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This week, Netflix’s Bernie Madoff docuseries sure has Chris and Gina thinking about trust. They discuss trust as the key to any partnership, even (and especially) in business, and its role as the backbone of client services. Through the lens of MADOFF: The Monster of Wall Street, they break down how to build trust, what might break it, and how the docuseries has given them perspective on trust in the workplace.


Gina Trapani: It would not take much for this bus… (laughs) to break this divider and land in the river.

Chris LoSacco: Oh my God. Okay.

Gina: And we will all die a watery death, right? But here’s the thing, like…

Chris: This is what you’re thinking about on your ride to the office in the morning?

Gina: This is… this is what I… (Laughing) It’s a really big bus, Chris. And a very small divider.

Chris: Okay.


Chris: Hello and welcome to the Postlight podcast. I’m Chris LoSacco, the president of Postlight, and I’m joined as always by my business partner and the CEO of Postlight, Gina Trapani. 

Gina: Hey Chris, how are you today?

Chris: I’m good. We were just talking about how absolutely frigid it is here in New York City, so…

Gina: Yes.

Chris: Wear a coat? I don’t know, maybe that’s the way to start off this podcast.

Gina: Wear a coat, hot chocolate, marshmallows. Light up a fire.

Chris: There we go. That’s, see, now we’re all cozy.

Gina: Put on those fuzzy socks, we’re going into the weekend. Yeah, yeah, we’re all cozy.

Chris: Yeah. Let’s picture our listeners in front of a wood-burning stove, and…

Gina: (Laughing)

Chris: …you know, mugs in their hands…

Gina: Mugs in their hands, exactly.

Chris: …with steam coming up as they listen in to the dulcet tones of the Postlight podcast.

Gina: Thinking big thoughts. Exactly, exactly.

Chris: So, I’m gonna kick us off today by asking you a question.

Gina: ‘Kay.

Chris: And this is a little bit of a leading question. If you had to say, what is the bedrock of a client services business. Like, what is the most important thing that you need to think about as you do your work? What would you say it is?

Gina: The relationship with your client. And the most important thing to all relationships is trust. 

Chris: Trust.

Gina: These are very mushy answers. Like, we build software for our clients. (Laughs)

Chris: Right.

Gina: So you expect me to be like “Well, the tools that we use and the best practices and the level of skill set, you know.” It’s actually… we can only be productive in a partnership with our clients, a client-vendor… you know, client-partner relationship, if you have a great relationship. And I think the only way to have a great relationship is there’s trust between you.

Chris: Yes. And you also need trust within your team.

Gina: Absolutely.

Chris: In order to do your best work, you need to trust those that are around you.

Gina: Trust with your customers, trust with your teammates. I think that trust is key to every relationship and every business, especially in a client services context.

Chris: Yeah. What do you mean, “every relationship”? 

Gina: I think if it’s a romantic relationship, if it’s a business relationship, if it’s a…

Chris: Mm.

Gina: Every kind of relationship, there has to be some trust, you know?

Chris: Yeah.

Gina: And sometimes when you, like, when you’re starting a relationship with someone… and this, you know, client services context. Sometimes you take a little bit of a leap of faith.

Chris: Sure.

Gina: Like, “Okay, I’m gonna vet this person. Are they credentialed? Have they been referred to me from someone that I know?”

Chris: Mhm.

Gina: Is there a track record of doing the thing, right? So you sort of, “Alright, I’m gonna take a leap of faith, and I’m gonna decide to trust.” So I take the express bus to the office.

Chris: (Laughs)

Gina: So I live in Brooklyn…

Chris: And you love it.

Gina: (Laughs) I do. I love it. I talk to you all the time, I talk to Chris all the time about how much I love… and if our clients at the MTA are listening, express buses. I’m making the heart sign.

Chris: Right. All the way.

Gina: All the way. I live in Brooklyn, our office is in Manhattan, and as an alternative to the subway there are these express buses which are inter-borough buses. They’re these giant, giant buses, and you can get on it in Brooklyn, and like within one stop be in Manhattan. And I absolutely love my express bus ride because we drive in this giant bus, at very high speeds, along the FDR expressway, which is on the east side of Manhattan. And it’s beautiful, because it’s the morning and the sun is coming up and I’m passing, like, the Brooklyn bridge and the Manhattan bridge and the water’s sparkling and I’m looking over Brooklyn, it’s just this meditative moment in the morning. I get to kinda stare out the window and prep myself for the day, and it’s lovely. But I have catastrophe brain.

Chris: Okay.

Gina: And there’s a part of the FDR, which is a raised highway, that’s right over the water. And the bus always is in the right lane. Again, a giant bulky bus.

Chris: Okay.

Gina: Right on the edge of the highway. And between the bus and the East River, there is like a very small concrete divider. Okay?

Chris: (Laughing) Okay, okay.

Gina: And so, I often look out this window as we’re barrelling down this giant highway, and think It would not take much for this bus… (laughs) to break this divider and land in the river.

Chris: Oh my God. Okay.

Gina: And we will all die a watery death, right? But here’s the thing, like…

Chris: This is what you’re thinking about on your ride to the office in the morning?

Gina: This is… this is what I think… (Laughing) It’s a really big bus, Chris. And a very small divider.

Chris: Okay.

Gina: But here’s the thing, right? I grew up in New York City, I took the local bus to high school, I’ve been riding the subway my entire life. In the morning I get on the bus, I pay my fare, I sit down, I don’t know the bus driver. I don’t know them, right? But I know the MTA. There’s been 40-some-odd years of, I’ve been riding MTA vehicles. There’s a trust. I trust…

Chris: Right. Mhm.

Gina: (Laughing) …that the bus driver’s gonna keep the bus in the lane. I trust that the lane isn’t blocked. I trust that the car on the other side isn’t gonna just drive over the divider. There’s a lot of, like, kind of implicit trust in the world, right?

Chris: Sure, yeah.

Gina: You’re just like, “I’m gonna take the risk that this is just gonna work,” right? Some things we take for granted, and maybe I’m the only person on the bus thinking about how easy it would be for us to land in the water. Maybe that’s just my psychology.

Chris: (Laughing)

Gina: But I think about, a lot about that. Like, “Okay, I’m just gonna trust that these elevators that I get on is gonna…” You know, my brothers and my father worked in the elevator business.

Chris: Sure.

Gina: I’m gonna trust that this elevator is gonna make it to the floor, and the cable’s not gonna break or not… there’s a lot of trust there. Separate sort of thread, here. I watched… which, I talked your head off about this already, so I apologize.

Chris: You were very jazzed about this.

Gina: I was very jazzed about this. So, there’s a docuseries on Netflix right now. I think it’s called, like, “The Monster of Wall Street.”

Chris: Mhm.

Gina: It’s the Bernie Madoff story. It’s a series.

Chris: Right.

Gina: I would recommend it. There’s some cheesy, you know…

Gina and Chris (Together): Reenactments.

Gina: But there’s some really smart commentary from journalists, et cetera. So Bernie Madoff was this guy who ran this giant Ponzi scheme. That was really all I knew about him. I didn’t think about finance or investing at the time when all this went down.

Chris: Yeah, me too.

Gina: So I sort of missed…

Chris: The details of the whole story. Yeah, yeah, yeah.

Gina: Yeah. The details of the whole story, the enormity of what happened. And I could talk about the enormity of what happened, and how this Ponzi scheme… in my mind I was like, “This must have been a very complex and difficult con to pull off.” No. No.

Chris: No, no no no.

Gina: He just took money and didn’t do anything with it, and then he gave it to the people who were… it’s just a pure pyramid scheme. Right? People at the top of the pyramid made money.

Chris: Right. 

Gina: It just… there was nothing happening in the background.

Chris: There was nothing happening. I mean, this was what was so staggering to me, watching this show. The numbers, like, the dollars that were flowing through this scheme? It is hard to wrap your brain around. I mean, it’s billions of dollars. 

Gina: Yes. It’s so much money.

Chris: That he was taking in, and just printing fake statements to his clients and sending them, and saying, you know, if anyone had any inkling… like, “Can I see the trade confirmations, Bernie, of what’s going on?”

Gina: Yeah. Yeah.

Chris: He would be like, “Listen. If you don’t want to be involved, I’ll give you the money right back. No problem.”

Gina: “Don’t worry your pretty little head about it.” Yep.

Chris: “Don’t worry about it. I’m handling things, but if you’re not interested I’ll give you your money and you can be on your way.” And I mean, they don’t… I mean, they don’t go through every single client, but the impression is a lot of people, they back down! They were like, “Okay. Keep giving me the returns I’m getting.”

Gina: Yes!

Chris: Which is just… unbelievable. I mean it is believable, I guess, in that people don’t… you know, if they have something that is so so good, they’re like “Well, I guess I don’t want to turn over the apple cart, so I’m just gonna keep riding it for as long as I can ride it.” But the reality is, if it’s too good to be true it probably is!

Gina: That’s right.

Chris: Like, there’s a problem. You know?

Gina: Yes.

Chris: And the clients who were deeply invested with him were like, you know, prisoners to these returns, and feeling like “Oh, well, I’m just gonna trust it.” It coming back to this idea of trust.

Gina: It doesn’t make sense. A lot of these people were financial professionals.

Chris: Oh my God.

Gina: I know that consistent 10-15% market returns, quarter over quarter, like no one else is able to do this. And I don’t really know how it works. But this guy’s doing it for me, so I’m gonna trust him. And here’s the thing about Madoff. I mean, no one really knows why he did what he did. But the documentary sort of hints that he just wanted so much to be trusted, to be loved, to be celebrated.

Chris: Yes.

Gina: This was a person who crafted a persona. He was just a huge figure on Wall Street. He was like the chairman of NASDAQ. He…

Chris: Of NASDAQ. I know.

Gina: He really pushed the industry. He was at the forefront of making trades electronic. I mean, there was a time… I can’t even fathom this, as someone who just for fun dabbles in things like crypto and online trades. People used to mail paper cheques and get paper stock certificates when they performed trades.

Chris: Oh yeah.

Gina: Trades would take a couple weeks to complete. Which is, you know, bananas to think about this in 2023, and a lot of what Madoff did was modernize and make these things electronic. So people saw that as a, you know, he had computers, and… But he cultivated this persona, and he… this is the thing, as a client services professional, that really made such an impression on me, and why I wanted to talk about trust on this show, is that he… I think he truly loved and cared about his clients, and he wanted, they wanted him to make them rich. He wanted to make them rich. I mean, one of the fascinating… and at the end, this all fell apart. Madoff actually wasn’t the one who made the most money in this whole scheme. His biggest client actually took home more money than he did.

Chris: Right.

Gina: And there was… because he had built this huge persona, this credential of himself just being this absolute magician, you know, who could just create these returns that were statistically impossible, there was no shortage of new clients. People were banging down his door. He was turning down new clients.

Chris: He was turning people away! It was like “Oh, who do you know? How can you get in by getting a recommendation at this exclusive club that only a few people have access to.”

Gina: Right. That’s right, that’s right. So he created more demand, which you need constant demand in order to run a successful Ponzi scheme for whatever, I don’t know, what was it, like 20 years or something? It was a long, long time before it fell apart. And there were just so many red flags… I mean, I, listen. I’d like to think this guy could have never caught me. But, you know, if I’m being honest with myself… (Laughs) I would want those 10-15% returns. I would want to think that I was so smart and so important and so exclusive that I had gotten into his club…

Chris: Right. You had figured something out that no one else could figure out.

Gina: I had figured something out, he had figured something out… I didn’t know what that secret sauce was, but I was just going to trust this person because… the SEC investigated this guy, like, multiple times! And said okay!

Chris: And gave him the green light!

Gina: Gave him the thumbs-up. Gave him the thumbs-up. 

Chris: All good. That little tidbit about how the SEC sent, like, junior analysts to look into all of this and then they came out with a clean bill of health. That was staggering, when we were watching the show. Like, wow.

Gina: Yes. Yes.

Chris: It’s unbelievable.

Gina: Unbelievable.

Chris: And how can you blame these investors, right? The individual investors and the institutional investors who see… you know, they look over and they’re like “Oh. The SEC looked into this and they were like, A-OK.”

Gina: Must be legit. Yeah. Must be legit.

Chris: I mean, I think the takeaway is, trust but verify.

Gina: Trust but verify.

Chris: You need to have your head on straight when you’re thinking about something, and if something seems too good to be true, it probably is too good to be true.

Gina: Probably is.

Chris: And so you need to look at that.

Gina: You need to interrogate it. So this is something that I would advise anyone working with a partner, with an advisor, with a client services firm like us. Whether that’s building software or managing your finances or building a new room on your house. If you ask the question, “What you’re promising isn’t possible, I need you to explain to me in plain English what exactly are you doing. What are you doing, how does this work?” If you don’t get a clear answer on that, that’s a red flag.

Chris: That’s a huge red flag.

Gina: Huge red flag. If you’re never getting bad news… I mean something, this is a mantra inside Postlight, right? Bad news shared early…

Gina and Chris (Together): Is just news.

Gina: Part of any partnership is having to say, “You know what? This isn’t going well. We’ve got a problem and we gotta sort it out.” Right? This thing that we thought we could do, we couldn’t do. It doesn’t sound like this person, Madoff, he never wanted to give his clients bad news, right?

Chris: Right.

Gina: And his clients were multi-million dollar and billion-dollar. These were important, wealthy people, he wanted to be part of their world. He just wanted them to be happy. And you know, as a people pleaser personally, I’m a people pleaser, which is part of the reason why I work in client services. 

Chris: (Laughs)

Gina: But I have to really fight my people-pleasing instincts.

Chris: Yeah.

Gina: You are really good at this. You’re like, “Let’s run toward the uncomfortable conversations,” and I’m like “I would just like to jump out the window.”

Chris: (Laughs)

Gina: (Laughing) That’s just my instinct, is like, I just want to say yes we can help you, we are here for you. And all those things are true. But then there are times when you have to draw boundaries, and you have to say “Actually, this thing that you’re asking for, it’s not in scope.”

Chris: Right.

Gina: Or “This thing that we thought we could ship at this date, we cannot for these reasons.”

Chris: Ain’t gonna happen. Yep.

Gina: It’s not gonna happen for these reasons. Here’s what we’re gonna do, here’s the alternate plan. I know this is news that you didn’t want to hear, but I have to be upfront with you the soonest as possible, right? And it sounds like he just never… he never wanted to… I mean, the whole thing absolutely, it blew my mind but I kinda get it. I get it as somebody who genuinely wants to help. I mean, helpers are in client services, right? Like, you want to help your clients. You have to understand that helping your clients is giving them news that they don’t want to hear sometimes. And telling them this is the deal, this is what we’re doing, this is the value I’m bringing you, this is how much of a commitment I need from you and collaboration I need from you. That’s just, that’s a basis of really every relationship.

Chris: I totally agree.

Gina: Here are my needs, here’s your needs, we’re gonna work together to meet them.

Chris: Right. It’s communication, just like in personal relationships, you need to communicate about… just like you’re saying, what your needs are, and listen and understand what their needs are, and talk about, on a regular, consistent basis, how those needs are being met. Like, that is absolutely critical. It is the bedrock that you build any relationship, personal or business, right?, on as you work with somebody. I mean, the other thing I would say is, it’s kind of like advice to the client services professional or anybody who’s in a work context who wants to be kind of the anti-Madoff, to build trust: Show your work. Don’t try to hide it.

Gina: Don’t make it super abstract, use a bunch of buzzwords and acronyms. Right.

Chris: No. Be very plain, very direct. Also, don’t wait for it to be perfect. Like, I think it’s a very common thing, especially when we work with people who are earlier in their career, that they want to make sure that they’ve thought of everything.

Gina: Yes.

Chris: And they have the, you know, bulletproof 85-slide deck that they’re gonna walk a client through. And it’s like, okay, maybe there can be a time and a place for that, but there’s also a time and a place for, “Listen. This is like 25% of the way done, we just want to gut-check it with you. We wanna make sure that we’re going in the right direction. We know that there are wings of the house that are completely not done, not even started. But we’re going to put this in front of you because we want to show you…” I mean, in our world, in the software world, we have a saying that we say all the time to each other which is, “You can’t argue with working software.” 

Gina: That’s right.

Chris: Right? If you show someone a prototype where it’s like, it’s not done but it’s coming together and you can start to click on something, that is a tremendous asset for building credibility and building trust. And you’re not doing anything that you wouldn’t otherwise do, you’re just bringing the client, you’re bringing the stakeholder into your world. You’re bringing them onto your side. And if you do it in a way where you’re not trying to, you know… you don’t have to prove yourself. You don’t have to show off and say, “Look at everything we’ve accomplished.” Right? Instead, just be honest and be direct and say, “Here’s where we are.” And that can be such a tremendous trust-building moment of connection, because it aligns you, right? It aligns your quote-unquote customer, if you want to think about it that way, and you and your team, and you’re working in the same direction rather than saying “Well, I have to make sure that I’ve crossed every T and dotted every I before I talk about what we’re doing.” It’s maybe a little bit… not counterintuitive, but I think it’s not what people reach to always, but there’s tremendous power in it. 

Gina: Tremendous power. Right. Because you’re showing your work, you’re being open. “Look, I’m delivering value, it’s coming along.”

Chris: Yeah.

Gina: I’m proving to you that I’m doing… and the thing about trust is… so. In the beginning of a relationship, you kinda take a leap of faith. I’m gonna take what this person says at face value. Maybe I’ve checked their references. Maybe I have looked at their track record. And now we’re in a working relationship together. And I think one of the interesting things about working in client services – and Michael Shane, our head of digital strategy, says this a lot, right? – so you earn trust. Sometimes you take a leap and then you start working together, and you have to earn folks’ trust. And a lot of people start out skeptical, but most people start out giving you the benefit of the doubt and saying “I believe that you’re going to do what you say you’re going to do,” like when I board the bus in the morning.

Chris: Yep.

Gina: But then you have to earn and re-earn. Michael always says, like, “We constantly have to re-earn the permission to work with our clients.” Right?

Chris: That’s right.

Gina: In our line of work, we know that there’s a CFO at every organization that we work with who scrutinizes the costs, and looks at the line item for Postlight, and says “What is this and what value are we getting, and is it important to our business?” Probably every month.

Chris: Exactly. Yep.

Gina: At least every month when they’re closing the books. We know that, so we constantly have to hustle to earn and re-earn. And there have been relationships, as relationships go, we’ve had relationships with clients where there was a breach. Like, we messed up. Or they messed up! Meaning, like, you know, they misrepresented, or something was promised and not delivered, right?

Chris: Yeah.

Gina: And we have to have that basis, that bedrock of trust that you earned to begin with to fall back on, and then you’ve gotta work to re-earn. Right?

Chris: That’s right.

Gina: There’s a constant sort of, if you think about it as a bank account, right? You’re making deposits, credibility deposits, trust deposits. We’re building, you know… and then sometimes you’ve gotta withdraw, when things go wrong. Because in every relationship, every real working or romantic or whatever relationship, things happen. (Laughs) Things go wrong.

Chris: Of course.

Gina: And what’s your ability to recover from those?

Chris: Exactly. And if that is out of whack, right? If you’re making more withdrawals than you are deposits, then something… you know, it’s not gonna work long-term. And something’s gotta be corrected.

Gina: Yeah. There were two aspects of this Madoff story that stuck with me. First was that, he hired some software developer. This was early 2000s, right? Software wasn’t like it is today. But he essentially hired a couple of software developers to build custom software which would create trades, like trades in retrospect that they knew were going to go the right way and earn what they want. And then they had these dot matrix printers that would print out the client statements, and they would send these statements out. And in one of the voice-overs, they were like “These printouts were so… like, no credible, legitimate firm created artifacts like this.” You know what I mean? With the little holes on the edges.

Chris: (Laughs) Right.

Gina: And it was just, there just wasn’t a whole lot of information except this trade, and almost entirely every trade netted gains, and they would take their fees… and you know, it was weird. The first time we looked at a Madoff statement, we were like “This firm is huge, and they’re doing millions, hundreds of millions of dollars in business, and they’re printing out this garbage artifact.” Which was just so, like… (Laughs) It was just so funny to me. It was strange to me that he didn’t say, like, “Let’s create more believable artifacts.” But that’s how little he really cared about… like, he built up his own sort of veneer, but the artifacts he was creating for his client, they were sort of intentionally opaque and old-school and just not legit-looking.

Chris: Exactly, yep. Yep.

Gina: And these programmers, I just… there was some part of me that was like, “You conducted this fraud, there’s no way you didn’t know how this worked, ‘cause you built it.” But wow. Wrong place at the wrong time, for sure.

Chris: I mean… for sure.

Gina: The other aspect that killed me, there was this one mathematician at maybe a competing firm, or… but who basically looked at Madoff’s promises and returns, and said “This is statistically impossible. I’ve run every single model.” And it’s funny, you know, in the docuseries they stage it like he’s in this dark room, you know. 

Chris: (Laughs)

Gina: This nerdy dude in this dark room…

Chris: Clackin’ away at his keyboard.

Gina: Clackin’ away at his keyboard. And he’s enraged. He’s enraged that people are believing this. And also he gets this mandate, “Build the model based on what Madoff is doing so that we can offer a similar service.” Right? Like, his competitors are just flummoxed, they don’t know what he’s doing.

Chris: Right. They’re trying to work backwards. I mean, he comes to the conclusion “It can’t be done.”

Gina: Right! So this guy is like, “it can’t be done.” So he’s enraged, because no one believes him. He goes to his bosses, he goes to the SEC. In the end he becomes the big whistleblower. But one of the takeaways for me, you know, we have situations where we’re in the middle of a big project, and there are times when an engineer or designer or product manager will come to us and be like, “This thing that we promised, or that we say we’re doing? It’s not possible.” And it’s funny because, you know, on one hand it’s like “Oh, this person’s raising a risk, and we should address it and mitigate it.” And there are other times when you’ll be like, “Is that true? Is this something… let’s think of solutions,” right? Like, let’s find the solution here.

Chris: Right.

Gina: Like, I don’t… let’s not think about the problems, let’s think about the solutions. And it’s funny, because I think this person was dealing with that. I think that his bosses were like, “Figure it out, man. They figured it out, we should be able to figure it out.” Like, what…

Chris: (Laughs)

Gina: And how frustrating that can be. 

Chris: Right.

Gina: So it’s this, like… when people raise risks, when is it being too worried and too problem-oriented and not solution-oriented, and when is it like, this is full-on just absolute fraud, and we’re all heading for a giant crash into the little divider and about to fall into the East River? Which is basically what happened on the market.

Chris: Right. Right.

Gina: (Laughs) At the end of the whole… to tie it all back. I don’t know. I don’t know if you thought about that at all, but I just was like “Oh, the nerds, yes. The mathematician calling it all out.”

Chris: I know.

Gina: Speaking truth to power and saying “This is not possible.” Like, that guy made a huge impression on me.

Chris: I mean, the truth is though, I think what he stumbled upon is kind of an outlier.

Gina: Right.

Chris: The fact that this was so egregious…

Gina: Yeah.

Chris: I think most of the time it’s a gray area, right? And it’s somewhere in between, where there’s something that isn’t right and something that does need to be looked at, and you do need to go one step deeper. But also, like, most of the time there is a way out of the fog, you know?

Gina: Yep.

Chris: In this particular example, there wasn’t. He was… it was a Ponzi scheme.

Gina: He unearthed a huge problem, yeah. Yeah. That no one was… everybody else was almost woefully ignoring.

Chris: Right. Right. I think, though, when I think about, okay, well, how do I… what do we take away from this that allows our teams to work better with our clients? To me, it comes back to expectation-setting, you know? And in the Madoff example, he had these crazy unrealistic expectations that just got more and more bananacakes as time went on, and it was all fake. He achieved it because it was fake. He didn’t really achieve anything. When it comes to our work, I think it is about setting realistic expectations, right, with our clients. And then you either meet them or exceed them, and you’re making deposits into your trust account every single time you meet an expectation, whether it’s on a big milestone level that you spent four months on, or if it’s a spring that you achieved really well over a week or two.

Gina: Yes.

Chris: And if you are not gonna meet your expectations, that’s where the idea of sharing bad news early comes in. And it’s just news, right?

Gina: Right.

Chris: And you… if you think you’re on track to not meet an expectation, you can actually get ahead of that too, and you can mitigate that, and you can turn that… you need to embrace the vulnerability of saying “I’m in a tough spot, and I’m gonna come to you.” (Laughs) And…

Gina: Right. And I’m gonna be vulnerable. I’m gonna say if I messed up, I’m gonna say “I’m concerned and I want to fix this and this is what’s going on.” I’m gonna lay it out on the table. “Here’s what’s going on.”

Chris: “Here’s what’s going on.” 

Gina: I know this isn’t really what you want to hear, but this is what’s happening, and we’re gonna fix it.

Chris: Right.

Gina: Yeah. Lies snowball.

Chris: Lies snowball.

Gina: I was watching this guy and I thought, this guy was like a young kid trying to make a name for himself, and started this scheme, and then he just got caught up in this snowball of lies and omissions and fraud, and his career started rocketing, and he couldn’t…

Chris: He couldn’t get out.

Gina: He couldn’t get out. Lies and omissions and deferments and obscuring hard truths. Like, we talked about this earlier this week! We had a hard conversation, and it was like, the longer you wait to have a hard conversation, the harder it gets. It almost gets…

Chris: Exactly.

Gina: And I think this person just got carried away for literally decades…

Chris: Yeah.

Gina: …by his own fraud, by his own lies. Like, and he wound up, you know, in jail and dead… You know, it was a really bad scene, and his family fell apart. When I don’t want to share a truth, or when I feel like a relationship is at risk or something happened that was hard, I have to just be like, “You gotta just address that head-on.”

Chris: Yeah.

Gina: Gotta just say it.

Chris: Right.

Gina: Because it can just snowball and get worse.

Chris: You’re a thousand percent right. You gotta avoid the snowball. Address it when it’s a tiny, handheld snowball, instead of like a boulder that’s rolling down a hill. (Laughs)

Gina: Right. Exactly.

Chris: Have you ever played the worst-case scenario game?

Gina: No.

Chris: It’s not a game. But, like… you can also ask yourself, if you have a hard conversation to have, what is the worst-case scenario? 

Gina: What is the worst thing that’s gonna happen?

Chris: And almost always, it’s not that bad. ‘Cause if you play out the worst-case scenario, like “Oh, my partner’s gonna have a tremendously bad reaction and leave me,” or “I’m gonna share this with my boss and they’re gonna fire me on the spot.” It’s like, if you really interrogate it, the likelihood of that worst-case scenario actually happening is like 0.001%.

Gina: Right, right.

Chris: It’s almost always not gonna be that bad. And so, if it’s helpful, you can sort of reassure yourself by saying “Okay, there is fear, right, or something that’s coming from that worst-case scenario, but that doesn’t have to make my decision for me. Because that’s not the most likely thing that’s going to happen.” Instead, what’s most likely going to happen is that this is going to be the first step towards, you know, a more positive outcome, having this hard conversation.

Gina: Yes. Yes, absolutely. I probably play worst-case scenario in my head… (Laughs)

Chris: (Laughs) Well, apparently you do on the bus.

Gina: Yeah, I think there’s a difference between catastrophic thinking and worst-case scenario. But I love that. Like, what am I really afraid of? I feel my brain seizing up right now, what am I really afraid of? And teasing it out, and being like “That’s actually a very unlikely outcome” is a very important exercise.

Chris: Yes. Totally.

Gina: Yes.

Chris: We love having these conversations, and we actually, we have built our business on the idea that we have to speak directly, and not rely on trust, constantly re-earning it. And we’re never gonna be the kind of firm that just says “We’re gonna wave our hands and you don’t worry about what we’re doing, because we’re the experts.”

Gina: Right.

Chris: We are definitely the anti-Madoff in that regard. If you’re listening to this and you’re thinking, “That’s a dose of medicine I would like to take, I’ve been struggling with something and I really just need someone to give it to me straight and hopefully get off on a better foot,” you are a great potential Postlight client and we would love to talk to you if you hit us up at It is an email inbox that comes directly to Gina and me and our digital strategy team, and we have people who want to have these conversations, believe it or not. So we will talk to you. We could also just talk to you about, you know, the crazy reactions to the Madoff documentary if you wanna do that too. The email address is the same:

Gina: Yes! If you watched it I want to hear your take, because I can’t stop talking about this thing. (Laughs) Thanks, Chris.

Chris: Thanks, Gina. Talk to you soon.