A Bootstrapped Founder's Leadership Manifesto

As Explorance fast approaches its 18th anniversary as a bootstrapped company, I find myself reminiscing about the journey that has set us on the growth path from $0 to $50M, and reflecting on the path forward that will bring us from $50M to $1B.

I have never truly aspired for Explorance a tangible outcome, such as a revenue target. To me, the above-stated target of $50M to $1B is much more intangible than it is tangible. It is simply a statement of mission.

What it really means is that we need to transform the way we do things to reach out goals. We have grown accustomed to bringing solid growth performance through a pure bootstrapping mindset that relied on a clearly differentiated culture, a collective sense of purpose, and much individual heroism.

It brings me much pride how far we have gone with very little. With a mere $55K invested in Explorance back in 2003, and to date with zero institutional backing or funding, we have become the global organization that brings together 300 mighty Explorers serving the needs of close to 1,000 organizations globally, including 35% of the Fortune 100, and 1 in 4 of the top higher education institutions out there. More importantly, I feel great about what we do, how we do it, and who we do it for, when I am reminded everyday how Explorance touches the lives of more than 20 million lifelong learners.

What got us here, alone, won't get us there!

To get to that next level, I am now convinced that we must fast augment our bootstrapped ways with a by-design scale-up mindset. That will necessitate me to be surrounded with best-in-class leaders. If life at Explorance has taught me something over the last few years is that all it takes for a team to fail is one, and only one, weak link.

Lessons Learned in Leadership, or Lack Thereof

I have an inching feeling that the following lessons would not come as a surprise to many. Alas, to me, this has been the fruit of many years of learning, experimentation and reflection upon past mistakes, hardships, challenges, and successes.

At the heart of leadership success is the notion of total-trust. The kind of trust that people experience when they go into lifelong relationships. Nobody goes into a serious relationship in life, without trust. In doubt, or foundational disagreements, seldom a relationship can thrive, or let alone survive. Trust is simply a choice that the most audacious of us can pay forward. It is a choice we make as we keep moving forward.

So first and foremost, we should appoint leaders that we can so-easily choose to trust. But more importantly, we must ensure that these leaders are also willing, and able, to choose to trust the approach and direction of the organization they join.

Strategy without Execution is USELESS

This is so true of a growing bootstrapped organization that brings in big names, or people with big experiences, into their organization as leaders hoping they will bring the miracle cure along with them.

In my experience, these leaders typically come with a lot of great ideas and aspirations, and they seldom take the time, or show the necessary humility, to understand well what makes that bootstrapped organization they just joined tick. Many of them are possibly so imprinted with their previous successes that they end up trying to fit in their new home as a square peg in a round hole. If success was a recipe that is so easy to replicate from organization to another, then why aren't all equally as successful?

Such leaders are typically not accustomed to the younger organization, no matter how exciting and mature it seems. It typically hides many imperfections and lacks the support structure typically available to leaders that succeeded elsewhere to lead from above.

Execution without Strategy is RECKLESS

The danger of execution without strategy on a young organization is severe, and may sometime cause irreversible damage. At Explorance, I experienced this trait early-on when we brought in people that rode a massive wave of success in previous careers that brought them way too fast to the top, mostly depriving them from the opportunity of suffering and hustling their way up. Such leaders think they got it all figured out, but the reality is that they come without a plan, or a clear way to getting somewhere.

I have witnessed first hand leaders that could not even produce a 12 months forward-looking plan, let alone a first-hundred-days plan. The associated danger with such leaders is that they could further accentuate the weaknesses of less organized bootstrapped organizations, and many times they would end up demoralizing and disengaging their own reporting employees that were hoping for guidance, support, and an elevated experience.

When a leader is really strong on execution, while lacking in strategy, just imagine how far they would go in the wrong direction before they realize it, or before they are stopped.

Strategy and Execution, without Empathy is DANGEROUS

There is no need to dwell on this much, because history has indeed provided extremely compelling leaders that were highly competent in both Strategy and Execution, but because they lacked in empathy, they ended up causing severe mayhem on civilization.

Joining a bootstrapped company requires any externally sourced leader to be highly empathetic. They are typically joining a place that has a real strong and highly differentiated culture. That organization is most possibly full of superheroes, and in many cases many misfits. It is the coming-together of people that have something to prove that creates successful startups. It takes a village. And at the beginnings, that village has to be full of people that can compensate for lack of process, lack of resources, lack of funds, lack of leadership with pure and sheer motivation, strength and sacrifice.

So empathy is key to balance a bootstrapped organization's aspiration for scaling-up, with the sheer force that its employees can still bring to the table towards making it mightier than any established giant.

It is always better to understand a starting point, and the lay of the land, before one can successfully execute on strategy.

But without Balance, one can NEVER BE A TRUE LEADER

This observation may be unique to my perception, but I doubt it. Have you ever looked at the Forbes list of billionaires and not felt impressed at all? I often find myself experiencing distaste when I look at that list. That is because, in most cases, these leaders have let the ends justify their own means. Hence, chances are that many have let down an aspect of their life, be it family, friends, health, integrity, or community.

Balance is about effective juggling of priorities. The lines between work and personal life are usually blurred for most leaders. As long as that fragile balance keeps them whole, and keeps their loved ones, and those communities they serve, supportive and patient with them. Only then, can greatness can be achieved.

These traits that make, in my opinion, for a great leader are not a shopping list where one can pick from. These are integral attributes to leadership success that, in most cases, are hard earned in life.

They are typical of the gritty ones that have worked really, really hard and diligently throughout their career. The latter typically shows a long and consistent path to the top, where they have succeeded at every step of their personal and professional journey of growth, influence, and evolution.

I dream of a day, soon, when I am only surrounded by such leaders. And maybe, if not too much to ask, they are also interesting, caring, audacious, out-of-the-box thinkers, and fun as hell to be around.

This is what Explorance, our customers and Explorers, and I, need to get to the next level.