Hey there! My name is René and I consider myself a Serial Entrepreneur as I’ve founded not one business, but seven businesses. In 2003, my first business was a Digital Agency, my second was an Artificial Intelligence Start-Up, my third venture was co-founding a traditional consultancy firm, then my next 3 businesses were created at the same time (I learned how to juggle): an Analytics Consultancy, a Social Media Consultancy, and a Privacy, and Data Protection Legal Boutique Firm. Now after having reflected on different ideas and projects I’ve decided to start a new project, my number 7th (lucky number), where you are right now. But enough about me and let’s get into the subject.
When thinking about famous serial entrepreneurs individuals, people think of names like Richard Branson with his Virgin brands, Elon Musk with Paypal, Zip2, Tesla, SpaceX, or even Oprah Winfrey with Harpo or Oprah Winfrey Network. But these are exceptional one-in-a-million entrepreneurs, their net worth is astronomical, and they are not the typical entrepreneur. At least, they are not my serial entrepreneur examples to follow even if they have valuable learning to be gathered from them.
Throughout my career, I’ve come across multiple serial entrepreneurs that don’t make the front page of Time magazine, they are also successful serial entrepreneurs, exceptional, and worth studying. I think of them when I write this blog post.
I’m passionate about entrepreneurship, so it felt logical to start this blog by sharing with you what I’ve learned down the road in the matter, and what I’ve taken from many Serial Entrepreneurs that I’ve had the honor of meeting during these past 27 years. This doesn’t come from the biographies of Sir Richard Branson, Elon Musk, or Steve Jobs, but from more ‘normal’ serial entrepreneurs, if I may say so. So let’s dive in and reflect upon what is and makes a serial entrepreneur and what are his characteristics. You’ll see, that they are more than just successful entrepreneurs. I hope you’ll enjoy the ride and who knows maybe in no time you’ll discover that you’re a serial entrepreneur yourselfr.
The Calling of the Serial Entrepreneur
What drives someone to start new ventures, company after company, immersed in the thrills and spills of entrepreneurship? Serial entrepreneurs are a special breed – we feel an insatiable itch to start new businesses from the ground up based on our new ideas. These innovative spirits thrive on starting multiple ventures, wearing multiple hats, taking high risks, and creating novel solutions.
For us, it’s never just about profit (although that’s nice too!). It’s about the passion of bringing our visions to life, of starting a new business. Serial entrepreneurs we get an adrenaline rush from identifying problems begging to be solved and then doing whatever it takes to address them. We firmly believe we have the skills and drive needed to leave our mark on the world. For example I always feel great pride when I see how my first employees have evolved.
Of course, this intoxicating career path is certainly not for everyone. It requires tremendous commitment, discomfort with uncertainty, and the will to repeatedly pick yourself up after falling flat on your face. But for those called to answer, it can be immensely worthwhile. I can’t count the number of days when I woke up and went directly to the toilets to throw-up. Yes, I’m going to be very transparent in this new blog and share the good, the bad and the ugly. If you’re looking for a ‘everything is easy, everybody is nice’ kind of content, this site is not for you.
Cultivating the Entrepreneurial Mindset
At its core, being a serial entrepreneur demands a particular mindset. This entails cultivating certain habits of thought that prime you for pursuing original ideas:
Curiosity
Serial entrepreneurs are insatiably curious, always on the lookout, constantly wondering “What if?” and “Why not?” about products, business models, unique ideas, and customer pain points. I have ideas every week, sometimes everyday. I write many of them in a special notebook that I have. I remember 5 years ago, I lost my ideas notebook. I felt like I had lost 100k, I made everything possible to find it, but no luck.
Creative Problem-Solving
They flex their mental muscles to come up with inventive solutions, mashing disparate concepts into something novel. Constraints and difficulties are viewed as design challenges rather than dead ends. You need to train your mind in thinking out of the box. Try merging ideas from different industries together, think of ideal future tools even if they are impossible right now. It will train your brain.
Risk-Taking
Veterans of entrepreneurship are friends with uncertainty. These types of entrepreneurs often have a high risk tolerance. They regularly take leaps of faith in untested assumptions in their quest to create value sometimes based on a single idea. I like to say that taking risks is not risky.
Resilience
When business ventures crash and burn (and they will, trust me, I’ve been there), serial entrepreneurs tap into mental toughness to pick up the pieces and move forward. Failures become data points for improvement. This is a concept that I love and that I started to use as value of my companies in 2001 when I was co-founding a Consultancy firm. I remember that back then, in Spain I needed to explain the concept as it wasn’t main street as it is today. And Resilience is still part of my values as you can see in the about section of this site.
Adaptability
In a landscape of constant change, they roll with the punches. Pivoting is seen as progress when circumstances demand flexibility. Another way to look at it is being able to adapt to change. As I like to say I’ve changed schools over half a dozen times and since I was born I’ve changed houses over three dozen times. This has built my capacity to accept and embrace change. So try to do things that will cultivate your ability to adapt to changes. Don’t take always the same route back home, don’t go always to the same restaurants and sit down at the same table, read different newspapers, you get where I’m going right?
This entrepreneurial mindset develops over time through concerted effort. But making its cultivation a priority will prime you for success.
Play to Your Strengths for Business Success
A Serial Entrepreneur must identify his native talents, skills, and experiences that make him uniquely positioned to recognize certain opportunities. Maybe he’s a stellar marketer who spots customer acquisition gaps and has a great understanding of the market. Perhaps his finance background equips him to streamline small business budgeting across multiple industries. Or his photography hobby allows him to envision innovative ways of capturing images. Look into what you love, know and enjoy. You might find out your next eureka idea.
A serial entrepreneur might start cataloging everything he’s naturally good at and then deploy those strengths for his venture ideas. This ensures building businesses on a solid foundation of competitive advantages rather than just chasing shiny objects. It’s absolutely thrilling to create companies within your circles of competence and sometimes even multiple ventures simultaneously.
Entrepreneurship Opportunity Knocks…Listen!
Good serial entrepreneurs always have their antennas up to detect promising opportunities in their environments for their next new business ideas, always thinking about what’s next. They make a habit of engaging with people from diverse backgrounds, reading voraciously, and analyzing trends to stimulate their thinking.
When we notice customers struggling with an experience, marketers dropping the ball, or emerging technologies opening new possibilities, we pounce. Opportunities excite the serial entrepreneur’s imagination about how we could uniquely solve problems or fill needs better than the status quo. It reminds me when I was a child and someone offered me a set of Lego. I couldn’t wait to tear the box apart and start building, it was a new opportunity to build something new.
So be on the lookout for opportunities by embedding yourself into relevant communities, talking to target users, and studying market gaps and pain points. Listen closely so you can catch that entrepreneurial lightning in a bottle.
Extracting Value from Failure
Brace yourself: Failure is inevitable in entrepreneurship. No matter how strategic you are, ventures will falter thanks to faulty assumptions, poor execution, or plain old bad luck. It hurts when something you poured your blood, sweat and tears into doesn’t pan out. And it happens more than you think. Don’t forget that almost half of the companies fail in their first 5 years and if we look at the startups specifically that percentage skyrockets.
But the serial entrepreneur is someone that realizes failure provides an invaluable education. Use it as a teacher rather than letting it crush your confidence. If it happens to you, even as a traditional entrepreneur, ask yourself and make sure to write it down somewhere:
- What crucial lessons did this teach me about bringing a product to market, leading teams, or securing funding?
- How can I use data and feedback from this experience to improve my next venture?
- What assumptions did I make that proved wrong?
- How did my strengths and weaknesses contribute to what transpired?
By mining your failures for insights, you can strengthen your overall approach to entrepreneurship. Loss leads to growth when you extract wisdom from the wreckage. Then if the failure for instance made your business go away, you take the learnings and you move on to another venture.
The Power of a Supportive Community
Attempting to build a business solo is a recipe for burnout and isolation. That’s why constructing a web of support, mentorship and accountability is critical for serial entrepreneurs (and non-serial entrepreneurs).
Identify potential mentors who can advise you based on their entrepreneurial wins and misses, preferably people who have been business owners. Recruit fellow founders who face similar challenges to exchange war stories and problem-solve together, who knows maybe you’ll end up doing a venture together or founding an entrepreneurs club. Pitch friends and family on being your cheerleaders through the ups and downs, but make sure they are going to be positive. I’ve gone through cases where either envy or misunderstanding made people around me saboteurs of my ventures. And don’t neglect to build strong professional relationships that could yield future partnerships down the road and open new doors.
It also helps to find colleagues with skills complementary to yours rather than just carbon copies, don’t be troubled by being a co-founder of your next venture. For example, pair technical chops with business savvy, or couple marketing flair with operations experience. Diversity of thought and ability on your team is a competitive advantage. With the input and support of your community, you’re far less likely to fly blind. And you’ll have others to lean on when tough times undoubtedly hit.
Serial Entrepreneurship: The Agility to Pivot
For an entrepreneur, change is the only constant. Remember what I said earlier about my experiences changing schools and homes? So serial entrepreneurs prioritize agility and learning to adapt quickly. Rather than rigidly sticking to your original idea no matter what, stay open to input that challenges your assumptions. The objective is building a successful business, not being right.
If customer feedback indicates your proposed solution is off-base, be willing to go back to the drawing board. Watch for emerging technologies and market shifts that could disrupt your strategy. And if data suggests your business model needs to evolve, don’t cling to what’s not working.
Serial entrepreneurs are comfortable with course correcting because they fix their focus on the end goal, not necessarily how they get there. Remember, the important thing is your WHY, not your how. Remaining nimble allows you to iteratively improve and align yourself with realities on the ground.
Become a Serial Entrepreneur: Fuel Your Fire
Lastly, don’t ever lose sight of the passion that compels you to create something from nothing over and over. The serial entrepreneur’s path is too demanding and risky if you’re only chasing paydays. Your internal fire and sense of purpose must fuel your efforts in order to run multiple businesses.
So check in regularly with yourself: Does solving this particular problem make you leap out of bed each morning or do you feel you are in a boring company? Are you thrilled at the prospect of serving these customers with this new solution? Is this venture an expression of your talents and values? Aligning your companies tightly to your passions exponentially magnifies your motivation when challenges arise.
Embarking on the Adventure of Multiple Businesses – A Conclusion
Well, those are all the tips and reflections I have based on my serial entrepreneurship experience and knowledge from other fellow serial entrepreneurs that I’ve met over the years. If it’s something that tempts you, please be my guest, there are millions of entrepreneurs out there in the world and I’m sure that there are plenty of them willing to become a serial entrepreneur.
Don’t forget that a serial entrepreneur is an individual, not a superhero. He is someone who starts with a single business before starting another. So be always on the lookout for new business opportunities, keep moving, and write down every time you are coming up with new ideas, you never know where you’ll find business success or if you will end up managing multiple businesses.
In the end, you’ll learn that the journey is as important as the destination. As a Serial Entrepreneur friend of mine told me: when he sold his first company he went to live to the Bahamas, and when I asked him why he started again a new venture and left the Bahamas he replied “There are so many Margaritas you can drink in one day…“.
In summary, by cultivating an entrepreneurial mindset, playing to your strengths, remaining alert to opportunities, learning from failures quickly, building a support network, staying agile, and connecting to your purpose, you can navigate the winding road to serial entrepreneur success. Hopefully these insights illuminate some signposts that can guide your entrepreneurial adventure. Wishing you fulfillment and prosperity as you bring your visions to life!
Please don’t hesitate to share your key takeaways, your comments or questions. I read them all!
