The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

by Scott Belsky

Although you should follow them closely, don’t become defined by your opponents. If you focus more on your competitors than on your own customers and your own unique approach to serving them, you lose your identity. Stay tuned but not governed by what’s going on around you.

Creative block is the consequence of avoiding the truth.

creative block is the consequence of avoiding facts that provoke uncertainty, fear, and confusion. Avoiding these obstacles to focus on the task at hand is appealing and can work in the short term. But avoidance creeps up on you.

To conquer creative block, you must ask bold questions and shine the spotlight on the elephants in the room. Perhaps the product is shitty. Perhaps your business model and all the assumptions leading up to it were fundamentally flawed. The truth will hurt, and it may set you back temporarily, but it will ultimately set you free.

“What distinguishes great founders is not their adherence to some vision, but their humility in the face of the truth.”

Be open, humble, and eager to learn that you’re wrong—before someone else does.

Moving fast is great, so long as you slow down at every turn.

Whatever you build and launch to the world becomes much harder, both logistically and psychologically, to change after launch.

If the uniqueness isn’t already baked in, and instead only gets sprinkled on top, it’s likely to taste bland.

Speed through the generic stuff, but take the time you need to perfect the few things ...

Value the merits of slow cooking.

Miraculous things are possible when you allow yourself to pursue an idea slowly. Like fine wine, the longer you can leave the grapes on the vine—and the wine in the bottle—the more complex the flavors become.

“Ask for forgiveness, not permission.”

Society tends to eventually celebrate what was, at first, shunned. Companies are no different. If you can withstand some tyranny, you’ll be rewarded for it.

Oftentimes, the best way to proceed is by charging ahead without too much reliance on the processes developed to maintain the status quo.

Conviction > Consensus

Optimization requires decisiveness. As you improve your product, you will be torn between appeasing your customers and sticking to your own beliefs.

You will look to groups for decisions when you should be looking to them only for guidance. The best decisions tend to be the hardest and least popular. When you feel lik...

Decisions based on consensus typically end up with an ordinary outcome because by seeking to please everyone, you boil your options down to their lowest common denominator: whatever option is most familiar to the most people and therefore gets the least protest and the fastest support.

The best investors don’t grasp too tightly to any given playbook. As a seed investor, I am always trying to use my pattern-recognition abilities without holding on too dearly to whatever worked before.

For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.

Don’t give those resistant to change false hope.

When you make a bold decision that changes your strategy and the day-to-day responsibilities of your team, your job is to foster alignment.

In retrospect, I believe avoiding these confrontations gave the resistant teams a sense of false hope that they wouldn’t have to change much after all.

This may have set us back years. Sometimes you let your customers and team lead, and other times you must push your customers and team into the future.

Hesitation breeds incrementalism—the tendency to make changes too muted, too slowly, and too late. You need to attack the hesitation and galvanize the tr...

you need to decide what aspects of your team and product distinguish you most—and what you’re willing to be bad at.

But the greatest cost of trying to sustain multiple initiatives is having too little thrust behind one goal. When a goal is simple and singular, every realization builds upon the one before it.

Creative writing is a war between simplicity and possibility. An

Disney reportedly implemented a staged process utilizing three distinct rooms to foster ideas and then rigorously assess them.

Room #1: In this first stage, rampant idea generation was allowed without any restraints. The true essence of brainstorming—unrestrained thinking and throwing around ideas without limits—was supported without any doubts expressed.

Room #2: The crazy ideas from Room #1 were then aggregated and organized in Room #2, ultimately resulting in a storyboard chronicling events and general sketches of characters. Rumor has it that the origin...

Room #3: Known as the “sweat box,” Room #3 is where the entire creative team would critically review the project, again with no restraints or politeness. Given the fact that the ideas from individual people had already been combined in Room #2, the criticism in Room #3 wa...

Your best chance of succeeding is to consolidate your energy around a singular focus and work like hell to achieve it.

If you don’t think it’s awesome, stop making it.

Every venture is hard, and every great team loses momentum once in a while. I think the ultimate litmus test is whether you have more or less conviction about the vision than you had at the start.

If you still believe that what you’re building needs to exist—and the time you’ve spent on the project only deepens your conviction for the change you will make with your product—then stick with it.

most decisions aren’t like that—they are changeable, reversible—they’re two-way doors. If you’ve made a suboptimal Type 2 decision,

“As organizations get larger,” he explained, “there seems to be a tendency to use the heavy-weight Type 1 decision-making process on most decisions, including many Type 2 decisions. The end result of this is slowness, unthoughtful risk aversion, failure to experiment sufficiently, and consequently diminished invention. We’ll have to figure out how to fight that tendency.”

The best products become more effective over time, not more creative.

In order to disrupt an industry, our instinct is to be different. But the best way to capture the share of an existing industry is to be familiar.

Too much scrutiny creates flaws.

If you scrutinize too much, however, you’ll eventually reach what I call the “cohesion horizon,” where your scrutiny loses perspective, and you start perseverating over details without context and stop evaluating the whole.

The best design often goes unnoticed because something is removed that wasn’t meant to be there in the first place.

Whether you’re building a product, creating art, or writing a book, you need to remember that your customers or patrons make sweeping judgments in their first experience interacting with your creation—especially in the first 30 seconds. I call this the “first mile,” and it is the most critical yet underserved part of a product.

Optimize the first 30 seconds for laziness, vanity, and selfishness.

When bringing a new product to market, you’ll be tempted to explain what it is and how it works. Such attempts usually result in extensive amounts of copy, how-to videos, and multisequence digital “tours” explaining the product’s purpose and how to make the most of it.

If you feel the need to explain how to use your product rather than empowering new customers to jump in and feel successful on their own, you’ve either failed to design a sufficient first-mile experience or your product is too complicated.

Having to explain your product is the least effective way to engage new users.

Novelty precedes utility.