Overview of Masters of Scale — How to break through a fear of failure, with Fawn Weaver & Van Jones
This episode is a live conversation between Fawn Weaver (founder of Uncle Nearest Premium Whiskey) and Van Jones recorded at the Masters of Scale Summit. Fawn tells the origin story of Uncle Nearest, reframes what entrepreneurs typically call “fear of failure,” and lays out the personal philosophies that carried her from researching a forgotten Black distiller to building one of the fastest‑growing and first billion‑dollar spirits businesses led by a Black woman. The discussion emphasizes authenticity, love, openness, historical blueprints, and the willingness to risk public embarrassment in order to scale.
Key takeaways
- The Uncle Nearest origin: Fawn discovered and amplified the story of Nearest Green — Jack Daniel’s early master distiller — and built a brand from that narrative. Her focus was on allyship and honor, not a victim narrative.
- Authenticity is a competitive advantage: Fawn “shows up as me,” not a polished representative, which creates trust and resilience.
- The common entrepreneurial “fear of failure” is often a fear of public embarrassment. Embracing public failure reduces paralysis and enables reinvention.
- Love (self‑love and relational love) is a strategic advantage in business — it keeps founders emotionally stable and open rather than guarded and reactive.
- Use historical blueprints: study past titans and patterns (Carnegie, Rockefeller, Reginald Lewis) for tactics and strategies rather than seeking a single modern mentor.
- Rejection reframed: interpret “no” as a redirection (Fawn frames it spiritually as “God saying no to point you elsewhere”), helping maintain openness and momentum.
- Pick mentors whose personal lives are intact — business success with personal dysfunction is a poor model to emulate.
Notable quotes
- “I always show up as me, never as a representative of myself.”
- “We were placed on earth to love and if the building supersedes the love you are going to walk around empty.”
- “I don't have a fear of public embarrassment.”
- “When someone says no to me I assume it's God, not that person.”
Topics covered
- The photo and history that revealed Nearest Green’s role at Jack Daniel’s and why Fawn pursued the story.
- Why Fawn thought the story would become a bestselling book and movie, not just a whiskey brand narrative.
- Business strategy through historical analogues (Carnegie, PR stunts, Reginald Lewis) rather than industry peers.
- The emotional life of founders: loneliness, ego, and the hole that building can leave if love is sidelined.
- Practical resilience: staying open to love and help, publicly risking failure, and measuring stress (anecdote about using an Oura ring).
- Mentorship criteria: prefer mentors with healthy personal lives.
- Spiritual framing of rejection as a navigational tool rather than an absolute block.
Actionable advice (what founders can do)
- Lead with your whole self: be authentic in public and private interactions to build trust and emotional stability.
- Reframe fear: treat what you think is fear of failure as fear of public embarrassment — practice small public risks to desensitize yourself.
- Study historical business models and leaders across industries; borrow tactics, not industry templates.
- Prioritize relationships and self‑love alongside growth goals — schedule time and boundaries for family and close relationships.
- Stay open to love and mentorship; if someone says “no,” use it as a signal to try a different approach or channel.
- Vet mentors for character and personal balance, not only professional accomplishments.
- Use objective tools (e.g., stress trackers) to maintain perspective on wellbeing during public challenges.
Who should listen
- Founders and aspiring entrepreneurs struggling with scaling or public risk.
- Leaders wrestling with the tradeoffs between personal life and company growth.
- Marketers and brand builders interested in narrative-driven growth.
- Anyone curious about combining purpose, storytelling, and commercial scale.
Context & resources
- Fawn Weaver is the founder of Uncle Nearest Premium Whiskey; she authored Love and Whiskey (the book mentioned).
- Episode recorded live at the Masters of Scale Summit, Presidio Theater, San Francisco.
- The episode mixes personal philosophy, brand origin story, and practical guidance for scaling with emotional intelligence.
If you want a one-line summary: build bravely, lead authentically, prioritize love, and treat public failure as a tool for growth rather than a barrier.