This blog represents my own views, not those of my employer, Brooklyn Bridge Ventures.

Do not pitch me a story or book review for me to write about. This is my personal blog. For more info on that, see this post.


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10 Things I've Learned in 10 years of Blogging

1. The attention you get from saying something intelligent and thoughtful comes slower and in smaller amounts than the attention you get from being controversial, but it lasts longer, compounding over time.  

2. Focus on the topics you care about and that you find interesting, not what everyone else is talking about.

3. Take a position and stand for something, but be open to learning from others.  

4. The less words you need to make a point, the better.  It's also really hard to stop writing when you're passionate about something.

5. You don't have to talk about your personal life for people to get to know who you are--let your personal style shine through your professional discourse.  

6. Try to make one point at a time.

7. Nuance is lost on crowds.

8. You can rarely predict what other people will find interesting about what you have to say--and it's never the things you say to try to be interesting.  

9. A small group of people will spite you for thinking you have anything to say whatsoever.  Listen to what they have to say, check yourself, and then ignore them.

10. Take all the time in the world to go from someone who asks a lot of questions to someone who makes a lot of statements.  

The Rules of Inclusion 

I was talking to a female engineer turned product manager last week about her experience as one of the few women at a hackathon.  While she didn't experience anything particularly negative, she still didn't feel particularly welcome.  When you're one of only a few people who look like you in a place, if the event is a free-for-all, it's tough to break into new groups and connect with strangers.  That's when I realized that there's a lot more that goes into making various groups feel included than just inviting them.

Specifically, there are some event organizers that go out of their way to make everyone in a room feel comfortable.  At Brooklyn Beta, for example, there was a speaker that I thought really muddled through their presentation.  It was awkward at best.  I kept checking Twitter to see if I was the only one that felt that way (and maybe I was) but there wasn't even a peep.  It blew my mind.  I've seen better presentations get ripped to shreds with snark on Twitter, yet there wasn't even a peep.  


Because the organizers set the tone early.  When they introduced the speakers they paid extra attention to mention when speakers were nervous, or apprehensive, or when they didn't come out to speak that often.  The said that DNA of the conference was to be welcoming and supportive and immediately set expectations for what was and wasn't done there.  In the face of that, it felt completely inappropriate to comment negatively.  (I mean, it should feel that way anyway, but that's not always the case.)

There are other ways of making people feel supported.  At the New York Tech Meetup, you're encouraged to speak with the people sitting around you.  No matter who you are, if you attend, someone is going to speak with you.  What if, at the hackathon this woman had attended, the organizers had just said, "And now is the time for introducing yourself to the person next to you."  Even better, what if there was a requirement on your team to bring a stranger onto your team?

Alcohol also plays a big part to making people feel included or excluded.  First, and we don't talk about this too often, but not everyone drinks.  If it feels like the key participating socially in an event is drinking, you're going to get people who aren't going to feel like it's ok to join in.  I don't drink at all, and it never stops me from coming out and going to bars, but I've definitely heard from others that's not an environment they like being in.  

Secondarily, people sometimes (often) say ridiculous things when they drink--and it gets them into situations where they feel like the point of being there is to make friends or make dates.  Put a bunch of twenty somethings in a bar, liquor them up, and dim the lights, and you don't exactly create the right environment for making one of the five women in the room feel like they're going to get taken seriously

So what if you came up with a serious of rules.

Sometimes, I go to an event and they announce that they follow Chatham House rules on what is sharable:

"When a meeting, or part thereof, is held under the Chatham House Rule, participants are free to use the information received, but neither the identity nor the affiliation of the speaker(s), nor that of any other participant, may be revealed."

This way, everyone knows what the deal is.

What if we had a serious of rules where the event could announce beforehand and during that "We're following the Rules of Inclusion".  What would they be?  How could they change the environment to make everyone feel welcome.

I'd suggest a few things:

  1. From the beginning, the event will be marketed to in some way to give diverse groups of people the opportunity to participate--which might include sending it out to certain groups ahead of the onslaught of young white dude mailing lists.  In my mind, this is different than just counting.  It's being a little more thoughtful than first come, first serve, but stopping short of quotas.
  2. Have attendees agree to a code of conduct around respect of speakers and fellow attendees, and announce what that code is--and extend it to social media participation.
  3. Clearly identify who the organizers of the event are, and suggest that if anyone feels uncomfortable in any way, or even if they just want help being introduced to people, that they can reach out to those people.  Maybe they could be wearing event t-shirts or something.
  4. Create a networking opportunity that doesn't involve alcohol or is more conscious of the environment.  Perhaps picking venues that aren't just bars, but that might have separate sections--tables meant for discussion or something.  Maybe the speakers will be sitting in a certain area that is better lit, quieter, etc.  People might tend to act up less around speakers--so in a way you'd be creating a kind of safe area without making people feel like it's the "boring area".  

What else would an event need to work off the the "Rules of Inclusion"?


Fundraising Done...and Now for the Real Work

I'm announcing two things today.

First, I've finished raising the first Brooklyn Bridge Ventures fund--tallying $8.3 million.  This is what I set out to do just about two years ago when I first broke out on my own and started raising, so I'm thrilled to say that it has finally happened.

I'm not going to do too much of a victory lap, though, because it bugs me a little when startups do it, and I'm a startup, too.  Fundraising is not the goal, it's the means to an end. 

One of the reasons why I'm announcing at all is because I realized that it had been a while since I said anything about the progress of the fund--and if you're an industry person, you might have started wondering.  Was the fund enough to keep me going?  How many more investments could I do?  How where things going?  These are things that other VCs think about, but founders who come to pitch don't think about too much.

That's also why I'm finally launching a real website at  When you blog, tweet, Instagram, etc., as a VC, sometimes your own website becomes an afterthought.  It's important, though, to summerize what you're all about and the deals you've done so people get a sense of what to send you and how you've done.  This site was my holiday project and I had a little fun with it.

So there ya go.  Thanks to everyone who supported me along the way, especially to the awesome team at First Round who gave me the opportunity to build a track record, to learn how to be a board member, how to leverage the help you provide portfolio companies, and figure out how much I wanted to avoid long weekly partner meetings.  :)

Disconnected Home

With the multi-billion dollar acquisition of Nest, people are talking a lot these days about the connected home.  It came up at the Canary board meeting the other day.  Canary is the world's most easy to install home security device, connecting to its homeowners via the cloud.  

As the lead investor in the company's seed round, you'd think I'd be really bullish about the connected home, especially after their record Indiegogo pre-sale netted them almost $2 million in purchases.  

I'm not. 

In fact, I think the term is kind of weird.

"Connected Home"

I don't know about you, but my home has been connected for quite a while now--to the internet.  More and more of the things in it are connected to the internet as well--but calling it a "connected home" is kind of a misnomer.  There's this idea of a centralized system interfacing with all the items in my apartment and a hub of some sort where I "manage" them, but if you look at the way technology has trended, it's not clear to me that makes sense at all.

Almost ten years ago, I bought a Netgear MP101 to take songs from my home computer and stream them to other locations in my house.  I bought a couple of these to wire my place for music.  Recently, I threw them out after years of neglect.  

I've been getting effectively that same service because there's a web connected device in every room, and I stream.  Between my phone, my iPad and my Chromecast enabled TV, I'm pretty covered when it comes to having music everywhere.  There's no need for the devices to talk to each other across my house, because they're all connected to the web, and to the services that I stream from.  

In fact, my phone has become a sort of universal remote for everything.  When I walk into my house and want to watch or listen to something, I turn on my TV and then navigate through my options on the phone, sending them to the TV via Chromecast.

I don't need a centralized server in my house.  That's what the web is.  As long as something connects to wifi, I can get an app for it to do what I need.  The trend isn't connecting within the home--it's a trend of physical devices being made better because they're connected to the cloud.  

One way to think about it is to imagine whether or not this device needs a better screen.  Screens help me navigate through choices and visualize data.  There are some things, like my refrigerator, that don't really need those things unless they can tell me what's inside.  I don't need or want a screen for my fridge if it has anything to do with being cold or making ice.  That seems to add unnecessary complication on top of a function that fridges have been performing quite well for decades.  

Start telling me what I have in there, which would help me shop, and now you're talking screens, choices, and data that might be useful--in a fridge app, not transmitting to a central place.  

That's why it's not surprising that music and TV were some of the first things in the home to get internet connected.  Anything whose output is digital is going to have a lot more range of choice and needs for display than nobs and dials could ever get you.

Still, they don't need centralization.  My entertainment experience isn't centralizing along the lines of my home server--it's aligning along catalogs like Netflix that are available across any device.  

If you're building cloud connected products, I'd assume the user doesn't have anything connected to anything else, nor do they want to, and let a series of standalone apps make your product better.  Netflix phone and tablet apps work just fine for someone who doesn't have a "connected" media center at home.

To me, this echoes the social network trend where everyone swore that you'd need something central to manage all your social profiles.  We got services like Friendfeed to be our "connected home" in a social world, but they didn't take.  People were perfectly content having different social products for different activities--sharing photos, running, connecting professionally, sending secret messages to each other, and voice calls--and we didn't need or want a "hub" for them.  

If anything "hubs" run counter to everything we've seen from the development of the internet, which moves us away from hubs, not towards them.  We don't use the Yahoo! home page as our first screen on the web anymore and so it's not clear to me that Nest is today's Yahoo! home in the home.  

Will Professionals Confide in an Secure Messaging App?

Yesterday, as a joke, I sent Josh Kopelman the kind of text that would probably make him cringe if I had sent it by e-mail.  (No, it wasn't a pic of any kind--just a joke.)

Knowing Josh, he still probably cringed, but he cringed a little bit less because we were both using Confide--a sort of Snapchat for professionals.  There's no lasting record of me ever having sent that note and he only got to look at it once before it disappeared.

There are a whole bunch of questions around the concept, but it does feel very relevant.  Just last week, Chris Christie seems to have cost himself a shot at 2016 because of his staff's retaliatory #trafficgate e-mails.  Had it been sent with an app like Confide, Christie could have caused all the traffic pileups he wanted without leaving a trace.

Confide brings up a lot of thoughtful questions worth thinking about.

Will the company leverage its press momentum and download pace to raise a bunch of money at a ridiculous valuation before we really know anything about it's uptake and stickiness?


That was easy.

Seriously, though...  What are the chances of success for a company like this?

Privacy, or more specifically, ephemerality, is an interesting place to start--but I don't see it as a way to gain mass adoption.  Most people just don't see the chance of private conversations being made public as a big risk--whether that's a careless approach or not.  We've had business e-mail for twenty plus years and there hasn't been a secure e-mail system that has gained traction yet, despite people getting caught writing damning e-mails time and time again.  Sure, we have e-mail retention policies, but that isn't really solving the problem.  If someone wants to bring up a job discrimination lawsuit, they usually do it well within the e-mail deletion period and so this isn't really solving the problem.  

Is there a subset of people who would use this to have affairs and do illicit things?  Perhaps--but if you believe that most people are fundamentally good and don't have stuff to hide, there's not a big market here.  

Then again, Ashley Madison, the site for cheating people, does supposedly have 22 million members, so at $5/month, maybe that's the market they should go after.

Except, that Snapchat does that for free.  

So back to "professionals" we go.  What would a service like this need to get usage among lots of professionals?  

My sense is that there is, in fact, an opportunity in the "professional" messaging market.  A few weeks ago, I talked to someone about the idea of "LinkedIn Messenger"--a way for me to instantly communicate with professional contacts that went outside of the black hole that is e-mail.  

If I meet someone at a conference where I want to connect with them to see if they're free for lunch, how do I tell them where I'm sitting?  I'd rather not give them my number. 

I'd say the two most successful products in the enterprise messaging space were Blackberry Messenger, or BBM, and Bloomberg Instant.  (Side note... "professional" (vs. enterprise) is kind of an interesting newish catagory a la the consumerization of the enterprise).  If you worked in finance and had a Bloomberg terminal on your desk, you used their messenger product to connect and chat with other professionals.  It was like being in an exclusive club of industry folks--What's App for people with money.  People would chat on that product all day.

Lots of those same folks had Blackberry phones, and BBM was the most popular and loved thing RIM ever created this side of a physical keyboard.  Even socially, if you met someone in the industry at a bar, they'd give you their BBM PIN before they gave you their number.  

That's key--both of these services gave people a bit of control over their inboxes.  With BBM, you couldn't get someone's PIN unless they give it to you and with Bloomberg's terminal messenger, it was a seperate inbox.  Even if someone found you and messaged you, it didn't clog up your regular e-mail inbox.  It didn't feel invasive. 

These days, that leaves a bit of a hole--one that I thought at one time that Twitter's messaging capabilities would solve.  Back when I e-mailed Fred Wilson about Twitter in March '07, one of the things I was most intrigued by was the ability to let people reach you by phone with a message, without giving them your phone number--a control layer on top of mobile messaging.  I'm still a prolific DM user, even though the feature is obviously the bastard stepchild of the product.  I'm the exception.  To this day, there's no go to way for professionals to instantly connect with short messages.  Half the time, I DM people only to realize they don't really check it.

Who else does this?

AIM is pretty much dead.

Gtalk/Gchat is a confused product offering at best, awkwardly tying e-mail to chat with hard to find apps.  

Not everyone is on iMessage because it's iOS only.

Blackberry waited far too long to bring BBM to other platforms.

Hipchat and Yammer are internal, leaving no way for me to give someone on the outside of my company a way to contact me.

So, really, before you even ask whether or not professionals need a secure messaging app, I'd suggest someone go about solving the professional messaging problem to start--and make secure messaging a feature.  

LinkedIn is probably in the best position to do this, although I wouldn't count out Blackberry.  I mean, if you just started out today and you could either be Confide, or BBM, and you could add secure messaging to BBM, who would you rather be?  There's still an installed base there, a good brand.  Unfortunately, being tied to the sinking brick that is RIM may be too much for BBM to escape from.

LinkedIn's problem is that the social graph I added to is probably not the social graph of people I want messaging me--so they'd have to use their network as a channel, but the would need to allow users to create tighter circles.  That was the Facebook Places problem.  With Foursquare, you knew what being friends meant.  When Facebook asked me to checkin to a place, I had to rethink whether I really wanted all of these people I went to elementary school with or my family knowing where I was all the time.  If you create a network you have to be clear what adding people to that network means.  Still, even if LinkedIn just used its reach as a channel, it could be a professional mobile messaging juggernaut.  

Maybe they buy Confide--because watching them develop new internal products is like watching paint dry.  Their products are awesome, but there doesn't seem to be a skunkworks over there ready to jump on bandwagons.  

If Confide is going to gain mainstream professional adoption, I think it actually needs to move away from the secure use case and branding.  The branding is too suspicious.  Would you want your significant other to have the Confide app on their phone?  Who are they secretly messaging and why?  Rather, I'd make the messaging and the brand a lot more mainstream and just use the security as a killer feature.  This isn't an area where I see a bunch of secretive driving mainstream adoption--not when it looks gray to even admit that you have it and use it.  

In my mind, professional messaging is a huge opportunity--and it's not likely that any of the existing players are going to get it right, but I don't think being Snapchat-like is the narrow point of the wedge.