How to Be a Serial Entrepreneur: 9 Secrets to Success

By Jeff Solomon and Martin Luenendonk

Starting a business is no mean feat: Coming up with a profitable business idea is hard. Implementing a business idea and turning it into a successful business is even harder.

So it's understandable why, after building a stable business, most entrepreneurs put all their efforts and focus on ensuring the continued success of that business. They do everything they can to make sure the business does not fail, since this would force them to go through the challenges of building a new business all over again.

But there is another crop of entrepreneurs who seem to thrive on the risk and uncertainty of starting a new business from scratch. They are full of business ideas, and as soon as they implement one and turn it into a successful business, they are off to work on another idea—sometimes in a totally different industry. Such entrepreneurs are known as serial entrepreneurs.

Serial entrepreneurs enjoy solving different problems and the joy of seeing their ideas come to life. Once a business becomes successful, they either leave it under a capable manager and go off to start another, or sell it and focus on their next adventure.

Elon Musk: profile of a serial entrepreneur

One of the greatest examples of serial entrepreneurs is Elon Musk. He’s arguably the poster boy for serial entrepreneurs. Musk started his foray into entrepreneurship by founding Zip2 in 1995, which he sold four years later to Compaq for $307 million.

He then started X.com in 1999, which merged with Confinity in 2000, and then was renamed PayPal. In 2002 eBay bought PayPal for $1.5 billion. Musk invested all the money he had made from the sale into three new companies: SpaceX, Tesla, and SolarCity. From there, he also went on to found or co-found Neuralink, The Boring Company, OpenAI, and conceptualized Hyperloop.

Considering that even starting one business is a huge challenge, what is it about serial entrepreneurs like Musk that makes it possible to start not one, but several businesses, and make them successful?

Let’s investigate what serial entrepreneurs do that others don’t:

1. Serial entrepreneurs work with people and partners

Most serial entrepreneurs are highly aware of their limitations. Very often, serial entrepreneurs start businesses in a wide range of industries. For instance, Musk has started businesses in the fintech industry, automotive industry, space industry, and so on.

Naturally, it would be impossible for anyone to be highly knowledgeable in such a wide range of industries. However, serial entrepreneurs do not let this stop them. Instead, they work with other highly knowledgeable and skilled people to supplement their lack of knowledge and experience in certain areas.

If you look at most serial entrepreneurs, you will notice they did not start all their businesses alone. For instance, Musk co-founded Zip2, Tesla, SolarCity, Neuralink, and OpenAI with other entrepreneurs.

The same applies to many serial entrepreneurs: Andy Bechtolsheim (Sun Microsystems and Arista Networks), Neil Patel (Crazy Egg, Hello Bar, and KISSmetrics), Jack Dorsey (Twitter and Square), Dustin Moskovitz (Facebook and Asana) ... you name them. They didn’t build all their companies on their own. Instead, they found other skilled people who shared a similar vision and built companies with them.

Aside from partnering with others to create new companies, serial entrepreneurs also rely on other people to run and manage their businesses for them. Let’s face it: running the day-to-day operations of two or three companies can be very challenging, and serial entrepreneurs know this. Therefore, they don’t try to do it.

Instead, they put their focus into one business during the early stages, build it until it becomes successful, put systems in place to keep the business running, and then find a qualified manager to run the business for them while they move on to start another business.

2. Serial entrepreneurs take advantage of platforms and pay others

Running a business takes a lot of time and effort. To make things easier for them, serial entrepreneurs are masters at using systems and platforms to automate various tasks and reduce their workload. Aside from freeing up their time, relying on automation helps serial entrepreneurs reduce costs, improve operational efficiency, ensure quality and consistency, and improve governance and reliability.

Fortunately, the internet has provided entrepreneurs with hundreds of platforms they can use to automate various aspects of their businesses. For instance, if you are using social media marketing as part of your digital marketing strategies, there are dozens—if not hundreds—of social media marketing tools at your disposal.

Today, platforms exist that you can use to automate just about anything: customer service automation, lead generation, email marketing, report generation and distribution, content scheduling and posting, billing and invoicing, and so on. You can also use learning management systems to automate things such as employee onboarding.

Apart from using platforms, serial entrepreneurs are also very good at outsourcing tasks. For instance, let’s say you need to create content to market your business, but you don’t have the time to do it yourself, and you don’t want to hire a full-time content creator.

In such situations, most serial entrepreneurs will outsource such tasks to freelancers. Today, there are dozens of freelance work platforms where you can find freelancers to handle tasks like content creation, YouTube marketing, graphic design, creating a website, social media management, and so on.

Knowing when to outsource or automate tasks allows serial entrepreneurs to run multiple businesses simultaneously, without any of them getting neglected.

3. Serial entrepreneurs are visionaries

When traditional entrepreneurs start a business and make it successful, they put all their efforts into that one business. They focus on finding ways to keep the business profitable and stay ahead of the competition.

Serial entrepreneurs, on the other hand, are not satisfied with running one business. They are great visionaries who envision what the future can look like and create companies to build the kind of future they envision.

For instance, Musk started out by envisioning a world where people could transact money electronically, so he founded X.com. After selling the business, he then envisioned a world that didn’t have to rely so much on fossil fuels, so he started Tesla to build electric cars. In the same way, Musk envisioned a world where people will travel to space regularly, so he started SpaceX to build reusable rockets.

This is one of the most defining characteristics of serial entrepreneurs. They are always reimagining the future and looking for ways to make their dreams come true.

4. Serial entrepreneurs are not afraid of failure

Starting a business is a risky venture. There is no guarantee that a new business will succeed. Actually, about 90% of all startups fail, with 10% of them going belly up within their first year. This means that anyone who wants to start a business must be ready to fail. Actually, this is one of the major factors that keeps most people from starting businesses.

For serial entrepreneurs, this risk is multiplied several times. For every business they start, there is a chance it could fail. However, serial entrepreneurs do not let the fear of failure hold them back. They know it is part of the game, and many of them have actually failed several times.

Richard Branson, a renowned serial entrepreneur who owns multiple businesses under the Virgin Group, is no stranger to failure. Branson’s foray into entrepreneurship started when he dropped out of school to concentrate on his first business, Student Magazine. Unfortunately, the business did not make much money, and he eventually pivoted into music.

This was not Richard Branson’s only failure. He has had a string of several other failed businesses, including Virgin Cola, Virgin Cars, Virgin Brides, Virgin Digital, and so on. Yet, despite all these failures, Richard Branson has continued starting more and more businesses.

Branson aside, many other serial entrepreneurs have either failed or flirted with failure multiple times, yet they don’t allow this to hold them back. It is this persistence and refusal to quit, even after experiencing multiple failures, that makes it possible for serial entrepreneurs to start multiple successful businesses.

5. Serial entrepreneurs excel at time management

Good time management is one of the most important skills of a successful entrepreneur. Serial entrepreneurs, however, need to be even better at time management than the average entrepreneur.

Running multiple companies simultaneously means that a serial entrepreneur has to constantly attend meetings, come up with strategies to ensure the continued success of their companies, come up with new ideas, talk to investors and shareholders, and so on. It is impossible to do this without excellent time management, and more than a few productivity hacks to boot.

The poster boy of serial entrepreneurship once again provides a great example of what it means to be an excellent time manager. Musk has a strict daily schedule that he adheres to, with his schedule broken down into five minute slots.

He also maintains a strict weekly schedule. In a 2013 interview, Musk reported he spent Mondays working at SpaceX in Los Angeles; flew to the Bay Area to work at Tesla on Tuesdays and Wednesdays; was back at SpaceX on Thursdays and Fridays; and then spent his weekends either at Tesla or splitting the time between his two companies.

Without such time management, it would be impossible for Musk to run two very successful companies. Therefore, if you aspire to become a serial entrepreneur yourself, time management is one of the soft skills you need to develop.

6. Serial entrepreneurs adapt quickly

There’s a common saying in the army that no battle plan survives contact with the enemy. What this means is that regardless of how much you plan, things will never go exactly as you planned them out; regardless of how good your business plan is, there will always be some factors that you had not accounted for.

For serial entrepreneurs, the risk of things going wrong is higher, considering that serial entrepreneurs sometimes set up businesses in fields they have zero experience in. So, how do they still manage to build successful businesses in these fields?

It turns out, serial entrepreneurs are masters of adaptation. They know that in spite of all the planning they have done, business will always surprise you. Therefore, they are always ready to adapt and pivot through customer development and product iteration until they get it right.

For instance, when starting SpaceX, Musk’s plan was to build a greenhouse that would allow humans to grow food on Mars. He intended to use refurbished intercontinental ballistic missiles to transport his greenhouse equipment to Mars. After having trouble procuring refurbished missiles, Musk pivoted and decided to build his own reusable rockets.

This ability to quickly adapt and pivot in the face of challenges and obstacles plays a huge role in helping serial entrepreneurs build successful businesses.

7. Money is not their only focus

A lot of people start businesses because they want to make money and retire rich. For serial entrepreneurs, however, money is not their main focus. The focus of serial entrepreneurs is only coming up with solutions to challenging problems.

To understand serial entrepreneurs’ love/hate relationship with money, think about this: what would you do if you had $180 million right now?

Some would retire and spend the rest of their time sunbathing on some tropical beach. Others would buy a house or something else they’ve always wanted. At the very least, most people would invest the money in something with the least amount of risk to avoid losing the money.

But what would a serial entrepreneur do? After selling PayPal to eBay, Musk made about $180 million. However, he did not move to a tropical beach town or put the money in a low risk investment. Instead, he put all the money into his two new startup companies: SpaceX and Tesla. At one point, he almost went bankrupt.

Luckily, both companies pulled through and helped him build a massive fortune. At some point, he even became the richest person in the world, although just briefly.

This is part of what makes serial entrepreneurs so successful. They do not focus on the money. Instead, they are totally focused on building the next big thing.

8. Serial entrepreneurs don't get caught up in analysis paralysis

Before starting a new business, most people will spend a lot of time learning, planning, doing market research, building a sales process, and so on. While being prepared is good, the problem is a lot of people get caught up in analysis paralysis. They wait until they have all the information, but unfortunately, this means they never get to start.

According to Jack Dorsey, a serial entrepreneur who has cofounded both Square and Twitter, the actual learning happens once someone gets in the game. This is something that is echoed by most other serial entrepreneurs.

Serial entrepreneurs don’t sit and wait for the perfect moment, or until they have learned everything they need to know. Instead, once they have adequate information, they jump in the ring and start building their businesses.

Once they have built something tangible, it then becomes easier for them to learn what is working and what is not, what the customers want, and so on.

Serial entrepreneurs also don’t get other people involved until they have something tangible. They don’t talk to potential customers or investors until they have a minimum viable product or have found product-market fit. They understand that no one will invest in an idea that is only in their minds.

Similarly, if you want to achieve success like a serial entrepreneur, you should focus on getting started today. Start writing the code for that app you want to build, start building that website, start developing a minimum viable version of your product.

9. Serial entrepreneurs are constantly looking for new opportunities

Entrepreneurship is born out the ability to quickly spot and take advantage of opportunities. However, while the ordinary entrepreneur only looks at opportunities within their industry, serial entrepreneurs are constantly looking for opportunities in all possible industries and sectors.

Serial entrepreneurs try to understand every industry and sector they come into contact with, and quickly try to identify problems in these sectors that they can solve. In other words, they are always looking for a problem to solve, even if it is in an industry they know nothing about.

At the same time, however, they also put a lot of focus into learning. They don’t just go into new industries blindly. Instead, they quickly teach themselves everything they can about an industry before getting into it.

Are you ready to start a second business?

Starting a business is a difficult undertaking, and once they find success with one business, most entrepreneurs put all their focus into that business. Serial entrepreneurs, on the other hand, enjoy the challenges of building a business from the ground up, and are on a constant search for the next business opportunity.

What is it that serial entrepreneurs have that gives them the ability to start one successful business after the other? In this article, we have shared nine key things that serial entrepreneurs do differently, allowing them to start successful businesses in multiple industries.

If you are a one-time entrepreneur who is considering taking a leap to start your second business, we hope these tips will provide some guidance and increase your chances of achieving success with your new business venture.

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