E316: How Family Offices Design Portfolios for 30-Year Outcomes

3 Mar 2026 · 29 min · 6 chapters

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Podcast Summary: How I Invest with David Weisburd - Episode E316: How Family Offices Design Portfolios for 30-Year Outcomes

Episode Overview In this episode, David Weisburd interviews Zach Wainwright, Founder of Twin Oak ETF Company. They discuss the concept of structural alpha, the tax efficiency of ETFs, and strategies for high-net-worth investors aiming to compound capital intelligently over a long-term horizon. Wainwright shares insights from his extensive experience at various prestigious investment firms, emphasizing how family offices can design portfolios to endure extreme market conditions while still achieving long-term growth.

Key Themes and Concepts

  1. Long-Term Investment Philosophy
  2. Importance of Time Horizon: Wainwright highlights that having a long-term perspective on investments is crucial, especially for family offices that are managing wealth for future generations.
  3. Asset Owners vs. Investors: A fundamental distinction is made between simply being an investor and being an asset owner who actively compounds capital over time.
  1. Structural Alpha and Tax Efficiency
  2. Defining Structural Alpha: Wainwright discusses how strategic alignment with long-term goals, tax awareness, and appropriate investment vehicles can yield better outcomes than traditional stock-picking strategies.
  3. Tax Alpha: He emphasizes that the tax implications of investment vehicles can dramatically impact net returns. ETFs, due to their structure, can provide a significant tax advantage over mutual funds.
  1. Investment Experience
  2. Lessons from Wellington and TIFF:
  3. Value Investing: Wainwright identifies himself as a value investor, emphasizing sustainable competitive advantages in businesses.
  4. Early-Stage Fund Managers: Investing in funds at the beginning of a manager’s career can lead to the best performance, despite higher risks.
  1. Family Offices and Risk Management
  2. Different Types of Family Offices: Wainwright categorizes family offices into those focused on steady growth versus those willing to accept higher risk for potentially higher returns.
  3. Structural Edge in Family Offices: He explains how family offices can create structural advantages by having a comprehensive balance sheet rather than segmented buckets of investments.
  1. Tail-Risk Hedging
  2. Hedging Strategies in ETFs: Wainwright explores innovative ways to implement tail-risk hedging within an ETF framework, allowing for reallocation and liquidity that traditional hedge funds cannot provide.
  3. Market Downturn Management: The conversation covers the importance of not only protecting against downturns but also deploying capital effectively during market recoveries.
  1. Creating Value for Clients
  2. Investment Philosophy at Twin Oak: Wainwright discusses three primary ways to create value: security selection, asset allocation, and structural alpha, with a focus on being tax-aware.
  3. Client-Centric Innovation: The firm aims to provide solutions tailored to family offices' specific needs, ultimately creating products that enhance wealth retention.

Key Takeaways

  • Tax Awareness: Understanding and leveraging tax strategies can lead to superior investment outcomes over the long term.
  • Benefits of ETFs: ETFs can offer more tax-efficient structures than mutual funds, helping investors retain more capital.
  • Importance of Diligence: The need for thorough diligence is amplified when making long-term commitments, especially with early-stage fund managers.
  • Contrarian Investment Opportunities: Family offices have the flexibility to invest in non-traditional opportunities that don't fit standard investment buckets, allowing for unique value propositions.

Conclusion Zach Wainwright's insights reveal that successful long-term investing, especially in the context of family offices, requires a profound understanding of structural alpha, tax implications, and the capacity to adapt to market dynamics. By focusing on these areas, investors can enhance their portfolios' resilience and growth potential over multi-decade time frames.

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Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Episode Discussion

0:00 to 14:00
“So you've worked at some of the top investment firms in the world, Wellington, TIF, at a top single family office.”

Tail Hedging for Family Offices

16:29 to 23:24

Explore how family offices address market volatility through tail hedging strategies.

“We kept hearing from a number of families that they were worried about kind of where the market was.”

Building Long-Term Public Portfolios

23:24 to 27:51

Understand the optimal strategies for constructing long-term public portfolios.

“So we like to think of ourselves as like client driven innovators in the product space.”

The Importance of Tax-Aware Investing

27:51 to 29:19

Learn why a deep understanding of the tax code can provide a competitive edge for investors.

“And can we help you keep more in your pocket?”

Diverse Experiences Lead to Unique Solutions

29:20 to 30:29

Discover how diverse investment experiences can lead to better problem-solving.

“I got told this when I was younger in my career, so I'm borrowing it from somebody else, but I think it really holds true.”

The Future of Taxware Investing

30:30 to 31:08

Explore the anticipated growth of tax-aware investing firms in the coming years.

“And, you know, I get told a lot of if that was true, Goldman would be here at my door pitching me on it.”
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Transcript

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0:00David Weisburd:So you've worked at some of the top investment firms in the world, Wellington, TIF, at a top single family office. What are some principles that you learn that you apply to your day-to-day investing career?

0:13Zach Wainwright:The starting point is have a long time horizon, right? When you start your investing journey, everyone tells you think long term. And for someone who's 21 years old, that's never had a job before, like that's very hard to really put that into effect. But I think as I roll forward and I worked at TIFF and I worked with family offices, long-term means a different thing. And I now have a true appreciation for what that means. Taking an investment for a quarter or four quarters, even if that could be long-term in the public equity investing world, means something very different when you're investing for the next generation.

0:46David Weisburd:And why is that so important?

0:48Zach Wainwright:It gets back to the idea of are you an asset owner or just an investor? And I think great investors can be both. But the idea is you deploying your capital and letting it compound and continue to drive value for you for a very long time. And when I think about my investment philosophy, it's how can you unlock the potential inside of a portfolio? And I think there's different levers you can pull, but it's really about aligning it with the time horizon that you have. What were your lessons from your time at Wellington? to. It's a great place to start your investing career because you see so many different disciplines.

1:23Zach Wainwright:You see growth, large cap, small cap, international. You see a lot of different tools being deployed. And I think for me, what that taught me was you have to figure out what's true to yourself. What is it that you believe that you can kind of have a repeatable, sustainable, competitive edge on? And for me, I was very clearly a value investor and I was looking for high quality businesses that had something that caused price and value to diverge.

1:50David Weisburd:And you went from Wellington, you went to TIFF, almost the opposite end of the market. You went from the public markets to investing into early stage fund managers. What were your lessons at TIFF and what is something that you learned that was very counterintuitive? I thought I was long-term before I got there.

2:07Zach Wainwright:And then when you're forced to make a commitment to something that has potentially a 15-year lockup and no path to exit, that's really being long-term. And I think that brings with it a level of rigor into diligence that was pleasantly surprising.

2:25David Weisburd:And at TIFF, you focused on funds one through fund three. Why take the risk investing early in a manager's career? What's the upside?

2:33Zach Wainwright:The statistics are fund one to fund three We are a manager's best performing funds. And so if you miss those, you lose two different ways. One, you miss those funds, but you also miss the chance to access those managers later because once they're identified, it can be hard to get into. By the time that the manager has been de-risked, everybody sees this.

2:53David Weisburd:The LP alpha is no longer there. So you have to go in earlier where there's higher risk, higher return.

2:58Zach Wainwright:And you want to align your incentives with the manager, right? So those early fund managers, the funds are typically smaller. They're not making a lot of money off of the management fee. they make their money off the carry dollars. Whereas a KKR is going to make a great return just from the management fee. And so you just have different incentives.

3:16David Weisburd:And if you think of alpha as extremely scarce, you have to think upstream of that, what generates alpha? It's typically really difficult things. It's looking for companies in the middle of nowhere, it's doing that extra work, it's working a hundred hours a week and somebody that's making millions of dollars or in some cases, tens of millions of dollars a year in management fees on the incremental deal, they may not actually pursue it. They might not pursue that alpha because it's too costly from a personal standpoint.

3:45Zach Wainwright:If a fund one doesn't go well, there is not a fund two. And so they're going to work out the companies in their portfolio when things aren't going well. They're going to maintain a high bar when they're deploying new capital because their sustainability is on the line. And so that's actually phenomenal incentive alignment. And as an allocator, you really need to try and assess that, right? You need to try and calculate that risk return trade-off for making that. And I actually think that's like a skill set that direct investors really capture well. There's no perfect investment out there. If someone finds one, I'd love to hear about it.

4:22Zach Wainwright:But there's something wrong with almost every investment that you make. And it's calculating that risk return framework. And emerging managers, that's kind of the same thing. There's something wrong. with it. It could be a short track record. It could be a small team. And you have to kind of look through that. And the people who have done that really well, they get into early managers. They stay with those managers for a very long, successful career. And MIT, Yale, those endowments are kind of core to how they've invested and how they've generated a lot of their outperformance.

4:52David Weisburd:When you look at early stage managers, you said there's something wrong with every manager. What's something good that could be wrong? And what's something clearly bad that you don't want a manager to have.

5:01Zach Wainwright:The biggest cardinal thing you can make a mistake in as investors partnering with people who are not good people, right? That when there's an ethical concern or some reason why maybe they were fired from a prior firm because of something, and you really need to try and spend your diligence unpacking. Is that just a story or is there something fundamentally flawed there? Because to what I said, like you're in these investments for 15 plus years. You will likely, that commitment will likely outlast your time at the place where you made that commitment and you need to avoid those mistakes. The thing that you can best align yourself with is doing whatever you can to increase the alignment.

5:38Zach Wainwright:So managers who make a very large kind of GP commitment to a deal where they're the largest investor in their own deals, right? They're eating their own killing, what they're killing. And so that's a phenomenal way to partner, right? Someone who's going to put 20 % of the capital to work themselves and you're really there to amplify their capacity. After TIF, you went inside a single family office.

6:01David Weisburd:So you went from a large institution as Wellington to TIF, which is today roughly a$9 billion pool of capital to a single family office. What changed when you joined that family office and how did you

6:13Zach Wainwright:view your investing mandate there?

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7:40Zach Wainwright:Over the last 20 years, I feel very fortunate to have met a lot of family offices and I'd kind of put them into two camps. starting point is they've all already made generational wealth. And so their incentives could be very different from other investors' incentives. There's one camp that let's just be steady. Let's compound and kind of continue to incrementally grow our family's balance sheet

8:04David Weisburd:to support the future generations. And then there's others where they have a much higher,

8:11Zach Wainwright:that manifests as a much higher risk tolerance. They can afford to have a 30 % drawdown because they're not taking food off the table. They're not having to make layoffs. And so that can give them kind of a higher risk tolerance. And therefore they can make investments that are different from the investments that you and I might make personally. And so I think I put that into kind of the structural edge that can be developed at family offices. And I think the best family

8:37David Weisburd:offices, try and develop a structural edge in how they deliver their returns. What's one or two examples where family offices can create a structural advantage versus other investors in the market?

8:52Zach Wainwright:I mean, I like to always, the one that I like is buckets, right? If you look at a lot of allocators, they have buckets, right? They have a large cap manager, they have a small cap manager, they have their US bucket, their fixed income, et cetera, et cetera. Family offices, they don't have buckets, they have a balance sheet. And so they're able to, to maybe go into things that don't fit into a traditional bucket. That's always been kind of my favorite place to fish as an investor is something that doesn't fit cleanly into something else, because there's fewer people looking at it. And so there's more opportunity for mispricing.

9:22Zach Wainwright:I oftentimes think

9:23David Weisburd:about it as going contrarian against certain trends in the market that deserve contrarianism. Right now, everybody needs liquidity. So being a liquidity provider is a really good business to have. In other cases, other people are very bullish on something. Selling into that bullishness could be very lucrative. And the reason why family offices are uniquely able to do that is because it's their money. They don't have this need to raise new funds on hot trends and gain management fees on things that are topical. They're just focused on compounding their money. and they're incentivized to take the right action where capital sources with outside money are not incentivized to do.

10:06Being contrarian, you know, if people want to sell calls,

10:10Zach Wainwright:buying those calls cheaply. People want to buy calls, selling them those calls expensively and just trying to take the other side of some of those flows to kind of incrementally keep adding different return streams and levers that you can pull to drive out performance over time.

10:25David Weisburd:Following the single family office, you started your own firm. Tell me about Twin Oak.

10:30Zach Wainwright:I like to think of our kind of investment philosophy that we're trying to bear is there's three different ways in which you can create value for clients. There's security selection, which is pretty self-evident. There's asset allocation. So being in the right sectors, sub-asset classes, et cetera, right? Being international versus US, large cap versus small cap, single stock versus kind of diversified index. And then there's structural alpha. And so I think the theme that you probably have heard from me throughout this whole interview is being long-term. I think time horizon is a structural edge that we try and capture at Twin Oak.

11:06Zach Wainwright:And the second is tax aware. I think tax alpha is the easiest way to add alpha for clients. If you can just be smarter in your implementation of something, you can drive a massive amount of value for clients over time. Give me an example of tax alpha. So if you select an investment manager that puts up two points of alpha per year for 20 years, they're a top 1 % manager over time. Very hard to do both as an investor and also hard to identify that top 1 % manager because 99 % are not that. now if you had made that investment through a mutual fund the average mutual fund has about two percent per year of tax drag embedded in it based on just like how mutual funds function so congratulations you you pick that top tier manager but you lost all of that value due to tax drag and so you took on a lot more risk because you had to identify that top tier

12:08David Weisburd:manager and most likely as you did not.

12:11Zach Wainwright:And so you're almost virtually guaranteed to underperform. Now, if you had made that same investment through an ETF structure instead of a mutual fund structure, you would have kept that tax alpha. So another way to think about it is you would have generated two points of tax alpha in the ETF structure relative to a mutual fund. And so you would have really captured that investment alpha in that strategy.

12:32David Weisburd:So explain that difference between holding a position in a mutual fund ETF? Why is there such a dramatic change in tax?

12:41Zach Wainwright:In a mutual fund, when people come in and out, the manager has to sell securities to deliver cash to those exiting investors. At the end of the year, that capital gain that was generated

12:55David Weisburd:from those tweaking of the portfolios

12:58Zach Wainwright:or meeting inflows and outflows get distributed out to every investor. So you could get hit with kind of a phantom capital gain tax, even though you did nothing. You just bought and held your mutual fund. Now, an ETF is set up as kind of what they call a redeemable security. So people come in and out of the security at net asset value. And so in theory, no one else entering or exiting the fund impacts you in your investment return. So you don't feel that experience. So when the portfolio manager goes to sell a security, they can do it through this in kind redemption process. and that can be immensely valuable from an after-tax framework.

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13:36David Weisburd:You built something that I think is very interesting, which is essentially a hedge to S &P 500 in case there's a tail risk and there's some black swan event. Tell me about that.

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16:28Zach Wainwright:Conversation with a family. We kept hearing from a number of families that they were worried about kind of where the market was. And so and the volatility and the potential downside. And so we came back to them with this idea of tail hedging. And the starting point for that is, you know, buying puts on the S &P 500 costs, you know, two to five percent per year, depending on the period of time, which is really expensive. So no one wants to pay that level of expense. But even if they were willing to pay that level of kind of underperformance in a way, the ways in which they can access it today are inferior.

17:04Zach Wainwright:You'd commit to a tail risk hedge fund that's going to run that put selling strategy for you. But when that pays out, you need to rebalance away right away. You need to take that source of funds that was generated in March 2020 and go out and buy equities. That doesn't work in a private fund. There's illiquidity, there's gates. And so by the time you get your money back to be able to redeploy it, you have to pay taxes, you have to pay fees, and you've given back a lot of the returns. And so we started by saying, can we put that inside of an ETF so that we can do the reallocation for the end client.

17:42It's an ETF way to do what hedge funds are doing,

17:46David Weisburd:but are charging two and 20 and a half gates. How exactly do you go about doing that?

17:50Zach Wainwright:There's probably 40 different hedges that you can do at any different time and that hedge funds are looking at at any given time. It could be something as vanilla as buying puts on the S &P, or it could be something as complex as buying forward interest rate volatility in foreign markets as a way to hedge equity exposure. So at different times, we're going to move between that camp of 40 different potential hedges and put together a balanced book to really solve the pain point of that product. In a severe downturn that is very sharp and unexpected, do you have a source of funds that you can redeploy?

18:30Zach Wainwright:And that's kind of what we tried to create. And we wanted to make it as easy for investors to access as they could, single ticker in a portfolio.

18:40David Weisburd:there's no free lunch what's the cost of having a hedge on s &p 500 portfolio versus just having

18:47Zach Wainwright:that s &p 500 portfolio with with no hedge in the simplest terms like buying puts is expensive right it can cost you two to five percent per year as i mentioned and are you willing to pay that most people the answer to that question is no and so they keep it on for a period of time where they under hedge. And so then the hedge doesn't deliver what they expect. We started by saying, given kind of our backgrounds at hedge funds and institutional firms, what's the full toolkit that you can use? Can we use things that are more complicated? Can we trade things on swap? Can we use options? Can we really try and blend together what is a institutional level risk hedging book that will evolve over time to capture kind of the different market opportunities that we see in the hedging market.

19:39Zach Wainwright:And so that's what we did. We have a constant allocation to something that gives us convexity in the portfolio. So something when the market tanks, it will outperform.

19:52David Weisburd:You mentioned 200 to 500 basis points for a typical put on S &P. What's the cost of doing it and through an ETF?

20:01Zach Wainwright:If you just take the same strategy and put it inside of an ETF, there's no difference in the cost. I think for us, what we were trying to sell for is

20:07David Weisburd:what is the exact vector that we're addressing?

20:11Zach Wainwright:Our clients and this fund is not designed to solve the zero to 5 % down market, which is where a lot of the hedging happens. That's very expensive. That's not what keeps families awake at night. It's waking up and seeing the market down 30%. And so it could be as simple as moving to buying cheaper puts on the S &P. And those are, you know, the drag is much less. It's harder to quantify exactly what that drag is over time because we move to different types of hedges, some of which actually can have positive expected value and positive carrying costs. And when you blend those together, we're trying to offset the drag as much as we can so that we can maintain an adequate level of hedging kind of in all scenarios.

20:57David Weisburd:Said another way, you're really optimizing on the maximum drawdown. So some people might say, I would be comfortable with a 10 % drawdown. Some would be with a 20. And then I guess there's this efficient frontier of what percentage of your portfolio you're hedging away with what instruments. That's the complicated part.

21:17Zach Wainwright:For this fund, we try and take that onto our back so you don't have to worry about it. we're trying to deliver an outcome, a solution where you get equity-like returns, but with reduced drawdowns in extreme tail environments.

21:29David Weisburd:I've always been curious about this because probably 90 % of institutional investors have what is called diversifiers, which is hedges against the market. So there must be a very solid rationale to that. Has there been research on long-only exposure versus long-only with hedged products? And does long-only with hedge products? Not only maybe is it a smoother ride, which is important, but does it actually outperform? And so in what cases?

21:56Zach Wainwright:My favorite statistic is if over a 30 year period, you avoid the 10 worst performing days in the market or 10 worst performing weeks in the market, you 3x the performance of the market or something like that. Problem with that is the 10 best performing days in the market usually follow the 10 worst performing days, right? There's two really bad days and then there's a recovery. So if you also miss the 10 best performing days, you are underperforming the market by half. And so those are the problems that I have with like a buffer fund, for instance, right? Like they're really just protecting you against the drawdown, but if the market's down and then back up, you might not capture that recovery period.

22:40Zach Wainwright:and that will also cost you in the end. And so to the conversation we were having about the ways to access tail hedging that currently exist, doing that in a private fund where you can't rebalance away is a problem. In our fund, on those bad days, we're immediately looking to go out and buy more equity exposure because we need to capture those recovery periods because that's how you sustain your outperformance over time. It's one thing to avoid the downturn, which I think is a feat in and of itself. But then it's, can you in, in those moments deploy into that pain?

23:16David Weisburd:And your philosophy is you design with a family office in mind, and then you provide that to other family offices. Exactly.

23:24Zach Wainwright:So we like to think of ourselves as like client driven innovators in the product space. Someone comes to us with a problem, we solve that problem, and then we can make those strategies accessible to everyone. And so the tickers that we create are available. Anyone can go buy them. But we know that it solves a single family's problem or a multifamily office's problem. And while every family might have a different need, eventually they start to rhyme. And so what worked for David's family will also work for John's family over here.

23:52David Weisburd:You're in a unique vantage point where not only were you at these institutional investors in the single family office, but you have single family offices coming to you and helping you solve specific problems. What's your view on the optimal way to build a public portfolio for the long term?

24:10Zach Wainwright:The stat I always like to come back to when I sit down with them is if you bought the S &P 500 30 years ago and just let it compounded and removed all tax friction and fee friction from that access, you 25x your money. Do you want to 25x your money over time? Because very few people actually achieve that level of outperformance over the last 30 years because fees were introduced, taxes were introduced, suboptimal decision making were introduced. And so for us, they're coming to us, and I think what they're really seeking is an ability to compound tax deferred for a long period of time. And that's a mentality that is not pervasive in the investment ecosystem.

24:51Zach Wainwright:It's a very private markets type of approach to the public markets. Exactly. And we're trying to match our clients and our investment strategies to deliver the outcomes that they're wanting. And are we aligned on the incentives for that?

25:05David Weisburd:so starting this business a couple years ago what's been the most surprising thing

25:11Zach Wainwright:i've become really obsessed with etfs created a firm building etf products right and you think oh my god this is so people must know this and i still think people ask me what inning we are in

25:22David Weisburd:the etf evolution i say like the third inning there are so much more to do in the etf ecosystem

25:29Zach Wainwright:them, both from an awareness standpoint and also a product development standpoint. And that's where we're really trying to push kind of the envelope. I meet a family office, you know, almost every week that has at least a few hundred million dollars into any ETFs. And they didn't know that they were more tax efficient. They just bought them because they were easy and cheap. And so taking that knowledge and then saying, oh, but it could be applied to so many more different things. And on the other side, you know, we meet a lot of hedge fund managers that are looking to grow in the family office channel?

25:59Zach Wainwright:And can we help them ETF their strategy because they want to get access into that strategy? And I think that's really where we can sit at this intersection where we're helping institutions access the ETF market with sophisticated partners.

26:14David Weisburd:There's a couple of confluence of factors going on here. One is the high net worth, the family office world is gaining in prominence. So before all the products were done for the institutional, the non-taxable investor, just because they were just dramatically larger. And now with the rise of retail and the intergenerational transfer of capital and all these factors, the taxable investor himself or herself is just becoming more prominent. The problem that still persists within that, a lot of the large managers of that capital are not really incentivized for them to perform on tax efficient manner over 10, 15 years.

26:53David Weisburd:Yes, you could say in theory, they get another 2 % per year compounded over 20 years, they'll manage another 1.5x. But most people are not really thinking that long term. And most people honestly don't care as much. They're focused on, you know, selling products. And we have another trend now with the fee only the multifamily office, the, the RIAs that are now much more aligned with, with the client as well. So there's this general focus on the taxable investment within the taxable investors. There's a general focus on being more client facing and kind of lowering that principal agent problem that does experience.

27:31Zach Wainwright:We try and partner with a lot of those firms, right? Like we want to partner with those multifamily offices that think like us. And we want to partner with the, you know, the hedge fund manager that maybe is his own largest client. And he's realizing that, oh, maybe I should care about taxes now.

27:44David Weisburd:and so i think there is a change happening um but tax aware investing has been around for a long

27:50Zach Wainwright:time you know i i got interested in investing when i was 12 years old no good reason whatsoever just kind of a cool idea and i spent a lot of time with i was fortunate to spend a lot of time with family offices and one in particular gave me this piece of advice and this is you know 20 plus years ago a superior knowledge of the tax code is one of the most competitive edges you can have as an investor. Tax-aware investing, I think, is having a moment, and I think it will continue to have a moment because at the end of the day, what matters to you as an individual, whether you're a retail, family office, multifamily office, is how much do you keep?

28:25Zach Wainwright:And can we help you keep more in your pocket?

28:30David Weisburd:If you look at alpha as extremely fleeting, in most markets, somebody is buying and somebody is selling. So it's very difficult, if not impossible, to sustain alpha over long periods of time as information starts to become less asymmetric. In tax, you're essentially selling against government treasury that updates its policies sometimes once a decade. So it's much easier to sustain alpha in that perspective versus when you're buying and selling.

29:01Zach Wainwright:It's an interesting framework to think about it. I always like to think about it as this is tax deferral, it's not tax elimination, right? We're not getting rid of your tax obligation. You still owe the taxes, but can we remove the frictions along the way that get in your way of kind of deferring and compounding for long periods of time?

29:23David Weisburd:If you could go back 15 years ago when you were just starting your career, what would be one piece of advice that you would give a younger version of yourself that would have either helped you accelerate your career or help to avoid causing mistakes?

29:36Zach Wainwright:I got told this when I was younger in my career, so I'm borrowing it from somebody else, but I think it really holds true. Collect the most diverse set of experiences you can as an investor, because when you see the same problem everyone else has seen, you'll see a different answer.

29:52David Weisburd:And it's that simple.

29:54Zach Wainwright:In this conversation, I've talked about derivatives, public markets, private markets, venture, real estate. I've looked at all of these different things as well as from different client perspectives, right? whether I was working at a family office or an institutional allocator. And when I see a problem, I bring all of those experiences to bear on solving that problem. And that's how we think we can create something really differentiated and special, which is our structural edge. Every investor wants a differentiated strategy, or they want alpha, which oftentimes is a different

30:24David Weisburd:way of doing things. But when they see it, their first gut instinct is, well, that's different. That's not the pattern I've seen previous 10 times, not realizing that that difference is the source of alpha.

30:37Zach Wainwright:Exactly. Right. And, you know, I get told a lot of if that was true, Goldman would be here at my door pitching me on it.

30:46David Weisburd:I'm like, well, eventually they'll get to it.

30:49Zach Wainwright:You know, we saw it first and we kind of this is what we do every single day, all day long. Whereas even if Goldman gets into this business, it's a fraction of what somebody does in their day. And so eventually this will be really commonplace. I think if you had me on 10 years from now, which I hope you do, we'll be talking about kind of, oh, there's a hundred new firms that are doing taxware investing because that's the way it's going.

31:10David Weisburd:Well, Zach, thanks so much for jumping on the podcast. Appreciate everything that you're doing and looking forward to continuing the conversation soon.

31:17Zach Wainwright:Thank you so much for having me. It's been a true pleasure. Thank you.

31:21David Weisburd:That's it for today's episode of How to Invest. If this conversation gave you new insights or ideas, do me a quick favor. Share with one person in your network who'd find it valuable or leave a short review wherever you listen. This helps more investors discover the show and keeps us bringing you these conversations week after week. Thank you for your continued support.

From the publisher

What if the easiest alpha in public markets isn’t stock picking… but taxes?

In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office — and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding.

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