Neil Patel

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Imagine a startup that doesn’t fit the usual mold—one that manages over $100B in assets with a team of nearly 600 employees. This is the incredible story of Matthew Fleissig and Pathstone, a company that has experienced tremendous growth and continues to innovate in the world of finance.

Pathstone has attracted funding from top-tier investors like Kelso & Company and Lovell Minnick Partners.

In this episode, you will learn:

  • Matthew Fleissig’s early passion for computers and entrepreneurial ventures set the foundation for his future success in finance and tech-driven solutions.
  • His experience in competitive tennis fostered a resilience and drive that he carried into his professional life, particularly in the challenging finance industry.
  • College was a crucial period where Fleissig engaged in IPO trading and software development, sparking his deep interest in finance.
  • Fleissig’s journey included diverse financial roles, from wholesaling mutual funds to comprehensive training at Goldman Sachs, which rounded out his expertise.
  • Pathstone was born from a vision to provide a full suite of financial services to ultra-high-net-worth families, driven by Fleissig’s diverse skill set and experience.
  • The firm’s unique model of offering unbundled, personalized services and solving clients’ diverse needs has been key to its rapid growth.
  • With a current $100B in assets under advisement, Pathstone aims to become a national brand, addressing the underserved ultra-high-net-worth market with innovative, technology-driven solutions.



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About Matthew Fleissig:

Matthew Fleissig is a Co-Founder and served as Chief Executive Officer at Pathstone Federal Street. He is also a partner of the firm and a voting member of the firm’s Investment Committee. He also serves on the firm’s Executive Committee and Board of Managers.

Prior to his role as President, Matthew served as a Managing Director at Pathstone Family Office. Prior experiences include the role of Principal for Harris myCFO Investment Advisory Services and a Financial Planner at The Ayco Company, A Goldman Sachs Company.

Matt was a member of Harris Bank’s Outside Advisor Review Committee, a select group of 12 senior investment professionals, which directed manager due diligence, search and selection for the bank’s $60 billion platforms.

He was also a member of Harris Bank’s Investment Management Committee, where policies for asset allocation, alternative investments, equity and fixed income managers and compliance are decided at the firm level.

At Ayco, Matt provided comprehensive financial counseling to Fortune 500 executives and high-net-worth individuals. Clients were advised on investment opportunities, complex tax issues, estate planning and benefits and compensation decisions.

Matt earned a Bachelor of Arts in Economics from Muhlenberg College in Allentown, PA and obtained an MBA in Finance from Fairleigh Dickinson University in Madison, NJ.

Matt also holds the CIMA® (Certified Investment Management Analyst) designation and is a member of the Investment Management Consultants Association.

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Connect with Matthew Fleissig:

Read the Full Transcription of the Interview:

Alejandro Cremades: All right. Hello, everyone, and welcome to The Deal Maker Show. so Today, we have a really amazing founder you know that they you know we’re going to be learning a lot. and they Again, you know like the whole stuff that we like to hear, the building, scaling, financing, all of that good stuff, ah but also you know like their their business. i mean it’s It’s not the type of startup that we hear. It’s pretty amazing. you know They’re managing over 100 billion, 600 employees, you know tremendous growth that they have experienced too over the past years, and they it’s going to be super inspiring, the conversation that we have ahead of us. So without further ado, I’d like to welcome our guest today, Matthew Fleissig: hew Flasek. Welcome up to the show.

Matthew Fleissig: Thank you, Alejandro. Thank you so much for having us.

Alejandro Cremades: So originally growing up there in Jersey, how was life growing up? You know, tell us tell us about yourself. how was how How was life? Give us a walk through memory lane.

Matthew Fleissig: North Jersey, I don’t think you can make that interesting at the end of the day. yeah Some people will call it a communist state as we yeah as we sit here. but But ah life was good, grew up playing tennis, ah ah probably playing way too much with computers at the same time and computer science. And, ah you know, yeah dad was a lawyer, mom was an occupational therapist. And I will say, ah you know, my dad to this day, 72 years old, ah still a real estate lawyer and one of one of those real lawyers that like really liked the law.

Matthew Fleissig: So ah always really aspired to be like him ah growing up and showed the same work ethic ah that he had. But ah life was good, tennis was good, Livingston tennis was always a top 20 in the state, and we always got beat by Newark Academy. Not that that still bothers me to this day.

Alejandro Cremades: So, so how would you say that the competitiveness, you know, in your spirit, I mean, obviously playing tennis, playing tennis in college too, how do you think that has impacted you as well as a founder, you know, as a professional?

Matthew Fleissig: Yeah, well, I mean, I’ll just say what we see and in no different when we’re hiring people, ah folks who played competitive sports ah gives you a little bit of an edge. And ah you know it was always fun in a competitive nature. And especially in ah in ah in a North Jersey town where you had top tennis players and then playing tennis in college, ah it was you know I’ll just say it was definitely a part of the fun is you were ah as you were growing up. I’d say on top of that, though, is also a mixed tennis, but trying to find entrepreneurial things of ways to make money. ah Getting a job was fun. But, ah you know, in the early days of ah I’ll say the Internet and eBay and others, you know, I say I really try and mix that ah with with finding interesting ways, ah ah you know, the early days of the Internet to find ways to make money at the same time playing tennis and being competitive.

Alejandro Cremades: So out of all things, you know you you talked about computers and then also you know you ended up going into finance. Why why finance you know instead of maybe like law school? Because obviously you ended up like you landed in New York City and and you went and added in the finance space you know versus anything else. Why?

Matthew Fleissig: Well, now I feel like Alejandro can have me start telling some secrets, but ah ah in college, it was also the dawn of IPOs and in the late 90s. And if anyone remembers, E-Trade was offering IPOs for every account that you had. And I ended up writing a bunch of software to auto-confirm IPO trading and various other things. It might have hurt my ah performance freshman year of college a little bit ah ah from doing that.

Alejandro Cremades: You

Matthew Fleissig: But I’ll say I learned an unbelievable amount in a short period of time. ah My favorite part of that is that every dollar I made, I i spent some and had some fun. Don’t get me wrong. But I invested it all in ah in stocks that, ah if if anyone remembers, Lucent and Cisco. ah They went up and then they went back down. So ah however money much money I made, I learned every lesson ah from that, from losing it all, going back to about the same money I started. And I’d say that was really my entrance into the finance world ah that I had a passion and a love for.

Alejandro Cremades: So then you moved to New York City after college and then you um yeah you were basically working as a wholesaler calling on brokers for mutual funds. You know, I guess what was the experience like of of calling, putting yourself out there? How was that for you?

Matthew Fleissig: Well first is you have to remember if I was a computer guy what I what I really did and and coming out of college in the early 2000s after the bubble burst there weren’t a lot of jobs and I was lucky enough ah to ah to meet some folks at Lord Abbott. ah who are still in ah Jersey City to this day. And it was the most out of the comfort zone a job that I possibly could have taken. um You know, I was debating at the time whether, you know, do you look for a job that we’re in a computer science, ah where you’re, you know, I’m gonna say no windows in a back room and not talking to people, or doing something like this, which was an opening that I thought was gonna really, you know, expand what I was looking to do.

Matthew Fleissig: And I’ll tell you, you know, calling brokers throughout the country um and getting hung up on over and over again, at the same time, the firm kind of rated you on how many calls you could make and how long you could be on the phone. um It was amazing. The training program. ah It was literally four to five months of training, of storytelling, presentation skills, ah you name it. And it was just this unbelievable experience. ah And I’ll just say it gave me confidence that has stayed with me in training for my entire career and my entire life. So did something way out of my comfort zone. I felt like it really paid off and it and it really ah opened the door to the world of finance to me as my ah career went on.

Alejandro Cremades: So then eventually you landed at Goldman Sachs and that was you know really the pivotal moment for you because you had that exposure to the world of family offices as well. So how was that the immediate step for you to to to really get going with Pathstone? How was that?

Matthew Fleissig: Yeah, I mean, I will tell you, so there’s a division of Goldman Sachs called ACO. The culture, and I think this is again, you had this incredible training at Lord Abbott. ah At ACO, ah you were you did taxes, you did accounting, you did investments. The whole business was working with working with Fortune 500 CEOs and and the Goldman Sachs partners. And they had things like ACO University, where they would send you away and you would learn about estate planning. and It really rounded out, I’ll say, the experience that I had from the straight investment, wholesaling side, investment side to a much more holistic business plan. And what you saw is that, you know, this was, again, in the early 2000s, there was a real need for this. And there really were not other firms out there that offered, um you know, your full suite of services more than just direct investments.

Matthew Fleissig: And the culture part really left another lasting impression on me of just how much training was done to grow their people in-house and make you smarter and better advisors to be able to work with with more and more clients. So those two experiences you know now having, I’ll say, a computer science, a ah investing background, and now an accounting, tax, estate planning, ah really rounded out a skill set as we continue to push forward, I’ll say, in life.

Alejandro Cremades: So how did you meet Steve? Because that was a very important you know thing in your in your path.

Matthew Fleissig: Yeah, I mean, i we were a pathstone today, which is again, started about 17 years ago, 18 years ago. I randomly met this incredible entrepreneurial family named the Braverman family and and Steve Braverman, and his family invented the powder-free latex glove ah during the age crisis. And the most amazing part about Steve and his family is that that was not actually the liquidity event. um That was actually the third time that ah that Steve’s dad, I’ll say, retired and is still working today at 86 years of age as as a deal guy. And it’s just an incredible thing to say. But I was lucky enough to randomly meet him where our families had a ah ah cabin in the Catskills. And I’ll never forget when I met Steve at a barbecue and he said to me, hey, can you do asset allocation?

Matthew Fleissig: I was like, yes, Steve, I i could do asset allocation. He’s like, you want to come in on Monday and talk. And that was the start of it. He had this vision um around services, ah where families and specifically his family was looking for a solution. He had the investments covered as being a financial engineer and running his family’s single family office for years. But the idea was is you know all these other services that are hard to find ah for ultra high net worth families, all the tax, the accounting, the bill pay, et cetera.

Matthew Fleissig: Steve’s family sold the rubber glove business for safe skin to Kimberly Clark um in 1998 for a billion four. And, ah you know, families of that size and single family offices have trouble finding ah the right capabilities or software. And that was the business model was ah how do we create a ah single family office ah for multiple families?

Alejandro Cremades: So then obviously, path stone is born and the rest is history. So at what point did it become clear that the that it was time to to get going with path stone? ah was that day

Matthew Fleissig: Well, we originally were together at a bank. ah We quickly realized that it didn’t make sense, ah the business we were doing inside of a bank. And so after the financial crisis in 2008, a group of us got together, there were seven original ah shareholders, and we formed PathZone in 2010. We had ah the most amazing part. We had 19 people, 19 prominent American families, I would say, about a billion, four in assets. and ah And we went on our way. And the most amazing part is this business model as we launched it, ah it ah it just took off. ah We effectively tripled in and four years.

Matthew Fleissig: It was a wild time. We were building the house while we were living in it. There was no technology, so we wrote our own optimizers. We wrote our own rebalancers. ah We helped design our own reporting systems. ah It was just a wild, awesome time that you know I was sitting there saying to myself, you know wow, all the everything I had in my past, from the ah computer science and programming to the estate planning ah to the tax, et cetera, you’re getting to use all of it.

Alejandro Cremades: you

Matthew Fleissig: And we got to a pivotal point pretty quickly where we grew to 4 billion um with about 50 families. So families were slightly under $100 million dollars and average net worth. And ah that we quickly realized that we weren’t going to be able to keep this pace ah without scaling in a different manner. And we met with ah two pretty important investment bankers ah that I’ll say changed the direction of PathZone forever. And they came to us and they’re like, you know you need some more adults in the room.

Alejandro Cremades: you

Matthew Fleissig: You need more capabilities. You need scale. um You need to take on and out outside capital and ah and find a firm to merge with. And so ah we took on outside capital in 2014. We took on convertible debt. And ah I’ll say that team there gave me an MBA in ah M and&A, which I’m internally grateful for and thankful. And we went on a national search and acquired our first firm in Boston. It was another $4 billion dollars firm in 2015. And all of a sudden we are in the outside capital and M and&A game, which ah I can’t tell you that was part of the original business plan.

Matthew Fleissig: And all of a sudden, we’re an $8 billion dollar firm. There was another firm of friends of ours that got ah they had some issues. ah So all of a sudden, we we had another office in l LA and another office in DC, and we’re 10 billion. ah We grew it to 16 billion in ah over the next couple of years, all organic. So from 2015 to 2019, we quadrupled. and ah and And it was just part of the story. And all of a sudden, we we realized that ah this wasn’t just going to be a club or I’ll call it a cult ah for a very select group of families, that there was a blue ocean opportunity in a un completely underserved market ah for the ultra high net worth.

Matthew Fleissig: And so

Alejandro Cremades: So I guess for the people that are listening to to to get it, what ended up being the business model of past of Pathstone? How do you guys make money?

Matthew Fleissig: ah We are a completely unbundled business ah around services and investments. So anything that you can dream of on the investment side to reporting to admin, ah we buy planes, we hire pilots, we background check the dog walker, we’ll do the payroll for the household staff, we’ll collect your mail from five homes. um I like to say we don’t say no for a living. And it’s offered in a completely unbundled manner, very different from the world of the of the banks and the broker dealers.

Alejandro Cremades: you

Matthew Fleissig: um and And that’s where effectively we actually charge separately for what you consume versus trying to charge a percentage percentage of your assets and kind of hoping that someone doesn’t use those services ah because it reduces their margin.

Alejandro Cremades: And it sounds like you guys have been using M and&A to ah to grow faster. I mean, and like you were alluding to it. I guess you know one question that hits me here is that 99% of acquisitions you know fail because of the integration, right? The integration is the toughest part.

Matthew Fleissig: Yeah.

Alejandro Cremades: So how do you guys go about acquiring service-based business where it’s all about the people? How do you go about making sure that these people are going to stay in on the long run?

Matthew Fleissig: So first of all, I love the question because I’d say the other big differentiator from us on the acquisition side is that we fully integrate. And the learning probably started in Boston where I pretty much moved to Boston for a year as we got together. As you know, with PathZone, we don’t have a product to sell. We don’t have any widgets. it’s ah it’s we give We give advice. ah you know In our world of of AI and people thinking of chatbots, You know, families still want to be advised by other people. on So we have a very robust equity program that’s been another big piece of the outside investment in private equity world that I feel like just doesn’t get the right justice. ah Sometimes here, hear private equity or VC, and they think it’s like some kind of, ah ah you know, evil thing that’s coming in and stripped to something for parts. It’s quite the opposite. um So when we take on a firm, a couple of things. One, we we try and equitize the next generation.

Matthew Fleissig: So if our we’ll have close to 600 people ah by the end of the year at Patstone. Almost half are shareholders. And so when you live in a world that you know, and we’ve now had three rounds of private equity come through Patstone, we know that every four to six years we’re going to have a transaction. The shareholders who are here here, yes, they make great cash comp. Don’t get me wrong, but they also build net worth with a lot of these incentive unit programs that we create ah with the private equity firms as part of the transaction. So all of a sudden, ah you know folks every four to six years kind of have little mini transactions that they never would have had if we would not have an outside provider. And we know that every four to six years, we’ll keep stair stepping up to larger size private equity firms for the foreseeable future.

Alejandro Cremades: So then, so then how does the, um, I mean, that’s amazing, you know, like, so how do you guys go about then identifying some of those? Because I mean, you’ve done, uh, you’ve looked at horizontal deals, also vertical deals.

Matthew Fleissig: Yeah.

Alejandro Cremades: So how how how do you go about one another and then also how do you go about executing on it?

Matthew Fleissig: So first, everything is culture. And so we’ve done 14 deals in 12 years. ah So it’s it’s very targeted in focus of when we do a deal. Historically, up until about two years ago, we were mainly focused on acquiring other RIAs ah who fit our culture and people. I will tell you, ah we have met ah some some you know i’ll say good businesses, but people who won’t mix. Or sometimes you go and you have the social activity and it’s something very important. We do going out to dinner going out with the people that you’re going to meet. You quickly realize who they are and what they’re going to be like and are we perfect. No, are we have we been close to it. Yes. I mean, there’s still this reality of trusting your gut ah knowing the culture and knowing the people and what are your

Matthew Fleissig: you know What are the things you accept and don’t accept? And what is the business model ah that may be out there? But we’ve done a very, very good job of building a strong team, building a large equity base. And what we started to realize is that the firm grew is, holy cow, if we’re claiming we’re this multi-generational firm for multi-generational clients, we’re missing things. um The other piece of it is, is every time you make a referral out to a law firm, to an accounting firm, to ah to an aircraft firm, a travel firm, you’re effectively taking a risk with your relationship with those clients because you can’t control the experience any longer.

Matthew Fleissig: And so part of this journey has been this obsession of insourcing.

Alejandro Cremades: you

Matthew Fleissig: And we don’t release things until it’s at, a I’ll call it the pathstone level. And so ah we acquired a trust company two years ago. That was a big gap in our business um ah to be multi-generational. Another big piece of it on the automation side was how do we manage portfolios on an after-tax basis in an incredibly efficient manner. And ah we ah combined with a firm in Walnut Creek ah that is effectively, I’ll call it an AI automation portfolio implementation technology that ah tax loss harvests portfolios on a daily basis. So some pretty advanced things. And right now we’re looking ah

Matthew Fleissig: on the property and casualty insurance side. We’re looking on this um the cybersecurity division side of ah what our clients face when things like that come up. We’re looking potentially to acquire a law firm and bring that in-house. How do we really like perfect the client experience ah and and not take on that risk every time we see it of an outside party?

Alejandro Cremades: That’s incredible. Now, obviously, you know for your guest’s operation, you’ve seen it all. I mean, not only you are a helping you know with the investments of of those families, but then also helping them with anything that they need. I mean, you’re in the business of not saying no when they ask you for something.

Matthew Fleissig: yeah

Alejandro Cremades: So what what what are some of the crazy, crazy things that they that you guys have done for some of your families?

Matthew Fleissig: Well, ah first, yes, we’re in the business, we don’t say no for a living, but ah I will say we also we solve problems. And, and our job is to be that first phone call. ah And I’ll say it’s really an interesting part of the of the client journey and you see it is, is that first time you get that phone call, where someone’s asking you for something that’s not about investments or tax, that’s when you know that you’ve really become part of the family. And that’s what we try and do. But you’re right. We’ve, ah we’ve seen a lot of interesting things. I’ll tell you a couple weeks ago, we were a tough touch situation. um We, we had a client who’s, whose parent fell ill, and they thought there was going to die in a different part of the United States. And, ah you know, you get the call, we’re 24 seven. I mean, I think that’s part of the bargain of what happens. But ah

Matthew Fleissig: got a call over the weekend and they said, Matthew Fleissig: , I think my mother’s dying. um you know How fast can you get me to ah to New York? ah We had a plane on the tarmac in 90 minutes. ah But yes, I’ll tell you, we have delivered goats. We delivered a lot of gold.

Alejandro Cremades: you

Matthew Fleissig: um We’ve done mock trials from when someone was ah in a lawsuit to get them prepared and we hired the marketing. people and we hire jurors and prosecutors. um So you know we’ve we’ve purchased engagement rings ah for clients and their children. I’d say there’s a lot of neat things that we do and it’s and it’s a really important part of becoming close to the families and it’s just it’s just it’s just what we do but we what we do for a living.

Alejandro Cremades: that’s amazing Now, I guess for the people that are listening to get a good understanding on the scope and size of the operation, what can you share with us?

Matthew Fleissig: Yeah, no, ah we have, ah like I said, almost 600 people towards the end of the year. we If you look at the business, it’s organized into a trust company, a technology company, and the family office. um The assets are about two thirds in the and the family office and about a third in in the trust company. I think the really interesting part about PathZone as you go into that is the trust company is a non-depository trust company. very similar, very different than a JP Morgan or Goldman Sachs where they have to hold the assets and be the trustee. This allows this unique flexibility ah for the firm as we sit here today where you know we can administer and be the trustee and not actually control the assets. So it really opens the door ah for different types of families and services ah that we hear.

Matthew Fleissig: The other big piece, I’ll say, on the on the data side is technology. um There is absolutely no technology in the family office space. You could buy a package of software here and there, um but we’ve spent the last, I’ll say, five or almost seven years building something called Arrow, ah which is accounting, reporting, rebalancing, optimization, and workflow. ah and and basically making data as the new oil for the system. So we’ve a centralized data warehouse, a front end on top, connects to the investment custodians, it connects to tax, it connects to accounting, ah and all the users work through that at our firm. and And when we sit here and you look at this and you need it, because I don’t think the market’s big enough for somebody to actually make this software. So when you meet other families and family offices, they’re literally sitting in Microsoft Excel and it would would blow your mind.

Alejandro Cremades: So then imagine if you were to go to sleep tonight Matthew Fleissig: and you wake up in a world where the vision of pathstone is fully realized.

Matthew Fleissig: Heh.

Alejandro Cremades: What does that world look like?

Matthew Fleissig: As you sit here today, PathZone is $100 billion, but you realize that’s that’s tiny. And you know you look at Goldman Sachs, it’s $6 or $7 trillion. dollars ah It’s a tiny firm. The other thing on the numbers is ah today, PathZone has about 700 families that average north of $100 million. dollars ah But you look in the market, ah the last study I saw is that there’s now about 230,000 families in the US with north of $30 million. dollars And so you sit there and you say to yourself, ah we have zero market share.

Matthew Fleissig: And so as we move forward, I think there’s this unbelievable blue ocean where the where the market for the ultra high net worth is completely underserved. There is no national brand ah in the fiduciary space and an independent firm that’s out there. And so I sit here and I said to myself ah that ah we have a chance to become the national brand and create a firm that does not yet exist. And we’ve had success. And you know yes, are we almost 100 times bigger than when we started the firm? Is that exciting? Yes. ah Have we 4 and 5x’d each time we’ve had ah investors come into PathStone? Yes. But we’re still on the first or second ending of this thing. And I think the interesting part is is that ah as we sit here, I don’t know what the dollar amount is. And you know if PathStone continues to grow, i don’t I’m going to throw out a number like a trillion dollars.

Matthew Fleissig: You know, is it that there’s a couple firms ah like a Patstone that equal trillion that starts to disrupt the bank and the broker dealer model? Or is it Patstone having to get that size? But I sit here, we’re in the first or second inning of this thing. um It’s an exciting time. And, ah you know, I don’t think there’s a I don’t think there’s an end game yet to to start pointing to or to pick a number.

Alejandro Cremades: So I mean, incredible journey now. You know you guys have been at this now on your way to two decades, right? you You’ve already passed the decade.

Matthew Fleissig: Yeah.

Alejandro Cremades: You’re on your way to two decades. Now, I guess on the on that front, you know if if I was to put you into a time machine, And I bring you back, let’s say, to that moment where you’re sitting you know in front of your computer you know after having met Steve and wondering, maybe you know it might make sense to give your notice and and and do something you know with Steve. and And let’s say you’re able to just show up right there in front of that younger self, and you’re able to give that younger Matthew Fleissig: one piece of advice before launching a business. What would that be and why you what you know now?

Matthew Fleissig: i I would have pushed myself to make us leave the bank and start the business sooner. ah The entrepreneur, there’s nothing more fun. This is an adrenaline rush. I don’t think there’s any other way ah to describe it. and and And to bring it back to computers, I’m not going to say that Patzones likes the video game SimCity, where you’re building something. But truly building something, there’s nothing more satisfying. And and doing this with with partners and changing people’s lives ah you know, around you as you build the business and spreading equity out throughout the entirety of the firm. I think those are just things that have been incredible success. But ah I would just say if I could go back ah in time, maybe we would have started the business ah a couple years sooner than being inside of the bank. ah But ah but no regrets. And it’s just, ah you know, very thankful and blessed from where we are today and look forward to where we take it in the future.

Alejandro Cremades: So, for the people that are listening,

Matthew Fleissig: I would love to reach out and say hi. What is the best way for them to do so?

Matthew Fleissig: our website,, p-a-t-h-s-t-o-n-e, and ah ah feel free to take a look and click the contact button and ah reach out. And one thing i’ll you’ll notice, and you’re welcome to test it, is ah if you fill that out, you’ll get a phone call with, ah i’d say I’ll say within 10 minutes, but I’d like it to be less than five minutes. Even if you do it at night, you’re welcome to test it out and see if ah see if that actually works.

Alejandro Cremades: I love it. Well, hey Matthew Fleissig: , thank you so much for being on The Deal Maker Show today. It has been an absolute honor to have you with us.

Matthew Fleissig: Thank you, Alondra. It was fantastic. Thank you.


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