Spencer Hilligoss is a former Silicon Valley tech leader, who helped grow several billion-dollar companies before transitioning into real estate. He’s the founder of Madison Investing, which focuses on raising capital for real estate syndications, and he’s invested in over 5000 units.

In November 2019, Spencer “retired” from his lucrative technology career – leaving behind the $4B loan origination teams he built at LendingHome. Now, he is focused on spending time with loved ones and growing Madison Investing by helping passive investors achieve their goals.

What You’ll Learn In Today’s Episode:

  • Trust, but verify. In Spencer’s words, “Everyone starts with an A,” but then he verifies their track record and information, going as far as running background checks. Spencer is a trusting person by nature, so he took the time to develop a system and process for vetting potential deal sponsors. He believes that even if it’s a deal brought to you by a sponsor you’ve done a dozen deals with, your loyalty has to be to your investors, not the sponsor.

  • Spencer took stock of his surroundings, background, and environment, and developed a strategy of investing that worked for him and his family. In the words of Spencer’s mentor, “You’re in a money state, not a deal state.” 
  • You have to learn to say ‘no’ a lot. Whether vetting sponsors, deals, or even investors. Establish criteria that work for you and your investors, and stick to it. This will likely mean saying ‘no’ much more than ‘yes.’

Ideas Worth Sharing:

“It’s like the Silicon Valley lottery, most of these things fail.” – Spencer Hilligoss

“They want the expertise of a person who is human. They are not going to go through a phone-tree to get advice on how to buy a house.” – Spencer Hilligoss

“I genuinely believe more people should have access to these investments.” – Spencer Hilligoss

Resources In Today’s Episode:

Books Mentioned In Today’s Podcast

Enjoy the show? Use the Links Below to Subscribe:




Mark: Today’s guest is a former Silicon Valley tech leader who helped grow several billion-dollar companies before transitioning into real estate. He’s the founder of Madison Investing, which focuses on raising capital for real estate syndications. And he’s invested in over 5,000 units. I’d like to welcome Spencer Hilligoss.

Spencer: Mark. Thank you so much for having me very excited to be here. I appreciate the invite.

Mark: Yeah. Thanks for joining. So, you were in lucrative tech positions. What was the impetus to shift over to real estate?

Spencer: I grew up in the Bay area, California. It’s a pricey coastal market, as many folks who were from outside this region. What you might not know is that the local business of tech companies and software companies, it has this unwritten financial plan that people talk about when they join real estate tech companies, but they don’t necessarily talk about the downside of it and it’s full of it.

I worked at five software companies, a few of which were all unicorns. That means they’re valued at over a billion bucks and people joining these types of companies, regardless of any bigger narrative or positive Kool-Aid that they might say about changing the world, which is pretty prolific as well. They’re largely joining these companies because they want to get early stage equity and have joined the next Facebook or join the next Google because they want to get that huge exit. And so, I really chased after that right after college.

Mark: A bit of a get rich, quick mentality.

Spencer: Very much so. It’s so much like a lottery. It’s like a Silicon Valley lottery. Most of these things fail. And so, I went straight into that. And 13 years later at the end of this career. I retired five months ago, right before COVID-19 circle the globe. I didn’t necessarily plan on that timing, but thanks to real estate and real estate investing for cash flow, we’re in a great spot. I wasn’t totally up front when I say I’m new to real estate as of four years ago, the thing I used to be embarrassed about was that I grew up in a real estate household.

My dad was one of the most successful residential real estate brokers in the country back in the nineties. And so very educational in hindsight, when you’re surrounded by entrepreneurship, that’s growing like a rocket ship, you learn a lot, but I was forced to work open houses as a teenager. And I absolutely hated it. I wanted to get out of there. I was running, screaming away from that. Part of the reason I was there because all my friends worked in my dad’s real estate company.

So, flash forward, probably the last thing I’ll mention on this backstory was that we also learned a lot on the harder side of things, early stage or early in life. So, my dad’s business also at the chronic crumble, not too long after that, we went into this period of time where I lost my younger brother to pediatric cancer. This is a long time ago now, but he passed away, triggered a divorce from my parents and a bunch of other pretty tough stuff happen. And so, as a result, I watched the growth and I watched the shrinking and that all happened when I was probably entering college. So, I was able to take away some really tough things to reflect on. And I didn’t really know at the time that would lead me to having some principles that I now apply to our life in our family.

Mark: Hurdle.

Spencer: Yes. It’s really hard as this stuff that stays with you and you can channel that stuff into positive outcomes. That’s what we strive to do. And I learned watching my dad’s business crumble was like, that was active income, lots of transactions that are one off. If you’re a broker, you’re a flipper, you’re a wholesaler. That’s like Robert Kiyosaki dumped the bucket on the table moment. And it’s great when that happens and then the money is gone. The pipeline is what I realized if we had had that as a family.

And now that I’m a dad and I have my own kids, if I can create that pipeline dynamic and have streams of income coming in, I can get away from that Silicon Valley narrative of chasing this equity that may or may not ever materialize. And I can get away from having to work W2 job, to put food on the table for my family and all that good stuff. So, we now play financial offense, financial defense, and there’s some sub bullets that we’ve got to be even very nerdy style, but behind those things, and the way you invest.

Mark: That’s you and your wife have this strategy that you employed.

Spencer: We did. When I say we, Jennifer Morimoto is my co-founder in Madison Investing as well. When people ask what is your strategic advantage? That is our strategic advantage. It’s the fact that if you can get through the alignment phase, if you want to call it that. Because we had a couple of weekends where we were planning, I kid you not, we took the whole weekend before we launched the business. And we said, if we’re going to do this, we got to be a hundred percent aligned on everything. And there were tears, there were arguments and there were reconciliations. All that cycle ran multiple times over in one weekend. And so now we have this beautiful relationship and we’re thriving better than we ever have before.

Mark: So, you had to go through some pain to get completely aligned, but it was worth it.

Spencer: Yes, exactly. Right.

Mark: So how did you wade into the real estate space?

Spencer: It was very interesting how I stumbled my way into the investing side of real estate as an adult. So, on my 4th start-up company is one of those hot start-ups. It was going very well. Eighteen months into that I had an infant son, our first son, we now have two and I was super burnt out. I was wondering what’s the exit strategy here? And that’s kind of what lit the fuse. A mentor of mine, he nudged me into going in and taking a leadership role at a real estate tech company.

Mark: He was a tech guy; someone you knew from your tech world.

Spencer: Exactly right. Yeah. He was a tech guy. He was one of my earliest mentors in my corporate career. I have had him to thank so much for the learnings and tough love that I got along the way. The tough love part is very critical. And so, he nudged me to go into a company called LendingHome and it’s the biggest fix and flip lender now in the country. When I got there in 2016, they were doing 150 flip loans a month, I had to go in and turn around the loan origination organization and eventually scale that up to become a $4 billion origination team. And so, we did that and within about six months of being there, I was getting this feedback and pressure from my colleagues and they were all saying, dude, you should just go flip on nights and weekends.

Mark: Hopefully. Okay.

Spencer: And I was like, I have an infant son, the day job I have here guys is very demanding. And I do still prefer to have something called life outside of all this work. And I could barely swing a hammer Mark. So, I’m not a flip rehabber guy. YouTube saves me every day around my house. So ultimately, I looked way down the rabbit hole at passive investing. We ended up buying local rentals because we weren’t ready to go buy out of site. And we bought a duplex in Vallejo. We then ended up buying long distance. We got some turnkey properties out in Kansas City. We still have all these residential properties now and their cash flowing and it’s helpful.

Mark: But you’ve held everything?

Spencer: We’ve held them all so far. Maybe at some point we’ll sell them, but right now they’re doing fine. Still have to do a couple more things than I would prefer to, which is why I typically say, if people ask are rentals passive? I say, “They are semi-passive”. Even with a property manager, residential rental is not passive. It is semi-passive. So, I’ll save that soap box, but we eventually started LP passive investing in multifamily. And now we invest in self-storage as well as mobile home parks. And that’s our model at Madison Investing is we basically want to do for other people better what we stumbled through ourselves.

Mark: Right. I have a question for you as someone who came from the tech world. What aspect of the real estate business do you think is most ripe for disruption?

Spencer: Oh gosh. This might sound squishing to some folks, but a little bit to me, it actually is a concrete kind of business process. The educational component is still the gap between how people communicate clearly on things that are financial concepts in the rest of the modern tech world. I used to largely work in FinTech. So, the way that they talk about money is clear. It doesn’t have industry jargon. It doesn’t scare people by having three words for the same damn thing, such as multifamily, general partners, sponsor, lead sponsor, operator. You can keep going down the list. It all means the same thing. And so ultimately, sometimes I look at this industry and I’m like, damn, you guys really did create this thing intentionally so that other people wouldn’t be able to come in and gobble up all the opportunities. Didn’t you?

Mark: The myth that it’s too complicated for you to do on your own.

Spencer: That’s exactly right. We were just chatting about this before we started recording Mark, but like hearing your story so far. It’s awesome. And I really feel like so many folks that are razor sharp, strong track record professionally does not in this business can jump in and do something meaningful that fundamentally improves their lives. And it doesn’t have to be active, it could be passive, it could be active, there could be more but the jargon scares the crap out of me. And I get it. I get why it’s intimidating. And no one likes to feel stupid. No one wants to ask the silly questions.

Mark: And plus, you’re taking risks. So, you don’t want to feel stupid and you’re also risking your own money. But I agree completely with you that I think real estate is fundamentally a very simple concept and you don’t have to be rocket science.

I walked into my first multifamily property knowing zero, not anything. It was just a broker said, you should be putting your money towards a mortgage. And I said I can’t have a mortgage. I’m in the entertainment business. I’m going to be out of work in a month probably. But then I said okay, “I do have some money saved up, put me into something that will help me survive this volatile business and I’ll do it”. And she pointed to a duplex and said, buy this.

Spencer: Yes. Good advice.

Mark: And I did. And I moved in and I had no idea what I was doing, but it’s simple. And it’s made it more complicated than it needs to be.

Spencer: Completely agree.

Mark: Another quick question off the top of my head. So, having grown up in a family where your father was a broker, do you think we’ll ever evolve into a world where we buy and sell properties digitally without the broker?

Spencer: Gosh. That is definitely one of the most debated questions amongst the tech companies that focus on real estate space where I think we’re always off. I’m sure the companies that are claiming that they’re going to solve this problem, don’t want to hear that. But I think we’re still a few years off. So look at many of the early players in these old industries, real estate is a great example of an old industry within real estate.

Sometimes people think mortgages and real estate are the same industry. So, mortgages there are big players. I won’t use names here out of respect for these companies, but they are really skilled at building huge businesses by front ending a tech process. And they say, come get a mortgage with us. It’s the click of a button. You go click that button, say, I’m a borrower I want to get a mortgage and they say it’s magic.

We’re going to come back and do your prequalification here, get your approval, all this other stuff. It’s not a tech solution. What it is, is a website that captures your information and then an army of very capable, talented, smart, paid by the hour humans based out in a lower cost area of the country that are still pushing paper, the way that a traditional mortgage has been created for the past few decades.

So, that’s the type of thing that I think there has been an explosion of in the past 5 to 10 to 15 years, particularly recently, where there are pieces of these old processes, these old industries that are starting to get moved truly to attack solving the problem in infrastructure. But most of it, just to say it bluntly is tech lipstick on a pig that is old school operations directly.

To answer your question in a very specific way. I don’t think the broker necessarily is going to go away. I do think the appetite of Gen Z and I am still fairly young enough to be an elder millennial and our generations are getting more open minded to doing that. But they want expertise of a person who is human. They’re not going to go through a phone tree to get advice on how to buy a house. They’re going to still going to want to go and talk to a human being. They still going to want to make sure they can get answered. They want to see a human face to face to be able to do that. We haven’t built a robot yet that can solve that.

Mark: There are still too much at stake for those.

Spencer: That’s right.

Mark: So, you got into real estate investing passively, and then you started purchasing some properties of your own. How did you make the transition into fundraising?

Spencer: So, what we do is we’re at co-sponsor and I’d help you. For the savvy folks out there in the business, what we do as an LP plus code GP model, now that I threw two acronyms at you, let me explain what they mean. That means we are passive investors, and that’s how we started. We still passively invest in all of our own deals now. Alongside folks that we have encountered in our own network they want to reach out to us, if they don’t have time to vet these deals themselves. They don’t have the expertise to develop these real estate’s themselves. They do have the capital but they’re looking for a really strong investor. So, what we did was we realized, wow, we can add value personally here, because I have essentially, 13-year operations in sales and even some real estate background.

So, I think that there’s a business there, not sure what it is yet. I believe in coaching; I did a lot of coaching myself in my corporate career. It’s like one of the biggest joys of my life is ramping up and hiring hundreds of people and coaching them as leaders and professionals. I’m willing to pay for it. And so, I did. I think I just signed up my fourth real estate specific coaching program just this year. And I’m probably always going to be in one of them, but that’s how we originally started. It was realizing, Oh, there’s a need to be solved here. It’s a good time for me to potentially just pivot out of my day job anyways, we’ve gotten good cushion on our financial situation.

And I’m going to go full time into this real estate thing, because I genuinely believe more people should have access to these types of investments. And the only reason they don’t is because of this story that we all grew up with, which is crazy Uncle Bob at the dinner table at Thanksgiving table said, “Oh, I lost my shirt in that real estate deal 30 years ago.” And that’s typically what scared people off from doing any real estate investing for the rest of their lives. So, how do we bridge that gap and get all of these folks in my network that need a better solution for their financial outcomes and long-term retirement lifestyle, whatever they need to solve that problem. So, we started transacting on deals on both sides of those deals a few years ago. And now we’re on our, I think our 18th deal as Madison Investment right now.

Mark: Oh great. That’s nice. And I think you mentioned before we started that part of the reason was the environment that you were in. You were in the tech business, surrounded by a lot of people with money and you were in San Francisco, a market where there weren’t a lot of cash flow deals. You had more access to the funds than you did to great deals.

Spencer: Spot on. I appreciate you mentioning that. The quote that I shared with Mark before the show, and I’ll just share it bluntly with you guys right now is I was originally mismatched on my strategy and I was wanting to go at the time I was looking at a coaching program. I was getting prepared to pay.

The problem was if you want to be the boots on the ground, you want to be that real estate magnet. If you want to own thousands of units, you need to have someone who’s still going to be in the guts of that deal, literally available in that market to do it right. And so, I got the feedback from a mentor of mine. I told him the plan and he said, Spence, you got to take stock of your geography. You live in a money state you don’t live in a deal state.

So now is when all the California investors, they’d flood me with messages in my inbox, but I’ll just say that, hey, we still own a property here too. We still live here in California through and through, but that mental is right. And so, what we did was we built a co-sponsorship business and it’s not just the fundraising. It’s also a handful of other things that we do. And so, taking a strategy matters, man. I’m like, we were not planning on moving back to Colorado. We were not planning on moving our lives and uprooting our kids from great schools and a bunch of neighbors and neighborhood that we love. So, we had to figure out a strategy that works.

Mark: I love that. And I love that advice that you got you’re in a money state, not a deal state.

Spencer: It’s kind of harsh.

Mark: Very good. Very good. Who do you partner with? When you’re raising funds, do you dabble with different operators or sponsors?

Spencer: Yes. I’ve come to find out we do things quite differently than a lot of the folks. Because there’ve been a bit of an explosion of folks that seem to be interested in doing this type of work. And so, like I would say that I come from such deep operations and even compliance heavy background that I’m a very big process nerd. And so, what I get value on, I’m used to lending home as a lender. So, what I learned about working in the guts of a lender that makes 600 roughly transaction decisions every month is you learn things like underwriting. But on the residential side, you learn things about what it means to define a credit box.

What that basically means is how do you make a risk-based decision and put numbers to that risk-based decision? And before I lose people with their eyes glazed over, this is basically what I think is the single most important topic. I’m going to say the best thing that a lot of people tend to miss, which is you look at the team, the market and the deal and say, I didn’t come up with that. This is the three-part framework that very smart people out there came up with about how to analyze real estate. And should you invest in it or should you buy it? And the way that we look at it differently is the sponsor or the team that we partner with.

We joined them at the GB and we take on a handful of responsibilities because we become one big entity together, taking down this deal and also investing alongside of thousands or hundreds of other people depending on the projects. So, we have a short list of people we work with. And the sponsors we work with, not only are people we know very well on a personal basis, literally we finally added just a couple more sponsors to our very short list of roughly half a dozen.

And that’s after many meetings, many calls and my very personal relationship and even further than that paying for an expensive investigative background check on that person, telling them I’m going to do it ahead of time. And they say, we got nothing to hide. So, go ahead. That’s the kind of stuff that really no one else is doing.

Mark: I think that’s important.

Spencer: It’s critically important. Trust, but verify is just great advice. I’m inherently trusting, but everyone starts with an A. You got to put those processes in place. And we really take the time to vet the sponsors that we work with. And we put our own money first, before we actually ever bring a deal in front of our investors.

Mark: Now, if you’re enjoying the show, please do us an easy favour and hit the subscribe button. And if you liked the show, please give us a five-star review. As a listener I always wondered why podcast hosts are always begging me to subscribe and rate them. Well, now that I’m on the other side, I see why. It allows other listeners to find you. So here I go.

If you like the show, please subscribe and give us a five-star review. I like doing it. And more importantly, in an era of unprecedented hype over real estate investing, my goal is to be a truth teller. Real estate is not as easy as it’s made out to be, but you can do it. If you can get past the hype and get to the truth. My aim is for this show to help with that. Anyway, let’s get back to the show.

Mark: Do you focus on what they’re acquiring or what they’re sponsoring? Are there certain asset classes? I know multifamily is one of them or are there geographic locations that you favor?

Spencer: Yes, so we, for the past few years have been very multifamily focused. We have also for the last six months specifically, we had planned this strategic pivot and this is something that was Pre-COVID. We didn’t know the COVID was coming. No one knew COVID was coming. It’s not like a crystal ball. Just like everybody else gives their disclaimer. They don’t see a crystal ball. I do know the market was at its high. We had a ten-year amazing run the market cycles. If you study how the economy tends to work over the past 100 years, if you study how market cycles real estate work, you knew something’s going to happen.

Recessions don’t just come. They come because of a trigger event. The trigger event we didn’t know it was going to be COVID. I didn’t know it was going to be COVID-19. So, I didn’t plan to quit at five months before COVID and I certainly didn’t know that our planning before COVID we’re going to still do multifamily deals. We’re still going to invest in multifamily. But we also think there are couple asset classes that are particularly strong and even potentially, this is where we opened up the can of worms on debate for people that email me afterwards.

That is arguably maybe even more recession resistant as evidenced by data and numbers in the form of storage and mobile home parks. So, we still do multifamily. And we even just closed on a deal for multifamily. That was a really successful one through COVID just three weeks ago. So, all that being said, those are the asset classes we’re leaning into now.

Texas has been our primary focus. It still will continue to be our primary focus it’s largely around DFW Dallas, Fort Worth. We’ve also gone more recently last year or two into the Carolinas, love the Carolinas, particularly Raleigh area of North Carolina.

Mark: You touched upon it, but in the current market conditions, what are you doing? Are you doing anything different?

Spencer: Yes. I would just say that being more selective and saying no a lot more. We already did say no frequently. And when I say that, what I mean is we feel very fortunate that we’re in a position now where, up and coming sponsors and even established sponsors have been reaching out to say, “Hey, do you want to join us?” And so, thank you first and foremost, if you’re listening to this and you’re one of those sponsors, I appreciate it. It’s very much valued. I won’t say that. We’ve been saying no, because that’s one of the biggest learnings I ever got from my corporate career.

And when you’re trying to survive working 60, 88, 80, 100 hours a week and grow a business remarkably fast, you have to learn how to say no a lot, otherwise you get nothing done. And so, I applied that same ethos in our business and our investors expect that, but on the deal, front saying no, a whole bunch. We’re basically saying no a lot because people want to jump into things that are more development focused right now. We only focus on cash flow deals. Where you see cash flow and you want. That’s kind of the stuff we’re doing right now, Mark is really being thoughtful and consistent about our vetting processes and approaches and saying no a lot.

Mark: And are you vetting not only the sponsors. Are there sponsors that you have worked with in the past and you trust them as solid sponsors, but do you then go down to the deal to deal basis. And will you say yes for one deal with them and then say, no, this one just looks a little too shaky?

Spencer: Yeah, we do. And I think a lot of people are surprise when we tell them that, because some of these names on this list are not exactly small players. We’re talking about people that are fighting to get to a chance to work with that person. And we are telling that person, no. And that actually literally happened on a deal that was before COVID hit. And we said, no on that deal. And it’s not a bad deal. And then I want that to be abundantly clear just because we’re not an epic force over here saying, Oh, Madison didn’t pass judgment on this deal it’s a bad deal.

Not the case, any investor out there, you have your criteria. I respect that criteria it’s awesome that’s it. It just wasn’t a match for our criteria. And so, we passed on it and like so many other deals that are out there, it got restructured. Repost COVID better price solid enough looking deal for a lot of folks, but we ended up passing that deal. So, we do say no. And we say no a lot. And sometimes it’s a tough thing to navigate.

Mark: It’s interesting because real estate is such a relationship driven business. However, if you’re in your position, I would imagine when you get or looking at these deals and then maybe it’s a sponsor that you’ve done a dozen deals with your loyalty has to be to your investors, not to that sponsor.

Spencer: Exactly right. Every time.

Mark: What do you think the biggest myth or misperception being perpetuated in real estate is nowadays?

Spencer: How do I frame this without undermining the previous comments that we were making earlier about it? Because I want this to come because like everything else in life. I think Mark, our brains, crave, binary, simple playbooks. We love a playbook. We love a quick bite. We love short term gratification, quick fix. That’s just not the way success happens in life for any of us. It’s twists and turns and hardship.

It’s messy, perfect word. It’s messy. So real estate is messy. Do I believe in coaching programs and should you pay money for them? I was going to say a much more crass version of this, but I’ll just say, hell yes, you should. If you are serious about doing this stuff, and you’re going to work your ass off, go pay for a coaching program.

Don’t let it do the work for you. It’s not going to work and you’re not going to win. But at the same time, expect to fail a lot. And once you get there, just know, yes, real estate is accessible for anyone. Yes. You should pay for a coaching program. No, that doesn’t mean it’s going to be easy and no, it’s not going to be overnight. So, it’s interesting how people really need to wrestle with that and they need to understand, you can still get inspired and find that inspiration and find your why. If you’re in a day job, you hate. The thing I would frame to someone because this is the way so many of the coaching programs are out there.

So much of the real estate narrative that is played out there on the marketing talks goes, as they say, look at this beautiful life for this person that ends up getting into real estate investing. What they don’t tell you, is that it was really, really hard work and conviction to get there. And it takes sacrifice like meaningful, significant sacrifice. And is that sacrifice worth it? A hundred percent.

Mark: It’s slow.

Spencer: It’s slow

Mark: I think the perception is starting to be more widely grasp. It’s because of the pandemic and the recession. My concern a year ago was that the market is flooded with people that don’t seem to be grasping, that we go through downturns. That real estate Is cyclical and that this is going to end. This boom cycle is not going to charge forward indefinitely.

Spencer: Yes. There is risk.

Mark: Asset class, people were almost starting to just give up the notion that you can never lose money in real estate.

Spencer: People will get a lot of swagger when the market is unexplainably going up. And right now, it’s a little bit funny. And I think that people need to understand this is a long game. This is a big wealth game. This isn’t a go get a nice bump under index bond. This is a, I want the option to buy eight jets. I have no desire to buy one. I want to be a great dad and have no financial obligations because my lifestyle is paid for that’s the wealth that real estate gets you. It’s not the, Oh cool. I got a great wind to brag about to my friends on nights and weekends because my one investment in index bond happened to spike.

Mark: Sure, sure. Is there a trait you possess that serves you best both in real estate and in life?

Spencer: I am the most authentic. This is according to our investors. And according to people that I work with in the business, they say I’m the most authentic person that they’ve met in the real estate business. So, for what it’s worth, you can be the judge of that. I can’t put a pile on, I don’t do that well. So, I just found that the only way to be successful is to be myself fully. It was very hard for me to put on hair product and a collar shirt, but you’re worth it today, Mark. And so, I’m hiding my tattoos from my rock and roll days.

Mark: I know, I want to hear about that. I know we’re going to run out of time.

Spencer: We’re going to run out of time. But whenever people feel like they have to play a different role, put on a face, put on a mask, it tends not to go well over the long-term and people find out.

Mark: Is there a trait that you feel holds you back, that you need to work on?

Spencer: Oversharing. The other side of being overly authentic is you tend to overshare by oversharing I don’t mean like proprietary secrets, what I mean is just because I’m authentic, doesn’t mean other people are comfortable of me being around. And I never want to make someone else feel uncomfortable.

Mark: So, I usually wrap up with this question round. Let’s jump in.





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