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Startup Savvy: Stephen Flanders Of Raffle Leader Shares Their Secrets For Rapid Growth and Success

An Interview With Eden Gold

You need to be a good storyteller. Whether you’re writing an ad, making a sale, or pitching to investors, you need to be able to describe your business in a compelling way. Nobody wants to buy flavored water. They want to buy the future of sports hydration.

The entrepreneurial landscape is more vibrant and challenging than ever, with young entrepreneurs at the forefront, driving innovation and redefining the boundaries of success in the business world. These dynamic individuals are not only creating new products and services but also building sustainable business models that thrive in today’s fast-paced, technology-driven environment. Their journeys are filled with lessons of resilience, strategic innovation, and the relentless pursuit of growth. As part of this series, we had the pleasure of interviewing Stephen Flanders.

A lifelong entrepreneur, Stephen turned his passion for writing and technology into one of the most successful writing agencies in the tech space, with clients including venture-backed startups, founders with 100’s of thousands of followers, and newsletters with millions of subscribers. Always hungry for a new challenge, Stephen is now turning his attention to building his software company, the WordPress plugin Raffle Leader, with his brother.

Thank you so much for joining us in this interview series. Before we dive into our discussion about cultural sensitivity, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Sure. My parents are entrepreneurs, I’ve always been fiercely independent, and I’ve always been a hustler, so, naturally, I’ve always wanted to be an entrepreneur. But, prior to college, I didn’t know exactly where I’d take it. That changed in 2021 when I found a passion for tech. Seeing how much potential tech has to change the world for the better instantly convinced me that this is where I needed to be.

Can you share the most interesting story that happened to you since you started your career?

I had a meeting with a potential client, and what he wanted was a newsletter that heavily emulated the most popular newsletter in his industry. About 6 hours later, the person behind the popular newsletter reached out to me about working together, and she later became one of my best clients!

You are a successful individual. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The most important trait, by far, is grit — or, as I like to call it, having that dog in you. Things aren’t going to go the way you plan them the vast majority of the time. If you aren’t able to keep pushing in the face of adversity, then the entrepreneur life isn’t for you. The second is a high-risk appetite. Being a successful entrepreneur is anything but assured, and it’s definitely not something that will come quickly. You have to be comfortable with the idea of failing. Lastly, I think you need to be curious and adaptable. The quickest way to fail is to be stubborn. When a good idea or new piece of technology comes around, you have to be ready to pounce.

Ok, thank you for that. Let’s now jump to the primary focus of our interview about young entrepreneurs secrets to rapid growth and success. To start, how would you define success?

Success is living the life you want to live. If that’s as an entrepreneur, that’s great. If that’s as a philanthropist, that’s awesome. If that’s as a traveling basket weaver, that’s cool too. As long as you’re doing what you want, then you’re successful.

What unconventional strategy did you employ that significantly contributed to your startup’s growth, and why do you think it was so effective?

We do all of our work asynchronously, so no meetings unless they are absolutely necessary. Time is the most valuable resource we have, and very rarely can a meeting not be summed up in an email, so why waste time on something that doesn’t move the needle? I think people would be better served taking this approach in most facets of their business. Don’t write a page when a paragraph will do. Don’t take a meeting when an email will do. And don’t pay for expensive software when Google Docs will do.

Can you share a critical pivot point in your startup’s journey and how you navigated the decision-making process?

About 6 months ago, I realized that scaling my agency was no longer what I wanted. Adding enough quality writers to keep up with demand is basically impossible. As a result, the quality of your work goes down as you scale, and that’s not what I got into the business for. So, I realized that if I wanted to continue to climb the ladder, I’d have to pivot to a business model where I could scale without needing additional manpower. Thus, my brother and I started Raffle Leader.

How do you balance the need for rapid growth with maintaining a sustainable and healthy company culture?

It’s actually easier than you’d think. Rapid growth goes hand-in-hand with a healthy company culture. As the saying in sports goes, if you look good, you feel good, if you feel good, you play good, and if you play good, they pay good. It’s the same thing in business. If your employees feel good, they work good, and if they work good, you grow good.

In what ways has your personal definition of success evolved since the inception of your startup?

The main thing is that I’m much more willing to celebrate the small wins. Everyone gets into entrepreneurship thinking they are going to get rich quickly, but that couldn’t be further from the truth. Everything takes much longer and is much more expensive than you’d expect. So, when my team ships a feature, that’s a win. When we make a sale, that’s a win. It is from repeatedly stacking these small wins that the big win is eventually found.

Based on your experience and research, can you please share “5 Things You Need to Succeed as a Young Person in Business?”

1 . As I said earlier, you need to be gritty. Things aren’t going to go your way the vast majority of the time. You need to be able to pick yourself up and get back on the horse. If you’re not able to deal with failure, criticism, and disappointment, then business isn’t the right field for you.

2 . Second, you need to be a good storyteller. Whether you’re writing an ad, making a sale, or pitching to investors, you need to be able to describe your business in a compelling way. Nobody wants to buy flavored water. They want to buy the future of sports hydration.

3 . Third, you need to be a good listener. You need to listen to your investors, your employees, and, most importantly, your customers. That’s how you truly improve your business.

4 . Relatedly, fourth, you need to have conviction. It’s super easy to get lost in the noise of opinions. Only through your own conviction can you find signal in that sea of noise.

5 . Fifth, you need to be adaptable. If something isn’t working, you need to be able to pivot on a dime. Stubbornness has been the downfall of countless entrepreneurs.

What is one piece of advice you would give to an aspiring entrepreneur that you wish someone had given you at the start of your journey?

Unless you already have money, don’t take too big a swing on your first try. Start something smaller and get a win under your belt so that you have some funds to play around with. The key to success as an entrepreneur is to just stay in the game. Having some money to support yourself helps a lot In this regard.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I think AI is an amazing technology, but I am also worried about short-term job disruptions. So, I think it’d be great if somebody could start a program that reskills workers if they get laid off due to AI.

How can our readers further follow you online?

On Twitter/X @SteveFlanders22

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work! Thank you!

About The Interviewer: Eden Gold, is a youth speaker, keynote speaker, founder of the online program Life After High School, and host of the Real Life Adulting Podcast. Being America’s rising force for positive change, Eden is a catalyst for change in shaping the future of education. With a lifelong mission of impacting the lives of 1 billion young adults, Eden serves as a practical guide, aiding young adults in honing their self-confidence, challenging societal conventions, and crafting a strategic roadmap towards the fulfilling lives they envision.

Do you need a dynamic speaker, or want to learn more about Eden’s programs? Click here: https://bit.ly/EdenGold


Startup Savvy: Stephen Flanders Of Raffle Leader Shares Their Secrets For Rapid Growth and Success was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.