YouSaid · the spoken record

Jason Wenk

lines on the record: 80
first: 2026-07-17
most recent: 2026-07-17
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“We wrote the first lines of code in January of 2019, and I think we went into beta in early 2020 and then launched the product right in the heart of the pandemic in 2021.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“You can then upload that to our system. We'll then debit those fees from the accounts. But this whole process can take days. And by the time you go to debit those fees, sometimes a client will have had a distribution in their account or a trade or something. And the fees get busted. It creates an account that gets overdrawn. Just fundamentally, again, there's hundreds of these things. And you go, this makes no sense. Like, why is this the way things operate? This is largely the genesis to why would you build a brand new custodian from scratch? And if you are going to build it in a modern way, you would probably make sure all of these things are just built in automatically.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“That third party will reconcile all that data and it will then allow you to run reports for your clients. And you're going to have to pay, you know, depending on the size of your firm, anywhere from tens of thousands to millions of dollars for this third-party software. And this just fundamentally makes no sense at all. The custodian has all of the data. It should easily be able to reconcile that and run reports for advisors, but they can't and they won't. And you could go down this long list of things that they should be able to do, again, just like the logic would tell you, for example, If you want to bill a fee to your client, client signs a fee agreement says, I'm willing to pay my advisor 1% hypothetically. And I'm willing to pay them that every quarter by calculating the average daily balance and bill me in arrears, right? Something simple. Custodian will say, that's cool. What you need to do is we'll send you the data to a third party. They can reconcile the data. You can then run a billing schema. It'll create a C.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Somewhat. I mean, or it could be a built in limitation, keeping that advisor from doing high quality work, right? Which is, I think, what I sort of discover as I kind of peel back the layers of the onion. So these custodians, one would think a very simple thing they should be able to do is let's say you have three accounts with your financial planner. You've got an IRA, maybe a Roth IRA, a joint account with your partner, and you want to know how am I doing over the past 12 months? You'd think you could just log on to Schwab or Fidelity or Pershing or whatever and just click a button or something and it would tell you that. But the reality is that you cannot get that information from your custodian. The custodian will only be able to tell you what you have today. It will give you access to your statements. The statements are not bundled at the household level. And what the custodian will tell you is that if you want that type of information, you need to buy a third party portfolio accounting software. We'll send them a daily file of all of your positions and transactions.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, exactly. You're right. It doesn't mean it's the right way. And so, some examples of that, I think it's a bit crazy that if you're a financial advisor or wealth manager, and I think if someone's listening to this and they're not one of those, they'll think this is literally crazy. This is the way it works. But so first, you have to have a custodian, right? And this is a place where you'll open accounts for your clients, they'll safeguard your client assets, do all your record keeping processing. Rusted third party who...”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Having been in this space a long time, for the longest time, I would look at the industry and I'd go, that just doesn't make any sense. Why do we do it this way? We've always done it.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, they're still fun to use, you know, the click and they make a nice noise, right? It feels very, you know, it reminds me of my grandparents' house in the 90s or something, you know. So look, I think getting to the problem statements.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“It operates on mainframes, not cloud native platforms. So I think the starting point is, and with no disrespect, these were innovative companies 50 years ago. They're just not that innovative today. So as far as I get used to saying.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Type of industry. Yeah, well, I guess, you know, the opposite of modern is not modern. So the whole rest of the industry is pretty old. If you think about most of the infrastructure that's used by financial professionals, the majority of it's 50 to 70 years old. That's amazing.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“The place that seems to be growing the fastest. That was crystal clear to me 20 years ago. And I think a lot of that comes from just, again, that more first principled sort of Silicon Valley way of seeing the world.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, it was maybe $600 to $800 billion in assets today. It's probably $10 trillion. So today it seems very obvious. But back then, it was a relatively small part of the market. It was not obvious maybe to everybody. But I look at the demographics of the country and just there'll be such a huge number of people who are going to need good quality advice and planning. And that just, again, if you think in first principles, which is a very common technology metaphor, and you have no bias of the way things had been done historically, to say, well, what is the right way to do things? That just seemed like the obvious and only an objective future for this industry. And I wanted to be, you know, in the forefront of that. So now, you know, some 20 plus years later, the market is very obvious to a lot of people they want to build in the space.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. I mean, look, I think I've always been a little bit idyllic. You know, you name your company altruist. You probably have some generally idolatrous tendencies. I think people who know me well. They would say I'm a bit of a macro thinker, but I don't like working in the day-to-day weeds of most things. For me, I've always thought in decades, and it wasn't hard to look at the market in the early 2000s and say, well, this is the future. Even though, to your point, like the RIA.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“That seemed a lot better, right? So, yeah, so just the idea was spawned, hey, maybe it makes more sense to license the software, make it easier for people to run their own business, but leveraging a lot of our technology. And that was the form.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Post, here's the framework how I do it, here's how I take these people then through from a stranger from the internet into a defined financial planning process and then a defined portfolio and it was so structured that I could then train other advisors and so I hired a few other advisors they came out they could then run the process And so that was the content And at that time a bunch of other advisors, I'd say hundreds of other advisors started to reach out inbound hey how can I get access to your system they would kind of call it and the reality was like I didn't want to hire 50 financial planners I've always been a bit reclusive so I didn't want to You don't want to manage 50 people but selling them the software”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Proposal systems to help really analyze a portfolio and then propose a new solution, digitize a lot of onboarding to really automate getting new clients onboarded. And it was mostly virtual. So it was also before its time in the sense that it was built mostly from blogging back in the 2006 to 10 era. So it was a lot of things it was doing well before its time. And what ended up happening really the catalyst to moving into the next business was I was invited to speak at TD Ameritrades National Conference. They were my custodian at the time. Loved the people there. They saw the unusual growth and also that I was still in my 20s and they thought, hey, we'd love to have you come speak and share a bit how you're doing what you're doing. So I went to San Diego, gave a session where I just said, hey, here's how I'm getting new clients. I'm writing these blogs.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I was always driven probably more by impact than by the size of assets or a revenue that company was bootstrapped. I built every single thing myself, wrote all of the code. Although the name was retirement wealth, it was a fairly tech forward platform I built my own.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Where did that go? Yeah, so I ended up going to about 1.1 or 1.2 billion in assets. Yeah, it grew really fast. I started it in November, December of 2004 was when I got my registration, ran that for about six years roughly.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“I started asking people, well, what would be more valuable? Sort of like a churn survey, if you will. And people would say, look, if you would just do this for me, I'd pay you a lot more than 20 bucks a month. That was really the genesis to retirement wealth. And that's even why it was called retirement wealth, because a lot of these 40k folks were retirement folks.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“So, look, the pay-per-click advertising was just coming out. So you had things like overture, which was like kind of pre-Yahoo, pre-Google. But you could buy the keyword for something like a phrase like how to manage my 401k for a penny, right? And you could be the top ranked search. People then land on my website, which is called Smarter Than Wall Street back then. And yeah, and it would allow you to say, I work at General Motors, answer a few questions, and it would say, here's how to allocate your 41k. They'd get an email once a month if there was anything they should do differently. Of course, the email never said I should ever do anything differently. And after about a year, I built a pretty good size subscription business, but I started to have some churn because people are like, why am I paying you every month to just send an email that says the same thing as the email the month before? And eventually.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah, yeah. So 2001 till 2004. And it was honestly like when I look back at it, it was just kind of like maybe a little bit too early. This was like pre-RoboAdvisor pre-blogging, like pre-lot of things that just got more people connected.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“And I could see the direction the internet was taking us to really flattening the world. Like everybody should be able to find advice and help through the internet. So really the first business was from an accessibility perspective, it was going to be internet-based. It was a subscription service. And it was designed for people with 401ks because when I looked at the people I knew, that was about the closest thing they had to Wall Street to a brokerage account was their defined contribution plan. So the idea was let's make it easy for people that have a 401k plan to get the absolute best results they can from their 401k. And I spent about almost three years building that business. It's not on my environment, wealth advisors? This is the one that doesn't exist on my LinkedIn profile.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, and also, I mean, I looked realistically at the way asset management worked, and I thought I very much agreed with the Morningstar study that they published, he said some 10 years later, a lot of this, I'd say, goes all the way back to Jack Bogle's work, but I just looking at a couple of years' worth of research around asset management, I didn't see a discernible benefit to stock picking or market timing. Again, high costs, high turnover, high taxes, like these ones all eroded wealth. So part of me, well, is there a way that you can just get more people access to empirically sort of evidence-based investing? Maybe that also help people do better. The other part was accessibility. Again, I grew up like in a farming town. Really, there were no brokers. There were no bank advisors. There were no Edward Jones offices. There was really no access to advice.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, so two things in particular. I mean, one was around that time, there was a transition from commission-based sort of sales brokers, if you will, and there was a transition to more fee-oriented financial planners. And for me, that really resonated. So I think this notion of, hey, can you give people more comprehensive planning advice?”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“I had this romantic notion of going back home and helping people that I knew through there's nobody I knew any money, you know, so like that wasn't really going to work anyway. And really before I even got started, I made the decision to leave and go start another business. I'm kind of in the space but adjacent, didn't do direct work with clients.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah, I'm not sure why I also registered options principal. I did that. I have no idea. Manage futures. Like, again, not sure why I did that. But yeah, I did all of the research. To understand the space. And I did go through the broker training program sort of 2021. And part of it was because I wanted to move back to the Midwest.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Right there. Exactly. There's something with it. Yeah, yeah So I got licensed. I took the Series 7, Series 8, Series 24, Series 30, like all the classic licenses 24.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Pre built prompts inside of these research platforms. And again, the way my mind worked, which was more around math, physics, computer science, I looked at these prompts and I thought, these are terrible prompts. In other words, the prompt would be, let's build a screen so that financial advisors can easily build a portfolio. The screen will be something like find funds that have been around for five years with turnover under 100%, with the same manager for the five years or longer. That's in the top quartile of their peer group. And on the surface, you go, well, it seems like pretty reasonable and fair. But that has no prediction of the future result. a terrible predictor of future outcomes, but it was sort of built as though it was a good predictor. Well, you have the.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Was Yeah, I was still working in technology, so my role, the internship was like productivity software, but again, just happened before a big investment bank. And then I spent about two years building different types of technology, like within the Morgan Stanley ecosystem. By the time I joined, they were Morgan Stanley, Dean Witter, so they had this kind of big retail wealth business. They also had like prop trading and a number of other divisions too. So I didn't really get too involved into personal wealth until kind of the latter, maybe the last six months I was there. I was put on a project where doing a lot of work with Morningstar, which back then they were still sending out CD-ROMs to branches around the country. And so, you know, if you had a big branch, it'd be hard. Who had the CD-ROM? So we were just building networked versions of essentially the Morningstar database. But I remember around that time, you know, I was doing some like.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it was presented an opportunity to move here to New York and to join Morgan Saley, and that was really my crash course in finance.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, yeah. No, so I'd never taken a finance class. I never met anybody who had money. My family never owned any stocks or mutual funds. I didn't know what an IRA was or even a 401k for that matter. But I grew up in the 80s and 90s. So I remember getting our first personal computer in the mid-90s. Internet started to pick up a little bit of speed in the late 90s. And that was my dream was to go to Silicon Valley, work at a dot-com. You probably recall the market peaked out around 1999. And then a pretty major crash ensued. So very accidentally did an internship at Morgan Stanley at 19 years old. I was a bit of an odd duck in that I took a lot of college classes when I was in high school. So I was already taking doing internships my first year of university.”
2026-07-17 · Masters in Business · Challenging The Titans of Asset Management with Jason Wenk · IDENTIFIED FROM THE TRANSCRIPT · source