…i have all these good things in life that i don’t want to disrupt. I have financial stability from hyperpublic and lerer ventures. I have romantic stability in my soon to be wife. I have social stability with friends i like. I have professional stability accrued over years of hard work and thought…these are all things that make me happy…and if i only run experiments where a likely outcome will strengthen them…there’s a pretty darn good chance that this nice reality will persist…

The problem is…part of my energy…part of what makes me me…comes from instability. I like shaking things up…I like change…and it’s in these changes that i see and love the fabric of the world. I am the deepest expression of myself when I am learning and discovering…when i am touching newness…and I am something less when I am moving through things I’ve seen or done or understood before.

So when life becomes less of an experiment…i become less of myself…or at least the self i feel most connected to.

Things have a way of stacking up…as responsibility and expectations and life cement…and it gets easy not notice as the experiment slows down.

I really want to find this experimental mind again…and not to rip out that which I truly value (my future wife might be freaking out a little while reading this…), but certainly to risk that which i have passively come to accept as real or true.

I used to flee from complacency like it was the devil…these days I walk away from it deliberately like it’s someone i don’t care for…but there’s probably something in between that is a little more me…and i’m really going to try to reconnect with that. If you know me, please help me stay true to this goal.

Read Full Post | Make a Comment ( 1 so far )

Justinkan, Grantcardone, and the voices of Snapchat

Posted on April 28, 2016. Filed under: startups, venture capital |

I spent the day yesterday digging into Snapchat in a pretty deep way. I’ve wanted to do this for a while. One of the most interesting things about Snapchat, is that the user experience completely breaks from all of the conventions that precede it…so really getting into it, and getting the full impact of the experience, requires effort, exploration, and poking around. I’ve been on Snapchat for a very long time, and used it in a pretty superficial way forever…but I’ve always had this feeling like “i’m doing it wrong”…I see a friend use faceswap, or a filter to make lasers come out of their eyes, and I’m too stubborn to admit that I don’t know how to find that in the app. It must be some 3rd party publishing tool they are using? no…you have to long press and hold your thumb down over your face to evoke this hidden feature…somebody has to tell you how to find it…it’s almost a secret…

Even the most fundamental of actions, like finding people to friend or follow on Snapchat is incredibly difficult. I spent a few hours, asking my friends on twitter to send me good accounts, reading lists of “good snappers” to follow, and playing w a 3rd party discovery app called Ghostcodes, trying to build up a good group of people to follow…Why would they make it so hard to find good people…well…for starters this isn’t Twitter…and no matter how much I might want it to be video twitter…it’s not. I think we have a bias when exploring new platforms to bring our habits and expectations with us from the last place we felt at home. I love twitter as a publishing platform (a place where a person can have/express a voice), and there is no question that Snapchat Stories is a new and potentially richer publishing platform…but because I learned to have a voice on Twitter, I keep trying to fit Snapchat into that place where I learned. Here’s where I’m at a disadvantage to the generation who first found their publishing voice on Snapchat. They didn’t bring any bias with them…they learned within the UX and context of Snapchat, how to publish on Snapchat, so their natural instinct is to create and speak in a way that’s native to the platform. One of the first things I considered, was how hard it must be to amass a “following” on Snapchat. Someone like Justin Kan, who has been recognized for creating great content and emerging as in influencer on Snapchat…he must have a fraction of the audience that he does on Twitter…not because he’s better at Twitter than Snapchat, but because it’s so fucking hard to find and follow him on Snapchat. Yes, their are Snapcodes (the weird image/QR code upper right on this page)…but even those are a mystery you have to commit to figure out. I’m pretty tech forward, and only yesterday learned how to properly use them. I was screenshotting Snapcodes for the longest time, and then searching my camera roll in the Snapchat app, to select screenshotted codes to add to my friends list. Turns how, if you just photograph the Snapcode through the Apps camera function, it will auto-friend these people without selecting from camera roll. Where would I have learned that things worked this way? There’s no tutorial, or explanation…and that’s the point. Maybe snapchat doesn’t want to turn into Twitter…maybe they’d prefer your graph of friends/followers to be small, and intimate, and true friends vs followers…maybe Stories aren’t for influencers or publishers…maybe they are for friends and loved ones…or maybe they ARE for influencers and publishers…but only if influencers are willing to play by the rules…which are that the content here is intimate, and raw, and you need to behave like you are speaking to friends, even if you are trying to speak to 1 million of them.

Something interesting I’ve noticed is that the production value of content in my Snapchat feed has risen in the last 6 months or s (if you’ll call it a feed…Stories were very unfeedlike for a while…but with the recent autoplay feature that rolls through all stories without needing to tap, i’d argue that this is now a non-vertical scrolling feed of content). “Production value” is the amount of energy/time/thought/polish/expense that is put into creating content. Blair Witch Project was low production value film. Avatar was a high production value film. Whereas my friends’ stories used to be quick/observational/quirky frames (likely a result of creators who first found their voices on instagram, bringing these habits with them to Snapchat), now my friends are starting to speak into the camera, plan sequenced shots ( a “snapstorm”), and even create art and interstitials between shots in their Stories. This isn’t the poop emoji on a friend’s face anymore…people are trying to say something in this channel now…they are trying to see it while taking advantage of the richer format…they are trying to publish. Interestingly, the ratio of production value to audience is pretty shitty on Snapchat compared to platforms like instagram, twitter, and facebook. It might take me 5 minutes to create something good on Snapchat that only 40 people will see, whereas it might take me 15 seconds to create something good on twitter that 7000 people will see…and still..after a few days getting into it, i’m happy to do it. Why? because it’s fun, and video is richer, and importantly…the environment shapes the content and sets an expectation of levity and fun and rawness that inspires me to make a new style of content that I like and that i’m proud of. All of this is to say that Snapchat stories, while rebuking the legacy of twitter/facebook/instagram at every design turn…is undoubtedly on a course to enable hundreds of millions of voices as it’s users become publishers. I think discovery will get a little easier (as signified by their recent roll out of a url to “addme on Snapchat”, but we’ll probably see some more ground up features designed to make finding voices easier on the platform…one thing you can bet on…is they won’t be the mechanics we’ve seen from other’s in the past…like everything else in the experience, they’ll be original, non-intuitive for migrators from existing platforms, but natural for natives and careful non to disrupt the tone that makes Snapchat content unique.

There’s still a lot that in Snapchat where I still feel an outsider. I know native users are having rich 1-1 chats, acting less as publishers and more as messagers…my limited 1-1 messaging has felt disjointed…a function again, of bringing my expectations from SMS, Facebook, and email. I guess as more of my graph is willing to “relearn” how to message in this channel, volume will pick up, and I’ll get the full experience…but for now I can only look enviously at Olivia’s 10 year old brother who didn’t have to unlearn SMS to enjoy 1-1 messaging in Snapchat.

As an aside, for those who are still feeling a little “outsider,” here is a bit of a cross section of usernames to get you started. not all people who’s Stories i like, but a bunch of the different flavors of publishing that people are doing on the platform:

arnoldschnitzel (feels like you are a perpetual student in his kindergarden cop class)
justinkan (creative content creation/style)
grantcardone (this guy is the worst…but worth seeing just how terrible he is)
man_repeller (professional publisher migrating to snapchat)
micdotcom (professional publisher migrating to snapchat)
rbfishman (lifestyles of the young and handsome socialite/entrepreneur)
yesjulz (party/nightlife)
therealdrmiami (platic surgeon in MIA)
msuster (vc blogger…using it as educational platform)
kimkardashian (celebrity)
djkhaled305 (celebrity)

i don’t have the energy to upload all their snapcodes for you…touche snapchat…

and i’m jordancooper1…but instead of name lookup…maybe be advanced about it, open snapchat, and use the snapchat camera to photograph that weird picture in the upper right on this screen (or screengrab it from mobile and figure out how to add by Snapcode in the settings…)

Have fun.


p.s. i think it would be cool if Snapchat adopted the ghost emoji as a replacement for the @ sign before their user handles. so instead of i’m @jordancooper on twitter…i could be “Ghost on Apple iOS 9.3jordancooper” on Snapchat

Read Full Post | Make a Comment ( 4 so far )

A Viral VC Model

Posted on April 25, 2016. Filed under: startups, venture capital |

I’ve been spending some time thinking about disruptive models in venture capital lately…here’s a little thought experiment:
If you are a founder raising seed capital…while personalities and people deploying capital vary, the product investors are selling (institutional seed capital) is for the most part pretty consistent…money is money. Yes, folks tweak terms so that their product is more or less dilutive, more or less controlling, etc…but standardization of docs and rampant access to capital have kind of leveled out these variables, and really reduced a founders’ choice of provider down to “do i like this person? do i think they can help me? and do i care or do i just need the money and believe they won’t hurt me?” I’ve seen a few interesting wrinkles in the capital structure/vc product that enable different investment approaches on the investor side (i.e. angelist, special purpose vehicles, etc), but most of these variations from the standard don’t dramatically impact founders math or incentive structures when making decisions about with whom to partner.

Something that is pretty clear, is that more and more founders are and want to be investors as well. In 2010, when I first joined Kenny and Ben as a Partner in Lerer Ventures, while simultaneously building Hyperpublic, people really had a hard time understanding how I could or would want to do be an investor and an operator at the same time. Today, you can’t swing a dead cat without hitting a founder/operator who isn’t also a venture partner/advisor/scout/angelist syndicate lead, etc… for some vc related entity. I’m exaggerating a bit, but it’s obviously a thing. Over a 5 or 6 year period, exercising both my investment and operational minds, I found many points where one activity would feed and improve the other…so much so that I don’t think it’s surprising that more operators are looking to get involved in early stage investing while executing on their own endeavors. It’s great data, a great networking platform, and it keeps you creative and broad while your deep into your own endeavor.

What if there was a new VC fund that bent the financial product being offered to you, the perspective founder…let’s call this new fund ViralVC. ViralVC doesn’t exist and I don’t plan to make it exist, but for purposes of this explanation, the pronoun “I” represents the Managing Partner of ViralVC. What if my $200K investment in your company came with a matching $200K check for you to invest in another company? What if taking my investment enabled you to make an investment without risking your own personal capital? If the deal works out, you can keep half the carry and build your credibility and track record as an investor. If the deal doesn’t work out, no worries…make it up to me by crushing it with your own business, which we’re already partnered on by way of my initial investment. I kind of like this idea of every investment a fund makes perpetuating a second investment, and using the initial portfolio of founders/their DNA as the filter for who else is interesting and special and of a similar value set.

Most seed funds hit a point where their partnership doesn’t scale to cover the number of investments they want to make/manage, but what if a portfolio of founders played a more active, yet non-distracting, role in investment identification and management. Theoretically, a seed fund could scale to distribute very large sums of money without bumping up against the constraints of today…I could see a path to deploying funds well beyond the $100M fund size that most seed funds max out at…in fact, i could see a path to responsibly, intelligently, and profitably deploying on the order of billions of dollars of capital into the seed stage asset class, simply by giving every recipient of capital a matching check to invest capital, so long as they agree to shepherd the investment and treat it with care. If you make great initial decisions on where to invest capital and in what founders, and apply a simple rule for portfolio founders like “your matching check is unconditional, so long as I, the managing partner, gets to meet the recipient, and we together agree it is a good investment. if i don’t agree, we don’t invest in this company, but you retain your matching check, go find someone else/better/different.”

It’s not a new idea for seed funds to invest in “connecting founders to each other” or “platform” as a form of scale, but it is new to make founders in your portfolio into investors of your capital, in an unconditional, non-one off way. I think the key would be to build great systems of communication and reporting to mange the network of investments and founders as it scaled beyond the first few generations of investment…and to build a crystal clear and well understood set of values for the community to abide by…so clear that even at large numbers, the group could operate as a cohesive unit to maintain and manage a consistent brand to the market and perspective founders…also key would be to deeply scrutinize the dna of early founders/recipients, knowing that the out years DNA of the portfolio will emanate directly and as much from them as it would from you, the Managing Partner of the fund.

So now, as a founder you could take someone else’s money, or you could take ViralVC’s money that comes with a matching check for you to deploy, significant upset economics, new experience and information, admission into a community of like minded founders, and the ability to give this exact same gift/value proposition you’ve received to whoever you believe in, regardless of how well networked or branded or popular they might be.

Kind of an interesting thought exercise…as ViralVC, you could lose a lot of money quickly executing on this model…but you could also completely upend the seed stage asset class if you did it right…

Come to think of it, what fun is a thought experiment without putting it to the test. I’ve got a $25K angel check for anyone who’s raising. If you earn it, I’ve got another $25K check for you to deploy (you keep 50% of the carry). Any market, any layer in the stack…just be original and genuine and creative and wierd. (put ViralVC in the subject).

Read Full Post | Make a Comment ( 1 so far )

Your Complex Relationship with Your Phone

Posted on January 6, 2016. Filed under: startups |

Every New Years for the last 10 years or so my close friends have a tradition. We used to travel together ever year, before people got older, found girlfriends, etc…but even as the group stopped assembling, we always send each other some reflections on the past year, goals for the next, and what we hope to improve over the course of the year. In the past, there has been a lot about career development, relationship development, physical fitness and health, mental awareness, etc…but this year I noticed a striking pattern. Between this close group, and a broader set of folks who shared their resolutions with me, I noticed that what feels like 80% of people, myself included, were focussed on changing their relationship with their phone. For me it was “be more conscious about when I use my phone. Make every session a conscious choice.” For my friends it was “no phone in bed,” “don’t check email until 8 AM, “use my phone less,” etc…

Here is a part of our lives that we engage in very frequently, that on some level it feels like we are all trying to limit, or reduce, or pair back. I sit next to a woman at work who has a game with her friends, where everyone has to pile their phones on the table at dinner, and the first person to reach for it before the meal is over has to pay. It is clear that we don’t feel in control of this beast that is getting stronger, and better, and more prevalent. For all the merits that come with a super computer in your pocket, there is an undeniable anxiety associated with what we are losing in the process. People feel harmed by their habit of engaging with their phone “more than they should.” When I graduated from college, many of my friends smoked. Resolutions at that time would be “quit smoking,” “smoke less,” and “get down to half a pack a day.” A behavior, which provided pleasure, social utility, and enjoyment…that was known to be harmful by the user…that people couldn’t quite take control of.

Addiction: a strong and harmful need to regularly have something (such as a drug) or do something (such as gamble)
– Meriam Webster Dictionary

If you have ever felt addiction, to say smoking, or coffee, or alchohal…you know the feeling when you want it and you are trying to resist. It calls to you, like the ring in lord of the rings…and no matter how many times you recognize or tell yourself that you don’t want to give in, the fight is persistent, and unwavering, and almost physical.

This morning I woke up at 6:15AM and I refused to look at my phone until I left the house at 8:30. First battle was right after the alarm clock went off…all those push notifications…waiting for me…and I immediately turned my phone over. Next, while waiting for the coffee to brew…Olivia is still getting ready…I’m just sitting here…VERY STRONG urge to occupy myself with my phone. The amount of energy needed to say no, look out the window, and think a little bit, independent of a device, was immense. The pull of the phone passed, and I proudly shared with Olivia that I hadn’t used my phone once since we’ve been up…Next challenge, 30 minutes later…the bathroom…what else am I going to do during my morning business? Then…we’re waiting for the elevator…stopped at a traffic light…you get the idea.

As a consumer facing startup, you optimize around metrics like sessions per day, time in app, days used per week. The panel in Mixpanel to measure user engagement is titled “Addiction” for god’s sake. You have this incredibly motivated, incredibly intelligent population of entrepreneurs and technologists trying to addict you…they are the force, behind that lord of the rings pull, that collectively, but not independently, are helping you to lose control of this powerful thing in your pocket…It isn’t mailicious, each one, is hopefully trying to deliver value, and not just take attention, but there are litterally thousands, if not hundreds of thousands of people…on the other side of whatever discipline or restraint or boundaries you are trying to set for yourself.

The other day I saw a new feature in Slack, one of the most powerful forces at least on my phone, pulling me in, that showed true user first design thinking and real empathy for this complicated relationship we feel with our phones. In a world where a different organization would be optimizing for maximum engagement of their addicted users, Slack introduced a feature called “Do not disturb,” which, in the their words, is “so you can take a little time to yourself when you need it.”

This is a subtle point, but it takes a lot to recognize that people, and I think most people, are truly feeling this pain and lack of control around their phone usage. This moment reminds me a lot of when Snapchat caught fire. You had an entire population engaging in this extremely prevalent, and rarely questioned behavior, of uploading their lives to be consumed on demand, persistently, by those around them, and along comes an entrepreneur who represents a reaction to this built up, partially afflictive, state of the world, by making everything disappear…ephemerality in the face of permanent and public. I believe there is an equal sized opportunity to react to pent up anxiety around our truly persistent relationship with our phones…and I’m interested in who will come along to help ease the distress.

You might ask yourself, well, as a founder of an app that cares about user engagement, and sessions per day, days per week…how do I reconcile this awareness with our decisions as a company…and I think I land where Slack landed as well…which is to focus on the value of the information that we are providing to our users, and to strive to make every session conscious, and thoughtful, and about something more than the pull, and the stat, and the business level optimization…and where possible, to make decisions that hold empathy for this complexity that comes with adding to people’s lives in a way that also may be detracting…over the long run I think this is the right thing to do, and also likely good for business.

It’s not an easy topic, and like cigarettes, I believe we will continue to operate in the status quo for quite some time before concrete science and consensus begin to change the broader consciousness around this issue, but it’s one that I think is important to talk about, especially to an audience that is making the decisions on the other end of people’s phones, because it’s we have a responsibility to think along this dimension.

Read Full Post | Make a Comment ( 2 so far )

Wildcard Update: New Card Types, New Search, 3rd Party Apps

Posted on February 9, 2015. Filed under: startups, wildcard |

We’ve got a new Wildcard update out today. A few things to look out for:

Three new card types in Wildcard

1) Stock Cards: You can now search any ticker in Wildcard and get back a beautiful stock card. Try searching YHOO, FB, GOOG, etc. for the latest pricing and market information for stocks you care about.

2) Weather Cards: You can now search for the weather and get back beautiful weather cards for any zip code. Try searching Weather 10014, etc to see the new Weather Card in Wildcard.

3) Image Cards: This is my favorite new card type in Wildcard. Although elusive at the moment, you are going to start to see image cards returned in search results quite frequently in the next few weeks. Wildcard’s image cards are a beautiful way to discover and view images form the web at native speed. For a glimpse of the Image Card navigate to Flickr via the Search bar.

We care about adding new card types to Wildcard because we want you to be able to access all the information of the web at native speed in Wildcard. Hope you enjoy them…more to come in next update.

Vertical Search

In this update, we’ve enabled you to filter down search results into the vertical or type of results you’d like. So if you search for the Grammy’s, these clever filters at the top of your results enable you to drill down into Videos, Shopping, News, etc…so that you are only interacting with results that are relevant to what you are trying to do in Wildcard. We have a HUGE update coming on search which will address relevancy of results, volume of results, and allow you to type ANYTHING into the Wildcard search bar and get back near perfect results…but this design improvement toward vertical specific search is a good first step, and when combined with the bigger search update, I think we’ll be a dangerous and true alternative to google/chrome on your phone… to test vertical specific search, run a couple different searches in the Wildcard search bar.

3rd party applications in the Wildcard Browser

We’ve been exploring the notion of not only cards and content in Wildcard, but actual applications that run inside our browser. The application layer in the Wildcard browser was previously restricted to Wildcard’s Homescreen application, our search application, and publishers/brands homescreen applications. We’ve started to branch out and enable other types of applications to run in the browser. For examples of third party applications running in the Wildcard browser, check out

1) Hacker News: Wildcard is an engineering driven culture and most people here read Hackernews…now you can too without clicking back and forth between annoying blue web links. To try out the Hacker News application in Wildcard, navigate to Hacker News via the Wildcard search bar.

2) Designer News: Wildcard is also a design driven culture and many people here read Designer News…now you can too without clicking back and forth between annoying weblinks…To try out the Designer News application in Wildcard, navigate to Designer News via the Wildcard Search Bar

P.S. We are running a little beta of our IOS App SDK. If you have an IOS app and you’d like to replace links to webpages with native cards in your app let me know and I’ll send you docs. It’s basically blue link in, native card out with a few display options (modal, in line, etc…)…It’s very fucking cool.

Read Full Post | Make a Comment ( None so far )

New School Thinkers, Where Are you at?

Posted on January 7, 2015. Filed under: startups, venture capital, wildcard |

Getting old is an interesting thing in startup land. I realized this a few days ago when Forbes 30 under 30 came out and I could finally tweet my hatred of lists like this without any suggestion of my exclusion as the source…because…well…I am not even eligible anymore. In fact, I haven’t been eligible for 2 years at this point. 32 years old is not grey beard territory, but there is now a very defined generation of founders and thinkers in our community that is after mine…that think and behave differently…that make some of my context and assumptions about the world antiquated and non-contemporary. I am certainly a student of technology and social behavior, and I invest quite a bit in staying up on how things are changing, but it doesn’t change the fact, that I now fall more into the category of experienced and biased, than youthful and “temporally native”…if that phrase makes sense.

Anyway, this post is not really about me getting older…it’s actually about my network (that word sort of makes me puke…especially as a verb) getting older. Networks age…and there are some amazing things about this reality, and some shitty things about this reality. The amazing thing about my now-aging network, is that the “kids” i grew up with in startupland, continue to accrue more and more responsibility, more and more influence, and it’s good to be friends and close with people who are leading meaningful companies or initiatives within those companies…my network has many more “decision makers” at increasingly important places than it did when I was 24 and just beginning in this world. The down side of my aging network is that it is harder to find quality thought coming from a super contemporary place…originating in fresh data that is not biased by historical events or previous knowledge. Said another way…most of my “go to” people that I’ll grab a coffee with just to talk about the world and what’s interesting don’t reside within the 22-26 year old, “temporally native” crowd. We have a great little pocket of folks like this here at WildcardMax, and Ryan, and Connor (the Wild Kids if you will) remind me a lot of myself when I started out in startupland…and their thinking inspires and influences me daily…but lately I’ve been feeling like I’d like to invest more heavily in extending my network into this age group…

In my old age, i’ve become very protective of my time…I won’t take or request a meeting with someone new…ever…if there isn’t an explicit purpose for doing so. When I was 24 and someone interesting on twitter says “hey, want to grab a coffee” I think more often then not the answer was yes…and I’d similarly claw to get as many coffees with people who I thought were impressive…with no specific agenda other than “i want to know this person.”

I mentioned previously that my mantra for 2015 is “Effort,” and that mantra I think applies to many different realms…one of which I’ve decided is “building closer relationships with the new kids on the block.” I’m going to try to hang with a few folks from the 22-26 year old crowd every week…no agenda…just talk about the world and what’s happening…and develop some new thought partners to round out my “go to” group. I don’t know that I have a ton to offer…I don’t really want this to be “career advice” or “business pitch” or “job interview” type stuff…I guess I just offer my genuine interest and ideas and willingness to learn and explore any area that matters with anyone smart who wants to spend an hour doing so.

So if you’re part of this “temporally native” crowd and would like to waste an hour with me, I’ve carved out time and would love to do it. Just send me an email to with a link to your online presence so I can do a little research and figure out if we are going to think about interesting things together…

Read Full Post | Make a Comment ( 2 so far )

This isn’t the death of the web, it’s the birth of the native web

Posted on November 25, 2014. Filed under: startups, venture capital, wildcard |

Something interesting happened a few days after we launched Wildcard last week. We released the first ever “native card browser” on November 13th, a serious departure from traditional HTML based web browsers, and 4 days later the Wall Street Journal published an article entitled “The Web is Dying; Apps are Killing it.” This is by no means the first time this concept has been suggested, but the debate flared up in the wake of our launch, with a wave of follow on posts discussing the future of the web and its health as it relates to a mobile first world. I can’t say that Wildcard is responsible for provoking this instantiation of the debate, but I do think our product and message reached the community of folks who are thinking about the future of the web, and the timing/language that flowed through the posts I read suggests to me that Wildcard was present in people’s minds during the conversation.

Two years ago when we started building Wildcard, the debate of native vs web was in a very different place. It was not a forgone conclusion that almost 90% of our internet consumption in 2014 would occur within apps, and a large contingent of “web purists” still held hope that HTML5 would win out over native. At the time we bet on the native ecosystem, but aspired to bring some of the most important properties from the web (like discoverability and sharing/linking) into this new reality. We thought of cards as the native analog to webpages, and didn’t aspire to kill the web, but rather to modernize it into what was clearly a superior user experience on mobile (app/native technology).

I was pleased to see in the most recent wave of this discussion, a general acceptance or recognition that in today’s mobile era, the web as we know it, is pushing down stack to a more infrastructural position that is powering new, native interfaces that are easier to interact with on mobile. I liked the supposition that just because users are interacting with the information from the web in a different interface or format, that does not mean that the web is dead or dying…to me this arc read more like an evolution than than an extinction.

I have largely tried to stay out of this debate, mostly because I am sensitive to my lack of historical context associated with the development and emergence of the desktop web. There are so many smart people who lived through it, who are intimately familiar with it’s definition, properties, and ideals…and my study of the internet really only began in 2005…I feel really confident building what I hope the native web or native internet becomes…but less comfortable pontificating on how that future does or does not jive with the past.

So this is all to say, I was pleased to see thoughtful posts like this and this pushing forward a more flexible and updated definition of “the web” and I hope that Wildcard can play a small part in defining an interaction paradigm that recognizes today’s hardware and context while delivering on some of the things we lost in the migration from the web as we knew it to this more modern, native consumptive pattern.

For ease, i’ve pasted a bunch of the media from this latest conversation:

“The Web is Dying, Apps are Killing It” – WSJ, Chris Mims

“Follow Up: The Soft Bigotry of Low Expectations for the Web” – WSJ, Chris Mims

“The web is alive and well” — Quartz, Zach Seward

“Native Apps Are Part of the Web” — Daring Fireball, John Gruber

“The Web, Still Dying After All These Years” — MG Siegler

“Is the Web Dying, Killed Off by Mobile Apps? It’s Complicated” – GigaOm, Matt Ingram

“The Web is Dying! Wait, How Are You Reading This?” – Slate, Will Oremus

“Rumors of the Internet’s death have been greatly exaggerated” – Daily Dot, Ben Branstetter

Read Full Post | Make a Comment ( 1 so far )

Not Every Datapoint Demands an Insight

Posted on October 28, 2014. Filed under: startups, venture capital |

I read a headline in my twitterfeed just now that said something to the effect of “why twitter’s stock price is trading below it’s ipo value again.” Out of 100 tweets or so i consumed, that information triggered my “signal detector” which is the little voice in my head that says “this new thing might mean something / change something in our overall view of the world.” That detector goes off in my head, conciously…about 25 times a day…it can be triggered by a piece of news, a conversation, or even the expression or aggregate expressions of the strangers that i pass by on the street on my morning walk to work. I think one of the things that makes me weird…that attracts me to weird problems…and potentially isolates me from regular folks is that my detector tends to go off by a set of events and information that are really different than what most people pay attention to. I don’t know why, but it’s always been that way.

As a result, my process of listening to and addressing the information that sets off that trigger is really different from, say, what an equity research analyst or a private equity partner might have. Let’s take the case of that tweet from earlier…my process for analyzing that event was too go to Yahoo Finance. look at the one year stock chart of Twitter, spend about 20 seconds asking myself “is this different from what I expected?” or put another way “does this conflict with my current world view” and if the answer is not “yes, this is unusual”…than i x out of the tab, keep rolling, and don’t think about it anymore…and that’s exactly what I did in the case of that tweet. Now that doesn’t mean that datapoint is gone…it may reemerge sometime in the future, but I never try to force my way to an insight around things that trigger my “signal detector.” I feel like an analyst would sit down, look at this new event, and apply a process that would not be complete until some conclusion was reached…insistent that every new piece of info is some sort of “update to his worldview” but that’s not the way I think about this stuff…most information…i just try to let it wash over me…run somewhere in the background, and then wait for a signal that conflicts with it all to induce an insight or understanding of what’s going on…it’s kind of the opposite of a linear analysis and i think it makes room for a wider top of the funnel when it comes to the types of things that trigger my “signal detector”…

Happy Tuesday

Read Full Post | Make a Comment ( None so far )

Creating Fast Moments

Posted on September 10, 2014. Filed under: startups, venture capital, wildcard |

I live for fast moments. The sprint to recruit and close a superstar…that’s a fast moment. The intensity of raising capital…that’s a fast moment…the breakthrough product idea that changes everything…and the week long sprint to get it into production…those are fast moments in the life of a startup. These fast moments are the days and weeks when everyone in the office shares an elevated heartbeat…anticipation becomes palpable and you can begin to vaguely make out the place that was talked about but previously beyond the horizon…

If I go too many days in a row without a fast moment…I start to feel it. Before I think it…before I analyze it…I can literally feel the slowness in a period of time. I get grumpy without being able to articulate why…I get unproductive without being able to articulate why…I just feel the slowness and it literally interrupts whatever I am doing and says “hey…wake the fuck up…we’re not going fast anymore.” It usually takes me about two or three days of unpleasant feeling to realize what’s happening and then I sit down with a stack of white computer paper…i map out everything that is happening both internally at the company and externally in our market…I find the 3 or 4 fast moments that are waiting around the corner for us…and I steer directly into them.

When I was younger, running Hyperpublic…I would literally try to create these fast moments myself… “not moving fast enough? I’m going to go out there into the world…hunt a giant fucking animal…whatever that might mean…and I’m not coming back until I’ve got a carcass to drop in the middle of the office floor.” That kind of works…but there are many more fast moments than a CEO can create on his or her own. We have such a talented group of people building Wildcard…on any given day…any given person is capable of changing the game…now when I map on that stack of white paper…i’m just trying to figure out who is coming up to bat this inning and what type of pitch represents their next fast moment.

The reality is it’s a 9 inning game…in a 162 game season…and some innings are gonna be slow…sometimes we’re going to have to grind out a 0-0 game until the bottom of the 9th…and sometimes we’re going to score 8 runs in the very first inning…I guess I should be more accepting of the slow moments in the season…but I can’t help it…I just love fast moments…and I’m gonna chase them down until the day I stop playing this game.

Read Full Post | Make a Comment ( 2 so far )

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

Read Full Post | Make a Comment ( 1 so far )

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:

Read Full Post | Make a Comment ( None so far )

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.

Read Full Post | Make a Comment ( 1 so far )

Women at Wildcard

Posted on January 8, 2014. Filed under: startups, venture capital, wildcard |

I’ve wanted to write this post for a long time…and every time i sat down to do it…it just didn’t come out right. If you’ve read this blog for a while, you know that I care about the people on our team more than just about any other dimension of Wildcard…more than I care about product…more than I care about fundraising…team is everything. It was true it Hyperpublic and it’s true now. When Hyperpublic was acquired by GRPN, we were 10 people…9 engineers and me…1 first generation immigrant and 9 born Americans…8 caucasions, 1 Asian, 1 African American…1 profesional musician, 1 chef, 1 billiards master, 1 former professor, 1 outdoors enthusiast, 1 fashion efficianado, 1 college drop out, 1 improv master, 1 son of a preacher man, 1 semi-manic tech blogger…and 10 MEN…we had such an amazing and diverse group along so many different axis…except gender…where we were shockingly homogenous.

At Wildcard we are now 10 people as well…6 engineers, 2 designers, 1 ops, and me…guess how many women? Not for a lack of interest and not for a lack of effort…but still the facts are the facts. I have a handful of close female friends in the tech community, and a smaller handful of close female friends in the engineering community in NYC…and over the past few years I have listened carefully as they’ve shared their views on building a multi-gender culture into your startup. Here are a few “near quotes” that I’ve heard that have stuck with me and inform the way we make decisions at Wildcard.

1) “if you get to be too big without bringing on a female employee, it get’s much harder to do so down the road.” The spirit behind this observation is that it can be intimidating for a potential recruit to be “the only woman” on a team of 15 males…obviously that intimidation factor grows when you replace the number 15 with 20, 30, and so on.

2) “It isn’t enough simply to have female employees at your company. You need to have female employees in leadership roles at the company.” The spirit behind this thought is that young ambitious women want to see that your organization is a place where they have the ability to grow and advance into influential roles within the company. If the leadership in the company is uniformally male, that does not set a tone of opportunity within the company.

3) “you’re brand of being badass engineers is too unwelcoming and does not appeal to the female psyche in the same way that it does the male psyche. Consider modifying your tone from working amongst the most badass engineers to working amongst the most intelligent people in NYC. There is nothing wrong with communicating the pedigree and ability of your team, but do it in a more gender neutral way.” I didn’t realize that “badass” was a more male value…but I can see how that is sort of lazy language to articulate how special the human beings at our company are.

4) “Women don’t want to be hired simply because they are women. Nobody wants to feel like the token girl that got the job because your startup needed a woman.” This one is so important because I think I and many startups have fallen victim to the reality that it is difficult to source female candidates for open positions…but when you advertise that you are looking to or excited about bringing that diversity into your culture you set a tone that can unintentionally trigger the above sensitivity. In fact, one of the very reasons for writing this long, verbose post is to say “I’m listening…i’ve been paying attention…i understand many of the gender dynamics that are at play in the startup ecosystem. I don’t have all the answers, but I care…and maybe this post will lead to a change in the complexion of our team and maybe it won’t…but I’ve BEEN listening and I don’t know what else to do to address it other than write out where I am in the process of figuring out how to build the best team of men and women and New York City.

So yea, I know there are more dynamics at play than the ones I’ve articulated, and in some sense I’ve condensed hours of conversation down into a few bullet points, but at least this on paper…this is how I’m thinking about gender at Wildcard…and my and our actions will be in response to these shared observations and any more that people would be willing to share in the comments of this post. Been too frustrated with this challenge for too long not to work through it head on.

Read Full Post | Make a Comment ( 2 so far )

« Previous Entries


    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)


    Subscribe Via RSS

    • Subscribe with Bloglines
    • Add your feed to Newsburst from CNET
    • Subscribe in Google Reader
    • Add to My Yahoo!
    • Subscribe in NewsGator Online
    • The latest comments to all posts in RSS


Liked it here?
Why not try sites on the blogroll...