
Supply Chain Connections · 2026-06-23 · 24 min
Key moments - from our scoring
Substance score
47 / 100
Five dimensions, 20 points each
Margie Shapiro represents a third-generation customs brokerage leader who built her company's resilience on intentional culture rather than process alone. Starting from a family business founded in 1915, she discusses the deliberate choices that kept Shapiro competitive through COVID-era disruption - remote-first operations, proactive webinars, book clubs, and wine tastings that maintained team cohesion. The conversation reveals how she translates arcane customs regulations, Section 301 tariffs, and evolving AI governance questions for mid-sized importers and exporters who lack dedicated compliance resources. Shapiro emphasizes that tech modernization, though painful (replacing a beloved 2000-era platform during Liberation Day), was necessary to handle stacking tariffs and dynamic regulatory demands. For tech companies building supply chain solutions, she calls out the need to anticipate customer questions and stay current with regulatory bodies like the Consumer Product Safety Commission. Her biggest worry: the coming tariff regime - particularly Section 301 directed at 60 countries - will exhaust importers who must balance daily compliance complexity with business continuity. B2B operators in customs, forwarding, and supply chain tech will find practical insights on culture-driven hiring, managing boomerang employees, and communicating across technical and business audiences.
Margie deliberately creates connection opportunities through book groups, team channels, webinars, and online wine tastings. The key is being intentional rather than assuming remote workers will stay connected organically - culture requires proactive investment in shared experiences and ongoing dialogue.
Pay attention to regulatory releases, take compliance seriously, and work with brokers who will over-communicate through webinars and timely guidance. Section 301 creates a more planned pace than reciprocal tariffs did, allowing time to plan, but enforcement environment and regulatory complexity will increase substantially.
AI will eliminate repetitive processing work, freeing brokers and importers to focus on complex problem-solving that algorithms cannot yet handle - trade regulations, compliance strategy, and risk analysis that require human judgment and industry expertise.
Sooner than you think: holding onto familiar systems due to sunk cost and pride is expensive. Regulatory changes that break old systems (like stacking tariffs broke Shapiro's 2000-era platform) force replacement anyway, but cause more pain; proactive modernization costs less in disruption and team suffering.
They assume everyone speaks tech language and often ship features without staying current with regulatory changes like CPSC updates. Effective tools anticipate customer questions, translate jargon for non-technical users, and track regulatory releases before customers even ask about them.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a handful of genuinely useful operational nuggets - the Claude/Chapter 111 compliance gap, the stacking-tariff trigger that forced a platform migration, and the distinction between quantity vs. size of regulatory change - but they are surrounded by lengthy passages of culture platitudes and generic AI-won't-replace-people rhetoric that dilutes the signal substantially.
when you talk about Chapter 111, the brokerage regulations, and you talk about AI, the question is, are we protecting our uh, customers confidential information by using Claude? Is there any model of CLAUDE or any subscription of Claude that is in compliance
All it took was that functionality of the stacking tariffs where it said okay, you win, you win, we're moving, removing
The Claude/Chapter 111 regulatory grey-zone is a genuinely novel, practitioner-specific observation not widely discussed, but it is the sole standout; the rest of the episode recycles standard AI-as-augmentation framing, generic remote-culture tactics, and obvious tariff commentary that circulates widely in trade media.
are we protecting our uh, customers confidential information by using Claude? Is there any model of CLAUDE or any subscription of Claude that is in compliance and is there any that's not? I don't think that they've addressed that yet.
I think I would be more involved in just going out to the importing exporting community and trying to explain to them how there are companies out there that really want to partner with them
Margie Shapiro is a genuine third-generation operator who earned her broker's license, ran branch operations, and has steered a 111-year-old customs house through multiple technology and regulatory cycles - legitimate practitioner depth - but the episode does not surface the strategic or financial detail that would signal truly exceptional caliber.
My grandfather started the business in 1915, and my dad got involved when he was, I guess around 20.
I became the branch manager of our, uh, new Philadelphia operation. So I worked on the operations side. I got my license pretty quickly. I worked closely with entries, with compliance and with the customers.
A few concrete data points appear - 25-30 boomerang employees, a platform built in 2000, Section 301 targeting 60 countries, Chapter 111 - but there are no revenue figures, customer counts, cost impacts, or timeline metrics, and most claims about culture and AI benefits remain asserted rather than evidenced.
maybe 25 to 30 boomerangs
Section 301 is going to be directed at 60 countries
Brian Glick shows genuine domain expertise and occasionally pushes productively - calling out the sunk-cost fallacy, pressing for specifics beyond 'PDFs over email' - but he frequently lets soft answers stand unchallenged and the closing segment drifts into generic startup-advice territory rather than extracting more operational depth.
Besides, PDFs getting emailed instead of, uh, throwing paper across the desk, kind of what's something specific that you had to do, like to get through that transition with the culture intact?
Do you think it was kind of a similar thing where you overestimated how much of it you had to do yourself?
Computed from the transcript - who did the talking, and the words that came up most.
Margie Shapiro has led Shapiro, the Baltimore-based customs brokerage and freight forwarder her family founded in 1915, through remote work, a major tech overhaul, and one of the most turbulent tariff environments in recent memory. In this episode, she joins Brian Glick to talk about what it actually takes to keep a company culture intact through all of it. Topics covered include: * How Shapiro stayed connected and kept its culture through the shift to fully remote work * Why Margie sees AI as a tool for elevating people, not replacing them * The unresolved compliance questions customs brokers are still working through around AI tools * What it took to finally replace a legacy platform - and what she'd tell other leaders holding on too long * How the pace of tariff change is affecting the people doing day-to-day compliance work * What customers really need from their logistics partners right now Margie Shapiro is the CEO of Shapiro, a family-owned global logistics company specializing in international freight forwarding, customs brokerage, and compliance consulting.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Foreign.
Speaker B: Welcome to Supply Chain Connections. I'm Brian Glick, founder and CEO at Chain IO. Uh, today we're going to talk to Margie Shapiro. Margie is the leader at a company that shares her name, Shapiro. And, well, normally I try to come up with my own creative introduction for everybody. Uh, for the first time ever, I'm just going to read the description on the website because I think the culture of Shapiro comes out really wonderfully in her introduction on their own website. So Margie is the quirky queen bee. She loves to travel foreign films, loves to laugh, and loves to list her lists of lists. Uh, while no one can quite keep up with her, she finds a way to help us and inspire us with her warm intelligence and boundless energies. So we're going to talk a lot about culture today. We're going to talk about customs stuff and its impact on people's mental health and how all of that comes together. So I really hope you enjoy the episode. Margie, welcome to the show.
Speaker A: Thanks for having me.
Speaker B: So let's dive right in. There's a couple of canned answers to this question. I think I know which one you're going to use, but how did you get into this industry?
Speaker A: Um, I'm pretty sure I didn't consciously choose it, uh, but it was always part of my life. My grandfather started the business in 1915, and my dad got involved when he was, I guess around 20. So it's just been part and parcel of our family. I grew up hearing conversations, uh, around the dinner table about customs and ships and things that fell off the ship and airplanes and customers. And actually, one activity back in the day used to be putting canceled checks in order. So it's just part of my blood. But then I tried to resist. I went into. I studied marketing in college and I went into advertising for a little bit, and my father lured me back in. So I became the branch manager of our, uh, new Philadelphia operation. So I worked on the operations side. I got my license pretty quickly. I worked closely with entries, with compliance and with the customers. And I guess, despite my quest to stay out of the business, it pulled me. And there's something really satisfying about solving the puzzles. And international trade is just one big puzzle where the rules change every day and are really changing every day now. The more I learn, the more I realize that the industry isn't just about moving freight. It's helping businesses grow, helping products reach people, helping companies navigate this ridiculously complicated regulatory world. So I fell in love with the challenge, never really looked back. And here we are.
Speaker B: So you. I'm sure you've had opportunities to step away if you really wanted to, like, in that kind of vein of those. That kind of constant challenges. Is it kind of that stimulation that you think drives you that sort of gets you going, that like, every day it's broken? I always say, for me, it's every day the business is broken all over again, and you have to go fix it, and that I couldn't do it otherwise. Is it kind of that same. Same energy for you?
Speaker A: I think it's two things. I think it's that I love making order out of chaos, but I also love the people. You know. Global trade connects every culture and every country and every industry. So I could be talking to anybody under the sun. Every day is so different. But just to navigate the new tariffs and to help our employees try to figure out problems, to. To come up for the solutions with our customers, that is so, uh, fulfilling for me. Yeah. And now you have the changes in technology and the geopolitical changes. It keeps you on your toes, it keeps you challenged, and it keeps you engaged.
Speaker B: So one of the advice, that generic pieces of advice that I hear all the time is that you shouldn't be too in the weeds as an executive, but it sounds like you love the weeds. How do you balance being a boss, an owner, and also doing the fun part?
Speaker A: That's a really good question. I do love being in the weeds, but I also so appreciate. I work with the smartest and the best people in the industry. So I love being challenged by them. And I love when they say to me, we got it, Margie, we got it. That's fine. It's the kind of culture that we've established where it is all about collaborating together and all of us getting our hands dirty. And I think that's why we've been successful with all of these challenges that we've experienced over these decades. And we've experienced a lot of them. The reason we've excelled is that we're just all in it together, all trusting one another.
Speaker B: How much of that culture is conscious and how much of it evolves on its own? Like, is culture a thing you decide on and then build, or is it a thing that happens? How do you approach it?
Speaker A: It is so important to me. Um, it's just like, I want people to feel good. Good. I want people to feel trusted. And it became particularly relevant, I guess, when Covid hit and we had to figure out how we were going to operate, and we went to work remotely, and that could have been a challenge to our culture, but it wasn't. We've come up with solutions of, uh, staying connected and ensuring that we continue to have fun together and support one another, but also have life outside of work. So now we are fully remote. We have employees all over the country. And I want to continue to create that environment where people can do that meaningful work and continue to learn and continue to have fun together and continue to support one another.
Speaker B: Besides, PDFs getting emailed instead of, uh, throwing paper across the desk, kind of what's something specific that you had to do, like to get through that transition with the culture intact?
Speaker A: They call me the queen bee. I can't explain that. But there's a beehive, this group that comes up with things just to keep us together. So we have book groups and we have the team channel play. We just tried to deliberately engage with one another. We did wine tasting during COVID time just to make sure that we just all had fun and we remembered each other and stayed connected.
Speaker B: And there's a lot of people kind of scared out there with all this new technology. And it's, you know, we're going through yet another round of a lot of changes. You and I both saw typewriters come off of people's desks and people saying, oh, that's gonna be the end of me, right? Like, how am I gonna survive in this business without typewriter? How are you managing your team through kind of embracing some of these new technologies and. Or how do you feel about it?
Speaker A: I happen to think we're entering one of the most exciting periods our industry has ever seen, and we've seen a lot. I know that people hear AI and assume it's gonna replace people. I don't see it that way. I think AI is going to eliminate that repetitive work so that our staff can spend more time thinking and advising and solving what really matters. The complex problems. And there are complex problems that algorithms can't answer yet. Trade regulations, as you know, are becoming more complicated. Last week, a whole bunch of stuff was released that suggests that's not going to change. So our, uh, importers and exporters, they need partners who understand compliance and risk and technology and strategy. So to be able to move away from processing the repetitive work is helpful so that we can focus on what really matters. I'm also excited about the connectivity systems. Ones operated independently are finally starting to talk to each other. We always had that dream, but that will create visibility and transparency that just didn't exist before. Very interesting and fun times ahead what
Speaker B: are your customers asking for? Like, what's top of mind for them?
Speaker A: I think relationships. We target customers. My sales team, um, jokes with me about this, but I say go find customers that share our values. It's really all about relationships. Uh, so I think customers want visibility, they want analytics, but they want to be heard. So it's a question of how we achieve that with a balance. So no matter what happens or how we evolve with technology, we're never going to lose that relationship component. That's who we are. That's our core.
Speaker B: What's the most fun for you right now?
Speaker A: Hmm. I love the variety. I love being able to deal when a new, um, challenge comes out from the government. Trying to figure out, first of all, understand what they're saying.
Speaker B: You must be very excited right now.
Speaker A: Oh my God, am I excited. But we put the material together, we try to gauge from our customers what they want, we try to turn it into layman's terms so that it's not overly complicated or corporate. And then we try to build the platform to make it so that it's easy to understand. And we are there to answer the questions because there's always questions. Customs can make things very, very complicated. And we're here to kind of unravel what they're trying to say.
Speaker B: So one of the things I remember from working inside a brokerage was, you know, you have to speak kind of several languages at once, right? Because you're, you know, the direct day to day contact has this very mechanical kind of, okay, we need to get the HS code straight or we have to get the duty rate straight and what have you. And then there's sort of this other relationship you have with your customer, which is, you know, the import manager has to explain to the CFO what's going on or why, or they're mad about something that's got, that you can't do anything about. Like, do you guys think about how to talk to the customers at those different levels or is that all day, every day? I'm almost like, feel like I'm trying to explain just the water we live in. But is that something that's been harder lately? And it's obviously I, I got out of this before a lot of this new change, but like, are you able to distill this down simply but still get it to those right audiences?
Speaker A: I think my answer is going to be, I think maybe we're approaching it a little bit differently. We're trying to look, uh, at communications more proactively so that when we See something come out. We want to anticipate what the customer's questions are going to be and then we have the answers almost canned. So it's helpful that there's something that you can refer to that really spells out what's going on. So the questions are fewer, but we become more available. We are always available to answer those questions. We also are really focused on proactively conducting webinars and again in anticipation of those questions. But there's a Q and A at the end of it where we're very engaging, we collect those questions, we purpose those questions with the material back to the customers. We post those questions on our website. We try to keep our website very current and very detailed and also very fun I guess. So it's more of a continual dialogue than it is getting a call saying, where's my freight?
Speaker B: Where would you want to take if there was a little bit less of this noise? Let's say, yeah, where's the real opportunities for them? Like what would you be doing if we weren't changing the tariffs every 24 hours?
Speaker A: I think I would be more involved in just going out to the importing exporting community and trying to explain to them how there are companies out there that really want to partner with them. We are a company uh, that's focused mostly on the mid sized importer and exporter, sorry that I feel like over time has not gotten the attention that they should because of all the consolidation and there's so much opportunity for these companies and there's so much nuance in what's going on in the government right now that I think they could benefit from being heard and the collaboration on how we can help improve their supply chain.
Speaker B: What do you think the role is of in getting those things heard of, like the brokers associations and like the uh, apparel and footwear associations and like all of these different groups that we participate in. Are they helpful? Are they less able to be helpful with the uh, you know, the way that things are now? Are they more helpful? Just I'm curious because I love all
Speaker A: the people there, but I would say that the associations with whom we are engaged are helpful, especially when it comes to all of these releases, these new regulatory orders. They help to outline what's going on. Uh, there's a lot of regurgitation of what we get from customs messages, but it's restated in a little different way. And they also serve as they're available to lobby the government if something doesn't make sense. As an example, I just approached them and I hope that they will come through with this. But when you talk about Chapter 111, the brokerage regulations, and you talk about AI, the question is, are we protecting our uh, customers confidential information by using Claude? Is there any model of CLAUDE or any subscription of Claude that is in compliance and is there any that's not? I don't think that they've addressed that yet. I do think it begs a lot of questions with AI and the uh, regulate, you know, what's appropriate.
Speaker B: It's something interesting as a tech company, especially coming out of the brokerage side, because I can go to two different customers and hear 180 degree different interpretations, mainly to serve whatever purpose the person who I'm talking to usually wants to serve with them. But you're right, there isn't a very clear picture there of like, oh, well, if I'm on a corporate license, does that mean I'm okay? Or you know, do I need every importer to sign off that you know they're using the tool or can I not use it at all? Right, so like there's, you know, that doesn't even get into whether it's doing customs business or not, which is a whole nother can of worms. So with tech, uh, they've actually, there
Speaker A: is a ruling out there about the customer's business line in the sand that there is nothing about.
Speaker B: I read every word of that one and I still not sure. But so on the tech side, you got uh, a bunch of tech people who listen to this. You, ah, got me here and I'm one of your vendors. What do you wish the tech companies would do better to help you? Uh, well, now's your chance.
Speaker A: I know, I know. Maybe stay current with like as an example, the Consumer Product Safety Commission has changed the regulations just to be proactive with solutions before being presented with the puzzle.
Speaker B: So that would be what you shouldn't have to ask is, I guess is the.
Speaker A: I would like them to be ahead of it. I also think that there is a tendency, and I'll speak just tech in general, that sometimes people think everybody speaks the same language. And I do feel like the same in the vein of how you're suggesting that we try to, to drill down for our uh, customers and translate what customs is saying. It'd be great if tech people understood that everybody doesn't speak tech and say,
Speaker B: uh, those of us who do both, I can fill a room with acronyms faster than maybe anyone in the world.
Speaker A: Right?
Speaker B: You put an incoterm next to an XML tag and all Hell breaks loose.
Speaker A: So
Speaker B: now that's really insightful. So you guys have gone on kind of a tech journey.
Speaker A: Oh, have we?
Speaker B: What have you learned over the last, you know, kind of the several generations of tech that you've had through your career?
Speaker A: We had a system, um, we'll call it a platform. We loved it. It was built in, I think, in 2000, and it served us really, really well until Liberation Day. And I think despite the fact that we were trying to get off of that system prior to Liberation Day. So I think we recognize that loving something isn't always the reason to keep it. Making that decision to modernize was tremendous. It required an incredible amount of trust and effort from the team and from our customers, and we survived it. Not only survived it, we came out stronger as a result of it. So it was a big lesson. Tech moves very quickly. It moves so less quickly back in the day. And I think that I will take the blinders we're on. And I had to look up a little bit and say, wait a minute. There's tools out there that could serve our customers, our employees, and our whole product a lot better.
Speaker B: I talk to our forwarding customers about every customer that they visit, tells them how unique their supply chain is. And at the end of the day, they usually are putting boxes on boats, and the boats move across the ocean, and then it gets delivered to a warehouse. And it's. The details are sort of really. In the grand scheme of things, it's 1%. Do you think it was kind of a similar thing where you overestimated how much of it you had to do yourself?
Speaker A: No, I think it was pride. And I think that when we built it back in 2000, I mean, it had bells and whistles that nobody ever thought of. And I think we lost sight of what everyone else was thinking or how we could do things a lot easier. And it was a very expensive lesson. But I regret the pain and the suffering. I mean, this was through Covid. And then we finally launched right when, uh, Liberation Day struck. So there's a lot of healing as a result of this. It's a big lesson that I will never revisit.
Speaker B: Well, sorry for making you revisit it then.
Speaker A: No, I mean, you know, it was lesson learned. I can laugh about it now.
Speaker B: You know, there is a thing there that we see all the time. Right. Ah. Which is. I don't know that it's always that our customers. It's that. That they don't want their baby called ugly so much as, like, there's A real sunk cost fallacy sometimes.
Speaker A: Absolutely.
Speaker B: In like, you know we've put so much into this, if we just put a little bit more into it, it'll be right where we need it and then it's always like one uh, step out of reach.
Speaker A: Yeah. All it took was that functionality of the stacking tariffs where it said okay, you win, you win, we're moving, removing.
Speaker B: Sometimes the future comes uh, up slowly and sometimes it walks up and slaps you in the face.
Speaker A: Right, there you go.
Speaker B: So what are you guys investing in now? What's exciting you on your customers behalf?
Speaker A: The next generation is what's exciting me right now. I'm just really thrilled about the people that are joining the company that you know, as I said we're fully remote. So we now have people available to join the company from all over the country. So they're asking different questions and they're challenging those long held assumptions like those automation systems. So I'm excited by them. Also have a lot of boomerangs employees that leave and come back. I mean like a lot of boomerangs, maybe 25 to 30 boomerangs. So it's exciting what they've learned and they're bringing back home. So I don't know, that's really exciting to me. I'm excited. This little family owned company that's 111 years old can still reinvent itself.
Speaker B: If there's one metric of how good is a culture it's how many boomerangs do you have? Right.
Speaker A: Yeah. I'm so fortunate. I work with the best people in the industry.
Speaker B: That's wonderful to hear. Give me one prediction about something you think is going to be different in a year.
Speaker A: I think that the whole tariff regime is going to get particularly, I want to use the word ugly. It's just going to be different. We'd gone through a lot of iterations of IPA, uh section 122. Now this section 301 is going to be directed at 60 countries. It's going to be a very challenging year for importers.
Speaker B: What can they do to be a better customer to you?
Speaker A: Pay attention and we will be as over communicative as we possibly can and as timely as we possibly can with correct information with a lot of webinars. But pay attention and take it seriously because I do feel like this, it's uh, an environment of enforcement and it's going to be an environment of a uh, lot of complicated regulations.
Speaker B: I would imagine that there's quite a few people out there in your customer base who just, at some point they just get exhausted.
Speaker A: Right.
Speaker B: And they say whatever happens will happen. I can't deal with this today kind of vibe. Is that, uh.
Speaker A: Yeah, I'm surprised that as many customers stayed around during the reciprocal tariff era where those tariff rates were so high. I mean, I just, I'm surprised that they hung around. I don't know, it's. It's really getting challenging to make sure you do things correctly.
Speaker B: I kind of get the impression when I think about the, like the actual humans at the importer, right. That there's kind of two different people who are affected in different ways. Like there's. If the tariff was going from 3% to 3.1% to 3% every day, it changed. There's a group of people where the, the number doesn't matter and then there's another group of people where it goes from 3% to 63% and it matters a lot. Right. Even if it only had like, I'm guessing at uh, like the desk level at the day to day, like the people who are getting ground down. It's the quantity of change, not the size of the change. Is that a thing?
Speaker A: Like. I think it's the quantity and the pace. Yeah, the pace was a killer now because of 301, it has to be a more timed pace because you need approval. But. But with the reciprocal tariffs turned on with the stacking and the rules and the degree of tariffs, that was brutal. I don't know that it'll be that brutal because there is that time that you can at least plan a little bit. But even now, uh, from a supply chain standpoint, you're seeing front loading to try to beat the Section 301 tariffs.
Speaker B: Are you sending your employees the courses on how to become therapists yet or. It was a big part of the job.
Speaker A: That's what the wine tasting, um, online wine tasting is all about.
Speaker B: That's a reasonable way to adjust to regulatory environment, I guess. Well, Margie, it's been so great chatting and I really appreciate you coming on. I'm going to ask you one last question. Just if you're talking to someone who's starting a company today, what advice around culture, around, you know, kind of how to think about building a team is kind of rule number one for you.
Speaker A: I would say go for spirit. Attitude is everything. Attitude and curiosity and commitment and quirk. Embrace the quirk. We all need to have fun. But to me, attitude is number one. Realness is, I guess, number two.
Speaker B: Awesome. Well, again, thank you so much for being on it. Was a pleasure chatting, as always.
Speaker A: It was great chatting with you too, Brian. Thanks for convincing me.
Speaker B: Thanks so much to Margie for that chat. You know, it's great to me when you can talk to a leader who really lives the culture that they're trying to bring. And you can really see the sincerity in everything Margie had to say on the Chain IO front. Just a couple of quick updates really, uh, encourage everyone to take a look at what we're doing at Checks Chain IO, which is our new product that is really helping a lot of our customers understand how to take complex SOPs and really difficult compliance and customer specific rules and tie those back to their tms in a way that not just reduces labor, but especially improves the customer satisfaction by really keeping a coach next to your employees to help them improve their quality and uh, really meet your brand promise to the customers. So check that out at checks Chain IO and as always, I'm Brian Glick, founder and CEO of Chain IO, and I will speak with you next time.
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