“Only in YPO”: a Lifeline for Young CEOs

For young CEOs at the helm of companies, the role can often feel isolating. However, groups like the Young Presidents' Organization (YPO) and the Entrepreneurial Organization (EO) offer a lifeline, providing support, education, and unparalleled networking opportunities.

Early in my operating career as CEO of Bridgevine, my board recommended that I join YPO. I hadn’t heard of YPO, so I did some quick research and thought it could be helpful. I was lucky to have an incredible board whom I respected immensely, including Pat Welsh, Tom Wasserman, Ray Oglethorpe, and Ted Leonsis, and their endorsement of YPO spoke volumes about the organization’s credibility and the value it provides. Since joining in 2007, I’ve benefited beyond measure.

Based on my personal experience in YPO, here are some compelling reasons why joining YPO could be one of the best decisions a young CEO can make. There are other organizations out there, but I’m partial to YPO based on my own experience. Consequently, the following will refer to YPO specifically:

1) Peer Support

Leadership, especially at the CEO level, can be a solitary path. Decisions on personnel, strategy, and product expansion when you are a venture-backed company can be daunting. Organizations like YPO create a community of peers dealing with similar challenges. This community becomes a vital support system, offering both professional guidance and personal empathy, crucial for navigating the complexities of executive management. With 35,000 CEOs in YPO, there are industry peers of all sizes, not to mention VC, PE, and entrepreneurs who have sold companies that you can tap into to get objective advice.

2) Holistic Purview

YPO appreciates that being a CEO isn’t just about managing a business; it involves balancing personal life and family too. The organization provides resources and learning across these key areas, ensuring that leaders grow not just as executives, but as people. Not to mention the importance of involving your spouse and children in the organization. In my case, YPO became a core part of my children’s upbringing as they met great people, participated in awesome events, created great friendships, met cool celebrities, and traveled to places like the Bahamas, Sea Island, and Denver. YPO also has a program for young adults called YNG, focused on developing professionalism for 18- to 30-year-olds.

3) The Power of Forum

Arguably the most cherished aspect of YPO is the Forum—a small, intimate group of members who meet regularly to discuss issues deeply and confidentially. My own forum (thanks Brad, Mark, Roger, Brian, and Matt!) has become a trusted circle of friends, advisors, and confidants. The bonds formed here often last a lifetime and are foundational to both personal and professional growth. We meet once per month for 4–6 hours and discuss both the successes and challenges of our business, personal, and family lives. We are all deeply inquisitive and have an annual trip that either goes behind the scenes of a company or is facilitated by a professional around topics like organization, AI, legacy, etc.

4) Global Network

The broad network of over 35,000 CEOs globally adds an expansive dimension to membership. This diverse network opens global business opportunities and insights into international markets, invaluable to any growing business. Whenever I visit a city abroad, or a location I am not familiar with, I reach out to the local YPOers for advice.

5) Exclusive Interactions

YPO members have the unique opportunity to meet and learn from leading business figures and world dignitaries, including presidents and prime ministers. These interactions can provide profound insights and open doors that are typically beyond reach. A few names of speakers at YPO include George Bush, Tony Blair, Nelson Mandela, the Dalai Lama, and one of my favorites, Ivan Duque Marquez, the ex-president of Colombia.

6) Diverse Education

The educational opportunities within YPO are vast, covering everything from human resources and artificial intelligence to strategies for selling a company. This learning is tailored to the needs of CEOs and delivered in formats that respect the time constraints of busy executives. The education happens in a variety of ways, including video calls, incorporated into forum retreats, or intense weeks attending classes. There are literally thousands of learning experiences offered each year.

7) Unique Experiences

One thing I love about YPO is that it is a member-run organization, and it is run by highly competitive and successful people. This group loves unique experiences that you can’t get elsewhere, “Only in YPO.” Members run these events, which I have done several times, and their goal is to provide a remarkable experience. A few of my favorites:

  • A massive social event with 1,000 of my closest YPO friends at the Hagia Irene (an ancient Byzantine church) on the Bosphorus in Istanbul

  • A family event in Atlantis, Bahamas, where my kids met several incredible friends, coupled with the presence of Caroll Spinney, puppeteer of Big Bird and Oscar the Grouch

  • Exclusive seats at Wimbledon

  • A couples weekend at the Aspen Institute, staying at the Little Nell

  • Flying to the USS Theodore Roosevelt in an undisclosed location for a 24-hour stay alongside 5,000 of our finest service members, just weeks before their deployment to Iraq.

In Summary:

Membership in YPO is not just about the costs; it’s about immense returns. Many members report a significant return on investment, often quantifying it as 10-to-1, through gains in knowledge, connections, and advice that directly impact their company’s bottom line. Between the education, seminars, and access to experts, I would say there is a 20-to-1 return.

YPO offers young CEOs a platform that propels not only their companies but also their personal development. The range of benefits—from business growth, personal development, unique experiences, and lifelong friendships—makes membership a valuable investment.

In conclusion, for any young CEO looking to expand their horizons while receiving support in their personal and professional life, YPO and EO offer a complete package that is hard to match. YPO uses the moniker “Only in YPO,” which sums up the unique and compelling value proposition. Every young leader should consider these organizations as a key part of their growth strategy

Vinny Olmstead

Managing Partner

Vinny holds the position of Co-Founder and Managing Partner at Vocap Investment Partners, operating from the Vero Beach office. His portfolio includes serving on the board of Apollidon Learning, Harness, Soundstripe, and TimeDoc. He has previously held board positions in companies such as YourCause, Food52, Vydia, Sundrop Mobile, amongst others. Furthermore, Vinny plays a pivotal role as a board member for the Investment Advisory Committee for the $200B pension fund for the State of Florida.

With an impressive career spanning more than 25 years, Vinny brings a unique mix of investment, operational, and strategic expertise. This is further enriched by his entrepreneurial experiences that started during his teenage years, thereby extending his professional insight to more than three decades. Before joining Vocap, he led as the CEO of Bridgevine, an ad technology company renowned for customer acquisition, featured in the INC 500/5000 list for six consecutive years and eight total years.

Vinny's earlier professional pursuits include serving as VP of Corporate Development at 360networks, a publicly-listed fiber optic telecom company. He also accumulated eight years of consulting experience, including a four-year stint as a Partner at Mercer Consulting, a division of Marsh McLennan, and with KPMG Peat Marwick. His career began with two years at Coopers and Lybrand providing audit and tax advice.

In addition to his corporate roles, Vinny serves on the board of the Distinguished Lecture Series and the Southeast board of YPO Gold, a subsequent stage of the Young Presidents Organization. His academic credentials include an MBA & MHS (Master of Health Science) from the University of Florida and a BS in Accounting from Flagler College. When he's not working, Vinny loves exploring exotic locations with his wife and three kids, and enjoys watching and playing tennis.

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