Meeting Summary: Career Strategy and Fractional Events Agency Discussion

Overview

Gary and Brooke met at a new Austin cafe to discuss career transitions, potential collaboration on a fractional events agency for tech startups, and the spiritual dimensions of their professional journeys. The conversation revealed both are navigating resistance from family about entrepreneurial paths while seeking to align their work with deeper purpose.

Key Topics Discussed

Alpha Schools Re-engagement Strategy

• Rome Conference Context: Gary attended a faith-based AI conference in Rome where Alpha Schools was prominently discussed across multiple education track sessions
• Strategic Opportunity: Planning to propose organizing a major education summit for mid-March 2026 (during UT spring break after SXSW)
• Brooke's Enthusiasm: "I would love to" - she noted Alpha had been hiring for events positions and Joe Liemandt reportedly needs help
• Gary's Hail Mary Approach: "Let's do a little Hail Mary. Either he bites or doesn't, it doesn't matter"

Fractional Events Agency Concept

• Business Model: Gary would handle lead generation and business development while Brooke manages execution and experiential design
• Target Market: Growing tech companies and startups in Austin that understand in-person experiences benefit recruiting and user acquisition
• Website Development: Planning to create site with interest form and 3 case studies relevant to startups
• Gary's Role Clarity: "People know me as someone that puts on great events. That's because I have good taste in people like you"
• Brooke's Ideal Structure: Seeking 3-4 consistent retainer clients rather than one-off projects for stability

Career Transitions and Existential Questions

• Gary's Spiritual Calling: "If I didn't have to worry about money, I think what I would do is I would probably write about spirituality. I'd probably be helping people that are sick"
• Recent Healing Work: Brought a family to pastor in Liberty, Texas who healed father's back pain, son's intrusive thoughts, and working on case of blindness from car accident
• Internal Resistance: Gary admitted to experiencing suicidal thoughts: "Sometimes I'm like this is just too much. I want to give up"
• Friend's Perspective: Friend told Gary he sees him "as an animal in a zoo cage" if he takes a 9-to-5 job

Brooke's Business Evolution

• Rewiring Approach: "I've been trying to rewire my nervous system... not knowing is like this unthinkable energy, but like rewiring it always works itself out"
• Shifting from People-Pleasing: Now asks "What's aligned for me?" versus old pattern of "choose me, choose me, I don't care"
• Proposal Standards: No longer accepting full-risk partnerships without guaranteed compensation
• Working at Sustainable Capacity: With underpaying friend, working at "80% capacity versus like 150%"
• Documentation Gap: Acknowledged not documenting case studies well: "I'm not good at that"

Family Dynamics and Scarcity Mindset

• Parental Pressure: Both face pressure from parents to get traditional jobs
• Brooke on Parents: "They believe in me. It's hard for them to doubt it because they're in fear... that's really scary to them"
• Gary's Parents: "They want me to get a nine to five" despite his entrepreneurial path
• Contrasting Energy: Brooke appreciates Gary's "expansive energy" versus the "scarcity mindset" from family

Divine Orchestration and Lessons

• Gary's Perspective: "I like to think that it's all been orchestrated in ways that I would never orchestrate myself"
• Lessons from Disillusionment:
  • Saw Catholic Church leadership as "kind of a mess at the upper echelons"
  • Witnessed billionaire (Joe Liemandt) as "very human" and flawed
  • Discovered Dr. Lael Alexander as "not always a liar, but regularly a liar"
• Pattern Recognition: Shared story of Lael having two children from affairs: "If you're willing to cheat on your wife, you're willing to cheat on anyone in any business"
• God's Direction: Believes God wants him "to be less dependent on anyone for my destiny"

Current Projects and Opportunities

• Healthcare AI Conference: Brooke developing proposal for October 2026 conference (200 people)
• Ultra Wellness Center: Collaborating with former partner Sarah on Dr. Hyman's marketing strategy in Berkshires
• Wildwood Film Project: Recently completed comedy event for Zachary's studio project
• Intermission Business: Brooke's events company getting referrals but needs more consistent structure

Professional Philosophy Alignment

• Purpose-Driven Clients: Brooke: "The humans behind the project is what drives me... when the human is wanting to really help humanity"
• Co-Creative Process: Gary: "I don't think the idea of self-making yourself is the right way... we're co-creative in the process"
• Collaboration Desire: Brooke: "I want to collaborate more because I don't like working in a silo"
• Faith Integration: Brooke asks God to "show me this person through your eyes" when struggling with relationships

Key Quotes

• Brooke: "If someone says no, then something else says yes"
• Gary: "If you're that unable to just set outcomes instead of hyper surveillance, that's just a reflection of how poorly managed your organization is" (about Alpha's tracking)
• Brooke on Gary's impact: "You're my biggest expander of 2025"
• Gary: "The intrusive thoughts for me have ramped up... but often that resistance is what almost always happens before breakthrough"
• Brooke: "It took me five years of being on my own to get there" (prioritizing her needs)

Action Items / Next Steps

• Friday 10:30am Meeting: Develop agency website with 3 case studies
• Alpha Schools Outreach: Await response to Gary's email about education summit
• Website Development: Gary to create static site for fractional events agency
• Case Study Documentation: Brooke to provide images and details for 3 relevant case studies
• Proposal Follow-up: Brooke to respond to healthcare AI conference opportunity

Strategic Insights

The conversation revealed both Gary and Brooke are at inflection points in their careers, seeking to balance financial sustainability with purpose-driven work. Their complementary skills (Gary's vision and connections, Brooke's execution and experiential expertise) position them well for the fractional agency concept. Both are learning to set boundaries with clients and family while trusting divine orchestration of their paths. The potential Alpha Schools summit represents both a practical opportunity and a test of whether past challenges can be transformed into future success.

Relationship Dynamics

The mutual respect and professional synergy is evident throughout. Gary acknowledges his events reputation comes from partnering with talented people like Brooke, while she credits him with expanding her business vision. Both provide each other with alternative perspectives to the "scarcity mindset" they encounter elsewhere. Their shared faith perspective and understanding of spiritual dimensions in business creates additional alignment beyond mere professional collaboration.