I finished this book in September 2022. I recommend this book 6/10.
Guy Raz hosts a popular podcast with the same title as the book. The book is the To-dos and Not-to dos from interviewing over 400 entrepreneurs as they built their iconic brands.
You can get your copy of the book here.
My notes and thoughts:
For the next three and a half years, Jim spent his life outdoors, rock climbing, kayaking, backpacking, and doing adventurous things that probably scared his parent half to death. But in doing them, he learned that "you don't need that much to live on if you're really enjoying what you're doing." He also learned that nothing is permanent and that you can always go back once a different path has run its course.
"One of the things we taught people to do was rappel off a cliff. It is a very scary thing to do, but you are also held by a belay rope, and that rope would hold a car. So walking off the cliff backward is scary, but it's not dangerous. Walking across a thirty-five-degree-angle snowfield on a beautiful late May afternoon with a bright blue sky, on the other hand, is not scary at all, but very dangerous because the snow is melting; eventually, it is going to find a layer of ice, the water will lubricate that ice, and then you have an avalanche. That is dangerous but not scary.
Reid Hoffman said, "Starting a company is like throwing yourself off the cliff and assembling an airplane on the way down."
Knowing that he could always go back to something he was good at, where he had a lot of experience, didn't make the leap into FUBU any less scary, but it did remove a lot of the danger. It gave him a cushion, a fallback plan. The same was true for Jim Koch. The knowledge that he could go back to Boston Consulting Group or some other management consulting firm whenever he wanted to make the insane decision (at the time) to start a craft brewery seems less crazy. For Sara Blakely, the billionaire founder of Spanx, selling fax machines was her fallback. For Mark Cuban, internet entrepreneur and Daymond John's fellow Shark, it was bartending. The founder of JetBlue Airways, David Neeleman, knew that if his idea for a low-cost airline that flew out of the big market didn't take off, he could always go back to being a travel agent.
There is a famous line from Steve Jobs about this pitfall: "Some people say, 'Give the customers what they want.' But that's not my approach ... People don't know what they want until you show it to them." What a lot of people don't know is that there is an important insight at the end of that quote that, inexplicably, always gets cut off, and that statement from Jobs is particularly relevant here:" That's why I never rely on the market research."
This is why if, like most businesses, you aren't doing something completely novel or you aren't doing it in a totally new way or a new place, you should be thinking long and hard about how else you might enter your market besides knocking on the front door and asking for permission to come in. This is something that female and minority entrepreneurs have long had to contend with, whether it means breaking through glass ceilings or breaking down walls built by prejudice. All of which is to say, figuring out how to sneak in through the side door is not new ground you will have to break. A legion of resourceful geniuses has come before you. And what many of them have discovered is that the side door isn't just less heavily guarded; it's often bigger. Or, as Peter Thiel put it in a 2014 lecture at Standford Center for Professional Development titled "Competition is for losers," "Don't always go through the tiny little door that everyone's trying to rush through. Go around the corner and go through the vast gate that no one's taking."
Depending on your relationships and your resources, you may have greater access to one group than to the other—demonstrators or explainers, showers or tellers—and even then, your access might be limited. But fortunately, it doesn't always take a massive groundswell to get the buzz going. Sometimes it's just a matter of being in the right place or finding that one right person.
If you took that leap off the cliff while attempting to build your own airplane on the way down, you deserve to be known. But as the builder of that plane, it's also your job to be the creator of the buzz from that plane's engines. It's your job to make sure that the sound of your doors opening reaches past your front steps and far enough out into the world for potential customers to hear it. It's your job to get attention for the product or the service you are bringing to market. It's usually not easy, and you are going to need help from all forms of media to make it happen because, like Jen Rubio said, nobody wants to hear you talk about yourself. But it's doable, particularly when you are able to build buzz among many possible customers while at the same time engineering word of mouth among your ideal customers.
Mark Zuckerberg said, "Nothing influences people more than a recommendation from a trusted friend."
Walt Disney said, " Whatever you do, do it well. Do it so well that when people see you do it, they will want to come back and see you do it again, and they will want to bring others and show them how well you do what you do."
Tristan even had the blessing and guidance of Ben Horowitz himself, who'd given him two important pieces of advice during his time at the firm: First, Horowitz told him, "What usually look like good ideas are bad ideas, and what look like bad ideas are good ideas, because the problem with good ideas is that everyone tries to do them, and as a result, there's no value to be created there." Second, he said, "you need to do the thing that you believe you are the best person in the world to do, where you have a unique proposition, given your story, to solve a problem." Accordingly, Horowitz encouraged Tristan to abandon a few of his earliest ideas—one to revolutionize freight, another tackling childhood obesity with play—and instead to pursue this thing he was uniquely experienced to execute.
It was the kind of consistent rejection that could have been completely demoralizing. It could have made Tristan question everything he was doing and doubt all of his instincts. But he didn't, for a few reasons. "I knew there were sixty more investors right behind those sixty," he said, "and if they weren't going to invest in my idea, I knew they weren't going to fund somebody else's version of it either."
One of the principal ways they do this, especially if they are unfamiliar with your industry, is to ask lots and lots of questions:
How do you expect this to scale?
Where is the growth going to come from?
Who is the customer for this?
Doesn't something like this already exist?
How will you get costs down?
Where will you manufacture?
Where will you be based?
What's your marketing strategy?
Why does anyone need this?
Why should anyone do this?
The possibility of succeeding in that kind of capital-intensive, winner-take-all environment has always been much lower than in finding a small niche related but adjacent to a massive boom and building a business there.
Herb most definitely did not want Southwest to meet the same fate. "So I used the line, "Think small and act small, and we'll get bigger. Think big and act big, and we'll get smaller," he told me of that letter to his employees. He cautioned them not to think or act like the bigger airlines, not to be enamored of what it appeared they had, and not to compete with them on their terms. Instead, if Southwest just stuck to what they did best, he believed, if they operated within their means and according to their founding principles, if they stayed in their lane, everything would work out, and major opportunities would present themselves. In short, if they thought small and acted small, the sky would be the limit.
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