What Is a Serial Entrepreneur & How To Run Multiple Ventures

This entrepreneurial journey is tough and rocky, and often longer than anticipated. The key to mastering this journey is adopting the right mindset, where we can discover vast untapped reserves of persistence, grit, and intelligence.

This is especially true for serial entrepreneurship, where your routines, methods, and ideas must work in perfect unison to cater to a series of enterprises.

People like Elon Musk have already discovered the right mindset unleashing a portfolio of incredible startups, with his eyes currently set on the horizons of another planet.

Have you struggled to develop your mindset for entrepreneurship? Have you ever wondered how entrepreneurs can create one successful startup after the next?

Here is a breakdown of crucial mindset adjustments you can effectively leverage along your journey towards serial entrepreneurship.

What is Serial Entrepreneurship?

Serial entrepreneurship is the activity of founding multiple businesses and successfully running them. Serial entrepreneurs use the momentum of their initial success and recycle it into a chain of startups.

Running multiple enterprises may seem science-fiction at a superficial glance. But at the heart of the serial entrepreneur journey lies a rock-solid foundation of mindsets that anyone can adopt and use effectively.

The following core mindsets can give you a boost at any stage of your entrepreneurial journey but are key when it comes to running multiple ventures.

How to Run Multiple Business Ventures

1. Divide and Conquer Your Ventures

Elon Musk’s entrepreneurial accomplishments can seem superhuman or magical to many. In the aggregate, it certainly is. However, if you break down each accomplishment into smaller and smaller steps, at the very core, you will find tiny bits of actionable, doable tasks. Only in the aggregate does it seem super-human.

Here’s a wild analogy: Have you ever watched breakdancers perform at the RedBull BC One competition? The incredible athletic performances seem nothing short of super-human. Words simply don’t serve justice to the athletic performances of these athletes, so it’s best to give it a quick view.

Each performance is a giant mix of specific power moves – flares, air-flares, windmills, and air-chairs, to name a few – each has a step-by-step guide to mastering the move.

With the right mindset, discipline, and genetic luck, one can conquer move by move to create a true breakdancing work of art. You can apply this analogy to practically any stage of your entrepreneurial journey, whether you are solving complex problems within a single entrepreneurial endeavor or managing the complexities of multiple startups.

Using the Divide and Conquer engineering approach allows one to better understand what it takes to solve problems as the smaller, doable tasks are easier for the mind to process.

This tactic is a game changer for serial entrepreneurs. It allows them to tackle big problems with confidence as they understand what looks scary is just hard work.

2. Failing Into Serial Entrepreneurship

Serial entrepreneurs hold an impressive portfolio of successful ventures. However, focusing solely on the successes can distract one from the most valuable moments in their successful journey, the failures. Certainly, we should use our intelligence and intuition to avoid misfortune where we can, however, and paradoxically so, we should embrace moments of failure with great care and attention.

Jewish philosophy states that pain invites wisdom that one cannot achieve otherwise, and this is certainly true.

“Pain and suffering are opportunities to challenge the way we look at life. When things are going well, we tend to take life for granted, but trauma brings us to the edges of life, allowing us to view it from a new, revealing angle.”

In the bizarre world of entrepreneurship, this is exceptionally true. The relationship between success and failure is not mutually exclusive but beautifully symbiotic. Your wins will bring you to new horizons where the failure of some sort is a statistical certainty. And your failures will serve as a time for introspection and growth in preparation for that next right moment. When it arrives, you can leverage that newfound growth to take you to heights that were impossible prior.

Failure forces us to do what we naturally avoid, which leads us to introspection, reflection, and becoming wiser for the next opportunity that awaits. Those who shy away from introspection and don’t harness the incredible power of failure sever their ability to see beyond their current horizons.

In the world of entrepreneurship, the prospect of failure comes with the territory. It is estimated that over half of new businesses fail in the first five years, and two out of three last less than a decade. The aim here should be to keep failures short and sweet, and mitigate long-term damage. When they do happen, it’s important to craft the perfect balance between swimming in the pain and knowing when it’s time to look forward.

Elon Musk is an example of someone who shows incredible resilience in the face of failure. He had exhausted all of his capital after three failed attempts at launching a reusable rocket at Space X. His company was done, and no one wanted a part of it. Musk had to use the money he earned from selling PayPal to fund his own and final 4th launch. It’s either launched successfully, or he’s moving back to his friend’s couch.

In an interview with 60 Minutes, Musk was asked,“When you had that third failure in a row, did you think it was time to pack this in [close Space X],” to which the teary-eyed entrepreneur replied,

“I don’t ever give up, I’d have to be dead or incapacitated.”

Under the immense pressure of three failed launches, investors, family, and close friends, Musk was told to cut his losses and give up. Instead, Musk didn’t let failure hold him back from his dreams. Today, Musk is the richest man in America, with a net worth of $208 Billion.

3. Across-the-Board Problem Solving

Serial entrepreneurs operate at a very precipitous efficiency, and getting bogged down in one area can make their entire workload unsustainable.

Akin to a college student picking courses for his upcoming semester. His course load is fully manageable until he takes on one course too many. After which, every course becomes exponentially more stressful.

Serial entrepreneurs remain effective by having incredible problem-solving skills or, more importantly, being able to foresee a collision ahead and avoid it altogether. They constantly test new problem-solving models, optimize what works and throw away what doesn’t. One such method for problem-solving is known as “double-loop learning.”

During the Iraq war, the US military reported a significant and unexplainable increase in eye injuries. Lead surgeons proposed more innovative forms of eye surgery and even new protocols to reduce the risk of long-term eye damage.

Dr. Atul Gawande, an American surgeon, writer, and medical researcher identified an emerging pattern and asked a slightly different question, “why are there so many eye injuries when they are supplied with protective gear?”. It was soon discovered that the goggles were slightly uncomfortable to wear and “didn’t look cool.” They then contracted a designer to make Star Wars-like goggles that felt good and looked amazing. From that point forward, the number of eye injuries nose-dived.

4. Single and Double-Loop Learning

This would entail finding creative ways to respond to the issue after that fact, focusing one’s energy in a more reactive manner. Though you solve the issue at hand, it’s comparable to bringing a jackhammer to a surgery room.

Dr. Atul Gawande recognized an underlying pattern and solved the root cause of a continual problem. This was a proactive approach to solving the issue.

Serial entrepreneurs leverage such problem-solving skills at every twist and turn of their job. Whether it be demonstrating leadership with a project manager when there is a repeated cycle of frustrated clients. Instead of spending repeated energy doing damage control, you identify emerging patterns and revise internal communication protocols so that such issues don’t arise in the first place. Or recognizing patterns of behavioral traits in clients that tend to drain company resources and steer clear of potential stress points in the company.

Final Thoughts

Entrepreneurs serve as the backbone of human ingenuity, channeling their ideas into game-changing inventions. Serial entrepreneurs take it to the next level by leveraging core entrepreneurial mindsets to take humanity to new heights. It’s easy to look at Elon Musk’s array of successful endeavors and feel he is superhuman. The truth is, the illusion of the whole can be broken down into smaller actionable steps, and with the right mindset, you too can take humanity to incredible new heights.

Featured photo credit: Humphrey Muleba via unsplash.com