
A conversation with the founder of Yield & Spread, Rebecca Herbst.
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Hey, Fidelity. How can I remember to invest every month?
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With the Fidelity app, you can choose a schedule and set up recurring investments.
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In stocks and ETFs. Huh, that sounds easier than I thought.
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You got this?
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Yeah, I do.
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Now, where did I put my keys? You will find them where you left them.
Investing involves risk, including risk of loss. Fidelity Brokerage Services, llc Member nyse, SIPC.
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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. 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 going to do as a community with all this wealth once we build it?
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Foreign.
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 hard, harder. Welcome back to the Money with Katie show. I'm Katie Gadytosan. This felt like, I don't know, just the most appropriate conversation that we could be having right now, midway through the 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 going to 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.
Rebecca, welcome and thank you for joining me today. I want to 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 9 to 5 construct less than, like a specific job or industry. So can you tell me a little bit about that?
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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 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 fi. When he told me about this, I was like, oh, you're truly crazy. 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. 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 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 the corporate ladder.
B
Interesting.
A
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?
B
Was there ever that feeling of like, is this it? Yeah, 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.
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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 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 was like, okay, I guess this, guess this is just what I do now. I work at a computer or I.
B
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.
A
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 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 rate 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 quote unquote, 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 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.
B
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 or retire office and path their whole life. And so they, they are pros at being retired and finding purpose in things other than work. But I want to 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 countercultural from a philosophical standpoint, but an intense location of privilege. You mentioned that you felt privileged before fire, too, but because you were still suffering from these long days and these bad bosses and 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 and 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 want to hear about that guilt.
A
So I'll just lead with a statement from this really beautiful thought leader in this space, Carrie Ann Rockmore. She told me, personally, I think it's going to take you between two and three years to really begin to adapt to this early retiree lifestyle. And I would say that was probably 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 U.S. 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 included in a round 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.
B
Wow, love that for you.
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I know 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 $2.15 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 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, and 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.
B
We'll be right back to this conversation with Rebecca after a quick break.
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I think it gets existential so quickly, doesn't it? That like 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 single factor. And it was a complete accident of birth. That's really heavy and really important. And I can see, I think I'm Starting to get a sense for, like, the sort of big picture questions that you were now you now had the space to ask yourself because you weren't distracted every day with emailing your boss back or living up to the expectations of the commercial real estate sector. You were like, I mean, what is my moral duty as a human on this planet? You ended up doing something with this realization that we're going to 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 fi, 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 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 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 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.
A
Yes, I have a lot of thoughts, and I think that's a really wonderful way to put it, 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 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 Filant 3 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. And so the pledge itself asks people to commit to donating regularly and 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 more than $69,000 a year in the U.S. 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, AKA like you're in crippling debt, this just might not be your time to give. And that's totally okay. I think the expectation 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 60k a 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. So 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 listening to this episode that would be able to do this totally. After that, you have like momentum so you can like handle a curveball. 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? 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.
B
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?
A
Yes. Short answer.
B
Let's go long answer now.
A
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 will 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 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 want to live that feels secure? And so 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 FI. So in this example, let's say you made $100,000 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 70k a 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.
B
So this would be basically your save rate becomes 29% and your philanthropy pledges the 1%.
A
Exactly. So it's basically like increasing your spend by 1%. It increases your timeline to five by literally half a year. I mean, truly in the scheme of things, this is nothing.
B
Six extra months.
A
Yeah, no one, and no one I know even hits five. 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 going to donate 90k. 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 have today.
B
Yeah, just ludicrous.
A
Just ludicrous. Like, I'm talking, like, deca Millionaire. 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.
B
What do 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?
A
It makes me incredibly proud to see the work that I've done. And 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 that I see. And an organization called GiveDirectly, which I feel very close to, they recently reached out to me and said, hey, Rebecca, you're a top 3% donor.
B
Wow.
A
I never in a million years would have 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.
B
Don't feel guilty for feeling good about it. I think that that pride is an important, like, feedback loop, you know? Yeah.
A
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.
B
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 going to define loosely in two different paths. 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 think about ever?
A
So first and foremost, I want to say that I'm not an expert on this subject matter, so I'm going to share based on my perspectives.
B
Me neither. We have that in common.
A
Right. Always consult an expert. I'm going to 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 want to give away money seriously and 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%. 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 a year. Over the course of 30 years, you would probably pay nearly 3/4 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 save 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 quarters of a million dollars and that would cover over a thousand life saving fistula surgeries for women. Or it would help provide safe drinking water to half a million people for a whole year.
B
Wow.
A
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, just screen out the really bad guys, probably a no brainer. And in fact a lot of these types of low cost ESG funds are actually outperforming the S&P 500. I just wouldn't be doing it at a risk of moving towards a fund with an expense risk 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. 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 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 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 want to 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 big bad guy by doing that.
B
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 hyperlocal, 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 think that there was something that you and Brad talked about, along with another guest on this episode, 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 1,000 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 roman romanticize the local. There's a tension here that I want to explore because the more that I thought about it and allowed it to really challenge the way that I have conceptualized of like, oh yeah, I want to 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 going to stay very insular, right? It's going, you're going to continue to benefit more 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?
A
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 $100 is truly life changing. I mean, that person living on $2 a day isn't necessarily having all their means, needs met. They're covering the very, very basics. So if you're covering their expenses for 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. So 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, 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, we are all human. We want to 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 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 and 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 risk. 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.
B
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 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 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 get so, 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 want to 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?
A
Yeah. So at 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 want to 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.
B
Rebecca sucks. Just kidding.
A
Yeah, they will 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 responsiveness that I truly feel that I share with others.
B
Oh, interesting.
A
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 goody 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.
B
There's freaks like us everywhere.
A
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 going to do as a community with all this wealth once we build it? What does life look like 10 years from now in terms of the legacy of the personal finance world?
B
Oh, I just got chills.
A
Yeah. And I mean, at some point, your kids only need so much generational wealth. Right? Like, the rest can be used to have an impact.
B
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?
A
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 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.
B
Totally.
A
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 FI world 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 want to create a place where people come together. I want to celebrate them, I want to reward them, I want to share their stories, and I really just want to bring a lot of this to the forefront for people.
B
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.
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Do you want to switch gears now and talk tactical stuff? Get into all my tactical questions?
A
Oh yeah, let's get nitty gritty.
B
Okay, so we are going to 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 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?
A
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 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% stat 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.
B
You have personally taken this 10% pledge, right? 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.
A
I would say post tax.
B
Okay.
A
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. 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 taxed 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.
B
They'Re going pre tax. I mean, I for the same reason always advocate for a post tax savings rate. So I'm like, well, that money that's you're going to pay in taxes, 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?
A
So I'm leading with the concept of 10% because I just think it's something easy to digest, it's easy to market, it's easy to communicate. But I know that in the FI world, we have a lot of people out here who don't have traditional forms of income. I had one pledger 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 want to share those stories more. My recommendation would be, if you're just starting out, don't, don't overcomplicate things. So if you take the 10% pledge and just donate 10% of your adjustable gross income or AGI, so this would be like your income after any adjustments, but before any deductions. This income could be from a 9 to 5 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 to make these donations without feeling financially unstable. So if you go into a year of financial hardship, maybe this is a year in which you're scaling back significantly.
B
I think the thing about the wealth pledge for somebody that has already reached 5, 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.
A
Right.
B
But if you are already FI and you are doing the 4% rule thing, thoughts on accommodating in that respect? Right.
A
If you have not hit FIYA 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 go forward basis. Let's say you're donating $10,000 a year. You can just assume, okay, 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, on, you know, what you're selling from your portfolio, Dividends, interest. 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 a 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, but he keeps making those 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 withdraw 4% from your portfolio but also donate 0.1%.
B
Do you ever read the Fat Fire subreddit?
A
I know of the subreddit. I don't get that deep in there.
B
There was a post last night that was so timely and I was like, I can't wait to tell Rebecca about this. Someone had posted in there to be like, what is Yalls 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?
A
So that's very impressive.
B
But there were a lot of really creative ways that people had structured what they were giving away and what their targets were. And I saved the post. I'll put the subreddit 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 in 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.
A
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 donating happening on a monthly basis. Okay. 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 1st 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 to give away a larger sum of money. And also it will 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. Obviously if you're 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 an experience more regularly to commit to it.
B
Yeah, like build the muscle. Yeah, that makes sense. I know loss aversion is very real. Like psychologically, we know this is a 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 either.
A
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 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.
B
Oh, well, thank you. You've mentioned give directly. Yeah, 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 going to go for this. I don't, I haven't done all the research. I don't want to 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?
A
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 I find them exceptional because they believe that people deserve the dignity to choose what is right for them. So 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 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 want to 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.
B
Well, then a related question is, are you donating cash or are you donating something else?
A
So I personally donate appreciated stock. I live mostly off of my investments, so it just makes sense for me to donate stock for my portfolio. And I'm choosing 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 1000 bucks for single filers, 2000 bucks for married filing jointly. This will apply to donations to qualified charities in cash only. So I may lean into this a bit more in the coming years, but for now, I'm pretty focused on donating appreciated stock.
B
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 $1,000 of giving in cash to a qualified organization. Married couples can get up to 2,000. 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, have smaller gains so that you're not triggering as much of a tax bill.
A
Bingo.
B
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 charity via the donation form.
A
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 for, and then I choose the ones that have the largest gains, or in other words, have appreciated the most. Then I have to fill out this form called a partial asset gifting form which asks me some basic information, like what account am I going to donate from? It asks me this specific asset and like the tax lot that I'm going to 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.
B
That's good to know. And the, the form that you mentioned.
A
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.
B
You're going through the financial institution.
A
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.
B
Smart.
A
But it is manual. If you did want to 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 want to donate. So in that world, it could make more sense to use a donor advised fund. And we could talk about that a little later too if you'd like.
B
Yeah, 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 and 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 DAF be a set it and forget it approach?
A
So if you work with a financial planner and you want to 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 daft to get a tax deduction. And that makes sense because it's like if you. I got an ad for Fidelity Charitable today and that's the tagline was like you're tax smart investor. So it makes sense that people think this. But the truth is, and you talked about this earlier, no, you get to 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 $100,000 and you take a 10% pledge, it actually still may not make sense for you to consider itemizing your donations because it's still not enough money to warrant greater tax deductions. 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 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.
B
Oh, that is a good thing.
A
Yeah.
B
I hadn't thought about that element of it.
A
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 person making $100,000 and all of a sudden you came into $200,000 that year and you were going to 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 want to grant out X dollars every month over time. So that keeps it consistent for the charities. They also make it automated for you. Right. So you can list all the charities up front, you can list those 20 charities you want to give to and then it just automates it out every single month.
B
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 daft territory?
A
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. Or maybe you're trying to donate to a cause that isn't a qualified 501C3. Just make note you can't use a DAF for that.
B
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. Mm.
A
Yeah.
B
In tax year 2026, I believe for married couples, it's going up to 32,000 something, 33,000 something. It's in that ballpark.
A
Yeah.
B
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 SALT 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 decide what makes sense for you.
A
Right. This is always a tricky one. So a couple of 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 like get your agree 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. As always, Katie, I actually don't know.
B
What you're going to say.
A
Charitable deductions for people that itemizes face a 0.5% AGI floor, 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 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 downside in that it disrupts your giving habit.
B
Right. It undermines the other thing we talked about, which is that the monthly cadence.
A
Is preferable, and not just preferable for, I think, you, the individual, but also for the charity.
B
Right.
A
To be able to predict the type of cash flow that they have.
B
I want to 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 going to do 10% of income. I still have income. So I'm like, that's how I'm going to 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 may be replenishing the 10% that I'm donating with that new income, but then donating the appreciated stock. Same net impact here.
A
Yeah. And because the value of my assets fluctuate, sometimes I'm probably giving 9%, and sometimes I'm giving 11%. And that's okay. 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 going to donate 3 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.
B
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.
A
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.
B
Well, thank you so much for joining me today. This was really fun. I appreciate you coming on to talk about this.
A
I'm so glad you had me. Thank you.
B
That 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 Gattytasian, with audio engineering and sound design from Nick Torres. Devin Emery is president of Morning Brewing.
A
And Doug, here we have the Limu Emu in its natural habitat, helping people customize their car insurance and save hundreds with Liberty Mutual. Fascinating. It's accompanied by his natural ally, Doug.
B
Limu is that guy with the binoculars watching us.
A
Cut the camera. They see us. Only pay for what you need. Need@libertymutual.com Liberty. Liberty. Liberty. Liberty Savings Ferry. Underwritten by Liberty Mutual Insurance Company Affiliates.
B
Excludes Massachusetts.
Episode: She Retired at 32. Then Came Guilt—and a Moral Crossroads.
Date: December 10, 2025
Host: Katie Gatti Tostain
Guest: Rebecca Herbst (Founder, Yield & Spread)
This episode explores the journey of Rebecca Herbst, who achieved financial independence (FI) and retired at age 32. Katie and Rebecca dive deep into the emotional, ethical, and practical complexities of retiring early in a world full of inequality. They discuss the responsibilities that come with wealth, the “giving back” debate (local vs. global, tactical vs. emotional), and how to integrate philanthropy into the personal finance journey. The conversation moves from philosophical questions about purpose and privilege toward actionable advice on charitable giving.
[03:33–08:22]
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[16:25–20:12]
[20:12–24:15]
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[54:13–57:33]
[57:33–61:21]
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[61:49–65:31]
[66:50–68:59]
Rebecca, on the paradox of privilege:
“For so many people, it doesn't matter how hard they try 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.” (12:01)
Rebecca, on emotional adaptation:
“I was just supposed to wake up and feel happy and feel proud... but emotionally, I think it took a really long time to catch up.” (06:36–08:22)
Katie, on accident of birth:
“That has done more to determine the outcome of the life that I get to live than any other single factor.” (14:33)
Rebecca, on ‘do-gooder’ syndrome:
“The whole good person thing makes me uncomfortable... I don’t want to be seen as saintly when I come on, you know, a podcast like this.” (36:45)
Rebecca, on building a culture of giving:
“If your five best friends are donating regularly to charity, the chances are you will probably have an increased inclination to donate...” (40:04)
This detailed roadmap should equip listeners—or non-listeners—with the philosophical frameworks and practical playbooks needed to integrate impactful giving into any financial journey.