The Tim Ferriss #336 How To Conquer the Messy Middle

  • Scott’s eclectic bio in chronological order: Founded Behance 👉Adobe buys Behance 👉Worked as VP at Adobe 👉 Seed investor 👉Venture Capitalist at Benchmark 👉 Chief Product Officer at Adobe 

  • Scott takes a lot of notes: They are organized around 3 themes. (1) Endurance (2) Optimization (3) The Final Mile. Scott writes about this in his book The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture.

  • Endurance: How do you navigate the endless, uncertainty, ambiguity, and extraordinary volatility around bold projects? How do you develop the persistence and patience? 

  • Optimization: How do you make the product better? How do you make the team better? How do you improve how you work? 

  • The Final Mile: What happens when something is almost done. This could be the sale of a company or the design of a product. There is a lot of interesting stuff that happens here. You think you know what you are doing because you got that far and then you realize Oh Shit! I don’t know what I am doing.

  • The idea behind Behance: Creative people are some of the most interesting people in the world. They make our lives interesting. It is the most disorganized community on the planet. Our job was to help organize it. To build a LinkedIn for the creative world. 

  • The idea is enough to get you started. An idea is not enough to keep you engaged on a daily basis for years: The myth is if your vision is great enough you can just keep persisting. In fact you need to short circuit your reward system. From birth we are oriented toward short term rewards. Set unique short term rewards in line with your long term vision.

  • What do you do when you feel scattered or overwhelmed? Do your fucking job.

  • Helpful for entrepreneurs: The realization that I am not my best self when things are going the best. [Because my ego can get in the way. We start to think we don’t have to pay attention to competition anymore. We take our eye off the ball. We must have done everything right so we will keep doing it.] And the realization that I am not best when things are going badly. [Because my fear is getting in the way. I’m paying too much attention to the competition. I’m copying other products.]

  • How to not spread yourself too thin: Make a list of everything you want to do. Decide which one or two things will have a disproportionate impact. Go all-in on those. People resist doing this because they have doubts and want to hedge. Don’t. You have to be provocative. 

  • How Larry Page [founder of Google] jolts the system: In a meeting he’ll say good plan. How do you do 100x that? That throws the current product plan out the door. All the near term doubts you have don’t matter anymore. 100x? We have to be doing something completely different.

  • Lesson learned from the founder of Pinterest: Building a company is a long journey. Break it down into chapters. The first chapter was get to product market fit. The next chapter was growing the international user base. The next chapter was figuring out the business model. It keeps the team engaged over the long term.

  • What do you read when it comes to entrepreneurship?: Ben Thompson’s StratecheryTren GriffinJosh Wolfe.

  • Book recommendations: I like to read biographies. Doris Kearn Goodwin’s booksWalter Isaacson’s booksEndurance: Shackleton's Incredible Voyage.

  • What Tim learned from Robert Rodriguez: Filmmakers come up to Robert complaining about all the things that did not go according to plan. What they don’t realize is that is the job. If you sign up to be a filmmaker your job is nothing will go to plan. Find a way to make it work. Applies to entrepreneurs too.

  • In startups, resources are like carbs. Resourcefulness is like muscle: Once you develop it, it stays with you. Resourcefulness impacts everything going forward. When you are bootstrapped you are forced to develop that muscle. That serves you forever.

  • Remember this when building a product: We have way too much faith in people unearthing the value of what we are building. In the first 30 seconds of any experience of a new product, every customer is lazy, vain, and selfish.

  • When thinking about onboarding first-time users: A lot of products that succeed quickly give you a template. They do it for you. They make you seem so much better than you are. You should spend a ton of time on crafting the first-mile experience for your customers. 

  • Classic behavior in every product release: Last-minute churn. Second-guessing. Not ready to ship yet. Maybe I should have done something else. Maybe I should cut this part out. It’s a psychological breakdown. You have to be prepared for it.

  • Full podcast here.