Live coaching: scaling a multi-division events business past 30 people

Executive overview

United Fray runs three divisions — adult sports leagues, event production, and media — and hit the wall that most 30-person companies hit: processes lag behind growth, departments silo, and a CEO strong on vision but weak on execution discipline carries too much weight.

The core fix is cutting the unprofitable division, measuring efficiency against benchmarks, and investing in the five to seven people who will actually scale the business.

Growing your key people's skills is the highest-ROI move available to a 30-person company.

Business model and revenue split

• Three divisions: adult sports leagues (~35–40%), event production (~35–40%), media/advertising (remainder)
• All three united by expertise in experience design and the mission "making fun possible"
• A membership model is in early growth and becoming a fourth revenue stream
• Media distinguishes the company from competitors but carries the weakest margins

COVID recovery and the media decision

• COVID was an existential threat — the business is the antithesis of social distancing
• Media was acquired rather than built incrementally; overhead and legacy assumptions baked in from day one
• Advertiser revenue never recovered to the level the model required
• Decision made to shut down the entire media team — the hardest call in 13 years of running the company
• Framing: businesses don't fail by doing the wrong things; they fail by continuing to do the wrong things

The PETA factor and resource allocation

• PETA factor: the pain, energy, time, and attention a business line consumes beyond its P&L cost
• Running three businesses splits focus the same way dating three people does — no one gets full attention
• Shutting media freed cash, mental capacity, and leadership time for the two profitable divisions
• The 80-20 rule applies directly: concentrate resources on the lines generating operating profit

Organisational complexity at the 30-person mark

• Moving from 30 to 100 employees requires different skills than earlier stages — "pre-teen to teenager"
• Creative, sports, and events teams have different working styles; siloes form naturally and must be actively broken
• CEO is strong on entrepreneurial vision, weak on routine execution discipline — relies on senior team to bridge that gap
• Senior leaders are straddling operations and long-term planning simultaneously, which is hard to sustain

Shooting the dogs: a leadership framework for cutting

• Ernest Shackleton shot the expedition dogs to save the men — removing what consumed resources without contributing to survival
• Ask across the company: what projects, tasks, and expenses can be cut right now?
• The right question after a bad decision is not who to blame but what system was missing that let it persist too long
• Build a system to surface these decisions faster — confront brutal facts sooner, don't wait for the fog to clear

Growing people and efficiency metrics

• Invest in the five to seven key people in the company; their growth determines the company's growth ceiling
• Track three benchmarks quarter-on-quarter and against industry peers: revenue per employee, gross margin per employee, salaries as a percentage of revenue
• First-time managers default to hiring more people; the real issue is usually missing skills, inability to say no, or poor conflict management
• Give senior leaders P&L visibility and explain the why behind decisions — at scale, teams need to understand the reasoning, not just the directive

Customer experience leverage

• Only four root causes of customer service volume: bad product, bad service, oversold expectations, or weak FAQs
• With only two customer experience staff, improving self-serve FAQs now means the same two people can support a 3–4× larger member base
• Solve the root problem, not the bandaid — first-principles thinking applied to support tickets compounds into gross margin