1/15: Early stage investors have gotten really creative over the past few years with the rights they’ve negotiated in their deals. But guess what? In today’s market the rights aren’t being honored like the Investors expected. A quick thread on what’s going on and why:
2/15: The issue starts with the nature of the asset class as a whole. Here are a few “facts” about VC investing:

First: The average VC investment delivers negative returns. A commonly sited statistic is that 75% of all VC backed startups don’t return capital to investors.
3/15: Second: Producing outsized returns requires finding right-hand tail companies. If you’re a typical early stage investor, you want to protect or grow your investment because the return profile of follow-ons is better than investing in a new unknown company.
4/15: Third: Many VCs aren’t capitalized properly to protect or grow their position in their winners. A typical early stage fund is structured to build a diverse portfolio to get more “shots on goal” and only write one or two additional checks into their winners at most.
5/15: These three issues have driven the early stage VC community to find creative solutions that theoretically allow them to capture the downstream return profile of their winning investments without needing to upsize their core fund or reserve more capital for follow-ons.
6/15: But in today’s environment, these creative solutions are creating downstream problems and therefore are being re-negotiated or altogether ignored. Paper rights are like paper gains --- counting on them isn’t prudent because they can go away in a puff of smoke.
7/15: One “why” behind the issue is that valuations have spiked. While some startups have simultaneously upsized the amount being raised, this isn’t uniformly true. For many rounds this means that less equity is being sold than in the past.
8/15: Historically, a startup could expect a typical early/mid-stage round to dilute investors/employees by 20-30%. An early stage lead investor is usually looking to buy 15-20% with their check, so there was usually room for pro-rata rights to be somewhat if not fully honored.
9/15: In this environment, early stage investors are encountering situations where the valuation and round size translate to 15-20% total dilution which leaves very little (if any) room for pro-rata. Existing investors want the high valuations but they also want their pro-rata!
10/15: Making this worse are side letters that preserve their pro-rata (or in many cases grant them super-pro-rata rights) even in cases where an investor falls below the “Major Investor” threshold or lets their pro-rata rights lapse for a round or two.
11/15: Many of these investors don’t have the capital to back their rights so SPVs are being raised to cover their allocations. These SPVs don’t always come through and when they do they take time to fill which makes it difficult to close the round.
12/15: And the concept of super-pro-rata is extremely challenging and in some cases quite offensive to incoming investors. Writing tiny early stage checks and then backing up the truck when a winner emerges is the opposite of conviction based investing.
13/15: Why not ask the new investor to own 10% instead of 15-20%? For funds with active investors this is a major ask because each investor can typically only oversee a portfolio of 8-12 companies. Finite portfolio size drives minimum ownership requirements.
14/15: What’s sad is that the completion of a funding round is supposed to be a celebratory event. Instead, they can feel like a wedding where the families are fighting even though the only two persons who matter want to get hitched.
15/15: TL;DR: In today’s environment it’s important to read the room. In oversubscribed situations historical rights aren’t worth the paper they’re written on. Insisting they’re honored is the VC version of a toddler not wanting to share their toys. Just don’t do it.

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More from @fintechjunkie

26 Mar
1/25: We’re witnessing one of the most exciting periods in VC history. Funding is flowing freely, valuations are stratospheric and gigantic exits have become the norm. As a VC this should feel great, but does it? Maybe not. What follows is a rant that bears my soul on the topic:
2/25: Many Investors have offered their insights on this topic, most of whom provide clever narratives that justify what’s unfolding in front of us. I felt that given the huge amount of speculation running rampant I’d share my inner dialogue rather than a buttoned-up perspective.
3/25: My inner dialogue starts with shock, awe and distrust. For those who are new to investing, it’s important to understand that what’s happening in the private and public markets is truly amazing. This isn’t a normal environment and it can’t be easily explained.
Read 25 tweets
19 Mar
1/21: Many people have asked why #Banks can’t just copy #Fintech functionality and then crush them with their scale and advantaged funding and regulatory apparatus. It’s because they’re in the “functional relief” business vs. the “magical transcendence” business. Unpacked:
2/21: While so many Banks want to believe that they can compete with best-of-breed Fintech companies, it’s a **mostly** true generalization that the two factions don’t approach product construction and service delivery in the same manner.
3/21: For any given product or service, Banks ask themselves: “What problem does the customer want us to solve?” and “How can we deliver a solution in a safe and compliant manner?” and “What friction can we reduce in the process that will remove costs and improve throughput?”
Read 21 tweets
16 Mar
1/18: My first post about #BTC and it’s a challenge for the #BTC community:

This🧵details 4 questions that I’m wrestling with regarding #BTC. In full disclosure, I have a very deep understanding of the benefits of #BTC but I’m not yet on board. Help me get there:
2/18: Q1: Having a central currency allows our government to print money for a variety of reasons. While not everyone agrees with every reason for printing money, it does help our country navigate urgent situations that require the government to procure goods and services.
3/18: A good example of this was WWII. The Fed wanted to finance the war with debt as much as possible to spread the distorting burden of higher taxation out over as many years as possible. 40% was paid for with increases in taxes but 60% was funded with debt.
Read 18 tweets
8 Mar
1/6: I've been spending a lot of time this past year thinking about inflation in the US. There are skeptics and there are some that believe the signs and portents are here.

(I think it's already here and that our systems aren't tuned to measure it correctly)

A few fun stats:
2/6: The highest inflation rate ever observed in the US was 29.78% in 1778.

Since the introduction of the CPI, the highest inflation rate observed in the US was 19.66% in 1917.
3/6: The most dramatic deflationary period in U.S. history took place between 1930 and 1933, during the Great Depression.

The closest the United States has ever gotten to hyperinflation was during the Civil War (1860–1865) and only in the Confederate states.
Read 6 tweets
4 Mar
1/33: So you want to be a top performing #VC investor. Here are six exercises you can practice as you evaluate #startups that will hone your skills, establish frameworks, and help identify great investments.

Read on if you’re interested:
2/33: Exercise 1: Describe the company’s magical experience

After reading a deck or hearing a pitch, can you easily articulate who their perfect customer is and how they’d interact with the company’s product/service in a perfect manner?
3/33: Only after you understand the experience that a company is trying to create can you evaluate it against currently available options. If the new experience is truly magical and differentiated then it might be worth your time.
Read 33 tweets
24 Feb
1/25: It was amazing to see the reaction to the thread by @dunkhippo33 about “why ownership doesn’t matter for early stage investing”. There are great nuggets in her thread but I have a very different perspective and counter-argument.

The case for why ownership DOES matter:
2/25: The main argument that @dunkhippo33 makes is that “multiples on invested capital” is all that matters. While this is a truism, the argument glosses over fund dynamics and how much easier it is to produce great fund returns with a concentrated vs dispersed portfolio.
3/25: Let’s start with the typical distribution of outcomes in an early stage fund. Most investments in the fund end up doing “OK” or they completely flame out. The bottom 75-90% of the investments will end up collectively returning 0.5-1.0X to the fund.
Read 25 tweets

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