November is Entrepreneurship Month, where we honor the dreamers, the doers, and the resilient warriors of the business world. Whether you’re just starting your entrepreneurial path or reflecting on years of lessons, this journey is a rollercoaster ride of wins, setbacks, and moments that define us.
In this Dopamine Dose edition, I’m diving into the lessons I’ve learned from 20+ years of experience of launching 16 companies—lessons shaped by both triumphs and mistakes. Let’s explore how innovation, resilience, and human connection drive entrepreneurial success. Plus, we’ll tackle a question on everyone’s mind: Is entrepreneurship evolving, or is it fading?
The Golden Era of Entrepreneurship: Are We Facing a Shift?
Entrepreneurship has come a long way. From the early days of the internet boom to the excitement of Shark Tank moments, we’ve seen an entrepreneurial explosion like no other. Today, there are approximately 500 million entrepreneurs worldwide, with 31 million in the U.S. alone. It’s been an era defined by resilience, grit, and relentless innovation.
But as technology advances, some are wondering: Is entrepreneurship evolving, or are we losing what makes it truly powerful?
The emergence of AI and automation has added a new layer to the conversation. With AI taking over repetitive tasks and optimizing processes, some say we risk losing the very qualities—grit, creativity, and a relentless drive—that have traditionally defined the entrepreneurial spirit. The core question is this: How do we use technology to evolve while staying true to what makes entrepreneurship meaningful?
🔵 Entrepreneurship isn’t about shortcuts. It’s about resilience, passion, and solving problems that matter. AI can streamline, but it can’t replace the human spirit that fuels innovation.
For me, it’s all about integration. Imagine Tony Stark and Jarvis: humans and technology working together, not in place of one another. Real progress happens when we use tools like AI to free up our time and enhance our strengths—not replace our creativity, passion, or problem-solving skills.
Discovering Your “Why”: The Foundation of Every Entrepreneur
Technology and tools will continue to evolve, but one thing that will always be essential in entrepreneurship is having a clear, compelling why. When I first started, I was head-down, grinding toward profits. But without a bigger purpose guiding my journey, I often found myself going through the motions.
That changed after a trip to Necker Island with Sir Richard Branson. Watching him build not just businesses, but communities, I learned that true success comes from having a mission that drives you beyond the numbers.
Your why is your anchor. It’s the foundation that keeps you focused and aligned, even in uncertain times. And here’s why it matters: First-time entrepreneurs only have an 18% chance of success. But those who understand their purpose and align their actions with it see much higher rates of success.
Action Step: Reflect deeply on your “why.” Take the time to clarify your purpose:
🔵 What impact do you want to make?
🔵 How will your work contribute to something greater?
🔵 Who are you serving, and why does it matter?
When your purpose is clear, you’re not just building a business—you’re building a legacy.
Prioritize Your Well-being: The Key to Sustainable Success
Let’s get every day is a silent killer for entrepreneurs. Early in my career, I thought working myself to the bone was a badge of honor. But the truth? That mindset left me drained, unproductive, and disconnected.
It wasn’t until I prioritized my health, incorporating workouts on my Peloton, participating in Spartan races back in the day, or running with my son Jayden, that I realized how crucial well-being is to leadership. When your energy is high, your focus sharpens, your creativity flows, and you’re able to tackle challenges head-on.
💥 A fit body supports a sharp mind, and a sharp mind drives a successful business.
Stats to back it up: Did you know that physical activity can boost productivity by up to 21%? Entrepreneurs who prioritize their health report greater resilience and decision-making ability.
Action Step: Build wellness into your daily routine. Schedule time for physical activity, prioritize quality sleep, and make space for moments of mental reset. It’s not about perfection—it’s about consistency.
The Human Connection: Building Relationships That Last
Forget vanity metrics and surface-level networking. Real success is built on authentic connections. According to Inc. Magazine, 77% of entrepreneurs say strong relationships with peers and mentors are critical to their success.
Mark de Grasse has been working in branding and content creation for 20 years. He’s a friend, peer, and fellow entrepreneur. Your network is your net worth.
And yet, 55% of entrepreneurs struggle to reach their target customers. Why? Because trust takes time, and it’s earned through genuine engagement, not flashy pitches. My best partnerships and biggest opportunities have always come from real conversations, not forced sales tactics.
Action Step: Invest in your network. Comment thoughtfully on LinkedIn, send personal messages to check in on your connections, and show up authentically in every interaction. People work with people they trust—not just people who sell well.
Entrepreneurship as a Team Sport: The Power of Partnership
Entrepreneurship is a wild ride, but doing it alongside Rachel? That’s a whole new level. She’s not just my wife; she’s the Chief Marketing Officer, a branding powerhouse, and the ultimate LadyBoss. When Rachel B. Lee left her corporate career to join me at StandOut Authority, she brought with her the experience, strategy, and fearless energy that’s helped take our business to new heights.
My partner Rachel B Lee is the yin to my yang in all aspects of life.
Here’s what I’ve learned: Entrepreneurship is about more than building a business. It’s about surrounding yourself with people who challenge you, push you to be better, and share your vision. Rachel’s transition from corporate America to entrepreneurship didn’t just boost our business; it redefined what’s possible when two people bring their unique strengths together.
Rachel, your leap of faith, your expertise, and your unwavering commitment to our shared vision inspire me every day. To anyone wondering if family and business can mix: Hell yes, it can. And when it works, it’s pure magic.
AI and Entrepreneurship: A New Era of Possibilities
Let’s talk about the game-changer that is AI. At StandOut Authority, we’ve embraced AI to automate mundane tasks, supercharge our content, and analyze market trends. But we also understand that AI is a tool, not a replacement. According to Microsoft’s 2024 Work Trend Index, 90% of users say AI saves them time, and 84% feel it makes them more creative.
This perspective is echoed by experts who emphasize the importance of maintaining the human touch in the age of AI. For instance, an article from Entrepreneur highlights that while AI can handle data analysis and routine tasks, it cannot replicate genuine human connections and empathy, which are vital in building meaningful client relationships.
MIT Sloan also puts it perfectly—human creativity is what makes the magic happen. It’s the key to connecting the dots across different fields and pushing boundaries in ways AI alone just can’t. When we bring our creative spark to the table, AI becomes a powerful tool to help us build sustainable, long-term advantages.
AI is opening doors to insane levels of efficiency and innovation, but real entrepreneurial success? That still comes down to us. It’s about blending the power of tech with the irreplaceable stuff—our creativity, empathy, and ability to build real, human connections. That’s where the magic happens.
Gen Z: The Next Wave of Entrepreneurs
As a dad to two Gen Z kids, I’ve got a front-row seat to the way this generation is reshaping entrepreneurship. They’re bold, resourceful, and unafraid to disrupt the status quo. 54% of Gen Z plan to start their own business, and 84% aim to do so within the next five years.
What sets them apart? Research. They dive deep into understanding their markets, leveraging digital tools to refine their ideas. And in a world where 20% of businesses fail within the first two years, this skill is critical for long-term success. Gen Z is showing us that with the right blend of research, resilience, and relationship-building, they’re ready to take on the entrepreneurial world.
A Letter to Entrepreneurs
Dear Aspiring Entrepreneur,
We accept the fact that we’ve chosen a path filled with late nights, early mornings, and more risks than most people would dare to take. But we think it’s wild to ask us to define what it means to be an entrepreneur.
You see us as you want to see us: in the simplest terms, in the most convenient labels. You call us dreamers, hustlers, disrupters, or maybe even fools chasing impossible goals. But what we’ve discovered is that each one of us is much more than that.
We’re the visionaries who imagine a better world…
The builders who create something from nothing…
The risk-takers who bet on ourselves when no one else will…
The learners who fail fast and pivot faster…
And the connectors who bring people together for a common cause.
Does that answer your question?
Sincerely yours,
The Entrepreneurs’ Club
If this feels familiar, it’s because we all have a bit of the Breakfast Club spirit in us. Like those iconic characters, entrepreneurs defy easy categorization. We’re complex, driven, and constantly evolving. This entrepreneurial journey isn’t about fitting into a box—it’s about breaking out of one.
Your Journey, Your Legacy
Entrepreneurship isn’t just a career path; it’s a lifestyle, a mindset, and a commitment to growth—both personally and professionally. It’s about embracing change while staying anchored to your purpose. Whether you’re using the latest AI tools or building authentic relationships, remember this: the true power of entrepreneurship lies in resilience, connection, and vision.
Now, it’s your turn. Share your story, your lessons, and your wins. Let’s inspire each other to keep building, innovating, and leading with purpose. Join the conversation and let’s keep this momentum going. 💬
20 years, 16 companies, and $500M+ in ad spend later, here’s what I’ve learned: success isn’t about chasing trends—it’s about building connections that last.
I recently sat down with Adam Levinter on the Entrepreneurs Exposed podcast to talk about:
✅ The early days of online marketing
✅ How leaders can drive growth on LinkedIn without “selling”
✅ Why real success comes from authentic human connection
If you’re ready to turn LinkedIn into a true growth engine, this episode is for you.