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Personal Finance For Women

She Retired at 32. Then Came Guilt—and a Moral Crossroads.

December 10, 2025

Culture, Financial Independence, Money Psychology

Listen & follow The Money with Katie Show: Apple Podcasts | Spotify

About This Episode

Rebecca Herbst reached financial independence at age 32 during the tenuous early days of the pandemic, and volunteered shortly thereafter to be furloughed at work—and so began her (extremely) early retirement. 

But spending her days exactly as she wanted featured an unexpected side effect: guilt. What do you owe to others when you’ve gotten everything you wanted? Rebecca alchemized her sense of duty and founded Yield & Spread. In detail, we cover:

  • ✋ What the “FI-lanthropy” pledge entails
  • 🔄 How she squares the desire to retire early with the idea of “hoarding money”
  • 🌏 Where Rebecca gives for the highest impact
  • 📂 Who donor-advised funds might make sense for, and how they work
  • 📈 How to donate appreciated stock, and why it might be  preferable to giving cash

This episode was produced by Katie Gatti Tassin. Audio engineering by Nick Torres. Devin Emery is the President of Morning Brew.

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Mentioned in this Episode

Transcript

Katie: [00:00:00] My guest today is Rebecca Herbst, the founder of Yield and Spread, which might sound familiar to you if you heard it discussed on a recent episode. Rebecca reached financial independence by age 32 after a career in commercial real estate, and I’m excited to talk to her about the excitement, the freedom, the guilt, and the questions of purpose that come up in the pursuit of financial freedom in a very unfair world.

And ultimately where those questions led her. Rebecca exists at the nexus of two communities of optimizers, the financial independence community, and the effective giving community. So both groups whose mantras I would consider could be summed up as work smarter, not harder. Welcome back to The Money With Katie Show.

I’m Katie Yati in this felt like, I don’t know, just the most appropriate conversation that we could be having right now, midway through the [00:01:00] holiday season, and it’s really consistent with some of the bigger philosophical questions that I receive about the ethics of building wealth for yourself and what sort of responsibilities that introduces for your life.

There are a couple of orthodoxies that I think Rebecca May challenge for us in this conversation, particularly with respect to the question of local versus global giving. I’m candidly really, really interested to know her perspective on this. And I’ve structured this conversation in two parts. So we’re gonna spend the first half really getting into the philosophical side, the ethics, the morality of it all, and then we will get into the more tactical pieces of donations.

You know, where to give, how to give, when to give, et cetera, in the back half. So without further ado, please enjoy this conversation with Rebecca Herbst of Yield and Spread.

[00:02:00] Rebecca, welcome and thank you for joining me today. I wanna start with talking about you. So you reached Financial independence by age 32. Which is amazing. Congratulations. And it is my understanding that your desire to do so was driven by a sense of incompatibility with the nine to five construct, less than like a specific job or industry.

So can you tell me a little bit about that?

Rebecca Herbst: Sure. So I can tell you with like the utmost certainty, I never expected to leave my job at the age of 32. I spent my formative years like working my tail off in college and school all to be successful. And to me at that time it was having a great job, hopefully an interesting job in a high-paced field.

And then learning about FI or financial independence definitely changed [00:03:00] things for me. It helped me see that like my value wasn’t necessarily tied to a job, but it was my boyfriend at the time, he’s now my husband, and he introduced me to the idea of phi. And when he told me about this, I was like, oh, you’re truly crazy.

And not because of the fundamentals, how to invest or how to optimize or how to manage your finances, but generally I just thought that work was your value. So if I wasn’t a commercial real estate researcher, then what was I? And also, unlike most millennials, I worked for the same company for 10 years. So my identity was like very, very tied to doing what I did.

And I liked my job in practice. I liked the subject matter. I loved the built environment. I liked solving complex problems. I worked with a lot of super interesting people, but I was constantly under. A ton of pressure from clients with super high expectations, bosses [00:04:00] with even higher expectations. And I just also kind of found myself floating into a category of like cleaning up people’s messes as I climbed to the corporate ladder.

Katie: Interesting.

Rebecca Herbst: And so, yeah, I think a lot of people can relate to this who are on the career path of traditional success. They find a job they care about, they find a job that gives them meaning, but then over time, it’s not like the job, it’s the operations and logistics of that that tend to get in the way.

So it wasn’t like I hated it, I just was kind of like, is there more to this than, than what I’m doing?

Katie: Was there ever that feeling of like, is this it?

Rebecca Herbst: Yeah.

Katie: I think that was kind of my awakening moment was just that realization of like, oh, and now I just do this for 40 years.

Rebecca Herbst: Yeah, I mean, I was a collegiate athlete and even in my first job in the first three weeks when I was sitting down at a computer screen, my body was aching, like just [00:05:00] from sitting eight hours a day.

And I think instead of taking a hard look at that feeling, then I just shoved it down and buried it down and it was like, okay, I guess is guess this is just what I do now. I work at a computer

Katie: or I get up really early so I can exercise before I have to sit for eight hours a day. So you finally leave your paid work at age 32.

How old were you when you learned about financial independence and the fire movement bridge that gap for us between kind of finding out about it and then like finally pulling the plug and how that felt.

Rebecca Herbst: So in financial independence terms, I reached my. Enough, I’m doing air quotes my enough, very quickly.

You talk about this in your book and across the podcast, right? Once you have 25 times your annual expenses saved up and invested, you theoretically can walk away from earning active income. And for me, it was only about four to five years. The reason it happened [00:06:00] so fast was because I had a lot of the building blocks in place.

Like I had a very high savings rate already sort of naturally frugal. I had no crippling student debt and I had a very solid career right from the get go. I just didn’t realize that there was like this mathematical equation behind when you can walk away from working. And so looking back, I spent most of those four years catching up on like all the financial sides of things and I didn’t really spend enough time thinking about what.

Early retiree lifestyle could look like or what my day-to-day might look like, or honestly more importantly, like practicing any of those things. So when I finally left my job, I felt really candidly lost, and I felt quite disconnected from the people in my community around me who were still on that traditional path of working.

And it took [00:07:00] a ton of self-reflection to understand that I was in the middle of like a huge life transition. And I think I was just supposed to wake up and feel happy.

And feel proud. I really should have been ecstatic about the fact that I did this thing. But emotionally, I think it took a really long time to catch up.

Katie: This is something that I actually think all retirees or anybody who’s going through a big life transition probably is going to struggle with to some degree, unless they have followed the Jillian Johns retire often path their whole life, and so they, they are pros at being retired and finding purpose and things other than work.

But I wanna talk about. How retiring early brings with it that additional layer of complexity, particularly if you are at all aware of the reality and the world around you and the country around you, where fire is not just counter-cultural from a philosophical [00:08:00] standpoint, but an intense location of privilege.

You mentioned that you felt privileged before fire two, but because you were still suffering from these long days and these bad bosses and these these other things that your average worker is going to deal with, you didn’t feel totally disconnected from that average struggle, and I love that you ended up going to the Women’s Fire Facebook page to seek advice.

Essentially seek solace. So tell me a little bit about what brought you to that moment to be posting in that Facebook page. Tell me about the headspace that you were in when you shared that. And I think in a bigger sense, I wanna hear about that guilt.

Rebecca Herbst: Mm-hmm. So I’ll just lead with this statement from this really beautiful thought leader in this space, Carrie Ann Rockmore.

She told me personally, I think it’s gonna take you between two and three years to really begin to adapt to this early retiree lifestyle. And I would say that was probably [00:09:00] bang on. And so for what it’s worth, unless you’re like my husband who’s born with literally zero levels of anxiety, you may have some time to adapt.

And that’s okay. In terms of the timeframe in which I left my job, it was about a year into COVID.

And I was in living in Boston, which was a place that was pretty locked down at the time. And at this time across the us of course, across the world, lots of people were struggling. I mean, I had immediate friends and family who were being laid off from their jobs.

Meanwhile, I had asked to be an included and around of layoffs from my job as I was sort of ready to leave being on this path to financial independence. So that means I got to willingly leave. I got paid a pretty generous severance package. It was like my version of a golden parachute, I guess.

Katie: [00:10:00] Wow. Love that for you.

Rebecca Herbst: I know it. It was, you know, pretty great timing. And then it was also around this time that I was seriously looking into concepts of social activism, philanthropy, morality. And this was really triggered by my reading of this incredibly influential book by Peter Singer called The Life You Could Save. And he makes just a super simple argument, which is affluent people like you and me have a moral obligation to give back to help reduce suffering of the world’s most impoverished.

So we’re talking 700 million people in the world who live on less than $2 and 15 cents a day. And like when I say 700 million people, it’s really hard for our brain to understand stats this big, that’s 8.5% of the world’s population. So for me, it was [00:11:00] incredibly hard to reconcile the idea of me being able to leave my job financially independent at 32 while knowing so many people were suffering.

This idea that I was born into a circumstance that I can pursue something like financial independence. I mean, for so many people, it doesn’t matter how hard they try or how much they work on their finances or how badly they wanna make a better life for themselves, they don’t live within an economic environment or circumstances to allow them to achieve what I did.

Katie: We’ll be right back to this conversation with Rebecca after a quick break.

I think it gets existential so quickly, doesn’t it? That like, mm-hmm. My soul was born into this body in this country, and that has done more to determine the outcome of the life that I get to live than any other [00:12:00] single factor. And it was a complete accident of birth. That’s really. Heavy and really important.

And I can see, I, I think I’m starting to get a sense for like the sort of big picture questions that you were now ha you now had the space to ask yourself, ’cause you weren’t distracted every day with emailing your boss back or living up to the expectations of the, the commercial real estate sector. You, you were like, I mean, what’s the, what is my moral duty as a human on this planet?

You ended up doing something with this realization that we’re gonna talk about in great detail. It’s my understanding that by the time that you were thinking seriously about how to give and what to give you were at phi, you had reached a million dollar net worth. I’m curious if in retrospect you wish that you had begun donating sooner or do you think that there is something to be said for eclipsing a certain threshold for yourself or for your family before you focus on [00:13:00] giving?

I have always seen this question as something that. Depending on the day and the circumstances, I could argue in either direction. I think that I so often see it as a goalpost that keeps moving and, and people who have way more than they could ever need are so uncomfortable with parting with money that I think I come down on the side of like, it’s better to establish the habit.

Katie: As early as you can rather than waiting. But I also think that that is a function of the fact that I feel like I have money to give away now, and I think that it’s very easy to be generous when your needs are met. So I’m curious if you have any thoughts on that.

Rebecca Herbst: Yes, I have a lot of thoughts and I think that’s a really wonderful way to put it.

The, especially the concept of the goalpost moving. So personally, I had always donated here and there, but it was very reactive. So something popped up in the news that pulled on my heartstrings like a hurricane Katrina, which was truly awful. Or a [00:14:00] friend was doing a charity run and I wanted to support them, or someone on the street is coming up to me directly and asking me for money.

So, you know, I gave, but I never had a system for giving. And so that’s a big part of why I eventually launched this concept of the philanthropy pledge. I wanted something to help people give in a way that feels intentional and not impulsive. And also to what you’re asking financially sustainable instead of overwhelming.

Rebecca Herbst: And so the pledge itself as people to commit to donating regularly. To give a percent of their income or wealth at a level that’s financially doable for them. So when people ask me whether or not they should hit a certain threshold before giving, I think it helps to just like zoom out and rethink what financial security even means.

So back to this global concept, I think most people don’t realize that if you earn [00:15:00] more than $69,000 a year in the US after taxes, you are already in the top 1% of income earners globally. It means that you’re 99% richer than the rest of the world. So for most of us, and alluding to what you were saying, that might not make us feel rich, but my hope is that this quick stat should put your financial situation into.

Context. So when I think about the stages of financial security, I know a lot of different financial advisors talk about like, you know, they have different metrics or different scales to talk about how to put different practices into place based on financial planning or your level of security. But for me, this is how I would think through the question of like, what kind of giving feels right at what stage?

So first and foremost, if you are financially unstable, ak, like you’re in crippling debt, this just might not be your time to give, and that’s totally okay. I think the expectation [00:16:00] here is put your oxygen mask on first and do what you need to do to be in a better place. The next stage is hopefully that you’re.

Stable. So you know you can cover your life expenses. You have an emergency fund built up, you see a savings rate for yourself. At this stage, I would encourage someone to consider something like the trial pledge, which says something like, try donating 1% of your income for a year. So if you make 60 KA year, that’s $600.

That’s 50 bucks a month. I mean, you could try this for a year or six months and just see how it feels, see how it impacts you financially. Personally, I think this is very doable for most people. I think there are many people out there and also listen to this episode that would be able to do this totally.

After that, you have like momentum, so you can like handle a curve ball. Your cash flow is predictable. This could be a good time to try upping that to 2% or 3%. And lastly, is this like sufficient stage, [00:17:00] meaning like you have enough, you can see that there’s a path to financial independence. Even if you’re not there yet, I think people at this stage should be giving by design instead of giving when asked.

And ultimately, like I think if you’re well on the path to financial independence and you have something like six figures in your portfolio, you are in a position to ultimately live a very happy and fulfilling life.

Katie: One question that I’ve been dying to ask you, I got recently from a Diabolical Lies listener, and they wrote, “Katie is not shy about her desire to retire early.

I want to as well, but also feel conflicted about hoarding my money so I don’t feel like I need my corporate overlord or spend a portion of my monthly income giving back and therefore working a lot longer. Is there a way to do both? It feels difficult to square.” Is this a conflict that you feel currently or felt?

Rebecca Herbst: Yes. Short answer. [00:18:00]

Katie: Let’s go. Long answer now,

Rebecca Herbst: let’s go. Long answer. So to me, the reality is at some point you will get old and you will either no longer be able to work or you’ll no longer want to work. And by this time in your life, you need to have built a nest egg to live off of. It’s just the truth of the matter and the way things are here in the us.

So that means you have to accumulate a portfolio of wealth, one that generates passive income and one that you can draw down upon. So I would reframe this language a bit from, instead of saying, I need to hoard money. Instead, maybe ask what amount do I need to live out my old age peacefully and securely.

So I think potentially what your listener might be trying to ask is something more like, how much can I give away or should I give away while still pursuing a life that I wanna live that feels secure? And so. [00:19:00] As I was like brainstorming this question for myself, I ended up coming up with this tool called the Philanthropy Calculator, and it helped me think through the math on this, like, how much money should I give away today and how will that impact to my timeline to phi?

So in this example, let’s say you made a hundred thousand dollars a year after taxes, which was pretty close to what I was making around the time that I was exploring this. Let’s say you spend 70 KA year, that’s a 30% savings rate. That’s not crazy, by the way, for someone who’s on the path to early retirement, if you were to donate 1% of year, like take that trial pledge, which I was talking about earlier.

Katie: So this would be basically your save rate becomes 29% and your philanthropy pledge is the 1%.

Rebecca Herbst: Exactly. So it’s basically like increasing your spend by 1%. It increases your timeline to five by literally half a year. Truly in the scheme of things, this is nothing. Six extra months. Yeah. No one, and no one I know even hits [00:20:00] by.

There’s like, okay, I hit it today, leaving my job. There’s usually some sort of transition period, and even if you were to donate 3% of your income a year, that’s an additional two years of working. Most of us don’t just stop working flat. Most of us continue to earn some sort of money. I mean, over the course of 30 years of that donation rate, this person is probably gonna donate 90 K.

And that’s a lot of money. Like it doesn’t even include your nest egg that you’re building this like nearly $2 million nest egg that you’re building, that ultimately this listener can give away at some point in their lives too, whether it’s in their old age or upon their death. I mean, I know personally from doing financial simulations on my own plan that.

There’s a very, very, very small percent chance that I could withdraw down on all my money. There’s much higher odds that I end up with a portfolio value that’s way bigger than what I [00:21:00] have today. Yeah. Just ludicrous. Just ludicrous. Like I’m talking like decamillionaire, and I think there’s lots of opportunities for building the habit for giving now, and you can iterate on that too over time.

Like if you’re giving 3% and you’re like, I really don’t miss this money. It hasn’t affected my financial path. Go up higher. You don’t have to make the decision right now today. You can iterate on this over years and years, and that’s okay. What do

Katie: you think someone is going to feel at the end of that first year when they’re able to sit back and look at what they’ve been able to give away?

What did you feel?

Rebecca Herbst: It makes me incredibly proud to see the work that I’ve done. Knowing that the flip side of that argument is I do not miss that money at all. It’s not like if that money were sitting in my account, I feel really good about it. I feel much better about the outputs. I see. And an organization called Give Directly, [00:22:00] which I feel very close to.

They recently reached out to me and said, Hey, Rebecca, you’re a top 3% donor. Wow. I never in a million years would’ve thought that at the rate that I was giving them, I was a top 3% donor. And what I’m giving to this organization is having an incredible impact. So I feel pretty good about that, and I’m okay with feeling good about that, if that makes sense.

Yeah. Don’t, don’t feel

Katie: guilty for

Rebecca Herbst: feeling good about it.

Katie: I think that that pride is an important like feedback loop, you know?

Rebecca Herbst: Yeah. But sometimes I look at those numbers and I’m like, I could be doing more, and that’s okay too. I think it’s okay to feel these conflicting emotions of having done something, but to know that you could probably do more and to know that, to be honest, like we all could probably do more.

Katie: Yeah, let’s crank up the cognitive dissonance then, because I think that there is a very interesting, as I conceive of it, philosophical debate that that question was gesturing at which I’m gonna define loosely in two different paths. [00:23:00] So the first path is invest in whatever will get you the highest returns.

If that includes defense contractors and oil and gas companies, and like, great, who cares? Get the highest returns you can get, and then turn around and donate as much as possible to the most effective organizations that you can. The other path is essentially seek out socially or environmentally responsible funds, invest in them even if your returns will be lower.

And even if that means you do have less to give later, obviously we’re granting that this binary is in fact just these two choices. But I think what this gets at a little bit for me is that dilemma between, am I using the right hand to fix what the left has broken? Am I breaking things with my investments and then using the returns to try to fix them after the fact.

Where did you locate yourself on the spectrum? Is this a question that you think about ever?

Rebecca Herbst: So [00:24:00] first and foremost, I wanna say that I’m not an expert on this subject matter, so I’m gonna share based on my perspectives. Don’t me neither.

Katie: We have that in common,

Rebecca Herbst: right? Always consult an expert. Um, I’m gonna just share my perspectives from my own research.

I think the research on the impact of ESG funds is extremely limited. Hmm. I will say there’s a lot of greenwashing out there. So I spoke with an individual the other day. I have a coaching program for people who wanna give away money seriously, in a meaningful way. And this individual had chosen a climate friendly bank to invest with.

And so this provider had a number of proprietary ETFs as well. And the cost to bank with them was 0.25% of assets under management. And this was on top of the fund fees, many of which hovered around 0.5% to 0.75%. [00:25:00] And so like if you’re super far along the path to financial independence and you have say like $500K in the bank and you’re putting in another like $20K year over the course of 30 years, you would probably pay.

Nearly three quarters of a million dollars in fees to invest with this bank. So just like pausing there, three quarters of a million dollars. And on this bank’s website, I, I see that they clearly care about climate change. I see that they clearly care about making the world a better place, but I didn’t see anything about rigorous research or telling me what three quarters of a million dollars could actually do.

Whereas like alternatively, if I took that three quarters of a million dollars and plugged it into the life, you can saves Impact Calculator. That’s the book that I mentioned earlier. They’re also an organization that does charity research and they show you where your dollar can go the farthest and have the biggest impact.

I could take that three [00:26:00] quarters of a million dollars and that would cover over a thousand lifesaving fistula surgeries for women. It would help provide safe drinking water to half a million people for a whole year.

Katie: Wow.

Rebecca Herbst: To me like this is a real impact on people’s real lives. This is very, very compelling to me personally.

So I, I tend to float in that direction of if I’m going to give money away, then I do want it to go to something impactful. So I guess the answer is I’m not against ESG investing. I think ESG funds and ESG investing in general can be useful and an important tool for investors who care about social and environmental causes.

And I think to your point, like negative screening, like investing in funds is just screen out the really bad guys probably a no brainer and effect. A lot of these types of low cost ESG funds are actually outperforming the s and p 500. Hmm. I [00:27:00] just wouldn’t be doing it at a risk of moving towards a fund with an expense ratio as high as 0.75% or 1%.

I’d also softly say that investing in index funds and ETFs is generally a passive investment strategy. It’s not an active one, and I’m just not quite sure how much change in the world we can make through being passive about things. Hmm. Like an active investment strategy looks more like being part of an investment circle or engaging directly with companies or having an impact on shareholder resolution.

So if something like that compels you all for it, I just think that passive investing might not have the impact that most listeners to this episode think it might have. I mean, these shares have been traded umpteen times. Right. So it’s like pretty much a changing of hands at this point, depending on what you’re investing in.

So if a bad guy corporation comes out and like [00:28:00] wants to raise money through bonds and then you go out and directly buy those, that’s probably. Directly supporting a cause that you don’t wanna be supporting, whereas like investing in the total US stock market index fund, I don’t know if that’s dramatically helping or hurting the world.

It’s certainly not helping, but I don’t think you’re, you’re like a bad guy by doing that.

Katie: There is an element of locality here. I know that, like I said, I kind of provided you a false binary. I said you can do this or you can do this. Where are you on this spectrum? Obviously there are other schools of thought and approaches that people have for how to invest money, maybe locally or keeping finances hyper-local, both from a credit union standpoint, all the way from like who you’re banking with to investing locally in businesses or what have you.

But I, I think that there was something that you and Brad. [00:29:00] Talked about along with another guest on this episode, uh, Jack in Your Choose Fi interview that brought up this element of giving locally or thinking locally that actually felt quite nuanced and interesting to me in a way that I had never heard discussed before.

I think Jack specifically made the argument that giving locally is suboptimal because some charities are 100 times or 1000 times more effective than others. And so giving $10 to your local soup kitchen simply because it’s the one that is closest to you is likely a far less effective use of that $10 than an organization where that same money might be able to literally prevent somebody from starving to death.

So my cards on the table here. I struggle with this idea because of the nature of multinational corporation, global capitalism. I think we have come to really romanticize the local. There’s a tension here that I wanna explore because the more that I [00:30:00] thought about it and allowed it to really challenge the way that I have conceptualized of like, oh yeah, I wanna like give in my community, the more it occurred to me that a local focus might actually ensure that, yes, your community benefits, but if you already live in a relatively well off community or country, it’s gonna stay very insular, right?

It’s going, you’re gonna continue to benefit more your, your community or country might from this ethos. But if there are other communities or countries that are extremely low income to begin with, that money might go way farther there. And ethically, how do you think about these trade-offs? What is your perspective here?

Rebecca Herbst: So the data does show that our dollar can go a lot further elsewhere. If you think back to that person living on less than $2 a day, giving them a hundred dollars is truly life changing. That person living on $2 a day isn’t necessarily having all their needs needs met, they’re covering the very, very basics.

So if you’re covering their expenses for [00:31:00] two to three months, imagine the type of forward thinking that this person can do and invest for themselves and create a future for themselves. I’ll say that, you know, personally, that’s very compelling. I also believe that all human lives across the globe are equal.

Like just because I can’t see or touch that person doesn’t mean they’re less valuable to me. So this story in and of itself is compelling enough for me to give money globally. But with that said, I, we are all human. We wanna help the people around us that we see, feel, and touch, especially the ones we love.

So what I would say to listeners would be. While we know some charities are more effective than others, generosity is generosity as long as you say, aren’t doing harm, which some charities can actually do. But assuming that the charity that you’re donating to is having a positive impact [00:32:00] on your community or the world, I would sort of think about giving in three pots.

The first is one for your loved ones, one for charities that you feel emotionally connected to. And this could be local because you’re close to them, and one that solely depends on the impact of your donation. And so in this way, you can support your community. The things that you feel and are close to, and at least you’ll know that some of your money is definitely having a real impact.

It’s kind of like a charity diversification strategy and a hedging your wrist. So I just think this is a really healthy way to start thinking about the question that you’re asking, which I don’t believe has a definitive answer.

Katie: Yeah. I mean, to be frank with you, I don’t think any of the things that we’ve talked about so far have definitive answers, I think mm-hmm.

Anytime we get into this realm of morality and ethics and what do we owe each other in the world, I think that it’s always going to be what is your [00:33:00] personal code and what feels like that capital t truth to you. Your work especially has introduced me to more global thinking. I think I, I, I get so hyper-focused on life in the United States and who is left behind here, and I think that I, I just appreciated that, that dialogue on that interview, because it made me step back a little bit.

And kind of contextualize where the US is globally and also the impacts that our country has had on other countries, and how some of these people in these other countries are in this position because of our country. So yeah, that kind of widening my scope a little bit, which I appreciated. I wanna ask you about something that was very, this is maybe a little niche, a little specific, but I was reading your announcement about the 10% giving pledge, and there was a line in there that really stuck out to me.

You wrote, what if I come across as a do-gooder and turn people off? Will you tell me about that?

Rebecca Herbst: Yeah. So at [00:34:00] first, when people hear that someone’s giving a meaningful portion of their money away, I think that there tends to be one of two reactions. The first can tend to be like, wow, you’re such a good person.

And the other is just often discomfort from the individual, the whole good person thing. For me personally, it makes me uneasy because I don’t wanna be seen as saintly when I come on, you know, a podcast like this. If you ask any of my family members, I promise you they will say, I am no Mother Teresa.

Rebecca sucks. Just kidding. Yeah. They’ll not view me as saintly, trust me. And I guess I’m just out here trying to approach giving in a thoughtful way. And I do think praise can get a little in the way of that message because it, again, it makes it seem like I’m doing this to be virtuous rather than, it’s like a responsibility that I truly feel that I share with others.

Katie: Oh, [00:35:00] interesting.

Rebecca Herbst: So the whole good person thing makes me uncomfortable. And then that second reaction, I mean, it worries me even more. It’s like about alienating people. Coming across as a goodie two shoes. I don’t want someone to avoid me because they feel like I know better than them or I’m expecting something from them.

And I think the other point to note here is the financial independence community and just like the personal finance world in general is just growing big time. Like 10 years ago, if I told someone that I was into financial independence, they’d be like, what are you talking about? And now it’s super mainstream people.

Yeah, there’s freaks like us everywhere. There’s freaks like us everywhere and they know what financial independence is, at least in abstract. So I think the real question is like, what are we gonna do as a community with all this wealth once we built it? What does life look like 10 years from now in terms of the legacy of the personal finance world?

Oh, I just got chills. Yeah. And I mean, at some point your kids only need so much generational wealth, right? Like the rest [00:36:00] can be used to have an impact.

Katie: I love that. I love that. Well, okay, so then relatedly and maybe counterintuitively with the kind of gut instinct or hesitancy that you were feeling, you also note that you think donating should be public because donating anonymously can quote, limit our impact.

Why is that?

Rebecca Herbst: So sometimes when I have gone out and introduced the idea of the philanthropy pledge to people, a common answer I’ve received is I’m already donating. I have no reason to take a pledge. And so I think making a pledge for a lot of people can make people uncomfortable. I think especially if they’re under that thought process of donating is more virtuous when done anonymously.

But I believe that a public pledge can lead to greater impact because one, it’s a commitment, right? Helps you stick to your goals. The second is community. So joining a network of [00:37:00] people who are also giving money away provides a lot of support, accountability, and thought leadership. And I think it also really normalizes the concept of giving.

So if your five best friends are donating regularly to charity, the chances are you will probably have an increased inclination to donate to charity. Totally. So for me personally, joining a community of 10,000 people who have taken a public giving pledge via the organization, giving what we can, I mean, this was just a game changer for me being surrounded by this knowledge.

And I think lastly, that would connect to culture, right? So if we’re taking a pledge publicly, it’s shifting norms. There’s so many people in the FIworld that I know who give regularly, but just at first glance, you wouldn’t know. And that’s because a lot of people have based their platforms on wealth accumulation.

And I just wanna create a place where people come together. I wanna celebrate them, I wanna reward them, I [00:38:00] wanna share their stories. And I really just wanna bring a lot of this to the forefront for people.

Katie: That is how culture changes. And I think that that, that is a really critical element of this. We will get right back to it after a quick break.

Do you wanna switch gears now and talk tactical stuff? Get into all my tactical questions. Oh yeah, let’s get nitty gritty. Okay. So we are gonna start big picture and then we’ll kind of drill down further and further into specifics. So you have a 10% yield and spread pledge in which people can pledge to donate 10% of their income.

So with regards to choosing 10%, you note that you chose this number because it is both significant and achievable. I think there’s also maybe sort of a spiritual element to this, I think in [00:39:00] recognizing the need to take action to solve the world’s problems and that collective felt sense of responsibility and like wanting the magnitude of that pledge to match the magnitude of that commitment or that responsibility.

Is that how you see it?

Rebecca Herbst: So you’re right in that the 10% is like grounded in something. It is historically grounded, for example, like the religious idea of tithing 10%. So we know that like there’s many, many people across the US that do this regularly and are living happy lives. So there’s a basis for that.

And like you said, 10% is significant and achievable, but most people still don’t, don’t do it. And so. I think the statistic is like in high income countries, people on average give away 0.7% of their income to good causes. This is like, to the best of our knowledge, really, I think moving the needle from 0.7% to 10%, that means it’s [00:40:00] greater than 10 times the impact than our typical rate of giving.

And so I think this does meaningfully shift the way we approach big world problems like poverty alleviation. And you know, I think, again, that 10% stack could seem really jarring and shocking to people. So I’m not necessarily out here saying just start at 10%, but if it’s something to work towards, I think it’s very doable and achievable for many people here.

Katie: You have personally taken this 10% pledge, right?

Rebecca Herbst: Mm-hmm.

Katie: And most people calculate this based on their income. I assume you’re looking at your income and donating 10% of it. Are we talking pre-tax? We talking post-tax? Let’s get specific.

Rebecca Herbst: I would say post-tax. Okay. But first of all, the money that you’re paying in taxes isn’t your money.

It’s not yours to give away. It’s going somewhere already. Mm-hmm. And if you take the thought process, taxes are a social good. You are giving back to your community via the tax system. So there is that concept. Being [00:41:00] tax isn’t necessarily bad. And so I would generally lean to the boat of post-tax, although I do know some people are very ambitious.

They swing for the fences. They swing for the fences, and they’re going going

Katie: pre-tax. Mm-hmm. I mean, I, for the same reason, always advocate for a post-tax savings rate. So I’m like, well. That money that’s go, you’re gonna pay in taxes. You didn’t, you didn’t get to choose what you did with that. But how does this work when you are FI already and you are only pulling out income from investment accounts based on what you need to spend, is that 10% just representative of like the overall withdrawal amount, would you ever recommend that someone who maybe already is at FI would move from a percentage of income more toward that percentage of wealth approach?

And if so, how would that calculus shift?

Rebecca Herbst: So I’m leading with the concept of 10%. ’cause I just think it’s something easy to digest. It’s easy to market, it’s easy to communicate. But I [00:42:00] know that in the FIworld, we have a lot of people out here who don’t have traditional forms of income. I had one pleasure.

Put this as like, I have a lot of edge cases for which I donate. So for example, I donate all the proceeds from my book. If I pick up a job, I’ll donate the proceeds for that. So I understand that there. Yeah, like I love these different ways to explore and I wanna share those stories more. My recommendation would be, if you’re just starting out, don’t over complicate things.

So if you take the 10% pledge and just donate 10% of your adjustable gross income or a GI, so this would be like your income after any adjustments, but before any deductions. This income could be from a nine to five job, dividends, interest, your side hustle, whatever. Just run with that number.

If you make less money in any given year, you donate less.

If you make. More income in any given year, you donate more. So it’s supposed to be this sliding scale so that you can manage [00:43:00] to make these donations without feeling financially unstable. So if you go into a year of financial hardship, maybe this is the year in which you’re scaling back significantly.

Katie: Mm-hmm. I think the thing about the wealth pledge for somebody that has already reached fi, which to be fair is probably a very small portion of this audience, but it did occur to me, so I wanna ask how you think about this. If somebody is already FI and 4% of their portfolio does represent their expenses, obviously then doing like a 1% of wealth is going to really meaningfully skew that calculation.

So I guess that could be the argument for building this into the spending plan to begin with. So it is factored into the FI calculation from the jump, right? But if you are already FI and you are doing the 4% rule thing, thoughts on accommodating in that respect.

Rebecca Herbst: Right. If you have not hit fi yet and you’re donating 10% of your income from your high paying job, there’s a world in which you can just calculate for that on a [00:44:00] go for basis.

Let’s say you’re donating $10,000 a year, you can just assume. What’s my FI path look like if I continue to donate that at that rate? You could also scale back based on what you think your income levels will be based on, you know, what you’re selling from your portfolio dividends interests for those people where like income just doesn’t make sense.

I wholeheartedly agree. Thinking about a wealth pledge could be very impactful. You use the example of 1%, which is pretty large. You could do something as low as like 0.1% or 0.05%. For example, I know someone who’s committed to donating 0.5% of his wealth every year, and what he does is he does large contributions to DAF every so often to help him with tax deductions over time.

But then he keeps the steady pace of giving at that 0.5% from his, not of his DAF, of his total portfolio. Sure. But he keeps making those [00:45:00] grants monthly. Over time, you can calculate those numbers to see what it means to do, or to have a safe withdrawal rate of 4.1% versus 4%. If you wanted to do something like follow the Trinity, study safely, withdrawal 4% from your portfolio, but also donate 0.1%.

Katie: Did you ever read the FatFire subreddit?

Rebecca Herbst: I know of the subreddit. I don’t get that deep in there.

Katie: There was a post last night that was so timely and I was like, oh, I can’t wait to tell Rebecca about this. Someone had posted in there to be like, what is y’all’s giving strategy? Like, how do you design your charitable giving every year?

And the comments were extremely heartening. Like I usually, that subreddit can be a little like, you know, out of touch, but one of the people that commented was like, oh, we just do a, every dollar we spend, we give a dollar away. And I was like. Whoa, that is, I mean, these people are very wealthy, right? So that’s

Rebecca Herbst: very impressive.

Katie: But there were a lot of really creative [00:46:00] ways that people had structured what they were giving away and what their targets were. And I saved the post, I’ll put the sub Reddit thread in the show notes if anyone’s curious and wants to read through it. But that’s always a really fun one. So maybe someone has identified a target percentage that they would like to donate.

Now they have another question. What sort of cadence do I give on? Do I calculate this annually? Do I set a monthly target? What about quarterly? I’m curious what you recommend. I will say that I know for diabolical lies and our redistribution pledge, we calculate quarterly net revenue and then set aside our percentage of that to give away.

And quarterly is a nice cadence for us where it doesn’t feel like we’re waiting a really long time, but you’re not doing it like every couple of weeks.

Rebecca Herbst: I think donating is just like any other uphill habit. Slow and steady wins the race. So using a percentage based pledge, you would base it annually, so it’s like 10% of your income annually.

But I recommend the actual [00:47:00] donating happening on a monthly basis.

Some folks might like to even do this alongside each paycheck. So it’s like you’re seeing money in and seeing money out at the same time. I like to do it in accordance with like a positive habit I already have built into my life. So on the first of every month I sit down with my husband and we have our finance meeting.

We just slot making our donations into this time. I think if you wait until the end of the year to donate, say like Giving Tuesday, or you might do it around the holidays ’cause there’s all this like marketing push from different charities, like you know, with matching opportunities and things like that.

If you just write a big check around that time, I think it will. Feel harder. Yeah. To give away a larger sum of money. And also it’ll feel harder because you haven’t done it in 12 months. So I truly believe to keep the habit monthly is required at minimum for anyone starting out. [00:48:00] Obviously if you are like a well optimized, well-oiled finance machine, you might be able to get around this, but I think the average person really needs to like be a part of it and experience more regularly to commit to it.

Katie: Yeah. Like build the muscle. Yeah. That makes sense. I know loss aversion is very real. Like psychologically we know this is very powerful feeling that humans feel more pain at like losing something that they get already than never having had it. And I think that contending with that and just planning for that reality is very important in keeping something like this sustainable.

The other piece of it that I think is maybe a little bit more. Silly, but always seems to be true for me is December is always such an expensive month for me and I just don’t know if trying to plan to give away a lot of money at like a moment where you’re also probably spending a lot of money on other people is setting yourself up for success [00:49:00] either.

Rebecca Herbst: Yeah. I mean, to be honest, I didn’t even really think about that deeply. That could be because I don’t celebrate Christmas, but I think that’s such a good point that like people are spending a lot of money on Black, black Friday. People are spending a lot of money on gifts and that spreading that love throughout the year helps with that loss inversion.

I think that’s a really thoughtful point.

Katie: Oh, well, thank you. You’ve mentioned give directly. Yep. A couple times already. This is one of the most asked questions that I feel like. I get whenever we talk about giving, is feeling that obstacle of, I don’t know where the money is gonna go, Forst. I don’t, I haven’t done all the research.

I don’t wanna give to the wrong place. It seems like this is a challenge for you in your work, probably to communicate how to give effectively without overwhelming people to the point that they feel like it is too complicated and they just throw up their hands and move on. So what specific organizations do you give to and why?[00:50:00]

Rebecca Herbst: Right. So we talked about those three buckets earlier. Giving to loved ones, giving to things you feel emotionally connected to, and giving to something that we know is high impact. So for me, I actually feel very emotionally connected to the high impact charities I donate to. It’s not this like strong bifurcation where I’m doing.

Good, but not following my heart. I think for some reason people feel like if you send money far away, it won’t feel good or you can’t be connected to this idea. So I just wanna clarify that, that point. I also wanna say that the charities that I do donate to do an incredible job of updating me on the impact of my work, and that makes me feel really good about donating.

So you brought up GiveDirectly, which is a charity that I love and I’ve spoken about them before. And they’re an organization that sounds exactly like their name. They send cash donations to people who need it most, and [00:51:00] I find them exceptional because they believe that people deserve the dignity. To choose what is right for them.

They are prioritizing what the recipient needs over what we, the donors think that they need or what the organization thinks that they need. And they’re also not just helping random individuals. They’ll target communities all at once. So the idea being if you support an entire community all at once, it creates a broader, more lasting economic impact.

A rising tide lifts all boats. So they’ve done a great job of sharing personal stories of individuals who have received grants, but then they also have that like rigorous research around their impact. And they’re proving that direct cash transfers are transformational to lifting people up out of poverty.

They’re also honest when they make mistakes. They’re the first ones to admit that they’re not a solution or a replacement for a well-structured [00:52:00] government. But that funding to these causes. Really can make a difference. So I would say that Give directly is this high impact organization, but one that is my heart is drawn to as well.

You can rely on some of these charity research organizations. The Life You Can Save is one. Give Well is One Giving Green is one. There are a few out there that have done the work for you and have a list of charities that they recommend. So if you wanna start there, I mean, that’s a wonderful place.

And then of course you, if you have the time or if you have the desire, you can dive deeper and explore these things further on your own.

Katie: Mm-hmm. Well then a related question is, are you donating cash or are you donating something else?

Rebecca Herbst: So I personally donate appreciated stock. I live mostly off of my investments, so it just makes sense for me to donate stock from my portfolio.

And I’m choosing [00:53:00] specifically to donate shares that have the largest gains because when you donate stock directly to a charity, you can avoid that 15% capital gains tax if I were to sell otherwise. I should note though, that in 2026, there’s a major change coming. There’s an above the line tax deduction being introduced.

It’s a thousand bucks for single filers, 2000 bucks for married filing jointly. This will apply to donations, to qualified charities in cash only. Mm-hmm. So I may lean into this a bit more in the coming years, but for now I’m, I’m pretty focused on donating appreciated stock.

Katie: Okay. So just to clarify then.

They’re changing the tax code next year so that even if you are taking the standard deduction, typically you would have to itemize charitable deductions in order for them to be deductible. But you can take the standard and single folks can get a $1,000 deduction for a thousand dollars of giving in cash to a qualified [00:54:00] organization.

Married couples can get up to 2000, but more broadly, your strategy is you donate appreciated stock rather than selling it, realizing the gain, paying the capital gains taxes, and then donating the cash, and then I assume you are then using or selling and then living off of the shares that have smaller.

Gains so that you’re not triggering as much of a tax bill. Bingo. Cool. So in order to do this, the tactical steps of doing this, you’re going into your brokerage account, you’re looking at the transaction history of when you bought a share, and then you are essentially prescribing that specific share that is tied to that specific transaction to the

Rebecca Herbst: charity via the donation form.

Exactly. So I go into my regular brokerage account. I open up a tab called Tax Lot Details. I can sort my shares by the cost basis or like what I bought it [00:55:00] for.

And then I choose the ones that have the largest gains, or in other words, have appreciated the most. I have to fill out this form called a partial asset gifting form, which asks me some basic information, like what account am I gonna donate from?

It asks me this specific asset and like the tax lot that I’m gonna donate from. So I’d write down the cost basis for that, share the date I bought it. And then of course, I’m also including all the charities information, including banking info, which is usually publicly available on a charity’s website.

So I would say this is actually a painful part of donating appreciated stock from your regular brokerage account. It’s typically not automated as it is, as it would be from a donor-advised fund. Unfortunately, I don’t think banks are particularly incentivized to make this process easier for us. But imagine a world in which, if you’re doing this regularly, you see a buy and sell button, but you also see a donate button.

Yeah. That’s a world I would love to envision.

Katie: Oh, [00:56:00] that’s good to know. And the, the form that you mentioned.

Rebecca Herbst: It’s coming from the bank. Right. Some charities will handle this for you, but most of the time you’re, you’re on your own.

Katie: You’re going through the financial institution.

Rebecca Herbst: Yeah. And there’ll be some sort of e-form, hopefully it’s not a PDF that you have to fill out and fax in or email in.

And if you’re donating to, you know, one charity or one or two charities, it’s not that big of a deal. It’s pretty fast. It takes me about 15 seconds. I’ve saved a previous filled out form so I know exactly what I need to fill in. Smart. But it is manual. If you did wanna donate appreciated stock to say 20 different charities a month, that could be a lot of work because you have to fill out 20 different forms, do it every single month, and then also pick all the shares that you wanna donate.

So in that world, it could make more sense too. Use a donor-advised fund. And we could talk about that a little later too, if you’d like.

Katie: Yeah, [00:57:00] I would love to talk about donor-advised funds. I, this is something that I hear about a lot. I don’t have one, so I’ve never done, like, done this process myself. You told Brad I know on Choose Fi, that they involve some fees, but they can be kind of the equivalent of that.

Set it and forget it. Approach that so many in the FI community. Love. Why is that? Why would a, a DAF be a set it and forget it approach.

Rebecca Herbst: So if you work with a financial planner and you wanna give regularly, chances are they’ve probably recommended a donor-advised fund because it’s become this like workaround to the operational pains and logistics of donating to many charities at once.

DAFs are one of those things that are marketed to us as like the holy grail of charitable giving. But I do think that they could be misleading. So for example, people think I need a DAF to get a tax deduction, and that makes sense because that’s li like if you, I got an ad for Fidelity Charitable today, and that’s the tagline was like your tax smart [00:58:00] investment.

Right? So it makes sense that people think this, but the truth is, and you talked about this earlier, no, you get deductions whether you donate cash or appreciated assets directly, as long as you are itemizing your deductions. So you’re not choosing to take the standard deduction and you’re itemizing at a level that’s high enough.

That it’s worth taking that approach. Now 90% of Americans take the standard deduction, so most people are truly not donating at this level. Like if you’re making a hundred thousand dollars and you take a 10% pledge, it actually still may not make sense for you to consider itemizing your donations ’cause it’s still not enough money to warrant greater tax deductions.

Mm-hmm. So you need a DAF for tax deductions is not really true. The second thing that gets marketed to us about DAFs is that they’re the only way to avoid capital gains tax. So this is also kind of wrong. We know that [00:59:00] donating from a regular brokerage account, as long as we donate those assets directly to the charity and we don’t liquidate those first, it does the same thing.

DAFs do, however, allow you to avoid taxes on like the dividends and interest paid by those investments. So that, that should be said. That’s a good thing. Oh, that is a good thing. Yeah. I hadn’t thought about that element of it. Okay. So I do think DAFs are like a little over marketed to us as these like amazing tax vehicles.

So what I think a DAF is good for is one, you can front load charitable contributions in a high-income year. So let’s say you were that. A person making a hundred thousand dollars and all of a sudden you came into $200,000 that year and you were gonna still donate 10%, it could make sense to just front load that.

But then you don’t have to make your donation decisions immediately. You can spread them out over time. So when you make your contributions to a daf, you can then still say, I wanna grant out X dollars every month over time. So that keeps it consistent for the charities. They [01:00:00] also make it automated for you, right?

So you can list all the charities up front, you can list those 20 charities you wanna give to, and that it just automates it out every single month.

Katie: Oh, nice. So would you say that somebody who’s maybe really trying to donate to a lot of different places this would, that would maybe tip them over into DAF territory?

Rebecca Herbst: Totally. As long as those places that this person wants to donate are qualified public charities and can accept money from a DAF, so most charities should be able to accept money, but not, some small ones are maybe not set up for it. Mm-hmm. Or maybe you’re trying to donate to a cause that isn’t a qualified 501(c)(3).

Just make note, you can’t use a DAF for that.

Katie: Got it. Okay. So to kind of clarify a little bit more around the standard deduction things, I think sometimes that can be a little bit confusing.

Rebecca Herbst: Mm-hmm. Yeah.

Katie: In tax year 2026, I believe for married couples, it’s going up to 32,000 something, 33,000 something.

It’s in that [01:01:00] ballpark. Yeah. And so when Rebecca says that like you might be donating $10,000 and yet it still doesn’t make sense for you to itemize, that’s because this deduction is so high already. The standard is so high already that you really aren’t getting any incremental gain from itemizing until you are.

Over and above that 30,000 ish point. However, another big change to the tax code going into next year is the expansion of that state and local taxes deduction. So your assault deduction is going from like 10,000 up to I think 40,000. So if you, for example, just bought a home and you have a 6% mortgage and like you are paying a lot in mortgage interest right now, you might get into a position where if you are taking a 10% pledge and you’re paying a lot of mortgage interest, that those two numbers together become competitive with that standard deductions.

I’ll put a calculator in the show notes that can help you. [01:02:00] Decide what makes sense for you,

Rebecca Herbst: right? This is always a tricky one. So a couple things to add onto that there. One, if you really think you’re floating into a territory, it makes sense to itemize. Like it could be very worth consulting a tax advisor at least on a one-time basis to get it all straight, right?

So I’m just putting that out there. So the other thing I’d say is like, right, there’s a lot of different things that you can itemize. You mentioned it. Mortgage interest, high property taxes, substantial medical costs. The new thing that’s being added in 2026 as well, just to make things more complicated.

This, this always, Katie, I, I actually don’t know what you’re gonna say. Charitable deductions for people that itemize face a 0.5% AGI floor. Mm. So meaning the first 0.5% of your income given to charity isn’t deductible at all for people who itemize. So while there are some things that you’re talking about that might incentivize people to itemize and donate more, there’s also these other things at play.

So I would say [01:03:00] unless you’re giving substantial sums of money or have other large deductions, I think the typical narrative will remain that it’s potentially likely that your charitable contributions will not be tax deductible. I think this begs the question of should I bunch or bundle my donations to achieve meaningful tax deductions, taking multiple years of donations at once, putting it into one year.

So that you can exceed the standard deduction. It’s often framed as this like hack. So instead of three years of donating $10,000, you decide to donate $30,000 in one year. So this is like a perfect option and many people do this and I think it is a good idea from a tax perspective, but I think this bundling concept has a down downside and that it disrupts your giving habit,

Katie: right?

It undermines the other thing we talked about, which is that the monthly cadence is [01:04:00] preferable

Rebecca Herbst: and not just preferable for, I think you the individual, but also for the charity, right? To be able to predict the type of cash flow that they have.

Katie: I wanna run something by you then. Let’s live game this out.

So let’s say I’m, I’m taking a pledge, right? I’m gonna do 10% of income. I still have income. So I’m like, that’s how I’m gonna decide the number, the target for the year, but I’m going to use appreciated stock to hit that number. So it’s not technically the new income that is coming in that is being used, I’m maybe replenishing the 10% that I’m donating with that new income, but then donating the appreciated stock.

Same net impact here.

Rebecca Herbst: Yeah. And because the value of my assets fluctuates, sometimes I’m probably giving 9% and sometimes I’m giving 11%. And that’s okay. I would just sort of approximate the best you can. And if it’s easier for you to just say like, look, I’m gonna [01:05:00] donate three shares of VTI every month or whatever.

Just do that. I think the point is not getting this perfect. The point is that your moral compass is pointed in the right direction and that you have a system and you have a regular habit that you can build.

Katie: No, I am going to get it perfect. Perfection is very important to me. No, that’s really helpful.

That’s kind of fun to think through in real time of like, okay, how would I strategically design this? The reality is that I’m actually quite lazy, and so I probably would end up just donating cash because it’s easier, but do as I say, not as I do.

Rebecca Herbst: Yeah, and maybe at minimum you could say, well, at least a thousand dollars will be in cash if I take the standard deduction, because then I will most certainly get one.

Katie: Well, thank you so much for joining me today. This was really fun. I appreciate you coming on to talk about this.

Rebecca Herbst: I’m so glad you had me. Thank you.

Katie: That [01:06:00] is all for this week, and we’ll see you next week. Our show is a production of Morning Brew, and this episode was produced by me, Katie Gatti Tassin, with audio engineering and sound design from Nick Torres. Devin Emery is president of Morning Brew.