Tagged: Venture Capital

Empty Spaces on Maps

Prior to the 15th century,  maps generally contained no empty spaces.  Mapmakers simply left out unfamiliar areas, or filled them with imaginary monsters and wonders.  This practice changed in Europe as the great age of exploration began. In Sapiens, Yuval Harari argues that leaving empty spaces on maps reflected a more scientific mindset, and was a key reason that Europeans were able to conquer and colonize other continents, in spite of starting with a technological and military disadvantage.   Conquerors were curious, but the conquered were uninterested in the unknown. Amerigo Vespucci, after whom our home continent was named, was a strong advocate of leaving unknown spaces on maps blank. Explorers used these maps to move beyond the known,  sailing into those empty spaces so they did not stay unmapped for long.

The same phenomenon occurs in business. In the Innovator’s Dilemma, Clayton Christensen shows why large established ostensibly well-run companies so frequently miss out on major waves of innovation.   A key principle in the book is the difference between sustaining technologies, which merely improve the status quo, and disruptive technologies, which offer a new and unique value proposition.  Large companies will frequently focus on sustaining technologies, and ignore disruptive technologies that serve fringe markets initially. Ultimately its disruptive technologies that define business history. Yet complacent companies don’t figure that out until its too late.

Companies whose investment processes demand quantification of market sizes and financial returns before they can enter a market get paralyzed or make serious mistakes when faced with disruptive technologies.

There are two parts to overcoming the innovator’s dilemma:

  • Acknowledging that the market sizes and potential financial returns of a nascent market are unknowable and cannot be quantified  (drawing the blank spaces on the maps) and;
  • Entering the nascent market in the absence of quantifiable data- (travelling into the empty space) 

Analogous ideas also apply to investing.  In Investing in the Unknown and Unknowable, Richard Zeckhauser distinguishes between situations where the probability of future states is known, and when it is not.     The former is the realm of academic finance and decision theory. The latter is the real world.  

The real world of investing often ratchets the level of non-knowledge into still another dimension, where even the identity and nature of possible future states are not known. This is the world of ignorance. In it, there is no way that one can sensibly assign probabilities to the unknown states of the world. Just as traditional finance theory hits the wall when it encounters uncertainty, modern decision theory hits the wall when addressing the world of ignorance.

Human bias leads us into classic decision traps when confronted with the unknown and unknowable. Overconfidence and recollection bias are especially pernicious. Yet just because we are ignorant doesn’t mean we need to be nihilists.    The essay has some key optimistic conclusions:

The first positive conclusion is that unknowable situations have been and will be associated with remarkably powerful investment returns. The second positive conclusion is that there are systematic ways to think about unknowable situations. If these ways are followed, they can provide a path to extraordinary expected investment returns. To be sure, some substantial losses are inevitable, and some will be blameworthy after the fact. But the net expected results, even after allowing for risk aversion, will be strongly positive.

Examples in the essay include David Ricardo buying British Sovereign bonds on the eve Battle of Waterloo, venture capital, frontier markets with high political risk, and some of Warren Buffet’s more non-standard insurance deals.  Yet since even the industries that seem simple and steady can be disrupted, its critical to keep these ideas in mind at all times in order to avoid value traps. 

The best returns are available to those willing to acknowledge ignorance, then systematically venture into blank spaces on maps and in markets.

Investing in the Unknown and Unknowable

See also:

How much due diligence is enough?

“They can’t touch me. I do my homework”
-John Boyd

How much investment due diligence is enough? How much is too much?

The amount of research an investor should do before making an investment depends on three factors: 1) Size of Position 2) Illiquidity of position, and 3) Contrary nature of position.

The Kelly Criterion is a good heuristic, although in real life we never know exact probabilities. Most investments will succeed or fail on one or two factors. The key is to identify those and understand them better then the person selling to us. Anything beyond that is just for fun. Indeed a lot of investors really like to dig. But the 80/20 rule applies. Think jiujitsu not powerlifting.

Position Size

Position sizing is part math and part psychology. The bigger a position, the more a person has to check and double check. This isn’t just a number in a spreadsheet. Conduct a premortem. What is the maximum pain you can take? The only way to survive a large position going against you is to have the confidence in your research.

Its critical not to get causation wrong here. If “concentration” is part of one’s identity as an investor, there is a major risk confirmation bias will takeover and more research will just make them more sure of a false idea. Remember smarter people are actually at greater risk of confirmation bias.

If the facts lineup, it might make sense to “go for the jugular”.


For most individual investors, illiquidity is a secondary concern. Nonetheless an investor must consider it. An investor can easily sell a widely traded stock or ETF. But for illiquid positions, an investor needs to learn that information ahead of time.

Decisions that are easy to reverse can be made quickly. Decisions that are difficult or impossible to reverse require more analysis up front.

Contrarian nature

Markets are usually right. The more out of consensus a view is, the more data and analysis an investor must have to back it up. “Who is on the other side?” is probably the most important question in investing. I’m only comfortable if I understand the contrary position better than people who hold it.

Active investing requires active thinking.

With investment research an hour of active critical thinking is worth more than a week of passive reading

Techniques of due diligence depend on what’s available, and also on an individual personality. Some people are good at plowing through footnotes or analyzing sentiment data, others are highly skilled at interviewing industry experts. Since computers read 10-Ks the minute they come out, its essential to get creative with due diligence, but this does not mean digging for the sake of digging.


I was researching, a venture capital focused business development company (BDC) liquidation. Its investments holdings consisted of preferred stock in 11 venture stage companies, with most of the value concentrated in the top five holdings.

Although there was limited publicly available information on the financial condition or valuation of each individual holding, the filings disclosed the aggregate range and average of the metrics and assumptions used by the company in the valuation process to arrive at fair value of Level 3 Assets on the financial statements. My interest was piqued when I noticed that other public BDCs that owned some of the same asset were marking them at much higher prices. Nonetheless, I needed to verify the viability, and growth potential of the main underlying businesses.

I approached this issue from multiple angles:

One of the company’s largest assets was preferred stock in a company that operated a dating site. With permission from my wife, I set up a fake profile to see how the interface of the website and app worked, and to verify that there were indeed a large number real people using it in my area, and a few other cities I checked. This helped me corroborate information from user reviews I had read.

The company owned stock in a highly specialized medical testing startup. I reviewed the background of top employees on LinkedIn, university websites, and various scientific journals. Additionally I discussed the business idea with friends in academia. They verified that the idea had a reasonable chance of working, and would require an advanced degree to replicate.

Accounting rules gave management ample discretion on how to report the holdings on the balance sheet. I carefully reviewed everything they had disclosed about their valuation process, and tracked changes in language between different filings over time.

I also contacted the management of the BDC, and was able to reach the people in charge of the valuation process on the whole portfolio. They helped me understand the facts they were using to justify the valuations supplementing my careful reading of the public disclosure. The conversation verified that the BDC was indeed serious about liquidating its portfolio. Further they candidly reminded me how valuing the portfolio conservatively made the tax consequences of converting to a liquidating trust more favorable for investors(the management group was also a large shareholder).

I did a lot of unconventional work, but didn’t mindlessly dig for more info. It wasn’t a huge position but since its going to be locked up in a non transferable liquidiating trust, and it was an idea most people thought too ugly, a bit of extra work was justified.

The company already paid back most of my initial investment after selling one investment and the portfolio still has a lot of value. The true test will be in the final IRR when its all said and done.

See also: The hard thing about finding easy things

Cheap stuff and cheap capital

Two main factors drive an upsurge in entrepreneurship: cheap stuff and cheap capital. Cheap stuff is primarily a long run secular trend. Cheap capital is cyclical.

By cheap stuff I mean the inputs to a business, mainly technology. This has gone consistently down over time. One can build a website or an app for a few thousand dollars that is better than what they could have done for millions of dollars a decade ago.

Even if capital becomes scarce, cheap stuff will still be a positive factor driving entrepreneurship.

By cheap capital I mean the flood of venture capital. This is primarily cyclical. Consider this quote:

“There’s so much money chasing these deals that venture capitalists are in competition with each other. They spend their energies marketing themselves instead of screening the deals. It’s gotten silly”

Think it applies today? Or maybe to the late 1990s tech boom? This quote is from the WSJ in 1981, and referenced in this excellent article about 1980s venture capital.

During a boom its easy for most ideas to raise capital, regardless of business viability(as long as they fit with theme of the times). Indeed they can keep raising rounds in hopes of a profit decades in the future. After a bust its hard to raise capital, even for a great idea. Entrepreneurs need to bootstrap and get revenue a soon as possible.

Right now it seems there is a ton of venture capital financing companies that are losing money.

Cheap stuff and cheap capital are partly entangled. You might be reading this from within a WeWork. If they couldn’t keep raising cheap capital you think your rent is going to stay the same? Or maybe you are building a business on top of a money losing social media platform, or somehow benefiting from a thriving open source ecosystem.   On the other hand, its harder to source talent when there is a flood of capital, and certain commodity based goods can have their own production cycle.    Yet you can run your business from a garage and the new inventions of the latest venture boom aren’t going away.

Which is most important- cheap stuff or cheap capital ? I don’t know, but we’ll get to find out when this cycle turns. Creative entrepreneurs will still take advantage of technological improvements to bootstrap groundbreaking ideas, even if they can’t raise venture capital. Sometimes they do it out of choice, other times they do it out of necessity.

Once this cycle turns, we’ll go through a few years where most new businesses have no choice but to bootstrap.

This idea generally applies across all industries, not just venture funded. However in commodity based industries the cyclicality functions differently.  Cheap capital often leads to inflation in hard assets.   See also: Capital Returns: Investing Through the Capital Cycle

Disrupting Through Good Customer Service

In Zero to One Peter Thiel theorizes that a new innovation must be at least ten times better than the currently existing solution in an important dimension. This is a high bar, but it often achieved by focusing on an ignored or under exploited niche.

The examples of Uber, and Amazon show how focusing relentlessly on customers can also achieve this goal, especially when incumbents are attached to an old way of doing things that is unpleasant for customers. Good customer service can be extremely disruptive.

When facing regulatory challenges, Uber’s CEO Travis Kalanick went against conventional wisdom of his lobbyists. Rather than seeking to compromise with regulators, he focused on delivering a better product. In The Upstarts the author discusses what is known as “Travis’ law:

“Our product is so superior to the status quo that if we give people the opportunity to see it or try it, in any place in the world where government has to be at least somewhat responsive to the people, they will demand it and defend its right to exist.”

Mobilizing customers is Uber’s  public affairs strategy.

This extreme focus on customers was a key factor in Amazon’s rise as well. Here is Jeff Bezos in the early days of Amazon(quoted from The Everything Store):

“You should wake up worried, terrified every morning.  But don’t be worried about our competitors because they’re never going to send us any money anyway. Lets worried about our customers and stay heads down, focused.”

Bezos reiterated this sentiment in the most recent annual letter:

There are many ways to center a business. You can be competitor focused, you can be product focused, you can be technology focused, you can be business model focused, and there are more. But in my view, obsessive customer focus is by far the most protective of Day 1 vitality.

Why? There are many advantages to a customer-centric approach, but here’s the big one: customers are always beautifully, wonderfully dissatisfied, even when they report being happy and business is great. Even when they don’t yet know it, customers want something better, and your desire to delight customers will drive you to invent on their behalf. No customer ever asked Amazon to create the Prime membership program, but it sure turns out they wanted it, and I could give you many such examples.

I can’t help but wonder if financial services will end up facing a similar level of disruption from Robo Advisers.  Most of the financial services industry is clearly conflicted and not focused  on actually improving client outcomes. That leaves a massive space for new entrants.

Discounted Venture Capital

I posted on Seeking Alpha about my investment in Crossroads Capital (XRDC), a busted venture capital BDC trading at ~60% of book value, with 70% of market cap in cash.  It has a messy portfolio, but not a lot needs to go right for signficant upside.   For those with the means and/or the investment mandate, getting an NDA and buying the  individual portfolio companies from XRDC might be the better option.  Crossroads Capital hired Setter Capital to market its holdings.  Setter Capital specializes in the fascinating private equity secondary market.

Here are a few residual thoughts on deep value investing in the busted BDC/private equity/venture capital space.

There is a bit of irony in a deep value liquidation play with assets that consist of preferred shares in growth oriented venture capital investments.  Venture capitalists bet big on change, while value investors generally focus on mean reversion, yet as Marc Andreessen pointed out, there are actually similarities between the philosophies underpinning  value investing and venture capital.  Both styles of investing emphasize fundamental analysis, long term thinking, and ignoring market noise, while taking advantage of some sort of mispricing.

The  negative press about declining valuations of technology startups also creates an interesting value investing set up.  Although its true, some questionable companies had previously raised capital at absurd valuations, many startups, including those in XRDC’s portfolio are legitimate revenue generating, growing businesses  that are also often unlevered.  For companies with real products there hasn’t been a dramatic crash. Rather they have continued operating, albeit have had to make adjustments, and have not been able to raise repeatedly raise capital at record valuations.  To quote Matt Levine:  “The Enchanted Forest has gotten a bit less enchanted, a bit more sensible. The unicorns have knocked off the wild partying and gotten down to work.”    Seems like there could be more opportunities out there to buy growing businesses at dumpster dive  prices, by providing liquidity to earlier investors that need to exit.
Venture capital valuation (or anything else level 3 under GAAP) is controversial.   Generally people aren’t actually buying and selling equity at the accounting value.   Ultimately what matters is the cash that can be received upon exit.
Furthermore, the terms of venture capital investment might not always treat outside investors well:
 - Dilbert by Scott Adams

However, a lot of venture capital investments are preferred equity with quite favorable liquidation preferences.    The prospective buyer will conduct due diligence on the operations of the business, and the rights of the particular security.  With an investment in XRDC one can determine the aggregate valuation paid by an outside investor(about 3x EBITDA after subtracting out all the excess cash in the BDC), and can compare valuations with other BDCs holding the same security (top holding is marked over 20% higher by another BDC), but there is limited public information on each individual security. Based on research of public sources, several of the portfolio companies appear to be doing pretty well, but a couple are also in trouble.  My working hypothesis is that the absurdly large discount creates a “heads I win, tails I don’t lose that much” scenario.  However, cherry picking the best companies out of XRDC’s portfolio and buying them directly would be even better.

I look forward to more opportunities like this.