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“Free Solo” and the Tech Bootstrapper: 5 Clear Parallels

In the summer of 2017, Alex Honnold accomplished the impossible by free soloing Yosemite’s daunting 3,200-foot El Capitan. In the climbing world, free soloing could be considered a “sub-specialty” where the climber ascends a rock-face without the use of any safety equipment.

In the documentary “Free Solo,” filmmakers Jimmy Chin and Elizabeth Chai Vasarhelyi follow Honnold’s preparation for, and ascent of, the formidable face. In accomplishing the climb with no rope, no safety net, and nothing to catch him if he were to fall, Honnold and his film crew delivered an incredible story that is equal in its ability to inspire, terrify, and bewilder. 100% of it is real, factual, raw, and astounding. As I watched Free Solo last night with my wife, I will admit my palms were probably sweating more than Honnold’s did while accomplishing what the New York Times called “one of the great athletic feats of any kind, ever” in its front-page story on the achievement.

The bottom line is that such a feat seems nigh impossible. The notion of climbing nearly two-thirds of a mile into the air without safety equipment makes me nauseated…and I grew up back-flipping off of 30-60 foot cliffs into the waters of Lake Powell, my childhood vacation paradise at the Southern Utah and Northern Arizona border. Natural-born thrill seekers look like comparatively fainthearted homebodies when considering the enormity of Honnold’s accomplishment.

As Free Solo’s closing credits rolled, I sat in inspired-silence trying to grasp the nature of a person such as Honnold, the calculated risk, the preparation. Immediately (and I think reasonably), my mind was pulled to the makeup of the class of entrepreneur that I have obsessively built my career understanding, consulting, and serving in my M&A practice: the technology bootstrapper. As I considered the content that I had just voraciously consumed, it was perhaps not surprising that I instantly saw a multitude of parallels both between the nature of free-soloing and bootstrapping and between Honnold and the bootstrapping entrepreneur. While the journey of the bootstrapper is not usually “life and death,” the risk profile that one must embrace to successfully bootstrap is probably closer to that of the free-soloist than that of the more traditional, talented mountaineer.

The Rope and the Climbing Partner (“without safety net”)

Ironically, the night before I viewed Free Solo, I had dinner with a prospective client that I feel is nearly a perfect fit for my M&A firm (for many reasons). During a six hour discussion before and during dinner, we talked about some of the reasons that the founders were considering a transaction. One key theme that came up (word-for-word) is that continuing to bootstrap had become more and more like “climbing without a safety net” and they feared that doing so could negatively impact the product, the team, and the families of all stakeholders. One of the founders expressed that, in a way, the more successful the company gets without a funding partner (i.e. the higher they climb in their “free solo”), the greater the risk (the further they can fall / the more value can be lost). As in free soloing, this is a simple but important truth.

This desired shift in risk profile is not an uncommon or irrational experience among bootstrappers. In fact, like Honnold eventually considering the decision to free solo “less often,” the exercise is actually likely to precede the move to a more rational state. After talking with hundreds of bootstrapping founders (and perhaps into the thousands) over my 15 year career, one of the most consistent feelings (whether fully steeped in reality or not) is that the business is one bad move, one “shift in conditions,” away from death. The parallel with the ever-present reality in the free solo climb is striking.

In almost all cases, my clients hire me to help them transact not because they have lost their passion, would like to retire, or feel that the business has reached “the pinnacle.” It is because their past ascents (successes), their willingness to take the big risks, and their unique ability to mentally tussle with – and succeed in the face of – the business equivalent of “free soloing” has led them to an altitude where they no longer wish to “tempt fate”…no matter how much they love doing so or how “alive” it makes them feel. I am hired to help them find the right “safety equipment” and the ideally aligned “climbing partner” so that they can continue the ascent in the field that they love – only in a more appropriate, risk-adjusted state.

Picture Credit: “Free Solo” – Nat Geo

The Passion

Bootstrappers are passionate, talented, and gritty; my slightly biased opinion is that they are more adept at identifying product-market fit than any other class of entrepreneur. They are willing to put it all on the line because they believe in their vision so completely, and they are willing to do the work to reach the summit because they know that the view from the top will be grand. They take out second mortgages, rack up credit card balances, and work for years without income because the destination, as well as the harrowing journey, is worth it – even if the risks are un-paralleled in the business world. That passion-fueled drive is what leads them to success despite the pitfalls, exhaustion, and tremendous risk that faces them daily – not too unlike the experience of the free soloist.

The Product, Perfectionism and the Stakes

A perfectionist since he was a boy, Honnold has long felt that free soloing is as close to “perfect” as one can get. However, the stakes are basically infinite in their impact due to the perfect finality of any unsuccessful ending. Honnold’s friend and training partner Tommy Caldwell, who has also scaled El Capitan numerous times – but never without a rope – put it this way:

“Imagine an Olympic gold medal-level achievement where if you don’t get that gold medal, you’re going to die… I think everyone who has made free soloing a big part of their career is dead by now”

While it would be an unreasonable stretch to say that the stakes are just as high for bootstrappers, the parallels are there, particularly when it comes to bootstrappers’ tendency toward perfectionism as well as the reality of an environment that almost necessitates it. From day one, a bootstrapped business must deliver a product so good that its sales can sustain operations without “a safety net” and often without the resources to hire “climbing partners” (sales staff) to help it do so. The product must allow for a successful market “ascent” despite the perils of heavily funded competitors, market noise, and competition for team members on a tight budget. In an environment like this, given all the many constraints, execution must be almost perfect.

One possible reason Honnold is so good at free soloing, doctors hypothesized after giving him an MRI, is that his amygdala, the part of the brain that regulates fear, doesn’t react to potentially stressful or frightening inputs the way it does in most people. I would certainly not be surprised if top bootstrappers’ brains showed similar patterns.

The Team, a Sometimes Lonely Journey, and Shifting Risk Profiles

Once it became clear that Honnold fully intended to free solo El Capitan, his filmmakers hesitated, putting the project on hold for a few months due to ethical concerns: What if the pressure of being filmed somehow affected his climb? What if he fell to his death with their cameras capturing the tragedy? And what about Honnold’s girlfriend, an important but potentially distracting new stakeholder? Those close to him, including key members of the film crew, worried that his budding relationship would distract his vision, perhaps with life-altering and even life-ending consequences.

As one of Honnold’s filmmakers commented, “a romantic relationship inevitably takes away the armor, and he [needed] to be focused.” However, despite the potential concern, Honnold found his way to the level of focus he needed to accomplish his goal. When asked if having a girlfriend changed his mindset about risk-taking, he replied that he appreciated the concern, but “in no way [felt] obligated to maximize [his] lifetime.” And on June 3, 2017, the day Honnold became the first person to solo El Capitan, his girlfriend wasn’t there. She’d left hours before, opting to drive back to Nevada because she knew he needed his space. This need for separation, to remove people close to him from the risk, showed up earlier in the film when he cancelled an previous attempt at the climb in its first section. As is the case in bootstrapping, free soloing is often much less stressful when done in isolation. But it can also be lonely and the impact on those around the bootstrapper can be profound.

This team / climber separation was illuminated after the climb when Honnold was asked about his interactions with the team and whether it was clear they were concerned when he said:

“it was better for me not to think at all about anyone else’s experiences except for my own. I’m sure this [was] ultra-stressful for everybody else involved, but for me it was a big enough challenge to even walk to the base and put my shoes on. Because you look up and go, ‘that’s a [sic] big wall.’ It’s like, pretty crazy.”

Instead of leaning on others, he found his peace in the mountain, commenting that, by the time he reached the wall, “there was no uncertainty… [he] knew exactly what to do the whole way” and that “a lot of the handholds [felt] like old friends” due to his intense preparation and singlemindedness.

And so it is with the bootstrapping entrepreneur. While many have families and other people that they care deeply for, in most cases these entrepreneurs work to shelter their relationships from the stresses of the journey. As such, they must find their way to a stoicism that allows them to cope (in isolation) with the day-in-day-out risks of entrepreneurship without a safety net. Much like the perils of free soloing, the risks of bootstrapping carry a cumulative weight, which only grows as the impact of the associated risks affect the lives and happiness of other people. With more team members to support, families to feed, and customers to serve comes more responsibility; and, as was the case with Honnold’s El Capitan ascent, the risks grow as the elevation (size) increases, the founders age, their children grow up, and the business becomes more valuable.

In short, when a life well lived intersects with a business well built, the risks and associated overhang compound because there is so very much to lose. It is this dynamic that often leads a bootstrapper to start using safety gear (funding), to find a partner (financial or strategic), and to share the experience with others. It is why I have a job, and it is both rational (much more rational than the original bootstrapping itself) and intensely emotional at the same time when the deal closes…likely very similar to reaching the top of El Capitan without a rope and then realizing that the risks have grown too great to attempt the ascent again.

Even Honnold acknowledges that there is a reasonable chance his view will shift as additional lives intersect with his, saying

“I mean, we’ll see, we’ll see. Maybe if we have a family someday or something, maybe I’ll value it totally differently. Maybe I’ll never find another soloing objective that I’m as passionate about. Maybe I’ll never solo anything meaningful again. We’ll just see.

Alex Honnold holds all of his climbing gear atop the summit of El Capitan. He just became the first person to climb El Capitan without a rope. (National Geographic/Jimmy Chin)

The Mentality

Until the “someday” comes when life and risk and other priorities intersect in a way that make Honnold and other free soloing climbers seek a path to their zen with fewer risks, they continue to innovate, to push boundaries. Just like the free soloist, so too the bootstrapper continues on, building market-leading products, hiring employees, and executing with a similar ingenuity in the face of a category of risk and fear that most people will never know. This will be true while unicorns and heavily funded businesses execute technically but don’t feel the freedom, the beauty, and the perfection of entrepreneurship’s free solo: bootstrapping.
Regarding his particular talent, Honnold said “There are certainly better technical climbers than me. But if I have a particular gift, it’s a mental one – the ability to keep it together where others might freak out.” I count myself very lucky and incredibly grateful to work with people that could very easily say the same thing about how they build their businesses each and every day.

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