I heard a podcast recently that was themed around “How to Ask for Money”. I don’t think there’s any podcast that doesn’t ask for money or promote a Patreon or live ads or whatever. But as I listened, I thought these are crossover skills with author promotion.
If you’re an author doing a book signing or during a release, you have to do a lot of marketing by yourself. You have to be a salesman, at least that’s what I’ve observed. And I hate being a salesman. Selling is convincing people to do something they didn’t want to do in the first place. And that often involves, if not outright lying, then enough exaggeration and hyperbole that there’s no difference. Selling makes me feel bad.
So these are the notes I’ve gathered/coagulated from that podcast in the hopes they might help you.

What version of transparency is fun and brings people in? What version is pathetic and turns people off? What makes you feel like you’re worth spending money on? It feels like an insane level of ego to be asking for that kind of thing. And so is there any way to do it that isn’t soul-crushing?
Reframe what asking for money means. Asking for money is a “first-aid” skill that everybody needs to learn. A lot more of us are gonna have to step up for ourselves and for people that we love. It doesn’t make it less bleak, but it makes you feel slightly less alone. “With funding cuts left and right, no universal health care, an affordability crisis, etc.”
When you ask for money, you are giving a gift. Most people think of asking for money as a favor. But think about it from the point of view of the person being asked. You’re actually giving them an invitation to get involved with a cool project. Plus, people feel good when they give money. It activates the reward system in people’s brains. It releases the feel-good, happy chemicals. Over the long term, it improves mental and physical health. It can lower blood pressure, reduce stress, boost self-esteem, and combat depression. I don’t know if I would use this in messaging, but it helps.
Asking for money is secretly the most popular thing ever. More people donate than go to church or vote or any other civic/community engagement. That scale is surprising. Lots of people donate. It’s less of an imposition to ask.

We underestimate the number of people who will say “yes” to us, and how much money they will give. Mainly because we’re embarrassed. To demonstrate, flip the script. Let’s say I write a weekly newsletter reviewing widgets. You love this newsletter. You live for my articles about how to build widgets at home. But it’s gonna go under if readers don’t give. But because I’m a fearless widgets newsletter writer, I’m gonna ask you for a bold and ambitious, but not undoable amount of money. How much seems reasonable? $75 a year or $10 a month. Why would this person say yes? Because they’re getting information they can’t get elsewhere. Or developed a relationship with the author. Or because they can afford it. Because they feel like things like the newsletter should exist. Maybe they get some kind of bauble or benefit. What are the reasons someone would say no? Either they can’t afford it or it doesn’t interest them enough. Or they’re supporting other things that take up their income. What does it feel like to be asked for money? If you look inside yourself, you might feel pretty willing to give. It’s easier to get someone to donate to stuff than you think. People like supporting things that they care about.
What are you hoping to overcome? What do you want to be courageous about? What’s in your control? When you call someone, asking for money, 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? It’s condescending. The fear of being uppity becomes realized.

What’s your worst fear if you ask for money? People will not only not want to give money, they won’t want to consume your product anymore. How likely do you think this is going to happen? It’s not super likely, but in your head, you probably think if you ask more than once a month in any meaningful way, people are just going to be “Go away. You are so annoying.” Is minimizing annoying people the point of life? Let’s say six months from now, you have to close shop. You announce the unfortunate news that you were not able to raise the amount needed to sustain yourself. Do you think your consumers might be annoyed you didn’t ask for money? That you didn’t say you needed support? If you can remind people of these rare special moments that your product provides and things you’re doing for listeners that exist exclusively because of your product, 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.”
You probably have some kind of earnings report or budget or cost analysis to figure out how much you need and how often. It should break down the business model for making money and where you’ll be at in six months with growth, membership subscription, ad revenue, etc. and how far you have to go to be sustainable.

Watch the vibes. One of your hang-ups may be worrying about being egotistical. Feeling bad about asking when people don’t have as much money these days. That whole hang-up of “Do I deserve money?” That is faux modesty and it’s not helping. We have fears of embarrassment. We prepare for ourselves for rejection ahead of time and we try to shortcode it for people to reject us. It’s like asking people to go to a party. If I were to ask you “Hey, there’s this party happening this Friday, but it’s it’s probably not gonna be that fun. I don’t know how many people are gonna be there and you probably have more important things to do.” Would you want to come to my party? No. Being insecure and sad is not the right energy to bring to fundraising.
There’s a vocal minority of people who are annoyed but also I am proving materially that people are listening. It’s a “free rider” problem. It’s a free good. Let’s take an example consumer, Danny, to find out why he doesn’t give.
1. Danny doesn’t live under a rock. He’s noticed there have been a lot of changes in how things can and can’t be funded. But he’s been getting stuff for free all these years and he hasn’t been trained to put kickstarters/patreons in his monthly budget yet.
2. Sometimes it’s hard to tell who is “big” and who is “small” because they can sound really similar and they all seem the same on the internet. He doesn’t want to give his few extra bucks a month to those who are already massively successful and raking in the profits because they don’t need him. He wants to give to small producers where he feels like, if he didn’t give, they might go away. Be clear about your status/role in the grand scheme of things. Approach it from a marketing perspective of “We are the little guy that needs your support. We are different from these other big producers/companies. We are doing this project in a different way.”
3. Danny wants to know all about the recipe for the brownie (product). 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? If you do publish your earnings/budget in an e-mail to your audience, members might miss it. It might also be that the “vibes” of the e-mail are annoying or pathetic. Try to get away from all the numbers and being a bummer.








