The Partying Polymath Who Hustled His Way to Success

The Partying Polymath Who Hustled His Way to Success

Shaun Gold is the true definition of a polymath. 

He is a lifelong entrepreneur, 2x best-selling author, and international speaker. 

He is also a consultant and super-connector to startups and standouts, a screenwriter, and a former contestant on Jeopardy.

Shaun advises CEOs, entrepreneurs, executives, and founders of startups who are pursuing their own definition of success.

We reached out to Shaun to discuss his unorthodox entry into entrepreneurship, why founder conformity is detrimental, and how he helps startup founders realize their potential.

Q&A with Shaun Gold

You call yourself a living polymath. What does that mean? 

It means someone with a wide range of experience, skills, and most importantly, curiosity. I refuse to let the opinions of others or even the opinions of society mold me into someone else.

I followed my interests and did not specialize in one area. Instead, I worked in a variety of verticals. The vast amount of knowledge I gained allowed me to accomplish what others would deem impossible.

You majored in entrepreneurship at the University of Miami, but lectures don’t teach you everything. What’s one important lesson you learned in your studies and one thing you wished college had taught about entrepreneurship?

One quote that I recall from university is that “it’s better to own 60% of something than 100% of nothing.”

My entrepreneurship professor hammered that into us, especially as we were a bunch of students who thought we were capable of deal-making and fundraising (which we weren’t).

I wish they focused more on how to endure the inevitable periods of suffering and inactivity that come with being an entrepreneur.

Can you explain how suffering and inactivity are ‘inevitable’ in entrepreneurship?

Sure. No matter how hard you work, you are always at the mercy of others. You will have to deal with long stretches of time where nothing happens.

Investors will take their time to get back to you, customers may not flock to your offering, strategic partners won’t commit, and so on.

You are left with nothing to do but wait.

And this is painful.

You want to be successful overnight but the phrase ‘it takes fifteen years to become an overnight success” is true.  Being able to endure the process, to keep going when the emails are silent and the bank account continues to dwindle, is something that all entrepreneurs must face.

Yet, we are all surprised by this. No one told us that we would have to endure, but endure we must. We must press ahead; working, experimenting, and never backing down, ultimately emerging victorious.

You became the ‘chief distraction officer’ at a university renowned for its parties and crazy diversions. How did you end up starting ‘Nightlife Ninja’ and making a living from throwing parties?

I had a desire to get into the nightlife scene when I was 17 so I chose the University of Miami (over a far superior university) simply for its proximity to the nightlife.

It was the riskiest, scariest, and craziest decision I have ever made. It was also the best, as it let me make a living doing what I loved for almost two decades.

The ‘nightlife ninja’ is a term I gave myself. I always thought it was better to define yourself, rather than let society define you. In this case, when I was starting out, I was known as ‘that South Beach kid’ or the ‘promoter.’

It wasn’t until I made a name for myself that everyone knew me by my full name; I added ‘nightlife ninja’ because it was unique.  

What was the business model for Nightlife Ninja? In other words, how did you make money from this venture?

My specialty was bringing the masses, filling the spaces, and putting ‘butts in seats.’ I was paid to do this along with selling VIP tables. I started with nightclubs but expanded to brand launches, private parties, and more.

I was the best in this area and some of my largest events attracted 1,000 people. That wasn’t the total for the entire event; that was only from my personal list. When my competitors were struggling to deliver two dozen people, the value was evident.

No one expected that.

I would have lines out the door — flooding the street and causing traffic delays. People simply couldn’t believe not only the size of my network but also my ability to deliver.

What did you do with the money you earned?

I have always been frugal which means I saved it and thought of the future. This wasn’t easy in Miami, where everyone had to show off their flash at every possible chance.

While I was constantly out, I was cognizant of my spending habits. I invested the money in myself, stocks, a new VC fund (in which I am a partner), and funding my own endeavors. That isn’t to say I didn’t have fun.

You write a newsletter called YouTopian Journey. What did you hope to accomplish when you began writing YouTopian Journey and did you expect it to be so successful?

YouTopian Journey started as a pandemic project that allowed me to focus my energies during the lockdown on something that would help people.

I wanted to do something meaningful that could benefit society. I had high hopes that it would be successful but I didn’t know how many doors it would open.

There is a quote from Martin Buber that says “All journeys have secret destinations of which the traveler is unaware.” This continues to be evident nearly every day for me. 

You speak of conformity, especially founder conformity. What is founder conformity? 

Founder conformity is essentially founders falling into the conformity associated with startups. They begin talking the same, thinking the same, and acting the same.

It is ironic because founders usually start companies to escape the herd mentality of the corporate world but find themselves conforming to their new environment. And, like all conformity, it can be detrimental.  

Why is conformity a negative attribute?

You need to learn to think for yourself, experiment on your own, fail on your own, suffer on your own, and, eventually, conquer on your own.

You cannot forge your own path if you are following the path everyone else follows. As Heidegger wrote, “every man is born as many men and dies as a single one.” The same can be said of founders.

As if you weren’t busy enough, you also mentor founders and entrepreneurs who need guidance to realize their goals.

What were your reasons for becoming a startup mentor?

I am a startup mentor for Founder’s Institute and I also offer paid strategic sessions and workshops for my own founder clients.

This came about after working with numerous founders in different verticals and realizing that they all faced the same challenges and difficulties.

I wanted to offer my expertise to help founders avoid becoming another startup failure statistic.

As someone who’s still only in their 30s, which specific life lessons have given you the wisdom to preach to others?

I think being a serial entrepreneur (and a serial failure) is something that is invaluable.

I have failed at everything.

I failed at winning Jeopardy. Failed at tests. Failed in business. Failed at relationships.

Yet one thing I won’t fail is myself. We have to keep going.

There is nothing that teaches us more than failure. But failure is so demonized in our society that the vast majority of us are simply afraid to move forward..

We’re so afraid of the F on that test or failing the assignment our bosses give us that we won’t risk winning. This needs to stop. 

Entrepreneurs have begun to open up about mental health issues online and you have stirred up controversy with your views on this topic. What do you believe mental health means in this day and age?

I wouldn’t say my views are controversial, but they are blunt. Mental health means having difficulties, because as Carl Jung wrote, “they are necessary for health.”

Mental health doesn’t mean being happy every second of every day. It means facing external challenges, internal fears, and thoughts of doubt — and even dread. But a mentally healthy and strong person faces these thoughts and fears and moves ahead anyway.

They overcome themselves on a daily basis and receive no reward, only the challenge of doing it again tomorrow. Yet, this is a part of the human experience.

This is how strength is gained. This is how you personally grow. 

Miyamoto Musashi said it best when he wrote “Today is victory over yourself of yesterday; tomorrow is your victory over lesser men.” 

Is there something you hope to accomplish in life that drives you to keep going or that will define your existence?

Of course. All we have is our personal goals, and my goals are always changing. But rather than shirk from these goals due to their difficulties, I embrace them and keep moving.

Yes, it will be hard. Yes, it will take time. And yes, it may not work out. But it is better than the alternative of playing it safe and playing it small.

I want to be defined by my actions and what I accomplish.

I am currently shopping my feature film screenplay so that is a personal mountain for me to scale (I already have a production house and a great director attached).

I also have other creative and entrepreneurial goals that I intend to achieve — everything from writing comic books to having a thriving VC fund.

It is my ultimate hope that someone will be inspired by them so they can begin their own unique journey. 

Finally, Shaun, what’s the most valuable piece of advice you can offer new entrepreneurs?

The goal of life is to be defeated by greater and greater things. Don’t be afraid to do your own thing and fail.

Your natural curiosity and your own experiences are far better teachers than any job career you could pursue. 

Thanks, Shaun. It’s been a fun conversation. And, as they say in the movie business, that’s a wrap.

We look forward to welcoming you back to discourse soon. In the meantime, all the best with your screenplay.

Thanks, Juliet. I appreciate it.

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Juliet Lyall

Juliet Lyall is editor in chief for the discourse publication. She has been writing and editing articles and newsletters for digital businesses (mainly investing sites) for 10+ years. As an entrepreneur, Juliet has built and worked with bootstrapped startups for 20+ years and is proud to support other women in their online journeys. The Oxford comma. Always.

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