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The Least Likely Millionaire

Could you succeed in the highly competitive business world when no one believed in you, anxiety and depression were crippling you, and you had no idea what you were doing?

Be inspired to be more courageous in both your life and career.

What does success look like to you?

No stranger to adversity and feeling “locked out” of entrepreneurship, self-made serial entrepreneur Jonathan Beskin shares how he channeled his obsessive tendencies and mental health struggles into a business that would change the course of his life forever.

His first company, SinglesSwag.com, went from a pre-revenue idea launched with $2000 in his savings to over $60 million in revenue in under five years.

Now an investor in multiple private companies and startups as well as a leading expert in digital advertising, Jonathan has twice been featured in the prestigious Inc. 5000 list and gives back to the business community by mentoring and coaching aspiring entrepreneurs.

An Inspirational Journey

The Least Likely Millionaire is a triumphant memoir of overcoming crippling anxiety, toxic parenting, and a total lack of support to start and build a wildly successful company in spite of the naysayers. It’s a tale of resilience, of passionate tenacity that every underdog needs to hear.​

  • Filled with actionable takeaways & real-world examples that will help anyone overcome obstacles and achieve success.
  • Discover Beskin’s secret of leaning into a “healthy obsession” to fuel your quest for greatness.
  • The Least Likely Millionaire will inspire you to rise to new heights and empower you to prove the critics wrong.
  • Verne Harnish

    VERNE HARNISHFounder | Entrepreneurs’ Organization (EO), Author of Scaling Up and Mastering the Rockefeller Habits

    "Beskin's honest, raw, unfiltered story tells it like it is. Against all odds, including scaling through a pandemic, he takes readers on a journey of success, unexpected. The lessons he imparts can help any entrepreneur scale their business."

  • Dr. Marshall Goldsmith

    Thinkers50 #1 Executive Coach | New York Times bestselling author of The Earned LifeTriggers, and What Got You Here Won’t Get You There.

    “If you're looking for a book that will motivate you to reach for the stars, this is a must-read. Jonathan Beskin is a gifted storyteller with a wealth of wisdom to share. With valuable lessons on how to thrive in the face of adversity, this book is for anyone looking to succeed against all odds and unlock their full potential.”

  • Mike Calhoun

    Founder | Board of Advisors.com, GoCEO.com & MikeDrop.com

    "Beskin fortifies that power comes from pain, success comes from struggle and clearly that hard-work before smart-work is the sequence to getting ideas, concepts, products and/or services to the stage of viability, ultimately enabling a real opportunity for scalability. I'd prescribe multiple reads or listens and pray your competition doesn't."

  • Eric Malka

    Founder | The Art of Shaving & Ingredients® Wellness

    "Beskin’s redemption tale reminds us that using the pain of adversity to our advantage can be a powerful competitive advantage. His writing will help readers identify what’s holding them back in business and in life and why societal conventions and norms are meant to be defied. The Least Likely Millionaire illustrates what you can accomplish when you refuse to believe the things that people tell you are necessary to be successful.”

  • Yosef Martin

    Founder | Boxycharm (sold to Ipsy for $500M)

    "The enemy of every entrepreneur is comfort. In The Least Likely Millionaire, Beskin reminds us that not having a safety net is exponentially more valuable than having one. With no Plan B, you have no choice but to make success happen. Jonathan's story of refusing to let failure have the last word speaks to the underdog in all of us."