Gary Sheng and David Kobrosky Life Transitions and Spiritual Discernment

Date: September 16, 2025 Participants: Gary Sheng, David Kobrosky Format: Phone call Location: Gary in Austin; David in New York Context: Catching up on major life transitions, career pivots, spiritual discernment, and strategic advice during periods of uncertainty

Executive Summary

This conversation captures both participants in significant transition phases - Gary navigating a failed Tulsa opportunity and exploring faith-based calling toward church technology, while David settles into post-acquisition life at Bevy with expanded responsibilities and upcoming engagement to Mikayla. The discussion reveals Gary's spiritual evolution from secular ambition to surrendering to God's guidance, including fasting for discernment and cleansing from various habits. David provides strategic counsel about the importance of working on the right thing rather than rushing into opportunities, sharing lessons from his Intros.AI journey. The conversation demonstrates deep friendship, mutual respect, and David's continued belief in Gary's potential for building movement infrastructure, now potentially in the faith space.

Key Themes and Strategic Insights

Gary's Spiritual and Professional Transition

Failed Tulsa Opportunity - Character vs Intelligence:

"But certain kinds of intelligence is not character... If he's willing to have two or more kids out of wedlock or in infidelity with his wife, and it just keeps happening, it's like, okay, who am I? I'm not as special as his wife, right? Of course he's willing to bend the truth with other people."

Spiritual Calling Discovery:

"I met this woman that put me onto this one pastor that had been doing healing miracles... What if healing miracles are still happening in modern day? I think people need to know about it. And they need to understand why they're happening. And I think there's some kind of role for me to play in that."

Church Technology Vision:

"I'm just starting to explore what, essentially, what kind of church tech might be worth building... I'm kind of envisioning a network of healers, a network of healing pastors that have had documented miracles."

Spiritual Discipline and Cleansing:

"What I've done some of the things I've done in the past month and a half is I've quit psychedelics, I've quit coffee... Been getting off of porn. So I'm just trying to get... really cleanse a lot of the impulses to just do stuff."

Fasting for Discernment:

"On the note, I'm fasting for at least three days... You probably know this, it's a Judeo-Christian thing where you fast to hear God's voice clearly."

Paradigm Shift from Self-Will to Divine Guidance:

"The paradigm shift from figure out how to enact this practically, as someone that wants to make a positive impact... it's all like, self willed... And now... a lot of them [impactful Christian leaders], all they did was just listen. They prayed, they listened to, okay, God, where do I go next? What do I do next?"

David's Post-Acquisition Success at Bevy

New Role and Responsibilities:

"I am the product lead for all AI initiatives... there's three plack lines I'm, like, owning. So one is, like, under AI Features, we have, like, search... Another big piece is analytics... And then the other is... go to market initiatives."

Revenue Attribution Focus:

"I think the most important thing is if I can tie engagement directly to revenue... we're trying to be able to explicitly say, hey, you spend 500k in Bevy, we're driving $10 million in revenue for you because of these clear points."

Executive Trust and Acquisition Planning:

"Gary pulled me into a chat a couple days ago... you're the only one in the company who sold a company, and we want to sell a company in the next two years for well over 100 million... He sees me as, like, part of the trust circle."

Incentive Alignment:

"I actually personally get 10% of any deal I refer to Bevy... if I can, like, land a 500k deal, that'd be another huge bump for me."

Market Opportunity - Khoros Disruption:

"Khoros is like community platform that Microsoft and like Cisco use... they have about 65 million revenue. But they were bought two months ago from P.E. so P.E. buys this company, fires 80% of the staff... And everyone's leaving that company, all their customers."

Strategic Business Philosophy and Lessons

David's Key Lesson from Intros.AI:

"The biggest thing I learned from intros is that, like... what you work on is just the most important thing, like, just hands down... if I was optimizing for a successful company, it probably would have made sense to not start with intros."

Market Constraint Realization:

"I was confined to the market of investors view on community market. I was confined to the budgets of enterprises... budgets around community. Like, I was kind of confined in this way that like, no matter how well it went... I would happen to have pretty low ceiling."

Time Investment Philosophy:

"If it took me another year to better figure out... the right angle and approach... I probably could have gotten to that five year point in two years... your time is super valuable, but, like, less valuable than urgency. It's just getting it right."

Strategic Patience Advice:

"I would caution against it as much as I can caution against it just because... it's almost like... Yeah, it's... Yeah, it's almost like... Yeah."

Personal Life and Relationship Updates

Mikayla Engagement Plans:

"I'm proposing in a month. I don't know if I told you that that's a big deal."

Traditional Proposal Approach:

"I flew her dad out to ask him for her hand... It was just me and him going to the US Open together... I told him, I was like, you know, I've been with Mikaela for three years, and I know I want to be with her for the rest of my life."

Father's Response:

"He's like, I've known her for 25 years. You sure about that? You know, think about... Yeah, classic."

Work-Life Balance Achievement:

"My new schedule is so good. I get to spend like 8AM to 11AM after my morning workouts just, like, writing and working, like, fun side projects... I'm working really hard, 40 hour weeks... really intense, like working hard, but like, only for that time."

Market and Technology Insights

Point Solutions vs Comprehensive Platforms:

"Point solutions are becoming less... less of an angle... companies are saying, like, they want to consolidate into one tool or one buyer... it probably makes more sense for intros to be part of another feature on top of another company."

AI Impact on Business Models:

"It's much easier now because you know AI tools... it's much easier to spin up products and companies. I think it's pretty reasonable in my mind to... pick a company where I can get to like, 300 to 500k in ARR just like, just kind of vibe coding it myself."

Personal Consultant Trend:

"It seems as though people having personal consultants is, like, a small trend... folks are like, oh, you have a really rich person, you can just hire someone or hire consultancy for, like, you know, couple hundred K a year to, like, build you products."

Friendship and Mutual Support

David's Consistent Impact on Gary:

"After hanging with you, I just feel great or have chatting with you. I don't know what it is. But it's a one quality I've known you have."

Sacred Wilderness Phase Recognition:

"You're in a sacred place right now... you have desert for 40 years, right? In the best way... this is usually where insight happens, and this is, like, where you know the playing built in front of you."

Patience and Process Wisdom:

"You can't rush this space... these types of spaces only come what? Every roughly two to five years... this is an important place to just sit in."

Stuckness as Valuable State:

"I love this idea of, like, stuckness... it's important to be skating in a darkness, because usually if you sit there long enough, whatever, you know, whatever supposed to reveal itself, you will just kind of reveal itself."

Personal Development and Character Growth

Gary's Spiritual Discipline Evolution

• Quit psychedelics, coffee, and pornography
• Implementing fasting for spiritual discernment
• Shift from self-willed action to divine guidance
• Recognition of calling vs arbitrary opportunity pursuit

David's Professional Maturation

• Strategic thinking about market positioning and timing
• Long-term planning for post-Bevy transition
• Building personal brand and industry relationships
• Balancing ambition with relationship priorities

Strategic Implications and Future Directions

For Gary:

• Church technology represents alignment of skills with spiritual calling
• Need for deeper market research in faith-based community tools
• Potential for healing miracle documentation and verification systems
• Opportunity to build movement infrastructure in Christian context

For David:

• Positioned for significant financial upside through Bevy acquisition
• Building expertise in AI-driven community analytics and attribution
• Developing go-to-market skills alongside product leadership
• Strategic preparation for next entrepreneurial venture post-Bevy

Collaboration Potential:

• David's community building expertise could apply to church networks
• Intros.AI matching technology adaptable for faith-based connections
• Shared vision for movement infrastructure now extending to spiritual realm
• Mutual support during transition phases and major life decisions

Relationship Dynamics

This conversation demonstrates the deep trust and mutual respect between Gary and David, with David serving as both strategic advisor and emotional support during Gary's period of discernment. David's recognition of Gary's "sacred wilderness" phase shows sophisticated understanding of spiritual and professional development cycles. The friendship has evolved to encompass both secular business strategy and spiritual guidance, with both participants supporting each other's growth in different life domains.

Key Quotes for Future Reference

On Divine Guidance vs Self-Will:

"That God cares if you are aligned with his call, he just tells you how to get it done. I'm still grappling with that... the part of me that through insecurity of not feeling productive every minute of my life, he is gone. Or I'm trying to kill it."

On Sacred Transition Periods:

"You're in this. You're in this. Like, this is usually where insight happens, and this is, like, where you know the playing built in front of you... this is a special place, right? You can't rush this space."

On Strategic Patience:

"Your time is super valuable, but, like, less valuable than urgency. It's just getting it right."

On Working on the Right Thing:

"The biggest thing I learned from intros is that... what you work on is just the most important thing, like, just hands down."