Ep06 Brian Cressey, CEO, and Venture Capital Pioneer: Leadership Development

HOST: Ovi Vasquez, author of six books, and National Inspirational Keynote Speaker. Born and raised in rural Guatemala off-the-grid, worked for Apple, Tesla, Salesforce, and Uber. Learned English in two years, graduated from high school in three years, earned a bachelor's in management, in two years. He is a TEDx speaker and a social entrepreneur. 

GUEST: Brian Cressey, CEO, One of the nation's most influential business minds and investors, Bryan Cressey is a pioneer in Venture Capital and Private Equity. He co‑founded four of the most successful Private Equity firms in the United States. His investments and firms have produced exceptionally high returns for the past 40 years. Bryan has appeared in countless publications including Fortune, Harvard Law Today, the New York Times, Chicago Tribune, Crain's Chicago Business, and was featured by Time magazine as one of America's Best. 

Find our guest at:  https://www.bryancressey.com
Find our host at: https://www.ovinspires.com

Keywords  
entrepreneurship, strengths focus, mistakes as teachers, win-win mindset, positivity, eye contact, passion pursuit, college value, trade skills, victim mentality, optimism, venture capital, leadership traits, impatience in CEOs, life appreciation  

Summary  
Venture capital veteran Brian Cressy shares his unconventional path from a middle-class Seattle upbringing—marked by asthma, part-time jobs, and a year off college—to Harvard grad school and 40+ years building companies. In this engaging interview, he reveals counterintuitive success principles from his book *Be a Winner*: focus on strengths not weaknesses, learn from mistakes, create win-win outcomes, and maintain prolonged eye contact with positivity. Cressy urges high school and college students to pursue passions, consider college or trades, and reject victim mentality, emphasizing that early choices (ages 15–25) shape lifelong success.  

Takeaways  
* Great entrepreneurs improve strengths, not weaknesses—like Elon Musk or Jeff Bezos.  
* Mistakes are the best teachers; embrace them to accelerate growth.  
* Create win-win solutions—help others win and you’ll succeed bigger.  
* Maintain longer eye contact + genuine smile = instant trust and likability.  
* Positivity wins—approach people and challenges with enthusiasm.  
* Pursue what comes easily and passionately; college or trade school both lead to opportunity.  
* Victim mentality blocks success—go for it; the world is waiting.  
* Work part-time in college to stay balanced and prioritize effectively.  
* Impatient, fast-driving CEOs often outperform cautious ones (except surgeons!).  
* Ages 15–25 set your life trajectory—invest wisely in this decade.  

Titles  
* Be a Winner: Life & Business Lessons from a Venture Capital Legend  
* Strengths Over Weaknesses: The Entrepreneur’s Playbook  
* From Conveyor Belts to Harvard: Brian Cressy’s Success Blueprint  

Sound bites  
* “Mistakes have been my best teachers, even better than professors.”  
* “Great entrepreneurs don’t work on improving their weaknesses—they improve their strengths.”  
* “Be a win-winner: want the other person to win as well.”  
* “Positivity wins. Positivity makes great things come true.”  

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