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.

Austin shares that he has been struggling to manage his computer's storage and memory, often getting notifications about running low on space. The group discusses the differences between Mac and PC users in dealing with these types of issues.

Austin recounts his recent experience helping his sister buy her first new car. He describes the negotiation tactics used by the car salesperson, including the "four-square" method, and how he tried to advocate for a monthly payment his sister could afford.

The group discusses the pros and cons of buying a brand new car versus a lightly used one. Austin explains his preference for "newly used" vehicles to avoid the initial depreciation, while his sister wanted the certainty of a new car and warranty.

John shares that he recently spent time with people in their early 20s and made observations about how they rationalize their decisions, often justifying them after the fact rather than making choices purely based on principles.

John and Amer mention that they have additional private conversations on their Patreon group, the "Weekly Ballers", where they discuss more personal and financial topics that they don't want to share publicly.