Podcast Summary: Help Wanted – How to Ask Friends for Money

Host: Jason Feifer (Entrepreneur magazine Editor-in-Chief)
Co-host: Nicole Lapin (Money Expert)
Guest: Jess Chermack
Date: September 9, 2025

Episode Overview

In this episode, Jason and Nicole wrestle with a common but awkward work-life dilemma: How do you ask a friend for money, especially in situations with social nuances—like an unexpected traffic ticket after loaning your car? With special guest Jess Chermack, they candidly unpack the financial and emotional complexities of “the ask,” offer practical scripts, and explore why even seasoned professionals get the “ick” from money talks.

Key Discussion Points and Insights

1. Why Asking Friends for Money Is Awkward

• Nicole admits discomfort despite her financial confidence:
  • “I have it sorted. Ish. But that doesn't make me immune from the ick of money talks. For sure. They get ick.” (03:03, Nicole)
• Two Types of Asks:
  • Asking because you need money
  • Asking for repayment for something owed
  • Both are fraught with social anxiety, even when justified.

2. Jess’s Dilemma: A Real-Life Scenario

• Jess lent her car to a friend. Later, a $75 traffic ticket for an express lane violation arrived in the mail.
• Jess faces hesitation: Should she ask her friend to pay, even though it was a friendly favor and the friend works in the not-always-lucrative theater industry?
  • “It’s $75…it’s at the end of the day, I’m never going to notice that it’s gone, but it’s taking up mental real estate, and it always will if I pay it without asking the friend…” (09:32, Jess)

3. Walking Through the Emotional Hangups

• People-pleasing and confrontation aversion:
  • “The psychology of it, I think, is just being a people pleaser and, like, trying to avoid confrontation in general. I'm a woman who was raised in America, which…I think this is like a standard narrative here.” (08:53, Jess)
• Fear of mortifying the friend:
  • “I don't want her to feel mortified.” (15:14, Jess)
• Possible friend reactions weighed:
  • “What if the friend says no?” (09:32, Jess)
  • “What if…there's just no reply or acknowledgement?” (17:18, Jess)

4. Practical Solutions: Scripting the Ask

• Keep it light, focus on the circumstance, not blame:
  • “Hey, friend, funny story. Yeah. The worst. Ate these stupid cameras…And then show her the picture.” (15:23, Nicole)
• Frame as a shared enemy (the system, not the person):
  • “Like, you're both against whoever that is. Colorado traffic enforcement people. If you're not against her, you're united in this is annoying.” (30:29, Nicole)
• Use Venmo/Zelle request functions to depersonalize:
  • “Everything is solved by the request function in Venmo.” (33:29, Jason)
• Consensus: Ask directly but gently:
  • “Cool if I send you a Venmo request?” (33:24, Nicole)

5. Addressing Anxiety: Worst Case Scenarios and Cognitive Reframes

• Stoicism and practical pessimism:
  • “What's the worst that can happen? Let's use some stoicism.” (16:06, Nicole)
• Jason’s Four Explanations Framework:
  • “There are four, count them, four possible explanations for everything at all times. And those are: a catastrophic explanation, a bad explanation, a neutral explanation, a good explanation.” (34:47, Jason)
  • This helps short-circuit the spiral of social anxiety when waiting for replies.

6. Resolution: The Ask and the Friend’s Response

• Live text drafted and sent:
  • “Hey, Colorado is apparently ridiculous and has installed random cameras on the highway...We got this ticket in the mail from when you were borrowing the car. Cool if I send you a Venmo request?” (31:10-33:43, Jess + hosts)
• Immediate positive reply:
  • “She says, ‘Fucking hysterical. Yes, please send it. I’ll pay right now.’” (36:43, Jess)
• Takeaway: The discomfort was much greater in anticipation than in outcome. Direct, non-judgmental honesty worked—the friend was gracious and unbothered.

Notable Quotes & Memorable Moments

• On Lending Money to Friends:
  • “If you lend a friend money, decide which you value more, the friend or the money, because it really does mess up relationships. Or I often just reframe it as a gift.” (03:40, Nicole)
• On Overthinking the Ask:
  • “This is validating the core emotional challenge of this question, which is that...everything that we come up with either feels like too weird or too pushy...when it shouldn’t.” (31:22, Jason)
• On Making it Easier:
  • “Serious. I know it exists. Yeah. I've always just texted people and been like, oh, that thing was $70. And then they Venmo me. So I've never sent the request. But now that I think about it, that would have solved the problem.” (13:08, Jason)
• On the Emotional Premium:
  • “There’s a premium to feeling like justice has been served.” (21:38, Nicole)
• Final Resolution:
  • “She says, 'Fucking hysterical. Yes, please send it. I’ll pay right now.'” (36:43, Jess)
• On Lessons Learned:
  • “May this moment right now be the reminder for most people that almost always this works out just fine. You spent a lot of time worrying about this. And actually, the whole thing could have been resolved in about 20 seconds by writing a...cheeky text and sending it off, and she would have replied 10 seconds later, and it would have all been fine.” (39:16, Jason)

Timestamps for Key Segments

• 03:03 - Nicole admits even money experts feel awkward.
• 04:48 - Jess introduces her car-loan dilemma and $75 ticket.
• 08:53-09:32 - Jess explores her hesitation and people-pleasing roots.
• 10:31 - Jason and Nicole agree the ticket ask is justified.
• 15:23 - Nicole’s light script & suggestion.
• 16:06 - Nicole introduces the “worst case scenario” game.
• 30:29-33:24 - Producing and revising the actual text to send the friend.
• 34:47 - Jason’s “Four Outcomes” reframing tool.
• 36:43 - Jess receives a perfectly positive response from her friend.
• 39:16 - Jason’s closing reflection on unnecessary anxiety in money asks.

Final Takeaways

• Most of the anxiety around asking friends for money stems from overthinking and fear of social discomfort, not the actual outcome.
• Approaching with candor, context, and a light touch—plus using features like Venmo/Zelle requests—eases the conversation.
• Treating your friend as a collaborator against an outside inconvenience (the ticket/camera, not them) preserves goodwill.
• Odds are, your friends will surprise you with understanding and quick solutions, if you just ask.

For listeners facing a similar pickle: Trust your friendship, be honest and straightforward, and remember: it’s almost always less awkward than you fear.