My Messy Middle: between the pains and pleasures of building our vision
“You’re either part of the living or the dying.”
Scott Belsky, The Messy Middle, p. 368
Perhaps this one line captures the essence of Scott Belsky’s, The Messy Middle. I knew instantly from this title that Scott would get it right — “it” being the true realities of starting a company. We have a habit of glorifying starts and finishes and the peaks and troughs in between. We sensationalize beginnings, ends, and those “ah-ha” moments that fit easily into #success or #failure. And of course, with this comes the peanut gallery’s “told you so’s” and “knew it all along’s.” But in The Messy Middle, Scott takes us down to the trenches where the real war is fought and reminds us what it really means to “win” in building a company.
What I write here can’t truly capture the rich and dense value of The Messy Middle. You can pick up almost any part of the book and learn, relearn, or refine an important tenet of business and life. So rather than write essentially another book that unpacks my views, I’ve focused on the 3 pillars of wisdom that Scott imparts, especially as they relate to my own experiences.
1. Endure
The easy path will only take you to a crowded place.
HBS Professor Howard H. Stevenson defined entrepreneurship as “the process by which individuals — either on their own or inside organizations — pursue opportunities without regard to the resources they currently control.” As this quote implies, entrepreneurship takes many forms beyond simply starting a company; being an entrepreneur is to trot a different course, to eschew the easier paths set out for you by the world as it stands and to embark instead on a harder but more fruitful journey.
I’ve always been an entrepreneur, constantly forced to forge new paths to survive the consequences of systems that have failed me. Echoing this philosophy, Scott invokes the Roman emperor Marcus Aurelius as he writes, “The impediment to action advances action. What stands in the way becomes the way” (39). Indeed, growing up in a single-parent home scourged with domestic violence, drugs, and homelessness, I was without peace of mind and far from content for most of my adolescent life. However, the real hell for me would’ve been to accept this as a fixed reality. In that darkness I saw that taking easier paths like shirking academics, accepting low expectations and buying into the chaos would only lead to harsher realities. I witnessed friends abandon school for drugs that led to pain as far as death. And yet, it is from our struggles that we must find the impetus for success. As Scott aptly puts it, “this book is about mining every insight from the volatility and the depths of despair to improve your team, product, and self” (8) — hardships should not be feared but harnessed. Choosing harder paths and often times, paving one’s own path, is the only way to find greener pastures.
This principle comes in all decisions when building a startup. The Messy Middle makes it clear that the right decision isn’t usually the popular one. Take, for instance, an entrepreneur like Jeff Bezos who left his hedge fund salary at D. E. Shaw to sell books. Certainly not a coveted career change at the time, but twelve digits later no one would act differently. We constantly deliberate on new and fringe ideas but too often fall into the trap of familiarity. As Scott writes, “one of the worst tendencies of the messy middle is pulling wildly fresh insights back toward the mean of normalcy” (58). To truly succeed, we must overcome this tendency, embracing new ideas rather than fearing them.
For me, deciding to create Astorian while still in college and supporting my 3 younger siblings was daunting. And of course, safer paths appeared along the way with offers from J.P. Morgan, Google, and the sort. But none of that could divert me from my mission, which was more than simply escaping those failing systems I’ve endured, but being able to bring everyone else along with me. “Playing the long game,” as Scott puts it, “is the most difficult one to play and the most bountiful one to win” (85).
2. Optimize
Refining product and self
Endurance is valuable, but it can only take you so far — persistence devolves to foolish repetition if it isn’t relentlessly optimized. From start to finish, we each experience a range of failures and successes that have the potential to shape us for better or worse. And with guidance from those who have walked ahead of us, we can see how to transform these experiences into lessons for improvement.
In The Messy Middle, Scott reveals his battle scars from building Behance and Adobe, imparting the kind of hard-earned wisdom only a wife of 30 years could give to a bride-to-be. This is my favorite part of The Messy Middle because it’s the most relevant for us at Astorian right now. In the section “Kill Your Darlings,” Scott writes about his friend Tim Ferriss who implores us to ask, “’If you had to keep 10 percent, which 10 percent would you keep and if you had to, absolutely had to, cut 10 percent, which 10 percent would you cut?’” (221). We work so hard to build, that often we do too much building and not enough cutting — stacking things atop one another until we’re left with what my co-founder Aaron once called, “a weird, hybrid bastardization of our true intent.”
Ultimately, optimization is a constant need for a growing startup, and one of my favorite pieces in this section of the book is “Never stop crafting the ‘first mile’ of your product’s experience.” In this section, Scott implores us to take extra care in the very first interactions we have with our customers. At Astorian, this first mile comes in our pitch to clients, and while we have had a 100% conversion on in-person meetings with property managers, we remain hyper-focused on refining the perfect message. That’s why we record sales meetings and treat them like game footage to analyze and factor into the next. And no matter how good we feel about any given pitch or facet of our business, we remain in pursuit of the global maxima because perfection is dynamic. John Milton captured this best when he wrote, “God made thee perfect, not immutable.” Perfection evolves and so must we.
3. The Final Mile
You’re either part of the living or the dying.
The third section of The Messy Middle, “The Final Mile,” takes aim at the aspect of the peanut gallery’s take on entrepreneurship that most often goes unquestioned. Outsiders are quick to categorize, quick to jump to a binary conclusion — you’ve either crashed or succeeded. But underneath the classic headlines, we see that it’s never that simple. First, in all failures wisdom can be derived and therefore winning is not restricted to success as we usually think. Conversely, success can often dull one’s blade, resulting in outcomes we’re not actually happy about. As Bain said to Batman in The Dark Knight Rises, “Peace has cost you your strength. Victory has defeated you.” Success and failure are the same — we either learn from them and grow or we let them destroy us.
Nevertheless, it is hard to escape feeling frustrated when stuck in one of the troughs of our messy middles. And for those moments, there is a quote from this section that will remain with me forever, “You are either part of the living or the dying” (368). This simply means that in any setting, no matter how agonizing, we have a choice on where we devote ourselves. Are we to focus on the uncontrollable realities of our situation or the surmountable challenges? If there ever is a solution to be found, is it to be found in despair or in hope? Personally, I prefer to understand what I can control and devote myself to the challenges, as I’ve seen time and again that that is how we embody our highest potentials and truly win these battles.
So what does it really mean to be victorious? I should know, it’s my name. At its root, Victory means to overcome, which is what bold ventures are all about. We are overcoming problems and forging new paths. Every problem resolved and solution created spurs more to consider, like a hydra that keeps us ever striving for more. As we and the world constantly progress, our views evolve, refining and shaping our convictions. But ultimately, as Scott writes, “to be done is to die.” (373). Thus, no matter what phase we’re at, it is imperative to never be done with what matters the most and that is remaining true to our convictions.
And so I wade through the waters of my messy middle, holding on to my conviction that it is far better to die on my feet, doing what I love, than live on my knees, subjugated to the world’s whim.
Special thanks to Scott Belsky for writing The Messy Middle; to Silicon Valley Bank and Jeremy Shure at SVB who gave me a second free copy of the book after he saw my highly-annotated version at Scott’s talk; our investors, Erik Torenberg and Anne Dwane at Village Global; everyone at Rough Draft Ventures; and our supporters at Yale, MIT, and Wharton.
