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Be Honest About Whether Your Product Really Makes a Difference Bothsidesofthetable Jan 26, 2015

Startups in a world of massive markets can be confusing […]

How to Build Online Relationships into Meaningful Networks Bothsidesofthetable Jan 24, 2015

I was waiting for my son’s basketball game to sta […]

The Most Misunderstood Facts About Building a Business on YouTube

The Most Misunderstood Facts About Building a Business on YouTube Bothsidesofthetable Jan 20, 2015

Any reader of this blog for a period of time will know […]

What happens when you find the right journalist for the story Thisisgoingtobebig Jan 22, 2015

I'm incredibly excited to announce Brooklyn Bridge Ventures' investment in Plum Print. Plum Print turns your kid's artwork into buyable merchandise like coffee table books, and soon note cards, framed prints, and calendars. While other apps store art for future printing, Plum Print is different because it doesn't require large amounts of time for you to do it yourself. You throw everything in a box and Plum Print does the hard work for you, returning the art and a completed keepsake. So, yes, they're conceding the market of parents who have enough time to scan hundreds of pieces of artwork a year.

I don't think that's a big market. :)

I'll talk more about my investment in another post, but what I really loved about their announcement today was how great the article in Techcrunch was. Sometimes, you send some info over to a reporter and they do what needs to be done, but the result is the same kind of story you see everywhere else. Yes, I'm accusing tech journalists of barely rewriting press releases.

And you know what, why shouldn't they?

You sent them the same pitch you sent everywhere else. If they bang something out in twenty minutes, you'll link to it, you'll get some traffic back, they'll get traffic--it's transactional. If you treat PR like a transaction, that's the way press will treat you back.

So when Meg and Carolyn wanted help on their announcement, I knew the right person to cover it from the tech side--Sarah Perez from Techcrunch. I met Sarah in person at Techcrunch Disrupt in NYC a few years ago. We had connected by e-mail about Tinybop and I knew she was interested in kids apps and companies. She's a mom herself and her family is a big part of why she lives down in Florida. So, she knew why I was sending her the Plum Print story and I, just as importantly, I knew why I was sending her the Plum Print story.

I just read the story she wrote and it's fantastic.

It's comprehensive--it covers all the major points about their new upcomin [...]

Blogging for the Hell of It, Not Blogging to Stay Relevant Bothsidesofthetable Jan 18, 2015

. I used to love blogging. For me it was always a creat […]

A result. Faster. Thisisgoingtobebig Jan 15, 2015

Why do startups fail?

They run out of money, of course. That's an oversimplification and actually it's more the result than the root cause.

A lot of times, it comes down to failing to produce results, and enough of them. What I've realized recently, though, is that smaller, faster results are key--and it doesn't always matter whether those results are good or bad.

I know a few startups that are struggling with their execution and it strikes me that they don't have any enough small victories. Their goals are all or nothing, like big product releases. For months, they're building the next thing, and there's little for the CEO to accomplish in the meantime.

Similarly, they get stuck in trying to negotiate with a huge customer for months on and end it ties up their resources.

Even in the beginning, some founders can't move forward until they raise their seed round. All you ever hear from them is whether they raised their seed round or not--and the company just seems dead in the water.

There are no small victories.

Having small victories isn't a function of winning and losing--it's about the design of your goals and your approach to them.

Language is incredibly important here. It starts with your team's disposition around new goals.

When your team decides that enterprise users should be able sign themselves up, that's a big project. That involves automating a ton of things that aren't automated yet and untold headaches for your tech team.

What's the reaction when the CEO says "I've gotten feedback from customers that they want to just try the product out themselves, and the setup and support team is already overloaded...what would it take to allow people to set themselves up?"

If the first reaction from an already overloaded tech team is a face palm and an "ugh", that's a problem that goes deep. That means the people involved are only thinking of the end goal and nothing in between--and not positioning themselves to allow for small wins. [...]

8 Unconventional Lessons From Quitting My Job At HubSpot

8 Unconventional Lessons From Quitting My Job At HubSpot Onstartups Dec 29, 2014

The following article is a guest post by Ellie Mirman. Ellie is the VP Marketing at Toast. Check out her blog or follow her on twitter: @ellieeille.

Upfront Ventures Raised New $280 Million Fund

Upfront Ventures Raised New $280 Million Fund Bothsidesofthetable Dec 16, 2014

Whew! We’ve been dying to tell you all for a whil […]

Overcoming The Odds: 10 Tips For Getting Into A Top Accelerator

Overcoming The Odds: 10 Tips For Getting Into A Top Accelerator Onstartups Jan 5, 2015

Just as the CEO is the investor’s interface to a business, the application process and form is your interface into top accelerators like Techstars and Y Combinator. The best programs are super-selective--less than 1% of applicants get in, making them pickier than Harvard, Stanford and MIT. So as our New Year’s present to you, here is the scoop on how to improve your odds of getting in.

We can’t speak directly for any programs other than TechStars Boston, which the two of us have known and been involved in for years, but these hints should improve your chances significantly just about anywhere.

Excited to be the Least Stylish Investor in the Most Stylish Company: Backing Bradford and Bezar Thisisgoingtobebig Jan 8, 2015

To date, I've backed three fashion related companies--Refinery29, chloe + isabel, and Ringly--and now I have the pleasure of joining the syndicate of investors in Bradford Shellhammer's new company, Bezar.

Could I a less likely candidate for such a portfolio? :)

Bezar is where you find people who design the kinds of things that I see in other people's apartments and stop to pick up, inspect, wonder at and think, "That's awesome... I would have never thought of adding that to this place."

It's the kind of place where you buy clothing that make people notice because it's cool and interesting--even people like me, currently typing this with a Mets t-shirt on and jeans that I bought at Macy's.

It's a platform that puts the emerging designer up to be celebrated and I'm just as excited for the designers that are going to be featured on the site as I am for Bradford and his terrific team.

How I got to this investment was another long term story. I was a huge buyer in the early days when we backed it at First Round Capital. It was the only marketing e-mail I opened up everyday--because it always had the coolest stuff. Each e-mail brought with it something that I felt that need to tweet and share--and many, probably too many times, something I bought.

That was the core of what Bradford brought to that company. It was built around his design sense.

But Fab fell into the trap that many companies who go down the VC route fall into--too much money, too soon, and growing too fast. Money pushed the whole thing off the rails and made it into something that wasn't the exciting thing it was when it first launched.

After Bradford left, I reached out to him and asked him to get dinner. I wanted to hear his lessons learned and help him figure out his next thing. Small world, it turns out I also knew his husband from the finance world having met him over 10 years ago.

We had a great chat and stayed in touch. When he told me he was launching Bezar and as [...]

My top essays in 2014 about mobile, growth, and tech Andrewchen Jan 6, 2015

Hello readers, Happy 2015 and hope everyone had a relaxing holiday. As always, more essays are coming soon for the next year. In the meantime, I wanted to share some of my essays published here over the last year. If you want to stay up to date, just make sure to subscribe for updates. Also, thanks […]

The post My top essays in 2014 about mobile, growth, and tech appeared first on @andrewchen.

Turns at Albuquerque: How I Measure My Career Thisisgoingtobebig Jan 5, 2015

I love thinking about career paths and how people get from A to B. It's my favorite thing to teach as well--and I'll be giving a class at Startup Institute this Tuesday night about it. They're a career accelerator, which is a pretty neat concept--doing what YC and Techstars do for startups, but for your career.

Anyway, 2015 marks a couple of big career anniversaries for me.

Twenty years ago, I got my first job. I started working in 1995 at the age of 15 in the mailroom at Waterhouse Securities (which became TD Waterhouse) at 100 Wall Street.

Ten years ago, in 2005, I started working for Union Square Ventures as their first analyst.

I've always thought about plotting where I was in my career against where I thought I should or could have been at my age. Sure, there are outliers who start companies at age 19, but that didn't seem like a fair comparison. I was aiming more for the top quartile--who was at top of my field that didn't seem to get there via a fluke--whose career might actually be replicable.

When I was working for USV, I learned of Chamath Palihapitiya's career. At 28, he became the head of AOL's Instant Messenger (AIM), which was a big deal at the time. When I was 26, I called him up and asked him about his background to try and figure out how, in two years, I could be running AIM (or rather, the equivilent impactful job).

What I learned was that Chamath's career path was the product of three things: First, being really good at what you do, obviously. Second, was taking risks. He didn't aim to become the head of AIM. He joined a startup that wound up getting bought by AOL. He later took a similar risk by joining Facebook when it was just a year old or so.

I reiterated the notion of risk taking when giving career advice the other day and how when I joined Union Square Ventures, it wasn't the USV it was now. Fred and Brad didn't have the reputations they do now. Barely anyone had ever heard of them. Getting a job at USV was much easier [...]

How Not to Let the Crazy In Thisisgoingtobebig Dec 15, 2014

A friend of mine is starting a huge new project. She told me that 2015 is going to be the craziest year she's ever had.

I suggested to her that it will certainly be the busiest, but that she didn't have to let the crazy in.

We throw around the word "crazy" but in all seriousness, mental health is something that doesn't get much discussion in the startup world. There seems to be a blog post, book or boot camp for just about everything you could hope to learn as an entrepreneur, but no one really seems to focus on how to mentally survive entrepreneurship.

It bothers me that we just take stress as a given. Why does fundraising have to be stressful? You know the possible outcomes. You're either going to make it or you're not. You know what happens when you don't. You could go out of business. You won't die. You're not likely to become homeless.

Disappointing for sure, but does it need to twist your head into such knots that you get physically sick over it?

I can't say I stress out about anything. That's not so say that I don't care about things. I do care--deeply. I just don't get into the habit of experiencing anxiety or mentally locking up in the middle of the most uncertain or difficult times.

That's the key--it's a habit. I fully believe that habits and training can meaningfully impact your physical experience. They say that entrepreneurship is a marathon, not a sprint, but it feels like few people marathon train for it. If they did, they'd be a lot more focused on enduring--being able to last the daily wear and tear--than going as hard as they can all the time. That includes mentally. The more mental defenses and best practices you built up, the easier it will be to survive the journey over the long haul.

Here are a few things that have helped me:

1) Take care of your physical self.

Your brain lives in your body.

It's been proven that exercise, eating well, and getting sleep improves your mental state. It's simply something you have to [...]

What Future for Accelerators? Bothsidesofthetable Dec 14, 2014

Accelerators have had quite a good run the past 5+ year […]

A Few Funny Characters You'll Find In Silicon Valley

A Few Funny Characters You'll Find In Silicon Valley Onstartups Dec 15, 2014

The following is a guest post by Nathan Beckord. Nathan is co-founder and CEO of Foundersuite, a San Francisco-based company developing the ultimate collection of software tools and templates for entrepreneurs.

Congrats to Backupify! A Great Exit Story for the First Company I Ever Backed Thisisgoingtobebig Dec 11, 2014

Today, Backupify announced that it is getting purchased by Datto. It's a solid exit to a company that has lots of revs, is growing, and together will form a very formidable player in the data backup space--one that can definitely be a public company in the next couple of years.

I'm super proud of Rob, Ben and the whole Backupify team--and this is particularly special for me because Backupify was the first investment I ever made as a VC, and the first board I ever sat on.

In fact, my history with Rob and Backupify goes back almost ten years, well before the idea of cloud backup was ever a glimmer in anyone's eye.

I started reading a great blog called Business Pundit in 2004. It was written by a guy about my age down in Louisville, Kentucky. A former engineer, Rob was a great writer and a thoughtful student of management. I don't remember when I started talking to Rob, but I know it was before February of 2005, because I found "" in the contacts I ported over when I left GM and went to USV.

We used to chat a fair amount via our respective blogs about management and entrepreneurship. He was an interesting guy and I watched him throughout a bunch of interesting projects, like a complete open source business where all the employees got to make the decisions.

I didn't actually get to meet him in person until SXSW in 2007. That was the year Twitter took off.

I took this picture of Rob, Michael Galpert, and Danny Wen of Harvest. Even then, Rob was an optimizer, trying to map the best routes around Austin.

I liked meeting Rob so much that when I drove across the country that summer, I made it a point to go visit him.

We stayed in touch and I got to know a bunch of the Louisville startup and creative crew, like Todd Earwood, Matt Winn, and Ashley Cecil.

Rob messed around with some local video thing in 2008, which everyone but Rob thought was a pretty terrible idea. Later that year, I sent a tweet that inspired a company that in [...]

Ten Good Reasons to Take Venture Capital Money Thisisgoingtobebig Dec 9, 2014

Following up on my post from Monday that rang like "reasons not to take VC money" here are some reasons you should:

1) You really like the investor and believe they can add more value than you give up in equity.

2) You are growing, and if you don't raise, you won't be able to build the infrastructure required not to come apart at the seams.

3) You have the team in place or identified to build the product, you've done your homework by talking to customers that it is, in fact, the right product, and you're the best person to lead the effort, but you can't fund the build of the product yourself.

4) You've identified the best team, and while they're asking for reasonable startup salaries, you can't afford to hire them quite yet.

5) You've figured out how to get a sales funnel going, the flywheel is turning, you've got positive ROI on incremental salespeople or customer acquisition dollars and now you want to put gas on the fire.

6) You're on your way to building a network effect, you know how you'll likely make money because you've spoken to lots of potential sources of revenue, but can't monetize without critical mass.

7) You're making a ton of money at the company level, but haven't really ever made any money yourself personally. Might be time to let someone you want to work with buy your equity.

8) You're doing something disruptive that is going to have some regulatory or other kinds of hurdles that require human hours of changing the playing field.

9) You're doing something physical in the real world that just requires a certain amount of capital overhead.

10) You're doing actual science and R&D to build something that doesn't exist yet, but could have a huge outcome.

Ten Realities of Taking Venture Capital Money Thisisgoingtobebig Dec 8, 2014

If you take venture capital money...

1) You increase the chances that you may not be CEO of your own company one day--and that also might be the best thing for its long term success.

2) You are signing up to sell the company one day--to another company or to the public market, but definitely to someone.

3) You will almost certainly take more venture capital money after that.

4) You will almost certainly go cashflow negative, increasing the risk that your company will fail.

5) You now have the responsibility to report the progress of the company to others--and to consider their opinions and feedback.

6) You have prioritized growth and your company will be bigger next year than it is now.

7) Some of the people working for and with you now will not be suitable for a growth phase and will have to leave.

8) There are smaller exit opportunities you will not be able to take because your capital structure makes them financially unattractive.

9) You will own less and less of your company over time as you take on additional investment.

10) You will face more competition as venture investment signals that what you're doing may be attractive.

Why I’m Standing Today with My Black American Friends, Family & Colleagues

Why I’m Standing Today with My Black American Friends, Family & Colleagues Bothsidesofthetable Dec 4, 2014

. “It stops today.” I spent the entire day […]

If You Don’t Respect Your Customers You Won’t Be Successful Bothsidesofthetable Dec 7, 2014

I spend a lot of time with startups and thus hear many […]

Because the Domain Makes it Really Real Thisisgoingtobebig Dec 2, 2014

Three years ago today, I grabbed the domain name

It's kind of a funny answer to "When did you start Brooklyn Bridge Ventures?"

What might be a more relevant date is May 22nd, 2007. That's the day I sat down for lunch at Coffee Shop with Henry Blodget, just six days after Silicon Alley Insider launched. Henry told me that I should start a fund--me, a 27 year old former VC analyst turned product manager with no MBA at a startup that wasn't really headed in any particular direction. It's probably the first time I'd really ever had the thought of starting my own fund.

So thanks for playing Inception, Henry.

I guess it's true what they say. It's easy to be right about market predictions eventually. It's just really hard to predict timing.

The stories we tell ourselves about how things get started are often much more linear than they actually happened. Who had what idea when? When did you actually commit to something?

Getting a domain name... I guess that's about as good a demarcation line as any, but that's never really the full story.

So when did I really start Brooklyn Bridge Ventures?

Well, I was born in 1979.

My godfather got me IBM stock right after that, so that's how I knew that a stock market and investing existed.

My dad brought home an IBM PS/2 in 1987.

I got an internship on the buy side at the GM pension fund in high school--in 1997.

I started a business newspaper in 1998 in college covering the stock market and the economy.

I got my first job in venture--at GM--in February 2001.

I tried to write a book for college kids in 2002-2003, couldn't get it published, so I started blogging in February of 2004.

I met Brad and Fred in the Summer of 2004, agreeing to join them later that year--my first job at a fund.

I started a company, failed at it, and joined First Round in 2009 to help them open up their NYC office. In the middle of that whole thing, I wrote a blog post about Foursquare that [...]

Some Rules for Marketplaces and Distributed Workforce Platforms Thisisgoingtobebig Dec 1, 2014

I've been getting involved with a couple of different models related to labor marketplaces and platforms lately. My interest dates back to my 2010 investment in chloe + isabel back when I was with First Round. I was still at FRC when we invested in TaskRabbit and Uber, even though I wasn't on those deals. I've also run about 30 Kitchensurfing dinners across NYC for tech and startup folks in the last two years. My two most recent deals involve a distribution of labor or direct sales, and two of my upcoming deals are similarly structured.

Yet, I'm quick to turn many of these types of deals down, too--and I've started noticing which ones I like and which ones I'm less interested in.

Here are my two main rules:

1. The labor supply has to get enough out of the platform not to want to go around it.

Your Handy cleaner is undoubtedly going to want to get paid directly if you seem satisfied with them for sure--and why not? Once you like them, you'll just want them to show up at the same time and day each week or every other week or whatever. The platform is providing little value after the initial intro.

This is highly unlikely to happen with your Uber driver, however. Who knows where they'll be the next time you need a cab, and you're not likely to use the same driver twice. In this case, it's not about the cash, but about their ability to replicate the volumes off platform.

Recently, I've gotten interested in two models where the marketplace was cutting the provider in for a slice of the sales, whereas they used to just get paid a flat, hourly wage. Being on the platform would be a huge boost to their net income.

2. You need to get a nice chunk of the transaction to make it worth it as a marketplace.

With some platforms, I can't help but think that a heck of a lot of human effort was expended to net the platform not a lot of cash. If you're only taking a small cut, you've got to have huge volumes to make up for it, and that just takes a long time.

The Very First Startup Founder You Need to Invest in is You

The Very First Startup Founder You Need to Invest in is You Bothsidesofthetable Nov 30, 2014

  This week I wrote about obsessive and competitiv […]

Why I Look for Obsessive and Competitive Founders

Why I Look for Obsessive and Competitive Founders Bothsidesofthetable Nov 26, 2014

  Obsession. The drive to succeed at all costs. Wh […]

What Salary Means Thisisgoingtobebig Nov 24, 2014

When I was coming out of college, working in finance, I used to think a lot about my salary. I wanted the best offer out of my classmates. I wanted the biggest signing bonus. I liked maxing out on raises and I liked the feeling I got getting to a six figure salary.

The funny thing was that I didn't even particularly care about the money itself. It was, in my mind, what the salary meant. It was a way of measuring performance. It was score keeping.

I missed the bigger picture of the other things that should go into career score keeping--autonomy, growth paths, equity/revenue sharing, the ability to gain public visibility, opportunities for learning, network building, etc.

As an investor, I get very involved in the hiring process of some of my earliest stage companies. One thing that comes through consistently is that salary--specifically how someone goes about the salary negotiation process--can be a consistent predictor of performance.

Nearly every time a company I've seen has had to stretch to accomodate someone's base salary, the person hasn't worked out. When canidates have had the opportunity to choose between more equity and more salary, the people who equity greedy versus cash greedy tend to be better fits for a startup. And when things at a startup aren't going well, it's your best employees that show up first with offers to cut their salary.

That isn't to say that you should accept getting underpaid just because you work for a startup--but acknowledging the reality that, especially early on, dollars given to you shorten the potential lifespan of this company, is key to understanding how things work.

At the end of the day, we could all make a lot more money at hedge funds and banks anyway, right? But, we value other things. We score keep in other ways.

Founders, I think the best thing you can do with your earliest employees is to be transparent. Show your employees how their salary effects the finances of a company. If someone looks at tha [...]

In Defense of Uber: An Objective Opinion Bothsidesofthetable Nov 23, 2014

The story on Uber has been written about ad nauseam, wh […]

The Day I Had To Wear Pants To Ring The IPO Bell

The Day I Had To Wear Pants To Ring The IPO Bell Onstartups Nov 20, 2014

It's #TBT. It's been a busy and exciting several months.