Jan. 15, 2026
Dub's COO, Brett: Why “Move Fast” Breaks Fintechs
In this episode of Risk and Reason, Eli Wachs sits down with Brett Chereskin, COO of Dub, to unpack how real fintechs think about risk, fraud, and operational discipline at scale. Drawing on his background in military intelligence and aviation, Brett shares why incentivized growth attracts fraud, how attackers probe systems before striking at scale, and why early stage companies must calibrate risk based on what they can actually monitor. The conversation explores mission driven leadership, prudent risk taking, and why operations is often the most underrated competitive advantage in fintech.
Chapters
(0:00) Incentives, Growth, And Fraud Tradeoffs
(1:03) From Military Intelligence To Fintech Operations
(4:28) Aviation Lessons On Risk, Buffers, And Failure
(8:43) Why Operations Is A Startup Superpower
(14:55) Mission Command And Prudent Risk
(18:30) Scaling Fraud And Compliance The Right Way
(29:35) Rapid Fire: Metrics, Discipline, And Dub’s Advantage
Follow Brett Chereskin
LinkedIn: https://www.linkedin.com/in/brettchereskin/
X (Twitter): https://x.com/bchereskin
Follow Eli Wachs
LinkedIn: https://www.linkedin.com/in/eliwachs/
Check out Footprint
https://www.onefootprint.com
Footprint helps fintechs and banks verify identity, prevent fraud, and manage compliance with end-to-end onboarding and risk infrastructure.
00:00 - Fraud Guardrails And Incentives Debate
01:02 - Welcome And Brett’s Path To Fintech
02:11 - North Atlantic Flight And Risk Math
06:13 - Why Operations Is The Startup Backbone
10:42 - From Army To Affirm: Finding The Ops Gap
14:52 - Mission Command And Prudent Risk
18:10 - Calibrating AML, KYC, And Growth Levers
22:05 - Incentives Attract Fraud And How Attacks Scale
25:15 - Building A Security Foundation Early
27:27 - Becoming The Target And Defense Tactics
30:12 - Discipline Through Hands-On Support
32:46 - Closing Remarks And Next Steps
WEBVTT
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Let 's make sure we put a buffer into the minimum account deposits to prevent ACH fraud.
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Let's spend this next month and a half integrating footprint, for instance, versus building the next new feature that can drive viral growth.
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Even something along the line of, hey, do we want to use incentivized onboarding?
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The minute you start giving away even a dollar, fraudsters will come knocking.
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And they'll come knocking in mad.
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We actually had that conversation.
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Hey, do we want to offer like 20 brokerage dollars if somebody refers somebody or if somebody like signs up?
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And it's immediately, the minute you do that, you're going to pay the price.
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And then they're going to start testing you, and then they're going to attack you all at once.
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I thought that affirms.
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Like attacks don't attack them once each easy.
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It might be some penetrating attack that they're trying to figure out, like vulnerabilities.
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And then once they find it, they go quiet for like months.
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Boom.
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10,000 people all came in to the exact same thing, and now you're upside down and didn't have enough time to show it off.
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Welcome back to the Risk and Reason podcast.
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I'm thrilled to have Brett joining us today.
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We've known each other for, I'm going to generously say a couple of years by now.
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That may or may not be true.
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But it feels like that.
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At least I've been annoying you on Slack for that long.
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Brett has a really cool background.
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You spent, I want to say 12 years in the U.S.
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Army and have worked at some of the most iconic fintech companies that have scaled tremendously, such as a firm leading operations internally.
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Most recently, you are the COO of Dub, which is the fastest growing investment platform.
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I think I recently saw 13th on the App Store.
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If Steven's LinkedIn posts are to be believed.
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So really a tremendous career, but I want to turn it over to you because I'm sure I missed a bunch of it.
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Tell us about how how did you get into the world of fintech and ops and everything in between?
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Yeah, I think thanks for the introduction.
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It's been quite some time.
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We've been going back and forth and uh we're almost at the uh finish line there.
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Um but yeah, uh as you mentioned, the military.
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Uh so my my time in the military, I was military intelligence officer that was also an aviator, so I flew intelligence aircraft.
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Part of that was uh, you know, there's that you know, going two paths here.
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One is operations, like military folks are typically operations first.
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Um as a commissioned officer, I led organizations.
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I was uh in special operations leading uh you know development of a drone uh unit and asset, uh, all the way to flying reconnaissance missions in Afghanistan.
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But that comes with the operational side, but also the security and uh kind of you know, how do we uh, you know, just the military intelligence side of things, keep a close eye on that stuff.
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So as it relates to my movement into fintech, um, aviation also is a very regulated industry.
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It is very much about compliance for the sake of staying alive.
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Uh finance is much more compliance for keeping people's uh monetarily safe, right?
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And preventing crimes, uh monetary crimes.
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So I think there's there's good overlap between those industries.
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Um, kind of a unique story.
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I was offered a fellowship at a firm for uh uh recently transitioning uh veterans that were trying to find civilian jobs and ended up uh having a unique opportunity to work directly directly with Max Levchin and some of the senior executives over there.
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That was an incredible like growth opportunity as my first job out of the army.
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And then from there um honed my my skills and uh Steven, the CEO and founder of Dub, found me when I was getting ready to go on to my next thing, and uh and that's the story, and now I'm here.
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So uh yeah, kind of a ideological, logical step in the right direction towards this industry.
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We're we're gonna touch on all of this.
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Now you you told me a story when we got dinner recently uh about I may mess it up, but you were flying a very slow aircraft and the headwind was so strong.
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Uh I I could be off, but I believe that you were trying to go across the pond and you had to kind of turn around, but your radio was jammed, so you you had to get some Air Canada plane to tell Nova Scotia that you're coming in.
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I I hope I'm directionally right here.
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Uh what was that like?
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Yeah, so uh the aircraft I flew, for those that know aviation, was like a variant on the King Air, which is a propped airplane that is not designed to fly across the Atlantic Ocean.
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So I was stationed in Germany.
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We needed to bring it to New Jersey, and essentially we had to like pedal jump across the North Atlantic in the middle of the winter to get this thing reset.
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And we were flying between uh we ended up landing in Greenland, which is a unique place to hang out, uh, got fuel and was trying, we're trying to get to St.
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John, Canada, but we had this 110-knot headwind, and you know, when you get to that part of the the aviation world, you actually report on like the crossings of latitude and longitude.
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So we're kind of trying to give the next crossing point that we're about to hit um to uh you know Maine is like it's like the uh the air traffic controller that's like in that region.
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And we couldn't get a hold of him, so we heard an Air Canada flight on VHF, and we're like, hey, can you just let you know the center know that we're we're about like eight hours out to our next reporting point?
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And the the pilot is like, How are you eight hours out from talking to me right now?
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Like, how fast you're going?
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It's like uh ground speed of about a hundred miles per hour.
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He's like, What kind of aircraft are you?
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And we're like, Oh, we're a king air.
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He's like, Why are you in the North Atlantic in a king air going that slow?
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And we're like, uh, we're the we're an army crew, and they're like, he was like, Oh, that explains it.
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And he passed it along with his satcom, but it was uh it was one of those funny moments where you know you're doing something a little bit crazy, but it reinforced the crazy when other airline pilots are just asking you what the hell you're doing up there.
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So uh it was a it was a good venture what are you doing in the cockpit of an eight-hour uh like 200-mile flight?
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Calculating your fuel over and over and over again.
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So essentially, like if it got if it got too windy, if the headwind was too strong, you end up hitting like the point of no return, right?
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So we were constantly calculating manually and digitally over and over again.
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Are we going to cross that point of no return with high levels of confidence?
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Like we we put in a buffer, but like you can never control the environment.
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So ultimately, there was and what's your altitude in this?
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We're I think we were flying at like 30, 34,000 feet.
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Um, so we're up there, pressurized aircraft.
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We're we're playing up.
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And then we were actually also hunting for lower headwinds.
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So when you're up that high, you can actually maybe drop down.
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But here's the paradox: you come down further, you might lose the headwind, but your burn rate increases because engines are optimized at you know higher altitudes.
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So boy, we're going way off topic.
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Well, I'm teaching you about the uh aeronautical uh principles.
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We're gonna we're gonna no fun intended land the plane.
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Uh my final detour here, have you have you seen the show The Rehearsal?
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I have not.
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Okay, I'll I'll pitch you on this offline, but it's a show, a comedic show about uh the relationship of airline pilots, so I'm curious.
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Um but when when you we'll we'll we'll we'll we'll come in here.
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You you're doing you're doing spec you're doing spec ops.
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Um you I I think that what I've taken away from having the the chance to speak with people like you, people like Kelly Deckerson, who who come from an army background, there's this appreciation for ops in a way of I've heard Kelly talk about, you know, he was on a battlefield in Iraq and the tanks were positioned in a way that saved people's lives just because of ops and the training.
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Uh I think ironically, when you go to Silicon Valley, ops are like the people who you have to bring in to to make sure you're staying on top of things.
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Uh could you maybe talk about kind of the appreciation that you develop for ops?
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Because I've increasingly seen as we've grown, ops is actually what makes companies go up a lot more.
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I actually think that ops are the the areas that you didn't even realize that by building this function from zero to one, you will get so much alpha.
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But I think the I I I think it's this interesting thing where it it wasn't seen as sexy versus when you speak to people who are truly flying planes uh and launching drone programs in Kandahar, they'll actually tell you that that ops is the root of everything.
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So uh how how do you kind of think about that?
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Yeah, I think you know, the biggest like so the the typical like thing that people say is like, hey, we're too lightweight, we're too lean to worry about operations right now.
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Let's let's build, let's find product market fit, especially early stage startups.
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They love to tout that they are flexible and they can pivot on a dime.
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And the coming from the military, operations is the lifeblood of the organization because in a large organization, the you know, the military is huge and it's filled with people, and it's it's difficult to communicate.
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In the fog of war, it's difficult to communicate even tactically sometimes.
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So, like, what is the the what are the two things?
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There's actually three things that really tie it together.
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When when all else goes and fails, it's your mission, your values, and the operational overlay, or the SOPs, or the common language spoke through action that ties an organization together and makes them succeed when stuff gets tough.
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And when I'm thinking about a startup, while it's not this giant organization, it is the fog of war.
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That's where I equate a startup to.
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You're in a fog of war.
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You might not always be able to communicate with each other, you might lose slight context at the nooks and crannies of what's going on.
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Something stops happening, no one's covering it, and you don't know what's going on there.
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And that's where I think uniquely, like Stephen recognized as he was building dub, he's like, I want a strong operational culture.
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And like he indexed on that by hiring me early in the trajectory of the company.
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And I think a lot, I'm not saying I'm personally responsible for any of this, but us all being dedicated to what the operational overlay does to the people, the clarity of mission and vision, and the ability to keep a few people doing a lot.
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Like we have hundreds of thousands of open brokerage accounts, we have hundreds of thousands of users, we have a million different things happening at any given moment.
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And without an operationally sound organization of, you know, we're currently only like 25, 26 people.
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We couldn't do that, right?
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It just becomes quickly hazardous, and we've built a stable core.
00:11:07.279 --> 00:11:12.000
And I think another thing to call out here is like operations also is the foundation that you could build on.
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And I think being able to build on this foundation is what's giving uh dub the legs and the ability to kind of navigate market conditions, navigate private markets, navigate fundraising.
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It's just there's a ton of inputs and just having that foundation to kind of pivot off of is really what's important here.
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Yeah, and I'm also trying to like not a number of complicated things too here.
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So that's always another topic that we should probably delve into.
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We we definitely will.
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What was it like going from spinning up drones to uh working with Max Lovchkin uh at a firm?
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What was that transition like?
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What got you interested in that as well?
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Yeah, so I I eventually I started, I was like employee like I think under 200 at a firm.
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It was early, it was 2017, and I knew nothing about tech.
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I knew nothing about startups.
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I was just like, how do I make as much money as I was making as a major in the army?
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And if that checked the block and I got to live somewhere cool like San Francisco, I went for it.
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And I took a huge risk.
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I actually, during this fellowship, I had to like leave my wife in Florida to like help like close up the house and sell it and move it.
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But ultimately, um I realized I got in there, I was like, okay, none of these people are very operational.
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Um I think like, and it kind of gave me an identity crisis, to be honest.
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I I was like this generalist.
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Like I love to I love to comment that people in the military, when you become a senior officer, you become a general.
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And like that term comes from the fact that you become the most senior generalist in the military, right?
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There's a reason behind that term.
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And I think officers in the military in general are generalists, they're an inch deep and a mile wide.
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And I realized there's nobody like that, maybe other than the exec, some of the executives that were pretty like head on a swivel, very clearly understanding all the business inputs, the technology inputs, the customer inputs, and bringing it together.
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So when I looked at this at the microcosm, I was working on like new markets for enterprise.
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And I was like, wow, there's a lot of people that don't know what's going on.
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And I made it my mission to make sure the right people had the right information at the right time.
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Like, that's operations 101, right?
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That's that's building a drone unit, that's deploying to combat.
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It's it's the the idea of building a team of people that have the same mission.
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So when we got like, hey, we want to work with United, there's an RFP out here.
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I was like, okay, let me understand what everybody needs to know, when they need to know it, and why they need to know it, and let me get that done.
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And I and I remember I kicked off like this, like we called it like the enterprise deal desk.
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It started with a whole bunch of reluctant people being like another meeting.
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And in three months, it became like the execs were in the room, and the they were actually like, hey, we need to kick some people out of here.
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Like, this is more of like a high-level like strategy discussion.
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Like, let's limit it to like one person per function.
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And like it be it, I didn't advertise it, I didn't ask people to come.
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Uh, one lawyer hears that it's like they're getting the information they never got.
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Ops found out that from the support side, they were getting like an early read on the new clients coming through the pipeline, and it all synthesized into like this really meaningful function of like information delivery and collaboration.
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And people started getting ahead of the power curve, and we became better at expanding on new markets, right?
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And taking on enterprise clients for the first time.
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So that was a transition.
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It literally went from I don't have an MBA, I didn't have any experience doing this.
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I had experience getting people the right information at the right time and having people work together, right?
00:14:55.360 --> 00:14:57.120
So direct correlation.
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And I like this concept a lot in that I think we often say the constraint, why can't we just hire more engineers or more salespeople?
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It's information.
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It's we we it's only so scalable to train people in the things that they need to know.
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When you think about that transition, is there like a leadership lesson of this is how the army thought about distilling information that you're able to bring to the enterprise deal desk?
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Yeah, I think one thing that I I love and I bug the hell out of people about this, especially leaders, is this idea of mission command.
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And this is army doctrine like 101.
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And mission command is essentially the underlying mechanism for which military leaders distribute and organize the vision of what needs to get done.
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And it essentially consists of a few things.
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One is uh the mission that you have to really clarify the end state mission and goals.
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Um, it's a lot, I always say end state management is the key to execution because it stops you in your tracks from telling people how to do it, but it tells you you're telling them what you want to see done, and it lets them solve it at the most tactical, lowest level possible.
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So, like as a drone commander, is like we need to build, we like for me, it was like we need to provide this many hours of intelligence, surveillance, and reconnaissance over this geography by this date.
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Like that was my commander's intent, right?
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How I did it, there's a million functions, and all the different individual functions will have a way of solving that.
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So, like, you need that to kind of, you know, your end state.
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So if you can clarify the your end state and your vision and then orchestrate that through a shared framework of values, um, that's what mission command is.
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And like you also have to some things, like little buzzwords from the doctrine, it's like you have to be able to delegate uh to the lowest level possible.
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You have to be able to, you need to be willing to take prudent risk.
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And I always, and this is relevant to this, prudent risk.
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It is risk that is acceptable to the mission.
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Uh and you have, and as a commander, that one of the most important things is calibrating your prudent risk-taking capability.
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So what it boils down to is judgment.
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Like you have to have good judgment, you have to have good values, and you have to have a clear vision.
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And if you can communicate those three things and then build in pretty systemic feedback cycles, you win.
00:17:29.200 --> 00:17:31.519
And this is how your radio goes dead.
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Your soldiers know exactly what to do.
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Because they're not asking for what's next, they know exactly what the end state of the that mission is, including we call branches and sequels.
00:17:39.920 --> 00:17:41.839
What happens if we get to the end?
00:17:41.839 --> 00:17:42.480
You do this.
00:17:42.480 --> 00:17:45.440
If we don't get to the end, we branch here, right?
00:17:45.440 --> 00:17:49.920
So these are like very hardcore doctrinal terms that I'm bringing up.
00:17:50.319 --> 00:17:52.640
I I like this concept of prudent risk.
00:17:52.640 --> 00:18:05.200
Uh, you know, you probably see many different types of fraud uh not the attacks, like people who are trying to take advantage of your platform a different way.
00:18:05.200 --> 00:18:09.759
You know, we say if you want to get rid of all fraud, you can just let nobody on the platform.
00:18:09.759 --> 00:18:10.640
It's very easy.
00:18:10.640 --> 00:18:13.680
Um obviously there needs to be some type of toggle.
00:18:13.680 --> 00:18:17.599
How do you think about what is the right level of risk that you take on?
00:18:17.599 --> 00:18:29.359
Obviously, at the end of the day, nothing's in a theoretical vacuum, and everybody's, whether they're aware of it or not, are taking on a form of risk, but how do you actually try to measure that and say this is actually a good risk for us to take?
00:18:30.240 --> 00:18:32.559
Yeah, this is actually one of the hardest.
00:18:32.559 --> 00:18:46.880
Um, this not only to like AML, KYC stuff, risk calibration and is like the heart of what an executive is designed to do.
00:18:46.880 --> 00:18:49.920
Because there's no like hard and fast answer.
00:18:49.920 --> 00:18:55.759
It is completely a judgment call uh based off of experience and knowledge.
00:18:55.759 --> 00:19:12.480
And if you would uh you know, that's why execs wear a heavy burden because they they essentially have to sit there and it goes to business risk, it goes to you know spending on marketing, how much do we want to spend before we get clear like ROI?
00:19:12.480 --> 00:19:16.160
How much, like, how like we don't have attribution, how do we go?
00:19:16.160 --> 00:19:28.640
So ultimately, like orchestrating risk, like first off, when it comes to like AML, KYC, onboarding, compliance, um, it's very important that you don't just look at it through a vet like a stovepipe.
00:19:28.640 --> 00:19:29.920
You're looking across the business.
00:19:29.920 --> 00:19:33.279
What how what is the stance of risk across your entire business?
00:19:33.279 --> 00:19:44.240
And where does this kind of financial crimes AML stack on running out of runway?
00:19:44.240 --> 00:19:46.559
Or you know, we we're an investment platform.
00:19:46.559 --> 00:19:49.599
There's a million other aspects of risk that we have to deal with.
00:19:49.599 --> 00:19:51.680
We're also a registered investment advisor.
00:19:51.680 --> 00:20:07.599
There's we're managing risk across multi facets, but ultimately, when we first were kicking this thing off, um, we wanted To only take on as much risk as we would feel that we are capable of monitoring at any given time.
00:20:07.599 --> 00:20:10.720
So, and I'll break this down more specifically.
00:20:10.720 --> 00:20:20.079
Like, if we were taking risk on who we were letting on the platform, we could only take on as many people as we could manually monitor every day, right?
00:20:20.079 --> 00:20:25.759
And so, as we built better monitoring systems, we could take on more people.
00:20:25.759 --> 00:20:38.400
And then we were like, okay, let's add redundant systems to our onboarding platform to give us an extra layer of confidence that who we're getting, there's a lower probability.
00:20:38.400 --> 00:20:45.200
So, like everything was a mathematical equation of like the probability is going down as we scale up.
00:20:45.200 --> 00:20:56.480
And essentially that's like manual coverage to begin with, automated checking and redundancies, and then there's audits, and then it's essentially um live testing.
00:20:56.480 --> 00:20:58.319
Like now we're we're live for six months.
00:20:58.319 --> 00:20:59.839
How many failures have we had?
00:20:59.839 --> 00:21:01.440
How many known failures, right?
00:21:01.440 --> 00:21:12.960
We have to assume there's unknown failures occurring, but then being able to like quantify the known failures against a known quantity of acceptable like pass-throughs is is where it really kind of honed itself.
00:21:13.279 --> 00:21:14.640
And it continues to this day.
00:21:14.640 --> 00:21:21.519
It's a toggle.
00:21:21.519 --> 00:21:25.039
And by that, or like a I'm sorry, like a a lever.
00:21:25.039 --> 00:21:27.920
And by that I mean you know, some people can view it very much in a vacuum.
00:21:27.920 --> 00:21:36.400
I think this is a pretty fair way to say, you know, hey, like we can move this up or down, but are we a freemium product or are we a subscription?
00:21:36.400 --> 00:21:48.319
Uh or are we letting people deposit with a chime account or Cash App, or are we restricting this to a bank account we linked or something like a card we use with 3DS?
00:21:48.319 --> 00:22:07.599
It also brings into focus this idea of you know risk in Teams from a KYC perspective, uh is a higher level, like can almost be thought of as a higher level conversation because it does directly impact product and the acting kind of product people are leading it.
00:22:07.599 --> 00:22:22.559
Um how crowd, I guess when you think about all those different levers that are in there, how do you how do you try to one approach uh like the way of thinking, like, do you the there's the I'm bad with analogies, but it's the the tail wagging the dog, right?
00:22:22.559 --> 00:22:28.480
Like which one do you how how do you think about like which one should be dictating the other and like how that dance should play out?
00:22:29.440 --> 00:22:31.519
This is a this is a spicy topic, right?
00:22:31.519 --> 00:22:37.200
So we all know that as a startup growth is growth is king.
00:22:37.200 --> 00:22:39.920
It's the primary objective.
00:22:39.920 --> 00:22:55.200
And when I go and say, well, we can't let you know, things like let's raise the minimum deposit, let's make sure that the bank account that they're linking is confirmed to the name on the account.
00:22:55.200 --> 00:23:03.519
Let's make sure, like there's you know, source of funds checks, let's make sure we put a buffer into the minimum account deposits to prevent ACH fraud.
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