March 3, 2020

JF2009: Going From Single-Family Homes to Active Syndicator With Spencer Hilligoss


Spencer just recently went full-time real estate investor. He grew up with his parents both active in real estate and as a child didn’t find it as something he was interested in so he instead went into the world of Technology. During his journey in the Tech-Start-Up world, he landed in a real estate tech company and learned about real estate investing. He then started out in single-family houses and after about 6 investment properties decided it was to slow and started to research multifamily. 10 multifamily deals later he now has a successful real estate business with his wife as his business partner. 

Spencer Hilligoss Real Estate Background:

  • Co-founder of Madison Investing
  • Active syndicator, real estate investor, and executive leader
  • Retired from his technology career of 13 years, just 4 weeks ago to go full time in multifamily real estate
  • Has co-sponsored deals totaling more than 3000 units and $328 Million
  • Based in Alameda, CA
  • Say hi to him at
  • Best Ever Book:

Best Ever Tweet:

“Set a clear goal with specificity, because taking action is critical, but don’t take stupid action. Stupid action just means, your aiming at something and you haven’t even set the goal yet. Go slow to go fast. ” – Spencer Hilligoss


Joe Fairless: Best Ever listeners, how are you doing? Welcome to the best real estate investing advice ever show. I’m Joe Fairless, this is the world’s longest-running daily real estate investing podcast, where we only talk about the best advice ever, we don’t get into any of that fluffy stuff. With us today, Spencer Hillgoss. How are you doing, Spencer?

Spencer Hillgoss: Doing great, Joe. Really an honor to be here, thanks so much for having me.

Joe Fairless: Well, I am glad, and I am looking forward to our conversation. A little bit about Spencer – he’s the cofounder of Madison Investing, he’s an active syndicator, a real estate investor, and executive leader. Retired from his technology career of 13 years just four weeks ago to go full-time in multifamily real estate. Has co-sponsored deals totaling more than 3,000 units in 328 million dollars. Based in Almeda, California. With that being said, do you  wanna give the Best Ever listeners a little bit more about your background and your current focus?

Spencer Hillgoss: Yeah, happy to, Joe, and thanks again for having me. I live out in the Bay Area, California. For those folks that are not familiar with Alameda, it’s this little island that is totally awesome, couched right between Oakland and San Francisco. I was born and raised here, but outside of moving around the country a couple times, this is where I have done most of my career growth.

I started in a real estate family; my dad was a broker. One of the top residential real estate brokers in the country, actually, back in the ’90s; we can talk more about that if the conversation takes us later… But I didn’t go down that path. I really ran away from that after  seeing what that entailed, and it forced me to run all these open houses when I was a teenager, and that didn’t leave a great taste in my mouth… So I ran into the local business. The local business here in Silicon Valley is technology. That is how I ended up going into this really fast-track journey, starting with the big corporate tech track of getting thrust into leading large teams of over 200 people at the age of 26 years old; way in over my head at the time, in hindsight.

Great learnings, a lot of scars that I look back on now fondly… But five software companies later I came to realize that there’s this wealth strategy that I was very subconsciously or unconsciously easing into… And I noticed everyone around me was doing this too, and it really just came down to this simple fact, Joe – people think that when they join tech companies out here, that they’re gonna get a meaningful share of that early-stage company equity… And they might be able to win that wonderful lottery that affords them a huge lottery, a huge liquidity event sometime in the future… And somehow that magical moment is going to give them a get-out-of-jail-free pass on all their prior sins financially.

So I finally woke up when I stumbled my way into a real estate tech company about four years ago… And I feel very fortunate to have done that, because a mentor kind of nudged me toward it, not knowing that it would end up being something to motivate me and educate me rapidly to pivot out of this technology career into multifamily, into syndication… Because that software company was very good to me, it was a rapid bootcamp if you will. I became a loan originator, I built a large team of loan originators; we did over 4 billion dollars in loans for fix and flip single-family homes.

We were doing 600 loans per month, so it was super-high volume… But I saw what flipping was, and I didn’t want anything to do with it. It was just a lot of work, the most active of active. So we really started off just passively investing and realizing “Wow, this is working well. This is a wealth strategy”, and over time we were drawn into many of the other appealing parts of multifamily. We’ve now built to the point where it’s not a side hustle anymore. After three years of building it up, it’s now become a thriving, growing business, and I’m just so humbled by the fact that people want to talk to us, want to work with us, and it’s a bless to wake up and talk about this stuff every day, and come on a podcast like this and talk to you, Joe.

Joe Fairless: You’ve said “we” a lot of times. Who’s “we”?

Spencer Hillgoss: We is my wife, my better half, and also business partner, Jennifer Morimoto.

Joe Fairless: Okay. With Jennifer, your business partner – is that your co-founder?

Spencer Hillgoss: She is my co-founder.

Joe Fairless: Okay. What do you all do, in terms of roles and responsibilities?

Spencer Hillgoss: Yeah, as you can imagine, I think that that was a little blurry when we started. I’d like to think that it’s just like building a clean, corporate business plan for a financial year… But it didn’t start that way. It was really a matter of aligning to strength. So if you had to align against core roles, I would say that Jennifer, my wife, is the digital marketing leader–

Joe Fairless: Oh, Jennifer is your wife… Okay, I thought there was two women involved here – a co-founder, Jennifer, plus your wife, someone else. But Jennifer is your wife plus your co-founder.

Spencer Hillgoss: Yes, sir. Yeah, exactly.

Joe Fairless: Okay, sorry. I wasn’t tracking. Okay.

Spencer Hillgoss: No, I explained it poorly. So Jennifer, my better half – she’s also my business partner. She’s a marketer by trade, so she has been doing that actually in the consumer packaged goods (CPG) industry for her whole career, and now she leads digital marketing for a pretty large company. So she does that stuff. She’s very strategic, and that’s her strength.

I bring in operations knowledge, I bring in business development and scaling. That’s really what I’ve done. We kind of carved the lines there, but I will say, we also tend to overlap on some of the analytics, on some of the back-office stuff, on some of the accounting with financial stuff, but we also lean on outsourcing, as one typically should. We use some relationships and partnerships for that stuff, as well.

Joe Fairless: What was the first deal  you all bought?

Spencer Hillgoss: Oh, man… I love talking about this one, because it was before we jumped to true multifamily. We bought a duplex; it’s local in California. It was way too much money for the cashflow it generated, and this was a great learning around how to set better goals… So we bought a $430,000 duplex… Because we live in the Bay Area. For those that are in the Midwest and South – you’re gonna sit there with your jaw on the floor probably, because you’re going “Why the heck would you ever do that?” It’s gonna appreciate, it already has, and we’re thankful for that. It is positive-cash-flowing from day one, but if I could go back–

Joe Fairless: It was positive-cash-flowing day one?

Spencer Hillgoss: It was.

Joe Fairless: How much was it bringing in day one?

Spencer Hillgoss: 250.

Joe Fairless: 250… Dollars.

Spencer Hillgoss: Overall. Yeah, 250 bucks. So it’s an appreciation play, with just enough to cover the monthly. We look back at that as our get on base move, but you’d better believe in hindsight we could have done over again. We hadn’t gotten clarity on the fact that we wanted that passive income, we wanted that cashflow on a monthly basis… So we spent too much of our cash.

Joe Fairless: How much did you invest in that deal?

Spencer Hillgoss: Oh, man… We’re talking probably a little under 100k.

Joe Fairless: Okay. So about 20% to 25% down payment?

Spencer Hillgoss: Yup.

Joe Fairless: Okay. And what’s it worth now though? I’m sure there’s a positive side of that story there.

Spencer Hillgoss: Honestly, I haven’t slowed down enough to go back and price it again.

Joe Fairless: What year did you buy it?

Spencer Hillgoss: I think we got it back in 2016.

Joe Fairless: Oh, alright. Well…

Spencer Hillgoss: It wasn’t that long ago.

Joe Fairless: Alrighty. And is it still making about $250/month?

Spencer Hillgoss: Yeah, it’s one of the steadiest things we have.

Joe Fairless: $250/month on a $100,000 investment.

Spencer Hillgoss: Wooh!

Joe Fairless: [laughs]

Spencer Hillgoss: You feel brilliant after you look at those numbers…

Joe Fairless: What is that, a little over 3% return, I think?

Spencer Hillgoss: Glorious. It’s funny, because in hindsight — there was so much competition for it, too. And you look at the numbers now on how you analyze a very complex larger property, which is where we focus now, and I’m like “That was a function of not truly understanding yet what it means to solve for cashflow, and just targeting a monthly income number.” Once we got that clarity, we went down through the very logical stumbling blocks and path that people tend to go down. We went to the Midwest, we bought some turnkeys… And we did all that and we then realized “Hey, our property manager headaches that we had locally  – which we do have some – just because we buy them out of state with a more established  property manager, that doesn’t mean that they go away.”

We still had to occasionally get on the phone, and we still do now, because we didn’t sell our Midwest turnkeys… We end up still having to pick up the phone for an occasional issue. And I’m like “That is not passive.”

Ultimately now what we wanna do is try to invest as much as we can, both on the active and passive side, and be able to scale our time… Because we have two young kids, my wife still works a full-time W-2 job, so I’m the full-time one on our business… And we have to figure out a balance to still have a full life, and not spend all of our available time just doing stuff that is ticky-tacky administrative stuff for properties. Our big focus now is on multifamily.

Joe Fairless: Do you self-manage that duplex?

Spencer Hillgoss: Nope. We use a property manager.

Joe Fairless: Okay. So duplex, 2016 – that was your first investment. Then what?

Spencer Hillgoss: And then right after that we went out and bought some turnkeys… And I think I was literally sitting there — I think I was in the hospital with my wife, having our second kid, when I was trying to negotiate on one of the loans for these things… Because we did it all in such quick succession. We went out and bought some turnkeys with a local turnkey provider I ended up connecting with, and we were one of their first clients, which was a red flag initially for me… But I was kind of able to backchannel, confirm that they were reputable people, they operated with integrity… And we bought a handful of turnkeys. I think we got them in Kansas City.

Joe Fairless: You think you got them — do you not know what city you bought them in?

Spencer Hillgoss: Kansas City, Joe.

Joe Fairless: [laughs]

Spencer Hillgoss: Kansas City.

Joe Fairless: I was like, “You truly are passive.” [laughs] You’re like “They’re in the Midwest… I’m pretty sure they’re in a state close to Missouri or Kansas… I’m not exactly sure though.”

Spencer Hillgoss: As one of the true to form Californians would say. It’s not California, so… Yeah.

Joe Fairless: [laughs]

Spencer Hillgoss: I’m not that jaded, but… It’s in Kansas City, and we’ve got five turnkeys out there.

Joe Fairless: You’ve got five. In a row, or at one time?

Spencer Hillgoss: In a row.

Joe Fairless: In a row. Wow. Over what period of time did you buy five?

Spencer Hillgoss: Very tight. It was 4-5 months in total.

Joe Fairless: Okay. And how much down per property on average?

Spencer Hillgoss: This was a little bit more digestible than the 430k…

Joe Fairless: Sure.

Spencer Hillgoss: This was a range of 50k-60k total per property.

Joe Fairless: Okay.

Spencer Hillgoss: And we had — let’s see… I think it was something like 15k-17k per property.

Joe Fairless: Oh, 50k-60k all-in price, and then you were putting in about 17k of your own money per property.

Spencer Hillgoss: Yeah, exactly.

Joe Fairless: Okay, alright.

Spencer Hillgoss: Shockingly, we were able to get loans on these things… [laughs]

Joe Fairless: Right, yeah.

Spencer Hillgoss: So we took that opportunity. The rates were still good, so we ended up doing that, and they’re cash-flowing well to this day. They are C class, so when you go C class – you know, it took longer to stabilize for a couple of them. Three of the five stabilized very nicely out the gate; two of them – you just have those headaches of higher vacancy. You get a tenant placement and then something happens, and then you have to get another one in.

Joe Fairless: You live in the Bay Area… This is not the Bay Area, or this is not California, as your people over there would say… Why go with a local turnkey provider who does not have a track record when you have others in that area who have track records, given that you’re not anywhere close to where your homes will be?

Spencer Hillgoss: There’s probably a caveat necessary there. We connected with a locally-managed management team for this turnkey provider that’s based in the Bay Area; they themselves have a very deep track record of a turnkey business and a flipping business across multiple different Midwest and South geographies. So their footprint is actually pretty established. But they had connected and integrated an already established property management company that is based in that geography.

So they basically bought and brought in that established property management, and then they created this turnkey offering because they already had a lot of strength on the rehab front, because they were just such savvy flippers, and they realized there’s a huge opportunity to go and offer these turnkey properties… And they kind of hit it from an angle of offering the right housing to help those in need, and it was improving communities. We are very values-based folks and we care about that stuff. So that resonated with us, in addition to the financial returns, so that’s what drew us to him.

Joe Fairless: Okay. And about how much are you making per property with those five, every month?

Spencer Hillgoss: $250/property.

Joe Fairless: Okay. Alright.

Spencer Hillgoss: [laughs]

Joe Fairless: The numbers are more favorable in that case, yup. It’s about 17.6% return, assuming you’ve got 17k all-in, and you’re making $250. Alright, so 3% on the original duplex. Now you’ve shot up to about 17.5% cash-on-cash on these five… Life is good. You’ve got these five properties, plus the duplex, you learned what you don’t wanna do and what you wanna do… Why did you shift?

Spencer Hillgoss: I think it was primarily speed and time. As an avid listener of your podcast and others, you hear a lot about time compression, and we talk so much about that in goal-setting when I’m coaching other people, too… Because I went into this thinking “I’m gonna ‘retire’ in 15 years or 10 years from my tech career”, because we will have generated enough passive income to be able to do that confidently. We ran those numbers, and I didn’t like the outcome.

The “build a single-family empire” roadmap is one that just takes more time. Some people can go and hit it really hard, but after signing all those individual property docs and loan documents, property by property, you sit there and you just have to ask yourself, “Isn’t there a smarter way to do this?” On the time component, that was the first determinant – “How do we cut this in half, at a minimum?” How do we cut 15 years down to 7,5, or something like that?

So the second one was going to be the time to management, and  I realized we still do have to manage the manager, and we still do have to think about this stuff, and we’d get these emails from our C class property managers and they would say “Hey, just to let you know, we have this other issue coming up, and I was like “I don’t necessarily think that the frequency and the tiny administrative nature of some of these questions would be coming up quite as much.” [unintelligible [00:14:27].28] economies of scale thing when you go up to very large properties… So it was really those two motivators, Joe, in addition to the fact I started to dig deep into the tax benefits of the multifamily side and commercial real estate, and I realized depreciation still exists very much so in residential, but it’s not quite as heavy-hitting as in the multifamily stuff.

Joe Fairless: Okay. So what did you buy next?

Spencer Hillgoss: Next, we actually just started analyzing and looking at and beefing up my ability to go and analyze the multifamily projects. Even before that, the one comment I wanted to make was I signed up for a couple underwriting coaching programs, because I know very well how to analyze deals within residential, but I didn’t have that skillset yet.

Joe Fairless: Which one did you learn the most from?

Spencer Hillgoss: Which coaching program on underwriting?

Joe Fairless: Mm-hm.

Spencer Hillgoss: I think he deserves credit for putting that darn calculator together.

Joe Fairless: That’s why I asked. Yeah, whoever it is, they deserve credit.

Spencer Hillgoss: I think Michael Blank. Michael Blank’s SDA calculator – that thing is worth every penny. It’s a nice template to get in and just quickly get in to grind on deals… And you’re able to pull it up, really get your own criteria that you can set, and then you can get just nerdy. You can get super-nerdy, and go in and start — knowing what you don’t know, and then starting the real learning from there.

So it’s just worth mentioning that, because I don’t think it’s necessarily as — I think the learning from the first property, that duplex, and then the turnkey, really hit home for me. This is not something that I wanna rush on. I’d rather measure twice to cut; actually, maybe measure three or four times figuratively before you go and cut once, when it comes to making investments into multifamily.

Then we started to go and invest passively. One of the first ones — because when we first started, we were not accredited. We were barely, barely not there. Then we became accredited, so we had to go and find deals that were actually gonna meet our status. So we had to be more selective, we had to go and reach out for a bunch of different sponsors, and kind of try to find those deals that would allow us to invest.

Joe Fairless: How did you find sponsors to reach out to?

Spencer Hillgoss: It started just with bigger pockets. Hitting those forums is incredibly helpful. There’s so many people that are willing to give their time and their expertise, and if you just track the people that are adding value on there, usually you can ping them directly with a direct message, and that’s as simple as it is. And you say “Hey, I noticed that you’re adding all this really great education and coaching out here… Do you mind if I ask, do you guys do deals, and who do you accept into your list?” That was it. It was really just reaching out to people and trying to get on as many lists that would accept non-accredited investors as possible, and then being able to look at the deals.

But there was also an element, of course, of fellow students within the coaching programs that I used, and just hitting them up and actually just building a relationship with them, and then having that very organically become something that I feel very open and willing to share. Another person says “Hey, I’m putting this deal together. Do you wanna come invest?” and then taking it from there.

Joe Fairless: Okay. So how many deals do you passively invest in?

Spencer Hillgoss: Now we’ve done ten. So it’s gone to the point where the speed of analyzing them is so much better… Because as soon as you have a framework, like everything else in life… The lesson I got from my technology career was you put together a simple framework and over time  it allows you to move more quickly, whether that’s scaling a team from one person to a team of 50, or if that’s making  a decision about going to invest in a new piece of software for your business… But in this case it’s going to make an investment.

The whole framework that we all talk about all the time, an operator market deal  – that is something that is really abstract at a high-level, but I got really specific with in terms of frameworking that out… So now it just lives in the spreadsheet for me; even 60-70 questions that I have just on the operator. That helps me build confidence that we’re about to go make a good decision with our own capital before we move forward and do that.

I wanted to hone in on that decisioning process, because I think that’s something that a lot of people tend to bypass. It deserved my attention, and I’m so glad that I’ve got the scars from the residential stuff to really truly understand the value of putting that together.

Joe Fairless: 60-70 questions… How many of those are you actually asking the operator versus you’re able to find out through your own research, without having a Q&A session?

Spencer Hillgoss: It’s gotta be realistically probably 5 or 10 questions that you need to ask the operator verbally.

Joe Fairless: What are some of them?

Spencer Hillgoss: I would say the most compelling one that ends up driving the best discussions and the most revealing qualities about the operator’s track record is the thing around failure of response. Just a very new rebranding, but here’s what it means to me… Failure of response to me means — I’ve worked with plenty of entrepreneurs in the technology industry who start companies, and they either win big or they fail and they go down, burning in flames, in a very dramatic way.

In multifamily there’s a lot of new operators that are amazing. They don’t have exits yet, let’s say; maybe they’ve kicked off a bunch of different deals, they haven’t had a five-year exit on their syndications… And you wanna believe in them. You see their deal. So how do you figure out, “Do they have the grit?” So what I ask them is “Walk me through a time that you have failed utterly on a business initiative, or a project, or something that was your core focus professionally. What happened? How did you respond? What were the key stumbling blocks that actually caused you to slow down or stop altogether to fail, and how did you overcome that?” Because what I’m trying to tease out with that type of question is their failure of response. Because if they’re sitting there with my capital, that 50k, then I wanna know they’re holding the wheel of this figurative car. Are they going to get distressed? Are they going to have a steady hand under duress?

It’s just a discussion. And like any other framework, Joe, in life and in business, there’s a set of guidelines. I don’t sit there like “Oh, you hit my checkbox today, therefore we’re going to move forward with the deal.” It’s more a matter of just informing the whole picture and making a risk-informed decision on “Are they gonna have a common sense grit about them?”

Joe Fairless: If you can think back to when you’ve asked that question with the operators that you’ve invested with, tell us about the worst answer that you’ve got to that question.

Spencer Hillgoss: The worst answer is “I can’t think of one.”

Joe Fairless: Okay. You’ve gotten that answer?

Spencer Hillgoss: Yeah I’m paraphrasing, but essentially yes. It’s the answer basically saying “I always hit home runs, and I’m lucky to say that that’s never happened to me.” I just don’t buy that… [laughs] I just don’t buy that, because you get to the point where you’re sitting there in life, and unless you’re like 18 years old, and just out of college, and maybe you’re a prodigy – I don’t know, I can’t think of the right profile of the person or background that could actually say that and back it up… I can’t. Everyone goes through challenge in life, whether that’s personal or professional.

Similar with a job interview. I’ll give a new college grad a chance to tell me a story about a project that they did if they don’t have any job experience to speak to. So in life, if you’re talking to someone who’s over 30 or older, I’m sure they have something they can talk about that’s been hard for them.

I don’t wanna get too personal here, but if I didn’t have an example to speak to, what I would probably bring up on a personal level is the fact that I lost my younger brother to cancer when he was about 15 years old, and I watched my dad’s brokerage fail, and our family had to downsize completely. It was an extraordinarily challenging financial situation for my family, caused originally by the death of the brother. I was departing college when that happened, and I had to somehow figure out how to get in the right headspace to go support myself in the working world.

So people can get however creative they want when they wanna address a question like that, but the point is – you’re still investing with people, and if you’re gonna go put your money into a crowdfunding platform, you’re not necessarily gonna go and have the ability to always ask that question to a human… And that’s also why you can put in a lower minimum. It just depends – how do we, and how do you as an investor want to decide to work with people? What matters to you in building that trust.

Joe Fairless: Based on your experience, what’s your best real estate investing advice ever?

Spencer Hillgoss: Oh man, I knew I was gonna get that question when I came on here…

Joe Fairless: You said you listen to the show… I ask it pretty much every show.

Spencer Hillgoss: I know, it even has that cool sound right before it.

Joe Fairless: Yeah, yeah.

Spencer Hillgoss: I would say go slow to go fast. And what I mean by that is you should slow down and take as much weekend time as you need to set a clear goal, with specificity. Because taking action is critical, but don’t take stupid action. Stupid action just means you’re aiming at something and you haven’t even set the goal yet. So go slow to go fast is the best advice I can give you.

Joe Fairless: We’re gonna do a lightning round. Are you ready for the Best Ever Lightning Round?

Spencer Hillgoss: Yeah, hit me.

Joe Fairless: Alright. First, a quick word from our Best Ever partners.

Break: [00:22:54].17] to [00:23:20].27]

Joe Fairless: What deal have you lost money on?

Spencer Hillgoss: Well, I would say that first one. It was the 430k duplex wonder.

Joe Fairless: Have you lost money on that?

Spencer Hillgoss: In the short-term, right? Because you’re basically cash out of pocket. So it’s the closest thing that I can come to to losing money on a deal.

Joe Fairless: Best ever deal you’ve done?

Spencer Hillgoss: Oh, boy… I would say two deals ago. It was actually a co-sponsorship deal that we did, and we ended up growing rapidly in our group. It was a large apartment community and we were able to help dozens and dozens of people, more than we’d ever helped before, to get into that [unintelligible [00:23:47].27] and we were really proud of that.

Joe Fairless: Best ever way you like to give back to the community?

Spencer Hillgoss: Right now, my absolute favorite is just coaching on a pro bono basis on a weekly basis. We also give charitably financially, but I would say that the most fulfilling one is just coaching and mentoring people, because it’s something I’ve done for most of my corporate career, and it’s something that I get pinged often on these days. I don’t have a formal coaching program, but coaching people on a weekly basis is very fulfilling for me and I love doing it.

Joe Fairless: Best ever resource you use?

Spencer Hillgoss: I would have to say — this is pretty self-serving, but I would say your book, Joe. I promise I wasn’t paid by Joe to say this. Joe’s syndication book was one that I read cover to cover. When I first got into this stuff, I read two dozen different books, and Joe’s book basically combined six or seven different books of value into one, so… You’ve gotta give credit to Joe for writing that great book.

Joe Fairless: Glad to hear that. And what’s the best place the Best Ever listeners can get in touch with you?

Spencer Hillgoss: Just through our website, They can also reach out to me,

Joe Fairless: Thank you so much for talking to us about how you’ve gotten to this point, your thought process, lessons learned on that initial duplex, then you’ve got those five turnkey properties, and then you and your wife made the decision to focus on larger deals, and you talked about why, from cutting the goal in half timeframe, to just time management, dealing with the properties and then tax benefits.

And then I really liked — on the first one, one of the lessons that you mentioned is target a monthly income number prior to putting money into a property, because then that will influence what type of property that you purchase… It’s just about being intentional.

Then I loved the question about the failure response that you mentioned, “Walk me through a time where you have failed utterly. What happened, how did you respond?” If people can’t own up to their mistakes in the past, then they’re certainly not gonna own up to mistakes – well, most likely they won’t own up to mistakes in the future. No absolutes, I guess, but most likely. So it’s a good indication.

Thanks for sharing your insights. I hope you have a best ever day, and we’ll talk to you again soon.

Spencer Hillgoss: Thank you, Joe. It’s been a pleasure.

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