Transcript: Wealthfront’s Andy Rachleff on Invest Like the Best

Andy Rachleff is co-founder and CEO of Wealthfront and co-founder of Benchmark. He is Patrick O’Shaugnessy’s most recent guest on the Invest Like the Best podcast, or as Patrick sometimes calls it, the “this is who you’re up against” podcast. Here is a link to the episode and notes. Rachleff covers various topics,

  • How the founders of Benchmark structured their partnership,
  • Putting the gun in the other person’s hand,
  • Benchmark’s investment in eBay,
  • Why Wealthfront is “a software company doing investing, not an investing company doing software.”

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Patrick O’Shaughnessy: So back to Benchmark and its unique structure. From what I understand, originally it was five partners and it was sort of an equal partnership…

Andy Rachleff

Andy Rachleff: Not sort of.

O’Shaughnessy: Exactly an equal partnership. So no politics and hierarchy I guess. What was the reason for that setup? How did you come up with that idea?

Rachleff: When we started as I said, what united the five of us was the desire to build the best firm in the business, not necessarily to make a lot of money. We thought if we built the best firm in the business, the money would follow. We were really, really oriented toward building the best and we felt as though whatever platforms we were previously associated with we could do very well but we couldn’t become the best. We tried to take the advice that we gave to our portfolio companies which is “pick who you think is your closest competitor and try to turn their greatest strengths into their greatest weaknesses.”

The firm that we perceived as number one by a long shot was Kleiner Perkins back in 1995. Fortunately I don’t think they are number one any longer but they were head and shoulders above everyone else. We thought they were head and shoulders above everyone else for two reasons. Number one, they had the world’s greatest venture capitalist in John Doerr. I think he is the best there ever was, and number two, they had a reputation for helping their portfolio companies do business with their other portfolio companies. So they referred to this as their Keiretsu. Back in the eighties, it was perceived that Japan was going to beat the United States sort of the way China [is perceived to be] beating the United States today. People wanted to emulate Japanese techniques and there are a bunch of networks of companies that affiliate with one another. There was a great attraction to entrepreneurs to be able to join one of these affiliations, their keiretsu so that if you got backing from Kleiner, they would help you sell products to other Kleiner Perkins companies.

We thought long and hard about how do we turn these great strengths into weaknesses. Classic judo. What we decided was John Doerr was the world’s best venture capitalist and his team of partners were also outstanding but entrepreneurs were often disappointed if they didn’t get John. So we wanted to compete with the individual with a team and we thought that if we built an equal partnership we could attract a better team than anyone else in the business because if we were competing with another venture firm for a particular individual as a partner, they had a choice of being an equal partner with us or a junior partner at the other firm. That was an intelligence test. Why wouldn’t you join us? It’s played out that way. It’s an always equal partnership. So if someone joins today, they have the same economic stake in the new funds as one of the founding partners.

Now the only way you can make this work is if the old guys leave, which is what they don’t do in the venture business. It’s usually the old guys suck up the economics and the young guys generate all the returns. We had been those young guys in previous firms and we said “we are not going to make that same mistake.” So we made a blood brothers pact that if any of us got to the point that we were not willing to work 110% on Benchmark, we had to opt out and take no economics in future partnerships. We could invest but we didn’t get any sweat equity, and we were all cool with that because we wanted to build the legacy. Now all the five founder have retired and when any of us go to the office, people smile at us because we are not soaking up their equity. So they like us as opposed to hate us as you typically do with the old partners in a firm.

O’Shaughnessy: One of my favorite thinkers in the entire world is Bill Gurley who is maybe the oldest…

Rachleff: He’s the oldest.

O’Shaughnessy: I was going to say most senior, longest standing partners. I read an interview with him that said the key to the success at Benchmark…I think he said at the peak of their power, the founders handed us the keys.

Rachleff: Yes!

O’Shaughnessy: I was reading a novel (Jitterbug Perfume) that I have to read this quote because I think you’ll really appreciate it. It’s about a Middle Eastern, almost fantasy land type little city-state kingdom, “In Alobar’s kingdom, a minute city-state, a tribe if you will, it was the custom to put the king to death at the first sign of old age. Kings were permitted to rule only so long as they retained their strength and vigor. Regarding its rulers as semi-divine God men upon whom the course of nature depended, the clan believe wide-spread catastrophes would result from the gradual enfeeblement of the ruler and the final extinction of his powers in death. The only way to avert those calamities was to kill the king as soon as he showed symptoms of decay so that his soul might be transferred to a vigorous young successor before it might be impaired.”

Rachleff: We believe in euthanasia. Let’s put it that way. So it’s incumbent upon each of the partners to raise their hand and it was really perceived as bad if you didn’t raise your hand.

O’Shaughnessy: Could you give one portfolio company example?

Rachleff: Let me just finish the other point and we’ll come back to this. One was team versus individual and the other one was Kleiner would often take the position of chairman of their boards. We thought that was inappropriate given the relative importance of the entrepreneur versus the venture capitalist. A lot of entrepreneurs once they were backed by Kleiner sort of felt pushed into doing business with other Kleiner companies as opposed to wanting the opportunity. Playing on that, we positioned ourselves whereby the entrepreneur was the star and we were the stage hands. So we never took the chairman title. We never pushed them to work with our portfolio companies. We would work very hard to make the introductions if they wanted but we never pushed them. Those two things combined with the three of us who had been in the venture business before for more than ten years, all had pretty good track records, and good networks…by bringing all that to bear, we were able to get off to a good start. We started at the best time you ever could’ve started a venture capital firm in 1995 as the Internet was taking off. It’s better to be lucky than good. Fortunately, we made some great investments and great investments spawned other great investments. We recruited great people like Bill Gurley. I think the team’s now is doing a better job than we ever did.

O’Shaughnessy: Before I ask that portfolio company question, you mention that John Doerr was the greatest venture capitalist ever. Why do you say that? What are the attributes or the skillset that made him the best?

Rachleff: He didn’t lose sight of what was important. You have to make a leap of faith to make a big return. Without risk, there isn’t reward. All of us want return without risk but unfortunately, it doesn’t exist. I think that Howard Marks puts it best when he applies the same framework to all of his newsletters. Howard is the founder of Oaktree Capital, which is probably one of the best distressed debt investors but he’s as well known for his quarterly letters to investors as he is known for his great returns. Every one of his letters is based on the same framework which describes investing with a 2x2 matrix. On one dimension you can be right or wrong and on the dimension, you can be consensus or non-consensus. Obviously you don’t make money if you’re wrong but what most people don’t realize is you don’t make money if you’re right and consensus. All those returns get arbitraged away.

So the only way you make money is by being non-consensus which is really hard because you know you’re non-consensus but you don’t know if you’re right. Now with John, I think that he was riveted on what could be big. If something can be big, that sort of swamps everything else.

O’Shaughnessy: Meaning the market size?

Rachleff: The market size. You don’t want to be big today because it’s really hard to take share from big companies. It’s a lot better to invest in something that’s just emerging. John didn’t let anything get in the way of an opportunity that he thought would be big. If it was really high-priced like Netscape, he paid 4x the then normal valuation for Netscape and everybody thought he was nuts. He had the last laugh. Amazon he did the same sort of thing. He never let the quality of the people or the valuation or anything like that get in the way where others of us might have. I think that’s what made him great number one. Number two, he’s exceptionally bright and because of his success, he built perhaps the best network in the business. Number three, he has the best voice in the business. When you hear him speak, you just want to do whatever he says.

O’Shaughnessy: Amazing how powerful that can be. So maybe now we can choose an example because I’m always fascinated by the actual…everyone’s investment process. I think the venture process can be the hardest, at least for me, to understand. Using an example of a particular portfolio company, maybe from the first or one of the early Benchmark funds, I would be fascinated to hear what the company was, what it did, why it appealed to you, what the criterion were that seemed attractive, and kind of briefly summarize the story. That would be really interesting.

Rachleff: One of our first very successful companies was eBay. Now this is a classic venture capital story, and it incorporates why Bruce Dunleavie is so great. The founder of eBay he actually started the company as a hobby. He had never intended for it to be a business. Previously, he was the number four…he was the fourth engineer hired into one of the first pen based computing software companies, a company called Ink. Back in Merrill, Pickard days, Bruce made an investment in Ink so we could have a play in pen based computing. He didn’t go on the board but he made an investment. Bruce was such a great advisor that even though he wasn’t on the board, anyone in the company who had a serious strategic question would come to Bruce rather than one of the board members and Pierre Omidyar, the founder of eBay, was no exception. Well Ink pivoted into ecommerce. It was the first ecommerce company and changed its name to eShop. It was ultimately acquired by Microsoft. But eShop was the first company doing ecommerce on top of the CompuServe platform so before the internet.

So Pierre had some ecommerce in him. After he left eShop, I think he joined a company called General Magic and he ran this electronic community of his apartment and he called it eBay for “electronic bay area.” Now eBay if you went to the website, you would’ve found a page with 250 words in Courier font, old fashioned typewriter font and buried in this narrative were six links to six different applications, one of which…I think the fourth one down was called AuctionWeb which is what we know of eBay as being today. He did this sort of just for fun. It was one of the things to draw people to his community. I think he was trying to help his girlfriend sell Pez dispensers…was the famous story. But people were starting to trade other collectibles on it and even some other products. Well it grew so quickly that Pierre couldn’t afford to pay for the 56 kilobit line that he needed to connect his server in his apartment to the internet. So he felt guilty about this but he posted a note on the site that said “I’m going to have to charge a listing fee just to pay for this higher bandwidth line and maybe a little bit more server capacity.” Well from that day forward, the checks came in faster than the expenses. So fast forward a year and I think he was up to about $200,000 of net revenue per month and he was growing at 10% per month and the software broke all the time. It was spaghetti code. It was just awful. But he got an acquisition offer from a newspaper chain because I guess the newspaper chain correctly noticed that this might affect their classified business which was the most profitable advertising in a newspaper. Most people don’t realize that. We don’t even see these classified ads. But he had gotten an offer and he called up Bruce to see what he should do about it. Not to show us the investment but he wanted Bruce’s advice.

So Bruce listened to Pierre tell the story and at the end of the breakfast, Bruce said “you know Pierre I think you’re onto something here. Would you be open to raising a little money, a portion of which we would use to buy some of your stock so you can take some money off the table because I know this acquisition offer is attractive to you so you can buy a home. Would you be open to that?” And Pierre said, “Yeah, okay.” So then we went back and talked about it. We met the company and it struck us all that this platform that was being applied to collectibles and when people wanted to insult us “Beanie Babies, really? That’s what this thing is for?” We saw it as an opportunity to sell many other things besides Beanie Babies or Pez dispensers. That was the leap of faith. That was the non-consensus idea. It wasn’t until the company went public that people stopped making fun of us for having made that investment, and that’s what usually is associated with the most successful investments.

O’Shaughnessy: Fascinating.

Rachleff: In technology. And Bruce didn’t go on the board. My partner Bob Kagle, who was the one most focused on the intersection of consumer and technology which back in 1997 even was not considered normal, did.

O’Shaughnessy: I think there are two things to take away from that. I’m curious to see if you think I’m right here. So the first is that there’s a component of success begetting success. Underneath all of this is the principle of compounding. The other thing with Bruce is it seems as though his operating system was to always help people, maybe without any particular expectation of a return but that because he was the one the eBay founder reached out to, that thereby created the opportunity. It seems that if you’re willing to just help other people in a very productive way without a particular goal in mind, that can create an enormous compounding network effect that might create the opportunities that these top 20 venture firms capitalize on.

Rachleff: You know it’s funny. I’ve always been a really big believer in the golden rule. We teach it to our kids but we seldom execute it in business. That always struck me as odd. One of the things that bound Bruce and I together was this common belief in operating that way. So much so that he had a philosophy that really impacted me and this was part of the mentorship. I don’t think he was consciously mentoring me but set a fantastic example. One of the things that I love about him is he has this philosophy that I call “putting the gun in the other person’s hand.” In any interaction, in any negotiation, Bruce always puts the gun in the other person’s hand. Now if they fire, he just doesn’t work them. So if he negotiates with an entrepreneur on a valuation, he will usually say “Patrick, you tell me what the fair price is and I’ll do it.” Now most people will feel pressure to not take advantage and to do the right thing. But there’s about 10% of people out there whose eyes will go wide and say “Oh my god. Really?” Then they’ll ask for a valuation that’s radically higher than what they deserve, and he would just choose not to work with them.

I do that in all of my dealings. I always put the gun in the other person’s hand, and that breeds great loyalty. I think it’s a much nicer world when you treat people the way you would like to be treated.

O’Shaughnessy: It’s kind of like the Munger-Buffett idea of “a seamless web of trust.” That “gun in the person’s hand” is another way of saying trust.

Rachleff: Exactly! Assume good faith.

O’Shaughnessy: Fantastic. So I believe that you were the person to come up with this term “product-market fit” and this kind of idea of a “value hypothesis” and “growth hypothesis.”

Rachleff: That part I didn’t come up with but the concept of product-market fit [I did]. I think Steve Blank and Eric Ries came up with those two hypotheses.

O’Shaughnessy: So I would love to use those as a bridge to describe what those ideas mean along with the innovator’s dilemma which may be our…King Alobar is a good example of to bridge into Wealthfront. So maybe you could start with your definition of product-market fit. It’s become a ubiquitous term. Given that it was your original idea I’d love to hear it straight from you.

Rachleff: Well I’m a big believer based on having observed technology companies for more than 30 years that if the dogs want to eat the dog food, you can screw up most everything else and you’ll still be really, really successful. So the entire goal in starting a business especially in tech is to get those dogs to eat the dog food. So my partner Bob Kagle used to say “you want products that are bought not sold.” When people want to pull it out of your hands, that’s product-market fit. Now the technical way that you can tell whether or not you’ve actually achieved product-market fit at least in a consumer business is if you grow exponentially organically. Now the only way you can grow exponentially organically is through word of mouth. The only way you have word of mouth is if people are delighted and love your product. If you achieve that, you can screw up almost everything else in the company and you’ll still be successful. This is the only way that I can explain how a 25-year-old can run a billion-dollar business. If the customers pull the products out of your hand, you don’t have to be that great at operating.

O’Shaughnessy: And what is the method through which…my favorite part about the venture capital world is taking lessons that tend to be applied in hyper speed and very tight feedback loops but taking a step back and applying them to small businesses or a slower paced business or even a mature business where innovator’s dilemma may have set in. How when you teach for instance students at Stanford, how does one go about finding a product-market fit? It’s a rare thing.

Rachleff: Well that’s where I think Steve Blank came up with a business innovation. Steve was the first person to describe applying the scientific method to business. When we’re in third grade, we all have to do a project on the scientific method. We have to come up with a hypothesis. We have to design an experiment. We have to come up with results and we have to iterate on that. Amazingly that had never been applied to business. Steve just came up with a framework to explain how one would apply that methodology to in effect finding the product-market fit. He wrote a book that was really just his teaching notes from a class he taught at Berkeley called The Four Steps to the Epiphany. One of the people who takes the course was a fellow named Eric Ries who became a disciple. Then Eric wrote a book called The Lean Startup which I refer to as the New Testament. You can think of The Lean Startup as the New Testament to Blank’s The Four Steps to the Epiphany Old Testament. It’s much more readable and more relatable. Just like the New and the Old Testament.

So basically what they came up with was a methodology by which you would first test a value hypothesis and then a growth hypothesis. So the value hypothesis represents the what, the who, and the how of your business. What do you want to build, for whom is it relevant, and what’s the business model to deliver that product? Now what’s different than what most people expect is that you don’t iterate on the what. You iterate on the who. Most people think that entrepreneurs start businesses that looking at a market, finding a problem, and coming up with a solution. That leads to very mundane outcomes. Back to the Howard Marks framework, that’s right and consensus. Anybody can do that. The great technology entrepreneurs basically recognize an inflection point in technology that allows them to build a new kind of product. Then the question is “who cares?” So you might change the way you describe that product or technology but you don’t really change the technology. You change who might want that product.

O’Shaughnessy: So it’s kind of like finding a large market that no one has identified or no one exists as a separate thing?

Rachleff: So you iterate on the who and that’s called pivoting. That’s become a very popular term and every successful technology company has pivoted. Now they all revise history to make you think they didn’t because that doesn’t feel good as a consumer

O’Shaughnessy: We like narrative determinism.

Rachleff: Exactly. The companies have to prove out their value hypothesis then and only then can they pursue a growth hypothesis which is a way to acquire customers cost effectively. Proof of the value hypothesis is exponential organic growth. Back to your question about what’s product-market fit when you’ve proven your value hypothesis.

O’Shaughnessy: It’s interesting to switch to the growth hypothesis. If the indicator of the value hypothesis is exponential organic growth, why do you need a growth hypothesis? If you’re acquiring customers via something like word of mouth…

Rachleff: Because faster growth is better.

O’Shaughnessy: Faster growth is better. So what are the components then of growth work? Assuming you’ve got something, the dogs are eating whatever particular brand of dog food, what are the particular components of scaling a business like that?

Rachleff: This is a whole new field called “growth” or “growth hacking.” The people who are best at it hate the term growth hacking because they don’t think it’s hacking. They think it’s a very analytical process. The growth function really consists of figuring out what’s working and then doing experiments around that to make that even better. What’s really interesting is that fixing what isn’t working doesn’t help you grow nearly as fast as improving what is working.

O’Shaughnessy: Like amplification in the evolutionary setting.

Rachleff: Exactly. It’s true by the way of us personally. That it’s a lot better to amplify what you’re good at versus fix the things you’re bad at.

O’Shaughnessy: There’s a kernel in there that I think is counterintuitive to a lot of people. People talk about learning from failure and that failure is necessary or a great way to learn…

Rachleff: I couldn’t disagree more.

O’Shaughnessy: That’s where I was going. It sounds like if you’re following this amplification idea, you’re actually going to learn more from success.

Rachleff: I think you learn more professionally from success. I think you learn more personally from failure. One of my former CEOs pointed that out to me, Brian NeSmith, and I thought that was a really interesting insight. Think about it: if I’m going to hire you to work here at Wealthfront, I’m not going to hire you for what you know not to do. I want to hire you for what you know to do. So learning from failure is great. You learn what not to do. But if you work at a really successful company, you’re going to learn some tricks that are unbelievably value that the person who has never been successful can’t possibly learn from reading about it. This is a really subtle but important difference.

O’Shaughnessy: If someone describes themselves as “well-rounded,” I almost think that that’s an insult. I’m more interested in people that have…

Rachleff: Although they’re really interesting to talk to.

O’Shaughnessy: I’m sure. That have some extreme competitive advantage in one particular area because that’s the kind of thing you can really ride. Fascinating. Now let’s shift gears to Wealthfront and the transition in your own life from venture capitalist to operator, now CEO. What has that been like? Before we get to the business itself…

Rachleff: Painful.

O’Shaughnessy: The difference in the roles I’m fascinated by. I’m not going to assume there’s anything that applies between the two…like lessons from the venture capital world that have made you a better CEO. Maybe there’s nothing.

Rachleff: I don’t think there really are many lessons other than having observed some great leaders, I think that I’ve learned a bunch of leadership tricks that can make me a better leader. Nothing about being good in venture capital makes you good as an operator or vice versa. It’s funny. One of the courses that I used to teach at Stanford was the foundation course for entrepreneurship. I had the good fortune to teach with an amazing guy named Mark Leslie who founded a very successful company called Veritas Technologies. He grew it from 0 to about a billion a half in revenue, and Mark hates venture capitalists, just hates them because it was a very non-consensus idea and he got turned down by a lot of venture capitalists early on. He enjoyed teaching with me despite the fact that I was a venture capitalist because we saw things very similarly. When I started this company, he was so happy because now I was an operating guy. I’ll never forget about a year in, he said to me “think how much better you’d be as a venture capitalist now as a result of this.” I looked him straight in the eye and said “Mark, nothing about what I’ve learned in the last year would make me a better investor! It would make me a better board member because now I don’t talk as much when I’m on a board because I realize how little perspective I have that I have to stay at 100,000 feet and I shouldn’t get into any of the details with the management team.”

O’Shaughnessy: It’s such an interesting comment because one of the often parroted Buffett phrases is “being an investor makes me a better businessperson and being a better businessperson makes me a better investor” and this is very different from that.

Rachleff: It might be the definition of businessperson.

O’Shaughnessy: It could be. So as now CEO and thinking about some of these ideas of product-market fit, change in technology creating a new market, what is the central thing that you think will make you successful going forward? The audience luckily is going to be very familiar with Wealthfront, with competitors like Betterment, with the automated investing platform idea. So we don’t need to go to deep into that core idea which I think makes a ton of sense but just to be totally blunt. I think that this type of solution is fantastic for young people in particular but I had an enormously hard time when I wrote a book called Millennial Money trying to get younger people to invest basically through an automated platform. There’s a whole section on automation and the power of it. I found it very hard to get them to go actually do it, to eat that dog.

Rachleff: Well that’s because there’s a rate at which people adopt new technologies. There’s a tremendous misunderstanding in the general public that if you offer something that’s better, everyone will beat a path to your door and automatically use it.

O’Shaughnessy: Diffusion of innovation.

Rachleff: Exactly, that you’ll just immediately…everyone will say “I should’ve bought that product. How could I not buy that?” Well actually the seminal book on this topic is one called Crossing the Chasm, written by Geoffrey Moore in the mid nineties, where he described what he called the technology adoption life cycle. That every product goes through a path. You start with innovators, then early adopters, then pragmatists, then the early majority, then the late majority [who] only buy when things are standards, and then the laggards, and that every product goes through this process. Nothing gets immediately adopted except if it’s just a better version of an existing product. When you create something new, it takes a while to get adopted. We’re actually being adopted at twice the rate that Charles Schwab was when they started, and Charles Schwab was adopted at a much faster rate than Merrill-Lynch because it was a discount brokerage versus a regular brokerage.

So while you might have had an issue, the rate of adoption of our service is radically faster than anything else in the history of investing.

O’Shaughnessy: One of the lines I saw was a quote from you saying a successful entrepreneur is someone that’s constantly innovating on top of an existing platform, creating new products. So I’m curious what that might look like because on the investment side, the current vanilla portfolio that you might get is I think what you’d expect. Modern portfolio theory, risk based allocations to the major asset classes via low cost instruments, which you’re not going to find many people that are going to argue that that’s a bad…

Rachleff: Oh you’d be surprised.

O’Shaughnessy: Their legion is shrinking and dying by the day. But for me when I peruse the Wealthfront products and obviously not your customer, I’m in the investment business. I manage my own money. Something like direct indexing where you’re constantly harvesting tax losses, something like that seems very interesting and the ability of Wealthfront to in the future continue to put things out like that across sort of the financial stack, not just necessarily in direct investing but across the financial technology stack, really interests me as a perspective user. How do you think about that? How are you trying to foster or avoid that innovator’s dilemma of sitting on that core product and instead constantly coming up with new ideas?

Rachleff: First and foremost, we consider ourselves a software company, not an investment company. So we’re a software company doing investing, not an investing company doing software which is the approach I think everyone else has taken. We started with a very rudimentary product and that was a diversified and rebalance portfolio of low cost index funds. I used to say people that “we offer very little value and price accordingly.” That used to drive my colleagues here at Wealthfront crazy but it was honest. Net of fees and after taxes, it was still radically better than what the vast majority of people in the United States have access to but it was boring and rudimentary. The beauty of software is that it constantly improves. If you have some knowledge about investing, you can add value. So from the very beginning, we did something different from any other player in our space. That was, we had a strategy of taking all of the services that are traditionally available through private wealth managers, people who provide financial advice, places like Goldman Sachs and Morgan Stanley and who have a minimum investment account of $5-$15 million, automate what they do through software and deliver them to the masses, thereby democratizing access. Now we focused on young people because we thought they would care much more about a product that was delivered via software. Older people want to talk to someone. We don’t think our solution is ideal for them. Will some want it? Yes. Will some young people prefer to talk to people? Yes. But the vast majority of young people live their lives electronically and they actually tell us “we pay you not to talk to us” which is the exact opposite way the traditional industry thinks. The traditional industry thinks “when they get older, they’re going to come to their senses and want to talk to someone.” That’s like saying “someone listens to rap when they’re young. When they turn 50, they’ll want to listen to symphony.” I’m sorry, but I think it’s a generational change.

So we focus on young people who have less than $1 million who want to delegate, and why less than $1 million? Because at $1 million, you can afford access. That’s the minimum for a financial advisor. Less than $1 million, you have no alternatives. So we started thinking about “well what are some peer-reviewed, rules-based strategies that we could apply on top of what we do?” First we did tax loss harvesting, and it’s amazing in the four years since we’ve offered this service, on average it’s added 1.8% to our clients annual, after-tax return. It’s almost too good to be true. Now this has been around for decades where people do it at year-end. They harvest losses or recognize losses and replace the securities that have been sold with something similar so you maintain the risk and return characteristics of the portfolio but by using those realized losses to lower your taxes, you increase your returns. Software does routine things better than people. Now it’s really hard if you have 100 or 200 clients as a private wealth manager to look at your clients’ accounts every single day to look for losses you can harvest, especially given all the tax slots associated with multiple deposits. But software doesn’t care. So we can do it on a daily basis and offer something better than even private wealth managers can do.

Then we recruited Burton Malkiel who I think invented the index fund in his book A Random Walk Down Wall Street as our Chief Investment Officer, and he suggested “rather than just do tax loss harvesting across index funds or ETFs do it within an index?” That’s what direct indexing is. So if the S&P 500 is up 1% but Coke missed their earnings and they traded down 5%, you could sell Coke and buy Pepsi. That adds another 0.2–0.5% to your return after tax, ever year, and we don’t charge anything incrementally for either of those services. So these value adds more than pay for our 0.25% fee.

Now you’ll see us add more peer reviewed, rules based strategies that enhance after tax returns. In February, we announced financial planning. Now again if you’re young, you can’t afford a good financial planner because financial planners long ago figured out that they can’t make money charging an hourly fee. Maybe they’d make $100,000 a year but if they wanted to make $500,000 a year, the only way they can do that is by charging an asset fee, and you have to have a minimum of $1 million. Now they may not be great investors but that’s how they monetize their service. So if you have less than $1 million, you don’t have access to them. But even if you did, what they do is interview you just to get the inputs into a commercially available software package. It’s not like they’re adding a lot of value. They all use the same package, and then they type in the inputs. They share the output with you two weeks later. You edit the output. The planner goes back to his commercial software package, puts in the edits, and two weeks later, they share that. Well with application programming interfaces, we can connect to all of your financial accounts, get much more accurate estimates of what you spend and save. We can give you the results immediately. We can give you the interactive tools that you can even work with while you’re in line at Starbucks on your phone and give you a far better financial planning experience. Today we just announced…we started with retirement planning. Today we offer college planning. We can actually tell you what it’s going to cost to go to any college you pick and any type of college. We can even tell you what the financial aid is going to be. You can’t get that anywhere on the internet.

So the beauty of software is it can do a better job. A few weeks ago we even introduced our portfolio line of credit, another private wealth management service of securities-based lending. So if you invest at least $100,000 with us, then you are automatically enrolled in a line of credit. No credit check. Nothing. And you can borrow up to 30% of your account value at interest rates below any interest rates on Wall Street and probably about at two-thirds the cost of a home equity line of credit. It’s amazing what we can do through software. No one else in our space is doing this. Other people are adding advisors to what we did two years ago with our rudimentary software.

O’Shaughnessy: It seems that there will be because of software, anything pertaining in public markets, that there will be this barbell that gets pushed further and further towards the ends where the big middle of the old-school active stock picking, mutual funds manager is having a horrible time right now…

Rachleff: As they should.

O’Shaughnessy: Arguably as they should because they are charging fees for what in aggregate has to be a losing proposition because of simple fee math. But now I’m finding because I get to talk to investors of all stripes a keen interest still in active management. It just seems to be going more esoteric and more private. You come from the world of the ultimate stock picking, you know ultimate privileged access, top venture firms that no one can get into that has these amazing returns. I think that’s what always appealed to people about active management was some privileged access. Do you foresee Wealthfront getting into some of those spaces, potentially democratizing access to private markets which have become enormous?

Rachleff: You know it’s really funny. One of the things that we will not do that private wealth managers do is offer access to alternative assets, and the reason is because of the old Groucho Marx line “I would never join a club that would have me as a member.” Let me explain what I mean by that: one of the primary tools that wealth managers use is “hey, I can give you access to hedge funds or venture capital or buyouts.” The problem is the ones that they can give you access to suck, and the reason they suck is…back to when I was a partner of Benchmark, the last person I wanted was a retail investor in my fund. Why? Because as you know, there’s been a tremendous amount of research done that shows individual investors, retail investors buy when the market goes up and sell when the market goes down, the exact opposite of what they should do. They’re the opposite of a contrarian. Contrarians make money.

So why do I want an investor in my long-term capital fund who is going to feel the urge either to want to sell when the market goes down or not want to meet their capital call when I need it? Now if I’m in the fortunate position to be able to choose any investor I want, that’s last investor I want. So the best investor, the one who’s the most long-term oriented is either a university endowment or a charitable foundation, all things being equal and there are obviously exceptions. But on average, those are the best. So that’s true for all the premier venture capital funds. The only venture capital funds that will let Morgan Stanley or Goldman Sachs invest in their funds are the ones that are desperate for capital. They suck. The same is true of the best hedge funds. The same is true of the best private equity funds. So by definition, if Goldman Sachs or Morgan Stanley give you access, run away! So I’m sorry. That’s why we’re not going to offer it. We can give you some additional asset classes that are not correlated that are liquid and that are rules-based and peer reviewed but they’re not going to be those alternative assets.

O’Shaughnessy: Well sadly we only have time for one more question but it’s my favorite and always my closing question which is to ask what the kindest thing anyone has ever done for you?

Rachleff: Gosh, I’ve been the recipient of an amazing amount of kindness over the years. I actually think my entire career is a function of kindness and luck. When I was in business school, it’s really funny. I worked on Wall Street for a couple of years after college and I worked in mergers and acquisitions at Blyth, Eastman Dillon & Company. The head of the M&A department was a Stanford grad and he encouraged me to go to Stanford Business School because he knew I wanted to get into venture capital. He wrote a wonderful recommendation and I was lucky enough to get in. So that was really good. Turns out his son was a year ahead of me at business school, so he took me under his wing and his son introduced me to one of his best friends who as it turns out his father was then the CEO of Hewlett-Packard which was the Google of the day and he had gone into venture capital and for some reason he took a liking to me and he introduced me around to venture capital firms. That’s how I got into the venture business. I started working while I was going to school, and just over and over and over again people have done amazingly nice things for me to give me an opportunity and that’s why I’m such a big believer in the golden rule.

O’Shaughnessy: That’s been a theme of our conversation, that it’s not a short-term edge but a long-term one and so great closing answer. Well thank you very much. This has been as fun as I knew it would be. Have a great day.

Rachleff: Thank you very much.

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