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How Do You Cultivate a Winning Entrepreneurial Mindset?

woman with a winning entrepreneurial mindset

To help you cultivate a winning entrepreneurial mindset, the team at Featured has gathered fourteen insightful responses from CEOs, entrepreneurs, and other industry leaders. Here are their thoughts, in order:

  • Take the Squash Player’s Approach
  • Embrace Failures as Steppingstones
  • Leverage a Strong Support Network
  • Remember Your Roots and Set Stretch Goals
  • Prioritize Perseverance, Flexibility, and Passion-Driven Purpose
  • Internalize Lessons from Coding and Gaming
  • Build Resilience through Mindfulness Practices
  • Choose Courage and Fearlessness
  • Create Value Over Celebrating Victories
  • Try Stoicism and Negative Visualization
  • Spread Infectious Optimism
  • Reflect on Achievements and Setbacks
  • Network and Keep an Open Mindset
  • Learn from a Collaborative Competition Analysis

Do It Like A Squash Player

Take the Squash Player’s Approach

Cultivating a winning mindset as an entrepreneur, for me, is a lot like playing squash, a racket-and-ball sport played by two players.

In other words, you need to be agile, quick to adapt, and always anticipating your opponent’s next move. Similarly, as an entrepreneur, you need to be ready to pivot, adapt to market changes, and anticipate customer needs. And just like in squash, resilience is key. You’re going to face challenges and setbacks, but it’s all about getting back up and keeping your eye on the ball. It’s a game of endurance, strategy, and resilience.

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Lou Reverchuk, Co-Founder and CEO, EchoGlobal

The Entrepreneur Mindset: Embracing Failures as Steppingstones

In my journey as an entrepreneur, I’ve learned not to see failure as the end but rather as a stepping-stone. This perspective has become essential to cultivating a winning mindset. Instead of being scared of making mistakes, I welcome them and view each one as an opportunity for growth, learning, and improvement.

Simply stated, this mindset keeps me motivated, even when the odds seem stacked against me. It’s about persistence and resilience, not allowing setbacks to defeat you but instead using them to fuel your determination.

According to one of my favorite books, Failing Forward, “there are no mistakes, only lessons.” In the end, this resilience can become the very thing that sets you apart and drives you toward success.

Juliet Dreamhunter, Founder, Juliety

Get A Support Network

Leverage a Strong Support Network

As the CEO of a web-scraping business, my entrepreneurial journey has taught me that fostering a winning mindset is paramount. Personally, the keystone to my resolve has been the development of a strong support network. There was a critical juncture early in our business when a significant client backed out.

As a startup, this was a heavy blow. However, instead of letting this setback crush our spirit, I turned to my support network—mentors, friends, and family. Their encouragement and guidance not only lifted my spirits but also offered fresh perspectives, helping us strategize more effectively.

Through this experience, I understood that a strong support network is a potent tool for cultivating resilience and a winning mindset as an entrepreneur.

Daniel Pfeffer, CEO, Scrape Network

Remember Your Roots and Set Stretch Goals

There are three main things that I do to cultivate a winning mindset as an entrepreneur.

The first is to remember where I came from. Remembering where I came from and the challenges that I used to experience becomes my success story and one of the biggest drivers for further success. 

Second, in order to maintain a winning mindset and cultivate an even better one, I focus on my “why.” Much like the first point, focusing on my “why” pulls me even further toward reaching my full potential and further developing my winning mindset.

Last, to cultivate a winning mindset, I continue to create goals that stretch me and set new ones as I approach the completion of those goals. If I don’t create new goals as I approach the completion of my current goal, it is likely that I will become complacent and lose that winning mindset.

Sebastian Jania, Owner, Ontario Property Buyers

Prioritize Perseverance, Flexibility, and Passion-Driven Purpose

As the CEO of Authors on Mission, cultivating a winning mindset is central to my entrepreneurial journey. It boils down to three key elements:

  1. Perseverance: Embrace setbacks as steppingstones towards success. They’re invaluable learning opportunities.
  2. Flexibility: Stay adaptable and open to change. In a rapidly evolving business landscape, the ability to pivot is crucial.
  3. Passion-Driven Purpose: Align your business with a purpose you’re deeply passionate about. This fuels motivation and resilience, propelling you forward even amidst challenges.

Remember, a winning mindset isn’t about avoiding failure, but persisting through it with learning, adaptation, and passion.

Vikrant Shaurya, CEO, Authors On Mission

Internalize Lessons from Coding and Gaming

Cultivating a winning mindset as an entrepreneur draws heavily from my own experiences in coding and gaming. I believe the first step is to set clear, achievable goals, much like when I’m trying to reach the next level in a game.

Then, we must face challenges head-on. If a line of code doesn’t work, we don’t quit, but persist, learn, and adapt. Resilience, learned from countless hours of debugging and grinding through gaming levels, becomes a cornerstone of this mindset. Next, staying curious and always learning, just as coding languages and games evolve, is vital.

Finally, to stay ahead, I continuously push my boundaries and learn new strategies. This combination of goal setting, resilience, and continuous learning shapes a winning mindset.

Lucas Wyland, Founder, Steambase

Build Resilience through Mindfulness Practices

As an entrepreneur, my personal anchor has been resilience. I’ve often had to remind myself that setbacks aren’t definitive losses, but instead, opportunities to learn, grow, and adjust my approach.

Through mindfulness practices—such as daily breathing exercises, meditation, and journaling—I’m able to manage stress, meet deadlines, handle my team interactions, and empathize with my customers in a more effective, compassionate way. On the busiest of days, this approach helps me stay focused and develop a positive, solution-focused mindset. It not only leads me to success but also ensures my motivation stays high and supports my entrepreneurial journey.

Bayu Prihandito, Psychology Expert, Life Coach, Founder, Life Architekture

On Courage And An Entrepreneurial Mindset

Choose Courage And Fearlessness

Your desire for freedom must outweigh your desire for safety. Don’t attempt anything business-related if you can’t overcome your fear.

In other words, you shouldn’t become an entrepreneur if you need ongoing affirmations, regular reassurance, or feel the need to read a thousand books before you get the guts to try. And don’t do this if you find it difficult to work independently and maintain motivation.

Being fearless isn’t the goal; the goal is having faith in your ability to get through. Jumping out there without a net is terrifying throughout the entire process, but for me, the thought of getting older, working jobs I detested, spending years in the same position and earning the same salary, and never even attempting to work for myself actually scared me more.

Jonathan Merry, Founder, Moneyzine

Create Value Over Celebrating Victories

I’ll always remember the time when I landed our first big client. Instead of simply celebrating, I analyzed the value we created for them. I realized that our value didn’t stem from the high-quality campaigns we designed, but from the trust they had in our ability to deliver results.



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That day, I understood the importance of focusing on creating value over celebrating victories. It’s about embedding the ethos of creating tangible benefits into the DNA of your approach. This mindset helps you turn challenges into opportunities. It’s not always easy, but it’s incredibly rewarding.

Joe Troyer, CEO and Growth Advisor, Digital Triggers

Try Stoicism and Negative Visualization

Stoicism is a powerful ally in cultivating a winning mindset. Through the practice of negative visualization, a core Stoic technique, challenges can be anticipated. It’s akin to evaluating potential risks before approving a loan—foreseeing the obstacles has enabled the design of effective solutions and strategies.

Major global events, such as the 2008 recession and the COVID-19 pandemic, rather than discouraging, served as opportunities for growth. As Stoicism teaches, these were accepted as natural market fluctuations and the business model was adapted accordingly. This mindset mirrors the management of high-risk portfolios and navigation through market instabilities.

Fred Winchar, Founder, Certified HR Professional, MaxCash

Your Entrepreneurial Mindset: Spread Infectious Optimism

Optimism must be completely embodied by an entrepreneur. There is no point in even entering the challenging and risky world of business if you do not believe you have a chance of winning the big game. An entrepreneur armed with optimism can navigate even the toughest objections and setbacks. They see opportunities where others see obstacles.

To that end, having a positive outlook as a businesswoman is important. When bad moments come, there’s always a way out. If a bad decision is made, it’s important to keep in mind that no one is perfect. If failure occurs, then failures are important life lessons.

In a nutshell, optimism acts as a magnetic force that draws people in. It’s contagious! Approaching a potential client or customer with genuine enthusiasm and a positive mindset creates a ripple effect. Optimism becomes infectious, allowing trust and rapport with clients to be built.

Samantha Hawrylack, CEO, SJ Digital Solutions LLC

Reflect on Achievements and Setbacks

Reflecting and looking at my journey in a positive light has been a fundamental practice for cultivating a positive outlook and a winning entrepreneur mindset. I set aside some time each day to write down my achievements, even the small ones, and jot down what actions contributed to them.

I do record my setbacks as well but maintain focus on the valuable insights gained from those experiences. This not only tracks my progress but also serves as a source of motivation. When I encounter obstacles in the future, I can look back and see how far I’ve come and this tangible reminder of my growth can inspire me to keep pushing forward with determination and confidence.

Harry Morton, Founder, Lower Street

Always Be Networking (ABN)

Network and Keep an Open Mindset

In the relentless pursuit of growth, I have become intentional in networking. I cannot emphasize the wonders networking can do. I maintain an open mindset and willingly engage in conversations, regardless of preconceived notions of how they might pan out.

Notably, the convenience of Zoom meetings has significantly expanded my network, allowing me to leverage it for business growth. Upon concluding a conversation, I often inquire if there are others they recommend connecting with, as industry ecosystems are typically close-knit. Establishing a supportive network has proven to be incredibly advantageous during unexpected moments.

This formula has truly worked for me in cultivating a winning mindset as an entrepreneur.

Eran Mizrahi, CEO and Founder, Ingredient Brothers

Learn from a Collaborative Competition Analysis

In cultivating a winning mindset, I’ve always believed in the power of collaborative competition analysis. As a budding entrepreneur, my team and I felt stagnant. We’d hit a plateau; innovation seemed elusive. Then it dawned on me—why not learn from the best in the business?

So we huddled and started studying our competitors, not to imitate, but to identify gaps and opportunities they missed, ideas we could innovate. As we immersed ourselves in this exercise, it was like watching an intricate dance, seeing patterns, predicting moves, learning the rhythm. The result?

Our mindset shifted; we felt invigorated, eager to develop fresh ideas. Our competitors weren’t merely rivals; they became our unwitting mentors. Through this collaborative learning, we molded a mindset focused on constant evolution and improvement, propelling us to new heights.

Derek Bruce, First Aid Training Director, Skills Training Group

I hope you found these insights valuable.

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joel libava

I'm The Franchise King®, Joel Libava. I help prospective franchise owners avoid bank account emptying mistakes.
For 23 years, I’ve been showing people how to make smart, informed decisions on franchises to buy, and I can help you, too!
P.S. I'm not a franchise consultant/broker.

Straightforward Advice
Joel, thank you for taking the time to speak with me yesterday. It was refreshing to finally speak with someone in franchising who dishes out straightforward, candid advice. You provided me with some insightful ideas that I'm giving a good deal of thought and consideration to. I look forward to speaking with you on our next consultation call."
- John Timmins, Columbia, South Carolina
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