To Expa and Beyond

Originally posted at Expa and covered in more detail at Techcrunch:

I’m happy to announce that I’m joining Expa as entrepreneur-in-residence and advisor in San Francisco. Expa is a startup studio that develops and launches new companies. I will partner with Garrett, Naveen and the team to accelerate existing projects at Expa and launch some new ideas as well.

I spent the last year helping great entrepreneurs build and scale amazing companies as an investor and advisor via 10e9. I will continue to work with those founders and selectively work with a few others on that platform, but my focus will be on building here at Expa.

From pencil to bits, I’ve always enjoyed translating ideas to implementation in different mediums. As co-founder of AddThis, I was fortunate to collaborate with an amazing team to create and deliver publisher tools to over 14M websites reaching 1.75 billion people. The Expa team are true craftsmen – from Foursquare to Uber, they’ve created iconic products used by millions of people worldwide. I’m excited to embark on my next creative journey, building world-changing products with the Expa team.

Uber, Google and Inspiration.

I’ve taken a bit of a break from writing on this blog. I’d like to get back into writing more regularly. Hopefully this blog is a major outlet for that. In an attempt to kick-start the habit of posting here, I thought I’d pull together some stuff I wrote on Medium and HuffPo recently.




Bitcoin – the New Standard for the Black Market?


Bitcoin has big challenges ahead, but it also has big promise.   While the economic rationale from leveraging Bitcoin commercially is sound, the success of Bitcoin will ultimately be driven by its traction in a single market – the Black Market.

Many speculate that Bitcoin will gain mass adoption in volatile economies.  That said, the largest economy that has a pain point Bitcoin can address is the one you don’t see every day.   The Black Market may seem like the stuff of movies, but it’s real.  And it’s big. From narcotics to software piracy, a lot of money is exchanging hands without governments being involved.   Economists have long debated the size of this market.   Author Robert Neuwirth estimates this market to be $10 Trillion in size.   That’s trillion – with a ‘T’.    The largest national economy in the world by nominal GDP, the United States, is valued at $15.7 Trillion dollars.  That would make the Black Market economy the second largest in the world.

By definition, the participants in this economy need anonymous currency.  Today, they use mediums like cash and gold.   Wouldn’t it be great if they had a digital equivalent?  Enter Bitcoin.  If Bitcoin can capture 10% market penetration by making life easier for System D residents, that will make the market for Bitcoin nearly $1 Trillion US.   This is nearly 1000X times the size of the existing market for Bitcoin today.   More interestingly, perhaps, is that market would be almost as large as the sum total of all US Dollars in circulation today.

According to Neuwirth, this shadow economy – sometimes called System D – employs over 1.8 billion people world-wide.  This is nearly half of the working population.   If you assume that the participants in System D will interact with other folks in the ‘light economy’ that means Bitcoin will also have a lot weight behind it from legal vendors hoping to cash in from customers ‘living’ in System D.    This could push Bitcoin over the edge and make the market for these digital bits larger than that of the US Dollar.

It will be interesting to watch how Bitcoin adoption plays out in this market.  Today the Bitcoin market is nearly $1.4 billion – roughly the size of the economy of Belize.   It has a ways to go in value before it hits the mainstream, but if I were Ben Bernake, I’d definitely keep an eye on it.



Bitcoin’s Trillion Dollar Challenge



Bitcoin is all the rage.  Heralded by some as the third wave of currency, this new P2P network+currency is being hailed as a disruptive force not only to the payments space, but as an existential threat to the idea of modern government.   And currency disruption is a big deal.   There are over 3 trillion US Dollar, Euro Coin and Yen in circulation today.  While Bitcoin represents a massive economic opportunity, ranging from trading to Bitcoin mining, the market has to overcome a fundamental hurdle before it becomes a real currency – volatility.

While there is undoubtedly fluctuation in currency exchange rates, major currencies – for the most part – are relatively stable.    This stability is fundamental to the idea of any currency.   You want to know that you can purchase an iPad today, for the same amount that you can purchase it tomorrow – right?   Today, it’s not uncommon for Bitcoin’s value (versus the US dollar) to fluctuate as much as 10% in a single day.   To put this in perspective, the US Dollar vs. EURO fluctuated a little less than 3% in the last month.    This relative stability in value is critical to the future of Bitcoin.

The rate of adoption of Bitcoin as a currency will be a function of the rate of acceptance of the standard by storefronts – both on and offline.   If the currency can fall, or rise in value dramatically, it will be exceedingly difficult for stores to charge using the currency as its relative value vs. standards such as the US Dollar will be flux for consumers.  If Bitcoin continues to realize any further traction, however, there will be more flux in this marketplace before there is less.   The total value of the market today is $1.4B US and growing.   It is an imperfect market characterized by a lack of liquidity.   This will attract hedge funds and other large institutional trading firms seeking mass-scale arbitrage opportunities to move the proverbial needle financially.   And as they enter, it will be nuts.  They will try every trick in the book to monetize this market.  Pumping and dumping the currency for example, might be a huge opportunity in the short run.  Or, perhaps, we will see them start to create and trade derivatives.  These markets are not regulated so it will be no holds barred.

There will be some rocky times ahead of the Bitcoin market.  Until the volume and value of this marketplace is sufficiently large such that it tends toward a more ‘perfect market’ in the macroeconomic sense, it will be difficult for the currency to hold water in the consumer retail ecosystem.  Moreover, it’s unclear that – even with time- it will be possible for an unregulated market to survive and thrive.

With that in mind, the major geographic markets where Bitcoin can likely burst out of the gates are those characterized by instability – third world countries.   Many of these countries are going ‘mobile-first’ in terms of their web infrastructure and have significant unbanked populations.   As a result, some countries – such as Kenya – already have a 1/3 of their GDP and growing running through mobile payments platforms.

In short, all the excited venture capitalists getting ready to pour money into Bitcoin-related opportunities had better buckle their seat belts – it’s going to be a bumpy ride.


Thumb Pay


From Square to Google Wallet, the race is on to remove your wallet from the payment equation. I’m excited for this future, but am already eagerly awaiting the next natural step in payments – biometric payment networks.

I’d love it if retailers had a hardware/software platform that leveraged some combination of biometric data – such as a finger print coupled with an image of my face – to enable me to purchase goods and services. For concerned citizens that want additional security, you could even have an optional password to provide some extra peace of mind.

Imagine not having to worry about carrying credit cards, phones, etc. The world would be at your finger tips – literally. There are some places where this concept is being tested, but we’re a long way from this become commonplace.

The same technology could be applied to other areas, enabling you to access a number of other authenticated services beyond payments. You could access web services that manage your photos, videos, documents, and more from any device, in any location.

Inevitably, the world would need to become comfortable with the idea of accessing a cloud-based identity platform using their biometric data. Privacy and security are clearly concerns that need to be addressed, but it is possible.

Using a device to pay is cool, but using nothing is cooler.


Christmas Card in Code


Was feeling nerdy and holiday-ish.  Couldn’t hit everyone up with my love, so please follow this psuedo-code to get your personalized holiday greeting. Enjoy!


int friend = size.friendList();

while (friend > 0){

System.out.println(“Dear, ” + getName.friendList(friend));

if (getReligion.friendList(friend) == ‘Christian’){

System.out.println(“Wishing you a Merry Christmas!”);



System.out.println(“Wishing you a Happy Holiday!”);




System.out.println(“Have a wonderful 2013! Love, Me”);



Big Money, Big Following: Net Worth of the 20 Most Followed People on Twitter


What do the top twenty Twitter users have in common?  They’re rich – like really rich.

I recently spent some time on Twitaholic, curious to see if there was a common thread among the top twitter accounts.  Upon inspection there was one fact that stuck out.  The mean net worth of  the twenty top accounts (excluding companies) was $230M.  I found the net worth info on Celebrity Net Worth. The median was $85M.   Selina Gomez (#19) at brought up the rear at $4M, while Oprah Winfrey (#12) led the pack at $2.7B.    Also of note was Barack Obama (#5) who is worth a cool $11.8M.

It’s not enough, however, just to be rich.  Bill Gates is one of the richest men in the world and is ranked #37.    You need to be actively in the spotlight.   Of the top people on Twitter ALL of them are regularly in the media with professions in entertainment and sports.

It’s interesting to note that only two of the top twenty accounts were companies – YouTube and Twitter.  Both are multi-billion dollar assets.

The lesson in terms of building your following?   Spend less time gaming the system and more time taking charge of it.  Monetary success translates into social media influence.    And it doesn’t hurt to be on TV. :)

Check out the Rich and The Twitter-tastic below.

Twitter Rank*


Net Worth**



Lady Gaga




Justin Bieber




Katy Perry








Barack Obama




Britney Spears




Taylor Swift












Kim Kardashian




Nicki Minaj




Oprah Winfrey




Ellen Degeneres








Justin Timberlake




Cristiano Ronaldo








Bruno Mars




Selena Gomez




Ashton Kutcher




* Source: Twitaholic

**Source: Celebrity Net Worth(Amounts in millions)

20 Things I’m Thankful for as an Entrepreneur

I’ve had the good fortune to have some time on my hands of late. And like the child of two psychiatrists should, and is uncontrollably compelled to do, I’ve spent a great deal of time reflecting on my experience.  AddThis (formerly Clearspring) was not only my first start-up, but was also my first job.

It’s been an incredible journey. Since getting funded in 2006, we’ve raised nearly $70 million dollars. With that funding we’ve built the largest social sharing and targeting platform used by 14 million web sites reaching 1.3 billion unique users, seen our revenue grow into the millions, and – most importantly – built an amazing team of 100 people across the country. So, it’s probably worth some cycles processing the experience.  I’ll be writing a couple of posts this summer related to this topic, but I think it’s best to start with a bit of humility.

I’m blessed. All entrepreneurs, no matter how successful, are also blessed. Building a company is a unique experience – a gift. It shows us the potential of our world and our ability to transform that potential into something great if we simply have the courage to take a shot. For this, I’m truly thankful.   Sometimes I think we all get so caught up in the outcome, or competition, that we forget the inherent reward earned while undertaking the spiritual quest of entrepreneurship.

With that in mind, I thought it’d be appropriate to start with the 20 things I’m most thankful for as an entrepreneur.  This was a bit tough, but think I hit the 80/20.

  1. A chance to make a dent in the universe
  2. Family that believed
  3. Friends that cared
  4. Customers who’d try
  5. Team that would go the extra mile
  6. Investors that made a bet (and then another)
  7. Mentors that provided flashlights
  8. An education of extremes
  9. Feeling the value of cash
  10. Building the courage to ask for the sale
  11. Learning humility from my (many) failures
  12. Gaining confidence from my (few) successes
  13. Understanding my limitations
  14. Learning to trust in others
  15. Finding out that anything’s possible
  16. Appreciating the mess
  17. Developing the skills to build something from nothing
  18. Learning that when in doubt, move.
  19. Realizing I can do better
  20. Having the health to take another shot

Looking Back – You’ve Got Mail


Like many people, I’ve been spending time reflecting on the past year as I set my goals for 2012.  Also like most people, I’m working with the television in the background. Right now, I’m watching ‘You Got Mail.’   Yes I like romantic comedies.  Laugh it up.   As it happens, this movie is strangely appropriate given the reflective exercise that I’m now undertaking.

For the uninitiated, the premise of the movie is how two people meet and fall in love online via AOL , while – in the real world – they battle it out professionally.  The male lead played by Tom Hanks operates a massive chain of book super stores (think Borders).   Whereas the female lead played by Meg Ryan is the proprietor of a small shop that is threatened by the expansion of the super store.

The film was released in 1998.   It’s funny to observe just how much has changed since then.  AOL is no longer the center of the online universe.  The book superstore model that was then at its peak is now bankrupt.   Couple that with the fact that this was one of the last classic Tom Hanks and Meg Ryan romantic comedies to be released and I officially feel old.

Even though the world has changed, much remains the same.  We all want to connect and share our lives with people – we just do it via Facebook, Twitter and cell phones.  We all want to learn and be entertained via books, we just happen to buy them via e-readers.   And – perhaps most importantly – we all still want to be happy.

So as you reflect on how much has changed and your life on the go-forward, don’t forget to pay attention to all the simple things that make life great.