"The Messy Middle" by Scott Belsky

Book Summary:

“The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture” by Scott Belsky, is an indispensable guide to navigating the volatility of new ventures and leading bold creative projects.

Creating something from nothing is hard, but the unpredictable journey can be even harder. People love talking about starts and finishes, but often ignore the middle stretch even though it is the most important and often the most misunderstood part.

The book has 100+ lessons and will help you:

• Endure the roller coaster of successes and failures by strengthening your resolve, embracing the long-game, and short-circuiting your reward system to get to the finish line.

• Optimize what’s working so you can improve the way you hire, better manage your team, and meet your customers’ needs.

• Finish strong and avoid the pitfalls many entrepreneurs make, so you can overcome resistance, exit gracefully, and continue onto your next creative endeavor with ease.

With insightful interviews from today’s leading entrepreneurs, artists, writers, and executives, as well as Belsky’s own experience working with companies like Airbnb, Pinterest, Uber, and Sweetgreen, The Messy Middle will help you find your way through the hardest parts of any bold project or new venture.

Author Bio:

Scott Belsky is an entrepreneur, author, and investor. He is currently Chief Product Officer at Adobe, serves as a board member to several early-stage companies, and is a Venture Partner at Benchmark, a leading venture capital firm based in San Francisco. He was previously the founder and CEO of Behance. He is also the creator of 99U, Behance's think tank and annual conference devoted to execution in the creative world.

Author Scott Belsky ( all images credit to Scott Belsky ).

Author Scott Belsky (all images credit to Scott Belsky).

Book Lessons:

1) It’s not about the start or finish, but the journey in between

The middle makes and breaks you, and ending up on the right side of this line depends on how you manage everything in between. It requires immense perseverance, self-awareness, craftsmanship, and strategy.
— Page 12

People love stories about success, especially about how a small team that worked really hard with little funding was able to build a startup and sell it in just a few years for millions of dollars.

However, that story is missing one very important part, the messy middle.

The messy middle is about all of the obstacles and the signed deals, the disappearing customers and the move to pivot, the employee that stole secrets and the day the team signed their first major client.

The messy middle is the journey all creative endeavors encounter, from the highest highs to the lowest lows.

For instance, take Scott Belsky’s company Behance.

He founded the company in 2006 to connect and empower creative professionals. The team bootstrapped the business for five years before one of their products gained traction and he was able to raise venture capital. He used the money to grow the business and in 2012 Adobe knocked on their doors and acquired the company.

Simple and easy right?

On the surface, yes, but the true story went something like this:

There were years at Behance when nobody beyond the team could understand or care about the work they were doing. The company was on the brink of falling apart more than once. In the early days, Scott had to take anti-nausea medication because it was the only way he could keep an appetite. In the first year, there were only four employees, each unqualified for the journey ahead, but they were the only ones crazy enough to accept the risks and join the journey.

So how did Scott Belsky manage to survive the messy middle?

That is exactly what this book is about.

The Myth of how people believe building a business works.

The Myth of how people believe building a business works.

The Real Journey of how building a business looks like.

The Real Journey of how building a business looks like.

2) Resourcefulness > Resources

Too many teams hire when they should be optimizing the people they’ve already got. You can always get more resources, but resourcefulness is a competitive advantage. Resources become depleted. Resourcefulness does not.
— Page 100

As Scott was growing Behance, his engineers had a list of people they “absolutely needed” to hire. The problem was that the designers and community management and support teams, all had similar lists as well.

Since the company was bootstrapping and had very little capital to hire anyone, Behance’s head of operations, Will Allen, advised the teams to come up with a list of process improvements they could make with their existing time to improve productivity without having to hire a new person anytime soon.

Here are a few questions you can ask your team before hiring an additional team member:

  • Are there better tools that could be adopted?

  • Can some of the work be automated?

  • Are there time-consuming processes that can be killed?

Scott points out that by not having the resources available to hire more people, his teams would uncover serious inefficiencies and exciting opportunities to boost productivity.

The team became more efficient before they became bigger which allowed them to attract high-quality individuals because efficient people want to work in an efficient environment.

“Resources come and go, but resourcefulness is a muscle that kicks in throughout the life cycle of any business. Without it, capital cannot be used efficiently. Focus on building your team’s resourcefulness” (pg 102).

3) Be frugal with everything except your bed, your chair, your space, and your team.

In the process of building a business–and in life, generally–you should manage expenses carefully. But sometimes frugality backfires.
— Page 140

The author goes on to write that there are a few things in life, and business, that you should not be frugal with. For instance, given that you spend about 30% of your life in bed and since sleep is so important to being healthy and productive, you should not try to cut costs on getting a good bed.

The same goes for office chairs and desks. So people spend more time in the office sitting in their chair at their desk than they do lying in bed, so go out and find the best chair you can find.

Scott also advises companies not to be frugal with their office space. The space should be designed based on making people productive and creative, not on focusing on the cost per square foot or logistical efficiencies.

One of Scott Belsky’s mentors, James Higa, spent a lot of time with Steve Jobs through his time at Next, Apple and Pixar. James said that Steve would fly around the world to acquire Japanese American sculptures and put them in the building’s lobby just so employees could have a “daily encounter with beauty.”

Similarly, at Apple’s new Spaceship campus, Steve wanted the bathrooms to be placed in the building’s center so that it would pull people together every day and promote “serendipitous idea exchange” when nature called.

Steve Jobs had many responsibilities, including leading Apple, and yet he chose to focus on office space because he knew the importance environment and design had on employees and the company.

Lastly, don’t be frugal when it comes to paying your team, writes Scott. Sure, a company can get away with underpaying someone in the short term, but great talent will recognize their value over time and at that point, the company will have to pay the price to either attempt to save them, or worse, have to replace them.

“Your team must feel taken care of and must have no doubt that they are being rewarded as best as possible for their achievements–and then a little bit more” (pg 142).


The Messy Middle” is a wonderful guide for the entrepreneur or business owner that is growing their business and is facing, well, the messy middle. The book teaches readers how to endure the low points of hard truths, facing failure and keeping the business alive.

It also talks about optimizing the high points of the journey including what to look for when hiring people, how to design office space, and how to continue scaling the business.

This is a very brief summary, there are countless more important lessons to learn from this book.

The book also isn’t one long story, but rather each lesson has a one to three-page mini-story from either Scott’s personal experience or wisdom gained from a close friend or fellow entrepreneur, which is great because it’s not just theory, but rather filled with real world examples.

To conclude, I would highly recommend reading this book, but only for a specific audience. For instance, if you are a founder, entrepreneur, business owner or manager, then you should get this book. It will teach you how to survive and thrive through the hardest parts of growing a business. If you have yet to start a business, put this book in your cart and buy it when you do.

Rating: 4.5/5 stars

If you’re interested in reading the book, click here or on the image below.

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For literally a few dollars and hours of time, a book will give you an enormous amount of valuable information that can help you in life. It’s practically highway-robbery. So take advantage of this and read as much as you can.

If you want to check out my list of recommended books, you can find that here.

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