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Scott Orn

Scott Orn, CFA

Sarah Jacobson, co-founder of FairStreet, discusses how FairStreet helps insurance brokers enroll older adults in the right health insurance plans

Posted on: 07/19/2022

Sarah Jacobson

Sarah Jacobson

Co-founder - FairStreet

Sarah Jacobson of FairStreet - Podcast Summary

Sarah Jacobson, co-founder of FairStreet, discusses how FairStreet helps insurance brokers enroll older adults in the right Medicare health insurance plans, and simplifies and streamlines the enrollment process.

Sarah Jacobson of FairStreet - Podcast Transcript

Scott: Hey, it’s Scott Orn, Kruze Consulting. And thanks for joining us on founders and friends for another awesome podcast. Let’s give a quick shout out to the Kruze Consulting accounting team. We’re very fortunate, we have a ton of people at Kruze who work on the monthly books for our clients and get them all set up, due diligence ready, rocking every month, answering all the clients’ questions, making all those adjustments. And there’s no better moment for a founder, and for us really, when the founder says, “Hey, I think I’m going to get a term sheet. Are my books ready for diligence?” And we get to say, “Yes, they are, fire away, send them over, give them access.” That is a great feeling. It’s the feeling that lets us know we’ve done a job very well done, and nothing is better than watching that cash hit the bank account. So, if you are a venture back startup, you’re going out to fundraise, maybe check us out. Check us out at We love what we do. At taping here, I think we have 575 clients. Clients raise over a billion dollars this year, so we know what we’re doing and hopefully we can help you be successful in your fundraise. All right, let’s get to the podcast. Thanks.
Singer: (Singing).
Scott: Welcome to founders and friends podcast with Scott Orn at Kruze Consulting. And today my very special guest is Sarah Jacobson of FairStreet. Welcome, Sarah.
Sarah: Thanks, Scott. So nice to be here.
Scott: Yeah, it’s great to talk. We’ve had an email relationship, because I’ve been an admirer of what you’re doing. We will get into that a little bit, but it’s so great to meet you in person and do the podcast and thanks for doing the video version of the podcast.
Sarah: Of course.
Scott: Maybe you can just start off by retracing your career a little bit and telling us a little bit about how you had the idea for FairStreet.
Sarah: Of course. So, FairStreet fundamentally helps older adults enroll in the right Medicare health insurance plan when they turn 65. And we’re taking a bit of a different approach here. We actually build software for the insurance broker, and most people end up working with an insurance broker when they turn 65 and enroll in Medicare. It’s probably pretty different than how you or I might think about enrolling in insurance, but to walk you through why this is such a problem and how we got into this and why two 20 something year olds are really passionate about people over 65. Can talk about how we landed on FairStreet, but also, where my career was before FairStreet. And that led, Tori, my co-founder and myself to this problem space.
Scott: And even just before, I am a huge broker person. So, at Kruze, we have a benefits broker, we have general liability, employee liability insurance broker. I actually fundamentally believe in the experts in the channel who actually really know what they’re talking about and do it all day long.
Sarah: Exactly.
Scott: So you’re preaching of the choir right now. I actually love what you’re doing. So, yeah. Give where you’ve been and then the epiphany moment.
Sarah: Sure, absolutely. So, a lot of different things led us to FairStreet if I think back on my career in particular, I have always been interested in healthcare. I was pre-med all throughout college thinking I’d become a doctor. I studied human biology at Stanford, and then pivoted into digital health after I did this really foundational internship at Rock Health, which is an early stage healthcare investor. Yeah. Got exposure to all these amazing, inspiring companies that were changing their fields using technology. And that was the start of an epiphany that I really wanted to do digital health and use technology to impact healthcare at scale. Backing up even further, I’m not from the US, even though I sound American. And so, I think part of why I’ve been interested in US healthcare and why it’s so broken is because I grew up in the UK. And for most of my childhood, I took for granted the fact that, if me or my family or my friends ever got sick, no one ever worried that they could afford their healthcare. That is a uniquely American problem. And when I came back to the US for college, I was really confused, but also fascinated. And so, I think that’s what led me initially down the path. After college, I ended up getting a job with Stride Health, which is a Rock Health portfolio company. And we were helping people enroll under the Affordable Care Act. So, it was really, really meaningful work. This was a direct to consumer brokerage. We were helping people, that had honestly been uninsured for up to a decade, get subsidized healthcare and navigate what is a really complex experience. I was really proud of the work that we were doing and could see the impact we were having on our customers, when they went from not having insurance to being able to finally go to the doctor.
Scott: Yeah. And you don’t know this about me, but 15 years ago I started a nonprofit called Ben’s Friends with my buddy Ben, who had a rare brain aneurysm and survived. We were in business school together. And we started this support community, it’s a large, rare disease support community now. But the Affordable Care Act was huge for that constituency, because, like you said, that’s probably where you’re going with that. A lot of those people had not been insured for a long time because of preexisting conditions.
Sarah: Right.
Scott: And so it’s amazing to hear you did that work, because you were helping the people we were working with to help to make their life better. That’s super meaningful to me too.
Sarah: It was incredibly meaningful. And interestingly I joined right before Trump was elected. And I had assumed that the ACA would be unchanged over the next four years. And it was, I think, all the more meaningful to be there during that time because there was a lot of political forces trying to undermine the ACA. And so, it was definitely an interesting time to be at Stride, but the work and the impact we were having on our customers was just so clear. After Stride, it was kind of interesting, Square actually reached out and recruited me to work on an employee benefits product for the small business owners on Square’s platform. When they reached out, I had no idea that Square was doing anything in healthcare or the benefits world. So I’m really glad I took the call. But ended up building out a really interesting employee benefits platform for these small businesses, and health insurance was the most important part of that.
Scott: Oh, I didn’t even know they have that either. That’s really interesting.
Sarah: Yes, it’s embedded into the Square payroll solution.
Scott: Yeah. That’s smart. Super smart.
Sarah: Mm-hmm. So, from there, around that time I started to get the itch that I knew I wanted to start a company. And at the time I knew it would be likely in the insurance space because that was my background and my passion. And I’d come to this understanding that, for better or for worse, in the US health insurance is the biggest lever that we can pull to impact how someone accesses care. But, didn’t have a co-founder, didn’t have an exact idea. So, I ended up going to Stanford business school and the idea there was to figure out both of those things. And was incredibly fortunate that happened. I met my co-founder Tori at an admitted students event before school even started.
Scott: Oh your first experience, the first day on campus kind of thing?
Sarah: It was before the first day on campus. We were at an admitted students event and I overheard Tori, in a completely different conversation say something like, “Yeah, I’m coming to GSB because I want to start a healthcare company.” And I think I elbowed everyone out of the way. I was like, “Hey, I’m Sarah. We should meet.”
Scott: That’s awesome.
Sarah: And so we ended up working together the entire two years, exploring this intersection of both insurance and aging. Both of us are really close to our grandparents. And so we wanted to build a company that made healthcare more accessible and affordable for older adults.
Scott: And you have a really… Well, let’s talk about your grandfather real fast.
Sarah: Sure.
Scott: Because it seems like, we were talking before you turned the mics on, I was close to my grandfather too. And it seems like it’s been a guiding light, as someone who really touched you in life. Maybe talk about-
Sarah: Yes.
Scott: Talk about that and how it… Because now I assume with FairStreet, you’re helping everyone’s grandfathers and everyone’s grandmothers. And it’s like, oh, I’m spreading the love that was generated from my one grandfather to the whole-
Sarah: Exactly.
Scott: Community.
Sarah: Exactly. I grew up really close with my grandparents on my dad’s side. My grandma passed away in 2017, but both of them are so vibrant and full of life. I was telling you this earlier, but when I was young, I always wanted to be old because they were so cool and so full of life and had so much energy that I always thought it would be really fun to be 65. And I didn’t understand that actually, most people don’t think that way. Most people want to be young and I wanted to be old. And I really credit that to my grandpa in particular because just last month he was actually on a around the world trip to Egypt with his now girlfriend, who’s also 80 herself. And they just have this amazing life together and truly live every day to its fullest.
Scott: Oh, that’s awesome.
Sarah: And in part, I recognize now that his ability to live that sort of life is because he’s been very fortunate to have the right healthcare. And even though, it’s not that he’s lived a life without health issues, but every single time something has come up, he’s been very fortunate to get the care that he needed and was able to recover fully. And be able to afford the care that he needed. And I can recognize that now with the benefit of hindsight. And in talking to hundreds of people turning 65, I’ve recognized that experience is actually an outlier. And so, with FairStreet, our ambition is to help more people live like my grandpa.
Scott: That’s really amazing. Yeah. Because probably some folks, especially who aren’t covered or don’t know how to navigate Medicare, the little things don’t get treated and then it turns into a big thing and all of a sudden it’s life threatening. Or it just takes 5 years or 10 years off their life expectancy because they just didn’t know.
Sarah: The statistic that makes me really sad is 30% of seniors do not fill their prescriptions-
Scott: Oh my gosh.
Sarah: Due to affordability. Right? And that’s totally avoidable. If we can help people get into a plan that actually covers their prescriptions and identify where they’re eligible for financial assistance. That’s a statistic that just makes me so sad and is a uniquely American problem.
Scott: Yeah. Oh my gosh. That’s crazy. So you’re funneling this super positive love from your grandfather-
Sarah: Yes.
Scott: Into FairStreet. Maybe explain what FairStreet is. And you have some pretty interesting, you’ve iterated on this a little bit, and it’s really come together.
Sarah: Yes. We have been through a few different iterations of FairStreet, all with the idea of how do we increase access to affordable care for older adults?
Scott: Yep.
Sarah: FairStreet helps seniors enroll in the right Medicare health insurance plan when they turn 65. And we’re doing that by empowering the independent health insurance broker. And how we happened upon that insight, actually, when we first started FairStreet, we were like many other startups building a direct to consumer solution. The idea was we need to build a better digital shopping experience for people to navigate this really complex decision.
Scott: Yep.
Sarah: What we found by actually going out and talking to hundreds of people and trying to build this product is that it’s not the way that people shop. Part of the reason why most, and by most I mean 60%, of seniors turn to an independent agent is the level of complexity is through the roof.
Scott: Yeah. Yeah.
Sarah: If you think about the last time that we enrolled in a health insurance plan, maybe there were two or three options. I always find it really overwhelming to choose between two or three. And my medical conditions, luckily are pretty simple. When someone’s 65, they’re choosing from an average of 57 different plan options.
Scott: Wow.
Sarah: And the stakes are enormous. People are taking quite a few medications. They likely have some chronic conditions that they’re managing, it’s a really stressful high stakes decision. That if you get wrong at 65 can impact your options for the rest of your life.
Scott: That’s crazy. And we actually just did our annual enrollment at Kruze and you’re right. We had our brokers do multiple presentations to the whole company. There was multiple PowerPoints shared. There were video calls that people could watch on their own time. And that’s all. And our population is really younger or mid forties, mid fifties people. But human beings need that explanation. They need to be able to ask questions. They need to be able to ask questions in a discrete area too, not in front of everyone, but be able to-
Sarah: Exactly.
Scott: Kind of, hey, I’ve got this going on, or I don’t want this to be public, but this is what’s going… So I really like what you’re doing, because I think giving those people, the experts, the tools to serve the constituency really efficiently makes so much sense to me.
Sarah: Right. And you’re so right, because it’s such a specific process that people go through with their agents. No two individuals are alike. And so, these brokers will literally spend hours with their clients, across a few different meetings. Understanding what prescriptions are you on? What doctors do you want to keep seeing? Each zip code has different plan availability and those brokers are experts in their zip codes and the plans available in that region. The interesting part is that these independent agents are running their business off of spreadsheets and outdated government websites. And it’s pretty incredible that they’re building impressive small businesses. They’re mostly solopreneurs. But again, just with zero tooling. And so FairStreet builds an amazing vertical platform for these 700,000 independent agents nationwide to run and scale their business. So, that they can spend more of their time on those human conversations where they’re building trust, and they’re educating, and they’re helping people weigh choices, but not spending their time copying and pasting data on the back end or wrangling systems that just don’t work together.
Scott: Hey, it’s Scott Orn, and we’re going to take a quick break from the podcast to give a shout out to the Kruze tax team. Gosh, it’s so nice to have an in-house tax team. I can’t even tell you. We have some really amazing professionals on the team. It’s over, I think it’s 13 people now. And we do everything from your federal and state income tax return, state franchise tax filings, R&D tax credits. Those are pretty popular these days. And guess what? They’re there for you when you go through diligence. A lot of people don’t know this, but you actually go through tax diligence, not just operational financial diligence, but you do go through tax diligence. So, it’s nice to have Vanessa Kruze on the phone with your VC’s and with the accounting firm they hired to diligence all your stuff. And the law firm they hired to diligence on your stuff. Vanessa knows what she’s doing. She’s done this a million times. And it’s not just Vanessa. We have a really great team of past professionals that will do those calls too. It’s sometimes the difference between getting around close or having it taken another two weeks because something was disorganized and the tax compliance wasn’t done correctly. We hear those horror stories from clients that come to us. So, hey, if you want Kruze’s tax team on your side, we’re here for you. Check us out at Thanks. There’s probably a lot of… I’m not sure about this, it’s more of a question. But by building the workflow and the process for these independent brokers, you’re probably reducing error rates or slow response rates or all these.
Sarah: Yes.
Scott: The whole system is getting greased. I’m assuming. Every everyone’s getting… And you’re probably saving the brokers a lot of time and energy, and they’re probably able to expand their practice too, because of FairStreet.
Sarah: Exactly. So, the impact on the broker is that they’re both saving time and focusing their energy on the parts of the business that they actually enjoy and where they add value. And they’re growing faster, because all of the brokers we work with grow by referral. It’s really interesting. These are hyper local businesses.
Scott: Yeah. Yeah.
Sarah: And if you can provide a really high level of service to your clients, they will refer all of their friends and family to you. And so, the FairStreet software makes brokers look incredibly professional. It provides a great experience back to that turning 65 client, and they will tell everyone about it. And so-
Scott: That’s amazing.
Sarah: And from the client’s perspective, they get to work with a broker that is on top of it. They’re organized. They show all the options available in a zip code. They get to work with really easy to use software. So, the client has their own portal on FairStreet to manage their prescriptions, their doctors, their plan information. So, a large part of what we do is empower the consumer to engage in this decision. But the hard work is still being done by the broker.
Scott: Yep. Are you able to let friends and family access that portal too? Because I could see, my parents are both still relatively young, they’re in their seventies, they’re they’re with it. But I could see other situations where maybe 10 years from now I have to be more involved in their care decisions and things like that.
Sarah: Right.
Scott: Is that a feature you provide?
Sarah: It’s a really good question. Not something we’re doing at the moment, but family caregivers are very involved in particularly older adults or older seniors decision making. We see above 85 years old, that’s where you’re starting to see the adult children who are also, 60, 65 years old getting involved in the care decision. And what’s really interesting is you’ll see these independent agents serving both the adult child, who’s 65, and their parent, who is 90. And so it’s really a family affair and they will go to the meetings together.
Scott: Awesome. I love it.
Sarah: It’s so interesting. Yeah.
Scott: I love it. I love it. Yeah. The word of mouth makes so much sense too, because like anything in life, if you’re doing a good job and you’re a subject matter expert, that’s really going to… Especially if you’re in… And even us, when you’re independent and don’t have huge amounts of money, you basically deliver really great service to generate those word of mouths. And I’m sure that’s what they live every day. That’s their business plan is just do a great job, and get brought up at the weekly poker game or the weekly whatever activity and-
Sarah: Exactly.
Scott: Get clients that way.
Sarah: Right. And there are some things we do to help local independent agents boost their visibility. Many don’t have a website. We have a website template that we can help them stand up.
Scott: That’s cool.
Sarah: Many don’t have… Whether it’s a Medicare 101 educational material, or maybe they’ve built it in Microsoft word, we can give them a template for that. So a lot of what we do is helping them look professional.
Scott: Yeah.
Sarah: And be visible in their communities.
Scott: Yeah. The website actually seems like such a small thing, but it’s probably really important because A, they have to spend a bunch of money somewhere else doing that. But B, you can deliver the best experience that’s been tested over thousands and thousands of brokers. So, you know what people are looking for.
Sarah: Exactly. It might not be a big deal for us to stand up a Squarespace website, but it’s a little intimidating to someone that isn’t in the tech world. And so that’s something we can provide and we have a great template that, to your point, has been tested with lots of seniors and lots of other agents to make sure that it’s conveying the right information.
Scott: That’s that’s fantastic. Now, where are you in your company’s journey? You’re a seed stage company, are you actively signing up brokers? Are you in the beta version? Where are you in your life cycle?
Sarah: Yeah, it’s a great question. So, we actually just graduated from the pair accelerator in May. And during that time we were laser focused on launching our first alpha cohort. So right now we’ve launched our alpha cohort. The product is live. We have dozens of experienced Medicare agents up and running on our platform and using us to run their entire business. And we’re in growth mode right now.
Scott: Oh, that’s awesome.
Sarah: So we are signing up new agents. We are building product. We’re in a really fun stage right now where we have the core nugget that’s working in product market fit with our core user base. And there’s a lot that we’re learning and experimenting with to grow beyond this point. And we’re team of four, and we are actively hiring.
Scott: That’s amazing. And are you seeing the same word of mouth amongst the brokers? Because they do they really, if it’s such a local business, do they even really compete with each other? I’m assuming the east bay… We were talking, I’m in Danville, the Danville expert brokers know other brokers throughout the industry, or they’ve gone to conferences, is the same word of mouth happening for you?
Sarah: Yes. We get a lot of referrals. It’s a really well networked industry.
Scott: Yeah. [inaudible].
Sarah: And so we have seen our existing alpha cohort referring their friends in neighboring counties or neighboring states.
Scott: Yeah.
Sarah: That’s absolutely happening. It works to our advantage. If we can do a really great job for our existing cohort of agents, they will continue to refer other agents to us.
Scott: That’s really cool. If there’s a broker out there or the broker gets this forwarded to them, how does the signup process work? They go to your website. Is there a accreditation check or… I just don’t know how someone gets involved.
Sarah: Sure. It’s a great question. So, for any brokers listening who are interested in FairStreet-
Scott: Yeah.
Sarah: Go to our website. So, the website is Put your name in, you can either sign up for, we do live demos every single day led by yours truly, or you can sign up for a one on one appointment and someone for our sales team will reach out and get in contact. But it’s a pretty seamless process to get up and running with FairStreet. Right now we’re working with folks that just do Medicare, either as part or all of their practice, and we help you scale your business.
Scott: And it’s probably a low… I’m again, more of a question, but I’m assuming you make it pretty easy for them to just try you out. So, they’re not buying some giant piece of enterprise software or something like that, where there’s no going back. I’ve done that in my career a few times, much to my chagrin. I’m the kind of person who likes to try something out before I fully commit to it.
Sarah: Yes.
Scott: Is that your onboarding model, how you get the brokers going?
Sarah: Exactly. So, we’ll get people set up and they can test the software and make sure it’s the right fit. An interesting piece about our model that we haven’t gotten into, is we actually don’t charge for the software. We work as an agency. And so, in the Medicare world, much like in real estate where a real estate broker has to work with a brokerage to sell a house-
Scott: Yeah. Yeah.
Sarah: In Medicare, a Medicare agent has to work through an agency to sell each plan.
Scott: Interesting.
Sarah: And agents get paid on commission whenever they enroll someone in a health plan. That commission is the same, no matter which plan they enroll someone in.
Scott: Yep.
Sarah: The agency also earns a commission when one of the agents enrolls a senior in a plan. So long story short, we function as the agency and earn a commission paid by the insurance company. That allows us to make the software free-
Scott: That’s super interesting.
Sarah: To the independent agent.
Scott: Yeah.
Sarah: And they keep their full commission. What we earn is on top of that. So, it’s a really synergistic business model where our success is totally aligned with our customers, and the software itself is free
Scott: And they’re going to pay that commission somewhere because they have to be part of an agency anyways. Right?
Sarah: Exactly.
Scott: You’re not really taking money out of their pocket so to speak?
Sarah: No, exactly.
Scott: Yeah.
Sarah: The commission that we earn is on top of what the agents were already earning before working with.
Scott: Yeah. That’s super cool. So, you’re basically offering, it’s a free service that makes their business more efficient and-
Sarah: Exactly.
Scott: That’s, that’s the whole [inaudible].
Sarah: It’s really only upside for the agents that we work with. And if we can communicate that well then the light bulbs go off.
Scott: Yeah, yeah.
Sarah: And it’s a really fun sales cycle to go through.
Scott: I’m sure you’ve done end user testimonials or things like that too. Because I could also see the brokers being like, well… Because there’s the whole Gartner adoption curve that we all have to deal with in life if you’re in the tech world. I can see some brokers being a little slower to adopt stuff. But when they see their clients have the light bulb go on.
Sarah: Yeah.
Scott: I’m sure it makes the whole sales process a lot faster.
Sarah: Absolutely. One of the best… So, we definitely lean a lot on testimonials and our customers will do reference calls for other customers, which is fun.
Scott: That’s cool.
Sarah: But when they see their clients fill out the client portal or interact with a piece of material that we’ve provided to the agents.
Scott: Yeah.
Sarah: That’s the most self-reinforcing moment where it’s like, my clients are having a better experience because of FairStreet.
Scott: Yeah.
Sarah: And that’s why brokers get into this in the first place, is to provide amazing service to their clients, help them with this decision. And our software helps them do that.
Scott: Yeah. I love it. I love it. So, you’re a four person company right now-
Sarah: Yes.
Scott: Which is amazing, you’ve accomplished all this. I always tell startups, the velocity of your progress is the best indicator of ultimate success. But it sounds like you’re going to be staffing up and hiring. You said you’re in growth mode now?
Sarah: Correct. Exactly. So, we are actively hiring. We’re hiring for product design, engineering, and growth. Fundamentally our philosophy around hiring is we hire just awesome individuals and we stay lean. And every single person at this company has enormous impact. And so you’re right, we’ve done a lot with very few people on our team. And I think that’s a testament to the just incredible individuals that we brought on.
Scott: They have impact not just on the company, but they have impact on the seniors who are signing up. Because that is a scary moment, you hit 65 and all of a sudden you’ve got to make these giant life decisions. So, I’m sure there’s a real sense of satisfaction with helping the people whose life is being improved via FairStreet.
Sarah: We love hearing from seniors.
Scott: Yeah.
Sarah: And a big part of our product process is doing tons of user research and then closing the loop with that end consumer.
Scott: Yeah.
Sarah: And honestly I think for a lot of us, that’s our favorite part, is seeing the tool live and impacting that 65 year old, helping them navigate what can be an incredibly scary decision. And then helping these small business owners build a business. We love empowering small business owners. It’s what I loved about Square in particular. And you get to do that for these Medicare agents as well.
Scott: We have the same thing. We have a saying, Kruze cares more. And everyone at Kruze buys into that. It’s exactly like you, that can actually take your company really far. When everyone’s that you hire is bought into it, or people who aren’t bought into it, they quietly leave because they never were like signing up for this mission of improving people’s lives and things like that. So, I have a lot of respect for you for instilling that. And it’s like a garden, you got to water it and keep it alive and make sure that heartbeat is going throughout your company as you get bigger. Because it’s easy to lose that a little bit.
Sarah: Exactly. I think we’ve been very lucky to attract the type of person that is very mission oriented, mission driven. That’s what motivated myself and Tori as founders to get into this in the first place. And it’s a core piece of our DNA that we are dedicated and committed to preserving going forward. Because again, the whole reason why we got into FairStreet, the whole impetus for wanting to start a company, is to help seniors have better healthcare in retirement.
Scott: Yeah, amazing.
Sarah: And this is the way that we can have the biggest possible impact.
Scott: Yeah. I love it. Well, I should be respectful of your time here, so we should wrap up. Maybe you can tell everyone, give the website out again, how to reach out if they’re interested or how to refer you or one of the brokers you work with to a loved one that might… The people listening to this podcast, there’s probably some post 65 people, but not a ton. So how can someone take action on be behalf of a loved one?
Sarah: Absolutely. So, in both of those scenarios, whether you are a broker interested in FairStreet, you’re interested in learning more about working at FairStreet, or you have a loved one going through Medicare. I think the best way is, come to our website. It’s or send me an email. My name is Sarah and my email is
Scott: Awesome. Sarah with an H for everyone out there-
Sarah: Sarah with an H.
Scott: Listening to this.
Sarah: Exactly, the right way.
Scott: Yeah, you got something really cool here, Sarah. I’m really happy for you. It feels like it’s just the tip of the iceberg. It’s cool. You’re going to change a lot of people’s lives. I really respect that. Well thank you for coming on. Really appreciate it and wish you the best of luck.
Sarah: Thanks, Scott.
Scott: Thanks, Sarah.
Singer: (Singing).

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