The Power of Real Conversations with David Homan
Unlearn
The Art of Authentic Asking in Startup Fundraising
This chapter delves into the difficulties individuals encounter when seeking help, especially in fundraising for startups. It highlights the contrasting approaches of givers and takers, underscoring the necessity of authentic relationships and clear communication to cultivate meaningful support.
What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and co-author of Orchestrating Connection, David breaks down the silent skills that build trust, activate communities, and transform the way we gather.
David Homan is the founder and CEO of Orchestrated Connecting, a global community of connectors; Orchestrated Opportunities, an impact-focused advisory firm; and SOAR CONNECT, a start-up focused on the strength of authentic relationships. He hosts the Orchestrated Relationships podcast on developing relationship value, is an active classical composer, and a proud father of two. From middle-class beginnings as the son of a college professor and nonprofit-focused mother, he has built a network that reaches into the most private and powerful circles globally, all while honoring a code of purposeful community building.
Key Takeaways
- Small Groups Create Big Impact: Starting events with curated small groups breaks social barriers and sets the stage for authentic connection.
- Vulnerability Builds Real Relationships: Opening up—even subtly—invites empathy and depth that surface-level networking can't achieve.
- Help Without Keeping Score: Giving without expecting reciprocity strengthens your reputation and extends your reach.
- Design Moments That Resonate: Successful events don’t depend on cocktails or keynote speeches—they’re built on meaningful first impressions.
- Asking Is a Skill, Not a Weakness: Givers often struggle to ask for support—David’s Impact Ask framework helps mission-driven people share their needs with clarity.
Additional Insights
- Most Networking Events Are Designed to Fail: Traditional formats emphasize aesthetics over connection—David redesigns them to foster immediate, meaningful dialogue.
- Shared Vulnerability Activates Group Trust: Structured conversations with depth-based prompts unlock faster bonding and community-building.
- Music as a Metaphor for Human Connection: David draws from his training as a classical composer to illustrate how relationships, like instruments, must resonate and harmonize.
- Clarity Makes Asking Easier: The “Impact Ask” framework simplifies how to articulate passion, purpose, and the kind of help you need.
- Your Reputation Travels Faster Than You Do: David’s work shows that investing in authentic relationships amplifies your presence—even when you're not in the room.
Episode Highlights
00:00 – Episode Recap
David Homan reveals how he had to unlearn everything he thought he knew about networking—discovering instead that vulnerability, deep listening, and structured intimacy were the keys to building purposeful community.
01:50 – Guest Introduction: David Homan
Barry introduces David Homan, master connector, startup founder, and co-author of Orchestrating Connection, whose work helps leaders create impact-driven relationships through authentic connection.
02:52 – Why Most Events Miss the Mark
David shares why traditional networking events feel awkward—and how his approach to curated small groups flips the script to create meaningful experiences.
04:49 – Start Small, Go Deep
Barry reflects on the power of small group interactions and how vulnerability accelerates meaningful connections.
08:01 – Sharing Real, Not Polished
David explains the importance of self-worth and courage when choosing to open up authentically in conversation.
10:45 – Creating Connection Through Authenticity
Being real invites empathy—and sets the tone for deeper, more rewarding conversations.
13:18 – Your Reputation When You're Not in the Room
David describes how authentic acts ripple through your network, strengthening your reputation and reach over time.
17:39 – Unlearning Transactional Thinking
Helping someone doesn’t obligate them—it expands your access to their trusted circles.
20:36 – Conducting Communities Like a Composer
David draws on his classical music training to explain how relationships can resonate like instruments in a symphony.
25:16 – Event Design That Actually Works
Purpose-driven event planning means matching people’s needs and asks—not just gathering for the sake of it.
28:13 – Why Givers Struggle to Ask
David outlines the “Impact Ask” framework to help mission-driven people communicate their needs confidently.
31:59 – Fundraising as Shared Mission
Barry reflects on how reframing fundraising as an invitation to join a mission transformed his startup experience.
33:59 – The Future of Community
David offers a hopeful vision: intentional communities built on shared values, layered for systemic change.
35:56 – How to Connect with David
David shares how listeners can join his private, connector-driven community—and what qualities matter most.
Useful Resources
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