Link to Inc.


I’m thrilled to have become a contributing writer to, and now have a weekly column called “StartUp Engine.” 

My first article is linked below. 

I will continue to post links to my Inc. articles on this site, starting with last week’s article about AngelList Syndicates:



Projecting Failure = Paying Interest On A Debt Not Owed


I ran the worst 5 mile race of my life and it’s because at the starting line my head got in the way of my feet.

At the start line, my head was saying:

  • Why is the song “Call Me Maybe” on this running mix? That’s terrible.
  • I haven’t run very much this week; that will mean I have a slower time today.
  • I’m not wearing the right socks; my knees will act up.
  • How is Call Me Maybe still playing? What is this song even about? Dammit Carly Rae Somebody!!

My feet weren’t thinking of anything. They were lined up next to 4000 pairs other feet about to run the race. Everyone was looking straight ahead.

My head told me, “you are going to bomb this race.”

I didn’t know it then, but the race was over before it began.

I carried these thoughts with me into Mile 2, and they slowly became excuses as I projected reasons as to justify running too slowly .

At Mile 3, these excuses became resentments, and in my mind the factual foundation as to why my legs were failing me.  I could feel the resentment scraping away at the adrenaline.

Miles 4 and 5 were foregone conclusions; slow and painful, resenting the initial reasons why I projected I would run a poor race. As had been predetermined at the start line, I ran the race with my slowest time to date.

None of the above had anything to do with my athletic conditioning.

I was well-trained and had just run a half-marathon at a much faster pace for a much longer distance. My performance was instead due to the fact that I let excuses creep and crawl into my mind at the start of the race, and instead of blocking them out, I let them take ownership of my legs and mind. It was if from the get-go, my thoughts of why I would fail took up residency in my mind and started the process of interior decorating.

Projecting failure is a pretty good path toward achieving failure, and is the equivalent of paying interest on a debt that isn’t owed.

Positive thinking leads to a better chance at positive results. At the outset of a race, the thinking cannot be focused on excuses for failing, because the remainder of the run (including the business marathons in which many of us find ourselves engaged) will have an additional and unnecessary challenge. It is simply not acceptable to start with potential excuses to fail.

The idea of the fall creates the fall.

On a go-forward, there will be no projections of failure at the outset of anything — these thoughts become toxic and create a higher chance of leading to a bad outcome.

Next time I’m going to race, I’m going to focus on having two lungs, two legs, and a big heart, and will be grateful that I can use them. I’m going to look at the blue sky in front of me and I’m going to run. Sky. Sky. Run. Run.

I run for my life because I live.


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I CAN’T vs. I can’t


The expression “I CAN’T” has become bastardized.

It has become an excuse for “I won’t”, and not an expression of whether one can or cannot actually do something.  It’s become an unnecessary limitation on what we actually can achieve.

FACT: I can’t dunk a basketball, nor can I play for the New York Knicks, much as I would like to.  No matter what.

FACT: I can’t outrun a gazelle.  Ever.

FACT: I can’t run for President of another country where being a born-citizen is a prerequisite for running for office.

These are capital “I CAN’T's.”  They are factual and physical impossibilities created by physical, professional, or life limitations.  Everybody has limitations of this sort.  But what about the lower case “I can’t”?

Recently, I found myself in two situations where my initial response left me thinking of this issue, and looking at the difference between I can’t vs. I won’t.

1) I was asked to captain a team to run a half-marathon, and I wasn’t a runner.  My initial response: “I can’t.”  As soon as that response came out of my mouth I realized it was a bogus excuse and not a fair use of whether I can or cannot do what was asked of me.  I have two legs, two lungs, and a healthy heart big enough to train and run for a necessary philanthropic cause.  So it was a question of whether I wanted to make the time to train, learn, and focus, and I immediately said “yes, I’d do it”, and I did.

2) I started a venture capital and consulting company, and was thinking of hiring a CFO to handle corporate finance issues, being its an area that I hadn’t ever focused my time or education– corporate finance and the acronyms associated with it scared me, and I felt like it was something I simply couldn’t do.  But then I asked myself: why? Why can’t I do this?  Rather than let the “I can’t” in me scare me away and cost me an additional salary, I did a post baccalaureate in corporate finance at Columbia, dove into the material, and nailed the class.  I didn’t run away, I ran toward what I initially thought I couldn’t do.  And I did it.

My point: note the difference between the lower case “I CAN’T” and “I can’t.”  The former is not disputable.  The latter deserves a bit more drilling down, because often our gut  response suggests that we can’t do something that we actually can, simply because it’s something we either haven’t done and/or are scared of doing.

It’s in these cases that I challenge myself to ask myself WHY can’t I do something.

If the answer is that I’m using the lower case “can’t”, then it’s time for me to ask the second set of questions of whether (a) it’s something I want to do, (b) something I can physically or mentally do or prepare to do; and (c) is it something I want to make time for.  If the answers to the above all come up as yes, yes and yes, it’s time to bear down and start treating I cannot’s as I can’s.

We do this dance one time and one time only.  I refuse to let unnecessary limitations restrict my ability to spread my wings further than I thought I could, and instead swing for the fences.  I refuse to let fear keep me from learning or experiencing new things.

I refuse to live within the confines of what I know and can do today as the proxy for what I can do in the future.

This is my challenge to myself every day: to say I can instead of I can’t.

Unless of course Springsteen calls me to play lead guitar for a massive stadium show tonight…then I need to rethink all of this…

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Dear Apple, I Love You, But…

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Apple has recently stumbled in three areas that I believe are a cause of its faltering stock price and a frustration by product-users and shareholders alike. Dear Apple — wake up guys! There are easy solutions to your problems!

A few years ago, Apple stock was trading in the $200s. It went on to top $700 within a few years, though it has since pulled back to the low $400s, trending toward its 52 week low.

So why are the shares down 40%+ from it’s high of over $700/share in the second half of 2012? Because they have not come out with any new products. And what can be done to rebound?

First, the iPhone isn’t getting the job done. Second, Apple’s most recent conference was really just a placeholder and demonstrative of a hurdle in product development. Third, Tim Cook has yet to create his own presence as the quarterback of Apple’s team.

I write as a user (and huge advocate) of everything Apple, as a self-proclaimed expert on its products from the consumer side, and as a former shareholder of their company.

1. The Secret Sauce for the Next iPhone

Studies show that approximately 300 million iPhones have been sold. That’s a staggering statistic, and iPhones are one of the biggest pieces of Apple’s space domination. Unfortunately, the iPhone 5 has a fatal flaw, as did its predecessors.

I believe that making one change to the next generation iPhone will generate more sales of the new phone than any other iPhone in history. It will satisfy customers and boost the stock price. And it’s so simple. Here’s the sauce…

We don’t need more bells and whistles in the next generation; we need one thing and one thing only: a functional battery. The current battery is notoriously weak.

The iPhone must be able to compete with its android competition, and there’s no way it can do that without having a battery that can last the average person through a full workday. The current version of the iPhone is the equivalent of giving someone a can of food with no can opener. Despite the argument that it’s a great device, it’s worthless unless the next Apple product is the iStrip… a power chord to walk around with so that the phone can be charged three times a day.

People want to use the iPhone — it just needs to be useable.

2. Great Expectations from WWDC Isn’t Enough

WWDC 2013, which took place last week, is Apple’s annual event during which it announces its newest products and technology. Typically, these products and technology would then be ready for market immediately or shortly thereafter. Not this year.

Last week, Apple announced a iOS 7 (a new operating system), a new Mac Pro, OS-X Mavericks,and iTunes Radio. None of these will be available until the Fall (at the earliest). Interestingly, Apple typically has another conference during Q4 where new products are announced as well.

As a consumer, this makes me believe that these recent announcements were premature, and an attempt by Apple to use this conference as a placeholder. These announcements could have and should have been made when the products and technology were closer to roll-out.

Notably, there was no Steve Jobs’ “wait, there’s one more thing” — there was no “wow factor.” Aside from a stronger battery life on the MacBook Air, Apple did not announce any new product or technology that is available in the near future. What this means is that they are stagnating on the new product roll out while other companies are developing new Android-based wearable computers like Google Glass.

So what’s happening in Palo Alto? Unfortunately, the conference makes me believe that Tim Cook and his team have hit a wall (or hurdle?) given what appears to be a lull in product innovation since Steve Jobs’ death in late 2011.

3. Tim Cook Must Establish His Own Persona

Steve Jobs was one of the greatest innovators and showmen of our time. He revolutionized music, computers, telephones, tablets, software, and arguably, television. It’s impossible for Cook, or anyone for that matter, to step into a pair of those New Balance sneakers (or black turtleneck and jeans.)

That said, Cook hasn’t established his own personality as a tour de force that Apple needs at its helm. Cook hasn’t sufficiently acknowledged the elephant in the room to say, “Hey, I’m not Steve, there will not be another Steve. But I’m Tim, and here’s what I can do to keep Apple on the growth track that Steve built.”

Until Cook openly acknowledges this fundamental fact, consumers and investors will continue to compare every word and every action of Cook’s to Jobs, which is a disservice to Cook’s abilities and the company’s growth.

There’s no doubt that Apple is at the epicenter of the largest technology revolution in our time, and it’s this author’s opinion that the stock price doesn’t reflect the ability of Apple to maintain its domination in all of the pools in which it swims.

However, to get back there,they need a fundamental fix to their iPhone, to focus more heavily on delivering product quicker to consumers, and Cook needs to grow into a personality that will invoke the confidence of investors.

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How 10 Mentors Got Me Through 13.1 Miles


Up until 3 months ago, I hadn’t run a mile since middle school. And when I did it back then, I threw up.

I ran my first half-marathon last weekend, to honor the memory of a friend and for an incredible organization, Active Minds. 13.1 miles, and I did it in a respectable time.

In running, I’ve found that a spectator or fellow runner throwing me a high-five gives me a boost of energy to push it and dig deep. It’s not uncommon for runners’ bodies to be hurting, and a high-five gets them over a hump, taking the heavy lifting off the legs and letting the mind find a path toward the next stretch of miles.

In business, it’s the same thing. It’s always a source of inspiration to get a metaphoric high-five from the influential and experienced minds that have built the bridges that many of us are crossing. The goal is always to surround yourself with winners in this respect.

When I signed up to run, I was nervous, scared, and questioning whether I would finish. After some thought, in addition to training, I figured out a way to overcome any doubt and run with confidence.

My model to get through the half-marathon was straightforward: break the run into “chunks” of a playlist of songs which are linked directly to the lessons learned from the friends and mentors I’ve developed through social media and business.

Each song gave me a new subject for reflection and thought, and it took me back to the various dialogues and lessons learned from these incredible people. With this strategy, the run was over before I knew it.

In addition to running with the memory of my friend at my back, and the support of my family in the crowd and in my heart, here are 10 mentors and friends — each one a different part of my race — and the songs that I associated with each, in no particular order.

1. Michael Lazerow: Ride by Cary Brothers

Laz, a serial entrepreneur, called me a “wild man” when I told him the following: the ultimate catalyst for my decision to create Excel Capital Partners was watching Mike’s video, fifty times on repeat, the day that he sold Buddy Media to Sales Force. This is the song from the video. It’s Laz’s mantra of living fearlessly that I carry with me every day, which is why the song made multiple appearances on the running mix.

2. James Althucher: The Wall by Pink Floyd

James, an author and entrepreneur, teaches me to write for nobody but myself, and to open up and be raw and honest. His encouragement to push the envelope and get to the core of my emotion with my words has been invaluable, and this song is a hat tip to James’ philosophy about formal education’s stifling of creative thought — “hey teacher, leave those kids alone!”

3. Brad Feld: Better Man by Pearl Jam

Foundry Group Managing Director Brad Feld’s generous back-and-forth about Digital Sabbath and encouragement to run has made me a better person. In practicing Digital Sabbath, the concept of unplugging on weekends to recharge the batteries, has altered my life significantly the better, period.

4. Gary Vaynerchuk: Gonna Fly Now (Theme from Rocky)

Meeting with Vayner Media founder Gary V. makes you feel like you can do anything, let alone run a half-marathon (or, in his case, buy a professional sports team.) Gary’s lessons of the import of context over content, and his story of building his business and building his brand is an amazing one. Connect with your audience! Provide context! This song fires me up to crush it every time.

5. Chris Paik: Patience by Guns n’ Roses

Patience is a virtue, a lesson I’ve come to further appreciate from Thrive’s Chris Paik. Chris has been nothing short of generous with his time and advice, and he’s always made it a point to focus on the import of patience and diligence before making decisions.

6. Derek Flanzraich: Born to Run by Bruce Springsteen and the E Street Band

My favorite song, my favorite band, my favorite entrepreneur. Derek’s company Greatist got me motivated to focus on health and wellness, and Derek is my daily dose of inspiration. Born to Run is the crescendo of the mix — it’s a nod to knowing that I don’t have to be “the” greatest, but that every day I must be “A Greatist” and be the best version of me each day.

7. Ben Lerer: Wild Nights by John Mellencamp

Thrillist Founder Ben Lerer was able to convert wild nights into an incredible media empire, and his focus on “being real” is the reason he’s such a success. Ben, like Gary, has the ability to pull life from the walls, and his enthusiasm for media and VC is contagious; it also doesn’t hurt that he’s wicked smart and an all around excellent guy.

8. Scott Belksy: Beautiful Day by U2

Behance founder Scott Belsky’s writing is nothing short of brilliant, easy to digest, and always on point. Scott’s work is a must-read, and his words of encouragement to me during his exceptionally busy time with the Adobe sale is the classic example of a business-high five.

9. Dhani Jones: Hearts on Fire by John Cafferty

It’s not often one gets athletic and life advice from a guy that started in the Super Bowl, and my friend Dhani’s constant encouragement to row (and row….and row….) was nothing short of hard-core and awesome. More importantly, my respect for Dhani runs exceptionally deep, particularly because of his thoughtful and kind nature, and his and focus on giving back through BowTie Cause.

10. Sarah Stanley: Edge of Glory by Lady Gaga

Ultra-marathoner Sarah Stanley became a friend, coach, and mentor through meeting on Twitter. Sarah was super inspirational in checking-in and coaching me through my first race. In talking to Sarah, I always felt pumped up, like I was ready to tackle the race and I was standing on the edge of glory, waiting for the starting gun to fire.

While the race course didn’t have too many spectators, my playlist was the mental equivalent of running up First Avenue in the NYC Marathon, as I had the benefit of reflecting on incredible lessons from my friends, and knowing that each was giving me a high five as I ran. And it was awesome.

With that said…today I signed up to run the New York City Marathon in November.

What would your playlist look like?

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Thank You, 102 Years Later…


I had a holy shit moment this morning; I learned that one particular day, over one hundred years ago, completely altered the trajectory of my life. Literally, a single moment in time.

In March, 1911, a woman named Lena didn’t go to work because she had a stomach ache, which later was determined to be labor pain.

Until this morning, I didn’t know who Lena was, where she worked in 1911, nor did I know the relevance of her decision not to go to work.

March 25, 1911 was the famous Triangle Shirtwaist Factory Fire in New York City. The factory was a garment factory near Washington Square Park, and the workers there produced women’s blouses.

The fire was one of the deadliest industrial disasters in the United States, resulting in the fourth highest loss of life from an industrial accident in U.S. history. Most of the victims in the garment factory were recent Jewish and Italian immigrant women aged sixteen to twenty-three, and 149 of them were killed.

Lena worked at the garment factory.

March 25, 1911…the day that Lena didn’t go to work.

The factory managers were animals; every day they locked the doors to the stairwells and exits to prevent theft of the blouses by the workers— this meant that the workers were stuck inside during the fire. They were helpless.

The managers were more concerned with the five cent goods than the lives of the workers. No compassion was shown for the safety of the lives of women and children who were working approximately ten-hour days for $7 to $12 per week to help support their families. The lives of women who had little choice but to accept the job, despite the life-risk that it entailed.

Then one day the building went up in flames. The cause? A match or cigarette left in a trash bin.

The fire was the catalyst for agencies like OSHA, as it prompted legislation to improve safety standards and spurred growth for the garment unions, which fought for better working conditions for sweatshop workers.

We hear stories of the man who missed a flight on a plane that crashed, or the woman who was late to work on 9/11. Stories of people whose lives were saved by divine intervention or simple happenstance, depending on your view of the world.

These life changing stories make me contemplate whether there is a bigger plan for us. I love the expression that “we make plans and God laughs.” It’s true. Life happens and we respond. We react.

This morning I learned about Lena.

Lena was my wife’s great grandmother.

This isn’t a sermon. This is my step back from getting caught up in the evolution of historical analysis, whereby everything today somehow becomes “Instant History.” While social media is an incredible tool for news, history itself is like a tree with roots and develops through time. We’re just not as patient as we used to be.

I always say that my wife makes me believe that angels exist. Had Lena gone to work that day one hundred and two years ago, my wife’s family wouldn’t exist, and I wouldn’t have the greatest gifts in the world: my wife and son.

For me, that’s divine intervention. And it’s divine.

Thank you Lena. Thank you for following your instinct that day in 1911.

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Chess Hustling, Writing, and Developing the Pieces


Yesterday I needed a mental colonic.

I was frustrated, uncomfortable, irritable, and annoyed. I had applied to be a contributing columnist/blogger for a renowned magazine, and was told that my writing wasn’t “what [we] are looking for at this time.”

In times of frustration, I try to change my thought with an action. So during lunch, I found myself in a cab headed to Washington Square Park.  Destination: the chess hustlers.

Ten years ago, while in law school, I spent as much time in that special corner of the Park with the hustlers as I did in class. I loved the speed of the clock and the clicking of the pieces against the table. I loved the game and the strategy. I loved how chess was (and is) such a great metaphor for life.

I hadn’t played in almost eight years. I don’t know why, other than life got in the way.

I played yesterday with a man named Omar. He spends his days in the Park playing chess. He makes his living on people like me. More pointedly, he makes his living betting a few dollars a game against tourists who try to take their shot and live out a Bobby Fischer moment. I split a sandwich with Omar and told me to give me his best.

I wonder why Omar had a cast on one arm. I wonder where Omar lives. I hope not on the street. He probably does. He was a nice guy and a hell of a chess player, and that makes me sad that he likely is sleeping under a tree right now.

The rust of my not playing for years came off quicker than I thought. The clicking of the pieces against the marble and cement table was like a symphony. The swapping of knights, bishops, and rooks created an adrenaline rush.

We played four games in twenty minutes. I lost all four. I didn’t care. With each game, my mind became more focused, and the thoughts of the rejection by the magazine disappeared. Each game made me smile more. I felt alive.

Throughout each game, Omar told me to develop my pieces. He was telling me not to attack too early with one or two pieces, without having the artillery of pieces behind my attacker. Otherwise, my lone attackers would be left out to dry. This is basic stuff; the muscle memory of my brain needed to be readjusted to get back into the cadence of the game.

Omar told me that the clock is within my control and to be patient in setting up my team of players. Develop my pieces. Get all of my guys out of their starting boxes and position a team ready to unload with force. Otherwise I’d be on the run the whole game.

Without knowing it, Omar was teaching me about my writing.

I left the Park knowing what I needed to do.

I’ve been blogging for a fairly short time. I’ve written some good pieces, some okay pieces, and some that probably deserved to be left unpublished because they were more about me than about anything relevant to readers other than my grandmother.

Before submitting an application to write for a major magazine, I need first to develop my pieces. To tighten up my message and my voice. To write by developing my pieces carefully, making the writing less about one piece and more about the game. I recognize the irony that this piece is about me. Funny how that works.

I don’t believe in coincidences. I believe in fate. This morning I was reading James Altucher’s new book, Choose Yourself. Maybe the book subconsciously led me to the Park today. Certainly, however, the book has taught me that rejection is temporary and giving up is forever.

I’m not giving up. I’m going to instead work to develop my pieces. Slowly and methodically. My writing and my voice needs to be a fully developed chess opening, not a surgical strike of one or two pieces trying to take over a board.

I’m not giving up. Instead, I’m going to play more chess with Omar.

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911 Operator, How May I Help You?


I thought a woman was dying tonight on the corner of 84th and 3rd.

As I was crossing the street on my walk home, I heard the loudest blood-curdling screams I’ve ever heard.  The source of the demonic screams were from a woman in her mid-forties, hunched over on a car.  She was dressed casually, as if she were coming from a spin class.  I couldn’t see her face.  I just heard the screams.

The screaming escalated, as if she were trying to scream the devil out of her stomach.  I’ve never heard screams of that magnitude or of that pain.

And people walked right by her.  At least a dozen of them.

I called 911.  The screaming must have gone on for almost a minute. A minute of the loudest most brutal scream you could imagine, though it was beyond imagination.  I thought she might die on the street.

As I was on the phone with the 911 operator, I approached the woman, thinking maybe she needed the Heimlich or that I could offer some sort of assistance, and I asked her to try to tell me what was wrong.

She raised her body and face and looked at me.  The screaming stopped immediately.

I looked at her face — her dark, angry eyes, her soot covered sunken-in cheeks, and the weathered skin of someone who has lived way too many years on the streets of New York City.

She then quietly picked up a garbage bag of cans and walked away, as if nothing had happened.

This was her life.  This sad, scary, moment was assuredly one of many that make up a day in the life of this woman.

I walked away wondering what could lead to such pain.  Such agony.  And such screams.

My pace picked up; I walked straight to my apartment, kissed my wife, and then went directly into my son’s room.  My son turned eight months old today.  Though he was sleeping, I gave him a kiss and held my hand on his back for the longest time.

Tonight I have no luxury problems and no luxury complaints.

Tonight, I have only gratitude for my gift of today.


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My Brologue: My Best Shot at Winning the Lottery


The Powerball was over 400 million dollars. And I may have won.

An interesting part of blogs is that they develop followers over time, which sometimes feels like picking up a TV show mid-season, where followers don’t get the full flavor of how and why the blog was born. So I consider this piece my “brologue” (I think I just invented the term for a blog prologue.)

Every single one of us has had the inevitable “lottery conversation.” Late last year, I found myself engaged in that very conversation when the Powerball had reached a record high, and my wife and I were holding our tickets like unopened Wonka Bars.

As we sat around the table at a charity event, everyone believing that they could win 400 million dollars, the table conversation became focused on the “what would you do if you won?” Predictably, and sadly, many people said they would quit their job the following day, spend money on x, y, or z extravagances, and have that be that.

When the table turned to me, my answer was simple. I said, “I’d write.”

My answer just came out. It wasn’t planned. It was pulled like a magnet from deep inside my brain and came out of my mouth within a nanosecond. It was a moment of unfiltered brutal honesty.

Winning the lottery might give us a sense of monetary security, but I asked myself – money aside, what would I actually do with my day? Where do my truest passions lie?

For me, it was obvious that I didn’t need to win the lottery to do this one particular thing; to write.

But the question people ask me is “why” – why am I writing?

First, it’s cathartic, and it’s something I love to do.

More importantly, I write because it gives me the opportunity to open myself up on paper and to hopefully leave a legacy and make an impact. That, my friends, is what gets my hair on fire. Legacy and impact.

In the case of my writing, legacy is more important than currency, and writing this blog is a chance to push myself to be real, to be raw, and to share my own experiences in business and life in a way that hopefully connects to readers.

Admittedly, there is also a small piece of ego involved. I get a sense of satisfaction when I get a note from a reader telling me that my writing has touched them, impacted them, or motivated them. It lets me know that I am making a difference. Equally, I also enjoy getting notes challenging a position I’ve taken or engaging in some sort of debate on a concept stemming from a piece of writing. It means people are reading and thinking about it.

Winning the lottery raises the question of whether you would do something different or in addition to your life than you’re already doing.  I believe it is critical to synergize your passion with your daily life to every extent possible. Success is relative; happy people are inevitably better positioned to succeed when doing something they are passionate about.

Hence, this blog was born.

Do I have the money in my pocket from winning the Powerball? No.

Do I have the result of living one of my passions through writing? Yes.

Only time will tell which side of that coin is the true winner.


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