Redeye VC

Josh Kopelman

Managing Director of First Round Capital.

espite being coastally challenged (currently living in Philadelphia), Josh has been an active entrepreneur and investor in the Internet industry since its commercialization. In 1992, while he was a student at the Wharton School of the University of Pennsylvania, Josh co-founded Infonautics Corporation – an Internet information company. In 1996, Infonautics went public on the NASDAQ stock exchange.

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Monthly Archives for 2010

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Sharing and Exchanging...

DSC_0021 Yesterday was one of my favorite days of the year.   Not because Steve Jobs unveiled an iPod with a 9 inch screen.  Not because it was Obama’s First State of the Union Address.  Not because of any earth-shaking pronouncement made at Davos.  But rather, because it was the First Round Capital CEO Summit.  It was the one day each year where all of the CEOs/Founders of our portfolio companies come together in one place.   It was an amazing experience for me – to see so many smart people in one room.  Exchanging ideas and sharing experiences.  Doing deals with each other.  Asking each other for help.

I know that in addition to being cash constrained, the typical entrepreneur is even more time constrained.  And asking our entrepreneurs to spend a whole day of their time away from their office is asking them to make a big time investment.   And judging from the responses we’ve seen so far, I think the day was a success all around. 

One of the benefits of having a fairly large portfolio is that our portfolio companies can offer a lot of value to each other.  Whether it is sharing interview techniques, technical management strategies, sales leads, perspectives on the advertising market, or doing deals - it is always great to see portfolio companies helping each other succeed.  And now, I'm excited to announce that First Round Capital entrepreneurs also have the potential to benefit economically from  each others success.  That is because yesterday we unveiled the First Round Capital Entrepreneur's Exchange fund.  This exchange fund was created to allow First Round Capital entrepreneurs to contribute a small piece of the stock they own in their company  -- and share in the upside of all the other companies.  The fund is only available to qualified First Round Capital portfolio companies and First Round Capital does not receive any economic upside from the fund.  The goal of the fund is to allow our entrepreneurs to get the benefit of some tax efficient diversification without giving up their upside prematurely. 

When I was an entrepreneur, I remember the feeling of having all my eggs in one basket -- and it is our hope that this fund will remove some of that stress.  Now our entrepreneurs can get the same diversified portfolio that our limited partners get (with better economic terms) and receive a financial benefit when other First Round Companies exit (even if their own company is still years away from an exit).  I'm super excited about this fund -- as (I think) it is the first time that a VC firm created an exchange fund just for their entrepreneurs.  In addition to allowing our entrepreneurs to exchange their shares into the fund, I believe this fund will result in more sharing and exchanging of ideas and assistance between the companies.

I really want to thank the entire First Round Capital team along with our outside speakers and resources for putting on a great CEO Summit: Dick Costolo, Eric Ries, Jeff Jordan, Mike Marquez, Peter Kafka, Ethan Beard, Ted Wang, Satish Dharmaraj, Andrew Chen, Chris Mahl, and Andy Getsey.

My lawyer pestered me to add this dislaimer:  This is not an offer to buy or sell securities in the First Round Capital Entrepreneur's Exchange Fund.  In fact, even if you wanted to participate in the fund you couldn't (unless you were a qualified First Round Capital entrepreneur).

Finding the dreamers...

Susan Boyle was a dreamer.  She believed in her talent -- and just needed a platform to help the world hear it.  This past year we saw what can happen when the right talent is combined with the right platform.  Susan became a viral hit -- with over 80 million views on her YouTube video.  And this past week her debut album smashed all records --racking up the biggest one-week sales total of the year, and the highest debut ever for a solo female artist.

Well, Susan's not the only one with talent.  We are fortunate to work with a pretty amazing group of entrepreneurs.  A talented group of people -- who dream big dreams.  And we're happy to present First Round Capital's annual holiday video to demonstrate it.  

Happy Holidays!

First Round Capital 2009 Holiday Card from First Round Capital on Vimeo.

Let's just add in a little virality

It happens all the time.  I’m meeting with an entrepreneur, who is telling me about a really innovative product idea for a consumer website.  And I’m liking it.  We’re going back and forth on product ideas.  And before I know it, we’re approaching the end of our meeting.  I then ask them, “So, how are you going to acquire customers.”  And that’s when it happens.  That’s when I realize that they’ve spent all their time focusing on the product/site, and aren’t nearly as innovative when it comes to their customer acquisition plans.  They view marketing as something they can “bolt on” afterwards.

The most disappointing answer is when they say “Oh, we’ll just make it viral.”  As if virality is something you can choose to add in after the product is baked - like a spell checker.  Let’s imagine the conversation at the marketing department of the wireless phone companies.  “Let’s see.  Should we spend $4 Billion on advertising this year…or should we just make it viral?”.

Virality is something that has to be engineered from the beginning…and it’s harder to create virality than it is to create a good product.  That's why we often see good products with poor virality, and poor products with good virality.  The reason that over $150 Billion is spent on US advertising each year is because virality is so hard.  If virality was easy, there would be no advertising industry.

That’s why First Round Capital’s website has always said: “Too many companies treat marketing and sales as a tactical afterthought. We believe marketing is strategic and seek companies that are marketing focused – with marketing requirements driving product development.”

Customer acquisition (also called distribution) is the number one challenge facing consumer web properties.  And that's why I'll be digging in deep on this subject through a series of blog posts where I hope to focus in depth on the challenges (and opportunities) in customer acquisition…  Up next:  "Business Development and Distribution"

VC - Back to the Future?

I just came across a great report by Industry Little Hawk entitled the Venture Capital Rebound (pdf).  In the report, the authors reach a similar conclusion to Paul Kedrosky (read Paul's great research for the Kauffman Foundation here) -- that too much capital has gone into venture capital.  Paul has argued that we need to shrink the amount of venture funding by 50% -- a statistic that almost every VC agrees with.  (Ironically, 100% of VCs would argue that their fund should be in the half that survives).

What is refreshing about the Industry Little Hawk white paper, however, is that they don't just advocate reducing the capital allocated to venture.  Instead, they advocate allocating capital to smaller funds.  And they articulate a number of reasons for their position (smaller funds are better positioned for the current exit landscape, better alignment with entrepreneurs (per my last post) and with limited partners, etc).

The "money stat" from the paper is that in the 1980's there were just 12 venture funds above $250M.  Today there are over 408 - and 30 over $1B.  And most of this fund-size growth took place in the last 10 years.  The chart is below:


What is interesting to me is that the proposed solution isn't a radical change.  It isn't a novel idea for re-structuring the industry.  Rather, it's a realization that venture should go back to it's roots.  So I spent some time researching the origins of many leading venture firms.  And I was surprised to see that they all started with small funds.  While venture is far from perfect, and can always improve, maybe we should spend less of our time working on "new solutions" to the "venture is broken problem" and spend more time working on old ones.

The data speaks for itself.  My favorite factoid: the initial funds of Accel, Kleiner Perkins, CRV, Mayfield, Venrock, Greylock, NEA, TA & Sequoia COMBINED were under $125M!  And even on an inflation-adjusted basis the average fund size is $55M.

VC sizes

Note: I pulled data from the web and from Udayan Gupta's book Done Deals -- if you think I have incorrect data, or you have missing data, just leave it in the comments and I'll update the post. 

UPDATE:  Thanks to Kent Goldman for running the numbers through an inflation adjustment tool.

Company Math vs VC Math

Fred Wilson has a great blog post today entitled The 'We Need to Own' Baloney.  In it he discussed the fact that many VC's apply arbitrary ownership thresholds to investments.  I couldn't agree with Fred more - but I'd take it even further.  This is not just limited to ownership requirements.  Rather, VC's often impose "VC math" on companies in three areas:

  • The amount VC's "need" to own
  • The amount VC's "need" to invest
  • The return VC's "need" to generate certain exit returns

These "requirements" are a direct result of the mathematical model that venture funds are optimized for.  And as fund's have gotten larger, their math has gotten more difficult.  We're now witnessing the conclusion of a "10 year experiment" where money invested in venture funds has exploded and fund sizes have more than tripled in size.  A decade ago, 75% of all venture funds raised were under $100 million.  In 2007, fewer than 25% of all venture funds raised were under $100M.  And I don't think it's a co-incidence that VC performance has fallen off a cliff during this time period.  Indeed, we're approaching a point where the 10-year return in venture capital is negative.  Paul Kedrosky recently authored a paper for the Kauffman Foundation which discusses this in great detail and proposes that the venture industry needs to be "rightsized" -- and suggests a 50% reduction.  It's a great paper -- but if you don't have time to read it, the money chart is below:


Fred Wilson has previously written about the VC math problem -- but he approached it from the macro/industry perspective.  I agree, and think it's even more scary when you look at it from a micro/fund perspective.  Take a $400M venture fund.  In order to get a 20% return in 6 years, they need to triple the fund -- or return $1.2B.  Add in fees/carry and you now have to return $1.5B.  Assuming that the fund owns 20% of their portfolio companies on exit, they need to create $7.5B of market value.  So assume that one VC invested in Skype, Myspace and Youtube in the same fund - they would be just halfway to their goal.  Seriously?  A decade ago, any one of those deals would have been (and should have been) a fundmaker! 

As a result of this new math, VC's end up super-focused on the longbets (or moonshots) and frequently remove optionality for mid-tier exits.  It has, as Super LP Chris Douvos has written, become a game of finding the next Curtis Sharp.  It is because of the challenges of "VC math" that First Round Capital chose to raise a relatively small fund -- allowing us to continue to make initial investments that average $600K. 

I understand the importance of aligning one's time and capital to the upside opportunity, and recognize that there is some minimum threshold of ownership that is required for a VC to commit the time and attention to an opportunity.  Does it make sense for an investor to spend the time and join the board of a company they own 2% of ?  Probably not.  However, the difference between 25% and 20% ownership -- or even the difference between 20% and 10% -- should not prevent a VC from investing in a promising opportunity. 

It is the same "VC math" which drives a VC to seek to deploy a larger amount of capital into a company.  (Often taking a capital efficient company and helping it become capital inefficient).  And it is the same math which sometimes creates a lack of alignment between a founder and a VC around exit opportunities.  I have previously written these issues when I discussed the "unwritten terms on a term sheet". 

A company's outcome should drive VC returns.  When VC's required returns drive company's outcomes, it's a recipe for trouble.

First Round Capital to open NYC office


I believe that as the world has gotten “flatter” over the last decade, it’s created a big opportunity for venture investors who recognized that great entrepreneurs can come up with great ideas in almost any location.  Indeed, over the last several years, First Round Capital has invested nationally and has funded companies in over a dozen states. 

However, I do believe that certain ecosystems provide real leverage when it comes to the hard work of turning those ideas into reality.  Take acting for example.  Despite the fact that Philadelphia has some great theaters (like the Kimmel Center, the Walnut Street Theatre, the Arden Theatre, the Prince Theater, the Forrest Theatre, etc), I’m pretty sure that almost every young Philly-based actor recognizes the unique opportunities to really hone their craft on Broadway or in Hollywood -- and those who have big career aspirations typically move to NYC or LA.

The right ecosystem can take good raw materials and set it lose on a new trajectory.  That’s why Stumbleupon moved from Calgary to San Francisco, why Jimmy Wales moved from Florida to San Francisco to start Wikia, and why Jingle Networks moved from Michigan to Boston.  And that’s why, four years ago, First Round Capital set up our west coast office (led by Rob Hayes) to firmly plant ourselves in the silicon valley ecosystem.  Today more than half of our portfolio is based in California. 

Over the last several years, we’ve found that the New York City ecosystem has been particularly strong for Internet and media-based startups.  In fact, we’ve met hundreds of really talented New York-based entrepreneurs and funded over 10 NYC-based startups in the last few years – including Appnexus, Knewton, On Deck Capital, Pinch Media, DoubleVerify and others.  And while First Round Capital already spends a lot of time in New York, I’m super excited to announce our plans to increase our presence in the big apple by opening a First Round Capital office in New York City (led by my partner Howard Morgan) -- and the addition of Charlie O’Donnell to our team as an Entrepreneur-in-Residence (EIR).

The obvious strength of the NYC community was on display in the incredible conversations I had at our Office Hours event at Live Bait and in those between entrepreneurs at Meet-Ups around the city, at ShakeShack, at the quality of entrepreneurs involved in First Growth, and in the NextNY community to name a few.  As we looked for ways to support this community, to listen to and learn from entrepreneurs and to help them build great companies in the city, I could not think of a better way to begin than by working with Charlie as our first Entrepreneur in Residence. Charlie’s belief that great companies are lead by great CEOs but also are born from great communities matches my experience as both an entrepreneur and an investor. His work as an organizer, supporter, and participant in the NY tech scene over the past several years has been amazing and I could not be happier to have him join the First Round team.

As seed stage investors we have the privilege of working with entrepreneurs as they establish the DNA of their business and we hope you will work with us as we put down deeper roots in the city.

A deal that was "mint to be..."

I’m super excited by today’s news that Intuit has acquired for $170 million.


It’s been amazing to watch Aaron Patzer and the entire Mint team transform a rough prototype to a world-class product over the last three years.  As my partner, Rob Hayes (who led our investment in Mint and served on their board of director’s) wrote this morning:


"It has been a short 3 years since we met Aaron Patzer at a STIRR dinner in the Valley.  Seven days after we met, he had a term sheet for his seed round and off he went.  During that time we have had a ringside seat while the company grew from a rough prototype on Aaron’s computer to an amazing personal finance tool with well over 1 million users and critical acclaim... " (Continued here)


I look forward to watching the Mint team continue to thrive at Intuit -- this deal was mint to be.  And while I know Aaron always preaches fiscal discipline, he's now a member of the First Round Capital "blank check club" -- and should he ever start another company, he can come to us to claim it ;-)


Congratulations to Aaron and the entire team!


P.S. – And if you think you’re the next Mint, we look forward to seeing you at a future STIRR dinner – we’ll be sponsoring a bunch of them…

Help me rename "Lifestyle Business"

While venture capitalists pass on companies for many reasons, one of the most common reasons is that they don't think the opportunity is "big enough". 

What does this mean?  It means that even if the company executes as planned, the VC doesn't think the exit will be large enough to generate the VC-sized returns.  This determination is based on the venture capitalist's "fund math" and their expected returns model.  It means that VC doesn't think he will make a big enough return by investing here.

What doesn't this mean?  This doesn't mean that the business is not going to succeed.  It doesn't mean that the entrepreneur will fail.  It just means that the VC doesn't think that the return profile of an investment in the business is a fit for a venture capital investment.

Like all VC's, I pass on many companies that I think will be successful and teams that I really like.  I do so because I think that the economic returns won't move my needle.  (And as one smallest venture funds around, my needle is smaller than most other funds.  And yes, I say this because I am self confident enough to handle the "small needle" jokes). 

However when I do pass for this reason, I try to make sure that I communicate the reason for my decision.  Specifically, I state that while I think the entrepreneur will make money here -- I just don't think I will generate the risk-adjusted returns I need. 

I think the industry places too much of a premium on raising venture capital -- and it has become the default operating assumption for every entrepreneur.  Entrepreneurs can create great businesses -- and have great outcomes -- without raising meaningful outside capital.  Just ask James Hong at HotOrNot, Eric Marcoullier at MyBlogLog, and David Clouse of VRBO.

Part of the problem, I think, is that the technology startup ecosystem seems to be structured so that the goal of every entrepreneur is to raise venture financing.  There is a pretty strong gravitational force that pulls entrepreneurs towards raising VC dollars -- and it's often hard for an entrepreneur to overcome the inertia.

However, I also think that a big part of the problem is that there is no good word/phrase to describe these type of companies.  The only phrase I've heard used is "lifestyle business" -- but I think that is inaccurate and pretty demeaning.  It falsely implies that these entrepreneurs aren't working as hard as those of VC-backed companies.  It falsely implies that these entrepreneurs are choosing a better lifestyle than they would have if they were operating a VC-backed company.  And, as 37signals has written, it condescendingly implies that "A lifestyle business is for the hacks and amateurs while a real business is for the big guns and grown-ups."

I think we need a new word.  Something that isn't demeaning.  Something that doesn't imply laziness or lack of effort. 

And maybe the best way to generate that word is by crowdsourcing it.  Fred Wilson posted a similar challenge in 2006 and it sparked the word "freemium".  And Brad Feld just posted a naming challenge yesterday

So here's my challenge -- help me find a new name for "lifestyle business".  Post your suggestions in the comments.  I've also created a public challenge for this on ChallengePost.  Thanks!

San Francisco Office Hours

I had a blast at our Philadelphia Office Hours.  My partners and I met with over 50 entrepreneurs at our biggest Office Hours yet.  My favorite was being pitched by an entrepreneur who arrived directly from Penn's graduation, still in his cap and gown.

Well, we are hitting the road with Office Hours again.  This time in San Francisco.  Please join us for Office Hours in San Francisco on June 11th from Noon - 2PM PST.  This event will mark two firsts for us.

As with all of our Office Hours events, this is your opportunity to meet with the First Round Capital team and start a conversation about your start-up, your ideas, or yourself.  While the meetings are brief, we've found they are a good way to start a dialog and build a relationship.  We hope to see you at our office...

If you can make it or would like more information, please sign up at

Calling all Philadelphia Entrepreneurs

PhiladelphiaSkyline2 Over the last several months, First Round Capital has held our "Office Hours" events in San Francisco, New York City, Austin and Vancouver.  Well, now it's time to bring it home!  I'm super excited to announce our first Office Hours event here in Philadelphia.  Please join us on Monday, May 18th from 3-5pm at World Cafe Live.

One of the greatest opportunities in college was Office Hours. Every professor held them and suddenly became accessible. It was a few minutes where you could walk-in, sit down, ask questions, develop a relationship and catch a professor in an informal environment. We think the same opportunity for dialogue should exist for entrepreneurs and venture capitalists.  At Office Hours, we'd love to meet with entrepreneurs, people thinking about becoming entrepreneurs or folks who would like to join a start-up.  No agenda needed.  No presentations or preparation required.  Just an opportunity to discuss entrepreneurship and startups.

We've met with 50-60 entrepreneurs at every other city -- let's make Philadelphia our biggest event yet!

If you can make it, please sign up at