The Money Mondays – E159: "Founders, Creators, & Communities"

Host: Dan Fleyshman
Guests:

• Yash Daftary (Founder & CEO, Fan Basis)
• Chris Mead (Co-Founder, Founders Club)
• Aaron Spivak (Co-Founder, Founders Club)
  Date: February 9, 2026

Brief Overview

This episode of "The Money Mondays" brings together three emerging leaders: Yash Daftary (Fan Basis), Chris Mead, and Aaron Spivak (Founders Club). Hosted inside the “MTV Cribs”-style Money Mondays podcast, Dan Fleyshman steers a fast-paced, commercial-free conversation on three major themes:

1. How to make money (building business as a creator or founder)
2. How to invest money (from operational strategy to angel investing)
3. How and why to give it away (company & personal philanthropy)

The guests share stories about building scalable businesses for creators and founders, the importance of curated community, the pitfalls of sudden wealth, and actionable investing diligence. The tone is energetic, motivational, and practical, aiming to extract insights for both novice and seasoned entrepreneurs.

Key Discussion Points & Insights

1. Building Fan Basis: Empowering Creators as Entrepreneurs (00:56–12:49)

Who: Yash Daftary

• Origins & Pivot (02:00):

  • Fan Basis originally began as a high-profile fan experience platform (think “Cameo on steroids”) focused on celebrities, athletes, and influencers selling meet-and-greets or lessons.
  • Realized the scalable value was in enabling creators to build “real” digital products (courses, programs, memberships) instead of one-offs.
  • Quote:
    “There’s only so many virtual meet and greets Dennis Rodman is going to sell… but you see the top earners actually selling digital products that add informational value.” (03:22 – Yash)

• What Holds Creators Back (04:34):

  • Many creators see sponsorships as the only path, but real money comes from using your personal brand to launch and grow a business.
  • The mindset shift: move from “influencer” who gets paid for posts, to “internet entrepreneur” running a business, with content feeding a product/service funnel.
  • Quote:
    “What separates the guys making $10K a month from those making $500K or a million? They’re internet entrepreneurs, not just influencers.” (06:04 – Yash)

• Deciding What to Sell (06:38):

  • Authority and authentic connection to the product matter—your audience must care about what you offer.
  • Transformational stories, especially in health/fitness, create relatability and trust.
  • Quote:
    “If it doesn’t matter to your clients and audience, no one’s going to end up buying it.” (07:01 – Yash)

• Who Fan Basis Serves (08:41):

  • Initially aimed at personal-brand entrepreneurs, but now serves creators, agencies, membership communities, and software startups—anyone selling digital/non-physical products.

• Increasing Average Order Value (AOV) with Tools (09:59):

  • “Buy Now, Pay Later” (BNPL) boosts AOV, making higher-ticket offers accessible via financing, and increasing business revenues by up to 38%.
  • Integration of multiple business tools (payments, affiliates, community, course hosting) creates a central “operating system.”

2. Investing in People & Scaling Culture (12:49–17:46)

Who: Yash Daftary

• Why Double Down on Talent (13:02):

  • Rapid scaling (from 18 to 100 employees in a year) underscores culture and fit are more critical than just pure technical skill or experience.
  • The most valuable hires have “founder DNA”—failed entrepreneurs who think in outcomes.
  • Quote:
    “The best investment is people… my core team cares as much as I do—sometimes even more.” (13:02 – Yash)

• Hire for Culture, Not Just Talent (15:34):

  • Sacrificing culture for skill (even in high-performing hires) disrupts teams: “We realized quickly that getting people that…are bought into the vision is vital.” (16:50 – Yash)

3. Wealth Events: Handling Sudden Capital and Investment Strategy (17:46–25:50; 27:43–29:48)

Who: Yash Daftary and Dan Fleyshman

• Dealing with Sudden Wealth After a Liquidity Event (17:46):

  • Remove emotion from investments. “The biggest mistakes I’ve seen: people writing checks without due diligence.” (18:50 – Yash)
  • Diversification is key—but focus on what you actually understand, and bring in skilled advisors.
  • Quote:
    “Don’t start doing 50 different things at once just for the sake of diversifying. Figure out what you’re good at.” (20:22 – Yash)

• Due Diligence Before Investing (21:06):

  • Request the cap table, analyze org structure, review financials (use AI tools to simplify), research public sentiment and especially talk to real customers—including those who left mixed/negative reviews.
  • Reference checks should go beyond those “cherry-picked” by the founders.
  • Quote:
    “The financial picture always paints the most telling story out of anything.” (21:39 – Yash)

• Dan’s “Four Horsemen” Investment Filter (23:48):

  • Four experts (accountant, lawyer, CEO, field-specific advisor) must sign off—protects against “getting excited” and minimizes investment FOMO.
  • Pro tip: Most people who pitch don’t have their investor docs together. Just asking for them is a way to weed out unserious opportunities.

4. Charity: Giving Back with Purpose (25:50–29:48)

Who: Yash Daftary and Dan Fleyshman

• Strategic and Authentic Philanthropy (25:50):

  • Charity brings meaning, can open business doors, and helps build relationships.
  • Authentic engagement—doing what you care about, not just “for optics”—matters most.
  • Quote:
    “It shows a whole other side of a person when it’s not just about ‘how can they benefit from every single relationship?’” (27:18 – Yash)

• Planning Intergenerational Wealth (27:43):

  • Both prudence and values: Yash suggests leaving ~90% to (well-raised) children but wants them to earn their way (“access to everything except capital”).

Notable Quotes

“There’s only so many virtual meet and greets Dennis Rodman is going to sell… but you see the top earners actually selling digital products that add informational value.” (03:22 – Yash)

“The best investment is people… my core team cares as much as I do—sometimes even more.” (13:02 – Yash)

“Don’t start doing 50 different things at once just for the sake of diversifying. Figure out what you’re good at.” (20:22 – Yash)

“The financial picture always paints the most telling story out of anything.” (21:39 – Yash)

Founders Club: Building a Curated Global Entrepreneur Community (32:09–64:26)

Who: Chris Mead & Aaron Spivak

Origins & Purpose (32:09–36:15)

• Both founders built 8- and 9-figure businesses (Crossnet, Hush, multiple brick & mortar studios).
• Realized the loneliness and challenge for young, first-time founders—community and trusted networks are critical for scaling and for personal support.
• Founders Club designed to be a “modern day YPO”: simultaneously business fraternity, mastermind, and life resource.

Quote:

“We believe that environment is way stronger than willpower… It’s easier to achieve self-actualization surrounded by like-minded people.” (35:30 – Aaron)

Membership, Structure & Events (36:15–42:52)

• Average member: 35 years old, ~$14M/year business; 65% male/35% female. Now includes billionaires.
• Admission is highly selective to keep the culture: “less than 4.5%” of ~3,500 monthly applicants accepted.
• Six core chapters (Miami, NY, LA, Austin, Toronto, Vancouver) and virtual activities.
• 150+ events/year: ranging from local masterminds, F1 outings, group exercise, to the annual “Forum”—a 500-person destination festival focused on curation, not just celebrity speakers.
• Strong “give before you take” culture—soliciting/pitching is forbidden; members kicked out for violation.
• Quote:
  “We’re curating all day long these environments for people to step into and reach their highest self.” (38:31 – Aaron)

Curation, Culture, and Trust (42:52–45:11)

• Each member is background-checked and revenue-verified; peer groups are thoughtfully curated for trust and vulnerability.
• “No phones” policy during masterminds to increase focus and openness.
• “Everyone brings energy—you leave full, not drained.” (45:11 – Aaron)

Why Build After Exiting? (48:43–52:59)

• For founders who’ve sold businesses, loss of identity/purpose is real; the community brings meaning, fun, and connection back.
• Growth was organic: from subsidized dinners with founders to a robust, global network.

The Future & Infrastructure (52:59–55:33)

• Expanding globally, especially in Europe.
• Membership is demand-driven and highly referral-based, ensuring quality.
• Pricing model/cap on numbers ensures exclusivity—“badge of honor” like YPO.
• Quote:
  “As long as every single person that comes in meets the criteria… it’s only more powerful with more [members].” (53:57 – Aaron)

Deal Flow, Investing, and Member Value (55:40–62:03)

• Currently don’t allow in-event pitching but see strong member demand for “deal flow.”
• Dan breaks down his Elevator Syndicate model: 1,100+ accredited investors; live opportunity presentations; Angellist backend; low-friction transactions.
• Key emphasis: Rigor in vetting, and alignment with member needs (e.g. “building for every season of your life”).

Philanthropy & Social Impact (62:49–66:34)

• Both founders share candidly that charity hasn’t been core YET, though it's top-of-mind for future growth, especially with large events.
• Tension: want to see impact and ensure donations are meaningful.
• Dan advises: authentic, visible impact (e.g., beach cleanups, hands-on giving), not just money, builds the right culture.
• Quote:
  “Sometimes it’s just the time and energy. You get the Founders Club to go to the beach and clean up, and you can see the cause and effect.” (66:09 – Dan)

Wealth and Legacy Planning (68:36–72:03)

• Both founders reflect on their upbringing and the dangers of inherited wealth.
• Spivak prefers to give primarily resources and connections, not cash: “Personally, I don’t see myself leaving any money behind… I want to maximize this whole lifetime.” (70:15)
• Mead advocates for structures that instill values (e.g. trust-stipends vesting at age 40).

Timestamps & Memorable Moments

| MM:SS | Segment | |-----------|-----------------------------------------------------------------| | 02:00 | Yash explains Fan Basis’s shift from celebrity fan experiences to a platform for digital products | | 04:34 | Why most creators don’t monetize: mindset, not resources | | 09:59 | The power of increasing AOV – Buy Now, Pay Later for creators | | 13:02 | “Best investment is people” and scaling culture | | 18:50 | Yash on avoiding emotional investing and the need for due diligence | | 23:48 | Dan’s Four Horsemen investing framework | | 25:50 | Why charity matters for business and relationships | | 32:09 | Chris Mead & Aaron Spivak share their entrepreneurial origin stories | | 36:21 | “We’re curating for mind, body, and business—not just money” | | 40:43 | Annual “Forum” event: an entrepreneurship festival | | 42:57 | Curating member groups—only a small percent accepted | | 45:11 | “You leave full, not drained” – event culture | | 53:08 | Future vision: global impact and expansion | | 55:40 | Deal flow for community: pros, cons, and how Dan runs his syndicate| | 62:49 | Charity: candid reflections on finding the “authentic cause” | | 68:36 | What % of wealth to leave to children? Varied, nuanced replies |

Takeaways For Listeners

• For Creators:

  • Build a business around your brand, not just a brand—think like an entrepreneur, not just an influencer.
  • Tools like BNPL and centralized platforms (i.e. Fan Basis) can massively increase revenue.
  • Authenticity—selling what connects with your story and authority—is essential.

• For Entrepreneurs/Founders:

  • Community matters: Isolation is the enemy; curated peer networks can accelerate business and life.
  • Maintain a strict culture fit in hiring and membership; selectivity sustains value.
  • Plan ahead for investment events, liquidity, and sudden wealth—rigorous due diligence and relying on trusted advisors is non-negotiable.

• For All:

  • Philanthropy should be authentic and visible; giving can be time, energy, or money, but should have a measurable impact.
  • Legacy planning: focus on providing values and opportunity, not just a financial windfall.

Where to Find the Guests

• Fan Basis: fanbasis.com
• Yash Daftary: Instagram @yashdaftary
• Founders Club: foundersclubofficial.com, @FoundersClub on all socials
• Chris Mead: @ChrisMead (Instagram, Twitter, LinkedIn)
• Aaron Spivak: @Spivak (Instagram, LinkedIn)

For founders, creators, or investors looking to level up—this episode offers candid, actionable wisdom on turning momentum into money, building community for life, and making impact that matters.