Tag Archives: Startup Advice

Ten Lessons I Learned from Shark Tank

STCubanI just gave up all parenting responsibilities this weekend to Mark Cuban. Meaning, my kids and I watched eight straight episodes of "Shark Tank". For the past two years, people have been begging me to watch “Shark Tank”. One friend of mine, who has co-invested with me on two deals, has given me two pieces of advice in life. One is: “you never know what someone is worth until they declare bankruptcy”. The point is, we all speculate that someone is worth $100 million or a billion or whatever, and the next day you read in the newspaper that they declare bankruptcy. Now you know. The second thing my friend and co-investor was always telling me was that “James, you need to watch Shark Tank”. Now, after watching every episode, I can say I agree with him.

How To Get People To Do What You Want

shutterstock_95416072Leadership in management is the art and science of getting others to do what they don’t necessarily want – or don't understand why they’re being asked – to do. Doing it at a startup is accomplishing all of that in the face of uncertainty and with little resources. Now imagine doing that without the war chest supplied to you by VCs as you bootstrap. Good times, but also a pain in the ass.

In Startups And Life, You Need Plan A, B, And Z

A, B, and ZAn entrepreneur receives lots of contradictory advice from really smart, experienced people. For example, you’ve probably been told to be both persistent and flexible; to have a clear vision you pursue relentlessly, and yet also to change your vision as the market changes. Simple, right? This same tension pervades career advice. Some will tell you to think about where you want to be in ten years, work backwards, and construct a long-term career plan for realizing your ambitions. Others tell you that firm plans are like a straitjacket; they will blind you to unexpected breakout opportunities. It’s better, they say, to stay nimble and opportunistic.

Patience is a Virtue, for Losers

lazy catPatience is one of the seven virtues, the lesser-known cousins of the seven sins.  And indeed, “patience is a virtue” – or so goes the saying.  But another saying states that “fortune favors the bold.” So which one is it? It’s not that patience isn’t valued; it’s that no one else is actually all that patient.  Whether you are growing a business or chasing a girl or trying to lose weight or auditioning on American Idol, no one will sit around and wait for results. They will be impatient. This doesn’t mean you should be impatient, it just means that in the words of George Jackson: “Patience has its limits.  Take it too far, and it’s cowardice.”

To Pivot or Not to Pivot

mountain bikeAh, the internet – how you hijack our vocabulary.  A few years ago, “embedded” had connotations of journalists following soldiers.  Today, it’s most associated with YouTube clips.  Similarly, a pivot was something that I vaguely recall my basketball coach talking about.  Today, it’s the repositioning of a company and without a doubt, 2011 was the year of the pivot.

Why Every Entrepreneur Should Self-Publish a Book

snoopy_writingI've published eight books in the past seven years, five with traditional publishers (Wiley, Penguin, HarperCollins), one comic book,  and the last two I've self-published. In this post I give the specific details of all of my sales numbers and advances with the traditional publishers. Although the jury is still out on my self-published books, "How to be the Luckiest Man Alive" and "I Was Blind But Now I See"  I can tell you these two have already sold more than my five books with traditional publishers, combined. If you, the entrepreneur, self-publish a book you will stand out, you will make more money, you will kick your competitors right in the XX, and you will look amazingly cool at cocktail parties. I know this because I am seldom cool but at cocktail parties, with my very own comic book, I can basically have sex with anyone in the room. But don't believe me, it costs you nothing and almost no time to try it yourself.

Why Every Entrepreneur Should Self-Publish a Book

snoopy_writingI've published eight books in the past seven years, five with traditional publishers (Wiley, Penguin, HarperCollins), one comic book,  and the last two I've self-published. In this post I give the specific details of all of my sales numbers and advances with the traditional publishers. Although the jury is still out on my self-published books, "How to be the Luckiest Man Alive" and "I Was Blind But Now I See"  I can tell you these two have already sold more than my five books with traditional publishers, combined. If you, the entrepreneur, self-publish a book you will stand out, you will make more money, you will kick your competitors right in the XX, and you will look amazingly cool at cocktail parties. I know this because I am seldom cool but at cocktail parties, with my very own comic book, I can basically have sex with anyone in the room. But don't believe me, it costs you nothing and almost no time to try it yourself.

The Uphill Battle Of Social Event Sharing: A Post-Mortem for Plancast

plancast_penguin_running_200x225Nearly three years ago, I left my position at TechCrunch to start my own Internet business, with the idea of creating a web application that’d help people get together in real-life rather than simply helping them connect online as most social networking applications had done. Alas, our efforts began to stall after several months post-launch, and we were never able to scale beyond a small early adopter community and into critical, mainstream usage. While the initial launch and traction proved extremely exciting, it misled us into believing there was a larger market ready to adopt our product. This post-mortem is an attempt to describe the fundamental flaws in our product model and, in particular, the difficulties presented by events as a content type.

Things Entrepreneurs Should Avoid When Raising Capital

_1101957_money300Alright, in my last post I argued that bootstrapping is just as over-rated as raising venture capital. But for those who decide to pursue fundraising, here are some things entrepreneurs should avoid when raising capital. For all of the talk about how much excess capital there is, it’s actually hard to raise capital because very few projects fit the VC profile—even though many VC-funded projects come across as frivolous, me-too projects.

The Seductive Danger Of Half Measures

Half beardIn the wide world of startups, we mostly like to think of ourselves as go-getters, ass kickers, "in all the way" sorts. We also like to think of ourselves as iterators, tinkerers, rapid iterators who test unceasingly. But the combination of those two traits can lead to one of the most dangerous cycles in startup - half measure syndrome (HMS). Interestingly, HMS starts off as something very intelligent - the team does not want to commit to a single strategy until it can prove that that strategy will create the hockey stick. When controlled and focused, that impulse is an excellent driver of evolution, but when not properly grounded in the reality of where you are, it becomes quite dangerous.