Presenting Proxy with Yowei Shaw: Alex and the Impossible Ask

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Hi, I'm Alex Goldman, and this is Hyperfixed.

On the show, listeners write in with problems, big and small, and I try to solve them.

But this week, HyperFixed, the show itself, has a problem.

And no matter what we try, we simply have not figured out how to solve it.

So if you listen to independent podcasts with any regularity, you probably know that the podcast industry is not in the best shape.

Over the last 10 years, the podcast industry expanded beyond anything that many of us could have dreamed of.

And then the bubble burst.

Advertising dollars started to dry up.

Corporate cash began shifting away from narrative journalism towards celebrity-driven chat shows.

And then, one after another, all of our favorite audio shops began to close.

And our friends, some of whom I consider the best producers in the business, started getting laid off from their jobs.

And then they got new jobs and got laid off from those.

And then they got laid off from the jobs they got after those jobs.

Hyperfix producer Emma Cortland has been laid off four times in the past three years.

So what do we do?

Without corporate dollars, without reliable ad revenue, how does a show like Hyperfix make enough money to stay afloat?

Honestly, I don't know the answer.

But recently, one of my friends set out to answer this question.

Producer Yoei Shaw is among the hundreds of people I know who have been laid off in the past couple years.

You may know her as the one-time host of a phenomenal show called Invisibilia.

But when that show got canceled by NPR, Yoe started her own independent podcast called Proxy, which is kind of like a sibling to HyperFixed.

On her show, Yowe finds people with problems and then pairs them with the perfect person, or proxy, if you will, to address that problem.

And since she was having the same anxiety about money, she thought, hey, maybe we should make an episode about this.

So what you're going to hear today is the episode of Proxy where Yowei solves my problem.

We're like a problem-solving Ouroboros.

Maybe we'll just pass problems back and forth and we'll never run out of content.

Also, please be sure to subscribe to Proxy.

Mine is just one of a number of great episodes that Yowei's put together.

Other episodes include one where Brian Reed, the host of S-Town and Question Everything, tries to get over his incessant urge to correct his mother-in-law, who has Alzheimer's.

And in another, she tries to help two friends who were in an up-and-coming band that was derailed by a band member and a relative's death.

It's an incredible show.

Yoei is a fantastic problem solver and an amazing proxy hunter.

She's really got the goods.

You can actually hear the hope return to my voice as this episode goes on.

You can find proxy wherever you listen to podcasts and at proxypodcast.com.

But be aware.

Like me, you will probably hear Yoei at some point asking for financial support.

All right, here is the proxy episode: Alex and the Impossible Ask.

Thanks so much to Yowei.

Thanks so much to Proxy, and we will see you soon.

So, Alex, I asked this question of every guest: if you had to vocalize the sound of your emotional conundrum, what would it be?

Okay.

I think that's about it.

Welcome to Proxy.

I'm YoA Shaw, your emotional investigative journalist.

Today, the case of the two sad chumps who desperately want to do anything, seriously, anything, but the one thing they need to do to survive.

That's coming right up.

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Hello, Alex Goldman.

Hi, Yoe Shaw.

How's it going?

I'm okay.

I'm.

Why are you laughing?

I don't know.

That I'm okay sounded very qualified.

It sounded like there was an unspoken, I'm okay, but in there that you just didn't say out loud.

Well, that's a good segue because we are here today because we both need to solve the same problem.

Yeah.

Yeah.

So you and I used to work at big media outlets.

We had jobs with good benefits, regular paychecks, resources.

You were hosting Reply All.

I was hosting Invisibilia.

These were established shows with big audiences.

Yes.

And then that ended.

Yeah, and now we're out in the wilderness.

Yeah.

So you've started this new show called Hyperfixed.

I have this new show, Proxy.

Do you want to explain what HyperFixed, your new show is uh my show is listeners write in with problems it sort of doesn't matter what the problem is it could be an enduring family mystery it could be an interpersonal argument it could be some annoying system that people have to navigate and i try and help them with it and in doing so i hope that like I and maybe they learn something about the world.

And your show is proxy.

In some ways, I feel like proxy,

not to be a gender essentialist, but it's like the girl version of your show.

Proxy is all about feelings and what is your emotional hang-up and how can we make you feel better?

Whereas your show, a lot of it has to do with getting actual concrete answers.

That's a very funny way to put it.

Yes,

that's true.

Okay, so we have these new shows that we are funding completely independently.

And so, yeah, we both now have to ask for money all the time to survive.

Right.

Like, for instance, as of today, we're kicking off the proxy fundraising drive to get to 1500 paying Patreon members so we can keep going.

We live and die by patrons.

But here's our conundrum.

Alex, I know from talking to you that we both hate asking for money.

Part of the reason it took me so long to get this show started in the first place is because I was like, I really want to partner with a production company who will bankroll this thing.

So I don't have to be asking people for money.

I want to be be able to fund this entirely off of ads.

But that's just not the reality of almost any media these days.

Like that's just not happening anymore.

And like, I don't know for you, but like for me, I don't know what I'm doing.

I feel like I'm annoying people.

There's something about it that feels like deeply,

I don't want to say sleazy.

It's really.

Oh, it feels sleazy to me.

I feel like.

a grifter sometimes.

I'm like, oh, am I being a grifter right now?

I really believe in my show and think it should exist, but I just, I feel like a Bambi with shaky legs.

And also the stakes are really high.

Right.

You know, because if we don't succeed at asking for money, then our shows will cease to exist.

It's pretty terrifying, but so is the prospect of asking for money.

Yeah.

You know, when I was in college, I worked at a telemarketing agency for a summer.

My job was to like call people and say, hey, I'm calling on behalf of, you know, LGBTQ rights or whomever and ask people for donations.

And I do not have that skill.

Why were you not successful at it?

Because trying to convince people that they should spend money on stuff is like a thing that I desperately don't want to do.

I remember very clearly calling someone one time and then being like, why would you think it's appropriate to call me during my dinner time on a Sunday evening?

And I was like, I don't think this is appropriate.

I am doing this because I need to live.

I didn't even realize the extent of our similarities.

I also worked in telemarketing.

That was one of my gigs in college, calling alumni to donate to the university.

And I was terrible at it.

I'd get someone on the phone and be like, hi, this is Yowe.

I'm so sorry to bother you.

I'm so sorry for existing.

Sometimes I would like make the call and connect with someone.

And I could just tell by the tone of their voice that I was not going to make the sale.

And I just disconnect.

I like wouldn't even say hi.

You know, when they say like, this call may be recorded for quality assurance?

Uh-huh.

Sometimes my calls were being recorded for quality assurance, and they're like, why do you keep hanging up on people?

And I was like, I don't know.

I get scared.

Well, fate has decided that we are now stuck with a headset.

I know.

And this time, there is no end in sight.

Right.

This isn't the summer gig.

Okay.

So, specifically, let's talk about what are some of the emotional questions we need answers to.

I can say for me, I want to know what version of transparency is fun and brings people in and what version of transparency is pathetic and turns people off.

Right.

That's a very interesting question because I have defaulted to doing that.

My questions are just like, how do I feel okay with this?

I have this feeling like,

what makes you feel like you're worth spending money on?

Like how the unmitigated gall of asking other people to pay for you, to do anything.

It feels like an insane level of ego to be asking for that kind of thing.

And a thing that I've been thinking about a lot in the past couple of weeks is like,

if things get really bad, I mean, they already are really bad, but if they get much worse, like economically,

the first thing people are going to stop buying is their monthly podcast feed.

We are the discretionary spending.

Absolutely.

I've been thinking about this too.

And I want to know how to tell myself and to a degree, everyone else: hey, this thing is worth spending money on no matter what that's a really hard thing to feel in like a time where people feel desperate and scared yeah

okay

today we are going to tackle the great question of our age which is because everything is falling apart from public infrastructure to healthcare to how we fund news and science More and more of us are going to need to ask for money for all kinds of things.

And so is there any way to do it that isn't soul-crushing?

God, what a bleak question.

This episode will determine whether the shows exist or not in the future.

But no pressure at all.

No big deal.

Okay, I'm going to go and see what I can find out.

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That's

Alex, how long has it been since we last talked?

You're going to have to tell me.

I don't remember the answer to that.

It's been a while.

It's been several months.

Okay, so for me, a lot has happened since then.

I have talked to a lot of interesting people, and I want to start with someone that I found helpful for me.

Okay.

Her name is Haley Bash.

How are you doing today?

Wow, you are the second second person ever to ask me that question in an interview.

She wrote this book, Accidental Fundraiser, and she trains people just like us who really don't want to raise money, but have to.

And the weird thing about Haley is that she is very, very psyched about fundraising.

She used the literal words, really fun, to describe asking for money.

Oh, that's crazy.

So 15 years ago, Haley was living in San Francisco working as a software engineer and and was disturbed, not surprisingly, by the intense inequality she was seeing around her on the streets.

But she also felt powerless.

What could she, one person, do?

Right.

But one day she goes to an organizing meeting and someone asks Haley, do you want to help fundraise for local social justice orgs?

And even though Haley is terrified to ask people for money and hasn't really ever done it before, she says yes.

Okay.

Haley is so nervous.

She doesn't want to ask people directly or in person.

So she just sends a BCC email to 20 co-workers with a link.

And she's, she's panicking.

I am so embarrassed to go to work tomorrow.

Everybody is going to be gossiping about, oh, look at how greedy or presumptuous Haley is.

Wow.

She takes it harder than I think we do.

And we're asking for money for ourselves.

It's not like we're being altruistic here.

But I woke up the next day and I'd already hit my fundraising goal.

Oh, dang.

Okay.

In that moment, Haley is hooked.

It felt like I had agency for the first time.

You know, I felt very powerless in a lot of ways.

The tech world is so behemoth.

I'm a newcomer here.

I just met these co-workers.

But to see that, you know, despite all that sort of negative self-talk, that I was able to accomplish my goal so quickly, which I mean, goes to show that I was really lowballing what I could raise.

I learned more about goal setting later on, but it did give me the feeling of like, oh,

I can make a difference.

Okay.

For Haley, this early success tapped into an appreciation for fundraising that was lying dormant.

She grew up in a farming town in the Midwest.

And as a kid, she was always getting dragged to some spaghetti dinner or pancake breakfast.

You know, if someone got sick and needed help with medical bills, that sort of thing.

And for Haley, this is what fundraising is all about, building community.

There was kind of this unofficial, you know, especially for the families where it was the raising was because of tough times, you know, there was kind of like support circles around them.

What do you mean by support circle?

People just surrounding and hugging.

That's beautiful.

I mean, that's another thing about me is that I've always hated asking for help.

I've always felt like, no, I should be able to do this on my own, which is like a very toxic and actually pretty harmful way to think.

Yeah, same.

Okay, well, today, Haley is an executive director director of Donor Organizer Hub, this organization she founded to help people fundraise for under-resourced causes.

And something she's always doing in workshops is dealing with people's hang-ups about asking for money because people have a lot of them.

One person said in a training, apparently, they'd rather pluck out each of their individual nails than fundraise.

Yeah, okay, that sounds right.

You know, if you feel that way initially, it's like, congrats, you're human.

I still get the butterfly flutters when I ask people for money.

Hmm.

Really?

Yeah.

Yeah.

I think

that never goes away.

It never goes away.

I think.

Shoot.

Okay.

So the first thing Haley tried to do with me is reframe what asking for money means.

And she got a whole list of facts and arguments.

I'm going to hit you with some of the ones that stuck out to me.

Okay.

First reframe.

With funding cuts left and right.

Yep.

No universal health care, an affordability crisis, Haley argues that asking for money money is a first aid skill that everybody needs to learn.

A lot more of us are going to have to step up for ourselves and for people that we love.

That makes perfect sense.

It doesn't make it less bleak to me.

It does make me feel slightly less alone.

All right.

Second reframe from Haley.

When you ask for money, you are giving a gift.

Okay,

I'm interested to hear the explanation for that.

Haley says that most people think of asking for money as a favor, but you should think about it from the point of view of the person being asked, because you're actually giving them an invitation to get involved with a cool project.

Plus, she said there's lots of research that shows people feel good when they give money.

It activates the reward system in people's brains.

It releases the feel-good, happy chemicals.

And over the long term, it even improves mental and physical health.

It can lower blood pressure, reduce stress, boost self-esteem, combat depression.

I don't know if I would use this in my messaging exactly, but that does help.

This will salve my anxiety a bit.

Okay, good.

We're getting somewhere.

Here's the third reframe Haley made.

Are you ready for a mic drop moment, Yoe?

She said, asking for money is secretly the most popular thing ever.

She gave me this fact.

More people donate than go to church or vote or any other civic or community engagement.

Okay, well, that is a mind-blower.

I would not have expected that.

Why is it mind-blowing?

I just think about sort of the schedule on which I donate money and I do a decent amount when I can, but like, I'm just surprised at sort of that massive scale.

I was really surprised by this too, and it made me feel more hopeful.

Like, oh,

lots of people donate.

It makes it feel like less of an imposition to ask.

That's it.

It makes it feel more normal.

Here's the last reframe that stuck stuck in my brain.

Haley said that research shows that we underestimate the number of people who will say yes to us and how much money they will give to us, mainly because we're embarrassed.

Oh,

okay.

I mean, honestly, we're getting to the really encouraging stuff.

I'm sorry if I seemed underenthused at the beginning, but yeah, I appreciate this.

Well, Haley demonstrated this lesson by flipping the script and doing this role-playing thing where she asked me for money.

Alex, I'm going to do it with you right now if you consent.

I do.

Okay, so Alex, let's say I write a weekly newsletter reviewing synths.

Ooh,

I'm already on board.

So you love this newsletter.

You live for my articles about how to build modular synths at home.

I simultaneously feel like very called out by this and like very comforted.

It's like, you know me too well,

but also it's like, oh, I'm home.

Well, okay, you love this newsletter, but it's going to go under if readers don't give.

But because I'm a fearless synth newsletter writer, I'm going to ask you for a bold and ambitious, but not undoable amount of money.

How much money comes to mind?

I would say

$75 a year or like $10 a month.

What are the reasons you would say yes?

Because I'm getting information I can't get elsewhere, probably because I've developed a relationship with the author, that kind of thing.

Any other reasons?

Because I can afford it and I feel like things like that should exist.

And are there any other reasons why you would give?

I mean, I suppose, maybe, for some kind of bauble or benefit.

But I mean, the podcasts that I pay for, I often do not avail myself of all of the benefits okay what are the reasons you would say no

uh

what are the reasons i would say no that's actually much harder

um either i can't afford it or it doesn't interest me enough or i'm already supporting other things that take up a significant chunk of my income

Any other reasons you would say no?

Not that I can think of off the top of my head.

Okay, so this this is the part where I'm trying to be Haley right now.

What did that exercise teach you about asking for money and what it feels like to be asked?

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.

Did that do anything for you or not really?

It did.

It moved the needle a little bit because it made it feel like, oh, okay, well, I mean, I have so little problem doing this and I like supporting things that I care about.

Maybe I should be a little more chill.

That can be the secret title to this episode.

Maybe we should be more chill.

Okay,

so I want to tell you about this other thing that Haley did with me because it was really funny, but also disconcerting.

There were times when talking to Haley where it felt like I was being inducted into a cult, especially when she would say things like, what if fundraising is living into exactly the purpose of why you have proxy?

See, that kind of language is really tough for me.

It just sounds so insincere.

And so it sounds very corporate speak to me.

But I also totally understood when talking to her why I would want to join this cult.

I felt like I was in a chair and Haley was like cheerfully breaking me down.

Okay.

She'd ask me questions like, what are you hoping to to overcome?

What do you want to be courageous about?

What's in your control?

Do you have control over whether they're busy?

No.

Is it likely that people think you're uppity for asking for money?

No.

Are people likely giving when they shouldn't be?

No.

What happens if you take away that agency from people?

Maybe it's condescending.

The fear of uppity

becomes realized.

Haley.

Alex, I'm going to put you in the chair.

All right.

Put me in the chair.

You're in the chair.

So, Alex, what's your worst fear if you ask for money?

My worst fear is that people will

not only not want to give me money, they just won't want to listen to the show anymore.

How likely do you think this is going to happen?

I think that you're going to tell me that it's not super likely, but like in my head, It's like if I ask more than once a month,

in a more meaningful way than just saying in the end of the episode like hey you know we've got a premium membership

if I do it like more than once a month in any meaningful way people are just gonna be like go away you are so annoying what is your problem

is minimizing annoying people the point of life

Wow

that's a really big question

I feel like I'm doing a terrible job at this because I have all of the same fears.

When Haley did this with me, though, she flipped the whole question around in a nice way.

Let's say six months from now, Yowei, I'm so sorry.

The unfortunate news is proxy was not able to fundraise the amount needed to sustain itself.

And so you have to announce closure to your listeners.

Do you think your listeners might be annoyed that you didn't ask for money, that you didn't say you needed support?

I mean, that's very fair.

But it's like, it's just a really tough balancing act.

Yeah.

Now for the lesson that completely flips the way I've been asking for money and the way you've been doing it.

I can hardly wait.

Alex, you sent this earnings report email back in May.

Do you remember the one I'm talking about?

Yes, I do.

So this is that email where you break down the business model for making money in podcasts and how you hyperfix where you're at six months in with audience growth, membership subscription, and ad revenue, and how far you have to go to be sustainable.

Can I have you do a dramatic reading of one paragraph?

Yes.

Okay, I send it to you.

Oh, I love doing dramatic readings, especially of my own writing.

I've agonized over whether or not to publish this.

Well, agonized is a little strong, but I've definitely waffled.

I think that openness and honesty, even at a level that makes me uncomfortable, is to some degree what people like about my work.

I also genuinely want to help people understand the cost of making real narrative journalism in 2025 after the advertising market has contracted, after companies like Gimlet have all cashed out.

I feel very confident that there's a way forward.

It's just taking longer and requiring me to take on more financial liability than I'd hoped.

And things could definitely turn.

But I could also have to go get a real job instead of telling stories on the internet.

And if I do, hey, I had a good run of almost 20 years and I feel very fortunate.

So I shared your email with Haley, and she thought there were parts of it that were great.

Like transparency in theory is great.

Uh-oh.

But she was like, I feel like y'all are collectively sharing the recipe, not the brownie.

A lot of talk of, you know, it's hard.

And it is hard.

Like, I don't want to, you know, minimize how hard it has been, these shifts have been for you all, but it's like, it's hard to be an independent podcaster out there.

And it just all kind of feels like, ooh, okay, so it's hard to pay your bills, y'all.

That sucks.

I'm so sorry.

Versus, like, I am a participant of something bigger, more beautiful.

It's connected in my day-to-day routine.

Churches, they call it tithing, right?

Like religious communities, they ask for a certain percentage of your income.

They pass the bucket.

They give you the gifts of God, right?

And I'm not saying you have to have the stakes of like God.

I think I get it.

I think I get it.

Her point is, if you're always talking about the baking powder, the sugar, the flour, the eggs, nobody's mouth is watering.

You have to talk about the delicious, gooey brownie that people will get to eat.

Like, say you have a fundraising campaign to save save the aquarium.

If you're focusing on the recipe, you're going to talk about saving the staff, you got to pay rent, property taxes.

But Haley says the brownie would be talking about the jellyfish and the cool sharks.

Like that's why people are going to give to save the aquarium.

I understand.

I get what this makes perfect sense.

I do think that like me talking about the difficulties and stuff is very in line with my like constant apologizing for doing it.

Um, it's like me being like, I'm sorry, but we really need this because of this, this important thing.

Whereas I think what you're saying is, I should just be like, hey, here's the great benefit of doing this.

My mind was blown by this, and I was not entirely convinced, but let's just go with it for a bit.

Alex, do you have a proudest or favorite moment from HyperFixed?

I don't know if I necessarily have a proudest moment, but there's like

these little, I feel like there's always just like little little touches where I'm just like, oh, I love this.

I'm so glad that I get to be a part of this thing.

A perfect example would be the most recent episode we did.

It was a guy who came to us and was like, hey, I have aphantasia, which is the inability to create images in your mind's eye.

Like if someone says, imagine an apple, you see nothing.

Abstractly, you know what an apple is.

You don't.

You can't visualize an apple.

And this guy had this condition.

But the thing that, the thing I really liked about that conversation was this incredibly human fear this guy had that if his dad died, he would forget his dad.

But like, I feel like I should be able to think about his face and I just can't, you know?

The whole reason Mitchell wanted to fix his aphantasia was because he wanted to do that magical thing everyone else seemed to be able to do, to carry their loved ones around with them.

And in particular, he wanted to carry his dad.

So after our interview, I was just like, oh, that's really touching and so utterly relatable.

What would be the brownie here for the listener?

That's tough.

More episodes like that one.

What is that episode doing for people?

Oh, man.

You're really putting me through the paces today.

I'm only speaking for myself here.

It presents like a worldview that makes me feel a little less alone.

If it makes you feel any better, I was also just like,

I don't know how to answer that.

Haley.

Because like, you know, it's like fundamentally hard to put yourself in in someone else's shoes.

Right.

And also it feels like a little egotistical.

That is hard.

It feels like you're writing a grant of like, here's all the impact, the measurable ways that this show is helping people.

Yeah, I don't know.

I don't think about the show as like helping people.

I'm sure that I've done some service journalism here and there that's made a difference, but I think of the show more in terms of like, this will make them feel something.

And I suppose that's helpful.

For me, well, if I had to first talk about a moment, a favorite moment, it's hard to choose one, but I would say in every successful proxy conversation, there's this like moment where the tension in the room gets released just a bit.

And it can come from someone saying, I'm sorry that happened to you.

That shouldn't have happened to you.

Or, you know, someone sharing a similar experience to be like, I see you.

I get it.

Jesus fucking Christ is my first thought here because like, I have terrible layoff stories that I've been told that I've seen where people just like show up and their emails are disabled or the doors locked or like they come and, you know, their fate is decided by which color card they pull out of a box.

Like there's crazy shit that I could tell you about.

Your story is the least human story I've ever fucking heard.

Like that is.

horrifying.

And I am so sorry that this is what happened to you because this is just like a series of poor decisions where this company decided that you were not a person and that you didn't matter.

And that's not okay.

But I just honestly want to apologize on behalf of all people professionals for how that person acted

and how the company empowered that person to act.

Thank you.

I appreciate that.

So Haley is saying, if you can remind people of these rare, special moments and things that you're doing for listeners that exist exclusively because of the podcast, then thinking about it not existing might be more painful to listeners.

As if you were to say suddenly, no more brownies for life, never again.

Okay,

Here's the last thing that Haley told me that I want to talk about.

She said to watch the vibes.

What does that mean?

Okay, so Alex, one of your hang-ups was worrying about being egotistical, feeling bad about asking when people don't have as much money these days.

That whole hangup of like, do I deserve money?

Haley is like, that is just faux modesty, and it's not helping.

I think when we have fears of embarrassment, we prepare for ourselves for rejection ahead of time and we try to short code it for people to reject us.

She compared it to asking people to go to a party.

So, Alex, if I were to ask you,

hey, there's this party happening this Friday, but it's, it's probably not going to be that fun.

Um, I don't know how many people are going to be there.

And like, you probably have more important things to do.

would you want to come to my party

uh

okay fine fair fine no

okay

besides being insecure haley said that we both seem very sad and that is also not the right energy to bring to fundraising

okay yeah but i mean that's also just like my default

i gotta get over that i think haley says sadness is not the right way to ask.

You have to tap into what is the thing that made you, Alex, want to go into debt to make HyperFixed?

Like, what lights you up about the show?

Untangling problems is so exciting for me.

I love doing it.

So being able to...

answer questions that people have and being able to make the world feel a little more mappable.

All of that is very exciting to me.

For me, you know how you said earlier that your journalism isn't really about helping people?

For me, I would say that is my kink.

Like I love to be useful and I am convinced that emotional investigative journalism is special and important

and I love helping people report on their feelings.

It feels like a magic trick.

Like, yes, you can go to therapy.

Please keep going to therapy, everybody.

But, you know, your therapist isn't going to scour the world of social science to see if there's an insight that would be useful for you.

They're not going to look for the exact right stranger who has shared experience that would be useful for you to talk to.

And then on a more macro level, I just feel like we're not taking emotions seriously enough.

I feel like we've reached the point in the culture where we're like, yes, we have feelings and we need to regulate them.

But what are the the specific underlying emotional dynamics driving personal problems, relationship problems, social problems, political problems?

I feel like that's a lens and layer that often gets overlooked in journalism.

That's my thing.

Yeah, okay.

I feel like a little nerdy when I say these things.

No, I think that this is all very useful.

I'm feeling for the first time like, okay, maybe I should just swallow all of this goofiness and be a normal person.

After the break, any progress we've made goes out the window.

We have a fundraising catastrophe.

That's when Proxy returns.

Alex?

How you doing?

Okay, so the other day you said something scary happened with fundraising.

We talked briefly about it, but walk me through what happened because I don't really understand.

All right.

Well, let me try and explain it to you.

So like I have talked to people who you how to raise money and I've been doing it a variety of ways.

You know, I ask on social media every once in a while.

I will put maybe a minute long thing at the beginning of the podcast, reminding people that we're independent and asking them to support us if they can.

I'll put things in the credits about what kind of bonus stuff they will get.

Another way I've been trying to monetize, and I hate, God, it feels so icky.

in my very soul to talk about monetizing.

But I mean, that's just like where we're at as an industry.

So another thing I've been trying to do to monetize is we've partnered with a company called Podroll.

And basically they say, hey, what if we throw an episode of another show down your feed that will appear after your most recent episode?

So it's basically like.

You're giving ad space to other podcasts in the form of having them be the second episode on your feed.

And then the rest of the feed continues normally.

And the feedback from our listeners on all of this has been resoundingly negative.

We released the second part of a three-part series earlier this month, and I put an ask at the beginning of that.

And like

the hostility for that, it wasn't anything that I hadn't done before, but the hostility to it was like really strong and it really spooked me.

And I don't know what I did differently necessarily.

That fucking sucks.

I'm sorry.

Have you gotten negative feedback like this before about asking for money?

No, I don't feel like I had.

I feel like I had six months months of runway or something.

And then people were just sort of like, I don't really want to hear about this anymore.

And I'm wondering if it's just like they find me grading, which I don't know if there's a cure for that.

Let's not go there yet.

And I mean, for what it's worth, we can see how many people sign up on what day.

So we can roughly calibrate what's working and what's not.

And if it had been a thing where like we got massive conversion at that moment, like it was like suddenly a bunch of people signed up, I would be like, well, okay, there's a vocal minority of people who are annoyed, but also I am proving materially that this works.

Yeah.

But I did not see that.

And what are they saying exactly?

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 that it was this or that.

Wow.

Your listeners take a lot of ownership over your feet.

I generally think that like people who feel passionately about a show, even if it's like they're really mad about something, it means they care.

Yeah.

And so have you asked for money

since getting this response?

I said, you know, sign up to get bonus episodes and Discord access in the credits of this week's episode, but

not really.

And what are you going to do about the next episode?

Are you going to ask?

I'm not going to ask.

You're not going to ask.

No.

Damn.

Okay.

This is spooking me a little bit too.

I'm sorry.

No, no, no.

It's okay.

This is where we're at.

And do you know what you're going to do?

I haven't exactly figured out what I'm going to do.

Right now, I'm in a holding pattern.

Okay.

I am sorry this is happening, and I am going to try to find something useful for you.

Well, thanks so much, Yahweh.

Let me know if you need anything, okay?

Hello.

You.

So, Alex, last time we talked, you told me about this fundraising debacle where you got spooked by listeners getting mad at you for asking money, and you were holding off on fundraising because you didn't know how to like proceed, even though you need to keep asking for money.

Yes.

Well, since then, I ended up having a really illuminating conversation with someone about exactly the dilemma that you're having.

And I think I have answers.

Oh my God, I'm very excited because I feel like I'm bad at this.

So, funny story, but when I was talking to Haley, at one point she said, Well, I can tell you anecdotally why Alex's pitch isn't working.

And that's because my spouse is a big, hyper-fixed fan and has not been moved to give to the show.

Like, he doesn't understand why he he needs to.

God.

Come on.

Okay.

So Haley's spouse, his name is Danny Henn.

Okay.

And I didn't even know if he would say yes to talking because it's like a fundamentally kind of awkward ask.

But Danny was down to be honest about it all.

Well, it is kind of an interesting situation of being the person who's not doing the quote unquote good thing.

Look, as much as I am anxious about what it means to be honest about my ask, I really want to know the answer here.

Okay.

So Danny is a small business owner.

He manufactures pots and pans.

And he says he's actually thought quite a bit over the years about why he hasn't given to any podcast yet, even though he listens to them a lot.

And he has a couple theories.

Okay.

Number one, podcasts are free.

It's a free rider problem.

It's a free good out there.

So Danny doesn't live under a rock.

He's noticed that there have been a lot of changes in our industry in the way podcasts can and can't be funded.

But he's been getting podcasts for free all these years, and he hasn't been trained to put podcasts in his monthly budget yet.

Right.

He does support two Patreons right now, two extremely small niche projects, a data visualization project and a cookbook reviewer.

But when it comes to podcasts, Danny says it's hard to tell who is big podcasting and who is small podcasting because they can can sound really similar and they all show up on the same app.

And he doesn't want to give his few extra bucks a month to podcasts that are already massively successful and raking in the profits because they don't need him.

He wants to give to small podcasts where he feels like if he didn't give, they might go away.

And who could blame him?

When I heard Danny say this, it felt like kind of the curse, a curse for us.

Because like we have these standards and years of training from working at Invisibilia and Reply All and other places.

So we make podcasts that sound like they could be big podcasting and sound like we have a lot of resources, even though we don't.

Yeah.

When really like we're the lemonade stand of podcasting.

Basically, yes.

So Danny says, yeah, just be clear about that.

I would also sort of approach it from a like marketing perspective of like, we are the little guy that needs your support.

We are different from these other big podcasts or podcasting companies or whatever.

We are doing this project in a different way.

So that was his second reason for why he doesn't give.

Third reason, and this is where shit kind of gets controversial.

Danny was like, I want to know all about the recipe for the brownie.

He wants to know about how much ingredients cost, your signature way of baking the brownie, what pan you're using, how much are you selling the brownies for?

How do you even make it in the cold hard brownie business?

Oh my God, I'm more lost than ever now.

I was like, Danny, you do know that you're directly contradicting the fundraising expert in your family.

And he was like, Yeah, I'm sorry.

I'm just telling you what I, what I think and feel.

And the other thing that happened was like, when Danny said this, I was like, what more transparency do you want from Alex?

He just did that earnings report email in May.

And I was kind of getting annoyed, honestly,

on your behalf.

I was like, I appreciate it.

come on man yeah danny get his ass

and it turns out danny had missed your email oh oh well that i may have missed so i sent him your email did it move him before i tell you his reaction i'm going to tell you my honest reaction to your email which i have not told you yet Okay, so I was very impressed and grateful for your transparency as a fellow podcaster.

But I have to tell you, I was was kind of like, this is pathetic

to be like, woe is me, poor me.

Yeah.

Well, and personally, I've been trying to get away from that vibe, trying to get away from like all the numbers and being a bummer.

So I asked Danny, didn't you find the vibes annoying or kind of pathetic in Alex's email?

Sorry about that.

Yes, a perfectly reasonable question.

And he was like, no.

If anything, it made me want to give more.

I think he's being open.

He's being vulnerable.

He's being like, eh, I don't know if it's all going to work.

And that's a little scary.

Which is perfectly reasonable.

I hashed this out with Danny because I think that I'm having an outsized negative reaction to your email.

You know, like when something bothers you about you and then you see someone that like reminds you of your wound and then you're like, oh, get me away from this person.

Yes, I do.

I know exactly what you're saying.

But Danny was like,

no, this exactly scratches my itch.

This is exactly what I needed.

Huh.

He got to the end of the email and he was like, yeah, I'll sign up.

I've never been closed off to it.

It's not like I'm trying to like, you know, viciously protect my pocketbook from any of these expenses, but it is kind of like without some real impetus.

And like, maybe right now, this is my real impetus, right?

Right.

Being interrogated about why you don't give.

Yeah.

And that's not typical for a listener.

Oh, now I'm more confused than ever.

It was very confusing for me because

my real question this whole time is like, how transparent should I be with where my show is at and my feelings about it?

You know, like in this fundraising campaign I'm doing right now, should I be realistic with my Patreon member goal?

Or should I ask for what I actually need to make the show sustainable?

I talked about all this with Danny, you know, that I'm willing to do almost anything to make this show work because I love it so much.

I believe in it.

Also, I'm working all the time and it's like really hard.

I work almost every night, every weekend, and I never see my friends and family.

And I feel like I'm definitely taking years off of my life because of the toxic stress and lack of sleep.

I've used all my savings.

I'm really shooting my shot here, and I'm scared.

And for Danny, he was like,

that's what I needed to hear.

For me personally, giving like, this is my last big shot, I think that does help push.

And, you know, if

you can start your fundraising drive here with one,

I mean,

that's, you know, I value your podcast.

And now, obviously, you know, not everyone gets to talk with the podcaster and talk through these, you know, thoughts and fears.

But like having that full context, you know, sure.

Yeah.

Convinces me.

Wait a minute.

Did I just get your vote?

You got my vote.

Oh my God.

Wow.

I wasn't even going to try to get you to sign up for my patron.

I was just going to try to get you to give to Alex's show.

That's very kind of you.

Basically, the way that I've been dealing with the vibes question is to just

not be real about my feelings on the show when I make my fundraising asks and to do it sideways with like a wink because I'm like I don't want to be a bummer but like talking to Danny I'm like oh me being real about my feelings when I'm not even like making a pitch to you that was the thing that did it I mean I guess a question I would ask you is like

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, right?

That you didn't put it all out there

when it was your chance to put it all out there.

But you know, I was like, Danny, were you already gonna support our shows when you said yes to this interview?

Well, I think I went, I wouldn't agree to it unless I was open to it, right?

I also like, I don't want to be that person who's like,

you know, the freeloader.

Danny was like, I was probably predisposed to give.

Okay.

But he said, so are your listeners.

They are also predisposed to support your shows because they're listening to you.

They're signing up for this experience.

That's a good point.

Damn, Danny's bringing sage wisdom.

Give it up for Danny.

Okay, so Alex, let's zoom out.

Where are you at now?

I mean, still terrified.

I still hate asking for money, but like, I feel like I have a direction, at least.

Really?

I do feel like there's a component of trying to be honest about where I'm at, not sounding desperate, but being realistic.

But then also maybe reminding people of the reasons why they listen, as opposed to just being like, if you don't do this, it's the end of my career as a journalist.

And

as for your fundraising debacle, the listeners who got mad at you, I talked to Danny about what happened and how you got spooked.

And he was like,

fuck the haters.

Or in his words, ignore them.

I think if you really

like let those people govern how you approach this, you're like, I don't know, that's really scary.

There's going to be naysayers.

There's going to be people upset about whatever.

And

let them.

All right.

Yeah.

Yes, I will just be more resolute and maybe like a little more positive.

Okay, so here's where I'm at at the end of all this.

I feel less bad about asking for money.

Haley's reframes have helped me.

Though I think it's still hard to think about I'm giving listeners a gift by asking.

I think the gift is the actual podcast, but whatever.

I think I am going to be more transparent about the recipe and where things are and not worry so much about being a bummer.

I also try to talk about the brownie more.

And because of that,

I don't feel like a terrified mouse telemarketer anymore.

Yeah,

I think that the brownie thing actually has really helped me.

I need to talk.

Ring, ring.

Hello.

Oh, Alex, I think you're getting a call.

Yeah.

Hi, this is Alex.

Hi.

Is this Alex Goldman?

Yeah.

This is Yowei Sha from Proxy.

How are you doing today?

Oh, my God.

I'm doing great.

Thank Thank you so much.

You're a fan of the show, right?

Yes, I am.

Okay, and you know how you were feeling alone and panicked with your feelings about asking for money?

Well, the whole point of the show is to help you report on these confusing feelings and help you get a little less stuck.

Oh, okay.

Listen, we've started to sell some ads, but they're a drop in the bucket.

And we do have around 400 paying Patreon members right now, which is amazing.

But that doesn't cover the costs of making the show, which is why we need to get to 1,500 paying Patreon members this month to keep the show sustainable for year two.

So, Alex,

what do you think?

Oh my God, Yoe, you're very good at this.

Hold on, I'm signing up.

We, wow, I really didn't have to try that hard.

I was going to.

I tried when you gave it, it was good, and like I'm predisposed, right?

I guess for all the listeners out there the question is imagine if both hyperfixed and proxy exploded in the sky never to be heard from again wouldn't that be a sad cold world it would be a sad cold world but also we'd go out with a bang because we tried um okay i think my work here is done wow damn good work dude Thank you very much, Joey.

I feel much better now.

I mean, not much better.

I feel 30% better, which is a massive improvement over what I was feeling.

That was Alex Goldman, the host of HyperFixed.

Listen wherever you get your podcasts and consider supporting the show by becoming a premium user.

Thank you to Haley Bash of Donor Organizer Hub for giving us advice.

She's the co-author of the book Accidental Fundraiser.

We'll have that link in her show notes.

And thank you to Haley's spouse, Danny Henn, for deciding to not be a podcast freeloader anymore.

And if you get something out of this show, consider joining the proxy Patreon starting at $5 a month.

Just go to patreon.com slash proxypodcast.

Okay, guys, I'm going to give it to you straight.

As some of you know, I started proxy last year because I got laid off and NPR canceled my old show, Invisibilia.

From the beginning, I knew it was gonna be a long shot.

In fact, a bunch of people I respect in the industry, even some friends, told me I couldn't make an independent podcast work today for a couple reasons.

Number one, advertising revenue for podcasts and media is down hugely.

And to sustain a podcast with ad dollars, we'd need to reach hundreds of thousands of people.

Which brings me to number two.

It's notoriously hard for audio-first podcasts to find their audience.

There isn't a good recommendation algorithm, and I don't have bags of marketing cash to spread the word about the show.

But here I am, a year later, and we're doing it.

I use my savings.

I got a loan.

I started a Patreon.

And since last May, we've made 20 episodes and 13 exclusive premium episodes.

Episodes about the mental toll of layoffs, the emotional dynamics of support groups, WTF is up with the inner narrator in our heads, band drama, caring for a loved one with dementia, on and on.

And against all odds, we are finding our people.

We've charted at number two in science on Apple Podcasts.

We've made it into the top 200 podcasts in the world.

I believe in this show.

I know lots of other people do too.

Emotions rule our world, and we need to rigorously report on them.

But in order to make a year two in a way that's sustainable for for me, we need to get to 1500 paying Patreon members.

Currently, we're at 400, which is amazing.

And recently we got some grants, which is also amazing.

But it still doesn't come close to what we need.

This year of proxy was possible because I had part-time production help early on.

And you'll get to hear an ambitious project we did together coming up that I'm really excited about.

But for most of this year, it's been mainly me making the show with an editor who edits a handful of hours a week, and I make my husband mix the show for free.

So that's me doing the research, looking for proxies and experts, scheduling and prepping questions and conducting interviews, cutting audio clips, writing scripts, producing, editing, and scoring and pro tools, and a million other tasks.

In any halfway normal podcast, This is work done by several people.

And for me to continue this work, I need help.

This is why we need to get to 1,500 paying Patreon members, because with grants, that'll cover the cost of making a year or two and allow me to get some part-time production help.

It's an ambitious goal for us.

I'm not going to lie.

I was told that maybe it's too ambitious.

But I'm taking Danny's advice and being honest about what we need.

All right, that's enough recipe.

Let's talk about the brownies.

If you join our Patreon, starting at $5 a month, your first brownie is, well, you've already tasted your first brownie.

If Proxy has helped you feel less alone, made you laugh, cry, feel things, helped you move through the world a little lighter with a little less confusion, that is the delicious, gooey brownie you'll get to keep eating if you sign up.

Second Brownie, Patreon members get exclusive premium episodes and ad-free episodes.

Plus, you get to join our chat.

Third brownie, anyone who has an annual membership by the end of this month-long campaign will get an original magnet made by me.

I love making magnets.

If you are able to, annual memberships really help us because more of your support goes directly to us than monthly credit card fees.

You get to eat all those brownies at patreon.com slash proxypodcast.

And of course, to our early Patreon supporters, thank you for getting us here so far.

This episode was edited by Tim Howard, mixed by Kyle Pooley, and produced by me with help from Charlie Klein.

Music in this episode by Tim Howard and our theme music is by Breakmaster Cylinder.

Special thanks to the Independent Media Initiative, the Berkeley Greater Goods Science Center, and the John Templeton Foundation for supporting the show.

Proxy and HyperFixed are proud members of Radiotopia from PRX, a network of independent, creator-owned, listener-supported podcasts.

Audrey Martovich is the executive producer of Radiotopia.

Yuri Lazordo is the director of operations.

Discover audio with vision at radiotopia.fm.

As always, you can follow us on Instagram at proxypodcast, and I'm at YoA Shaw.

Get in touch at proxythepod at gmail.com.

Thanks for listening.

I am so grateful to everyone who's been tuning in, who's commented, shared, wrote in.

And we've got some real bangers coming up for you during the drive about estrangement, doppelgangers, and more.

See you next episode.

Radiotopia

from PRX.