What It Takes To Be A Successful Entrepreneur—And Why It’s A Mind Game

By Rieva Lesonsky

The startup surge is still in high gear. Last year, according to the U.S. Census Bureau, Americans filed a record-breaking 5.5 million applications to start new businesses. From January through March of this year, 1.5 million new business applications have already been filed. (These numbers are not seasonally adjusted.)

Recent research from Zen Business reveals that 80% of Gen Z think they will “become the most entrepreneurial generation in U.S. history,” and 75% want to be entrepreneurs.

Obviously, these startup business owners enter the entrepreneurial fray filled with grand dreams, innovative ideas, and hope. But are they prepared for the reality of entrepreneurship?

To get an entrepreneur’s perspective, I talked to Clate Mask, the CEO and co-founder of Keap, a small business automation software company. Mask just released a new book, Conquer the Chaos: The Six Keys to Success for Entrepreneurs, an update to his New York Times best-seller released in 2010.

Why success in entrepreneurship isn’t easy

Rieva Lesonsky: You say you wrote this update to Conquer the Chaos for “the entrepreneur who went into business looking for freedom and instead found chaos.” Do you think most entrepreneurs start businesses expecting a chaotic ride, or do they think they’ll experience a relatively smooth path to success?

Clate Mask: Most entrepreneurs are visionaries with big ideas but often struggle with how to execute them. They know that building a successful business won’t be easy, but their ambition and excitement can cause them to underestimate how truly difficult it can be. So, they probably expect some chaos throughout the journey, but they’re shocked by just how chaotic things really become.

Lesonsky: Why do so many choose business ownership, knowing it’s not easy?

Mask: Entrepreneurship dangles a very appealing carrot. The idea of time freedom, limitless earning potential, and being your own boss is a draw that’s hard to ignore. Most people, especially entrepreneurs who already possess great grit, are willing to push through some pain to get to the rewards on the other side.

Lesonsky: Can you define “chaos” as you mean it in the book? Has the chaos changed in the 14 years between the publication of both editions?

Mask: In the book, I use the analogy of stepping into a gym for the first time, all geared up to kickstart your fitness journey. You hop onto a treadmill and initiate a warm-up walk. Suddenly, a gym trainer approaches and cranks up the treadmill speed. You transition into a jog, feeling apprehensive yet overcoming the initial challenge.

But the trainer doesn’t stop there. They increase the speed further and elevate the incline. Now, you’re struggling to keep pace. Despite feeling out of your depth, you persist, driven by a reluctance to give up or appear inadequate. Deep down, you realize this isn’t quite what you envisioned when you stepped into the gym. You continue, feeling trapped on the relentless treadmill.

The chaos of managing a small business mirrors this treadmill experience. Customer demands loom constantly. Leads require attention, projects await completion, bills must be paid, and crises demand resolution. Meanwhile, technology advances rapidly, complicating data management, while administrative and compliance tasks remain challenging. Industry dynamics evolve, competitors encroach, and economic fluctuations add further complexity.

And that’s just the business side of things! Amid all this, entrepreneurs also juggle their children’s schedules, neglected health, personal finances, household maintenance, and crucial relationships. The moment prospects and customers enter the picture, chaos ensues. Inputs multiply, leading to disorganization, and priorities blur, with overwhelm looming ominously.

Lesonsky: Can you briefly describe how someone can conquer the chaos?

Mask: Conquering the chaos starts with mastering “the game between your ears.” Once you’ve done this, you can focus on your vision and rhythm, preparing you for the business keys to success (strategy, automation, and leadership).

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How to change your mindset for success

Lesonsky: How do you cultivate a “winning mindset?”

Mask: Small business chaos is in the mind even more than in the physical world, which is why overcoming the negative thoughts and emotions that arise inside you as an entrepreneur is the number one Key to Success in your business and personal life.

When I was young, my dad always talked about the importance of staying positive, but I didn’t pay much attention as a teenager. Then, when I was struggling to keep my small business afloat and facing personal financial problems, a book he had recommended years ago caught my eye: The Power of Positive Thinking by Norman Vincent Peale.

Reading that book changed everything for me. It not only turned my life around but also saved my business. If I hadn’t learned to change my way of thinking during those tough times, Keap wouldn’t exist today. I’ve spoken to many other entrepreneurs who’ve been through similar challenges because running a business often feels like dealing with one failure after another.

Every day, it’s important to focus on having a mindset geared toward success. That means deliberately practicing positive thinking and performing mental exercises to train your brain to overcome obstacles and achieve your goals. Two of the top ways I recommend doing this are creating a morning routine that helps you feed positivity and purge negativity, and exercising every day. Even 20 minutes of exercise can be a game-changer for your mind and mindset.

Lesonsky: You say you need a “life vision” to be successful. How do you figure out what your life vision is? And does it change as you get older?

Mask: Establishing your vision involves thoroughly examining your identity, purpose, values, mission, and goals. It’s a process of introspection and self-definition, starting with a clear understanding of who you are. It includes:

• Defining your identity. This sets the stage for understanding your purpose—why you’re here and what you aim to achieve in life.
• Delving into your values. This helps identify the principles that guide your actions, while crafting your mission allows you to outline the overarching objectives you seek to fulfill during your time on earth.
• Setting goals. Putting goals in place across various facets of life, such as in physical, spiritual, social, business, and financial areas, provides a roadmap for actualizing your vision.

The journey to clarify your vision involves asking yourself fundamental questions about your identity, purpose, values, mission, and goals. This process can take various forms, from solitary reflection to seeking input from trusted friends and family. There’s no one-size-fits-all approach, but commitment and intentionality are essential.

Your goals may evolve as you engage in this process, and your life mission may adapt over time. However, the key lies not in setting it and forgetting it but in integrating it into your daily routines and periodically reassessing it to ensure alignment with your evolving aspirations. By incorporating your vision into your regular rhythms of life, you create a framework for continuous growth and fulfillment.

Lesonsky: You talk about “conscious capitalism,” which you write means a business should be “used to do good for everyone associated with the business,” in other words, customers, employees, partners, owners, and the community. But the reality is not all entrepreneurs feel that way. I know—I’ve worked for a few. So, how do you convince business owners that being a conscious capitalist is worth it?

Mask: I fully believe in following the practices of conscious capitalism, but you’re right—some business owners don’t feel the same way. Sometimes, their ambition or short-sighted view of what it will take to make their own business thrive gets in the way of embracing the long-term advantages—to everyone involved—of conscious capitalism.

All I can say to these people is that using your business to do good for every person who interacts with it is more fun and fulfilling, and, in the end, following this path will leave you with fewer regrets.

What successful entrepreneurs have in common

Lesonsky: Now, let’s discuss Keap’s new survey and report, The State of Business Growth 2024. What are the traits of business owners you classify as “growth achievers?”

Mask: Our report is eye-opening about what currently separates the entrepreneurs who are growing from the ones who are stagnant or even on the decline. The “growth achievers” are the 80% of those surveyed who have exceeded or met their goals, while the “underperformers” are the 20% who missed their goals.

This year’s report showed some compelling patterns among the growth achievers. The research made it clear that this group is far more likely than underperformers to have planned investments in AI, process automation, partnerships, and software. Growth achievers embrace innovation and focus their investments on these key business areas that continue to fuel their growth.

Lesonsky: In one of the questions in the survey, owners of emerging businesses cite “building credibility and trust” as a challenge. In another question, all three types of companies (emerging, scaling, and mid-market) say “building customer loyalty” is challenging. What’s your advice for building credibility, trust, and customer loyalty?

Mask: Building credibility, trust, and customer loyalty hinges on several key principles. First and foremost, you must set accurate expectations and avoid overpromising. By being transparent about what you can deliver and then meeting or exceeding those expectations, you establish trust and reliability with your customers.

Secondly, investing time and energy into your relationships with customers is essential. Whether through personalized communication, attentive listening, or going the extra mile to address their needs, you’ll foster loyalty when you show genuine care.

Additionally, staying focused on your target area rather than trying to cater to everyone’s demands ensures you can consistently deliver high-quality service. Finally, maintaining consistent follow-up and follow-through shows your commitment to customer satisfaction and reinforces their trust in your business.

About the Author

Rieva Lesonsky is CEO of GrowBiz Media and SmallBusinessCurrents.com and has been covering small businesses and entrepreneurship for over 30 years. Get more insights about business trends by signing up for her free Currents newsletter.

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