Podcast Summary: Earn Your Leisure – "Mastering the Art of Fundraising"

Hosts: Rashad Bilal and Troy Millings
Guest: Startup Founder / Fundraising Expert
Date: April 1, 2026

Episode Overview

In this episode, Earn Your Leisure dives deep into the art and psychology of startup fundraising. The guest, an experienced founder and fundraising expert, breaks down unconventional but proven tactics for securing investment, building powerful networks, and maintaining the upper hand throughout the fundraising process. Core themes revolve around the importance of relationship-building, subtle positioning, and how founders can take control of the investor dynamic to maximize success.

Key Discussion Points & Insights

1. Don’t Announce You’re Fundraising (02:20–04:16)

• Lesson: Avoid explicitly telling investors you’re raising money.
• Why?: Announcing a round “starts the clock” and increases pressure. If momentum doesn’t build quickly, people assume “others aren’t investing,” spreading negative perceptions.
• Quote:

  “The second you say that you're fundraising, you're on the clock… if in two weeks your round isn't done, people are going to be like, why aren't others investing?”
  — Startup Founder / Fundraising Expert [02:26]

• Tactic: Instead, focus on building relationships and getting people excited about you and your idea “casually.”
• Mentor Mentioned: Michael Carter (Playco) taught the guest to never pitch outright and to connect as peers.

2. The Psychology of Asking for Advice vs. Money (04:16–05:56)

• Common Adage:

  “If you want money, ask for advice. If you want advice, ask for money.”
  — Interviewer / Podcast Host [04:16]

• Meaning: Directly asking for money often gets only advice in return, while seeking advice and impressing the individual can organically lead them to want to invest.
• Quote:

  “If you go to them and you show a genuine interest in their advice... and really impress the shit out of them... they're going to organically want to invest in you.”
  — Startup Founder / Fundraising Expert [04:28]

3. Strategic Targeting and Networking (06:41–08:54)

• Start Small, Then Be Selective:
  • Early on: meet with anyone who might invest.
  • Later: be choosy; avoid “sharks” and short-term-minded investors.
• Network Building:
  • Host low-cost events, happy hours, or dinners—even on a “college budget.”
  • Invite VCs and founder peers to foster connections.
  • Gradually, investors even start sponsoring such gatherings.
• Long Game: The goal is to cultivate relationships so that when you ask for introductions, there’s already trust and reputation built.
• Quote:

  “Build a relationship with these folks casually... make sure all these people in your network are impressed by you.”
  — Startup Founder / Fundraising Expert [07:30]

4. Avoiding the Dreaded “No” (08:54–10:34)

• Contrarian Advice: Contrary to many sales teachings, never push for a no.
• Reason: The investment community is small; a single “no” can cascade into many.
• How It Works:
  • If you never explicitly pitch, potential investors can’t say they “passed”—so it doesn’t hurt your reputation.
• Quote:

  “No’s spread... You don’t want somebody... to say ‘I passed’... If you follow this strategy, you may have had a meeting... but you were never pitching them.”
  — Startup Founder / Fundraising Expert [09:30]

5. Building Momentum Organically (10:34–12:21)

• Get Early Support: The hardest is getting the first backer—but once you do, more often follow.
• Three is Magic: Once three people casually indicate interest, you have momentum to start a round.
• Take Your Time: Even when someone wants to invest, don’t rush into paperwork. Instead, continue to engage, ask for advice, references, and ensure mutual fit.
• Quote:

  “When someone expresses interest, you don’t just automatically jump and say, ‘here, yeah, I’m ready.’”
  — Interviewer / Podcast Host [11:52]

• Maintaining Leverage: Don’t show desperation, stay confident, and remember that investors need founders just as much.
• Quote:

  “You can't show the desperation, even if you are... Their job is to sniff out desperation. They're experts at this... So no matter what, you've got to come in with confidence.”
  — Startup Founder / Fundraising Expert [12:12]

Notable Quotes & Moments

| Timestamp | Quote | Speaker | |-----------|-------|---------| | 02:20 | “One of the first rules… fundraising is don’t say you’re fundraising…” | Startup Founder / Fundraising Expert | | 04:16 | “If you want money, ask for advice. If you want advice, ask for money.” | Interviewer / Podcast Host | | 04:28 | “…show a genuine interest in their advice… They’re going to organically want to invest in you.” | Startup Founder / Fundraising Expert | | 09:30 | “No’s spread… If you follow this strategy, you may have had a meeting… but you were never pitching them.” | Startup Founder / Fundraising Expert | | 11:52 | “You don’t just automatically jump and say, ‘here, yeah, I’m ready.’” | Interviewer / Podcast Host | | 12:12 | “You can't show the desperation, even if you are... Their job is to sniff out desperation…” | Startup Founder / Fundraising Expert |

Important Segment Timestamps

• 02:20 – The pitfalls of announcing a fundraising round
• 04:16 – The “ask for advice” principle explained
• 06:41 – Strategic networking and early stage tactics
• 08:54 – Why you should avoid getting “no’s”
• 10:34 – Harnessing momentum and staging the round
• 12:12 – The importance of confidence and concealing desperation

Episode Tone & Style

The conversation is direct, candid, and pragmatic, blending Silicon Valley know-how with street-smart experience. Both hosts and guest maintain an encouraging, down-to-earth approach—pulling back the curtain on the real, often unspoken emotional dynamics of securing investment.

Takeaways for Aspiring Fundraisers

• Cultivate relationships; don’t rush to pitch.
• Don’t explicitly signal you’re fundraising until you’ve organically built demand.
• Leverage the social network effect—momentum matters.
• Confidence is as important as your business fundamentals.
• Be strategic in both network-building and the timing of fundraising asks.
• Don’t let the fear of ‘no’ dictate your process—eliminate the risk of “no’s” spreading by staying in control of the narrative.

This episode offers a masterclass in the psychological game of fundraising—valuable advice for founders, entrepreneurs, and anyone interested in startup funding.