Organizational Leadership Series with Danny Boockvar, President, Five Iron Golf

Five Iron Golf & Navigating a Non-Linear Career: A Discussion with Danny Boockvar

Key Concepts:

• Organizational Culture: Building a strong, intentional culture focused on purpose, praise, and potential.
• Franchising: Leveraging a franchise model for rapid, capital-efficient expansion.
• Non-Linear Career Path: Embracing risk and pivoting across industries based on personal fit and opportunity.
• Indoor Golf Market: The growth and potential of indoor golf as both recreation and entertainment.
• Dunbar’s Number: The cognitive limit to the number of people with whom one can maintain stable social relationships, impacting organizational structure.
• Product-Market Fit: The degree to which a product satisfies market demand.
• GLP-1s: Glucagon-like peptide-1s, a class of drugs impacting the weight loss industry.

I. Introduction & Background

The event, hosted by the Reuben Mark Initiative for Organizational Character and Leadership at Columbia Business School, featured Danny Boockvar, President of Five Iron Golf. Traci Rosenthal of the Reuben Mark Initiative introduced the speaker and moderator, Chuck Dodge, a CBS student and member of the CBS Golf Club. A complimentary 30-minute session at any Five Iron Golf location in New York City was offered to attendees who signed in. Danny Boockvar’s career spans diverse industries including the NFL, New York Cruise Lines, Girl Scouts of America, and Weight Watchers, demonstrating a pattern of growth-focused leadership. He previously served as President of Thrasio, a billion-dollar digital consumer goods company.

II. Danny Boockvar’s Career Trajectory

Boockvar’s career path is characterized by deliberate risk-taking and a willingness to deviate from traditional expectations. Despite earning a law degree from Penn Law School, he abandoned a career at Simpson Thatcher & Bartlett to join craftshop.com in 1999, an early arts and crafts e-commerce venture. While the company failed within six months, Boockvar considered it a pivotal learning experience. This decision marked the beginning of a non-linear career, moving from legal roles to sales and business development within the burgeoning internet boom. He emphasized that his career wasn’t a straight line, but a series of choices driven by personal fit rather than prestige.

A key turning point was joining Weight Watchers, a decision initially met with skepticism from his network. He rose through the ranks, eventually leading the East region at age 32, despite lacking prior management experience. He attributed his success to the faith placed in him by CEO Linda Huett and his ability to connect with the company’s mission. He spent 10 years at Weight Watchers, overseeing its public offering and international expansion. Boockvar highlighted the importance of understanding one’s financial needs and risk tolerance when pursuing unconventional career paths.

III. Leadership & Culture at Five Iron Golf

Boockvar described Five Iron Golf’s culture as “irreverent” and “fun,” mirroring the brand’s identity. He emphasized the importance of intentional culture building, particularly as the company scales. He outlined three key principles: Purpose, Praise, and Potential (the “3 Ps”). He stressed the need for a cohesive senior leadership team, avoiding “clusters” that can hinder collaboration and morale. He also referenced Dunbar’s Number, noting that organizational loyalty shifts as companies exceed approximately 150 employees, requiring deliberate efforts to maintain cohesion.

He highlighted the importance of understanding the core business and layering on complementary offerings, such as the addition of duckpin bowling to enhance event revenue. He also noted the value of a franchise model for rapid expansion, allowing for capital efficiency and leveraging local expertise.

IV. Five Iron Golf’s Growth & Strategy

Five Iron Golf currently operates over 40 locations globally, backed by investors including Callaway and Danny Meyer. Boockvar described the company’s growth as opportunistic, initially driven by a connection with a member who secured a location in Dubai. This success led to further expansion through franchising, particularly in the Middle East and Europe.

He highlighted the growing popularity of indoor golf, fueled by technological advancements and accessibility. He noted the potential of integrating wagering into the simulator experience, drawing parallels to FanDuel. The company is also exploring expansion into related entertainment offerings, such as mini golf, to broaden its appeal. He emphasized the importance of maintaining a strong core product while exploring complementary revenue streams.

V. The Future of Indoor Golf & Industry Trends

Boockvar believes indoor golf is a legitimate and growing market, with more indoor golfers now than outdoor golfers. He acknowledged that the recent performance of TGL (Tiger Woods’ indoor golf league) hasn’t been ideal, but doesn’t view it as a setback for the industry. He believes the fundamental appeal of indoor golf remains strong. He anticipates continued growth through franchising and strategic expansion into new markets.

VI. Advice & Closing Remarks

Boockvar offered two key pieces of advice:

• Business Advice: Continuously network and build relationships, as these connections often lead to unexpected opportunities. Take calculated risks and don’t be afraid to deviate from traditional career paths.
• Personal Advice: Find enjoyment in networking and building relationships, as this will be a valuable asset throughout your career.

He emphasized the importance of being open to unexpected opportunities and embracing a non-linear career path. He also acknowledged the role of luck and the importance of maintaining a positive attitude.

VII. Quick Fire Round Highlights

• Favorite Golf Course (Real Life): Riyadh Country Club
• Favorite Golf Course (Simulator): Bethpage Black
• Morning Tee Time or Twilight Round: Twilight
• Ryder Cup or Super Bowl: Super Bowl
• 2026 Masters Pick: Scottie Scheffler
• Hottest Take on Golf’s Future: Indoor golf is a real and growing trend.

Data & Statistics Mentioned:

• Five Iron Golf operates over 40 locations globally.
• Thrasio grew to a billion-dollar company in a short timeframe.
• Franchise multiples are higher than wholly-owned business multiples.
• More people now play indoor golf than outdoor golf.

Notable Quotes:

• “If you’re gonna work at Five Iron, prepare to be offended.” – Danny Boockvar, on the company’s irreverent culture.
• “I threw away a good law degree…and it was the best decision I ever made.” – Danny Boockvar, reflecting on his career pivot.
• “You’re meeting people you will work with in 20 years. You don’t know that yet.” – Danny Boockvar, emphasizing the importance of networking.

Synthesis/Conclusion:

Danny Boockvar’s presentation offered valuable insights into building a successful business, fostering a strong organizational culture, and navigating a dynamic career path. His story underscores the importance of embracing risk, prioritizing personal fit, and continuously networking. His leadership at Five Iron Golf demonstrates a commitment to innovation, strategic expansion, and creating a fun and engaging environment for both employees and customers. The discussion highlighted the growing potential of the indoor golf market and the importance of adapting to evolving consumer preferences.