How Brent Sullivan became the go-to tax man
The motto of the independent analyst who endeavored to explain direct indexing to the industry: Give it all—content, tools, everything—away!
Two years ago a self-described tax nerd—whose resume included working on PIMCO’s trading floor and developing software for Parametric as well as a stint as a venture-backed founder—started posting about tax topics on social media. His big swing was his attempt to map direct indexing providers.
Direct indexing is a fast-growing space dominated by the industry’s largest brands, and it’s complicated. Despite a surge in provider partnerships and alliances announced by Vanguard, BlackRock, Morgan Stanley and J.P. Morgan, among others, nobody—not the media and not the brands—was making an effort to explain the array of what was available to the advisory community.
So, Brent Sullivan took the task on himself. A man without a website at first, he started posting his perspectives to LinkedIn exclusively, posing questions and engaging with commenters that ranged from asset managers to fintech providers to financial advisors. The exchanges made it possible to witness the industry openly think through and challenge direct indexing’s appeal and practicality. Sullivan-facilitated conversations have since broadened to include Section 351 ETF conversions and tax-aware long short.
Sullivan created a genius tagline to describe his business’ unique offer: ”Where source code meets tax code.” Today he:
Posts three times weekly at taxalphainsider.com (a substack newsletter)
Runs ADVDB.co, a monthly update database of investment advisers
Continues on LinkedIn, where his 6,000 followers are among the leading tax and product development professionals in the industry, and on X as TaxAlphaInsider
Our conversation focused on how an independent tax analyst asserted himself into all things related to taxable portfolio strategy. The transcript was edited for length and clarity.
Crowdsourcing the direct indexing map
Q. Brent, how did all this start?
A. On Labor Day of 2023 I decided that I would establish myself as an independent voice in this arena. My thought was that I could identify product opportunities to build myself, having coming from an investment management and venture capital background. I kept on digging and I realized that the bench of products in this space is quite deep, much deeper than I thought, even though I came from the industry.
So, I just said, “OK, whatever, I'll start making these [direct indexing] maps and I'll share the maps just to establish credibility on my end as an industry analyst. And, they ended up being way more popular than I could have foreseen.

I think there are two reasons for that. One of them is just that they help keep straight all of the players in the industry because there's no consolidated database. So the maps are essentially a database.
And the second thing is that whenever someone gets left off a market map, their blood starts to boil little bit or they feel left out. It's very painful for somebody to get left off. And so, from a social perspective, it's very high engagement as in, “Did you hear about this? Ooh, ooh, what about this name? No, this one should be recategorized.”
It gets a lot of conversations started, for better or worse. I'm taking it on the chin for the rest of the industry.
Q. So, you were crowdsourcing changes—there was no data underlying where you were placing the providers, is that right?
A. Yep. My tolerance for looking silly is much higher than the rest of the industry.
I think if you're protecting a very large brand, you have to be very careful with those things. But as an independent analyst who's running out in front of the market, I have more flexibility than a big brand.
That cuts both ways. Occasionally I'll get folks who will call me out. They'll say, “No, that's missing some nuance that you hadn't considered.” And I'm like, “that's really interesting. Then I'll just write a whole blog post about that.
But also there are people who say, “Wow, you know everything about this.” And I’ll explain that actually I stepped in *****, somebody called me out and I ended up learning it way better than even they did.
And, by the way, I'm not selling anything and so now everybody calls that influence. My reaction to that is OK, but essentially what's happened is I've gotten hit in the face with a rake just a ton of times and I think not everybody's willing to do that. That's why there isn't an infinite number of influences because not everybody's willing to take that risk.
I have a tiny following on Twitter, but Twitter is brutal in some ways. They'll just say, no, you're wrong, you're stupid. My reaction is OK, that's interesting, tell me why. LinkedIn is cordial. To a certain extent, I'd say the quality bar is much higher.
Taxation gives independent advisors an edge
Q. Would you say that you’ve been an influence on advisors on taxation?
A. I think people ask a lot of questions about how they should be managing money now. They're changing the way that they think about making investment decisions. I would say that I'm bringing a level of tax awareness to the portfolio design question that people had not thought about as aggressively.
The tax world long short stuff that I'm writing about is a game changer. Another game changer from the ETF world is bond ETFs with no bonds in them that are just accruing and not distributing so really hyper tax-efficient bond ETFs. These are fundamental changes in how people manage money.
If you're looking for channels for influence, I would say it's really manifesting in the independent advisory space. That’s because they have a lot more flexibility to adopt technologies that are not investment committee-approved. That community is very eager to look for differentiators from the wirehouses. They say, “Oh, can I do things that the wirehouses cannot do?” “Absolutely. Yes, yes, 100%.”
It will take the wirehouses years to find partner products that they're comfortable distributing or to get all their sales staff up to speed. All that takes forever to get that into place. But the independent advisor channel doesn't care. They're just like, whatever, we'll do the best thing for the client today.
And then they ask, well, where do I learn about the best thing for the client? Well, one aspect is taxation. “OK, I'm gonna read this guy Brent's thing because he puts out three blog posts a week and it's all pretty detailed stuff that's directly targeted to me.”
Q. How literate are advisors on taxation issues, if you were to give them a grade?
A. Full bell curve. Some folks who've just made up their mind about taxation of a certain product and they just do not care to do any additional work on it. So all the way from completely illiterate to who know more than me.
I'm probably talking about a lot of stuff that people haven't even considered. So that would put me ahead. But there are certainly advisors out there who know more than me.
Advisors and vendors will show things to me. But then I do my own work and oftentimes I'll surface things that they haven't thought about.
Part of what I've done, if anything, is to get all the people who care about this particular flavor of advisory to raise their hand. Corralling them is interesting. It’s like, if you follow Brent, you must have an interest in this stuff by definition, because otherwise why would you?
Q. Yes, you’ve aggregated the interest. What’s so interesting about that is somebody could try to draft on what’s you’ve aggregated—you’ve created an audience to target to.
A. Yeah, somebody could sponsor my newsletter, for instance. You could pay for ads on LinkedIn to a generic audience of titles or if you're selling a tax-aware product, you could sell it through me.
I charge for my blog. I make decent money from people paying for my content. So it must OK.
I think people don't want to own my work. That's why they don't want to sponsor it. They’re not going to give me a blank check because they’ll know that Brent's going to do whatever he wants because I am, in some ways, a loose cannon. I will write critical takes of a product. I'm not trying to disparage anyone. I'll just provide more nuance around the investment.
Q. But if I'm an advertiser and you’re controversial, that just means more eyes seeing my advertising.
A. Tell a brand that, they're not taking my word for it.
This is a very, it's a very touchy, very delicate world. Everybody is afraid of looking foolish. Here's the secret: If you say something foolish, delete it, take it back and do it again. In the process of taking it back and doing it again, you get a lot better. A lot of people aren't willing to do that.
I'm sure there are people out there who think I'm a total Ding Dong, but all I can do is do analysis and write reports three times a week. But how could someone who goes through the process of writing and creating be so dumb?
Q. And for you personally, what’s been the effect of being an influence on taxation?
A. I've learned a lot through working with brands. I spent pretty much all of 2024 acting like a marketing product and tax research consultant for a bunch of brands. And so I got to learn their products deeper than I thought I already did. My reaction was that there's more nuance here that you are trying to communicate, but you don't know how.
I felt like I got even a layer deeper. And now my clients are, I would say, an order of magnitude even larger.
And so now I see everything and people will proactively send me products. If I have an edge as an independent analyst that other people don't have, I get to see everybody's products. 18 months ago, it was all from the outside and now it's quite a bit from the inside. And also I have access to almost everyone. I just have some advantages now.
Q. Reconcile this for me, you say you're an independent analyst but at the same time you work for brands?
A. I understand your question, isn't there a conflict? Aren't you going to go soft on your clients? It sort of depends because you're right. I'm not a journalist per se.
When I work for a brand, it's usually in an advisory capacity or I'll be helping them with messaging. It’s their words. I'm just helping them use the right combination of words.
I have my clients I try to stay away from in my writing. Part of my value is that I try to be very even-handed but my north star is trying to get the best information for the advisor.
If one of my clients has the best information. then I will surface it. But if my client does not have the best information or the best analysis or the best visuals, the best of anything, it's not my job to call them out. They will just get the cold shoulder. I'll just say, “Essentially you're not doing anything interesting to me. And if you care about me talking about what you're doing, then you should have to appeal to me.”
I feel like I'm sort of like a connoisseur in this space now.
Q. So, you see yourself as sort of a proxy for the advisor?
A. Yes, exactly. I pretend I'm wearing that hat. I'm trying to channel that persona, to use product speak.
Advisors are being bombarded with sales pitches from a dozen firms at any given time. And they’re asking, “How do I make sense of this?”
Because taxation is so complex, it's easy for a vendor to give their sales pitch and the advisor says, “I guess that's right. I'm out of time to analyze that myself or I don't have the background or interest to analyze that so I’ll take the vendor's word for it.”
My reaction is “Oh no, that's oftentimes just a part of the story. There's quite a bit more context and the vendor won't tell you that because it does not [support] their sales.”
What I do is try to get all the context around any particular product, like why would you even consider this product? What are the trade-offs? And oftentimes you just don't get that from the vendor.
I think advisors are very interested in that because it allows them to outsource work to me.
Q. Would you say you’re covering the space to an extent that traditional media has not?
A. I think private wealth has always been sort of boring for traditional media and so it's not very clickbaity.
Financial services coverage in traditional media is usually markets-oriented. I don't write about any of that. I don't care about earnings. I don't care about who's leading or lagging. All that is completely boring to me.
I think there's an ethos in the advisory community. This is what most mass media misses. It's baffling to me. Advisors don't care about all that. They don't care about all the markets crap that the media writes about. It's literally irrelevant for their practice. In fact, it's distracting for them.
Content that stands out from the ‘bland’ brands
Q. Let’s talk about your design aesthetic.
A. That's also different. You know, most people will not use the words that I use. They will not use sentences that are as short. They will not use memes or cartoons or jokes, even though they forget that these things are superpowers.
It’s the difference between when I see someone's content that I really appreciate versus what a brand puts out. Brands are very cautious. Everything's very bland. But when I when I see a creator whose work I really appreciate, it feels different. My reaction is I'm in a totally different space right now—the content is highly differentiated both in prose but also visually, and it doesn't even necessarily need to be expensive to produce.
I'm a one-man shop. I have people that occasionally do work for me, but how is it possible that I can get more attention as a solo provider hacking around in my basement studio? How can I get more attention than a trillion dollar brand? How is that possible? That doesn't make any sense.
My reaction [to the brands] is you're doing this wrong.
The idea that you drive conversion and conversion is measured by click through and then some additional action just doesn't happen. It does with just a tiny fraction of humanity, but I would say it’s an antiquated way of developing brand.
Brand is different than call to action. Brand is more like when you are in the buying mood, what are the top three names that even come to mind? Because so little of anyone's audience is ready to purchase at any given moment you need to just be top of mind.
Of the brands that I respect and are very effective, they are very, very good at establishing themselves as sources of information. They give a ton away and then when people are ready to buy, they know who the winners are. They instinctively seek out the brands that they already are aware of.
That's totally different from click here to get our white paper. Are you kidding? Nobody wants your white paper.
Q. You have a couple of brands now. You’re Brent Sullivan, you’re Tax Alpha Insider, you’re ADVDB.co…
A. Nobody cares about that.
Q. What is the model there? There’s no attempt to acquire names on that site, there’s no advertising on it.
A. So, this is another thing from this world—if I create a tool, I must monetize it right away. There’s a different way of doing things. I borrowed this much more from the enterprise SAAS world and from the software communities.
Just give everything away. And then what happens is you become known as someone who's good.
My argument to this world, to the financial services community, is that you're far better off becoming known as someone who's good. You’re better off becoming known as someone who's technically competent than you are at trying to monetize that competence in some kind of, in my mind, pathetic way.
Back to ADVDB.co, there are a ton of enterprise grade solutions out there if somebody wants to pay for advisor analytics. My thought was, “Well, I'm technically competent, I can build one for free and everybody can use it. It'll be fast and easy and it'll get me additional recognition.”
It's a tool that I use and I’ve got a number of people who like to use it. That’s good enough.
People should be building tools. If I'm a big brand and my raison d'être is content marketing, well, I consider tools part of content marketing. Brands don’t need to gatekeep everything. They don’t need to drive to a sales conversion. They don't need to connect users with a product specialist.
They don't need to do any of that. They need to convince them that they’re worth talking to. And then once they’ve done that, and that's already hard, by the way, then they can start solutioning.
But if you've not even convinced advisors that you're worth talking to, then what are you even doing? That's a joke to me, you know?
Every piece of content that a brand puts into the marketplace has to be industry-leading. This blows people's minds when I say this. Or else no one cares.
No one says “I will set aside my private time and I will read this secondary piece of content.” Advisors have limited attention. They’re going to read the best stuff. They’re going to use the best stuff. You have to be the best in some dimension.
And then you become known as the brand that does that one thing really well. That's so powerful.
It blows my mind when you’ve got brands that are just delivering this white noise machine content week after week. Stop! This does nothing. You're trying to play some completely antiquated game. You're hoping to fool people just through volume.
Q. Final question: What are your influences?
A. I really like primary research in this space. If anybody's doing interesting primary research, bespoke, unique, interesting research in taxable investing, that's a big deal to me. AQR does interesting stuff. Vanguard does interesting stuff. There are there are plenty of other brands. I hate to leave anybody out because everybody's working hard.
Q. Names of individuals?
A. Nathan Sosner at AQR and the team. I read everything that he writes. That's the clearest signal. Nathan is quite unique in his output.