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Rising from Adversity: Jonathan Beskin’s Journey to Success

Meet South Florida entrepreneur, philanthropist and author of the Wall Street Journal bestselling book ‘The Least Likely Millionaire: How to Succeed When Everyone Expects You to Fail’.

In a world often defined by negativity and naysayers, one man’s remarkable journey overcoming poverty, severe depression and anxiety including being hospitalized both as an adolescent and an adult for mental illness to creating a wildly successful company from a pre-revenue concept to $60 million+ in revenue in under five years without ever raising a penny - all as a side hustle while maintaining a full-time low paying job in financial services.

Beskin has used his success and notoriety to give to the community in South Florida and throughout the US. In 2022, Beskin donated 30,000+ pounds of food from his companies to Boca Helping Hands and then went on to donate over 18,000 units of full-sized women’s lifestyle products valued at over $450,000 to Junior Achievement of South Florida earlier this year. Additionally, a portion of all proceeds from SinglesSwag and Paradise Delivered are donated to the Breast Cancer Research Foundation and Feeding America, respectively.

Beskin’s journey began in a place of despair and uncertainty, marked by crippling anxiety and a complete lack of support from those around him. He faced bullying, abuse, and constant discouragement from family, peers, teachers, and even medical professionals. Despite the odds stacked against him, Beskin refused to give in to the negativity that surrounded him and instead decided to forge his own path to success.

‘The Least Likely Millionaire: How to Succeed When Everyone Expects You to Fail’ is not just a book; it is a chronicle of Beskin’s unwavering determination and a guide for others facing similar challenges. This memoir takes readers through the darkest moments of Beskin’s life and illuminates how he overcame toxic parenting, crippling anxiety, and a dearth of support to create a thriving business. The book also provides a blueprint for anyone looking to take business and creative ideas from concept to execution to hopefully the next least likely millionaire.

A notable concept that Beskin introduces in the book is that of a “healthy obsession,” a mindset that involves channeling crippling anxiety, catastrophization and other negative ruminations into positive pursuits like thinking about your business from every angle and even pre-empting what the competition is doing. Putting healthy obsessions into practice helped fuel his journey from the mental hospital to a place of financial success. He encourages readers to lean into their passions and remain tenacious in their pursuit of greatness, even in the face of adversity. Beskin’s real-world examples and key strategies offer practical insights and motivation for anyone striving to overcome obstacles and prove the critics wrong.

The book offers an inspirational narrative filled with actionable takeaways that empower readers to rise to new heights and challenge the negative voices in their lives.

‘The Least Likely Millionaire: How to Succeed When Everyone Expects You to Fail’ is available in Kindle format, Hardcover, and Paperback, and can be purchased on


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