bookworm

The Messy Middle – Scott Belsky

Review

This book covers a lot of ground, for an inexperienced entrepreneur about to build a company it would be life changing. It’s a book of common sense, and there’s an incredible amount of wisdom in here. That said, if you’ve been around the block a few times there isn’t much ground breaking or new insight in here.

A must read for entrepreneurs – pair with the Y-Combinator video series ‘How to Start a Startup’ and you’d have a great overview of the problems you’re likely to face and how to navigate them.

Key Takeaways

The 20% that gave me 80% of the value:

  • The Messy Middle often isn’t chronicled, because its unappealing and too revealing. Nothing headline worthy yet everything important.
  • How do you survive long enough in an industry you know nothing about until you become an expert?
  • You need to develop a source of renewable energy → Without any customers or evidence of progress, without a steady stream of rewards, you will feel empty. You have to manufacture optimism

Endure

  • You can get the important stuff right and still lose by not enduring enough
  • Change your path but not the destination
  • Leave conversations with energy (especially when answers are not clear). Be an energy giver not a taker, leave people with more energy than when they start.
  • Self-awareness starts with the realization that when you’re at a peak or valley, you’re not your greatest self.
  • You are many decisions away from success, but always one away from failure.
  • Your weird is the source of your power. Don’t try to fit in, with what is common and familiar.
  • Don’t do insecurity work (no intention, doesn’t move things forward, so quick you can do it a few times a day)
  • 6 phases of leading a reset: feeling anger, removing yourself, dissecting the situation, acknowledging your role, drafting your narrative, and then getting back into the game.
  • Few people can stay loyal enough to strategy to have their vision realized. That’s the hardest part
  • Bezos focused on the long term. If we have a good quarter, it’s because of what we did 3-5 years ago. There’s a massive lag between innovations and results
  • The easy path will only take you to a crowded place. There’s often an easy option and a best option. Your competitors can follow the easy option.
  • Break long term goals down into chapters.Chapters are clear goals – underscored by why they’re important – teams do tactics
  • To disrupt and industry be a thesis driven outsider → and stay alive long enough to become an expert
  • The best way to complain is to make things. If you’re actually willing to do the work, you’ll have more influence than those who simply do their jobs.

Optimize

  • Why did that work? How do you do it again? Optimize the hell out of everything that gets traction
  • Optimization stems from a conviction that you can do better.
  • On building teams…
    • Resources become depleted, resource-fullness doesn’t.
    • Refactor, Refactor, then hire. Initiative > experience. Diversity drives differentiation
    • Sometimes you’ll need to suppress the team’s immune system to get change through.
    • Foster Psychological Safety – build risk taking into the system. Top teams report more mistakes. Free to share things without recriminations
    • Foster apprenticeship – find a way for the new to work with the experienced.
    • Shed the bad to keep the good – balance the needs of individuals with that of the team and the mission. People need to admire their team members and see their commitment.
  • Culture is created through stories – the early ones are very important (Jeff Bezos desk doors). Helps team members work out if something is uniquely x, or not… and right from wrong
    • We make stuff often, and therefore fail often.
    • Be frugal with everything except your bed, your chair, your space and your team
    • We vastly underestimate how much the products we use impact the products we create.
    • The person who did the work should present the work. Be wary of false attribution
  • Never outsource your competitive advantage
  • Install process for your team, to solve their problems, not to quell your anxiety.
    • Give them problems, let them choose how to work through them. Respect people’s work styles
    • Done walls – decorated with completed project plans and checklists
  • Present your ideas don’t promote them
  • Delegate – entrust – debrief – repeat
    • make sure everyone knows what they’re doing and how it contributes to the mission / vision
  • Postmortem everything
  • Be explicit when you are asking for something – you’re more likely to get what you want
  • There is power in brevity
  • Leaders who can’t make decisions accrue organizational debt.
  • Our desire to make progress means we don’t tackle the bigger more important problems
  • Observe and learn, don’t emulate.Be your greatest competitor
  • The greatest thinkers anchor their ideas around a central truth, one that they believe is unique and unrealized by others.
  • The greatest risk is taking a shortcut in the one area that distinguishes you the most
    • every product has a few differentiating attributes, don’t take shortcuts, rush, or strip down the process of creation for these features
    • speed through the generic stuff – take time to perfect the few things that you’re proud of
  • Asking for permission leads to hesitation or rejection.
  • Very few critical and difficult decisions can be made in a group. BUT the knowledge around you is greater than the knowledge within you. Tap into the knowledge, but don’t give tough problems to committees.
  • Simple is sticky. It’s hard to make a simple product, it’s even harder to keep it simple. Make one subtraction for every addition
  • The greatest cost of trying to sustain too many initiatives is having too little to thrust behind each goal
  • Beware of creativity that compromises familiarity
  • Effective design is invisible, good design is as little design as possible
  • Never stop crafting the first mile of your products experience
  • Do > Show > Explain – getting new users to do something is the most powerful onboarding
  • Break incrementalism by questioning core assumptions
  • You don’t want all the customers straight away. You want to right group to start iterating with
    • The ideal customer is … Willing > forgiving > viral > valuable > profitable
  • Build your narrative before your product
  • Best to market > first to market
  • identify and prioritize efforts with disproportionate impact
  • engagement drivers (long term) interest drivers (short term).
  • The information gap. First a situation reveals a painful gap in our knowledge (headline) then we feel an urge to fill this gap and ease that pain (we click)
  • Loewenstein outlines 5 curiosity triggers:
    • questions or riddles
    • unknown resolutions
    • violated expectations
    • access to information known by others
    • reminders of something forgotten
  • Skills and relationships transcend the success or failure of a project
  • If somebody asks you to do something, ask them 0 – 10 how much are you asking me?
  • Mine contradictory advice and doubt to develop your own intuition
  • The danger with measures is their gravity, and how quickly they dictate our daily actions
    • Measure each feature by its own measure – determine what each measure is intended to achieve and measure it accordingly. Tow hooks aren’t meant to be used all the time – but they need to be discoverable and effective when needed
    • Avoid having too many metrics – the more you track the fewer you’re focusing on changing
    • Boil the business down to one or two core metrics.
    • Keep evaluating their efficacy and alignment with your long term goals
    • ‘People don’t use that’ is not deep analysis. We don’t want people to use password reset functionality but we should have it
  • Do things that don’t scale in the beginning -don’t forget the little things as you scale
  • Two types of commitments:
    • Active Commitments: investments of time, energy and resources in areas you willingly choose to love and pursue
    • Passive commitments: commit to doing something that doesn’t align with your interests. Operating out of guilt rather than intention
    • When you stop nourishing something let it go. Everything you do should be an active commitment or nothing at all
  • Build a network that amplifies signal – after a while, you need a strong filter, you need to discriminate your information source

The Final Mile

  • keep repositioning the ultimate goal as being the furthest away point that you can see

Bojan

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