Venture Debt vs. Venture Capital Returns

One of my favorite investment strategies is the barbell strategy where I invest in lower risk companies or indices to hit singles and doubles while concurrently investing in more speculative companies to hit potential home runs. I’ve structured my after-tax investments to be more low-risk through structured notes, and my pre-tax investments in my rollover IRA, SEP IRA, and Solo 401k to be more high risk. Given my pre-tax investments can’t be touched until 59.5 without penalty, I find it easier to take more risks with such funds.

My investments are solely a mixture of equity and fixed income to keep things as simple and straightforward as possible. My main goal is to come up with an appropriate asset allocation for my age and risk-tolerance, and let the investments perform as they may. Spending energy trying to beat the S&P 500 is a fool’s game. I’d much rather be traveling, playing tennis, building my online business, or writing with my spare time.

I’ve recently invested into a new investment vehicle I’m very excited about. It’s called venture debt. For those of you who are accredited investors who like the barbell investment strategy as well, I think you will appreciate learning about venture debt in this article.

Dollar cost averaging is the act of consistently investing in a particularly security over a set interval of time. Most like to invest every two weeks or every month since that’s when most get paychecks. For example, let’s say you’ve got $2,000 left a month after you contribute to your 401k and pay your basic living expenses. You invest $1,000 every single month into the S&P 500 ETF, SPY, regardless of whether it’s reaching record highs or going into the crapper. That’s dollar cost averaging.

The great thing about dollar cost averaging is that you don’t have to think too much. All you have to do is not forget to invest, and eventually your financial nut will grow so large you’ll achieve make it rain status. Growing your wealth is all about practicing good financial habits that last over the long run. Sticking with a system of saving and investing will do way more than trying to uncover than unicorn stock for most.

At some point in your life you will either have a financial windfall (year-end bonus, inheritance, gift). There might also be violent corrections in the stock market as you’ll see in a chart below. Given the stock market trajectory over the long-term is up and to the right, you should come up with a framework on how to best take advantage of opportunities in a methodical way.

Here’s how I think about how much to dollar cost average. It’s kind of an oxymoron to “figure out” how much to dollar cost average, but hear me out. Hopefully my framework will help you better deploy your cash. 

Greetings fellow Financial Samurai. Bruce here. I recently dropped a note to Sam about a financial conundrum that I was working through as I appreciate the analytical approach on this blog. Sam suggested that I write it up and engage the Samurai community to help with the alternatives analysis.

Background

My wife and I are in our early 30s, are currently child-free, and live in the suburbs of Atlanta, Georgia. About three years ago we sold the condo we had purchased as our first marital home and bought a suburban house northeast of Atlanta in an area with the best public schools in the city called Marietta.

The house was the cheapest house in the best school district and definitely on the low end of the neighborhood as well. We paid 167K and there were only one or two other homes less than 200K in the high school district at that time. As luck would have it, we just happened to be buying within 30 days of the market bottom in January 2012 for the suburban Atlanta area.

We invested a decent chunk of change (~50K) in renovating the finishes of the home to give in a semblance of the style we like from watching exorbitant hours of “Property Brothers” and other similar shows on HGTV.

After living in this area for the last two and half years, my wife came to me with a proposal that we look into moving further south from the suburbs of Marietta closer to the urban center of Atlanta. She laid out the logic including the following:

• She works closer to downtown Atlanta and her commute would go from 45 mins to an hour each way to around 20 minutes each way
• The neighborhood/area we currently live in is dominated by families and children with very few single couples. This affects making friendships and means we will always be driving somewhere else if we are going out with our fellow child-free friends. Basically, why don’t we live in the city of Atlanta and enjoy the more active community while we have the opportunity? We can always move back to the suburbs if and when we do have a kid and they don’t start into public schools until they are six or so years old anyway.
• The restaurants and bars in the suburbs are typically chain restaurants and sports bars. All the music venues, hip restaurants and bars are in Atlanta

I heard my wife’s impassioned appeal and decided to get on board with her plan to move to the City of Atlanta. I think the part that excites me the most is the opportunity to live in a walkable community. Everything in the suburbs involves getting in a car, but the area we are moving to allows for a ten minute walk to one of the most popular bar and restaurant districts in the city.

When we purchased our suburban house, we had pictured being there for the long haul (probably ten years or so), but with the renovations adding value and the market appreciation we felt confident with the numbers and changing our plans to move in-town.

However, we both agreed that because we have never lived in-town before, we would rent for the first year as opposed to buying a home in the city. The houses in the area we are going to be renting are almost twice as expensive as the suburbs we currently live in, and we want to make sure we are buying in the right area where we will want to settle in for at least 4-5 years so that we don’t repeat the same mistake of moving to an area that doesn’t end up being our cup of tea. By renting a home in the city, I think we will be able to figure out what makes the most sense to buy when we are ready after our 12 month lease is up.

One of the reasons why I’m an Apple user is because I appreciate good service. When I dropped my Macbook one evening and my hard drive stopped working, it was incredibly easy to schedule an appointment with the Genius Bar at my local Apple store. They fixed my hard drive and recovered my data within 30 minutes and away I went. Peace of mind is worth the premium, which is why I’m a fan of technology-assisted financial advisory firms with human financial advisors.

But what if you have time and know how to upgrade your RAM, swap out your hard drive, and do your own diagnostics? (I remember doing all that as a teenager.) Then going the robo-advisor route may very well be a good option because their fees are even lower. There’s just no person to guide you through life’s myriad changes.

Robo-advisors, aka algorithmic advisors deploy sophisticated investment algorithms to help invest your money in the best risk-adjusted way possible. You essentially fill out a profile about yourself and the algorithm will go to work to recommend and implement their recommendations for you.

I used to have a hard time trusting computers to do anything for me. But after spending 13 years covering some of the largest mutual funds and hedge funds in America, it’s clear that algorithmic investing, or more commonly known as quantitative investing or scientific investing have done extremely well. For example, Bridgewater Associates run by Ray Dalio is the largest hedge fund in the world with over $120 billion dollars and it’s a macro quantitative fund with tremendous performance. Famous hedge funds run by George Soros, David Tepper, and Steve A. Cohen can’t even compare.

A good quant fund or algorithmic advisor is all about having good people. At the end of the day, the investment variables are created by people and continuously tested for maximum returns. Spending time understanding people’s backgrounds and then trusting them to do the right thing is a huge part of letting other people run your money. After all, the reason why you want someone else investing your money is because your expertise lies elsewhere, and you’ve got more interesting things to do with your time.

In this article, I’d like to provide a brief primer on the three main robo-advisors that exist today: FutureAdvisor, Betterment, and Wealthfront. Because I’ve personally met Bo Lu, Founder of FutureAdvisor, I’m going to compare and contrast FutureAdvisor to the other two. They are all based here in San Francisco.