Discover Inside tech startups

The voice of VCs and entrepreneurs

Inside tech startups

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 […]

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 [...]

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 […]

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 […]

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 […]

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.

Reservationhate Thisisgoingtobebig Jul 7, 2014

Just to be clear, Reservationhop--the line jumping fake name reservation making most hated startup idea on the internet right now--is not a particularly good idea.

- It's too small of a market with too little monetization per transaction.

- It's rather easily foiled by ID checking.

- It doesn't provide restaurants with any value.

It is not, however, any more morally bankrupt than what a lot of other startup people fawn over. I'm finding all the ethical hemming and hawing over this to be rather inconsistant.

Let's recap...

Napster was totally cool because you got free music, which all us regular people and poor college kids love, while sticking it to The Man (record labels). Totally illegal, but I don't remember too many internet people questioning its ethics.

YouTube was totally cool because "Look, video! And no plugin!" Remember all those things you haven't seen in forever? Yeah, all here. Yay free copyrighted material! Did I miss the ethical posturing at the time?

And when affordable housing advocates complain about Airbnb, they're just standing in the way of innovation, right? Screw the law!

Tor's cool, right? Go Tor! IP masking FTW! Because it's not like we're all using it to watch things we're not legally allowed to because of broadcast rules.

And damn that Supreme Court for forcing Aereo to pay for TV rights the same way all the other TV providers need to!

But, God forbid anyone should mess with Opentable. Jesus, Mary and Joseph! People are up in arms over Reservationhop--the service that sells off hard to get reservations made under assumed names. It's ruining the restaurant business! How dare they!

Ok, let's get something straight. No one funded this thing. There's no board. It's just a guy poking holes in a system testing out demand.

We normally ok this kind of startup tactic. "Don't ask for permission. Ask for forgiveness."

We tell startups to poke the bear and become a thorn in the side of big companies so that th [...]

Joe Perez, Founder of @tastemade, On What Makes a Great Product Manager & More Bothsidesofthetable Jul 1, 2014

Update: Bothsides TV is now available on iTunes, Soundc […]

Lessons learned adding messaging to a notes app (Guest Post)

Lessons learned adding messaging to a notes app (Guest Post) Andrewchen Jul 1, 2014

[Today we have a guest post from Alex Schiff, who's a co-founder and CEO of Fetchnotes, which makes simple, smart tools that help people work together and get things done. Fetchnotes graduated from Techstars Boston in November 2012, and is currently a team of 5 in Cambridge, Massachusetts. -Andrew] Alex Schiff, CEO of Fetchnotes: There’s a […]

Want to Know What Marc Andreessen’s Magic on Twitter is? Hint: It’s Not Tweetstorming Bothsidesofthetable Jun 30, 2014

By now almost everybody knows that Marc Andreessen has […]

Why Venture Capital is So Much More Compelling Now Bothsidesofthetable Jun 29, 2014

It’s not hard to find people willing to write the […]

Officially Announcing Bothsides TV Bothsidesofthetable Jun 25, 2014

For 2 years I interviewed VCs & founders for a show […]

Why I Doubled Down on YouTube Investments with MiTú

Why I Doubled Down on YouTube Investments with MiTú Bothsidesofthetable Jun 20, 2014

Yesterday MiTú Networks announced that Upfront Ventures […]

The Strong Rejection Thisisgoingtobebig Jun 23, 2014

When I turn down the opportunity to invest in a startup, I really turn it down.

I try and say exactly what I don't believe will happen, or why I don't believe in what you're doing. In essence, I'm setting myself up to either be spectacularly wrong or to be right.

The last thing I want is to not have a view on the space. My job is to have views--because not making a bet is making a bet. If I don't have clarity on something, it means that I don't think the space and the opportunity size is big enough to get clarity.

What I never say is "I love what you're doing, but...". Sugarcoating isn't helpful to entrepreneurs. You never want to get a rejection and scratch your head over why the person turned you down.

I'll tell you right now that I don't think a new form of video messaging is either a) something that consumers really want or b) a great way to make money because monetization just creates friction in the communication process.

I could be 100% wrong about that, but that's my bet. We'll know in a few years if I was right or wrong. In my mind, uncertainty should never be a reason for an early stage investor to turn a deal down. The world is uncertain and making bets in an uncertain world is what risk is all about.

So, I'm certain that I'll either be certainly right or certainly wrong--but I'm always certain.

I've been helping to syndicate a few opportunities lately and what has really surprised me was how wishy washy the turndowns were. Entrepreneurs are sending me back notes saying "They turned it down, but I'm not sure why." It's unclear what piece of information they were lacking or how someone could have gotten them over the hump. It doesn't help them improve their pitch or adjust their model. It just feels like the VC wasn't that interested in the first place and so they're not sure what the interest was in the first place. If you take a smart home pitch, and you turn it down because you're not certain how the smart home segment will play out [...]

The Power of Getting the Band Back Together

The Power of Getting the Band Back Together Bothsidesofthetable Jun 22, 2014

Startups are hard. You’ve heard that a million ti […]

The Business of Who Makes is Changing Thisisgoingtobebig Jun 19, 2014

The 1970's was a boom for minicomputers. Minicomputers were "midrange" machines that were used in all sorts of industrial applications--manufacturing process control, telephone switching and to control laboratory equipment.

"In the 1970s, they were the hardware that was used to launch the computer-aided design (CAD) industry," according to Wikipedia.

"The first commercial applications of CAD were in large companies in the automotive and aerospace industries, as well as in electronics. Only large corporations could afford the computers capable of performing the calculations. Notable company projects were at GM (Dr. Patrick J.Hanratty) with DAC-1 (Design Augmented by Computer) 1964; Lockheed projects; Bell GRAPHIC 1 and Renault."

Those were basically the makers of the time--only big Fortune 500 companies had the resources to create at scale, so if you were building tools for makers, it was a B2B sale involving a lot of big iron.

Microcomputers gave way to desktops and software made great advancements. It is perhaps not surprising that both Autodesk and Adobe--the two software companies probably most responsible for digital first creation, were both founded in 1982. Their tools brought creation ability out of labs with expensive hardware to masses of professionals in both large and small companies.

Still, users of creation tools were mostly professionals. It takes a fair bit of skill to be adept at Adobe Illustrator or to use AutoCAD. What we're seeing now is a third shift in the maker market--to individuals and hobbyists, i.e. everyone. Quirky helps you develop and market your product ideas. Companies like Makerbot and Shapeways bring physical production to the masses. Etsy is a marketplace for things you make.

There are also places to deposit what you've built or designed--Thingaverse is a core component of the 3D printing ecosystem. GrabCAD helps CAD designers collaborate and leverage off of each other's libraries. Splice is doing similar work in t [...]

How early should you connect to a VC? Here's some data. Thisisgoingtobebig Jun 16, 2014

How long does it take from first meeting a VC to getting cash in the bank?

That's an interesting question. Theoretically, someone could meet you, sign your document, and write you a check for deposit that day, but that's not how it usually works.

It's also not the best way to create a helpful syndicate of investors that share the founder's vision for the company.

Examining the actual data not only gives me some insight into my close process, but it helps me calibrate around relationship building. If all my deals came as intros from trusted connections that I know for years versus at founder pitch events that's interesting data. I might decide that I'm not mining one side or the other, or I need to redouble my efforts to build relationships with the people I know longest.

It also helps me figure out who I should be spending my time with. If it turned out that the best experiences I've had as an investor come from knowing someone a long time, I might go to events that are more around a specialty, like software development or design. In this case, I'd have the benefit of knowing someone long before they created a company. If you meet someone at a pitch event, they've already got a company and they're looking to close as quickly as possible.

In fact, that's what I tend to do--at least, what I say that I do. The way I choose conferences and events, and my strategy once I'm there, is based more around who I'm going to back two years from now than it is who is raising now.

But does the data play that out? How long in advance did I know someone, or know about a deal before I wired money? What led me to knowing about that deal in the first place and when did that event happen?

I went back across the 21 investments I've made both at First Round and at Brooklyn Bridge Ventures--a period that dates back to January 28, 2010, when I closed on Backupify. I looked at how I got the deal, when I first met the company, when it closed, and then what connection I ma [...]

Brooklyn Bridge Ventures invested in Ringly because being present is fashionable Thisisgoingtobebig Jun 10, 2014

A year ago, I wrote a post about how I was trying to keep my phone away during meals--No Phone with Food. These days, we've got so much that can distract us, being present has become a rare feat. I've tried to stick to it, but it's hard. I run my own business and I try and make myself available whenever my entrepreneurs need me. I also have a lot of family responsibility--with parents getting older and my grandmother making her way ever closer to 100, there are a few important folks I always want to stay connected to.

The problem is that the phone is a rabbit hole. With just a few app installs, the notification screen quickly becomes short attention spam theater. Sometimes, I wind up in Twitter or Instagram on my phone without even remembering why I pulled the phone out in the first place.

For a guy, it's just too easy. With my phone in my pocket, it might as well come out of a holster.

For women, its worse. Either you dump your phone into the black hole known as your bag, never to be heard from again, or it sits right there on the table as the third wheel. There's nothing more distracting than having a phone buzz on your table or needing to walk around with it all the time.

It says a lot about the evolution of mobile technology. Cameras, for example, got smaller and better to the point where we didn't need a seperate device--and they just wound up in our phones. Same thing for GPS. Now, your phone is everything to everyone--a device you're always attached to. What's lost in that process, however, is matching right interaction with the right time and place. That's part of the promise of wearables, the connected home, and devices in cars. I don't need a phone to provide me every notification and every tool all the time, but different devices have their difference place in my life.

Ringly is a platform for fashionable wearables, enabling them to filter your world for what you care about. It's all about getting notifications in the right moment, without [...]