Scott Belsky
The Messy Middle
ISBN: 978-0-7352-1807-9
I picked up The Messy Middle after listening to Scott Belsky’s keynote at EntreFEST 2018. If you follow this blog, I reference that keynote quite a bit when talking about the struggles and trials that entrepreneurs endure during the creation of their companies, and how it differs completely from the big celebrations we have at the beginning and end of each startup. We routinely have a big push for startups at the very beginning of the process with events like Iowa Startup Games and Startup Weekend Iowa City, and then either celebrate an acquisition or, in the case of one startup here in the area, wrap up the company with a “startup funeral.”
We very rarely talk about what goes on for years and years behind the scenes of a startup – worrying about being able to pay bills, struggling to get and keep paying customers, dealing with employee issues, finding true product-market fit. Most entrepreneurs are going through the struggles alone, as many spouses don’t understand entrepreneurship and there are a lot of things you can’t share with your employees, depending on the culture of your company. A few lucky entrepreneurs have a peer group to share their experiences, but those are few and far between in many parts of the country. Just knowing that others share your experience can be a breath of fresh air, and this book delivers it.
Rather than consisting of one long narrative meant to be read in one sitting, The Messy Middle is a series of several dozen short stories – some only two or three pages long – that are grouped based on the stage in which you find yourself. Most of the book falls into two categories: “endure” and “optimize.” These two sections really do work in tandem – much of the energy spent on a startup is enduring different situations, both good and bad. Startup founders should try to optimize for the good times, in an effort to better weather the bad times. Belsky gives tips on optimizing team, culture, tools, workspace, communication, product, and (most importantly) yourself.
The book spends a decent amount of time on self-care, which is something I see many founders neglect. Grinding away at your business constantly tends to become a status symbol in the startup community. In reality, it winds up leading to burn out and dissatisfaction with the startup ecosystem. At times, I have trouble with self-care, because I want things to move along as quickly as possible. I know I don’t exercise enough and my diet can be complete garbage at times, especially when I’m traveling. To stay aware of your weak spots is the first step in addressing the problem, and can prevent bigger problems from forming in the future.
The book may be called The Messy Middle, but what about the finish? For serial entrepreneurs who have already exited one or more times, this section may not be necessary. However, I appreciate Belsky including this at the end of the book. The main message of this section was one of the greatest takeaways of the book: never be finished, and don’t ever stop learning. As Belsky titled one of the final chapters of the book, “To be done is to die.” Every experience you have is an opportunity to learn something. If you don’t learn something, you’re not doing something right.
Overall, 10/10, would highly recommend to all startup founders, both seasoned experts with multiple exits, all the way to young people who have just taken the step to form an idea into a startup. There are parts of the book suited to anyone on the startup journey. This is a book I plan to read again at some point in the future, as my journey through the entrepreneurial ecosystem continues, and I have new experiences that shape the lens through which I look. Treat this book as a reference, and keep it on your shelf, both for the good times and the rough. You’ll be glad you did.