Daniel Marini:
Hi, and welcome to CX Coffee Chat. I am your host, Dan Marini. I’m the Vice President of Strategy and CX at Concentrix. And today we have Brett Chereskin, Chief Operating Officer at Dub. Brett, welcome and thank you for joining us today.
Brett Chereskin:
Hey, thanks for having me, Dan. Very excited to dig in with you. Let’s do this.
Daniel Marini:
Thank you. So, could you please introduce yourself and say hello to our audience today?
Brett Chereskin:
Yep, my name is Brett, I live in Manhattan, New York. I’m from New York originally, and I’m sure we’ll get more into my background here shortly, but very excited to dig into the growth of dub and talk a little bit about how things have changed over the last year and a half, two years.
Daniel Marini:
Great, thank you so much for that intro. So now Brett, let’s talk about you, your journey, and of course the main reason that we’re here to talk about is dub. So, I’d like to jump in with my first question for you today. Can you share a little bit about your military background and then how you transitioned out of that career and what led you to your role at dub today?
Brett Chereskin:
Yeah, great question. I think this is probably one of the most often asked questions when someone take a look at my resume and sees 13 years of active duty army experience on it. So yeah, graduated high school and immediately went to West Point United States Military Academy, had a really fun time there. It was tough, but it was fun, very developmental. And that’s where, you know, even starting that far back the elements of organizational leadership, operations, you know, the military is a highly operational place. And that’s kind of where it kind of took birth for me. I graduated from West Point, went to flight school. I flew Black Hawk helicopters and quickly transitioned into fixed wing reconnaissance airplanes and got the privilege of being stationed overseas in Germany. From Germany, I deployed quite numerously to Afghanistan and Iraq areas to operate real live reconnaissance missions. And then I was able to actually met my wife in Germany. So that’s very exciting too. But the military helped make that connection happen. But then I went into unmanned systems. I took on command of a drone unit and got to deploy that. again, all operations planning, execution, support, maintenance very, very rigorous from the operations standpoint.
From there, I grew in my career. I went into special operations. Can’t talk too much about that, but it was an aviation asset organization. And then from there, continued to a really fun experience, which was being a ROTC professor in your home state of Florida, down in Daytona Beach at Emory Riddle Aeronautical University.
Daniel Marini:
Yep, absolutely.
Brett Chereskin:
I was able to take—essentially be the student, exercise operations in combat and overseas—and then be the teacher. And I think that three-part stepping stone of learn, execute, and then teach really helped hone my skills as an operator and a leader. I think if you ask anybody, what is a military officer above all else?—they’re a leader, leader first. I bring that to my civilian career, and it’s one of the most important tenets of who I am and what I represent.
So, as I was getting to the end of my military career, I ended up with an eye situation which prevented me from flying. And I was like, You know what? I need to do something else at this point, because I didn’t want to be in the Army and not be able to fly.
I applied for a fellowship opportunity for active-duty veterans and got accepted. It happened to place me in SF—in San Francisco, Texas. I started at a place called Affirm, the buy-now-pay-later company (AFRM).
Back in the day, it was hard to explain where I worked, because everybody was like, What firm do you work at? And it was small back then—yeah, they always thought I was a lawyer. So I was like, Okay, no, I’m not a lawyer.
I started there in a diversity and inclusion role, helping organize and program-manage the diversity committee. Then I quickly got snagged up by the Enterprise and New Markets team, and they asked me to help operationalize their go-to-market strategy and execution.
From there, a really cool role I got the opportunity to do was Chief of Staff. I ended up being Chief of Staff to the COO—the ex-COO of Groupon. That ended up being a really unique opportunity to, again, condition me for civilian operations in a way that I didn’t get in the military.
It culminated with me becoming the Head of Business Operations for Affirm. At that time, we were taking the company public—which was, again, another really exciting opportunity to witness firsthand, to be in the room where it happened as a Chief of Staff and business operator at the executive level, and really kind of glimpse into the realm of what it takes to scale a now-large business as it grew.
After about four and a half, five years there, I got a little tuckered out, and it was time for me to move on. I was going to take a year off and just kind of reset, but a unique opportunity in New York came up. Steven Wang, founder and CEO of dub, reached out. He was a young founder—it was a seed-stage company—and he was like, Brett, your résumé looks good. We’re looking for strong leadership capabilities. Would you like to come to New York to interview?
And I was like, No.
I don’t want to go do this all over again. I just got done with this grind.
But the more I talked with him, the more he was able to really dig into the purpose and mission behind what we’re trying to do here. He talked a little bit about the investor base—in terms of the angels and institutional investors involved with dub—and it all started to really make sense. And, you know, I said yes.
That was in 2022, and it’s been an exciting journey ever since.
Daniel Marini:
Well, first of all, it’s a hell of a résumé, but on behalf of the Concentrix family, thank you for your service to this country. And I’ve seen Steven in action—I can imagine he’s a hard person to say no to.
Brett Chereskin:
Very convincing, absolutely!
Daniel Marini:
So I can understand how you had to cut that year of rest and relaxation short to join this.
So, dub— and for those not familiar with dub—could you tell us more about it? What exactly is copy trading?
Brett Chereskin:
Yeah, so dub is a really kind of innovative app where you can come on—similar to Robinhood—and create a brokerage account. The difference we have versus a typical trading app like Robinhood is you’re not just trading stocks. What you’re doing is looking through the portfolios of other people and making a decision to copy those portfolios and strategies.
There are a few different types and categorizations of strategies. Some are offered through our registered investment advisor, some are through our creator partners, and others are entirely peer-to-peer. So let’s say you have a friend who’s really good at investing, and you’re like, Man, I wish I could follow their trades—but I don’t know when they’re trading or how to do it, or what platform to use. dub offers a meeting point—a socially connected space for friend groups, family groups. We’ve seen people managing their parents’ portfolios, and parents managing their children’s portfolios. It’s a really unique space.
Another area it’s tapping into is the creator economy. Now we have folks coming from Seeking Alpha or other kinds of publishing platforms where they share insights—and dub lets them put action behind it, which is actually reinvesting.
So, we’re really excited to build this creator economy on top of retail investing, and to see where we can take it from here.
Daniel Marini:
So, as the Chief Operating Officer at dub, you’re responsible for making the machine run. What would you say are your primary responsibilities?
Brett Chereskin:
Yeah, I’ll caveat this by saying that being a Chief Operating Officer of a startup—at the seed stage or Series A stage—is a very different version of “Chief Operating Officer.” It’s really Chief Get Stuff Done Officer, quite frankly.
What I do on a day-to-day basis is not what I imagined it would be going into this role. I really do touch everything.
One of the biggest responsibilities is customer support. Since our company also runs a subsidiary that includes our advisors and broker-dealers, the scrutiny and level of regulatory requirements are much, much higher than with a typical social media app. So we spend a lot of time there. Me and the Chief Compliance Officer are attached at the hip—making sure we’re doing everything right by the customer, and that every cent counts. We need to ensure trades go through properly, that KYC (Know Your Customer) is happening effectively, and that we’re meeting regulatory standards.
Another big part of my role is running finance. That includes modeling, accounting, paying bills, managing vendor relationships—it’s a lot of work just day to day. There are a million personalities, vendors, and relationships to manage. We have to make sure we’re paying them on time, they’re paying us on time, and so on.
Then I’m also running analytics and business operations—monitoring growth, spend, marketing efficiency, all of that.
I also run HR. So, anything related to recruiting, onboarding, pay, benefits—I handle that. And that overlaps with IT too: making sure people’s computers have the latest antivirus, new hires have their machines, and so on.
I know I’m going on and on here, so I’ll shorten it up—but yeah, it’s a lot of things.
Daniel Marini:
Yeah, it sounds like you have a lot of time on your hands. Is that it? That’s all you do?
Brett Chereskin:
Yeah, hahaha. And partnerships! I help support go-to-market efforts on the partnerships side as well. For some of our creator partners on the app, we’re managing very bespoke partnerships—which has been a lot of fun.
Daniel Marini:
So when it comes to focusing on your customers, your role literally touches every part of that customer lifecycle. How do you prioritize customer experience when you’re also managing growth, cost, and product delivery? Can you share a moment when CX had to take a front seat, even if it meant short-term sacrifice?
Brett Chereskin:
Yeah, one thing that really stands out—we were in a board meeting mid-last year. At that time, it was just me and our Chief Compliance Officer handling every single customer support ticket. No agents. No support team. Just us.
They asked, “How many tickets are you both doing?” And the answer was about a thousand tickets a week—while also managing all our other responsibilities. He’s also our General Counsel, managing legal and compliance for our advisor and broker-dealer. I was handling HR, operations, finance—you name it.
But we were committed. We told the board: If we don’t feel the pain our customers feel every day, we won’t make the right trade-off decisions on product, roadmap, or engineering prioritization. I really sacrificed my own well-being for about a year and a half to stay on the front lines.
If I saw a design change causing friction, or an outage caused by a bug—or just something that wasn’t doing right by the customer—there was no, “Let’s table this until Friday’s product meeting.” It was, “CEO, Head of Engineering—we’re fixing this now.” Immediately.
And that paid off. Early on, our scale was modest. But by the end of last year, things scaled fast. Because we’d built resilience—into the product, into the support process, into the entire customer experience—we were ready. I’ll always be grateful we laid that foundation.
Daniel Marini:
Well, all those early moments of grind seem to be paying off. And I know last month, early May, you guys announced some extremely exciting news—you closed a $30 million Series A. Congratulations! That kind of milestone signals serious momentum and unlocks new opportunities. So how are you thinking about scaling thoughtfully—preserving your company culture internally and maintaining a high-trust experience for your customers?
Brett Chereskin:
Thanks! One thing I learned at Affirm before this: When you close a round, it’s tempting to immediately ask, What can I invest in? Who can I hire? But we’re being really intentional about this.
We asked: What’s the best thing we can do for the user and for the product with as few people as possible? Because as we discussed earlier, feedback loops inherently get longer the more people you introduce into the process.
So I ran an exercise: I went to each exec and asked, If money wasn’t a limit, what would your ideal headcount look like? We built a “dream plan,” then we waited. And after the round closed—well, we already saw it coming—we said, Alright, let’s walk that back. What do we absolutely need?
We’re also operating in a time of rapid innovation in AI. Some big companies are struggling to retrofit AI. We’re in a unique spot—we can integrate AI strategically from the ground up.
We’ve been pushing, from the executive level to every team member, to ask: How will AI make you more effective? How will it reduce our need to grow headcount without compromising business needs, human needs, or work-life balance?
As a result, we’ve reduced our expected 2025 hiring plan—from 20 roles to just 4. That’s a huge shift, and it’s thanks to what we’re doing with AI across all functions. It’s been incredible to see what’s possible.
Daniel Marini:
Awesome—thank you for that. My next question is about your users. Many of them are also creators—they’re engaged, vocal, deeply invested. Was there ever a time, especially in the early days, when their feedback challenged your roadmap or forced a shift in your strategy?
Brett Chereskin:
Absolutely. In a seed-stage startup, you have to think in two streams:
Some companies build for what customers don’t yet know they need. Others build exactly what customers ask for. We wanted a hybrid approach.
On dub, to create a portfolio, you have to be a brokerage customer—you need an account, do your own trades. And right now, we’re mobile-only. So creators and users experience the same interface.
We had to deeply listen to those early creators—the ones who took a chance on us—because ultimately, we’re a marketplace. And in marketplaces, there’s always that chicken-and-egg problem:
Do you build supply first? Or demand?
In our case, creators are supply. Retail investors are demand. We needed both—but more importantly, we had to sequence that growth correctly.
We chose to focus on the investor first. Why? Because trust is everything. We were a no-name startup asking people for their Social Security numbers, birthdates, income—real personal data. That’s all required for compliance (KYC, AML), but we had to earn their trust quickly.
So we obsessed over onboarding—making it seamless, making it human. We added helpful modals to explain why we needed that info. We made it feel safe, easy, and smart to open an account.
Once we did that, we saw retail demand grow—and then creators followed. The flywheel got going. And to jumpstart that interest, we built out high-interest portfolios through our registered investment advisor: the “Pelosi Portfolio,” the “Warren Buffett Portfolio”—portfolios that tied into the cultural moment and got people talking.
Once users saw real capital flowing on the platform, creators started asking, “How do I get involved?” That was our journey—and now we’re about to launch even more exciting updates.
Daniel Marini:
I remember the first time I talked to you—I literally hung up, went straight to the app, and opened my account. And it’s funny—my daughter just turned 18 on May 23rd and said, “Dad, I want to start investing in the stock market. How do I do that?”
I said, “Well, start on dub.”
She’s 18 and doesn’t know what she’s doing… and I’m 53, and I still don’t know what I’m doing in the market!
Brett Chereskin:
Yeah!
Daniel Marini:
And that’s the beauty of dub. Like, you know, you’ve got to leave it to the experts. You do that with, you know, your health care and your building homes and things like that — which, you know, Steven talks about in dub’s mission. It’s perfect for young investors.
But back to my questions. I only have two more for you. You know, dub lives at the crossroads of FinTech, creator economy, and social platform. So, what shifts are you seeing in customer expectations, and how is dub positioning itself to lead rather than react?
Brett Chereskin:
Yeah, I think one thing that we’ve seen is — especially in, like, we have a predominantly Gen Z/millennial kind of user base — so we have kind of a unique position here, where traditional finance is kind of more millennial, Gen X, or Gen… yeah, Gen X and even boomers.
And I think there’s a generational gap or change. We’re actually about to do this big research project right now. We’re doing a poll to, like, thousands of people to figure out some of the differences in: what is financially free? What is your expectation of retirement?
Because I think your expectation of retirement is materially different than that of a 21-year-old right now — and how you get there is very different. I think a lot of the Gen Z, and even younger millennials, want to participate in not only the aggregation of wealth from things like jobs and side hustles — and, like, you saw this through COVID, the side hustle economy, right? Like, everybody is doing their day job and then also another job.
And all that capital needs to go somewhere. So now they also want to have a third aspect: of really being in control and having oversight of how that wealth grows. And I think, even me to an extent — you know, I just turned 41, you’re in the 50s —
Daniel Marini:
You don’t have to rub that in.
Brett Chereskin:
You know, we’ve been trained — yeah, well — we’ve been trained: hey, you know, go get a financial advisor, park your money with them, they’ll figure something out, and just nod your head yes, and pay the fees, and you’ll be done with it.
And I think this new generation is very much like: I want to have transparency on what’s happening. I want to have personalization that makes sure it’s happening in the right format for me — not just for my cohort.
And I want to use it as a form of community, and entertainment, and engagement. I don’t want to just set it, forget it, and check back in next year.
We’re seeing our users come back three times a day, spending a few minutes just kind of seeing what’s up, reading our feeds, understanding the rebalance notes when our creator rebalances one of the portfolios.
And even while they’re not necessarily taking action beyond “what do I want to invest in, and how much do I want to invest in,” they like to understand the why.
And I think our app gives a unique opportunity to provide the why for folks that are interested in it — while also giving people the ability who want to just set and forget it that option too, right?
So we have some users that set and forget and walk away and come back in a month and see how things are going — that’s up to them, right? We have notifications; they get the rebalance notes when they happen. But others dig in and really want to be involved and build a community.
And that’s where we’re moving with this. Like, we really want it to be a community. We want it to be an area where positive discourse is happening and exchange is happening.
It just needs to be very careful about how that works through the financial world to make sure it’s beneficial for everybody.
Daniel Marini:
Absolutely. Thank you for that. My last question — it’s a layup: just any last piece of advice that you would like to share with the audience today?
Brett Chereskin:
Yeah, I would say — especially through the CX side of the house — if you’re ever angry at an app you’re using, and this is somebody who’s gotten beaten up for the last two years, put your… you know, just think through it.
Think why. Like, you’re probably dealing with a concentric agent or somebody — everybody’s in best interest here. And I think my advice here is: as you navigate kind of new apps and new ideas — and us being an early-stage startup —
Hey, A: leave. Like, I think it’s awesome if you’re an early adopter. And B: be flexible and really dig in, and really kind of explore the left and right limits of what these new technologies have for you.
One for me is AI. Like, I needed to push myself out of the comfort zone and get into it. And it has paid in dividends — what I can do personally for this company, and what I can do for the users, and what my team and the team of everybody across the business can do to innovate and really provide the best possible experience as quick as possible.
Daniel Marini:
Well, I think you’ve covered the dub story so well, but I would be remiss if I didn’t share the dub mission, as written by Steven Wang, because I thought it was so well done.
The mission says that 40% of Americans don’t own stock, and the 10% wealthiest Americans own 88% of the stock market.
It’s like — I had to repeat that: the 10% wealthiest Americans own 88% of the stock market. Most Americans haven’t — or haven’t equally — participated in the greatest wealth creation engine of our times. Why?
Because investing is hard. Stocks are confusing. And picking the right ones? Even most full-time professionals get it wrong. The wealthy figured this out long ago. They don’t try to pick stocks themselves — they pick people to invest for them: hedge fund managers, star investors, experts.
Because, as with all difficult things in life, you don’t do it yourself — you trust the experts. Just like you do with a doctor, a lawyer, architects. And here’s the secret: we’re actually pretty good at picking smart people.
You know it when you see it. You feel it when someone walks into the room. It’s human nature.
dub is giving everyday Americans the same edge the wealthy have always had — through copy trading. Power to invest by choosing great people and investing alongside them automatically.
This isn’t just about simplifying investing — it’s about transforming it. Moving from stock picking to picking people changes the entire playbook, unlocking access, participation, and ultimately, opportunity for all.
If we get this right, dub won’t just be a new way to invest — it’ll be the beginning of a more equal and more abundant future.
Join us. Let’s build wealth together.
Sincerely,
Steven Wang
That’s it. That’s the microphone drop.
So that wraps us for today. Brett, I want to thank you on behalf of the Concentric family for joining us today. And as a partner of you guys, we wish you the best of luck for your continued success.
And thank you all for listening. This was CX Coffee Chat — and thank you for your time!
Brett Chereskin:
Thank you. Thanks so much for having me.
