Mastering the Art of Fundraising

Summary

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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.

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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]

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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 |

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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

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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.

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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.

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

Transcript

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[Startup Founder / Fundraising Expert]

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[Startup Founder / Fundraising Expert]

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[Startup Founder / Fundraising Expert]

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[Startup Founder / Fundraising Expert]

When I started raising money, I was doing everything wrong. And like one of the first rules that I say in my book, fundraising is don't say you're fundraising. Cause the second you say that you're fundraising, you're on the clock. Meaning people are gonna be like, all right, well his round should blow up and be over soon. Because if this is a hot company, I'm going to have a limited window. So if in two weeks your round isn't done, people are going to be like, why aren't others investing? And so they're going to, you know, they're going to walk away. And if you build up a bunch of no's around your company, people are not investing, then that's, you know, the network becomes aware that all these people didn't invest, and you're kind of screwed. So, you know, one of the first lessons that I learned from a great mentor of mine, his name is Michael Carter. He has this company, Playco, very successful gaming company. He was giving some talks on fundraising and he taught me this concept. Don't say you're fundraising, just go build relationships first. Go and meet investors and get them excited about who you are as a person and casually get them excited about your idea instead of going and saying, I'm pitching you, which automatically puts them on a pedestal versus you. Right. You're not peers anymore. Now they're on a pedestal. And so it sets the dynamics incorrectly. From the beginning. You're not building a relationship and you can get this, this domino effect of nos, which could really screw you before you even begin. So I did that in the beginning. I learned from those mistakes. I had some great mentors who helped me reshape my fundraising strategy.

[Interviewer / Podcast Host]

So you said something that I heard you say where you said, if you want money, ask for advice. If you want advice, ask for money. Yep, that's how I said it correctly.

[Startup Founder / Fundraising Expert]

Yeah.

[Interviewer / Podcast Host]

So can you elaborate on that?

[Startup Founder / Fundraising Expert]

Yeah, it's a pretty common adage in Silicon Valley, and so I certainly didn't invent that. But if you go to someone and you say, hey, I want, you know, to pitch you for funding, they're most likely going to give you advice, as they say, hey, you know, I'm not able to fund you right now, but how about I give you some advice? Whereas if you go to them and you show a genuine interest in their advice, but also potentially even more importantly, you really impress the shit out of them with who you are, and that person has money or is an investor, they're going to organically want to invest in you.

[Interviewer / Podcast Host]

So, so let's say I have a, a company and I'm trying to raise money and I know a very wealthy guy. Instead of saying, hey, do you want to, you know, hear my pitch to give me money to my startup? It would say, you know, I have this idea and I really respect you. Yeah. Your opinion. Would you want to just hear about it? Just to kind of give me some feedback on it? And you just do a really great job presenting it. And then they're like, damn, I got to be involved in this situation. But you're not. You don't look like you're so eager to just only get their money. You really genuinely want their advice, but then by you not wanting to take their money, they want to give you money even more.

[Startup Founder / Fundraising Expert]

Exactly. This approach is a win win makes it more comfortable for them. Right. Because they don't like saying no to you. It makes it more comfortable for you because if, if you're doing a good job, they're going to want to invest. If you're talking to an investor whose job it is to invest, who invests, they need you just as much as you need them. So if you're sitting in front of them and they're like, oh shit, this dude is going to kill it, they will proactively say, how can I get involved? And they're going to be just as likely, if not more likely than if you came to them explicitly trying to pitch.

[Interviewer / Podcast Host]

How, how intentional are you about it? Before you even go to get the advice, are you strategically targeting the people that you want to get the advice from? Like, is there a list? And it's like, if I could meet or get in front of this 10 or 20 people this month, that's my target. Like, how did you go about it?

[Startup Founder / Fundraising Expert]

Well, in the beginning, you know, beggars can't be choosers. Right. So you kind of will try to get meetings with anyone who has money. Right. I mean now you could be as you go later sage, you could be a little more picky and you should be picking and you should try to avoid putting sharks on your cap table who are at odds with you or who are very short termistic and they're going to create issues for you. You should avoid those to the maximum extent possible. But you know what I would do is I would try to build my network in a very strategic way. So I would host like happy hours or dinners. I do this on a college budget. I mean, I didn't spend, I spent minimal money on it. It was like a couple hundred bucks that I'd throw together. After a few, this VC would sponsor them. So they'd throw down 3, 400 bucks on these dinners and be at my place. Or I didn't spend a lot of money and so I was building network. So first step is build network of people who have Interconnectivity to investors and play the long game. Build a relationship with these folks casually. Make sure all these people in your network are impressed by you. Right. Casually. And then at some point you can make the asks or you can say, hey, I know this person invested in your company. I think they have this relevant experience of what I'm doing. Do you mind making the intro? And so you do that with all founder friends. People raise money before you're trying to build this network to cultivate and then eventually make the ask for introductions. And you know, you're just doing this on repeat as much as possible.

[Interviewer / Podcast Host]

So you said something also where it's like, you always want to avoid trying to get a no.

[Startup Founder / Fundraising Expert]

Yes. You don't. You never want to get a no. This is a little bit of the opposite advice that some would give you. Oh, you want to get to know quickly.

[Interviewer / Podcast Host]

Yeah, that's what, that's what I've heard 99 no. Because I come from sales. So that's what I heard all the time was like a no is always one step quicker to a yes or get to the no early or stuff like. But so that's interesting.

It even feels contradictory. It's like because you go, this is trial, right. Like, you're saying this because you've got no's.

[Startup Founder / Fundraising Expert]

Yeah, exactly. No's spread. So you know, investor community or the community you're raising within is small. And so you don't want somebody to go to someone you just pitched and that person say, be like, I passed. Right. You now, if you follow this strategy, you may have had a meeting with that person. It may not have went well. So they may not have invested, but you were never pitching them. So they don't have the ability to say I passed. Because you never went to them officially asking them for money.

[Interviewer / Podcast Host]

No. It actually makes a lot of sense psychologically because like you said, it becomes a virus once one person says no and then another person asks this person even if they want to say yes, it's like, well, why'd you say no? Right? And then it's like, I don't want to be the person that says yes and be an idiot when my friend who I have a high level of respect for, said no. So I'm more likely to lean towards the no because that's just where the crowd is going.

[Startup Founder / Fundraising Expert]

Exactly. And so the. What you're trying to create is a crowd momentum behind you. The hardest one to get the fall is the first one. And you have to get this person to fall just through Your character and your pitch and this strategy that I'm outlining. And then that one will hopefully turn to two or three. Once you have, like, three people is the magic number where three people have now casually, without you saying you're fundraising, have told you they want to get behind you. Now you can start a fundraising round with the wind at your back. Because you could say, the way I like to sequence it generally is, even when these people say, I want to back you, I won't say, okay, how much? Here's docs. You want to then take a step back once again and say, okay, I'm honored. I'd love to work with you. Let's do another meeting. I'd love to get your advice on these other things. I'd love to learn how you work with founders. I'd like to, you know, have this discussion on what working together would look like. I asked for references. Say, hey, can I speak to a couple other founders you've worked with? So, you know, when someone expresses interest,

[Interviewer / Podcast Host]

you don't just automatically jump and say, here, yeah, I'm ready.

[Startup Founder / Fundraising Expert]

Yeah, exactly. Yeah.

[Interviewer / Podcast Host]

I think that probably feels like the biggest mistake that most people make because you're in so much desperate. Not desperate need, but you're in need of the funds. And so once you feel an inkling of somebody who's interested, it's like, I gotta jump.

[Startup Founder / Fundraising Expert]

Become desperate. Yeah, you can't. You can't show the desperation, even if you are. Yeah, I've been desperate many times in my career, even beyond just our seed round.

[Interviewer / Podcast Host]

Yeah.

[Startup Founder / Fundraising Expert]

But you can never show it because this is what investors are. Their job is to sniff out desperation. Right. They're experts at this.

[Interviewer / Podcast Host]

So they can get the best deal possible.

[Startup Founder / Fundraising Expert]

So they can get the best deal possible. Exactly. So no matter what desperate situation you're in, I mean, you've got to come in with confidence. It's as simple as that. I mean, most people won't give this advice, but, I mean, it's just the truth.

[Interviewer / Podcast Host]

Yeah.

[Startup Founder / Fundraising Expert]

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[Podcast Narrator (Rorschach Murder)]

1010 shots fired.

[Startup Founder / Fundraising Expert]

City hall building. How could this have happened in City Hall? Somebody tell me that.

[Podcast Narrator (Rorschach Murder)]

A shocking public.

[Oppenheimer Representative]

This is one of the most dramatic events that really ever happened in New York City politics.

[Startup Founder / Fundraising Expert]

I screamed, get down. Get down. Those are shots.

[Podcast Narrator (Rorschach Murder)]

A tragedy that's now forgotten and a

[Startup Founder / Fundraising Expert]

mystery that may or may not have been political, that may have been about sex.

[Podcast Narrator (Rorschach Murder)]

Listen to Rorschach, Murder at City hall on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast.

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