McKenna Gaughan

Overview

McKenna Gaughan is Gary's ex-girlfriend whom he dated for 8 months in 2024 while living in Denver. They reconnected on May 17, 2025, after not speaking for several months. McKenna is likely working in hospitality or event services and may have experience with "Dom" work (possibly bottle service or similar nightlife hosting). She has an upcoming exhibition and might be considering relocating from Denver, potentially to Miami.

McKenna’s Conditions as of 2024-10-07

As of October 7, 2024, McKenna was navigating a significant set of chronic health conditions, which impact her daily life and career:

• Interstitial Cystitis
• Endometriosis
• Hypereosinophilic Syndrome
• Reoccurring Epstein-Barr Virus flare-ups
• Reoccurring Staph Infections
• Reoccurring Shingles
• Extensive Allergy List, specifically:
  • Foods (including celiac; gluten intolerance)
  • Animals (including cats and dogs)
• Compromised immune system
• Consistent muscle pain and weakness
• Severe muscle tension causing reoccurring migraines

These conditions mean she must manage complex health needs, dietary restrictions, and immune system challenges on an ongoing basis.

Background & Personal Details

• Former girlfriend of Gary Sheng (8-month relationship in 2024)
• Based in Denver (moving in with friends Serena and David at their duplex end of January 2026, reconsidering Brooklyn plans)
• Professional dominatrix working with high-profile clients
• Running successful anonymous podcast
• Creating multi-year art exhibition project with film and book components
• Previously worked in bottle service, which she reportedly did well with financially
• Extreme Work History: Worked 286 consecutive days without a day off in 2025 (updated from 238-day restaurant streak)
• Self-Education Background: Self-taught from 2nd grade through high school, always operated in sprint mentality

Professional Focus

• Dominatrix Work: Currently working as professional dominatrix with C-suite executive clients
• Client Profile: "Essentially they're all C suite executives and really high prices"
• Mentorship Aspect: "I'm essentially getting mentored by a lot of really amazing people" through clients
• Anonymous Success: Running successful anonymous podcast
• Art Exhibition: Major exhibition project postponed from 4 months to 2 years timeline
• Film and Book: Creating film (completed) and currently writing/designing book
• Financial Success: "Making more and working way less hours" after leaving restaurant job
• Business Model Change: Considering restructuring business model due to inability to showcase accomplishments publicly
• Oros Opportunity: Pablo's company finally received funding, potential consulting opportunity

Connection to Gary

• Met and dated in Denver during 2024
• 8-month relationship
• Period of no contact for several months after breakup
• Reconnected by phone on May 17, 2025
• Mental Health Insight: McKenna observed patterns in Gary suggesting potential hypomanic episodes during their relationship
• Protective Dynamic: McKenna describes herself as "doberman" - protective of Gary's energy and wellbeing
• Pattern Recognition: Noted Gary's cycle of depression → finding new passion → intense energy/little sleep
• Continued Care: Both explicitly express love and concern for each other's wellbeing despite separation
• Unique Understanding: McKenna's intimate knowledge of Gary's behavioral patterns provides valuable external perspective

Personal Insights

• Work-Life Realization: Worked 238 consecutive days without a day off - "totally survival" mode
• Project Management Discovery: "I have never been in a long-term project in my life" - always operated in sprints
• Educational Background: Self-taught from second grade through high school, would cram semester curriculum in two weeks
• Sprint Mentality: "I would accomplish what most people accomplish in a year in three months or under"
• Health Challenges: Recovered from 2.5-month illness (laryngitis, strep throat, sinus infection) after intense 2025 work streak
• Social Obligations: Bridesmaid in 5 weddings in one year
• Relocation Plans: Moving in with Serena and David (duplex) to lower costs; no strong calling for any specific location; reconsidering Brooklyn
• Self-Awareness: Learning to slow down after intense workaholic phase

Mutual Connections

• Raz/Razz: Mutual friend currently in NYC, trying to immigrate to US, business struggling to recapture 2022 success
• Ken: Mutual friend who got engaged, expanded his company with new hires, occasionally hosts Gary in Austin
• Pablo: McKenna's best friend, founder of Oros which finally received funding after 1.5 years
• Serena and Rachel: McKenna's best friends mentioned alongside Pablo
• Danielle: Friend getting married, McKenna serving as bridesmaid

Potential Collaboration Areas

• No direct collaboration currently planned
• McKenna considering consulting role with Pablo's Oros (with protective contract terms)
• Gary processing McKenna's mental health observations for self-awareness
• Mutual support system despite ended romantic relationship
• McKenna's high-profile network through dominatrix work could offer unexpected connections
• Both navigating significant career transitions with lessons to share

Initial Interaction Highlights

• Friendly, casual catch-up conversation after period of no contact
• Gary shared updates about his new role with Alpha Schools and why it's a good fit
• Gary mentioned the corporate culture values open communication and "uncomfortable truths"
• Gary suggested McKenna might be successful in Austin and offered to host her for a visit
• McKenna appears focused on an upcoming exhibition and potential career decisions

Interactions

• 2024: 8-month relationship in Denver
• Early 2025: Period of no contact
• 2025-05-17: Phone call reconnection while Gary was in New York for meetings. Gary shared updates about his new role at Alpha Schools and they discussed McKenna's current projects and potential future plans.
• 2025-11-07: Deep conversation while Gary attended Rome Catholic conference. McKenna expressed concern about potential hypomanic patterns in Gary's behavior based on email communication and past observations. She connected his religious awakening to depressive episode patterns and advised conscious management of high-energy periods. McKenna shared major life updates including dominatrix work with C-suite executives, leaving exhausting sushi restaurant job after 238-day work streak, successful anonymous podcast, 2-year art exhibition project with film and book components, and planned partial relocation to Brooklyn. Both expressed continued love and care for each other's wellbeing despite romantic separation. Discussion included updates on mutual connections (Raz in NYC, Ken engaged, Pablo's Oros funded).
• 2026-01-04: Video call to resolve 1099 tax filing for $1,100 Gary sent via business account. Agreed to file as "marketing consulting" with 50/50 tax cost split. Gary shared new Austin living situation (housemate on Huberman podcast team) and Vegas family holidays. McKenna recovering from 2.5-month illness after working 286 consecutive days in 2025; moving in with Serena and David to lower costs; spent NYE with client couple in Florida. Both discussed prioritizing financial contracts and protecting energy in 2026. McKenna affirmed Gary's value ("energy of a thousand suns"). Expressed continued love and care.

Next Steps

• Gary sending 1099 via QuickBooks in next few days
• Split tax cost 50/50 on the $1,100 (filed as "marketing consulting")
• McKenna moving to Serena and David's duplex end of January 2026
• Both prioritizing financial contracts and energy protection in 2026
• Maintain caring connection with healthy boundaries

Transcripts

Transcript ID	Date	Summary
2025-05-17-mckenna-gaughan-conversation-summary	2025-05-17	Phone call reconnection discussing life updates and potential opportunities in Austin
2025-11-07-gary-mckenna-mental-health-concern-life-updates	2025-11-07	McKenna's mental health concerns about Gary's patterns and life updates on dominatrix work and art projects
2026-01-04-mckenna-gaughan-tax-alignment-life-updates	2026-01-04	Tax filing alignment (1099 for $1,100 as marketing consulting) and life updates on new living situations