Giant Robots Smashing Into Other Giant Robots

437: Hello Prenup with Sarabeth Jaffe

August 25th, 2022

Sarabeth Jaffe is CTO and Co-Founder at HelloPrenup, the digital prenup platform designed to get couples on the same page.

Chad talks with Sarabeth about dogfooding her own product, completely starting over from a technical perspective using Bubble, a low-code/no-code platform, and appearing on the ABC hit series Shark Tank.

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CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel. And with me today is Sarabeth Jaffe, CTO, and Co-Founder at HelloPrenup, the digital prenup platform designed to get couples on the same page. Sarabeth, thank you so much for joining me.

SARABETH: Thank you so much for having me.

CHAD: I can't say that I was aware of your...or that I wanted to think about prenups and seeking out a product around prenups. But it's super interesting to me. And I'm sure that that's part of both the challenge and opportunity with HelloPrenup. So, tell us a little bit about the product.

SARABETH: So, as you mentioned, HelloPrenup is really the first of its kind. It's a digital platform that allows couples to create a prenuptial agreement that they're both happy with completely online and for a fraction of the cost of going to an attorney. So why is that interesting for folks these days? Really it's because couples are talking about their finances a lot more before they go into marriage. People are getting married later in life, so they have more assets to protect, or in many couples' cases, they have a lot of existing student loans or other liabilities that they can actually protect their partner from.

So I think a lot of couples are becoming more open to prenuptial agreements as a way to kind of start off their marriage with a clean slate. And I can actually speak to our customers because I actually built HelloPrenup after I got engaged. And I was looking into getting a prenup. My fiancé and I we've been together for over seven years; we've known each other for over ten years. And we've always been really transparent about everything and especially our finances.

And I love being financially savvy, looking at my investment portfolio, and being really frugal and everything. So to me, getting a prenup was always just the smart move. Being kind of a realistic person whose parents are actually divorced now, I view marriage as a partnership that, if it's working, when it's working, that's amazing. But if things don't work out, I think there should be a different path that you're able to take seamlessly.

So when we did get engaged, I started looking into how to get a prenup, and it was a really confusing process. If you want to get a prenup without using HelloPrenup, you have to contact a divorce attorney before you're even married, which kind of starts the precedent of your marital journey off kind of a little weird. And also, hiring a divorce attorney for your prenup can cost a lot of money. The average cost is like $300 an hour. So it kind of depends on how complex your prenup is.

But if you're planning your wedding, buying an engagement ring, maybe trying to buy a house soon, you're going to put a prenup on the back burner because of the costs, even though it's a really important financial planning tool. So that's why I came up with the idea. I'm a software engineer. This is something that I think I could build is a platform for couples who want to get a prenup done really conveniently and for a fraction of the cost.

So I started working on HelloPrenup on my own in February of 2021, so a little bit over a year ago. And of course, I quickly found out that I don't know all the laws required, [chuckles] and I don't know how to write a good prenup contract. So I need either a legal advisor or an attorney to really help me figure these things out, especially because the law per state actually is different.

CHAD: Just so I understand the timeline, did you start it before you got married? Or did you end up doing a prenup through an attorney for yourself?

SARABETH: Ah, yes. So actually, we're getting married this Saturday.

CHAD: Wow. Okay. Congratulations.

SARABETH: Thank you so much. And we are HelloPrenup users.

CHAD: Okay, wow.

SARABETH: So we did our prenup with our platform.

CHAD: So you managed to get the product done before you got married so that you could use it?

SARABETH: Yes, yes. I wasn't going to get married without the prenup and going through an attorney. [laughs] I gotta...what is the expression? Like, reap what you sow or something like that.

CHAD: Yeah, or eat your own dog food is another one.

SARABETH: Yes. Dogfooding our own product has been amazingly beneficial for our team. So that's kind of where I left off in our story so far. I needed to find an attorney.

CHAD: I'm curious, you know, I'm a software developer too. I think we all have ideas. How did it become just from an idea to a thing you were really going to do? Where was that sort of switch? When did that switch get flipped?

SARABETH: When I came up with the idea for a digital prenup platform, I was actually unemployed. So this was kind of in the middle of the pandemic. I was previously working at a really awesome startup based in Seattle, Washington. But unfortunately, I was actually going through a lot of depression, and I felt really disconnected from my work. So I ended up quitting that job in November. So I took about three months off to recenter myself and figure out what I wanted to do next.

So when I thought of the idea for a prenup platform, I had the mental capacity to dig into the problem. And when I figured that it would probably be a profitable business, that's when I started to work on it full time. And I didn't have another job, so I was able to jump into it.

CHAD: Okay, so you then needed to find an attorney. You realized that was something you lacked.

SARABETH: Yeah, so I started doing some Googling while I was deciding whether this was something I definitely wanted to commit to, to see if there were competitor platforms. And I actually found HelloPrenup at that time. Of course, I wasn't involved with it. And so my co-founder now her name is Julia Rodgers Esquire. So she is a divorce attorney based out of Massachusetts. She actually had been building this product, which was completely aligned with my envisioning of what I was going to build. But of course, she had the legal background of it.

So I found her platform, and I noticed when I tried to sign up for the platform that the system was under maintenance. So I was like, huh, maybe they need technical help. So I actually ended up cold emailing her to see whether she needed any software help with the hopes that we could team up. And the next day, we just hopped on a Zoom. It's interesting talking to someone who you've never met before about possibly teaming up on something or potentially being a competitor to them. I made it very clear that I would much rather team up with her rather than try to figure this out on my own.

CHAD: That sort of sounds like a threat.


SARABETH: Oh my God.

CHAD: I'd much rather team up with you than have to do this on my own. [laughs]

SARABETH: Well, I really respected what she had built at that point. So she had put a lot of time into actually writing a lot of content and blogs around prenuptial agreements. So she had a really good base for the business. But it was really the software that she was running into issues with. So she had been struggling and working with overseas developers. So as an attorney, she didn't have a lot of experience project managing a software project like that. And especially with contract developers, you can't say, "I want this to be built in a sustainable, scalable fashion."

So there were a lot of bugs with the platform. The way I saw it was like, hey, she kind of has this MVP. And she's an attorney, so I think we would make an amazing team. I was also really excited at the prospect of being able to work with another woman entrepreneur. And we hit it off really quickly on our Zoom call. And yeah, so we've been working together since about March of 2021.

CHAD: Did you end up keeping what she already had from a technical perspective, or did you start over?

SARABETH: We completely started over. I tried to salvage the codebase that they had used. It was like Angular, which I actually despise Angular framework in general. I tried my best to clean it up, but they had no tests. They had a bunch of copy and pasted code. It was just kind of a mess. So that's when I really decided that Bubble would be a great option for us.

CHAD: Well, for those who don't know, Bubble is like a low-code/no-code platform.

SARABETH: Yes. So it's called It is, as Chad just said, you know, it's a low-code platform which allows you to actually build full-stack web applications. So unlike other website builders like Squarespace or Wix, you actually have a database or a back-end component to your application. And of course, for the majority of applications, that's really a requirement to build something actually useful for people.

So I'd been playing around with before we scrapped the codebase. And it was a good starting point because I'm still currently the only full-time developer on our team. And because we are using a low-code platform, we're able to move a lot faster with a lot of our feature development because there are a lot of things that had been done for us. So there are a lot of drag and drop features that we can leverage via different plugins.

CHAD: It's an interesting choice to me, not because I don't think it makes sense, but I think a lot of are a developer; you know how to code.

SARABETH: [chuckles]

CHAD: And I think a lot of developers, when faced with that choice, can't resist writing custom software.

SARABETH: Yeah. [chuckles] You know, I've always been torn between the development and the product world. And for a while, that was really a struggle for me deciding whether I wanted to be a product manager or a software engineer. So I settled on being a product-driven software engineer. So to me, the use case of like, I could write the traditional code, but it'll be a lot slower, or I could build the product a lot faster by using this tooling. That's where I land most of the time, like, the more time-efficient way to do things.

CHAD: From deciding to work together and starting to work together to okay, I'm going to rewrite this in Bubble; what point were you back online with the new version? How long did that take?

SARABETH: Yeah, so that took us about three months to get it relaunched, and so I was pretty happy with that. I mean, of course, there's still a ton of work that we're doing to build out the product, but to really get it back up and running and also in a more scalable way so that we actually can provide prenups across multiple different states now. So it's a lot more flexible in the way that it was built. So it took about three months to get it relaunched.

CHAD: So at what point then did you go on Shark Tank? [laughs]

SARABETH: So [chuckles] there were a lot of variables in play. And so, I was really thankful that we chose to use Bubble because the speed at which I needed to develop this was even more reduced. So we started talking to producers pretty quickly after we decided to team up together. It's a really unusual entrepreneur journey, I would say. I knew that it would make a good story because prenups are kind of taboo, as you mentioned. Television loves something a little spicy, a little bit dramatic.

So we started talking to producers, I want to say, in June or July, maybe even in May. And at that point, we hadn't relaunched the product. So we were really just pitching the idea. And we were pitching ourselves as founders to the producers and the exciting concept of how will the American public perceive a product that is a little bit taboo talking about prenuptial agreements before you get married?

If you're familiar with Shark Tank, you probably see that they have a lot of wedding-related companies that go on. But we were kind of flipping the script on that. So while I was rewriting the entire software, we were also going through the auditioning process of Shark Tank.

CHAD: I can imagine that's pretty intense.


CHAD: I think the closest thing I can think of is when you enter into an accelerator or something like that. You might be in it for three months. You're going to have demo day at the end. But with that, you're presenting to a group of people. It's not broadcast on national television.

SARABETH: Yes. [laughs]

CHAD: It's probably a little bit of a different thing, and there are no producers involved, that kind of thing.

SARABETH: Yeah, yeah, exactly. By the time we had gotten on the set of Shark Tank to pitch our products, we'd only really been relaunched for about a month and a half. [laughs] So we were flying...I'm so bad at expressions.

CHAD: [laughs]

SARABETH: We were pitching...

CHAD: By the seat of your pants.

SARABETH: Yes, that one. Thank you so much. [laughter] So we were really pitching the potential of our product. And we were just so ecstatic to be there.

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CHAD: When you went on Shark Tank, how much of what you said and those kinds of things was all you, or how much is it put together for the show?

SARABETH: Really, the only thing that is heavily vetted by producers is your pitch. So when you walk into the tank, and you give your 30-second to 2-minute spiel that's a bit more theatrical, you practice that over and over and over again. And it was really a fascinating experience. Because as a fellow software engineer, you know we're kind of more chill people, [laughs] more realistic. But they kept saying, "Bring more energy to it. Do big movements, maybe even do a dance or something." [laughter] I'm kind of living this double life where I'm writing software, and then I'm --

CHAD: In between rehearsals, you're opening your laptop and making another thing happen on the app, I'm sure.

SARABETH: Exactly. It's like, oh, okay, we have pitch practice tonight, and now I'm going to work on this core feature. Without it, we literally don't have a product. So the producers are very involved in your initial pitch. But then when you jump into the Q&A, when the Sharks start asking you questions, that's all you.

CHAD: That's really cool. So are you happy that you went on Shark Tank?

SARABETH: Yes, I'm so happy that we went on. I've always been a Shark Tank fan. I think it's been on for over ten years. Shark Tank has been something that's kind of kept me interested in being an entrepreneur. When I started learning how to code, I knew that I always wanted to start a business. And just seeing the number of ideas and the variety of businesses that people are able to build and putting that on a show is just a fascinating concept. So I was really happy to go on the show. And, of course, the impact on our business has been tremendous.

Really, it changed the trajectory of our business. We gain most of our customers through organic search. So most of our customers come in through Google saying like, how do I get an online prenup? By getting on national television, we are really thankful that news stations were now interested in talking to us. So by linking to our website, that helped boost our search engine optimization rankings. And so now we're actually a profitable business due to Shark Tank.

CHAD: That's awesome. So is the tech team still just you?

SARABETH: The tech team is me. And I have started working with another Bubble developer on a contract basis. But calling out to any software engineers or low-code developers, if you're interested in joining a legal tech company that's growing a lot, feel free to reach out to me. So I really do need to be hiring another developer. At this point, I am really the main developer working on things for a variety of reasons.

The first reason is that Bubble, while it is very quick to develop a product on your own from a technical perspective, it is lacking in features when it comes to collaboration with other developers. So with traditional code, you'll do code reviews on GitHub, and you'll just do like a diff. But the branching and the version control is definitely a little bit lacking.

So I'm trying to wait out the Bubble team. They have some stuff coming down the pipeline that will make it easier to do collaboration. But for that reason, it is a little bit easier as an entrepreneur using a low-code platform to be the sole developer because you kind of know exactly how everything works.

And then also, developers are really expensive. So we are actually a completely self-funded company at this point. So we're bootstrapped. We haven't actually accepted any investment at this point. We're a really conservative team. If we hire a developer, we want to make sure that we're able to provide them with a competitive salary and competitive package. And we're able to do that now. It's just a matter of finding the right person, which is actually a really interesting space because low-code developers are still on the up and up right now.

CHAD: I know you can't see the future. But do you foresee a point where either Bubble doesn't take you where you want to go, or you need to start augmenting it in some way?

SARABETH: I would like to push Bubble as far as I can. I think now that Bubble is getting a lot more recognition...and they just got another round of funding that was pretty substantial. I think that they're going to be improving a lot of things, especially when it comes to, like I mentioned, collaborating with other developers on the platform and performance. A lot of pushback that people give with low-code platforms is like, oh, the page won't load as quickly as if I wrote it with pure React or something like that. So I want to try and stay on the platform as long as possible.

If we really continue to grow, I would be willing to move back to traditional code. And we'd actually be set up for success in that way because we would have a fully functioning product, and half of development is figuring out what feature to build next. So we'd kind of say, all right, here's how it works. And then, while we're kind of maintaining our Bubble application, we can have a development team build it within our own platform. Does that make sense?

CHAD: It does. And I think with Bubble, it doesn't need to be all or nothing, right?


CHAD: You can use APIs. Or you can basically extend it with custom code if you really needed to using webhooks and that kind of thing, right?

SARABETH: Exactly. And that's the way that we've done it. So actually, the contract generation is written in Node.js JavaScript. And the reason I did that is because it's easier to process data in a sequential order with traditional code versus Bubble. And you can also hook into other APIs, like for us, we do a conversion of the HTML of the contract into a Word doc.

So we're able to call into a conversion API and then save it on AWS with traditional code, and you can do all that with Bubble. But it's a little bit more straightforward when you know what you're doing with just like JavaScript; you know a few lines here and there. Does that make sense?

CHAD: It does, yeah. I'll be super interested to see how far you're able to push it and what those things you need to do outside of Bubble are.

SARABETH: Yeah, I'm really excited to try to push Bubble as an option for entrepreneurs. We were actually the first low-code platform to be shown on Shark Tank. So every Bubble developer on Twitter was really excited about it.

CHAD: [laughs]

SARABETH: So I think it's a really interesting spot to be in right now.

CHAD: Yeah, from a technology perspective, I think that that's one thing we've talked about. And you addressed the other thing that sometimes people say is a promise. Like, it is a commercial platform. It's not an open-source platform, and you're building entirely on top of it. And so that presents a certain amount of risk that like, they might go out of business. You know, they're a VC-backed company, and maybe they'll go out of business. And then where would you be? The fact that they've just raised a significant additional round of funding mitigates that somewhat, but it's still a concern, right?

SARABETH: Yeah, it's definitely a concern. And it's something that, as a software engineer, it's terrifying to know that you're relying on someone else for your livelihood and now the livelihood of multiple people on our team. So it is really scary. You cannot export your code from Bubble. But I believe they have said that if for some reason they go out of business, they will allow you to do that.

I'm sure whatever code you export from it is not going to be very pretty to look at. So it probably makes sense to write it from scratch. But I think at this point, I'm really happy with where we're at. I like remaining a really lean team. And using different tools in simple ways and trying to keep our product as simple as possible has really helped us grow.

CHAD: What's next for HelloPrenup? Where are you setting your sights on? What's keeping you up at night now?

SARABETH: Ooh, so many things. We do have an exciting investor coming on. I can't say exactly who, but they were really involved in building one of the largest legal tech platforms out there today. So we're really excited to be partnering with them and be building out our network across all 50 states. Right now, we're actually in, I believe, 32 states. You can use our platform to create your prenuptial agreement. And so, we're excited to be starting to onboard attorneys to the platform. So that's one of the things.

Another thing that's on our radar is keeping up with, you know, it's hard to say the trends of what's going on with Web3. But we do have some things that are related to Web3 that we'll be tackling in the next probably a year or a couple of years when it comes to financial data. Yeah, so those things are kind of on our radar of our product.

And then, on the near term, we are doing a lot of work to try and normalize the entire conversation around prenuptial agreements. We partnered with The Knot, which is one of the largest online wedding registry websites. And we've been writing a lot of blogs on their website that talk about the educational side of prenups. And we're actually going to be launching gift cards.

CHAD: [chuckles]

SARABETH: So you can list a prenuptial agreement on your wedding registry, and people can help support it. So there are a lot of initiatives that we're going to be doing on the product development side and then also kind of on the marketing education side of the business. As we start to grow, I'm trying to pull my attention away from those things. But sometimes, it's really hard because some parts of the business that aren't technical are fun to get involved in. And I'm sure you run into that or when you were scaling thoughtbot getting distracted by other parts of the business because they were just interesting. But there's a lot going on right now.

CHAD: That's exciting. You mentioned earlier that you hadn't taken investors yet. And so is it about that scale that's causing you to take one on now, or what's going on there?

SARABETH: So we're profitable. We don't need an investor, which is we're so thankful for that. So it's really a strategic partnership for us.

CHAD: Well, that's really cool. I'm excited to hear everything you have going on. And I really wish you luck in everything that you're doing.

SARABETH: Thank you so much.

CHAD: So if folks want to find out more about HelloPrenup, follow along with you, get in touch with you; where are all the best places for them to do that?

SARABETH: You can check us out on And we're on Twitter, Instagram, LinkedIn. Just tweet at us @HelloPrenup, and one of us will respond. It'll probably be myself or Julia. So you're able to get into contact with us if you have any questions. And of course, if you are a developer who is looking to join a really fun, women-led legal tech company, hit me up.

CHAD: Awesome. You can subscribe to the show and find notes with links for everything that Sarabeth just mentioned, along with a complete transcript for this episode at If you have questions or comments for me, email us at And you can find me on Twitter at @cpytel.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore.

Thank you so much for joining me, Sarabeth. I really appreciate it.

SARABETH: Thank you so much.

CHAD: And thank you for listening. See you next time.

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