Know about John Cerasani – Sports and Tech Entrepreneur

By | June 3, 2024

John Cerasani is a former football player who played for the University of Notre Dame and Northwestern University. He is an entrepreneur and owns a brokerage firm. He is also an author, venture capitalist, podcast host, and manager of Glencrest Global, a Chicago-based hedge fund.

John Cerasani is an entrepreneur, podcast host, and venture capitalist

John Cerasani is an entrepreneur, podcast host, and venture capitalist

Early Life

John Cerasani was born on December 3. The year of his birth is unknown.

He attended the University of Notre Dame from 1995 to 1997 to study business management. Then, he went to Northwestern University to get a Bachelor's degree in Education and Social Policy.

Cerasani grew up in Chicago, where his passion for football led him to play for Notre Dame and Northwestern University during his college years.

When it comes to his family, John's father is Tom M. Cerasani, his mother is Joan Cerasani, and he has a brother named Thomas A. Cerasani. Thomas is a social studies teacher, football coach, and assistant dean.


John started his professional career as a consultant for Great-West Healthcare. After that, he worked as area vice president for Arthur J. Gallagher, where he consulted higher education clientele on implementing employee benefit programs.

From 2005 to 2015, John acted as the president of Northwest Comprehensive Inc., where he worked with mid-sized employers on the implementation and brokerage associated with employee benefit programs.

Early Retirement Fund

Cerasani started an insurance company and exited successfully in 2015, building retirement wealth at age 37. This fact makes him around 46 years old as of 2024.

After exiting his company, John planned on retiring for good and spending the rest of his life on a small island drinking margaritas. However, he made a few bad wealth-related decisions and realized he had much more to give the world.

Glencrest Global

Moving on, John became a serial entrepreneur, investing in several sports, gambling, and technology companies, including OSDB Sports, the Gaming Society, and Moneyline.

John Cerasani is the founder of Glencrest Global

John Cerasani is the founder of Glencrest Global

Driven by his business passion, Cerasani founded Glencrest Global in 2020, where he acted as the managing partner. Glencrest Global is a venture capital investment firm in Chicago, Illinois.

The firm invests in various sectors, including sports, leisure, gaming, food technology, SaaS, and more.


Besides managing multiple businesses, John Cerasani is an author and has published two books. His book "2000 Percent Raise" was published in April 2023.

The book tackles John's remarkable journey from quitting his regular job to focusing on entrepreneurship and his overall success and financial triumph.

Meanwhile, his book "Paid Training: Learn the Industry, Leave Your Job, Win On Your Own" emphasizes more about the power of perspective and courage. The book gives encouragement to people who seek a path beyond conventional careers.


John Cerasani also hosts his podcast "2000 Percent Raise." The podcast focuses on empowering listeners to achieve growth in their personal and professional lives.

John Cerasani is the podcast host for 2000 Percent Raise

John Cerasani is the podcast host for 2000 Percent Raise

John aims to help people think bigger, act bolder, and create exponential results. On his podcast, Cerasani invites different personalities such as athletes, entrepreneurs, celebrities, and industry insiders.

John often shares his journey and life experiences in the podcast, from leaving a secure job to generating retirement wealth.

Below Deck

During "Below Deck Sailing Yacht" Season 4, John Cerasani appeared in episodes 5 and 6 with his girlfriend Natalia, daughter Anastasia, son Jacob, and friends TJ and Lauren.

In episode 5, John's son was warned to keep his distance when using the eFoil on the water. Unfortunately, he crashed into John's friend TJ, resulting in the TV show's first serious guest injury.

Despite all the drama, John and his family had a great time on the yacht during their guesting, and he made a $23,000 tip for the crew.

Personal Life

John is an American, married to Natalia Miller. She has been an insurance broker at HealthMarkets since 2017. The couple have two kids, Anastasia and Jacob, 20 and 15, respectively.

Unfortunately, John and Natalia got divorced. John is now a full-time single dad. Recently, he took his kids on a trip to Maui, as shared on his Instagram account.

His net worth is estimated to be $50 million.

Official Links

Instagram - @johncerasani
Twitter - @johncerasani
LinkedIn - John Cerasani
YouTube Channel - John Cerasani TV
TikTok - John Cerasani

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