How to Fail

There’s a lot written these days about failing forward and failing fast. That’s nice if you’re Facebook, you’re growing faster than you can keep up and your failures are forgotten faster than they’re created. But failure for small entrepreneurs tends to be painful. Most entrepreneurs want not to fail.

Failure is what most people fear most about jumping into entrepreneurship. Embracing entrepreneurship is in a way embracing failure. They’re tied at the hip. The perception is likely that the most successful entrepreneurs are the ones who’ve failed the fewest times or not really failed at all. It’s the opposite. The most successful entrepreneurs have failed more times than they care to count or mention.

Think of Facebook’s big and yet now forgotten failures. There was Wirehog, an early peer-to-peer, file-sharing prototype that Mark Zuckerberg developed and took seriously enough to talk to investors about. This may not seem like much of a failure, but consider the fact that developing Wirehog likely took thousands of precious hours of Mark and his team’s time, time he could have spend on Facebook, a company now worth $247B!

Other notable failures of Facebook’s include Beacon, a service so disastrous, Facebook had to pull the plug after a few weeks. Developing Beacon likely took thousands of hours of engineer’s time. There was Facebook’s Poke, their Snapchat competitor; the Facebook phone; and Facebook classifieds. They all sound ridiculous now.

Facebook succeeds because they fail. With each of these failures, Facebook was pushing the envelope and evolving their platform into new spaces. The companies that aren’t evolving are the ones that are truly failing.

When I first decided I wanted to start a company more than 10 years ago, I came up with a concept, worked with designers and spent hours and hours ideating on it. I’d talk about the idea with friends who were all excited about it. It came down to committing the capital to proceed with the first order. I had the money for the first order, but struggled to pull the trigger. The (pseudo) company died a quiet death. I just stopped talking about it. Months later, I’d run into friends who excitedly would ask how the product was doing. I’d regrettably tell them I never ended up ordering the product. I didn’t learn much through the process, except on how to ideate.

Entrepreneurship isn’t about ideating, it’s about taking risk, taking action and moving projects forward. I was a classic wantrepreneur. I hadn’t even failed correctly. You don’t learn by ideating, you learn by testing and shipping a product. Get it out there.

There are some important things to understand about failure.

Failure is the process. Look to the most successful companies and see how they manage their failures. If Facebook didn’t allow itself to fail, it wouldn’t be allowing itself to innovate and lead. If you’re trying to avoid failure at all costs then you aren’t doing the right things to best enable success.

Learn, reframe, rebound and pivot from your failures.  Don’t bury your failure immediately. The only true failures are the ones you don’t learn from. Analyze the failure. Look at your assumptions, at your model, at your product, at every step to see what you could have done differently or better. In every case, you can’t know everything and most of the time the only way to know if there’s demand for a product, service, idea is to create and ship it.

Own your failure. With a failure, the tendency will be to hide it. Or even worse, by not giving it enough commitment capital to succeed in the first place. We live in an amazing country at an amazing time. Entrepreneurs are held in high esteem. Fail publicly, fail loudly, and tout your failure. Brag about it, wear it as a badge. That will cure the shame. You’ve got the balls that millions of people don’t. Everyone has an idea for a product or business, only a handful but that idea into motion and commit to it. Wear that badge proudly. Make it the best damn failure anyone’s seen.

The 5 Must Read Books for an Aspiring Entrepreneur

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In Mark Cuban’s autobiography, he talked about getting started out and reading voraciously anything and everything related to his field, business, marketing, etc. He used to read software manuals cover to cover. Drew Houston of Dropbox used to spend every weekend, reading all day long “Every weekend, I would take this folding chair up to the roof with all these books I got on Amazon. I would just sit there and read all of them. I would spend the whole weekend just reading, reading, reading.” 

Nothing prepares you for entrepreneurship like reading everything you can get your hands on. Here are some good places to start.

Richard Branson: Like a Virgin

Richard Branson’s autobiography is a fascinating look at one of the most dynamic entrepreneurs of our time.

Peter Thiel: Zero to One

When you’re just getting started, it’s important to be and stay inspired. Few books will make you want to change the world and business like Peter Thiel’s Zero to One. Peter Thiel was one of the founders of PayPal and the first investor in Facebook. He’s knows a thing or two about business and ideas that change the world.

James Altrucher: Choose Yourself

James Altrucher has seen it all. He’ll recount often how he lost millions and his shirt on several occasions. And through it, he’s gain remarkable insight. Choose Yourself will change the way you think of business and yourself. Somehow it’s only $0.99 on Amazon. It’s a quick read, get it.

Mark Cuban: How to Win at the Sport of Business

Mark Cuban is loud, brash and unapologetic. He didn’t get lucky becoming a billionaire. was his third successful business. That’s a habit. His autobiography breaks it down and shows his remarkable prescient about the growth of technology and exactly how hard he was willing to work to win.

Steve Chandler: Wealth Warrior

Wealth Warrior incorporates a huge amount on wisdom about business and personal development in very few pages. A brilliant read. Steve Chandler’s focus on oneself and your motives, refocuses the whole narrative on entrepreneurship.

What are your must read books for a new or aspiring entrepreneur?

The Number 1 Rule for Entrepreneurship

A few years ago, I interviewed at Google. The interview process was lengthy and had a very corporate feel. I interviewed with everyone on the team, typical corporate stuff. Then the divisions heads came in and asked the hard questions.

A fews year prior, I had tried my stint at Wantrepreneurship. A friend and I had written a business plan, drafted a product document, and started pitching a business. There’s a huge difference from pitching a business and running a business. I think one of us even called ourselves CEO. At the Google interview, someone asked me what my greatest lesson from running a business was. I stumbled a bit and gave a half hearted answer because I didn’t have a good answer. I hadn’t run a real business.

What I know now from running my own business for three years is: the most important lesson is to get up every day, push aside all the distractions, and move the goddamn business forward, every single day. Do something, make a call, send an email, make a connection, send a pitch, follow up with prospects that guarantees you’ll be in business in a day, a month, a year. How do you know what to do? Tim Ferriss’ approach is to do the three things you most don’t want to do, first thing in the AM before doing anything else. Those tend to be some of the most important tasks. Everything else is secondary. Do it whichever way you can. It doesn’t have to be pretty, it doesn’t have to happen at 9 AM, you don’t have to play any politics and the best part is you don’t have to ask anyone’s permission. Just get it done.

You’ll find someone to take care of the accounting, the website is good enough for now, you can blog when you’ve closed more deals this month, put aside the potential pretty sounding business partnership, stop tweaking the business model and pitch deck and get some customers! You want to impress investors, get someone to pay for what services or platform you provide. Lose track of this rule, and you will get swamped in the incidentals that you might confuse as essentials. Do it enough days in a row, and you’ll be risking the business.

As Mark Cuban says, “Sales solves all problems.” Get out and sell like your life (or business) depends on it. It does. If you take that attitude, you’ll find a way to drive in revenue. If you’re not careful, busy work and distractions  will suck up your life and destroy your business. If you don’t run a business, taking this approach will help drive your career forward as well.

Agree with Everyone

In college, in my circle of friends, there was a guy I referred to as “yeah, but” man. You would start to say something, no matter what, and would he would immediately jump in and say “yeah, but…” somehow disagreeing with your statement, opinion, thought, etc. And it could be about anything. And it was one of the most infuriating habits I’ve encountered. He had trouble making and keeping friends, and he never knew why.

A few years ago, a friend and I were having a discussion and he mentioned how the Mormon Church used to not allow caffeine and then in the 80’s, they invested in Coca-Cola and shortly thereafter changed their policy on caffeine. I called bullshit and told him it was an urban legend. (Recently, the Mormon Church clarified their stance on caffeine and sodas, and it seems that the ban only refers to “hot drinks.”

My buddy didn’t take it well. He argued fiercely about it. This was pre-smart phones, so we couldn’t just Google it. The next day we met up to go surfing. He got in the car and launched into a treatise about how he researched it online after we talked and it wasn’t entirely clear… I was surprised he had given it a second thought, but now he was getting worked up about it and I could sense some tension. All because I had disagreed with him.

We have a strong desire to be right. We correct people, we argue with people, and fight for our opinion. But at the core of it, is this desire to be correct, to be validated, to give our ego a little pat. Who gives a rat’s ass about being right? Unless, someone’s raving about Hilter being misrepresented in history or some other offensive thought, just leave it alone. Better yet, agree with them. If you try to correct or argue with them, at a minimum you’ll go on talking about longer than the subject matters or care to. Agree, nod, and move on.

In James Altrucher’s book, Choose Yourself (a phenomenal and highly recommended read), he talks about giving up opinions. Take an opinion he has. They don’t matter, he’s not going to convince you otherwise of your opinion. People change their opinions all the time, but if you try to fight for yours or argue your side, you’ll just further cement the other person’s opinion about it.

My friend’s probably never thought about the Mormon’s Church stance on caffeine. I certainly haven’t and never cared about it in the first place, but we got into an argument about it. Who really cares?

In improv, there’s the “Yes, and” principal, which is the exact opposite of my friend, “yeah, but” guy. The improv principal is about building on a thought, collaborating, moving forward, and focusing on the now. It’s a core principal of improv. It’s never talked about in business (well, I Google and this author wrote a good post on using improv principals in business) or life. Why not just use that principal in life? Stop disagreeing about anything and everything. Start any sentence out in when talking with someone after they’ve finished with “yes, and…”

Here are some ways to apply it:

  • Agree with everyone. Just start your next sentence with “yes, and…”
  • Stop the story battle. When a you hear a story, a lot of times your tendency is to share a similar (or better) story right after. Just let your friend’s story sit and marinade. Compliment it, or ask them to go deeper. By telling your story right afterwards, you’re wanting to shift the attention back to you and in a way you’re invalidating your friend’s story (i.e. subtly you’re saying yours is better).
  • Just listen. Another core principal of improv. It’s amazing what you’ll actually hear, what you’ll learn and how much better conversation will be when you’re not fighting to talk, to be heard or for attention.
  • Don’t interrupt or finish someone’s thought or sentence. This is a thought hijacking. Usually when you finish someone’s thought, you want them to finish. Let them finish on their own.

The last of these came out of this book, Don’t Sweat the Small Stuff, a remarkable little book with some amazing insights.

When Opportunity Comes Calling

“Fortune favors the prepared mind” – Linus Pauling

I recently wrote an answer to the Quora question: What is the Most Effective Yet Efficient Way to Get Rich. See the original answer here. The response has blown up, and I’ve been flattered by the comments and votes it’s received (over 3K and counting!). My previous most upvoted answer on Quora was the story of how I got Dengue Fever in Thailand under the question: What’s the Stupidest Thing You’ve Done.

It’s inspired me to start writing again for my blog and given me a new sense of direction for the content.

Many people have been struck by the answer in the same way that I was when I first read the anecdote of the Italian billionaire. It can be that simple. I was talking with a friend from France about entrepreneurship here vs France and asked him what the difference was. He said that in France when you bring up the idea that you want to start a company, people tell you it’s a bad idea, that it’s too hard and that it won’t work, but here when you bring up the idea of starting a company, people tell you it’s a great idea, that you should go for it and suggest ways they can help or people you should talk to.

My former boss whom I mentioned in the Quora answer, started his own Biotech company. Know what he did before he raised $10M to start his own Biotech company? He was a pharmaceutical sales rep. Know what he did before that? He was a Baptist Minister. And before that? He was a limo driver.

What’s even better, he met the investor who gave him $10M, waiting in line to buy tickets to a concert.

I remember Bob telling me this story and being blown away. We live in a country with a $14 trillion economy. Trillion. That’s dizzying number. Want a piece of it? It’s out there for you. You don’t have to take it from anyone. It’s sitting out there waiting to be claimed. Your keys to the kingdom are waiting on an answer on Quora or with the guy you wouldn’t think twice of in the line next to you in the ticket line for a concert. There’s opportunity around you, all the time.