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Leadership
April 16, 2025

Do You Have What It Takes? 5 Signs You’ll Succeed in Entrepreneurship

Post By:
Nicole Mastrangelo
In-House Contributor
CoFounder | CEO
The Daily Drip
Guest Contributor:

Every day, I walk my son to and from school. As hard as it is on busy workdays, I cherish these walks. I know I’ll only get so many of them. And the conversations we have are always the best.

One afternoon, on the walk home from school, Sebastian asked me, “Mom, what’s your job?”

I’d been waiting for this moment, this question, for a long time. There’s so much I want to teach him, so many values I want to instill, all stemming from the answer to this question. So, I went in for the kill.

“I don’t have a job I have a business,” I said.  He looked at me confused and asked, “You don’t have a boss?” 

“No, I am the boss because I have a business. And the business creates jobs for other people,” I said.

By now the wheels were spinning. I could see his little brain trying to process this answer. Sure enough, the next big question came. “So how do you make money?” he asked.

“I find really big, important problems and solve them. Then the business sells the solutions. People come to my business to buy them,” I said.

“So how much money do you make?” he asked. The audacity of an 8-year-old.

“However much I want. If I can create a solution people really want or need, something that solves a really important problem, I can ask for lots of money, and lots of people will buy it so they don’t have that problem anymore.  And I can do this over and over, solving as many problems as I want. So, I can make however much money I want.”

His eyes almost popped out of his head. This is the same kid who wheels and deals how much allowance and birthday money he can spend on Pokémon cards and Fortnite skins. The idea of a limitless supply of money was more than he could handle.

“Like a million dollars?!” he screamed.

“More! Like $10 million, $100 million!” I said.

“So, do you have a million dollars?!” by now he’s squealing.

“Not yet. Almost. It’s challenging and takes time to find the problem, create the solution, and let people know you have it. But if you can be patient and work hard every day towards those 3 things, you will. I’ve had my business for 4 years and I’m halfway there,” I said.

He didn’t deflate as much as I thought he would. He just kind of processed it all, trying to make sense of it, trying to decide how he felt about it. 

“It’s hard to invent something,” he said.

“It’s actually easier than you think. There are problems everywhere if you really pay attention, look around, and listen. It’s harder to be strong and consistent. It’s harder to be patient and not give up. It’s harder to keep going and keep building your solution when something goes wrong, or you make a mistake. Most people give up. But to me, finding problems and creating solutions is fun! I have a lot of fun every day! Even though it can be hard. It’s the most fun when I finally create a solution and get to share it with people. It makes them happy and that makes me happy and want to do it more.” 

He looked up at me, smiled and said, “That’s cool. I didn’t know you could do this when you grow up.” 

Of course he didn’t. He certainly isn’t going to learn it in school. It’s up to me to talk about it. 

And by it, I mean, the three most important things I believe we can teach our kids to set them up for success, even when the future is most uncertain: problem solving, resilience, and all about the tool that runs the world: money. How it works, how to manage it, how to create it, how to neutralize emotions around it. 

Growing up in a small business family, conversations about money, investing, and business were routine. I never appreciated it until I grew up and realized just how rare that was. In a 10-minute walk, Sebastian learned what takes most adults years to learn the hard way. I know this because I speak with business owners of all stages every single day.

Some of my favorite conversations are with new entrepreneurs. These ambitious founders and motivated ex-corporate solopreneurs have all the enthusiasm and wide-eyed optimism of my 8-year-old. And like Sebastian, they’re curious, they’re learning. They’re trying to figure out how business and money work, both separately and interconnectedly. They’re trying to make sense of all the pieces while trying to decide how they feel about it along the way.

Inevitably, they will have blind spots and underestimate just how long it will take to reach their initial goals. They’ll make tons of mistakes, some that will rock them more than others. They’ll have expectations of the journey that won’t be met. And they’ll eventually find themselves asking: 

Did I make the right decision? 

Can I do this?

Should I keep going?

20% of them will quit or fail in the first year. 50% in 5 years. 65% in 10 years. There are common threads as to why this is. There are also commonalities among those who succeed. Clear signs that indicate the entrepreneur and his or her business will not only survive but thrive. 

If you’re on the business building journey, and asking yourself these questions, here are 5 signs you have what it takes to succeed. 

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  1. You’re Observant. You notice details and patterns others miss, identifying small signals as big opportunities. You’re constantly scanning market trends, consumer behavior, and industry shifts. This awareness helps you spot unmet needs and emerging gaps before others do. Instead of reacting, you anticipate change and build solutions with precision. This gives you a sharp edge, allowing you to stay ahead of the curve and create real value for consumers.
  2. You’re a Problem Solver. Driven by creativity and innovation, you thrive on challenges, seeing them not as roadblocks but as invitations to build smarter, better solutions. You adapt, iterate, and evolve because you know the work is never truly done. Each solution leads to new insights, and you're always ready to rethink, refine, and rebuild. This mindset keeps your ideas relevant and your ventures resilient in ever-shifting landscapes.
  3. You Have High Pain Tolerance. You’re able to endure extended periods of discomfort, setbacks, and sustained challenge without losing momentum. Entrepreneurship absolutely tests your limits, and you meet it with grit, sacrifice, faith, and unwavering focus. Grounded in patience and the understanding that building takes time, you know that success does not come in overnight wins and understand you’re playing a long game.
  4. You Are Disciplined. You are ready and willing to roll up your sleeves and put in the work every single day. You maintain consistency, prioritizing the small, daily actions that compound over time. You have unwavering commitment and continue to show up during times of setback. Your resilience isn’t just about toughness. It’s about staying committed through the hard, unglamorous parts of building something meaningful.
  5. You’re a Strong Communicator. With the ability to connect, influence, and inspire through your words and presence, you build trust, relationships, and vision with confidence and conviction. Your storytelling makes ideas resonate, and your interpersonal skills turn connections into collaborations. Whether pitching, leading, or listening, you make people feel seen, heard, and validated- and ready to support you!

One more bonus sign- You’re passionate. Not just about a cause or mission or product or service. You’re passionate about these 5 traits themselves. They’re not just skills to develop or muscles to build. They’re principles that shape who you are and how you show up for the world every day. 

And that’s how you succeed, no matter the circumstances, environment, or landscape.

A few days after our walk, Sebastian came home from school with his career day artwork. In a classroom full of aspiring Youtubers, his said: “When I grow up I want to be an INVENTOR.”