Proxy with Yowei Shaw – Episode Summary

Episode Overview

Title: Alex and the Impossible Ask
Date: September 9, 2025
Host: Yowei Shaw
Special Guest: Alex Goldman (Host of Hyperfixed)

In this candid and insightful episode of Proxy, journalist Yowei Shaw and fellow independent podcaster Alex Goldman dig into one of the most awkward, anxiety-inducing aspects of running a creative endeavor in 2025: asking your audience for money. Both Yowei and Alex used to enjoy stable jobs at award-winning podcasts (Invisibilia and Reply All respectively). Now, as independent creators, they discover how hard, vulnerable, and existentially confusing it is to fund their new work—and grapple with the personal shame and practical dilemmas of “the ask.” Along the way, they get guidance from fundraising pro Hailey Bash and an unexpected perspective from Hailey's husband, Danny. The episode unearths new ways to view fundraising, blending emotional self-examination and practical strategies, all while maintaining the show's trademark humor and vulnerability.

Key Discussion Points & Insights

1. The Unique Pain of Asking for Money

• Transition to Independence:
  Both Yowei and Alex recount leaving high-profile jobs (“out in the wilderness now”) and having to construct and fund new podcasts entirely on their own.
  Yowei: “Now we both have to ask for money all the time to survive.” (06:10)
• Emotional Toll:
  Expressed discomfort, shame, and impostor syndrome about asking listeners for support.
  Alex: “It feels like an insane level of ego to be asking for that kind of thing.” (09:04)

2. Telemarketer Trauma and Fundraising Dread

• Both have a history with telemarketing and detail how it made them extra wary of being “annoying” or “sleazy.”
  Yowei: “I’d get someone on the phone and be like, ‘Hi, this is Yowei. I’m so sorry to bother you.’” (08:16)
  Alex: “I just disconnect… I’d get scared.” (08:36)

3. Philosophical & Emotional Questions About Fundraising

• What version of transparency is engaging? What is off-putting?
• How do you believe your work is worth asking money for, especially when it’s a tough economic time?

4. Expert Advice from Hailey Bash ("Accidental Fundraiser")

• Reframe #1: Asking for Money is a Survival Skill
  More people will have to do it as institutions falter (17:24).
  Hailey: “A lot more of us are gonna have to step up for ourselves and for people that we love.” (17:33)
• Reframe #2: Asking is Giving
  You’re inviting someone to be part of something, and giving can be pleasurable.
  Hailey: “It activates the reward system in people’s brains… improves mental and physical health.” (18:14)
• Reframe #3: It’s the Most Popular Civic Activity
  Citing data: more people donate than go to church or vote. (19:01)
• Reframe #4: You Underestimate How Many Will Say Yes
  We let embarrassment cloud our judgment—don’t take away people’s agency to help.

5. Role-Playing and Practical Exercises

• Yowei role-plays an ask with Alex, uncovering that giving feels good, and refusing typically only stems from genuine limitations, not annoyance. Alex: “It’s much easier to get me to donate to stuff than I thought it would be.” (22:10)

6. The Recipe vs. the Brownie Metaphor

• Danger of Being Too Transparent:
  Hailey warns that always sharing the “recipe” (the hardship or logistics) makes the ask less compelling than making the audience crave the “brownie” (the joyful result).
  Hailey: “Y’ all are collectively sharing the recipe, not the brownie.” (27:02)
  Yowei: “You have to talk about the delicious, gooey brownie people get to eat.” (27:45)

7. Celebrating the Show’s Value—the “Brownie”

• Both hosts reflect on the most affecting, connective moments in their shows, such as:
  • Hyperfixed: “It presents, like, a worldview that makes me feel a little less alone.” (30:11)
  • Proxy: The moment a listener feels genuinely seen and less lonely.

8. Managing the Vibe: Avoiding Sadness and Faux Modesty

• Energy Matters:
  Hailey compares apologetic asks to bad party invites.
  Yowei: “Would you wanna come to my party?”
  Alex: “No.” (34:10)
• Tap Into the Spark:
  Ask with the genuine energy that made you start the project, not with sadness.

9. Fundraising Setback and Listener Pushback

• Alex describes how listeners pushed back angrily at repeated asks and “pod roll” (cross-promotion) efforts, discouraging him from further fundraising. Alex: “The hostility to it was, like, really strong. And it really spooked me.” (38:50)

10. A Listener’s Point of View: Danny Henn

• Barriers to Giving:
  • Podcasts feel like a “free good.”
  • Hard to tell who are “big” vs “small” podcasts.
• The Importance of Specific, Honest Context:
  • Danny, a small business owner, says knowing the vulnerability and reality behind a show makes him more likely to support. Danny: “He’s being open, he’s being vulnerable…that’s a little scary. Which is perfectly reasonable.” (46:35)
• Listeners Are Predisposed to Support:
  Danny: “So are your listeners. They are also predisposed to support your shows because they’re listening to you.” (50:28)

11. Advice Moving Forward

• Be honest without being desperate.
• Remind people of the “brownies”—what they love about your show—when you ask.
• Ignore the haters; don’t let the vocal minority define your approach. Danny: “If you really let those people govern how you approach this…that’s really scary. There’s going to be naysayers…” (51:33)

Notable Quotes & Moments

• On the central discomfort:
  Yowei: “I feel like a Bambi with shaky legs. And also, the stakes are really high.” (07:08)

• On getting more comfortable with the ask:
  Alex: “It taught me that, like, I’m pretty willing to give, and that it’s much easier to get me to donate to stuff than I thought it would be.” (22:10)

• On transparency and the “recipe”
  Hailey: “Y’ all are collectively sharing the recipe, not the brownie.” (27:02)
  Yowei: “You have to talk about the delicious, gooey brownie that people will get to eat.” (27:45)

• On bringing the right energy to asks:
  Hailey: “When we have fears of embarrassment, we prepare ourselves for rejection ahead of time, and we try to shortcode it for people to reject us.” (33:31)

• On receiving angry listener feedback:
  Alex: “They’re saying, like, I can’t believe I had to sit through another hyper fixed ask for money. I wish that it wasn’t so long…Or I wish it was this, or that.” (39:39)

• Listener perspective:
  Danny: “If at the end of this you don’t find a sustainable path, would you be more upset that you didn’t share the whole thing? That you didn’t put it all out there when it was your chance to put it all out there?” (49:57)

• Asking with joy, not apology:
  Yowei: “I don’t feel like a terrified mouse telemarketer anymore.” (52:39)
  Alex: “Yeah, I think that the brownie thing actually has really helped.” (52:43)

Timestamps for Key Segments

• Opening Emotional Conundrum Sound Effect – 00:00
• Transition from Big Podcast to Indie & Introduction to the Dilemma – 04:54–07:30
• Dissecting Why Asking for Money Feels Sleazy – 07:31–10:26
• Setting Up the Expert Search – 11:01
• Interview with Fundraising Expert Hailey Bash – 13:25–25:04
• The “Brownie vs. Recipe” Metaphor & Its Implications – 27:00–30:43
• Role-Playing Fundraising Asks & Reflecting on Giving – 20:03–22:36
• Discussion of the Right 'Vibes' for Fundraising – 33:10–35:02
• Alex's Fundraising Setback & Listener Pushback – 37:10–41:05
• Listener/Non-Donor Perspective from Danny – 41:05–51:19
• Summing Up Lessons and Embracing the Ask – 51:20–end

Final Takeaways

• Asking for support is emotionally fraught, but can and should be reframed as an act of community and invitation, not imposition or shame.
• Transparency is crucial but should be balanced with celebration of what the show uniquely offers—the “brownie,” not just the “recipe.”
• Irate listener reactions are often a vocal minority; don’t let them scare you away from asking.
• Many listeners are “predisposed” to support you—they just need authentic context and a clear ask.
• Bringing genuine energy and clarity, rather than apology or sadness, makes a big difference.

Concluding Reflection

The episode ends on an empowering note. Both hosts embrace a more open, joyful, and direct approach to asking for money, acknowledging the vulnerability but also the unique value of what they produce. With practical advice and emotional support, Yowei and Alex experiment with being less apologetic and more celebratory about the “brownies” they bake for their communities.

Recommended Actions

• If Proxy or Hyperfixed has ever made you feel seen or less alone, consider joining their Patreon.
• When you ask your audience or community for support, focus on the bigger “why” and share the rewards—not just the challenges—of participation.

Episode produced by Yowei Shaw with editing by Tim Howard. Special thanks to Hailey Bash and Danny Henn. For more, visit ProxyPodcast.com.