From Bankruptcy to Board Games: Igor Vainshtein’s Journey to Entrepreneurial Resilience

Entrepreneurship is glorified, but few talk about the repeated failures, financial struggles, and self-doubt that come with it. Igor Vainshtein knows the highs and lows of entrepreneurship better than most—after moving to Australia with nothing, he built multiple businesses, only to lose everything multiple times. Through years of trial and error, he cracked the code on resilience and eventually sold his golf simulator company for a major exit. Now, he’s bringing his lessons full circle with a board game designed to teach entrepreneurs how to navigate real-world business challenges.

In this episode, Igor shares his rollercoaster journey of business success and failure, the lessons he learned from hitting rock bottom multiple times, and how his new game EntrepreneurPolly is gamifying the realities of entrepreneurship. If you've ever faced setbacks in business, this episode is a must-listen.

Key Takeaways:

• Fail Fast, Learn Faster: Igor explains how he lost everything multiple times before finally building a business that led to a successful exit.

• The Power of Resilience: Learn how Igor developed an unshakable mindset, treating business challenges like a game—one that can be won with persistence.

• From Bootstrapping to Selling a Business: How Igor went from near bankruptcy to scaling and selling a golf simulator company to a major industry player.

• Entrepreneurship as a Game: Discover why Igor created EntrepreneurPolly, a board game that mimics the real-life struggles and wins of business owners.

• Why Most Businesses Fail: Igor breaks down the biggest mistakes entrepreneurs make and how to avoid them by developing a problem-solving mindset.

About the Guest:

Igor Vainshtein is a serial entrepreneur, best-selling author, and creator of Entrepreneurpoly, a board game that brings the real-world challenges of entrepreneurship to life. His journey—from immigrating from the USSR to Australia at age 10, launching his first business at 17, and later expanding to the USA—has been defined by resilience, adaptability, and a passion for turning ideas into reality.

With experience spanning e-commerce, technology, manufacturing, and golf, Igor has built and scaled multiple ventures, including a golf-focused business that grew 10x during COVID and successfully expanded to the U.S. in 2021. Now, he’s innovating again with Golftrak.app, helping golfers improve their game using only their iPhones.

A global entrepreneur with firsthand experience navigating international markets, Igor understands the nuances of scaling businesses across borders. He thrives on strategy, continuous improvement, and sharing the hard-earned lessons of startup life—many of which are woven into Entrepreneurpoly, a game that educates and inspires future business leaders.

As a speaker and podcast guest, Igor delivers relatable stories, practical insights, and an infectious passion for entrepreneurship. Whether discussing business strategy, global expansion, or the parallels between golf and startups, he inspires others to take bold steps toward their dreams.

Links:

https://www.linkedin.com/in/igorvainshtein/

https://www.igorvainshtein.com/

Fast Five Questions:

1. If you woke up and your business was gone, you have $500, a laptop, a place to live, and food, what would you do first? “Start consulting immediately—helping entrepreneurs avoid the mistakes he’s made.”

2. What is the biggest mistake that you have made in business? “Ignoring gut instincts and waiting too long to pivot, even when the warning signs were obvious.”

3. What is a book that you would recommend? “Shoe Dog by Phil Knight—the raw, unfiltered journey of building Nike from scratch.”

4. What is a tool that you use every day that you would recommend? “LinkedIn—for networking, business insights, and building connections that open doors.”

5. What is your definition of freedom? “The ability to spend time doing what he loves, with the people he loves, while having financial security and flexibility.”

About Jeff:

Jeff spent the early part of his career working for others. Jeff had started 5 businesses that failed before he had his first success. Since that time he has learned the principles of a successful business and has been able to build and grow multiple seven-figure businesses. Jeff lives in the Austin area and is actively working in his community and supporting the growth of small businesses. He is a board member of the Incubator.Edu program at Vista Ridge High School and is on the board of directors of the Leander Educational Excellence Foundation

Connect with the Freedom Nation podcast at https://freedom-nation-podcast.captivate.fm/

Connect with Jeff:

Instagram: https://www.instagram.com/freedomnationpodcast/

Twitter: https://twitter.com/JeffKikel

LinkedIn: https://www.linkedin.com/in/jeffkikel/

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