‘Fail Your Way to the Top’: Learning the Don’ts of Entrepreneurship

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FailAs a cynic, I gravitate to the negative. Maybe that’s why I so thoroughly enjoyed MJ Gottlieb’s How to Ruin a Business Without Really TryingAs you can probably tell from the cheeky title, this is not your average “entrepreneur’s guidebook to success” — this is a book all about failure, comprising 55 case studies that focus on “the most prevalent and destructive mistakes entrepreneurs make.”

But even for the more optimistically inclined among us, How to Ruin a Business is a necessary read. Samuel Beckett commanded artists to try again, fail again, and fail better; Gottlieb, an experienced entrepreneur and consultant who runs Hustle Branding with Gary O’Neil, applies a similar mindset to the world of business.

“I think that business and life is all about what we do in response to the stumbling we do,” Gottlieb says. “Everything that we do for the first time, normally, we do wrong, and then we adjust and modify and tweak and sail forward. So many people try to be perfectionists at everything they do, and they think a mistake is a big problem, as opposed to looking at it as an opportunity to learn from that mistake and not make that mistake in the future.”

“You’re going to make a gazillion other mistakes in your entrepreneurial journey,” Gottlieb adds. “Be okay with that.”

I spoke to Gottlieb over the phone to learn more about the book, what he hopes readers get from it, and those fantastic illustrations by the 12-year-old (now 13) prodigy, William Roth. What follows is a transcript of that conversation, minimally edited for style and clarity.

Recruiter.com: Let’s say I’m a random person who walked up to you on the street and asked, “What’s your book about?” What do you tell me?

MJ Gottlieb: This book is all about doing your due diligence and learning through the mistakes of others before you make those mistakes yourself in your own entrepreneurial journey.

I think that most people … go into business the first time knowing the same thing as everybody else going into business for the first time: absolutely nothing. By studying the history of companies that have either failed or succeeded and what they did to rectify, fine-tune, and tweak their mistakes, entrepreneurs might be able to avoid these mistakes.

RC:The book is kind of positioned as a list of don’ts. Did you do that because you wanted to help people avoid these mistakes?

MJG: I believe that entrepreneurs are idealistic by nature, and they don’t like to be told what to do. That’s why they forge their own paths. So, how do you teach somebody that doesn’t want to be taught? I think that you need to take the ego out of the equation and say, ‘Hey, listen, here’s how I screwed up.’

There are 55 case studies in the book. Each one has ‘the wrong,’ where I tell them how I screwed up, and ‘the right,’ which is how I would do things differently given what I know now. So you have the identification and the emotional attachment in the wrong, and then you circle back around the case study and see what the correct way to handle it is.

RC: As you mention, there are a lot of case studies in this book. Are there any highlights in particular that you want to point out? Any common themes?

MJG: In the first section, I talk a lot about emotion and never making a decision in a negative emotional state, never making a decision in a positive emotional state, never making a decision with your ego, because there’s a complete difference between emotion and passion.

Now, you have to be passionate in what you do. I don’t believe you start a business to make money, because then you’ll just burn out and give up. So you absolutely need passion for what you do.

But emotions, on the other hand, can completely destroy your business. I don’t know how many times I’ve heard from people saying, ‘MJ, I hit the send button,’ or ‘I was really pissed off and I called the guy and I just cursed him out.’ Well, let’s say that person owned a chain of 700 stores. Now what?

It’s like my father used to say: count to ten, take a pause, and never make a decision when you’re in an emotional state. Most of the time, that decision is not going to be the correct one.

RC: I also wanted to talk a little bit about the illustrations. Is it true they were done by a 12-year-old?

MJG: Well, he’s 13 now, but yeah. William Roth, he’s really great. The illustrations are really great. I think they add a lot of dimension to the book.

If you notice, every illustration has a person screwing up. If you look closely, that person has a name tag that says ‘Hello, my name is MJ.’ A lot of people tend to stand on podiums and take a holier-than-thou mentality when they’re trying to tell people what to do, and I’m really trying to say that I’m an experienced screw-up. That’s what I am.

Basically, by using those illustrations to show the pitfalls and experiences that Gary [O’Neil], my business partner, and I have gone through, it adds a little levity. It lets people identify with the journey, seeing me beaten up and disheveled throughout the process.

By Matthew Kosinski