7 Serial Entrepreneur Superpowers Revealed By My Guests

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One thing that has always struck me as odd is the label serial entrepreneur. To some, it means that they do company after company serially. Still, other entrepreneurs will say they are serial but really are parallel entrepreneurs, which is a fancy way of saying doing multiple businesses at once.

I was curious as to what my serial entrepreneur guests on The Entrepreneur Ethos podcast had to say about it. In particular, what superpowers have they developed to handle launching (and sometimes running) multiple businesses?

While not everyone that I have interviewed called themselves either serial or parallel entrepreneurs, all caught the entrepreneur bug and now make it their career to create and launch businesses -- a category in which I also fall into.

Using Machine Learning to Make My Life Easier

To compile the 7 Serial Entreprneuer Superpowers, I did something I often do -- use machine learning to help sort through all the interviews. This method has proven to be a huge timesaver and I’m looking forward to doing it a lot more. Not only because it’s more efficient but it also ensures that I don’t miss anything. I’m also kinda a nerd at heart and love learning things like how to do topic analysis using Amazon Comprehend.

These superpowers are in no particular order or anything like that. So now, let’s explore the 7 Serial Entrepreneur Superpowers Revealed by my Guests.

After each one, I’ll also recommend what I think is the best episode of the podcast to listen to that showcases the superpower along with a book that I found a good resource to learn about the superpower.

#1 Practice People Development

People make or break a company. It seems obvious but the main job of the CEO of a startup is to ensure that their people have what they need to get the job done. This includes developing said people to take on greater and greater responsibility.

This recurring theme among my serial entrepreneur guests is how they create teams of teams that will be ready when the next big idea comes along. The best way to develop people seems to boil down to being a coach.

I have interviewed several entrepreneur coaches as well as regular entrepreneurs who value developing their people. The best episode to listen to regarding people development is episode 74 with Trav on how to live a meaningful life.

The best book I have found for this coaching mindset is The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stainer.

#2 Adhere to a Set of Principles and Values

They say that knowledge is power but I feel that the ability to acquire knowledge is even more powerful. When I ask my guests about how they build their companies, it usually centers around some foundational principles. These founding principles vary from person to person but it’s pretty consistent that serial entrepreneurs have learned a sort of first principles approach to life.

These principles tend to be broad to allow a wide berth of actions to take place. It’s kinda like guardrails so to speak. If you’re outside your guardrails then it’s time to take action. Principles and their cousin, values, allows an organization to be nimble enough to handle change yet constrained enough to not go down a rabbit hole.

All of my guests live by some set of principles and values. So it’s tough to pick a single episode that exemplifies this. The one to start with would be episode 67 with Brandon and our discussion about Message over Fear.

The best book I have found for this principles approach is well, Principles by Ray Dalio.

#3 Know When to Walk Away

Walking away from an idea is hard to do. I mean really hard to do. Most of my guests have struggled to shut down a business or kill an idea. I’m guilty of this as well. I tend to always want an idea to work out but deep down, I know that some, well most, won’t.

By their nature, serial entrepreneurs have lots and lots of ideas. They learn, over time, when to invest and when to walk away. This is also important when an idea takes off and you reach your level of incompetence. This can also be a struggle yet my serial entrepreneur guests are always trying to find that balance.

The episode that talks about this the best is Episode 22 with Richard when we talk about lots of small projects.

The best book I have found on knowing when to walk away is The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz.

#4 Be the First to Believe

One not-so-obvious superpower that the serial entrepreneurs I have interviewed have is that they see the potential of a half-backed, this will never work, kind of idea. Call it optimism or some sort of magical alchemy but it’s clear that all of them were the first to believe in an idea.

This insane optimism seems to be rooted in having a principle and value of knowing that lots and lots of innovations that are obvious now were not so obvious at the time. For me, I always say when I help entrepreneurs, that I’ll be the first to believe and the rest will be up to you.

The best episode for this one would be episode 32 with Dilip where he talks about his Lucky Vision and how it’s hard to be a believer when no one gets it.

The best book I have found on this idea of believing in the power of innovation is Loonshots: How to Nurture the Crazy Ideas That Win Wars, Cure Diseases, and Transform Industries by Safi Bahcall.

#5 Be Insanely Curious

Building on being the first to believe is being insanely curious about the world. It’s this curiosity that drives so many whacky and crazy ideas that just might work. Curiosity for the serial entrepreneurs I have interviewed seems to know no bounds.

Some of the best ideas that my guests have come up with have been when they were learning about a totally different industry or applying technology from one industry to another one. It’s these cross-over ideas, like what’s going on in Digital Health, that drive a ton of great ideas.

The best one to listen to for this one would be when Ravi and I discussed Sutro in episode 2 and how he invented it.

The best book I have found on this idea of being insanely curious is Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life by Rory Sutherland

I’m a big believer in if you battle the dragons and return with the gold, you should share what you have learned. Lots of my guests have a similar attitude and it’s the main reason they come on the podcast.

All the episodes demonstrate this so I’ll leave it to you to pick your favorite. If you want a recommendation, I’d listen to episode 49 with Nate when we talk about taking charge of your success or the episode with Joanna where we talk about not being afraid to fail and how she writes so many books to share her knowledge. One of which inspired this bonus episode as well.

In terms of a book on this, that’s a tough one. I think that the best example of someone sharing what they learned is The Boron Letters by Gary C. Halbert. It’s a series of letters to his son Bond about how to write copy. It’s one of the best books on the subject and is also a great example of sharing what you know. Of course, shameless plug here, you can also read my book, The Entrepreneur Ethos, which is the basis for this podcast.

#7 Avoid Time Vampires

Time is our most valuable resource. As the saying goes, you can print money but not time. Since time is valuable, giving our time to others is an act of goodwill and shows that we care. This is especially important for serial entrepreneurs because you never know where the next deal or idea will come from.

Of course, there are limits to this. One cannot give away all their time since then nothing gets done. The way to protect your time is to set aside a certain amount of it to give away. The importance of balance on this cannot be understated.

It’s through meeting and talking with others that we can get feedback on our ideas and generate new ones. This is the main reason I do this podcast.

Time vampires also include busy work and non-value added activities that are more procrastination than actual work. The trap is the time vampires that take and take and take but give nothing back. We all know them (both the people and the tasks) and the best serial entrepreneurs avoid them at all costs.

The best episode for understand time is episode 5 with Mark S. when we talk about now is the time to start a business. Mark’s a productivity coach (Mr. Productivity to be exact) and he is a master at this.

The book I would recommend is Getting Things Done: The Art of Stress-Free Productivity by David Allen.

Enjoy the Journey

One last thought on serial entrepreneur superpowers. Everyone I have talked to about their entrepreneur journey tells me that it’s the joy of building and creating something from nothing that keeps them coming back to do company after company. Enjoying the journey I think that’s the ultimate superpower.