Split the deal to reach for bigger upside

Advice on investing and splitting the deal in order to share risk and reach for rewards that may otherwise be unattainable from Fred Wilson in Splitting The Deal at A VC.  His experience comes from venture capital, but these seems applicable in any type of private investing.

I am a firm believer in splitting the deal, even when the economics (another word for ownership) suggest that there is no room for others.

My personal track record tells me that splitting the deal works. It helps you step up to something that has a lot of risk but also a lot of upside and it brings other people who can add value into the situation early on.

At a time when we are seeing venture funds get bigger and bigger, I am convinced that the hallmarks of old school early stage investing; small fund sizes, small rounds, and syndicates remain best practices

Risk Ratio & Asset Allocation

Continuing on our recent theme of structuring and building stock and alternative investment portfolios, I wanted to share a few thoughts on how risk ratios play into asset allocation.

When assessing any opportunity, it’s important to look at the best and worst case scenario, at least taken to a reasonable degree, then compare the potential gains versus the potential losses to get a risk ratio. Defining the downside is relatively easy stocks by setting stop losses set at a reasonable amount below the investment value.

In alternative investments, it’s not quite as easy as setting a stop loss sell price. To start, there’s the problem of valuing alternative assets. Values can only be considered estimates until a sale occurs, as prices often can fluctuate significantly in private asset sales. That leads to the second problem of a limited market of buyers for alternative assets. Alternative assets are decidedly less liquid than stocks, so when considering the worst case scenario, you need to consider the actual value if you needed to liquidate for cash within a reasonable amount of time. That time changes based on cashflow requirements, type of asset, and other variables that can be assessed on a case by case basis.

The upside is a relative guess for both stocks and alternative investments, though assets like real estate are typically much easier to estimate than a single stock or a single angel investment. In all cases, it’s important to come up with a reasonable estimate of the target value, should everything go right.

From there, it’s easy to get a risk ratio by dividing the potential gain by the potential loss. A high risk ratio means there’s more upside and implies the likelihood is decreased. While true, it’s important to account for how much capital is at stake and know how often you need to be right in order to win.

Working through these numbers before making an investment can help visualize how the investment plays into your portfolio, in terms of capital at stake, the worst/best case scenarios.

For our own investments, we set our numbers at the initial time of investment, then reassess occasionally by updating the target price, market/estimated value, low value, etc in a spreadsheet, based on any new information/developments. By using the spreadsheet, we get a chance to quickly reassess each investment and see how our assumptions affect our portfolio as a whole, potentially triggering other changes, including changes to our asset allocation.


Our own spreadsheet is based on Chris Perruna’s spreadsheets, which he included in a post on Position Sizing & Expectancy. Give that a read for more info.

We’re working on updating our portfolio tracking spreadsheet to work with a combination of stocks, crypto, and alternative investments. We’ll share a template when complete.

Alternative Investment Options

Alternative investing, meant to include anything not traded on the traditional finance exchanges, are enticing to small investors because of the potential for more control and greater upside. This typically comes in exchange for more volatility and/or less liquidity. Essentially, there’s a cost for investing in public markets due to the ease of access and liquidity and alternative investments should seek the investments that may be a little harder to reach and get greater returns.

With that in mind, here’s a few ideas on alternative investment options:

  • Real estate. The biggest alternative investment market. Many different ways to invest from very hands, fix and flip, to passive investments in real estate projects. Lots of potential to use leverage. Many online tools have become available to help investors find projects. Returns often not as good as what can be found by networking for deals.
  • Crypto. New market that went from ~$15 billion to $500 billion in 2017. Lots of potential to invest still. Bitcoin and ethereum have potential. More exciting is new technology will result in some big winners. Finding the best tokens is very difficult. Very risky overall.
  • Forex. Never interested me much as it seems there is always somewhat limited upside. Seems not meant for passive investing but active trading.
  • Peer-to-peer lending. Appears quite risky but have not looked into it much.
  • Angel investing. Many online tools for investing in new businesses. Very limited liquidity. Potential for big gains. Very volatile.
  • Buying businesses. Not necessarily passive, amount can be determined by owner. With right criteria, risks can be mitigated. Some potential for leveraging money. Can result in cashflow or flip for a big payoff.

We’ve already invested in some of these and we’ll look at some of these options in more detail with new posts over the coming weeks and months.