I am truly blessed to have been part of the Hot Potato team that was recently acquired by Facebook. It was an amazing experience and I’m excited for the entire team and the amazingness they’ll be building at Facebook. I learned a lot from Justin Shaffer and the rest of the talented team that graced us with their presence at the old Hot Potato office in Williamsburg, now the Makery.

Over the past week, I’ve been asked two main questions, which I’ll answer in this post: 1) Why’d Facebook acquire Hot Potato, and 2) What are you doing next?

I’m not in any liberty to answer the first question knowledgeably (other than what you read in the press), but the main thing I learned from my experience at Hot Potato is that none of this happens overnight.

Entrepreneurs like Justin Shaffer of Hot Potato, Scott Belsky of Behance and Dennis Crowley/Naveen Selvadurai of Foursquare have been “hustling non-stop” at this for the past 5 + years. So, when you read that Hot Potato has been acquired by Facebook, Scott Belsky has a national bestseller, or that Foursquare has recently closed a $20M round. This has been years in the making.

Justin Shaffer was the Senior Vice President of New Media at MLB for 7+ years. He helped build up MLB into what it is today. And from there, he’s been thinking about this location/activities/presence problem for years, which he’ll continue solving at Facebook for over 500M+ daily users. There’s nobody else in the universe that can solve this problem better than Justin Shaffer.

Same thing for Dennis Crowley and Naveen Selvadurai at Foursquare. I don’t need to repeat the story behind Dennis and Dodgeball but Naveen was the Lead Architect at Socialight, which is when he started thinking about the intersection of mobile, locations and “checking-in”. It’s no surprise that Naveen’s experience at Socialight helped with the success of Foursquare as a location based business.

Scott Belsky helped grow the Pine Street Leadership Development Initiative at Goldman, Sachs & Co, which was focused on organizational improvement. Even before that, Scott wrote his college thesis on organizing the creative community at Cornell. From there, he interviewed hundreds of the most creative professionals in the world to help him understand the problem he was solving through Behance. This is a problem he’s been thinking about for the past 5+ years.

All of these entrepreneurs have been solving the same problem for years. They’ve been working non-stop to get to where they are today because none of this happens overnight. A lot of new entrepreneurs think they can quit their job at XYZ company and launch a successful tech startup because it’s the hot thing to do right now, but that’s usually a recipe for disaster.

So, that leads me to where I am today. After working with Scott Belsky at Behance and Justin Shaffer at Hot Potato, I feel that it’s my time to follow in their footsteps. It’s been a life-long dream to start a for-profit tech company with a social mission at it’s core. I’ll be launching an education/learning startup (similar to this TEDTalk) here in New York City, which I believe is going through it’s own technology renaissance.

I’ve always been fascinated with how to flip the traditional notion of education on its head because I believe the biggest problem in our society is that people stop learning when they graduate from school, which is a social problem we’re aiming to solve. We’ll be in stealth mode until we launch, but always looking for talented people to join our product team (design, development, marketing), so please reach out if you’re looking to make our world a better place.

Relentless focus is the key to success for any new business idea. With that said, I’ll be stepping away from professionally competing at the poker table and stepping down from All Day Buffet and The Feast Conference (this year will be my last one!) so that I can focus all of my time and energy on my new social venture. I’ll be passing the baton to Jerri Chou for The Feast, and I’m confident she will create even more social impact through what we’ve already created together.

Over the years, I’ve made a ton of mistakes but I’ve learned that as long as you always morally do the right thing, maximize the happiness of those around you, and stay passionate about what you do – things will always work out for the best.

I’m truly blessed. Thank you to everyone that have mentored me along this journey. Until the next one…

If I had all the time and money in the world, I would spend it on documentaries that create world-shaking change that ultimately shift the ways things are done in culture, society, and the world. My favorite documentaries include The Cove, Food Inc, and The Corporation, and I’m really looking forward to Waiting for Superman, which comes out this fall. All of these documentaries shed an exposing light on things we often overlook – food, business, and education – revealing truths and problems that need to be collectively reformed in order to make the world a better place.

After watching The Lottery, which uncovers the failures of the traditional public school system, I started to think about the shortcomings of the current traditional education system. Since the pinnacle of education is getting into college, I believe higher education has shifted from learning to profit maximization as its core purpose. The pursuit of short-term profit and greed is a common theme in all of the documentaries I have listed, which is what ultimately led to the predicament we are in today.

If I had to produce a documentary, I would shed a light on the inevitable student loan crisis, and the collective action we can do to prevent it from happening.

Much like the Great American Banking Crisis (this is a must read article from RollingStone), I believe we will witness something just as globally shattering with the looming crash of higher education loans. The rising cost of higher education coupled with the diminishing value of college degrees can only lead to a downhill spiral.

But with the credit crisis come signs that the college bubble is bursting, as “consumers who have questioned whether it is worth spending $1,000 a square foot for a home are now asking whether it is worth spending $1,000 a week to send their kids to college,” the Chronicle of Higher Education suggests. Further evidence: The New Yorker aims to deflate creative writing programs, “designed on the theory that students who have never published a poem can teach other students who have never published a poem how to write a publishable poem.” — Freakonomics

Yesterday, the Wall Street Journal published an article that stated that “Americans now owe more on their student loans ($830B) than their credit cards ($827B)… He estimates that $300 billion in federal student loan debts have been incurred in the last four years.”

What?! $300B of the $830B came in the last 4 years?! At this rate, we’ll break 1 trillion in no time. To put this in perspective, the US economy is burdened with $4 trillion of excess mortgage debt, which is equivalent to 30% of GDP (source).

And to make matters worse, the WSJ reports that “defaults on student loans are skyrocketing amid a weak job market for graduates and steadily rising tuition costs. Default rates for federally guaranteed student loans are expected to reach 6.9% for fiscal year 2007. That’s up from 4.6% two years earlier and would be the highest rate since 1998.”

From New York Times: Cortney Munna hoped for the best when she decided to attend New York University. Now she owes $100,000.

The New York Times also wrote a great article titled “Another Debt Crisis is Brewing, This One in Student Loans” which goes over this problem in intricate detail.

Meanwhile, universities like N.Y.U. enrolled students without asking many questions about whether they could afford a $50,000 annual tuition bill. Then the colleges introduced the students to lenders who underwrote big loans without any idea of what the students might earn someday — just like the mortgage lenders who didn’t ask borrowers to verify their incomes.

Ms. Munna does not want to walk away from her loans in the same way many mortgage holders are. It would be difficult in any event because federal bankruptcy law makes it nearly impossible to discharge student loan debts. But unless she manages to improve her income quickly, she doesn’t have a lot of good options for digging out.

One thing to note is that student loan debt is different from credit-card and housing mortgage debt. Student loans can’t be washed away when you file for bankruptcy. “Ditching a student loan is virtually impossible, especially once a collection agency gets involved. Although lenders may trim payments, getting fees or principals waived seldom happens.”

Most students view college loans as “good debt” because they’re hedging it against future earnings. But what happens when you switch careers, get laid off, or work an underpaying job? Do students really want to spend the next 50 years paying off a degree in XYZ that ended up being utterly useless?

Good news is that Obama has already signed the Health Care and Education Reconciliation Act.  ”Student loan reform will mean big savings for the US government, but not much change for students until 2014. Instead of private banks issuing loans guaranteed by the government, the government will now become the originator of the loan. The change will eliminate private banks as “middlemen” in the loan process and will save the US government about $68 billion dollars over 11 years, according to the White House.” However, this seems to benefit the government more than the students in our country…

So, what are some other innovative ideas we can implement to curb the increasing education problem for students? Whether you agree with the value of a college education or not, it needs to be reformed and improved. Below are some initial crazy ideas off the top of my head.

1. 2-year Universities: Who made up the rule that we have to attend college for 4 years? By decreasing the amount of time we spend in college, it decreases the amount of loans a student has to take on, so why not spend the 3rd or 4th year interning at a company? Or building a company? Or traveling around the world? I guarantee that students will learn a lot more by DOING something versus SITTING in a classroom.

2. Student Loan Awareness: Most students do not know the terms and conditions of the loans they take on including the repayment process. All colleges and universities should mandate incoming freshman take a 30-minute “entrance loan counseling” class on student loans. As well as seniors that are graduating to take a short session on “exit loan counseling.” A lot of the criticism of colleges is that they just throw students out into the real world with no preparation. This could be a great start.

3. College Loan Repayment Reform: If anyone files for bankruptcy, the student loan should go along with it.

4. Cultural Paradigm Shift: College is NOT the Answer to Success: Yes, it can be a great start for people in different income brackets, races, for the networking opportunities, confidence, etc. But having a college degree will not ensure that you will be 100% successful, or rake in the money once you graduate. College isn’t for everyone.

5. Adopt the Finnish Education Model and Abolish Tuition for Public Schools: According to Wikipedia, “The Finnish education system is an egalitarian Nordic system, with no tuition fees for full-time students. Attendance is compulsory for nine years starting at age seven, and free meals are served to pupils at primary and secondary levels, where the pupils go to their local school. Education after primary school is divided into vocational and academic systems.”

6. Public Service (great idea from Nathan Hurst): More programs like ROTC whereby the government would pay for your education in exchange for public service (teaching, software engineering, accounting, etc).

7. Halt Education Inflation (great point from Matt Lehrer): The best solution I know of is to halt education inflation (http://bit.ly/anl1hM) at the source: the US government / Sallie Mae. There’s no way tuition would be up 10x in 30 years if there wasn’t a huge, mandated buyer and guarantee on student loan debt. Regulate that better and most of the other problems go away.

These are some initial ideas off the top of my head. Would love to hear more from you guys as I think this is a major problem that needs to be addressed in our society. Fire away!

“I call!”

Those were the last two words that came out of my mouth at the 2010 World Series of Poker. It was Day 3 of WSOP with 1,800 remaining players out of the original starting field of 7,319 (and the top 800 makes the money). The blinds were $1,600/$800 with a $200 ante and I had around $30K left in my stack. Not a lot but enough to make a huge dent in someone else’s stack and double up. There were lots of pre-flop raises, re-raises, and re-re-raises. For those of you that don’t play poker, it’s similar to the scene from The Big Hit with the phone tracer blocker that gets trumped by the phone tracer blocker blocker. In other words, the cards in your hand don’t really matter anymore.

UTG, I get KQo, which I normally never play in early position, but it was the perfect stealing hand, considering I haven’t played a hand in the past 30 minutes (which is an eternity when you’re short stack). People would respect my raise and fold to me right?  I raise to $4,100 which was the opening raise at our table (the least amount you can bet to get people to fold). And if everyone folds, I easily pick up $4,200 for nada. Not bad. I decide to take the risk.

I try to look calm and represent a “strong” hand like AA, KK, or AK. First guy folds. So does the second. Then the third and fourth and fifth. The guy on the button stares at his cards, and stares back at me. He looks at his cards again, thinks about calling or maybe raising, but I give him the “if you raise, I’m putting all my chips in the middle” look and he decides to fold. The small blind folds. Almosttttt there! And the big blind decides to call. Shit.

** Backstory: I’ve been hammering away at this guy all day. Every time I sit at the poker table, I pick 2 people I want to stay away from, and 2 people I can get involved with. This was my numero uno target all day. I think I stole around $20-$30K from him. He had his tells written on his forehead. Unfortunately, this was the one time he decided to stand up for himself. **

The flop comes Qo8s4s. He quickly checks, and I bet $5K thinking he would fold (like he did all day). Surprisingly, he instantly check raised all-in for my remaining $20K. I wanted to punch him in the face for pulling the 2001 amateur internet poker player move on me. I tanked and thought about all the possible hands this guy could have and narrow down that range to a few. I put him on the flush draw or AQ (worst case scenario for me), or JJ or lower (best case scenario). I didn’t put him on a set as he was the type of player that would bet big on his draws and value bets when he hits. I thought about my other option: folding. If I folded, I still had enough chips to double up and wait, but I decided to call. If he had the flush draw, I was the huge favorite to win, majority of the time.

He flips over 9s5s for the flush draw against my KQo on Qo8s4s flop. Woo! The turn came the Ks and river 7d. Busto!

So, there you have it. After playing poker for 3 days, I’m out. Looking back, I’m real proud of how I played and wouldn’t take it back for anything. I made a lot of hero calls when the other player was bluffing. I re-raised when I thought players were weak when I didn’t have anything. I went with my gut in a lot of marginal situations which is how I lasted so long.

Pushing how I played aside, looking back over the project, I’m really proud of our accomplishments. I had three major goals for WSOG.

1) Raise over $100K for various charities. We raised over $150K!
2) Get on ESPN to spread awareness about the project. ESPN wrote an article and did a short video about our project. We’ll also probably be on Day 1 of 2010 WSOP since we all wore lady track suits : )
3) Get the professional poker community on board. Rafe Furst, Annie Duke, Phil Gordon, Phil Ivey, Joe Sebok, Ali Nejad and Andy Bloch stepped up to support and encourage the poker community to get involved.

Wrapping up, I would like to thank everyone that donated on Kickstarter. We raised a little over $5,000 which I matched to get us to the $10K buyin for WSOP. And thanks to all the professional poker players, charities, and everyone else that made this project a huge success. Thank you! I could’t have done it without all of you.

Until next year…

“Good fortune is what happens when opportunity meets with planning.” – Thomas Edison

Recently, I gave a talk at the Harvest Hobby event about poker, risk taking and decision making. While giving the talk, I slowly realized that no one in the audience really cared about the intricate strategies behind  poker. Terms like “check-raising” and “sucking out” didn’t really resonate with a crowd of non-poker players. Then I quickly realized that the audience related to the real life examples that I gave near the end about decision making and relationships (DUH!), which is what inspired this article I’m writing tonight. (Also, I can’t take credit for the thoughts below as everything I’ve learned were based on mentoring from Annie Duke & Rafe Furst). So, here we go!

Wikipedia defines decision making as “the mental processes resulting in the selection of a course of action among several alternatives.” Pretty obvious right? Poker is a game of decision making under conditions of uncertainty, which is caused by chance and imperfect information.

The higher the uncertainty, the higher the risk, so your goal is to reduce uncertainty.

There are 1,326 distinct possible combinations of hole cards your opponent might be holding. If you can narrow that to a range between 10-20, you’ve allowed yourself to make a better decision by reducing uncertainty. You’ll never *know* what they’ll have, which is why poker is mathematically unsolvable, but as long as you make good decisions in the long run, you’ll be a winning poker player.

In life, your goal is to reduce uncertainty and connect the quality of your decisions with the quality of your outcomes by taking calculated risks. You want to take calculated risks when the upside outweighs the downside.

If you’re completely unhappy with your 9-5 job right now, you’ll still be unhappy 25 years down the road doing that same job on the brink of retirement. This outcome will not change unless you identify what you want out of life, and start taking some calculated risks to get you there. Think about what you’re missing out on life by not taking some type of risk right now. The opportunity cost of possibilities is tremendous!

Taking calculated risks has nothing to do with “losing” because you can always learn from your “losses” and mistakes. Your goal at this stage is to increase your confidence and risk tolerance to try bigger things later.

You can do this by taking small baby steps while minimizing the downside. This could be as simple as talking to a stranger in the street who could end up being your wife, or traveling to an exotic location for the experience. This is why some poker players are comfortable buying in for $100, while others buy-in to a poker game for $1M. They slowly built up their confidence and risk tolerance to get to that level.

So, let’s say you want to be an entrepreneur. You can start by researching, developing a plan, launching a prototype, etc to build your confidence and risk tolerance to swing for the fences later. The goal of your business plan isn’t to convince others that you business is going to work. It’s to convince yourself that your idea is going to work.

Success throughout your life comes from making good decisions by reducing uncertainty and taking calculated risks. The more risks you take in your life, the more chances you’ll have to maximize your happiness and be successful. So what are you waiting for? What risks in your life are worth taking right now?

“There are no original ideas. There are only original people.” – Barbara Grizzuti Harrison

A couple of weeks ago, I met with a passionate entrepreneur who pitched me an idea that he was working on for the past couple of months. He was in the “feedback” stage of his idea, which is when entrepreneurs tell everyone they know about their idea to hone down their pitch, and gather feedback to fill holes in their idea. As we talked about his idea, it resembled another idea that was already launched, which I briefly mentioned. Surprisingly, his enthusiasm went from being extremely excited to utterly disappointed within a couple of seconds. He couldn’t believe that another company was executing something similar to his idea.

At this stage, most entrepreneurs will dismiss their idea because they believe “it’s not original or innovative” enough if someone else is doing it. Most entrepreneurs fall into the trap of killing off their ideas way too early before exploring all of the possibilities that can lead to true innovation.

In poker, there are simple rules you can follow to put yourself ahead of 90% of other poker players. One of my favorite rules revolves around removing any attachment to the value of poker chips. When playing poker, the chips in front of you have absolutely no value, they’re just a medium for you to win chips from other poker players. Most players don’t play their A-game because they’re trying to “make the money” and don’t want to risk losing all their chips (which they end up losing anyways).

Last weekend, Rafe Furst told me a story about Dewey Tomko who is an amateur golfer and professional poker player. Dewey has issued a $1M challenge to any golf pro to a round of golf, which he usually wins for two main reasons. First, none of the professional golfers are used to betting $1M of their own money, so they succumb to the pressure of hitting clutch shots (they are too attached to the amount of money on the line). Secondly, Dewey doesn’t think about the $1M stakes as he’s become immune to attaching himself to the value of chips or bets. Framing the way you play poker with this simple rule can increase your odds of being successful.

I’ve followed a similar rule to frame creativity and innovation: For every idea you come up with, there are probably ten other people in the world executing that same idea.

Once you just embrace this rule, you won’t worry too much about what other people are doing. Just think of it as part of the process of being an entrepreneur. Look at Coke & Pepsi, which are almost identical products but both billion dollar companies. There’s no such thing as original ideas, only original people. Don’t fall into the trap of killing your idea off too early because it can change, morph, and turn into something truly amazing.

Do you have a billion dollar startup idea? Is it going to be the next Facebook, Paypal, or Google? If you’re an entrepreneur looking to raise capital, it’s almost impossible to raise money for a “small” idea that you might find amazing, game-changing, and innovative.

And you know what? It’s not the end of the world if your idea isn’t going to be the next Groupon.

A couple of nights ago, I had dinner with Nick and Thompson who told me about movie directors and their “calling cards” (if you don’t have friends outside of the tech/startup industry, you should start widening your circle because the more people you know outside of your industry, the higher your chance of being innovative and gauging good ideas).

A lot movie directors have “calling cards” which are small budget, creative, and game-changing films that garner interest from major studies to land the big film. The film they really want to do. The big kahuna.  But, in order to land the big film, they need to prove themselves with a film that provides them some exposure, credibility, and experience. You’ve seen this with Quentin Tarantino and Reservoir Dogs, Kevin Smith and Clerks, & Darren Aronofsky and Pi. All of these initial films led them to where they are today.

A lot of entrepreneurs default to thinking about launching the next billion dollar idea (mine is starting an online bank).  The only problem is that most new entrepreneurs don’t have a “calling card” that can help them get their big startup idea off the ground. The next time you have coffee with a successful entrepreneur, ask them about their “calling card”, or better yet, ask them about their past failed ideas. Every entrepreneur has at least one.

Time is your biggest expense, so start your project/idea sooner than later, but don’t worry about launching the next big thing. Put something out there because you’ll learn a lot whether it succeeds or fails.

In the meantime, keep a big startup idea spreadsheet or diary. Who knows? If your “calling card” takes off, you might have to close your eyes and pick one of your big ideas sooner than you think.

Thanks to Nick and Thompson for inspiring this article.

“You are the average of the 5 people you spend the most time with” — Jim Rohn

Are entrepreneurs born, or are they made? A recent Tech Crunch article argues that entrepreneurs can be made based on a $50M research project conducted by the Kauffman Foundation.

“The key is to provide education at “teachable moments” — when the entrepreneur is thinking about starting a venture or ready to scale it.   Highly motivated individuals with “scalable ideas” can be recruited to be entrepreneurs and to be made successful, by surrounding them with a network of other experienced entrepreneurs; sources of money; and mentors.  It is probably education, exposure to entrepreneurship, and networks that led these people to pursue the entrepreneurial path.”

This reminds me of the entrepreneurial story of Blake Mycoskie, who is the Founder of Tom Shoes.  He started his entrepreneurial career at 19 when he started a laundry pick-up business in college. From there, he started an outdoor advertising company, television network, and technology company that provided drivers’ education for teenagers.  These were successes and failures before he started Toms Shoes.  There are two things to note with Blake.  1) He started his entrepreneurial career at 19 (he wasn’t born into an family of entrepreneurs) and 2) all of his companies were stepping stones to Toms Shoes (he failed and learned a lot of times before he was finally successful).

Another great story is the one behind the Paypal Mafia.  What’s interesting about the Paypal Founding Team isn’t what they did at Paypal, it’s what they did after they sold the company to Ebay.  They’ve launched everything from Youtube to LinkedIn to Kiva to launching rockets into space.  How insane is that?  And why?

“You never think it could happen to you,” says Hurley. “But seeing Peter and Max and the guys come up with ideas and seeing how to make things work gave me a lot of insight. You may not have a business degree, but you see how to put the process into effect. The experience helped me realize the payoff of being involved in a startup.”

This story is repeated over and over again. There’s the Google Mafia (another article), 351 Massachusetts Mafia in Boston, and our very own About.com Mafia in New York.

So, one could argue that entrepreneurs are not born, but maybe made over time.  Maybe it’s nurture,  and not nature? And if it’s nurture, is there a way to structure a fund around the concept of “smart money”?  Recently, there have been a lot of great funds that have started in the NYC startup ecosystem including Founder Collective and Lerer Media Ventures, which offers “smart money” to entrepreneurs (investment, experience, knowledge, contacts, etc) as well as financial investment.

Is there a way to create a fund that doesn’t invest any funds? Is there a way to focus on the entrepreneur while traditional funds focus on the company? Can a new fund invest knowledge, experience, networks, and ideas to making entrepreneurs better?

As ideas become cheaper and easier to implement in the tech space, entrepreneurs don’t need millions of dollars to get something out the door. Yes, they’ll still need money to scale and grow  when they gain traction and success,  but what about those entrepreneurs at that “teachable moment” when they just need some guidance?

Here’s how a fund that doesn’t invest funds could work:

1) It would consist of a “class” of entrepreneurs (around 3-4) and mentors (around 3-4).
2) The mentors would all be successful entrepreneurs that have grown and sold their companies ($50M+). The entrepreneurs would be the next up-and-coming class that will probably grow and sell their companies for $50M+. ($50M is some arbitrary number I picked. It could be any measure of success.)
3) The mentors would act as overall advisers for all the entrepreneurs (taking a minimal equity stake), and the entrepreneurs would have a peer-to-peer mentoring network with each other (with a cross-equity option pool for the startups). The mentors can offer advice and knowledge on everything from hiring to personal life/work balance to work cultures. The entrepreneurs would also have access to each other.
4) The overall fund would take a small percentage of equity from the startups.

So, to paint a even more realistic picture.  Here’s an example of how one class would look like. The mentors could be Caterina Fake (Hunch & Flickr),  Scott Kurnit (About), and Scott Heiferman (Meetup) in NYC. The entrepreneurs could be Naveen Selvadurai (Foursquare), Andrew Kortina (Venmo), and Justin Shaffer (Hot Potato).

A very strong thing to note is that this fund would be focused on “nurturing” the entrepreneur versus the actual company. The problems with the actual company would still go to the angel investors, board, and VC’s that invested money into the company. The problems s/he faces with being an entrepreneur would be directed towards this fund (mentors and peer entrepreneurs), with the equity coming out of the personal founder stock.

What do you guys think? Would you take investment from this new fund?

Even more importantly, “if you are the average of the 5 people you spend the most time with,” who are the 5 people you are surrounding yourself with today?

I’m a huge fan of Jonathan Harris.  He’s the creative genius behind We Feel Fine, Sputnik Observatory, and The Whale Hunt among many other projects.  His interview on 99% and talk on TED are my favorites.  And his vignettes about World Building in a Crazy World will blow your mind.

Everyday he has been posting one photo a day beginning on his 30th birthday.  I’ve been reading them religiously everyday and one of my favorites includes the one he wrote on December 17, 2009.

I have been wanting to read some Faulkner, so I visited the Smith Family bookstore in Eugene. I asked the clerk if they had just received a big shipment, but she said that no, that is always how it looks in there. This confirmed my intuition that there are many books.

I would like it if somebody worth emulating would give me a list of the 100 books that I need to read, in order to push and poke at my stiff sense of self until I am larger and more dynamic, expanded like a rubber balloon in 100 directions by 100 well-expressed world views.

With such a list, I would have no problem with a computerless cabin-bound existence, and I would never venture back to the swampland of the Smith Family bookstore, nor any other wetland like it, trudging through printed sprawl to look for pearls.

For the past month, I’ve wanted to write an article on “book swaps” — essentially publishing all of the books I’ve read on my blog, and encouraging anyone to swap books with me.  Instead, I’d like to compile “a list of 100 books that have changed your life.” These can be anything ranging from business to fiction.  If it’s worth reading, please leave them in the comment section below.  I’ve started the list by listing out a couple of books that have changed my life…

1. The Republic of Tea: Letters to a Young Zentrepreneur
2. The Omnivore’s Dilemma: A Natural History of Four Meals by Michael Pollan
3. Life Inc: How the World Become a Corporation and How to Take it Back by Douglas Rushkoff
4. The Fountainhead by Ayn Rand
5. 48 Laws of Power by Robert Greene

My goal is to eventually read through every book on this list in my lifetime.  And share this list with others.  I’d also love to start a book swap so please let me know if you’d like to trade any books as well!

2010 is finally here and I think it’s going to be one of the best years yet.  I have friends traveling around the world, raising money for their startup, and others questioning conventions and the status-quo (hopefully to launch their own startup)!!  As we move into 2010, I thought I would share what I learned in 2009 from the many mistakes I made (there are many) and the mistakes I avoided. My goal is to provide some guidance for younger entrepreneurs because these are all things I wish I read a year ago.  I hope you find some of these useful.

1.  Focus on focusing. I spent the majority of 2009 “incubating” startup ideas and spreading myself way too thin.  Chris Dixon wrote about the trap that many entrepreneurs face with incubators.  ”The appeal is the idea that you can do not just one startup but many, and just focus on the “fun stuff” in each one (idea generation, product features, strategy, etc).”

In 2009, we launched By/Association, TBD, and Lovely Day while growing The Feast and All Day Buffet from the previous year. (You read that right.  I was involved with 5 different companies.)  When things weren’t going as well as planned with a new venture, we just launched a new one.  We fell into the “that’s a great idea, let’s launch something and see what happens” trap.

“People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the 100 other good ideas that there are. You have to pick carefully. I’m actually as proud of the many things we haven’t done as the things we have done.” — Steve Jobs (h/t Caterina Fake)

If I could this all over again, I would have said NO to the majority of projects and ideas. By spreading myself thin over many different projects and startups, By/Association never got the love it needed to take it to the next level (Since then I have stepped down from the other startups to focus in 2010). I learned that success equals 1% idea and 99% execution and perspiration, so focus on the 99%.  Saying no is more important than saying yes.

2.  Biggest cost is time, not money.  My favorite two articles from 2009 were from Caterina Fake titled “Working Hard is Overrated” and “Working on the Right Thing.”

“So often people are working hard at the wrong thing. Working on the right thing is probably more important than working hard. — Caterina Fake”

Working on the wrong things are very, very, very costly for entrepreneurs.  In 2009, I found myself running around like a chicken with his head cut off.  I read almost every article on “re-iterating fast” and how “business plans were dead” so I took the advice and went with the flow and planned accordingly.  It ended in disaster for me.  I ran around in circles. It was like I was driving 90 MPH on the highway without a final destination.  Looking back, I realized that I could have efficiently spent that time moving the ball forward for a plan with an end-point.

Having an end-point is essential for your business and personal goals.  Yes, it can change.  And yes, it probably will change.  But thinking about a strategy will set you in a direction to achieve your goals and milestones.  By committing to something in the future, decision-making in the present becomes much easier.  It’ll save you money.  And make you even more.  That’s a win-win in my book.

3.  Trust you gut.  Timing is everything. We launched By/Association in July of 2009, and it’s been growing and gaining traction every month, which is really exciting.  We have some big plans for 2010 which resulted from two major decisions we made:  1)  We turned down a small amount of investment money; and 2) we didn’t touch the website for nearly 6 months other than fixing bugs and changing marketing copy (this was on accident because of lesson #1).

As many of you know, I play a lot of poker and part of being a good poker player is trusting your intuition.  Most amateur poker players don’t follow their gut, and lose a lot of money in the process.  At the end of the day, the timing wasn’t right for By/Association.  We turned down money because we didn’t know where we were going. There was no plan.  The product/market fit was nowhere close to 40%.  And most importantly, my gut told me to sit back and wait for a better spot to “go all-in.”

If we took the angel investment to build what I thought should have been the next version of By/Association, we would have wasted a lot of time (refer to lesson #2) and built something that would have ultimately been thrown in the trash.  Rather than re-iterating fast, quick, and deploying new versions every 2 weeks; we decided to think about the overall bigger picture by observing trends and talking to our members.  This resulted in a better concept that solved all of the major holes in the older version.  How do I know this will work? Because my gut’s telling me that the timing is right to build the next version, achieve product/market fit, and scale up.

4.  The power of time off.  Stefan Sagmeister recently spoke at TED about the power of time off.  ”Every seven years, designer Stefan Sagmeister closes his New York studio for a yearlong sabbatical to rejuvenate and refresh their creative outlook.”

After producing and curating The Feast in October, I took the next month off to really think about my 5-year plan.  Let me rephrase.  I took the next month off to commit to something for the next 5 years of my life.  Making this type of commitment takes a lot of self-reflection and soul-searching which can only happen when you take a 50,000 feet view as a lens for the future.  It won’t happen if you have a lot of the same day-to-day distractions i.e. running your business.

I spent some time in Maine and New Orleans thinking about all the opportunities that I could take in my life.  I talked to all my mentors, advisers, and friends (who were very supportive so thank you).  And I emerged with a clear understanding and direction for 2010 and beyond.  Taking time off is essential in making the right decisions, which leads to my next lesson.

5.  Always make the best decisions.  Lastly, a real quick story to wrap things up.  Earlier in the year, I had breakfast with Annie Duke (professional poker player) who told me a great life lesson and story around sunk costs.  In the most basic terms, the concept is used in making good decisions (which is the secret to the success of professional poker players).  Wikipedia defines sunk costs as “costs that cannot be recovered once they have been incurred.”

So, for example, if you’re waiting in line at the grocery store, and the line next to you moves faster, most people won’t hop over to the faster line because of the time they “invested” in their current line.  This makes absolutely no sense as anything invested in your past shouldn’t influence your future.  Another example revolves around relationships.  Most people stay together because they’ve “been together for the past five years.”  Again, people shouldn’t make decisions based on past investments.  And if you’re wondering how this applies back to poker.  Once you make a bet and put your chips in the middle, that money is no longer yours (so you shouldn’t make bad decisions on getting it back).

Instead, you should look toward the future and look at all the different paths, opportunities, and possibilities presented to you right now.  The sky is the limit.  Everything in your past gets you to this point but it’s up to you to make the best possible decision on which path you want to go down. Because at the end of the day, if you make the right decision for yourself, there’s no way that it’s a bad one.

As we move into 2010, I hope many of you swing for the fences because entrepreneurs can and will change the world.  There’s nothing wrong with making mistakes.  It’s a rite of passage to becoming successful.  And to close, remember, “there are no ceilings.  Only the sky.  The sky is the limit.” – Lil Wayne (via Notorious B.I.G.)

“You can tell by my attitude that I’m most definitely from New York
Concrete jungle where dreams are made of
There’s nothing you can’t do
Now you’re in New York
These streets will make you feel brand new
Big lights will inspire you
Let’s hear it for New York, New York, New York!”

Just in case you didn’t get the memo; the New York startup scene is taking off. Both Fred Wilson and Chris Dixon wrote on the New York Startup scene, and I thought I would add in my thoughts from what I’ve observed over the past couple of years.

“Greenwich Village 60s … Venice Beach 70s … London 80s … Silicon Valley 90s … Blogosphere 00s … NYC now…” — @RafeFurst

What sets New York apart from the rest of the world?  New York attracts the most creative, ambitious, and hard-working people into one extremely diverse city.  There’s an energy here that can’t be replicated anywhere else in the world.  Mix that with a great nightlife, culture, and a city that never sleeps — you can see why the New York startup movement has been picking up momentum.  I believe that NYC tech startups have a better eye for design, user experience, business models, and creating companies that solve real problems (and not launching more “me-too” companies).  And the icing on the cake?  The companies coming out of NYC right now are just… sexy.  There’s no other way to explain it.

Need proof?  Here’s a list of all the awesome things happening in the Big Apple.  (You should press play on the Jay-Z “Empire State of Mind” video for the full experience).

UPDATE (December 22, 2009): Just to clarify, I did not write this article as a “NYC versus the world” thought-piece. I wrote this piece to give a 50,000 feet view of what’s happening in New York City.  There are many other cities with a thriving startup culture such as Boston, Silicon Valley, Seattle, New Orleans, Boulder, Los Angeles, etc. Each city is unique in its own way, and each city will continue to pick up momentum and be successful. For example, Post-Katrina New Orleans is starting to become the hub for social entrepreneurs. That’s very powerful. They’ll uniquely define themselves for the history books. If we take what works in each city, this is something that can be replicated in every community around the world. Entrepreneurship is vital for innovation, and can work everywhere from New York to Africa. (Endeavor.org is a great example of a non-profit organization building entrepreneurial hubs around the world to lift communities out of poverty).

COMPANIES
I put together a short list of some of the more prominent startups and established companies in New York. There are hundreds and thousands of other companies that can make up this list, so please add missed companies to the comments section below.  Apologies if your company, organization, or initiative was left off this list.

One thing I’ve noticed over the past year is that NYC’s version of Silicon Valley will be Soho, which has been primarily associated with the fashion industry.  The combination of the falling price of leases stemming from the 2008 financial collapse, and the dropping rent (all the bankers moved out of Manhattan); there have been dozens of creative startups opening up office in Soho.  I’ve listed the ones I know in the list below.

1. 20×200 sells art for everyone at ridiculously affordable prices (Soho).
2. Aviary makes creation accessible to artists of all genres.
3. Behance organizes the creative world to make their ideas happen (Soho).
4. Betaworks is an internet media company.
5. Blip.tv is the next generation television network (Soho).
6. By/Association is a private service for new introductions to remarkable people (Soho).
7. Bug Labs is a modular, open source system for building devices.
8. Boxee is the best way to enjoy entertainment from the Internet and computer on your TV.
9. Carbonmade helps you build and manage an online portfolio website (Soho).
10. ChallengePost is a marketplace for challenges.
11. Clickable is an online solution that makes creating and managing online advertising simple and effective.
12. College Humor is the best humor site on the internet.
13. Designer Pages is a free social application for finding products in architecture and interior design.
14. Drop.io allows simple real-time sharing, collaboration, and presentation.
15. Etsy is the world’s most vibrant handmade marketplace.
16. Foursquare gives you and your friends new ways of exploring the city (Soho).
17. gdgt is the new consumer electronics site by the guys behind Engadget and Gizmodo.
18. Harvest allows simple online time tracking, timesheet, and reporting (Soho).
19. Hello Health helps doctors communicate, document, and transact with their patients in person and online.
20. Hot Potato allows you to find events, join the crowd, and share the experience.
21. Hunch helps you make decisions and gets smarter the more you use it.
22. Kickstarter is a funding platform for artists, designers, filmmakers, musicians, journalists, investors, and explorers.
23. Knewton allows students to prep for GMAT & LSAT with online courses guaranteed to raise scores.
24. Livestream is the most powerful live broadcast platform on the internet.
25. Meetup helps groups of people with shared interests plan meetings and form offline clubs in local communities around the world.
26. OMGPOP is the #1 place to play free multiplayer games with your friends.
27. Parachutes aims to reinvent how people teach and learn.
28. Quirky is a social product development company.
29. SeamlessWeb is the fastest, easiest, and smartest way to order food delivery online. 
    
30. SecondMarket brings together buyers and sellers in an independent marketplace and auction platform for illiquid assets.
31. Squarespace is a fully hosted, completely managed environment for creating and maintaining a website, blog or portfolio (Soho).
32. Stocktwits is a realtime stock tips community.
33. Tumblr is the easiest way to blog.
34. Vimeo is a respectful community of creative people who are passionate about sharing the videos they make.

PUBLISHING/EMAIL COMPANIES
New York City has always been the epicenter of the publishing and advertising industries.  And that hasn’t changed with this list of innovative companies changing the publishing and email businesses.

1. Daily Candy is a handpicked selection of all that’s fun, fashionable, food related, and culturally stimulating in the city you’re fixated on.
2. Flavorpill is a daily guide to quality cultural events in New York City, Los Angeles, San Francisco, Chicago, Miami and London.
3. Gawker is an online media company (Soho).
4. Gilt Groupe offers luxury designers and fashion brands at prices up to 70% off retail. 
   
5. Huffington Post offers syndicated columnists, blogs and new stories with moderated comments.
6. One King’s Lane offers exclusive sales on designer home accessories.
7. Tasting Table is a free daily email about the best of eating and drinking culture.
8. TBD is a free email newsletter that delivers one world-changing idea and one collective action to improve our future.
9. Thrillist’s daily emails sift through the crap to find the newest and best the Nation is hiding (Soho).
10. Urbandaddy brings you the single thing you need to know every day about your city.
11. Very Short List is a collection of distinct, free, daily e-mails that each recommend one must-see gem a day.

VENTURE CAPITAL
Every city needs a strong VC and angel community to support everything from seed to established companies.  New York City has a strong list of investors supporting the entrepreneurs.

1. First Round Capital is a venture capital firm dedicated to helping talented entrepreneurs build remarkable companies.
2. Founder Collective is a seed-stage venture capital fund, built by a collection of successful entrepreneurs.
3. Polaris Venture Partners invests in seed and early stage companies and in growth equity companies with substantial operating income.
4. Spark Capital is a venture fund focused on the conflux of the media, technology, and entertainment industries.
5. RRE Ventures focuses on expansion stage information technology ventures.
6. Union Square Ventures is an early stage venture capital firm.

CO-WORKING SPACES
Every new startup needs a place to work out of when they first get started.  NYC has launched some new co-working spaces in the past year.

1. Dogpatch Labs is an open source startup lab.
2. Green Spaces is work space to launch green entrepreneurs.
3. New Work City is a community coworking space in Manhattan.
4. Rose Tech is an incubator and co-working space in Madison Square Park.
5. Sunshine Studios is where startups grow up.

EVENTS
Free events are essential to networking, culture, and innovation.  Here’s a list of some of the premier events in NYC.

1. Brooklyn Future Meetup is designed as an authentic off the record forum for discussing what the world might look like in 30+ years.
2. Internet Week is a week-long festival of events celebrating New York’s thriving Internet industry and community.
3. New York Entrepreneur Week (NYEW) is the largest entrepreneurial movement through New York State.
4. New York Tech Meetup is an event  where entrepreneurs can demo something cool to New York’s tech community.
5. NextNY is a fun way to connect both socially and professionally with up-and-comers who have a stake in the future of tech and new media in New York City.
6. Social Media Week identifies and advances the use of social media in the corporate, public and non-profit sectors.
7. The Feast is a series of programs addressing social innovation and new ways to make the world a better place. 

INNOVATIVE NON-PROFIT ORGANIZATIONS
What’s a community without charity?  These charities are re-inventing philanthropy.

1. charity: water is a non-profit organization bringing clean and safe drinking water to people in developing nations.
2. Echoing Green provides seed funding and support to social entrepreneurs with bold ideas.
3. Endeavor transforms the economies of emerging markets by identifying and supporting high-impact entrepreneurs.
4. Freelancer’s Union is a national membership organization that’s free to join.
5. Pop!Tech is a network of remarkable people, extraordinary conferences, powerful ideas & innovative projects that are changing the world.
6. StartingBloc educates, empowers, and connects emerging leaders to drive positive social change across sectors.
7. TED is a small nonprofit devoted to Ideas Worth Spreading.

GOVERNMENT
Every city needs the support of the government and politicians.  The City of New York has made numerous commitments to support entrepreneurship.

1. Mayor Bloomberg outlines 11 initiatives to support New York City’s financial services sector and encourage entrepreneurship.
2. NYC Seed funds seed-stage technology entrepreneurs in New York City.
3. New York City Investment Fund identifies and supports New York City’s most promising entrepreneurs in both the for-profit and non-profit sectors.

EDUCATION
New York City has access to some of the top schools in the country for technology, design, and entrepreneurship.

1. NYU ITP is a two-year graduate program who mission is to explore the imaginative use of of communications technologies.
2. NYU Reynolds Program for Social Entrepreneurship is designed to attract, encourage, and train a new generation of leaders in public service.
3. Parsons is the premier design and art school.
4. Pratt Institute offers studies in architecture, art and design, and information science. 
   
5. SVA is a fine art and graphic art school in New York City specializing in art education for aspiring professional artists.

FUTURE OF THE NYC STARTUP MOVEMENT
All of these things are essential to a thriving startup movement.  Established companies, investors, education, talent, events, etc.  But, what are some other things I’d like to see in 2010 and beyond to support the NYC startup movement and take it to the next stage?

1. Government support. The City of New York should set something up similar to the initiatives of the Greater New Orleans, Inc. GNO, Inc has setup a venture capital match program, which provides for a match investment ($1 for every $2 up to $5MM) for qualified venture capital funds.  The also have angel investment tax credits, which redeems 50% of the initial investment to investors in the form of LA income tax credits.  Both of these initiatives can spur the investment community in New York City.  
2. Summer incubators. To support younger and inexperienced entrepreneurs, programs such as Y-Combinator and TechStars should launch in New York.  Venture Capital firms should put up the capital to support these programs. This will attract some of the world’s most talented entrepreneurs to NYC while providing them an education and experience that will be vital to their success.  And hopefully keep them here in New York.
3. Mentorship programs. The gap between new and successful entrepreneurs needs to be closed. Informal and/or formal mentorship programs should start for the up-and-coming entrepreneurs in New York City.  Why not lend your expertise and experience to the next Steve Jobs when you’ve already sold your company for $500M?  Pay-it-forward, please.
4. Access to capital needs to stay open.  Another way to make this happen is through pitch events such as TechCrunch50 but our version in New York City.  Even if none of the companies get funded, it allows entrepreneurs and investors to network, meet, and hopefully close some deals for investment in 2010.  It would be even sweeter if the City of New York provided a tax credit for these investors (refer to #1).
5. More failures and successes. In 2010, New York City needs to see more failures to show the world that we’re willing to swing for the fences.  And we need to see more successes to set the bar higher for all of the startups launching and growing.  Fail harder.

I often get asked, “what’s happening in New York” and now I can finally zip over this link to answer that question.  If you live in another city, take note on what’s happening in NYC right now.  It’s a good case study to adopt and practice in your own community.  And to quote Jay-Z, “You can tell by my attitude that I’m most definitely from…. Let’s hear it for New York!”

Feel free to add suggestions, ideas, and thoughts to continue this discussion in the comments section below.