• CEO coaching impact at Rydel → ex-CEO facilitator drove future-only focus, defined 8 KCIs tied to a 2031 revenue goal; owners present progress tomorrow

• Org alignment → mitigate siloed thinking as team scales (3 → 120 relationships), assign single-threaded KCI owners, and demand outcome-focused, data-backed cases

• Marketing leadership → new head prioritizes reliable data, base ad-spend momentum, and annual ROI thinking; December 19 staffing gap forces ad budget decision

• Alternative considered → split stations but run between each to simulate fatigue; consensus leans to true solo baselines first

• Capability clarifications → Amer can complete 1,000m ski/row by pacing vs intervals; confidence-building needed via measured tests

• Role split in race → teams rarely go 50/50; align to strengths (e.g., sled push load feasibility), and choreograph transitions together

• Performance goals → stretch: top 25; sub-60 min likely unrealistic given current run pace; use Ottawa trial to set aggressive but real targets

• Ottawa trial → Feb 15 in-person dry run to test pacing, transitions, and failure points safely; highest learning ROI vs individual practice

• Pairing model → Adel matched with retired ex-CEO (Crayola/Hallmark) via profile of stage, personality, and challenges; 2 full-day team sessions/year

• Facilitation craft → future-only framing with explicit yes from each attendee; redirected any past-focused remarks on the spot; met 1:1 at lunch to vent/close loops

• Talk-time split → ~25% facilitator, 75% team; brief teaching blocks (~20 min) + moderated discussion

• Intake & agenda → anonymous prework surfaced strengths/weaknesses → day focused on defining top initiatives to “deserve” 2031 revenue goal

• KCI outcome → group debated 17 → 8 KCIs; each KCI has a single owner accountable for orchestration across silos; progress review meeting is tomorrow

• Decision hygiene → facilitator stayed neutral, pressed for objective business value, and required owners to translate passion into cross-functional outcomes

• Relationship explosion → management grew from 3 to 16; interaction lines grew 3 → 120 (N*(N−1)/2) → more conflict/coord needs

• Whole-thinking lens → consider each object’s relationships to all others, not only “my function vs the thing”

• Meeting mechanism → everyone pitches priority initiatives; group selects few; single owner quarterbacks cross-functional execution

• Strong-but-timid ideas → owners expected to self-advocate; light prompting on outcomes; “natural selection” if the case lacks clarity

• Emotional spikes → facilitator acknowledged care, insisted on translation to business value; did not match energy; kept room grounded

• Hiring journey → struggled to find autonomous marketing owner; new leader from a different industry is working due to depth on metrics + ownership

• Data discipline → focus on fewer, reliable, raw data points that tell a coherent city/trade/lead-cost story; avoid noisy inferred metrics

• Spend momentum → maintain base ad spend in off-season to preserve algorithm learning; annual ROI > monthly; educate franchisees at network scale

• Stakes ↑ → guidance affects 30+ owners; requires taking stands with clear why

• Seasonal wrinkle → Dec 19–early Jan sales capacity near-zero; must adjust ad budgets to avoid unserviceable lead inventory vs losing algo momentum

• Project management gap → difficulty isolating bottlenecks from noise; risk of over-involvement; needs sharper owners, milestones, scorecards, comp linkage

• Solver addiction → urge to fix everything reduces team self-advocacy; practicing boundaries to let owners own outcomes

• Definitions matter → deepen rigor on integrity, responsibility, accountability; “how” now outweighs “what” at scale

• Identity vs results → over-attached to monthly sales; learning to accept short-term dips to grow managers and systems

• Anxiety management → hired PA (Ben) for 2–3 hrs/week as prioritization sounding board; structured check-ins, guided questions, RICE scoring to de-conflict urgency vs impact

The meeting begins with Austin introducing Devon Thomson, the VP of StudentWorks, as a highly capable and humble leader. The group engages in some friendly banter and reminiscing about past trips and events.

John asks Devon to provide an update on his role and the progress of StudentWorks since they last spoke, which was likely around 3-4 years ago. Devon shares that the company has grown significantly, with the painting and window cleaning divisions now generating $44 million in revenue, up from $28 million previously. He highlights the launch of a new polymeric sanding service that has been a major growth driver.

Devon explains that a key focus has been doubling down on coaching and training for their junior coaches, with weekly calls and a coaches retreat to help them improve their sales, recruiting, and leadership skills. This has led to significant improvements in operator averages and overall business performance.

John raises concerns about the financial literacy and profit tracking of some StudentWorks operators, noting that there can be a significant gap between their perceived and actual earnings. Devon acknowledges this challenge and discusses the efforts to provide more financial education and accountability, including bringing in outside experts to help operators better manage their finances.

The group delves into the nuances of effective coaching, discussing the importance of maintaining a positive, encouraging mindset rather than a moralistic or judgmental approach. Devon shares insights on how he and the StudentWorks team work to keep their coaches focused on being their operators' biggest cheerleaders and supporters.

Amer asks Devon about his personal accountability structures, such as working with a life coach, mastermind group, and therapist, as well as the role his fiancée plays in keeping him centered and focused on his values.

In the final segment, Austin and Devon discuss the dynamics of coaching relationships, including the potential need to transition to new coaches or roles as both the coach and the operator evolve. Devon shares his perspective on how he has adapted his own role and responsibilities as StudentWorks has grown.

Amer, Austin, and John engage in casual conversation, discussing Amer's Airbnb accommodations and the structure of Amer's regular group meetings, which involve sharing updates on business, finances, and personal life, as well as dedicated "opportunities" and "challenges" sessions.

Austin seeks John's advice on optimizing his capital allocation between paying down his mortgage and investing in the stock market. They discuss the nuances of mortgage interest rates, investment returns, and the importance of considering investment time horizons and valuation metrics like the Shiller P/E ratio.

Austin shares information about a unique mortgage renewal process in Canada that allows for lump sum payments to the principal, which could enable him to strategically time large mortgage paydowns.

John and Austin discuss the importance of thoroughly understanding the assumptions and valuation metrics used in syndicated real estate investment opportunities, rather than relying solely on the recommendations of others.

John shares anecdotes and insights about the joys and challenges of parenting his young son, including sleep training, introducing solid foods, and engaging in playful interactions.