21 in 21: Rainey Reitman on Transaction Denied and Financial Censorship

Rainy, welcome to the 21 and 21 show. Thank you so much for having me. Yes, thank you for stopping by Presidio Bitcoin. You've been here like once before, but it's lovely to have you back.

It's a beautiful space. It's like such a delight to come here every time. Oh, good, good. I'm glad you like it.

Well, I'm excited to talk to you today. I have a bunch of questions for you and your new book that's about to come out so soon. Yes. But before we start diving into kind of more of the book and what you're working on, you're like a different kind of person that we're having on the show where you're not like working in the Bitcoin space, which is amazing.

We want more of that. So can you just tell our listeners just a little bit more about you and kind of like your background? Sure. So I'm a civil liberties advocate.

I've worked on privacy and free expression. I've done a lot of work on whistleblower issues and I helped co-found and a nonprofit project and I worked on it for six years around supporting and advocating for whistleblower Chelsea Manning. I was with the Electronic Frontier Foundation. I am not a lawyer, even though EFF is known for being a law-based organization.

I ran advocacy for them for years and then did more management stuff. And then I also co-founded Freedom of the Press Foundation, which supports journalists and does some pretty amazing advocacy around the First Amendment here in the United States. Amazing. I am just so curious how you got into like all this advocacy work.

Yeah. How do you get into all of this? That's a good question. So I was working at a consumer privacy organization in San Diego.

I knew I wanted to work in some kind of nonprofit organization. And I kind of fell into that. And it was about data privacy. It's called the Privacy Rights Clearinghouse.

It's a three-person nonprofit. And I just fell in love with kind of data topics and the whole issue space. And then, yeah. And then after Chelsea Manning's first release of the collateral murder video to WikiLeaks, I was just so moved by it that I wanted to do something.

And I decided, you know, as soon as her name was known, that I would be involved in her campaign. And it turns out, and I found this so shocking, that if you're somebody who cares, you can actually just jump in and get involved and start, you know, becoming a leader of an organization or work towards something. And people are happy to have you if you're willing to put in the time. And in some ways, I think that is very synergistic with some of the things I see in like the free software community.

Right. The same idea of like anybody can get involved while they're in advocacy to in some projects. It's the same thing. So that was my first foray into into kind of large scale advocacy.

see. Yeah. So I'll kind of getting into your book a little bit, Transactions Denied, which comes out April 7th. April 7th.

So we're like a little more than a week out. Congratulations. Thank you. Book publishing is a lot.

It's a slow process, but I've learned a ton. Yeah. I saw that you, so your work was like, your book was like accumulation of like 10 years of research. Yeah, I started collecting the stories.

So the book is a few different things. It's called Transaction Denied. And it is about, it kind of goes back and forth between the stories of people who had their financial accounts frozen or canceled or were denied access to the financial services for some reason, and then a discussion of the laws and policies around it. And then I kind of looked for themes within different types of people losing their accounts.

So I was mostly looking at people who were engaged in some kind of speech that would have been legal under the First Amendment and protected here in the United States. And I mostly looked at people in the U.S. and I mostly looked at U.

S. companies cutting off access to their accounts. I did that on purpose. A lot of people think, oh, in the U.

S. this isn't a problem or, oh, this is something you'd see in like authoritarian regimes overseas. And I wanted to be like, no, this is the thing happening here in the United States with U.S.

customers. They are losing access to their financial accounts based on their legal speech. So that's what my book really pushes around. So that's the book.

And it's been, yeah, it's been a huge journey writing it. I actually finished it in like 2024. And so now it's 2026 and it's finally coming out. So I'm very excited to see it in bookstores.

Yeah, I know a little bit about the book publishing process, and it's definitely like a lot of work to get pitched to publishers and kind of back and forth with editing and everything. So huge congrats. It's a lot of work, especially you were writing this book as you were working. A lot of it, right?

Part of it. So I was with the Electronic Frontier Foundation until 2022. And I did collect a lot of the stories that are in the book. you asked this question and I kind of like answered a different question.

So let me go back. Yes, this book is based on about 10 years of stories that I collected from people largely while I was working at EFF. And at the time I was collecting the stories, I thought it was going to be a white paper. I was kind of blogging about it sometimes, but I was hearing more and more of these stories.

And I was like, I'll turn this into some kind of white paper. And then became very clear to me, this is actually a book. Like there's a lot here that I need to talk about. So I left EFF in 2022, did a little travel, some hiking, and then I wrote this book kind of mostly in 2023 and then edited it in 2024 and then submitted it.

Yeah. Crazy. A lot of years of research that went into this book. I haven't finished the book yet.

I have read, I guess, about 30 pages. But your intro just like really really hooked me with the Chelsea Manning story and how you were kind of like personally affected by financial censorship with her campaign And yeah that was seems like a kind of big moment for you and kind of how you kind of went for parts of your career Yeah So the story there is you know I was working at EFF and I was working on the Chelsea Manning Support Network And this is during the time when WikiLeaks had its financial services blockaded by Visa, MasterCard and others.

And so you could not make donations to WikiLeaks directly, which you'll find out about this if you get further in the book, then inspired us to start Freedom of the Press Foundation, which allowed people to donate directly to WikiLeaks through us for a number of years. But way before any of that, back in 2010, Chelsea Manning Support Network, we had our PayPal account frozen. And I knew we hadn't done anything wrong. this organization that was our fiscal sponsor, they had had a PayPal account for five years, no problems.

All of a sudden, they have this campaign around a whistleblower and their PayPal account was frozen. And we ended up having to, I mean, I did a ton of outreach to PayPal. I had contacts there. I was certain I could get it resolved.

And it ended up being a publicity campaign that used public pressure that got them to open up our PayPal account again. But for me, I realized how vulnerable advocacy organizations could be to this type of pressure, right? That if you aren't able to get, you know, support from your donors, like that's your lifeblood. It's an existential threat to the future of your organization.

And so this was a way to basically cut the knees out from under advocacy organizations that I saw how devastating it could be. So once that happened, even though I was able to get it resolved or we were able to get it resolved, you know, thanks to a lot of public pressure for us and PayPal, I was like, I kind of want to see if there's other people this is happening to as well. And that was the spark that kind of got me to start collecting these stories that became the basis of this book.

Was it hard for you to like find other people that have been affected or how do you even go about that process? Yeah, well, I mean, the nice thing about working at EFF is that people just reached out to us. And so when people would contact EFF, you know, the thing I think is useful to know is that But most of the time, most of the time, if you are losing access to your financial services because of, you know, some legal speech you said online, certainly at that time, there's been an executive order since then that's maybe changed the situation a little bit.

But there isn't like a lot you can do about it, right? Other than raise awareness, which meant that a lot of these were ending up kind of coming over to me on my side of things rather than as an opportunity for the lawyers to engage with it. And so when people were reaching out, I was connecting with them and sometimes we could help them directly or sometimes we could blog about it. Sometimes we couldn't do anything, but I would kind of like keep it in the back of my mind about like what was going on.

So, um, that was the first way we found out about it. And then after that, I just kind of, um, kind of kept my eyes open and people would kind of like connect me with folks, but when they heard about it. So I did end up doing some independent research, but I mean, a lot of people came to me. wow yeah that must have been like kind of a little bit heavy but yeah um i guess maybe a little validating but like you're not just like alone and i mean not in a good way but yeah i mean i imagine that there are a ton of people out there whose stories are completely untold right like the the small percentage of the people who are suffering from this problem that i was able to find out about it it's like you know i like to think that the stories i shared would be compelling to a lot of different people.

But the truth is there's probably so many more examples out there that are just not being heard by anyone. Yeah, crazy. And like you mentioned too, like that there's like these patterns, like certain demographics of people that you found were more affected or? Yeah, so I kind of, you know, after collecting stories, I started grouping them into sort of different communities communities that I saw were coming up very frequently in my conversations or was getting a lot of examples around.

And I kind of have a chapter on each of these topics in my book. One was on activists, so like political activists in the U.S. losing access to financial services, journalists.

I did people of Muslim descent. And I did sort of adult websites. And then I had, so I had a chapter specific to cannabis because there were just so many examples of that. But I think cannabis could be an example of a startup industry that was challenging existing industries.

And that's kind of how I framed it in the book as like, well, I'm going to talk about cannabis, but I think a lot of the experiences we have and that we see in the cannabis community might apply to other startup industries as well. So those were the five that I kind of identified and profiled in my book. so interesting um i guess kind of like what do you think is one thing maybe the average person who's unaffected like they don't understand or they kind of misunderstand about yeah this type of censorship yeah well i think the thing that i was i kept hearing when talking to people about this was people didn't understand how consumer protections worked they thought that there must be some law that guarantees that financial company can't cut off your services just because they don't like something you say.

And I kept being like, nope, there's definitely no law about that right There that in the United States we businesses have a lot of choice about who they do business with for better or for worse And what we seen and I kind of explore some of this is definitely coming because of government pressure. That's a huge elephant in the room that we have to acknowledge. But we see financial companies who are often citing things like reputational risk, have a pattern of cutting off people who are engaged in speech that they just simply don't agree with.

And I think a lot of people just assume it can't happen in the United States. Yeah. I mean, I don't think the average person would assume that it could. And then especially like, you know, people that think that they're just fine and are not doing anything wrong.

Yeah, that's it's that's really heavy and crazy. And you mentioned before that your work here and the stories you heard and inspired you to start this Financial Freedom of the Press Foundation. or can you maybe tell us a little bit more about that? Yeah, so the Freedom of the Press Foundation is a nonprofit and I talk about starting it in the book.

Small group of us at EFF were really concerned about the financial blockade against WikiLeaks. And at the time, you know, I think a lot of people were very ready for what we thought was gonna be a big court battle that was gonna be about the First Amendment and about the rights of publishers and about whistleblowing and all these other things. And instead, the attack came through the financial system. They basically, you know, no trial, nothing had MasterCard, Visa and others shut off donation access to WikiLeaks.

And it was immediate and it was devastating for that website. so um you know we knew and i talk about in my book that it would have been uh it would have been dangerous for eff if we received donations directly for wikileaks and um so we set up a separate non-profit called freedom of the press foundation and the first thing we did was start a crowdfunding campaign for wikileaks but also for other fantastic journalistic organizations who were doing amazing work. And so people could come onto our website, donate to any of them.

And then we use some pretty fun tools to make sure that we weren't keeping records of which individual people donated to which individual organizations so that if the government ever came and asked us for a list of all the people who had donated to WikiLeaks, we would be able to be like, we don't have that list. We just have a list of our total donors. And we certainly would not be giving that to the government. Let me be clear.

It was kind of like a privacy layer. You're like a middleman kind of so people can maybe more safely give donations. Yes, exactly. And so that was kind of the impetus for starting Freedom of the Press Foundation.

And then today, you know, eventually the WikiLeaks blockade was resolved, but Freedom of the Press Foundation is still doing phenomenal work. I'm still president of the board of the organization and half of the proceeds of my book, Go to Freedom of the Press Foundation. And it's an organization that it's really tech savvy. They go into journalist organizations all across the country and teach them how to use encryption and how to use kind of thoughtful tools.

We also maintain free software called SecureDrop, which basically lets any organization be the next week and week. So any newsroom can receive, you know, whistleblower documents securely without endangering the people who are sending them documents. And then we do some pretty cool things like we have a US press freedom tracker. And that is basically a way that every attack on a journalist here in the United States is documented and kind of like written up and we have all the evidence of it and categorized for the last, I actually don't know how far it goes back, maybe seven years.

And so you can kind of go and look up every single example that we can find of a journalist, you know, whether they're getting like physically attacked or their computers are getting attacked or being seized by the government. We've got it documented on our website and then we put out regular reports about our findings. So that's just some of the work they're doing, But it's a very wonderful organization. I'm super glad to have been involved in getting it started.

That's amazing. That's awesome that you were able to get something like that started. I'm so curious, kind of like with your experience and all of this, has that changed your behavior with any like financial products or even technology products? Yeah.

So I think my book is really about large policy debates. It's about what role financial companies should play and not as much about what individuals can do. I know because people are always like, well, what can I do to protect myself? And I'm always like, I don't want to have that conversation.

I want to talk about what do we do about the financial industry that thinks it should be engaging in censorship. Like, that's the conversation I want to have. And like if we don't fix that, you know, severe mistake that, you know, financial companies ever thought it was appropriate for them to engage in censorship, like then it really doesn't matter if we could teach one or two people how to protect themselves. So that's, I guess, the short answer to that.

Makes sense. A lot of it's out of the individual's role, unfortunately. Yeah. So I haven't gotten to this chapter yet, but I know that there's a bit in your book about Bitcoin and other cryptocurrencies and how they can kind of be like this more censorship-free alternative.

I kind of want to... Do you have any teasers to that section? Yeah. So I do have a chapter on cash and then I have a chapter on cryptocurrency and I primarily talk about Bitcoin.

And I talk a little bit about, I try to provide, and this is always very tricky, like a very like simple explanation of how it works for hopefully anybody can understand. And then I talk a little bit about some of the underlying philosophies that I think could be informing Bitcoin. And then I talk about, I kind of asked this question, which has always been the question that's driven me around Bitcoin and cryptocurrencies, but specifically Bitcoin, when I first started writing about it back in 2011 which was is this a tool against censorship And and I kind of like you know I'm like, well, you know, you could think of some edge cases, but like my general response is like, yeah, the protocol is actually extremely censorship resistant.

We've seen that over many years. It has, it has been resistant to attempts to make it into a tool that could be as prone to censorship as like Visa. But then I caution that this is unfortunately not how most people are interacting with the technology, right? Which is that many people are turning to Coinbase or to some other custodial service to obtain or to trade or to hold their cryptocurrency for them.

And as soon as you do that, you're recreating the same power dynamic that you have in the traditional financial world. And so, you know, I think my conclusion for that chapter is we can't, you know, given the fact that many people are still using custodial services, you can't say, well, technology is going to fix this entire issue. You still have to talk about policy reform and what do we do to make sure that not just cryptocurrency companies, but all financial companies get out of the role of acting as censors for online speech.

Yeah, we definitely don't want to just like repeat. Yeah, I'm constantly concerned. I definitely hear you there. I'm just so curious.

Did you kind of get interested in Bitcoin or even start researching a little bit through your other kind of work with advocacy and freedom? Yeah, well, I got introduced to it back in 2010 through a colleague of mine. in the Chelsea Manning Support Network. Actually, to be completely honest, I was kind of frustrated with Bitcoin when I first heard about it because he was going to leave working on Chelsea Manning Support Network to go work on Bitcoin stuff.

And I was like, what is this? You know, we have a lot of work to do here. But he kind of introduced me to it and I was really intrigued about it. And I was first intrigued about it, you know, as a, well, at the time, this is a very long time ago, I don't know if you remember this, or if you were aware of it, but there were a lot of people engaged in a particular type of like cyber activism called anonymous, where they were basically de-dossing websites as a form of political protest, which could result in them facing pretty severe penalties under the Computer Fraud and Abuse Act.

So I wondered about Bitcoin as a helpful way to engage people on something proactive, not something that could get them in hot water with the CFAA. But then I quickly kind of shifted and started thinking about Bitcoin as a tool for censorship resistance in and of itself. And that was kind of when I first started writing about it for EFF. So that was my first foray into it.

And yeah, and then I've just kind of kept an eye on it and been kind of interested in those conversations where they intersect with speech and privacy issues and censorship issues. I don't, you know, I don't pay attention to things like what is the price or is it an investment tool? I'm only looked at it from a civil liberties perspective. Super interesting.

I love your story and how you got into it. And yeah, I think the the overlap with Bitcoin and the ethos and now it can really help with, you know, an activist and kind of be more of a censorship resistant kind of tool is super interesting. Yeah. Well, we got through a lot of questions now.

I guess just like as a quick ending thought, like if you could leave our listeners like one thing about your book or anything else, what would you want to say? Gosh. Well, as a new author, I do have to say that Every time you buy a book, it makes a huge difference for me, especially if you buy it before the book comes out, because those are just like a wonderful way to help me out and to help spread the word about this. And then I guess the larger thing I would leave with is that I see these fights, sort of these larger struggles around financial freedom as all kind of being connected to some of these free speech fights we're having online.

And I think that there are few organizations doing as much good in that space as Freedom of the Press Foundation. So if you are interested, it's a membership organization, and we would love your support. amazing i will offer this i'm going to order one of your books and pre-order and get it after so you'll bitcoin so people can come here and they can check it out and they can order their own um well where like what are the websites or i'll put it in the links but anything you want to just say out loud if people want to like find you or your book or the press yeah so um you can find me on all the social media as rainie reitman the book is called um transaction denied big finances power to punish speech.

I also own the website financialcensorship.org. And so you can go there and you can find out about how to get the book or even book me as a speaker if you're interested. And yeah, so that's kind of the shorthand of where to find it.

You can find it anywhere books are sold and there's an audiobook too. Amazing. I love audiobooks. I do too.

Is the audiobook version out yet? The audiobook version will be out on the 7th. On the 7th. Okay.

I'll pre-order now and then I'm going to listen to on the 7th. I'm a big audio fan. Okay. And if folks are in the Bay Area, we're having two launch events.

One is going to be in Berkeley on the 7th at Mrs. Dalloway's. You can go on my website and get all the information about that. The other one is going to be at City Lights on April 9th in downtown San Francisco.

I guess it's the marina. I don't think that's downtown. So you can come hang out and we can have like a awesome conversation about what role financial companies should play in censoring speech online. Amazing.

I'll check those out. Well, thanks so much for coming on the show. Congrats on the book. And yeah.

Thank you so much for having me. This was so much fun. Oh, good. Of course.

Thanks.