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Bad Notes on Venture Capital Bothsidesofthetable Sep 18, 2014

This week. On the phone … Me: So, you raised vent […]

Why We’re Looking to Fund Stuff With More Meaning Bothsidesofthetable Sep 15, 2014

Venture Capital is a tricky industry. If you’re f […]

New data on push notifications show up to 40% CTRs, the best perform 4X better than the worst (Guest post)

New data on push notifications show up to 40% CTRs, the best perform 4X better than the worst (Guest post) Andrewchen Sep 16, 2014

[Andrew: A few weeks ago, the folks at Kahuna released some great data showing that up to 60% of users opt-out of push notifications. Now they're releasing some new data on the click-through rates of push notifications, showing the differences between app categories and breaking down the reasons why some apps are so much stronger than […]

Setting Kids Up to Fail Thisisgoingtobebig Sep 15, 2014

The nature of work is changing--we all know that. You're required to be a lot more entrepreneurial, which requires you to build your own networks in order to get customers and collaborators, since these functions won't be under the roof of a big company anymore.

You'll need to be more mobile, nimble, and able to go where the work is. You'll need to think globally.

You will need to be a continuous learner, willing to pick up new skills as the world changes around you--meaning that your sources of education won't necessarily be accredited academic institutions.

This is all pretty obvious, and has been for a while, right?

So how does this respond to how we seem to be teaching our kids?

Well, for starters, each generation seems to be facing a shrinking, not growing world. Below is a graphic from a DailyMail article that shows how far kids in a family were allowed to roam as eight year olds.

From the DailyMail

Could you imagine letting an eight year old roam eight miles away these days? You'd probably get arrested for child neglect. However, how prepared was that kid for the rest of life after making those trips, compared to kids today that rarely ever leave the house on their own? How prepared are kids today to face a global world when they can't walk off of their own block.

How likely are they to become lifelong learners when we've never had more emphasis on standardized testing, and therefore standardized learning? The school we create for kids now makes them want to be done with school as soon as possible.

It's like when people ask me how to get into venture capital. They're always asking about the right way to do it, how to get an interview--all these very structured ways of approaching a system. When I tell them stuff about adding value to the community, creating a personal brand, etc., it just doesn't compute. Nothing that I ever did to get where I am in venture was difficult or special--but none of it was anything you really learn in a [...]

Here’s How to Cancel a Meeting the Right Way Bothsidesofthetable Sep 13, 2014

I wrote a version of this post four years ago but given […]

Five Tips for Getting PR for Your Startup Thisisgoingtobebig Sep 8, 2014

Because, you know, who doesn't love a good startup list.

1) Figure out who has written about companies like yours and reach out--when you don't need something.

Think about who else is in your space--other wearables companies, companies also focused on the smart home, you name it. Those are going to be the reporters who are most likely willing to write about you. When you've got that list together, just individually e-mail as many of them as you can. Just introduce yourself and offer yourself up as a resource.

"Hi, I just wanted to thank you for covering this space. I like the angle you took on this particular article/I appreciate that you've taken the time to highlight what all these companies are doing because others aren't/something nice about the reporter's effort. I know all of these companies and a lot of others that are popping up because I have X expertise and experience, so if I can ever be a resource to you, even on background, please do feel free to contact me. I've included a short list below of a few 1-2 sentence thoughts, predictions, or generally crazy ideas that I don't think are shared by my peers about where the space is going to give you a sense of what my perspective is.

I'm actually starting a company/have started a company in this space and don't have anything to share at the moment, but will at some point would love to be able to share our funding news, product launches, or maybe collaborate with other companies on trend pieces in the space."

This way, the journalists most interested in what you're up to reveal themselves by engaging with you based on that note--and you've given them a reason to contact you. Maybe the fact that you think that Amazon will get into Cleantech for some crazy reason or that phone numbers will eventually disappear in favor of just connecting to people or companies will strike a chord--or maybe even inspire a future article.

2) Follow journalists on Twitter and Instagram

These folks are real human [...]

Here is How to Make Sense of Conflicting Startup Advice

Here is How to Make Sense of Conflicting Startup Advice Bothsidesofthetable Aug 31, 2014

Everybody has a blog these days and there is much advic […]

Never ask for "Just 5 Minutes!" Thisisgoingtobebig Sep 3, 2014

A few weeks ago, I was talking with a founder that I backed and he was telling me how excited he was about his company. He said the path was so clear that he could literally see it--and that's the way he's always been since I met him. He has a quiet confidence and he's excited to talk about his company--and he could go on and on if you let him.

It's a stark contrast to people who beg for "just five minutes" of my time. I understand that fundraising is hard, but if you do you best to leverage your network to connect to a bunch of investors, and you can't even get a first meeting, you may have to rethink what you're up to. When you ask for just a few minutes, it sounds like you're having a lot of trouble getting meetings. That's a signal the market is giving to you. VCs may only do 1-2% of the deals that come their way, but I'd say they probably take about 20% of the requests for first meetings.

Think about that for a second. If they only actually invest 1% of the time or less, and even half of those companies go out of business, then when you can't even get a meeting you're outside of the top 20%, and you need to be in the top 0.5%. That's not even close.

On the other hand, maybe you're just acting like you're not even close. When you approach investors as if they're taking mercy on you by talking with you about their company, they're going to assume that something's up. Imagine being on a date where someone says "Oh, thank god you actually showed up!!"

You might wonder whether you're both dating out of your league--with you being on the short end of that stick.

If you're working in a big enough market, you're the right person to be working on something, and you've made some headway doing what you're doing, you should have no problem getting investor meetings. Nothing ever gets done in just 5 minutes, so if someone says no to a meeting, either take that as market feedback or just move on to someone who is interested.

And trust me, a demo never makes [...]

Startup Traction Starts With The Right Goal. How To Get It Right. Onstartups Aug 28, 2014

Without traction -- sustainable customer growth -- your startup will languish or die. As such, traction should always be top of mind.

To focus your traction efforts, you need a traction goal to work towards. Example goals are 1,000 new users, 100 new customers or 10% market share.

Why Android desperately needs a billion dollar success story: The best new apps are all going iPhone-first

Why Android desperately needs a billion dollar success story: The best new apps are all going iPhone-first Andrewchen Aug 27, 2014

Why startups are all going iPhone-first There’s been a number of articles over the last year that reiterate a simple fact: The best new apps are all going iPhone-first. Here’s three popular articles on this topic over the last few months: iOS First. Android Much, Much Later (Aug 2014) The Fallacy of Android-First (Apr 2014) Why Android First is a Myth (Oct […]

Early Traction: How to go from zero to 150,000 email subscribers (Guest Post)

Early Traction: How to go from zero to 150,000 email subscribers (Guest Post) Andrewchen Aug 14, 2014

[Andrew: Starting up from zero is one of the hardest things you can do with a new product. Especially in the age of SaaS and content marketing, building up to the first 150k users is a key milestone that can prove out product/market fit, generate a revenue stream, and secure investment. This is a guest […]

New data shows up to 60% of users opt-out of push notifications (Guest Post)

New data shows up to 60% of users opt-out of push notifications (Guest Post) Andrewchen Aug 6, 2014

[Andrew: There's a real shortage of information about push notifications, CTRs, response rates, etc. Partly this is due to the immaturity of mobile as a marketing platform, but it's also because of the opacity of the iOS platform. I recently ran into Kahuna, a Sequoia-backed startup led by Adam Marchick that's compiled a treasure trove […]

Why aren’t App Constellations working? (Guest Post)

Why aren’t App Constellations working? (Guest Post) Andrewchen Aug 4, 2014

[Recently, I read this roundup of perspectives on "App Constellations" on the new social/professional news app Quibb. This is an emerging product strategy in mobile embraced by Facebook, Linkedin, Foursquare, Twitter, and others, and found it fascinating. Thanks to the authors below for sharing their opinions on this new approach. -Andrew] Fred Wilson recently coined the term […]

Invest in Karma for Above Market Returns Thisisgoingtobebig Aug 27, 2014

Yesterday, I took my 96 year old Nana to Atlantic City.

As you can see from the photo, she didn't win, but I did. Almost $200. Still, she had an awesome time and was thrilled to go. Protip: Don't bother with the valet at the Taj Mahal. By the time they get to you, you could have walked over, gotten your car yourself and come back to the front.

Just this morning, someone on a rec sports team that I play on just told me that they lost their job and couldn't pay for softball anymore. This season costs about $100. House money, as far as I'm concerned. I told him to consider himself covered by Donald Trump. I didn't hesitate because a) Eh, money comes, money goes, b) I like this person and want to play with them, and c) karma always comes back to you.

It made me think of something I heard on a podcast the other day--about how leaders get help. I've gotten a lot of help from a lot of people over the years, but I realize that's because of the investments I've made in helping others. What I've seen is that if I make it a regular part of my investments in time to help others, when I do really need something, I've got a huge store of willing effort to tap. That's extremely valuable. It's not why I do it, but I'm also not oblivious either. Like a good Pavlovian dog, I continue to give my time and help to others when that happens.

On the other hand, if I never do anything for others, I'm creating a lonely island for myself where I'll need to rely on just myself to get anywhere. That would not only suck, it would hurt the trajectory of my career and my firm's efforts.

You cannot do it all alone.

So, while it feels good to help others, it should also be a part of any leadership strategy. It's a bit like insurance. Squirrell away a little bit of karma each week by doing something for someone else, because one day you're definitely going to need help to get pushed over the top.

Still, I see selfish founders who don't treat others well. It's a hard thing to do w [...]

How Technical Advisors can Help Non-Technical Founders Thisisgoingtobebig Aug 21, 2014

No one wants to be *that* founder--the non-technical founder poking around developer meetups asking for a unicorn with a Github account. It's not that there aren't great technical people willing to take a lot of risk to join a small team--it's just that there are *so many* people out there looking for them that it's hard to figure out who to take seriously.

This is where a good technical advisor can help. They can help vet what you're building, give you credibility in the hiring process and help assess candidates.

Go find someone technical you could probably never hire. Maybe they're locked up in golden handcuffs post-acquisition of their startup. Maybe they're coding at Google and at a point in their life where they'd rather make $300k than rough it at a startup.

What you can offer is interestingness, a thoughtful challenge, and a little bit of equity. Working with young companies is cool and it gets the juices flowing. Plus, from the advisor side, it might be a good way to build up a little portfolio of startup equity without having to put up angel cash.

Here are the three things I would ask a technical advisor to do for you:

1) Help you build a high level tech spec of what you need to build, so that you know that the product you're working on can reasonably be built given a) the current stage of technology and b) your resources and timeline. They're going to tell you why an elevator to the moon is hard and why a stepladder might be a better place to start if you only have $50 and a carpenter with a hammer and a saw.

2) They can be your advocate in technical circles. It's a much stronger pitch when a software developer reaches out to another software developer and says "Hey, I saw your profile and it might be a very good fit with this company I'm advising" than when you do it and you look like the masses of MBAs looking for code monkees. Plus, it gives you some street cred if at least one software developer thinks that what you are building shoul [...]

Here’s What President of textPlus @Nanea Reeves Has to Say on Leadership, Mgmt, Women in Tech Bothsidesofthetable Aug 18, 2014

Just back from vacation and also some work travel and w […]

The Things that Fall Down Thisisgoingtobebig Aug 15, 2014

The other day, I found this neat inbox stats tool from Front App called Inbox Checkup. (Thanks Product Hunt!) I've been wanting something like this for a while.

Apparently, I respond to 18% of my e-mails, way above the average of 11%, and was #62 out of over 4,000 in terms of e-mails sent. It was happy to know that I'm getting to a lot of things.

Unfortunately, I was also #145 in actually getting e-mails, so what that also means is that while I'm getting to a lot, I'm also missing out on a lot. What is painful is when I know there's that one note I should be responding to or one thing I promised to do that just keeps getting pushed off to the next day. Like a splinter, you feel it distracting you just a little bit.

What's hard is that other people don't understand it. What they've asked you to do will just take a minute. Why is that so hard?

Those minutes add up, though... and you have to make some priorities. I need to call my parents, my nana, respond back to that text about where I'm having dinner tonight, and oh yeah, my softball team needs an extra player for tonight otherwise we'll forfeit, so that's a problem. And that's just personal stuff that doesn't include my desire to go to the gym or get some extra biking in so that I can beat Dave Morgan in our charity challege for the marathon. (Donate!)

I've got things I need to do for my portfolio companies, deals in process, investors of mine asking questions, and the list goes on and on...

And with each new thing, you try and slot it in somewhere... and sometimes, it's after midnight and you're done. Whatever was on that list, well, this teller window is now closed and it will just have to wait.

It's frustrating and there really isn't a good solution, unless someone wants to make extra minutes in the day. I feel like I'm getting to a ton and super efficient--but that doesn't mean I don't feel bad when I fail to recommend that content person to a few VC firms I know, or I didn't pitch that lat [...]

Piers, Parks and Why White People Suck Thisisgoingtobebig Aug 6, 2014

There's a saying...

"There's nothing worse than rich white people living in luxury housing in a park than the rich white people living in luxury housing protesting against them."

Ok, well, there wasn't a saying, but there should be.

Maybe you've heard about "The Battle of Brooklyn Bridge Park." It's a long and winding tale that basically amounts to this:

There once were some unused commercial piers. Someone decided they should become a waterfront park. Parks are expensive to build, so it was decided to cleave off a little bit of the park for waterfront housing to pay for the park. The plan worked and now the park is beautiful and extremely popular. Like, ridiculously popular.

Everyday, tens of thousands of people visit the park's many amenities--beach volleyball, picnic grills, a pop-up pool, kayaking, standup paddleboarding, roller skating, and sure, hills, trees, grass, and spectacular waterfront views.

This pisses people off.

Come again?

Actually, there is a small but vocal group of folks who never liked this version of the park--who wanted something more akin to a lawn for their Brooklyn waterfront property. They want quiet people to tiptoe silently past their brownstones on the way to the park, and only during daytime hours.

These local folks are suing the park itself because of plans to build luxury housing in the park.

At first glance, you'd think with everything I just said, I'd be on their side. Doesn't the idea of luxury housing go against all this cool park activity?

No. Actually, we wouldn't have any of that stuff if it wasn't for the housing plan.

You see, building a park is a very expensive proposition--especially a waterfront park. The piers, vacant for years, had to be repaired. The cost for the park totals in the hundreds of millions of dollars. The city doesn't have the taxpayer dollars laying around to pay for such a thing, so it was decided to leverage the value of waterfront NYC real estate to create a self-su [...]

Know When Conceding on a Point is Better Than Being Right

Know When Conceding on a Point is Better Than Being Right Bothsidesofthetable Aug 3, 2014

Last Wednesday I had coffee with an old friend and form […]

The Changing Structure of the VC Industry

The Changing Structure of the VC Industry Bothsidesofthetable Jul 23, 2014

There has been much discussion in the past few years of […]

The 7 Speakers Even This Introvert Will Go See At INBOUND 14 Onstartups Jul 31, 2014

I’m an introvert at heart. That means I don't draw energy from being around people and definitely don't crave it. So I usually spend more time in twitter discussions and AMAs than face-to-face conversations. As you can imagine, events tend to inspire some anxiety in me. Whether I’m at a conference as an attendee or as a speaker, thousands of humans in one place usually sends me running in the other direction.

But, some events are worth standing in place for. At the Business of Software conference each year, I camp out at the venue before and after my talk to experience everything from the breakout sessions to the happy hour conversation. I usually do the same thing for the annual INBOUND conference that my company HubSpot hosts. But there was that time last year that I missed Arianna Huffington giving me a hard time on stage during her keynote for not getting enough sleep, when ironically, I was upstairs in my hotel room taking a nap. Even if you’ve been running on empty for weeks leading up to your company’s cornerstone event, I learned the hard way that the first rule of being an attendee is stay awake for the keynotes.

Step Up Thisisgoingtobebig Jul 28, 2014

I wrote this note to a young company that had recently raised some money and moved into a shiny new office after busting at the seams in a makeshift setup. The company was full of super young, vibrant, and incredibly talented people with a huge opportunity ahead of them--and a lot of difficult challenges.


Congrats on moving into your new office.

While I'm there are still a few bugs, bells, whistles, and bandwidth to work out, let me be the first to officially point out...

Shit just got real.

You have a real office. You're all together. You're organized into teams that are basically complete as a unit. Now, through the end of the year, will be a full on sprint like you've never run before. Crush it and this whole thing will take off like a rocket ship--with your work touching the lives of millions and millions of people around the world for years to come.

Make the most of this opportunity to build one of the most creative and inspiring places to work in the whole damn universe.


This is enormously important work. The world really needs this. I don't know if you noticed, but there are a lot of people out there who think of the world as a zero sum game--where anything gotten must be taken away from someone else and where those in power are resistant to sharing.

Creativity inspires people to reexamine the world around you--to challenge, to poke, to ask why.

And that's what you have to ask yourself now.


Fulfilling the potential of this endeavor will be the hardest thing you've ever done in your whole life up to this point. It won't just be about late nights and heated disagreements but also pushing yourself to be better than you thought you could ever be.

Why bother?

Why put in so much effort?

Why strive?

People come up with all sorts of motivations--fear, money, fame...

Let me present what I think is a more fitting motivation for creative professionals on the verge of creating a very [...]

A Great Discussion with @skupor @davemcclure @msuster on Changes in the VC Industry Bothsidesofthetable Jul 27, 2014

I recently attended and presented at Dave McClure’ […]

Here’s Why a Booming Tech Market May Fool You into Thinking You’re Successful Bothsidesofthetable Jul 22, 2014

Since 2009 we’ve been in an unequivocal bull mark […]

Growth is a Commodity Thisisgoingtobebig Jul 21, 2014

If there's one thing we've basically figured out in the digital world, it's marketing. There's no more well tread aspect of building an online business than marketing. We've got more channels, tools, and analytics to tell you weather or not it's working than you can shake a stick at.

It's table stakes. You spend some dollars to get more dollars out. It's not complicated.

That's why I care much more about engagement--do people like what you built, versus whether or not more people used it today than they did yesterday. Plus, the startup world is littered with companies that grew exponentially without becoming successful--Fab, Turntable, Dailybooth, etc.

If people engage regularly with your product, but you can't get more people to use it, you've got a marketing problem. Marketing problems, for the most part, are solvable by a very distinct set of best practices. You've just got to figure out why the current set of people like it, and find more of them. Now, maybe there just aren't that many people out there, but for the most part I see a lot of low hanging fruit ways that marketing could improve.

On the other hand, if people are coming, but they're not engaging, you've got a product problem. Sometimes, it's easily fixible. Other times, you're just so way off on product/market fit that you've fallen into "bad idea" territory, and there's really no timetable for fixing a bad idea.

On top of that, there's another problem that startups have more trouble figuring out than marketing--scaling. What do you do when you actually start getting people in the door? How does your sales support staff change? Where's the first bottleneck? Does the experience in your marketplace suffer at all because you've got an influx of too many sellers, or buyers?

In a seed round, I think it's safer to prove engagement and the ability to create a scalable process, than to load up on customers. This way, you know that you've got enough in place not to fall apart when you do grow [...]

There’s only a few ways to scale user growth, and here’s the list

There’s only a few ways to scale user growth, and here’s the list Andrewchen Jul 8, 2014

Scaling growth is hard – there’s only a few ways to do it When you study the most successful mobile/web products, you start to see a pattern on how they grow. Turns out, there’s not too many ways to reach 100s of millions of users or revenue. Instead, products mostly have one or two major growth channels, […]

Towercutting with goTenna Thisisgoingtobebig Jul 17, 2014

I'm excited to share that goTenna, a Brooklyn Bridge Ventures portfolio company, has launched the presale of its point to point communications device.

Have you ever texted anyone in the same room and thought about the infrastructure behind it--about where that message travels to, the great distances it gets bounced around, all to travel ten feet, in just milliseconds.

It's pretty magical.

It's also pretty stupid, technically speaking.

When you can literally see someone else's phone, even a three year old would suggest that the message should go from point A to point B on a pretty straight line.

There's a lot of other things about telecommunications that a three year old would probably agree with--that no one should ever be able to read your message, except the person who sent it to you.

And if you go on a remote camping trip and one of you gets lost on your way to the hole in the ground behind a tree, you should be able to contact each other if you both have phones.

These situations--the lack of coverage in emergencies, the need for privacy, and the ability to offload point to point communications--make goTenna a pretty handy device to have around. It is a small piece of hardware that syncs up with your phone, freeing it from the carrier network and enabling point to point communication.

But handy isn't why I backed it. Handy is the first step to gamechanging.

I met Daniela Perdomo over a year ago at SXSW. I was scanning the SXSWSocial network for anyone that had tagged themselves "Brooklyn". Daniela's profile came up and I noticed that she was involved with NYC Resistor, the hardware hackerspace that Makerbot came out of. I tweeted at her in response to a post about cheese.

@danielaperdomo That is serious! BTW... Putting together a little dinner of folks Sun night. Would love to meet a Bklyn maker/Resistor.

— Charlie O'Donnell (@ceonyc) March 9, 2013

We agreed to meet up and she told me what she was working on. I had no ide [...]

My Role as a VC: What I am and what I am not. Thisisgoingtobebig Jul 16, 2014

There's been some writing about how VCs and founders interact with each other and it inspired me to take a step back and reflect on what my role is supposed to be with regards to the investments I make and the founders I deal with.

Here's what I came up with...

First, I have a fiduciary responsibility to my investors who entrusted me with money in the first place. If I don't do right by them, then I have no money, no fund, no career, full stop. They count on me to be a good steward of their capital, and to take reasonable and appropriate risk with the expectation of a certain level of returns.

That also means that I need to act in a way that ensures my ability to get future opportunities to invest their capital in attractive deals. Rather than using my investors as an excuse to be short-sighted and screw over the first entrepreneur that works in the door, I need to balance their need for return with the long term viability and reputation of the fund and the firm. I believe that ethics and opportunity for investors will go hand in hand over the long term--and opportunity drives returns.

It also means I need to be really careful about how I'm spending my time. I want to be helpful to a lot more people than I'm able to spend time with, but I can't distract myself too much from this clear and primary mission.

Second, I am a provider of capital--so my check needs to clear and I need to be transparent about when and if I plan to invest, or if entrepreneurs should look elsewhere.

Third, I try to help my teams be the best company managers they can be--because ultimately, no matter how much help I can be, it's up to them to do most of the heavy lifting. That does not mean telling them how to run the company, but to help them create a management discipline--a framework for thinking about problems and solutions. I am there, along with other investors and board members to audit their thinking--to make sure they were considerate about the plans *they* came up w [...]

The Gentle and Visual Guide to Startup Marketing Onstartups Jul 8, 2014

There are two things in my professional life that I'm passionate about.