There is a controversial interview with Paul Graham floating around and I'm left to wonder why we're still paying attention to guys like him. He is accused by people of being, at best, oblivious and at worst, sexist. I've never sat down with the guy, so I can't speak to that, but I'm tired of hearing about the same voices over and over again when I'm not even sure they're relevant.
Why give more airtime to someone whose peak of influence, and perhaps success, is clearly behind him--especially to talk about topics where he clearly isn't adding value to the conversation. Every time he opens his mouth about founder diversity, he seems completely out of his league to address the topic. I want to hear Paul Graham's thoughts on gender equality and inclusive participation in the Valley as much as I want to hearCharlton Heston's thoughts on gun control.
"God knows what you would do to get 13 year old girls interested in computers. I would have to stop and think about that," he offers.
Well, maybe he should do that... Stop--AND think. As a guy, I know how hard it is for us to do either of those things, let alone do both at the same time. However, in this moment, I think one's career in venture capital depends on changing your perspective.
The biggest question I think VC's face right now is whether or not, in the future, the best founders will look and act like the best founders of the past. Will they come from the same places as today's industry leaders, or from the far corners of the earth and from underrepresented groups? The world is getting flatter than ever before and the white American male is exerting less and less influence over it each day.
If you are a venture capital investor and you're not preparing yourself to succeed in a more diverse ecosystem of entrepreneurs, you're just going to get left behind.
Considering the myopia at the top, it's not surprising that turning point may have already happened for YCombinator. YC's best investing days may be behind it.
YCombinator had a great run from 2007 through early 2009 investing at a time when there weren't nearly as many seed funds and accelerators as there are now. They picked up Airbnb, Heroku and Dropbox.
Since Airbnb, however, it feels like not only is YC missing another billion dollar plus home run, but the percent of companies worth $40 million (a standard YC has used in the press), either by financing or exit, seems low. I'm thinking maybe I found about three dozen companies worth that much in the nearly 400 companies that have been through YC since Airbnb. That's less than 10%. The classes got too big and quality was diluted because, by PG's own admission, YC "grew too fast."
You could argue that the recent companies are too early, so I'll take that challenge and compare it with my own portfolio. Given that they do $17-20k per founder across 350+ companies, we're in the ballpark of the amount of money we're invested--just south of $10mm.
My own track record as a VC across First Round Capital and Brooklyn Bridge Ventures actually starts in January of 2010, *after* the Airbnb class of Winter 2009. I've closed on about 20 early stage investments and, by comparison, 5 of my investments are now worth $40 million or more either via financing or exit (with three more over $25 million). That's 25%... a far higher rate than YC has appeared to have done since then. My total valuation multiple across that span is nearly 4x and the return rate is up over 110% IRR. The initial base of capital has already been returned in those investments, so it's not a made up return based on just paper gains either.
Most relevant to this conversation, though, is that I didn't do it by only funding only hacker dudes in the Valley:
- Nine of my twenty investments have female founders or co-founders--nearly 50%.
- All of the companies but one were funded in NYC, with the other in Boston.
- Of the 20 teams, only half count an engineer as a founder or co-founder.
A couple of years ago, I went to a networking event sponsored by a top tier VC firm. It was held at a trendy Lower East Side bar where the price of the drinks made it the kind of place that a typical NYC entrepreneur would never actually go. The invitees were a who's who of the NYC tech scene--all the most visible folks.
It was exactly how you'd imagine a venture firm to throw a party. You could see that conversation happening:
"Hey, let's reach out to the community. What's the coolest place to go to? Let's invite all the important venture and startup people people we know of--and don't forget to throw in a few women, too."
You wind up a far cry from Shake Shack when that happens, I'll tell you that.
That's when I realized what separates how the next generation of successful VCs will look at the world.
That party was a bet that the best future opportunities would come from an insider network of people already connected to the establishment--that getting the next Google or Facebook meant connecting to the people "in here".
I'm certain, however, that the more interesting stuff is going on "out there". I believe that the most successful companies that I will get to work with over the course of my career will come from people not currently connected to the insider ecosystem, and from people who don't look like yesterday's notable founders. I'm making a huge bet on the people "out there" because they have new ways of looking at things, new approaches to running businesses and are tackling problems being felt most deeply by the people outside the inner circles.
If I'm going to be successful in that world, I better damn well have a view on how to make the ecosystem more inclusive. I need to watch my style to make sure I appear approachable versus authoritative. I need to learn from my mistakes where I may not have done all I could to make people feel welcome and respected--and surely I've made 'em.
My brand needs to be one of a dutiful civil servant in a welcoming city rather than what I see from certain investors--acting like royalty in a place that investors believe is the only one that matters in the world.
The media needs to do it's part, too. Let's stop paying so much attention to what old voices are saying about the establishment, and instead strive to seek new voices and new perspectives. Otherwise, we risk signaling to future generations that these are the people in charge and that nothing is going to change.
We need to send a strong, clear message to that 13 year old girl, the 13 year old black kid, and the 13 year old growing up outside of anywhere anyone thought to call a venture hotbed to tell them that they can be successful and that they'll get the help they need from openminded professionals.
The other day, I looked at some real estate on behalf of one of my portfolio companies.
The owner sent me this...
Maybe I just don't have enough imagination or lack the requisite architecture degree. At least it's better than showing an actual picture of what the office looks like now, after the last tenant trashed the place on their way out. Or, if they didn't trash it, they subdivided it for a colony of bees and painted it what can best be described as neon beige.
This is what Floored does, with a turnaround time of just a few hours...
If you don't understand the value of that to anyone who sells space, you probably also read the directions on toothpaste.
But it's not just selling space--it's what goes inside the space, too. Floored's technology isn't just going to help you imagine your new office or new home, but walk through and buy all the furniture, paint, flooring, etc that goes into it.
That's exciting--and I'm glad RRE and Greycroft felt the same way. They just led a $5m+ seed round in the company. It's a nice bump for my seed portfolio (I invested about a year ago) and a big win for the company, which is already on a serious revenue ramp.
Congrats Team Floored!
We, as a society, put in place structures like government and big corporations largely as an organizational efficiency. By pooling our resources and centralizing control, theoretically, we can more effectively do things like police neighborhoods, manufacture things and defend our borders. Still, these entities are supposed to work for us and in our best interest.
Not surprisingly, these entities become quite powerful over time--and not just the entities, but the people working at them. When technology comes along and improves the way we organize, making some of these structures less efficient, or even wholly unnecessary, not surprisingly, they don't go quietly. Because of their power and influence, they also know how to protect themselves through legal and regulatory methods quite well.
They're all part of the same machine--record labels, cable companies, drug companies, credit card companies, telecom companies, taxi commissions, hotel lobbies, defense contractors, prisons, big pharma, tobacco, big food, etc. They got bigger than we ever needed them to be and the more that we can seamlessly connect to each other, understand each other, and mobilize our numbers, the less we need them. Still, expect them to dig in their heels.
Peer to peer lending, community supported agriculture, ride sharing, house sharing, fans supporting artists directly, bike share--even the growth of healthy lifestyle activities like yoga and running--it's not just about new business models.
It's a war.
I mean, don't you feel like we're losing a battle when Pepsi has a bigger presense in our schools than phys ed?
This is us collectively flipping off those institutions and saying, "Fuck you, we'll take care of ourselves."
And it's only begun.
How about truly local enterprise zones where chain stores that take more money out of communities than they put in are either outright banned or must keep profits reinvested in the community? It's not just about supporting small business--it's about profit staying with your neighbor who owns the coffee shop and then spends it back in your community.
What about programs like Defy Ventures that turn convicts into entrepreneurs? Wouldn't it be better if someone gave you a shot to employ your peers when you got out of prison than to return to a life of crime? Just because the government labels you as the worst thing you ever did doesn't mean the rest of the world does--and your local network should care more about what you do than what you did.
When do we get a farm on every rooftop and in every school? Instead of shipping Twinkies across the country to put into our kids, let's have them grow veggies right on top of the school. Well, it's coming.
Forget cord cutting. How about tower cutting? Take the network out of the network and enable truly peer to peer communications. It's coming.
How about voting off your handset--for everything? There's a zoning law being written about your own street. You'll get a notification on your phone and get to weigh in, and influence the way your neighborhood is changing.
If you lived during the Industrial Revolution, the world was completely reinvented during your lifetime. I feel like we're on the verge of reinventing society--that the shifts we see in power are only the beginning. Peer coordination and network of individuals are real. It's going to result in a lot more than just photosharing.
Powerful structures are crumbling and it's bigger than even we can imagine. I'm psyched to be a part of it.
Helping Big Get Small - Why I invested in Orchard's effort to help institutions participate in online lending
Over the last few years, we've seen a lot of technologies start out in the consumer world and "infect" the enterprise. This creates a large opportunity for companies who see consumer trends and understand enterprises well enough figure out what it will take to get them to participate. This is essentially the bet that Box has made relative to Dropbox. Early on, there were lots of reasons Dropbox didn't work for companies that were more than your four person startup, and that's what Box focused on.
Online lending, specifically peer to peer, is one of those markets. The market has exploded on the consumer side, with companies like Prosper and Lending Club seeing huge successes matching lenders and borrowers. It's been a huge win for consumers, too--on both sides. You can borrow money at much better rates than credit cards or payday lending, and many investors on the platform are seeing high single digit or even double digit returns on their money with low default rates.
It was only a matter of time before larger money managers started looking at these platforms and finding their returns attractive. Funds are even being raised to take advantage of these opportunities--but it isn't exactly easy for an institutional player to go lending out $25 at a time on a peer to peer platform.
Sure, these platforms have some basic tools for you to put more money to work--but they don't have the depth and complexity that sophisticated asset managers need to manage a portfolio, especially when compared to what's available in other asset classes. There's a need for secondary markets, which also would require third party pricing, ratings, etc that would help make this asset class more attractive to institutions.
It's not unlike what happened in ad tech. The more tools that got created to allow sophisticated, targeted buys and various types of repackaging to allow thoughtful media management, the more buyers found a way to make it work for them. That's why it's not surprising that the team at Orchard, which just announced a $2.7 million dollar round, has roots in the ad tech world. In addition to having strong chops in the data and credit risk areas, this team helped built AdMeld into what became an important component in the DoubleClick Ad Exchange. They get marketplaces and now they're making these lending marketplaces work for institutional players.
I'm excited to have made an investment through Brooklyn Bridge Ventures alongside Spark and Canaan in their initial round. This has a lot of components of the kind of deal I look for, even though it's a larger initial round than I'm used to participating in. It has a strong team that has a unique perspective on their space, and the background to execute on it. It's still super early, despite the size of the raise--they hadn't raised anything before this and are working to build out their product offering. Plus, I was early to committing--the first fund to say yes and offer a number. That's important to me as I try to establish myself as someone willing to plant that flag even if you don't have any other supporters yet. I understand how frustrating it can be when the first question a VC asks you is who else is in. I might be wrong, but you can't knock me for lack of conviction. This is a team that I believe in and a market I'm excited to see develop. Good luck to Matt, Jonathan, Phill, David and Angela.
*Small note: This is the sixth of twelve teams that I've backed out of Brooklyn Bridge Ventures that I've backed that had a female co-founder. I'm seeing way more mixed teams and I'm excited about the diversity of perspective that I'm seeing in these founding teams.
When governments go through leadership changes, it is generally expected that their whole staff gets replaced. It's a bit weird to comprehend for those on the outside. When a new CEO for a company is hired, you might change out a few people, but you wouldn't replace all the key folks. The turnover would be detrimental to company culture.
Same goes for a baseball team. You wouldn't hire a new GM and just immediately get rid of your All-Star players.
But, this is government. It's not the real world. :)
That means that just about every position is going to be up for grabs, including the newly created Chief Digital Officer position held by Rachel Haot. I was asked who I thought should get it, and my first response was, "So, what do you want that person to do?" Obviously, each person is going to handle their job in their own way, but I thought it would be useful to go back to the first press release describing the job.
It says the job is about:
"...improving communication with residents and businesses by enhancing government transparency and working closely with digital media. Sterne will work closely with the City’s Department of Information Technology and Telecommunications as well as with individual City agencies and stakeholders to ensure consistency and accessibility of information. This is the first time the City has hired someone to streamline digital media communications across a broad array of City agencies. Sterne is tasked with helping to make NYC.gov more user-friendly, ensuring that agencies integrate social media opportunities and serving as an advocate for the digital media industry in New York City."
On one hand, it sounds a bit like PR... mentions of communications, information, advocacy, etc. I'd contend, though, that it's actually a product manager job.
Think about it...
- Communicates with stakeholders--both internal and external
- Works with tech
- Insures consistency across products
- Makes the user experience on the web better
- Keeper of the vision of the digital experience that is the city government
That's what product managers do. They figure out what everyone needs by talking to everyone, and then enables both business and technical stakeholders to work together--since, as Office Space taught us, you can't have the customers talking directly to the engineers.
Plus, product managers excel at getting other people to work on things that are not their direct reports. They don't have their own staffs, and tech doesn't report to them. They're responsible for a product, but they have to work collaboratively. That feels a lot like what someone working to coordinate the efforts of multiple city departments would have to do.
Speaking of multiple city departments, the role currently sits within the Mayor's Office of Media and Entertainment, but that's probably not exactly the right place for it. It should probably report to both MOME and DOITT, the city's tech arm that actually builds and maintains the tech that the goverment users, at the same time. That's usually where product sits--with dotted lines to both the marketing/business and technology functions of a company.
So who should it be?
Here's a name for you: Jenn Vargas.
She's a product manager who is also a designer and developer. She's from the NYC area (Bayonne, NJ) and she went to Cornell--the school at the heart of NYC's tech education expansion. She spent time on the west coast, but then came back to work at standout NYC tech companies like Etsy and Birchbox. Jenn has also taught at General Assembly--and if you're going to get government online, you're definitely going to have to do some teaching.
Plus, she fits my two criteria for the job:
1) She's awesome.
2) She probably doesn't want the job. (In fact, she has no idea that I'm writing this.)
This is the kind of job that would come with a ton of visibility so there are going to be a bunch of people who would want it. That's exactly what you don't want--someone who wants the job to make themselves visible.
You would best be served to have someone who would absolutely dread getting dragged to press conferences and would rather just work to make a product great. We've come a long way with our nice new website and better social presence, but there's lots of work still to do. Bandwidth is at third world levels and open wifi is rare, to pick out an easy one.
Obviously, we'd need to consider a slate of candidates--and if this is truly a position that involves transparency, why not crowdsource some leeds? Bill DeBlasio should just post a tweet asking for suggestions. Get all the minds working! If anything, that was a knock on the Bloomberg administration--doing whatever they wanted behind closed doors.
If you're going to break from politics as usual, why not have an in depth, public discussion about the role? Heck, post it as a Quora question.
Who should be the next Chief Digital Officer of New York City?