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ID:
2025-11-19-gary-david-kobrosky-career-spiritual-alignment
Participants:

Call Summary: Career Crossroads, Go-to-Market Strategy, and Faith-Tech Opportunities

Overview​

David Kobrosky and Gary Sheng reconnected after their October Yom Kippur conversation to discuss career paths, spiritual alignment, and emerging opportunities at the intersection of faith and technology. David shared his engagement news and fitness goals while providing strategic counsel on Gary's career decisions, particularly around a Perplexity opportunity versus independent consulting. The conversation revealed deep alignment on go-to-market strategies and potential collaboration on helping churches leverage AI for growth.

Key Topics Discussed​

David's Personal Updates​

Engagement and Life Changes​

  • Major News: "I proposed to Mikayla. So that happened, which is kind of a big deal"
  • Fiancée works at Bloomberg, keeps him informed on news headlines
  • Settling into more structured life post-engagement

Fitness Goal: Dunking a Basketball​

  • Specific Target: Need 5 more inches of vertical jump in 5-6 months
  • Weight Loss: "I need to lose about 10 to 15 pounds of weight"
  • Strength Goals: Increase squat from 225 to 315-350 range ("one and a half times body weight")
  • Accountability Strategy: "The future embarrassment of not being able to do it is driving me because I'm telling everyone about it"
  • Current Activity: Running a co-ed Volo basketball league team
  • High School Story: Nicknamed "Cobra" - coach said "You're the least talented player we're gonna take this year. But you're the biggest heart on the court"
  • Recent Setback: "I hurt my back though. I was deadlifting... I pulled something in my back"

Gary's Career Crossroads​

The Perplexity Opportunity​

  • Role: Developer Relations in San Francisco
  • Gary's Assessment: "I think generally my skill sets match up well in a developer relations type role"
  • The Disconnect: "It doesn't feel like any job spiritually makes sense. And I'm happy to unpack that. You're the first person that I've said those words to"
  • Honest Take on Perplexity:
    • "It's kind of a random company... among many other companies competing during this bubbly AI phase"
    • "I'm not going to lie. It's kind of a commodity too"
    • "If it went away, my life would not be different"
    • "It's going to be fine without me"

Alternative Path: Agentic Workflow Consulting​

  • Friend from Gauntlet AI cohort making good money consulting businesses
  • Gary's View: "As soon as I have one successful case study, it's just a lot easier to get referrals"
  • Flexibility Advantage: Allows for spiritual pursuits and church support
  • David's Counsel: Need "90% plus confidence" before going fully independent

Spiritual Fulfillment​

  • Current Joy: "I'm really enjoying supporting this one church a few hours away from Austin"
  • The Tension: "You can only help churches if you labor, though, if you don't have money coming in"
  • Recent Experience: Attended Faith & AI conference at Vatican in Rome

David's Career Evolution and Go-to-Market Philosophy​

Current Bevy Strategy​

  • New Focus: "I really want to spend three hours a day on setting up all of our go-to-market flows"
  • Working Hours: 11am to 6pm with morning writing time
  • Career Timeline: "In about 20 months from now, I will have hit my two years" at Bevy

Go-to-Market Insights​

  • Market Reality: "All these other channels getting oversaturated... The AI SDR for email outbound is solved"
  • Future Skills: "Being really good at go-to-market... is not going to go anywhere"
  • Key Differentiator: Need to be "marketing-savvy engineer or engineering-savvy marketer"
  • Channel Innovation Example: Reddit reply automation for SEO and qualified traffic
  • Community Dynamics: Explained why larger platforms win (parallel to Catholic Church's institutional advantages)

Long-term Vision​

  • Goal: "My dream is I make 200K minimum and I'm working 4 hour days"
  • Purpose: "So I can spend most of my time thinking about my worldview and writing and building a brand"
  • Options: Either find a channel to master and build product around, or start consultancy

Faith & Technology Intersection​

Vatican AI Conference Insights​

  • Gary's Observation: "A lot of risks of deferring to AI for spiritual matters. There can be utility at the same time"
  • Catholic Church Advantage: "Such an institution that it can host these convenings in a way that a very tiny denomination... would not be able to"
  • Rome Experience: Leveraging "ancient real estate... multi hundred year old university or Vatican City"

Church Growth Opportunity​

  • David's Insight: "Everything depends on membership. Membership's going down"
  • Value Proposition: "If you can solve the problem [of] membership going down... that's a big deal for faith"
  • Gary's Vision: "Own memetic space around faith and AI... Helping churches go to market with AI"
  • Market Size: "There's just literally infinite churches"

Strategic Advice and Decision Framework​

David's Question Framework​

  • "Is the reason that the Perplexity opportunity doesn't feel spiritually aligned because... what I'm doing doesn't have meaning?"
  • "Is it that it doesn't contribute to my overall mission?"

David's Counsel on Independence​

  • Preparation: "Ideally, you already have... three to six referrals, you already have the pipeline"
  • Timing: "Ideally, you just wait as long as you can"
  • 9-to-5 Benefits: "There's something nice about 9-to-5... no startup fee, no onboarding fee"
  • Flexibility Example: "I work from 11am to 6pm... I can do things in the middle of the day if I need to"

Accountability Partnership​

Mutual Goals​

  • Fitness: Both want to lose 10-15 pounds, David wants to dunk
  • Skills: Gary learning agentic workflows, David mastering go-to-market
  • David's Commitment: "Super down. We'll do that and we'll accountability for losing 10 pounds"

Key Quotes​

On Career and Purpose​

  • Gary: "It doesn't feel like any job spiritually makes sense"
  • Gary: "I'm spiritually fulfilled helping that church"
  • David: "What you work on is just the most important thing"

On Market Evolution​

  • David: "In a world where it's easy to build things, that just means it's going to be more and more important to stand out"
  • David: "People who have the skill set to run and build a go-to-market team... there's definitely going to be need for [them]"

On Church Opportunity​

  • David: "If you can solve the problem [of] membership going down, and actually turn one of these churches around... that instills hope in all the 99 plus percent churches"
  • Gary: "There's something around the lines of community and growth and using AI tools... that feel like the right level of abstraction"

On Life Balance​

  • David: "There's something nice about 9-to-5... I write in the mornings and at night, I have that flexibility"
  • David: "The future embarrassment of not being able to do it is driving me" (on fitness goals)

Action Items and Takeaways​

For Gary​

  • Continue exploring agentic workflow consulting while maintaining income stability
  • Consider faith-tech niche: helping churches with AI-powered growth
  • Evaluate Perplexity opportunity against spiritual alignment criteria
  • Compare notes with David on go-to-market courses and resources

For David​

  • Transition to spending 3 hours/day on go-to-market at Bevy
  • Prepare for post-Bevy transition in 20 months
  • Continue morning writing practice and worldview development
  • Support Gary as accountability partner for fitness and skills

Mutual Commitments​

  • Regular check-ins on fitness goals (both losing 10-15 lbs)
  • Share resources on go-to-market and AI workflow automation
  • Continue exploring faith-tech collaboration opportunities

Strategic Observations​

Career Philosophy Alignment​

Both Gary and David are navigating the tension between financial stability and purpose-driven work. David's structured approach (using current job to skill-build for future independence) offers a model for Gary's transition.

Market Opportunity in Faith-Tech​

The conversation revealed significant untapped potential in helping churches leverage AI for growth and engagement. With declining membership across denominations, churches need modern go-to-market strategies.

Go-to-Market as Core Competency​

David's thesis that go-to-market expertise will become increasingly valuable as AI commoditizes other functions aligns with Gary's skill set and interests in community building.

Importance of Patient Preparation​

David's emphasis on building pipeline, referrals, and confidence before going fully independent reflects lessons learned from the Intros.AI experience about market constraints.

Relationship Dynamics​

The conversation demonstrated the depth of trust between Gary and David, with Gary sharing vulnerable career doubts for the first time and David providing both practical and philosophical guidance. Their agreement to be accountability partners extends their relationship into personal development areas, strengthening an already robust friendship and potential business partnership.

Next Steps​

  • Gary to evaluate career options through spiritual alignment lens
  • Both to begin fitness accountability check-ins
  • Explore specific go-to-market strategies for churches
  • Share resources on AI workflow automation and go-to-market tools
  • Schedule follow-up to discuss progress on respective goals