In Episode 69, we welcome legendary angel investor, Jason Calacanis.
We start with Jason’s background. From Brooklyn, he worked his way through college, then was in New York at the breaking of the internet. He started his own blogging company, and eventually sold his business for $30M. Later, he landed at Sequoia Capital as part of its “scouts” program, and went on to be an angel investor in a handful of unicorns (a startup company valued at over $1B).
As the conversation turns to angel investing, Meb starts broadly, asking Jason about the basics of angel investing.
Jason defines it as individuals investing in companies before the venture capital guys get involved (before a Series A). He tells us that the more you can analyze a company through data, the lesser chance it’s an angel investment. That’s because to get the huge returns that come through a true angel investment, there has to be some level of risk (in part, related to having less data-driven information about a company’s financials).
So, the challenge is to find that “Goldilocks” period – before revenues are so high that a VC is interested, but after a startup company has launched a product and shown a hint of traction (so many early stage companies end up failing even to launch a product). When you time your investment in this manner, you reduce your downside risk.
Meb makes a parallel to traditional equity investing, where only a handful of stocks make up the majority of overall market gains. He suggests this dynamic is likely even more exaggerated in angel investing.
Jason agrees. That’s why he suggests you want to go slow at the beginning, ramping up as you learn more, building your network, and growing your deal-flow. But when you get it right, it can result in massive wealth. Or as Jason says, “I think that this is a little secret way… a dark art of becoming truly wealthy… massive wealth.”
Meb points the conversation toward a section of Jason’s book which made the point that to get started in angel investing, you need at least one of four things: money, time, expertise, or a great network. He asks Jason to expound. So, Jason provides us some color on these different angel-factors.
This dovetails into how much of your net worth should be allocated toward angel investments. It’s a great conversation diving into the math of various net-worth-percentages, and how a couple of investment-winners can have a profound impact on your overall wealth. Meb tells us about his own early-stage investing experience, and how the contagious optimism is exciting.
Meb asks what are some resources and places to go for more information. Jason points toward doing some syndicate deals. By doing so, you can read the deal memos, and track the investments even if you never actually invest. It’s a great way to learn – Jason uses the analogy of playing fantasy baseball. The guys go on to discuss ways to grow your network through other syndicate investors.
A bit later, Meb asks about pitch meetings when company founders are looking for money. What’s your role as a potential investor in these meetings? Jason likes to ask the question “What are you working on?” He then provides some great reasons why this question is effective. A follow-up question is “Why now?” In essence, what has changed that makes this moment right for your business? For example, for Uber, it was GPS on phones.
Curious what the “why now?” of the moment is? Robotics is one of them. Jason gives us a couple others (but you’ll have to listen to discover what they are).
The conversation drifts into how to exit your angel investment (or invest more). Jason says if you have a breakout success you want to quadruple down. For instance, if a big VC like Sequoia is thinking about investing, you’d definitely want to jam as much money in as possible. The guys then discuss taking some money off the table if your investment goes public, perhaps selling 25% of your position at four different times.
Meb likes this idea, as we discuss the behavioral challenges of investing so often, with so many investors thinking in binary terms – “in or out?” But scaling is such a powerful concept.
There’s so much more in this episode, and if you’ve ever been curious about angel investing, you’re going to learn from the best. The guys discuss how the lack of liquidity can be a blessing in disguise… why the sophomore year of angel investing can be brutal… a great way to tell if your angel investment is doing poorly… a huge ($10M huge) tax benefit of early stage investing… and of course, Jason’s most memorable trade – it turns out, he was the 3rd or 4th investor in Uber.
Want to hear the details? You’ll get them all and more in Episode 69.
In Episode 68, we welcome Meb’s friend and Newfound Research founder, Cory Hoffstein (or as Meb refers to him, a “fellow nerd”).
Per usual, we start with Corey’s background, but then Meb jumps in by asking Corey to describe his general, 10K foot investing framework.
Corey tells us that a specific product and/or style doesn’t necessarily define him or Newfound. Rather, he believes in a consistent, well-researched process that takes into account the behavioral challenges that accompany any given investment strategy. This is because the journey is often just as important as the destination.
Meb asks where Corey starts when creating a portfolio. Corey tells us it’s about the balance of risk. This is because “risk cannot be destroyed, only transformed.” Therefore, when building a portfolio, there’s no single holy grail. You need to understand the goals and fears of your client, then figure out how to balance various strategies in order to find a robust, flexible portfolio that handles risk appropriately.
This dovetails into one of Newfound’s white papers, “Portfolios in Wonderland,” which tackles today’s investing climate. Corey tells us that we’re in a unique environment, whether focusing on equity valuations or interest rates. It used to be that stocks and bonds zigged when the other zagged. But in the 1980s, both became cheap. Today, we have the opposite: high equity values and low yields on fixed income.
This leads to a great discussion on bonds, including Corey’s rule of thumb for estimating future bond returns, and his research into the source of bond returns – how much was due to the coupon, versus declining rates and roll yield.
The guys agree that with U.S. equities richly valued, and bond yields so low, future returns of the classic 60/40 portfolio don’t look too appetizing. So, what’s the solution?
Corey likes the proliferation of asset classes that used to be found almost exclusively in hedge funds. Now, we can use them to diversify our portfolios and reach a solid rate of return. The conversation bounces around a bit here – how 8%-10% returns aren’t likely going forward unless you’re invested exclusively in emerging markets... how if you let a portfolio optimizer do its thing, you’d have almost no U.S. exposure in either equities or bonds... and how, behaviorally, most people couldn’t have 0% allocated to the S&P, so finding a balance between the best portfolio and the most realistic portfolio is needed.
Meb asks how much drag there is on returns when moving away from the mathematically “best” portfolio to a portfolio which investors can actually stomach. Corey tell us investors are probably giving up 50-100 basis points of return which, over the long run, is a meaningful difference.
It’s not long before Meb asks about new research Corey is working on. Corey tells us he’s looking at much complexity an investor should bring into a portfolio. Some small details can make a huge difference. This leads to a great discussion about “timing luck” when it comes to trend following. More specifically, when you choose to rebalance can make a huge impact on your returns. If you’re a trend follower, make sure to catch this part.
A bit later, the guys discuss another white paper from Corey, “Outperforming by Underperforming.” This leads into a conversation about the challenges of looking different with your strategy, as well as the right time-frame needed to evaluate any strategy. The conversation includes a great quiz Corey often asks his audiences regarding Buffett and how badly he has lagged the S&P at times. Chances are you’ll be surprised to hear what Corey says.
There’s way more in this episode, including answers to “Should we be holding more cash?” “Is dividend investing dangerous” and “How do you factor in various global interest rates when looking at a bond allocation?” There’s also how Corey constructs multi-asset portfolios… how value works across asset classes… the biggest concerns Corey is hearing from clients today… an idea Meb has for a “weird ETF”… and of course, Corey’s most memorable trade.
What is it? Find out in Episode 68.
In Episode 67, we welcome Simon Black, founder of the newsletter, Sovereign Man.
We start with Simon’s military background, having been an intelligence officer. He spent lots of time overseas, yet became disillusioned after the promises of WMDs failed to prove accurate. From this, he began challenging the status quo.
Underpinning everything was an ethos of personal freedom, which is at the core of what Simon’s newsletter, Sovereign Man, is really about.
Meb asks what global red flags and/or issues Simon is seeing now which might be challenging our personal freedoms. Simon tells us “I see a lot of red flags.” Specifically, he’s seeing a global trend toward socialism. People have a sense that the system is rigged. There’s an intuitive understanding that something is wrong, though people aren’t quite certain what it is, so they blame capitalism. But when people gravitate toward socialism (“I want more free stuff”), we run into the challenge of too many people wanting to jump on the cart, without enough people actually pulling the cart.
This leads to an interesting conversation about the effects of socialism in Venezuela, where Simon is located. He mentions how there are vast quantities of soil where the Venezuelans could be growing crops, yet there is starvation. He steers the conversation back to challenges here in the U.S., which leads toward the need for what Simon calls a “Plan B.” In essence, this is a plan intended to protect yourself and your assets from the various risks we face today on many levels – financial, personal, governmental…
Part of an effective Plan B ties to diversification. Simon mentions how if all of your assets are in the same banking system, then you’re not diversified. So, Simon suggests at least some money should be kept in banks outside of the U.S. – after all, there are many global banks that are better capitalized than those here in the U.S. He offers Hong Kong as an example.
The conversation drifts toward an example of personal diversification – getting a second passport. Simon thinks this is the ultimate option, providing tons of opportunities and benefits – all upside with no downside, for minimal cost.
Next up is Simon’s suggestion to legally reduce your tax burden. He tells us “reducing your taxes…that’s the easiest return on investment you’ll ever make.” Simon tell us a favorite tax-reduction technique upon Meb’s request.
Next up, the guys discuss having cash outside the U.S. banking system. The conversation references why this is important – just look at what happened in Cyprus and Greece a few years ago. This leads into a discussion of cryptocurrencies. Simon tells us how so many people putting money into crytos today now have no idea what they’re doing – do they even understand Bitcoin and Ethereum? Who has actually read the original white paper on Bitcoin?
There’s way more in this episode: where Simon is looking now for safe, margin-of-safety-style investments around the globe… how private equity can help your portfolio… Simon’s entrepreneurial advice… what Simon’s readers are most concerned about today… and of course, Simon’s most memorable trade – it involved day-trading Compaq (and losing everything).
How’d it happen? Find out in Episode 67.
Episode 66 is a radio show. We start with Meb referencing the just-published book, The Best Investment Writing, which he edited. It’s a great collection of essays from some of the smartest minds in investing. Check it out.
Next, we jump into market commentary, using Meb’s recent “office hours” as our vehicle for discussion. What that means is Meb had some extra time over the last few weeks, so he opened his calendar to his followers, scheduling loads of 30-minute phone calls with various individual investors and RIAs looking to pick Meb’s brain on a variety of subjects. Meb tells us the topics which came up the most often, as well as his thoughts. There’s talk of U.S. equity valuation (and at what level Meb would start selling even before a crash), angel investing, portfolio allocation weightings, and far more.
We end with several listener questions. The first involves how Meb views market breadth in light of the growth in index investing; the second solicits Meb’s thoughts on the dangers of ETF investments if the market heads south; the third is at what valuation level the buyback component of a shareholder yield strategy ends up being a headwind.
What valuation level did Meb indicate? Find out in Episode 66.
In Episode 65, we welcome CTA and commodities expert, Emil van Essen.
Meb starts with a fun bit of trivia – if you mesh his and Emil’s name, coming up with “Emil Faber,” can you guess in which movie that name appears?
It turns out it’s from the classic comedy, Animal House. “Emil Faber” was the founder of the movie’s “Faber College” and under his statue was his quote, “Knowledge is good.”
After Emil gives us a bit about his background, the guys jump into the deep end. Emil trades managed futures, and while most people think “trend following” when they hear “managed futures,” there are other styles. Emil tells us about a style he uses often, spread trading.
Emil looks at the term structure in commodities futures contracts. There’s a price for every month going out in time. You can trade the differences between those months (calendar spreads). He also trades relative value and roll arb. Emil likes these strategies because there’s tons of alpha available.
Meb pauses to explain a bit for any listeners who are less familiar with all this. He explains exposure to the futures markets, using oil as an example. This leads into a discussion about the growth of commodities markets. Back in the 2000s, commodities went from being just a product to an investment vehicle. So the powers that be created indices and various commodities products to meet this demand. Investments in commodities exploded, driving up prices.
This dovetails into what Meb calls “one of the dirty secrets of indexing,” which is how many indices can be front-run. Meb tells us how, for some 1.0 commodities indices, the slippage was in the order of 3-4% per year.
Meb then asks Emil to describe what he looks at when establishing a position. Is it fundamental? Technical? Emil tell us it’s very important that you use both, because “you have to understand the fundamentals because things change.”
Next is a great conversation about front-running trend followers. This is something that Emil does. He knows that if there’s a big move, the trend followers are likely all on the same side of the position, so when it comes time to roll the front month, and Emil generally knows when that will happen, Emil takes advantage of the price movement. Meb and Emil then discuss the easiest way to implement this strategy.
A bit later, the guys discuss what themes/positions Emil is interested in right now. He tells us how there has recently been a shortage in gasoline, so gas has been running up against crude oil. It’s at high levels now, and Emil thinks it’ll come down. Emil also tells us that he’s looking at grains, the energy markets, and certain metals including platinum and palladium.
This leads into a discussion on oil. Meb asks Emil’s take on the industry.
Emil gives us some great background on what drove oil up so high, and why it crashed. Then he discusses the technological revolution in oil drilling, the result of which is that the cost of finding and developing oil has collapsed. There are some great details in here which oil investors won’t want to miss, but Emil wraps up this part of the conversation by saying “the days of $80 oil – that’s a long way away.”
Meb then asks what areas of commodities Emil likes right now. Emil tells us his thoughts on at what level crude is buy. And he mentions a certain metal which he considers a “no brainer.” You’ll have to listen for the details.
There’s way more in this episode: how Emil views gold in light of new cryptocurrencies… A Twitter poll Meb conducted that reveals just how stubborn some investors can be when it comes to selling out of overvalued equities… Where Emil has seen the most investors make the biggest mistakes over his 25+ year career… The dangerous false belief that “we’ve seen this before” in the markets, and how computerized investing is taking us into uncharted waters… And finally, Emil’s most memorable trade (which was a loser that will get your blood racing).
What are the details? Find out in Episode 65.
In Episode 64, we welcome David Varadi from Blue Sky Asset Management.
David tells us a bit about himself before he and Meb jump into investing. Meb starts by referencing a quote from Blue Sky’s website:
“Unlike endowments, investors do not have an infinite time horizon. For this reason, we believe that a traditional strategic asset allocation approach based on modern portfolio theory is suboptimal. It makes more sense to adapt to changes in the economic environment. We favor a dynamic approach to asset allocation using market information to guide our investment decisions. Most importantly, we believe that a systematic, quantitative approach is necessary to avoid emotions and biases in decision-making.”
Meb’s a fan of all the ideas in that quote, so he asks David to expound and discuss his general market framework.
David tells us how it’s easy to be a buy-and-hold investor when market is going up; much harder so when the market is falling – especially when nearing retirement. Significant drawdowns can be devastating. So David tells us that “managing risk is absolutely critical.” Investors need to be able to adjust their strategies to handle a wide variety of market scenarios – bear markets, varying interest rate scenarios, and inflation. And “if you have a dynamic asset allocation, you have the ability to be more in tune with the market regime that is currently going on.”
Meb asks David to dig deeper – what are the rules and frameworks in place that make his models dynamic?
For David, much goes back to fundamentals, trend, momentum, and volatility. David starts with a strategic allocation that reflects longer-term assumptions. But what’s interesting is how David uses volatility in concert with trend/momentum, helping him know when to be in the market versus cash. Most people think time-series momentum is a binary decision, but David brings probabilities into the discussion.
Meb then asks about the challenges a retail investor faces when trying to implement the strategies David has been discussing.
A big challenge is tracking error. The more dynamic you are (moving away from buy-and-hold indexing), the more potential tracking error. Another issue is how often you trade. David tells us that the investor has to ask himself what is most important – does the investor want to reduce the drawdown in a 2008 scenario, and if so, is he willing to take the tracking error associated with that?
Meb echoes this tradeoff between buy-and-hold versus active. It’s very hard to look “different” than the market and/or your neighbors when you’re underperforming.
Next, Meb references a chart from one of Blue Sky’s white papers that shows the most successful asset managers (presented in our show links). The top three are all quant/trend guys. Buffett is at six. Meb asks why, then, everyone knows Buffett’s name, but most average investors aren’t familiar with the trend asset managers.
David gives us an interesting answer, referencing how trend is less known, as well as the behavioral challenges of its implementation. But he tells us that a big reason why many of those trend investors are on the chart is because “when you stay in tune with what’s actually happening in the market, you’re much more likely to survive over a long period of time.”
It’s not long before the guys switch to a fascinating new topic – using equity option data to select stocks. In essence, looking at the implied volatility between puts and calls to get a feel for which equities are more likely to climb. David is searching for “high implied skew.”
Next, Meb brings up another Blue Sky whitepaper, this one about retirees and risk. David hits the high points, discussing the challenges of volatility in retirement.
There’s plenty more in this episode, including the new areas David is researching… David’s most memorable trade (one involves put options, the other Bitcoin)… And David’s one piece of investing advice to listeners, involving three mental “buckets” for your asset allocation.
What are they? Find out in Episode 64.