Brad Feld

Tag: investing

I reread Enough.: True Measures of Money, Business, and Life by John C. Bogle over the weekend. I’d read it in 2012 and it had a huge impact on me.

If you aren’t familiar with John C. Bogle, he founded The Vanguard Group, is credited with inventing the index fund and is a spectacular writer (every one of his books is worth reading.) He passed away in 2019 at the age of 89, but I expect his legacy will last a very long time.

I was pondering some things that were bothering me, specifically about crypto, but more generally about current themes around investing. I thought I’d revisit Enough. to see if it helped me work them out. I found my answer in Chapter 2: “Too Much Speculation, Not Enough Investment.”

Let’s start with Bogle’s definition of Investing and Speculating.

Investing is all about the long-term ownership of businesses. Business focuses on the gradual accumulation of intrinsic value, derived from the ability of our publicly owned corporations to produce the goods and services that our consumers and savers demand, to compete effectively, to thrive on entrepreneurship, and to capitalize on change. Business adds value to our society, and to the wealth of our investors.

Speculating is precisely the opposite. It is all about the short-term trading, not long-term holding, of financial instruments — pieces of paper, not businesses — largely focused on the belief that their prices, as distinct from their intrinsic value, will rise; indeed, an expectation that prices of the stocks that are selected will rise more than other stocks, as the expectations of other investors rise to match one’s own.

What was bothering me was simple: the narrative around many things has shifted to the far end of speculating. I don’t participate in this particular type of narrative, but I’m surrounded by it. I don’t behave as a speculator. While I invest in many things, I rarely sell anything until there is a “defined exit,” where I have a very explicit internal definition of “defined exit.”

As someone who has held private company stock in companies for longer than 20 years, been in many situations where there were no exit opportunities until suddenly there was an exit, I understand and am completely comfortable will illiquidity. And the idea of an investment.

I’m completely uninterested in speculating. In the mid-1990s, when I had a bunch of money after the sale of my first company, I bought and sold some public company stocks. I got sucked into giving some of my money to a money manager at Goldman Sachs and one at Lehman. They happily traded equities for me, which mostly just cost me fees in the end, although I covered it all with a crazy transaction into a weird Exchange Fund that GS created in 2000. I put a bunch of Exodus stock I’d gotten from the sale of a company into the fund. Exodus went bankrupt, so my contribution to the exchange fund was $0, but when the exchange fund paid out seven years later, I got 1.5x my investment. The only reason I got to play in the exchange fund was I had the GS account where they were trading stocks, and the guy I worked with offered up access to it. Totally random and completely dumb luck as I would have likely held the remaining Exodus stock I had all the way to $0. In hindsight, even writing this paragraph is more reinforcement to me of my ultimate lack of interest in this stuff.

As I watch crypto speculation expand into retail stock speculation, which then gets amplified broadly by zero-fee trading apps that aren’t really zero-fee and watch the SEC tangle itself up trying to figure out how to monitor Twitter and Reddit accounts of high profile people who clearly are playing age-old promotion games, regardless of whether or not there are actual pump and dump schemes behind their actions, I become extremely bored. This boredom has a layer of annoyance coating it, especially given the extraordinary 15 months of Covid we’ve just gone through.

Maybe as sports come back, some of this energy will shift back to sports. Now that proxy betting online has become essentially real cash betting online, even though the laws around this (at least in the US) haven’t really resolved, and everyone online has figured out how to get around all the rules, the speculating can become called “betting” again. Or maybe “betting” will just become speculating. It doesn’t really matter since they are fundamentally the same thing.

Let’s go back to Bogle. “Investing … adds value to our society, and to the wealth of our investors” and “Speculating is precisely the opposite.”

Ask yourself, “Is what I am doing adding value to our society?”

Enough has three sections: Money, Business, and Life. While I found the answer to what was bugging me in Chapter 2, the section on Life is awesome. The three chapters are:

  • Too Much Focus on Things, Not Enough Focus on Commitment
  • Too Many Twenty-First-Century Values, Not Enough Eighteenth-Century Values
  • Too Much “Success,” Not Enough Character

Bogle completely nails this topic without being preachy, annoying, arrogant, or directive. As writing goes, it’s as beautiful and powerful as it gets. I strongly recommend Enough.: True Measures of Money, Business, and Life, especially if you have enough but don’t realize it.


I regularly get asked where my investing philosophy comes from. There isn’t an easy answer, as it comes from a lot of places, numerous people who influence my thinking (publicly and privately), my partners, and lots of reflection and critical thinking around things that have worked and haven’t worked for me over the past 25 years.

However, one public person who has influenced my thinking for a long time is Warren Buffett. I don’t know Buffett, but I’ve been a fan and follower since college. I read his annual report every year. I’ve also read several biographies on him as well as a bunch of stuff on his long-time partner Charlie Munger (who I’ve learned even more from.)

Last weekend, Amy and I watched the documentary Becoming Warren Buffett. I thought it would be a harder sell to her, but I think we needed a break from binge-watching The Expanse, so she was game to go in an entirely different direction for a few hours. She loved it, which was fun. I liked it a lot also, and, while there wasn’t much new information for me, seeing and hearing Buffett reflect on some things was fascinating.

My behavior is not to emulate Buffett. Nor is it to emulate any of the other inputs I have. All of the inputs influence how I think about things, but I view them as inputs rather than fundamental principles to follow. But Buffett has been – over an extended period – a particularly interesting and stimulating input for me.

As a bonus, his view on philanthropy and generational wealth is very consistent with mine and Amy’s.

If you are a Buffett fan, or just interested, Becoming Warren Buffett is definitely worth watching.


VCs love to talk about Unicorns, where a giant return is possible. Some friends in the impact investing world have recently started talking about generating giant returns by investing in Zebras (such as a nonprofit building in rural Colorado) and Ponies (an immigrant restaurant in Seattle currently using payday lending at 35% for their working capital). While these returns have an economic component, they can also have dramatic impact on our society.

If you are interested in impact investing, I encourage you to join the Impact Finance Center (IFC) and presenting funders The Anschutz Foundation, Zoma Foundation, The MacArthur Foundation, Colorado Health Foundation, and Gary Community Investments at CO Impact Days 2017, Nov 15-17, in Denver, Colorado.

CO Impact Days is a three-day experiential executive education conference that teaches investors and philanthropists how to make their investments more effective and their philanthropy more efficient. It also will connect attendees to one hundred of the Rocky Mountains’ most exciting social ventures – projects, nonprofits, for profits, and funds.

CO Impact Days’ Founder Dr. Stephanie Gripne (recently written up in Forbes, Is This Wildlife Conservation PhD The Steve Jobs Of Impact Investing) points out that we need to stop bifurcating our philanthropy from our investing and start treating our philanthropy as an investment.

Gripne and a growing number of her colleagues are taking Emerson’s quote, “A foolish consistency is the hobgoblin of little minds” to heart. They are working on figuring out a new investment model where we can start investing in the companies, nonprofits, projects, and funds that society needs.

Another voice in the movement is Ross Baird in his new book, The Innovation Blind Spot: Why We Back the Wrong Ideas―and What to Do About It. Ross makes a strong case that we are missing many of our innovations because of an outdated, obscure, misaligned investment model. According to Baird,

“While most communities across the US think in two pockets – the business and philanthropy communities don’t intersect – Colorado is leading the country in one-pocket thinkers. From the way we invest and support startups, to how employees can own and build wealth in companies, to how finance can be used to reshape traditionally philanthropic sectors such as the environment and early childhood education, Colorado is leading the way.”

An article by Jennifer Brandel, Mara Zepeda, Astrid Scholz & Aniyia Williams, Zebras Fix What Unicorns Break, introduces Zebras as an alternative to to Unicorns. And Gripne’s paper, Laying the Groundwork for the National Impact Investing Marketplace, makes the case that the reason we do not have $1B impact funds for nonprofits, immigrants, and women, is not because we do not have $50M of institutional quality of deal flow. Rather, it’s because there is no incentive to create the infrastructure to do the necessary capacity building to find and scale up these investments. Gripne and her team are also working on a new paper to be introduced at CO Impact Days, inspired by the Zebras article mentioned above, “If Angels Invest in Unicorns, do Heroes Invest in Zebras and What About Ponies and Donkeys?”

This conference is not just about Coloradans. CO Impact Days was designed to expand regionally and replicate to up to five other regions throughout the U.S. creating the National Impact Investing Marketplace. Indiana is bringing a cohort of ten community leaders, Washington is bringing five, and Maryland is bringing three. CO Impact Days is the first statewide marketplace for direct investing, and is just Phase 1 of the national model. Gripne and her team (which Andrew Currie, Kathy Merchant, who led Greater Cincinnati Foundation for 20 years and wrote the book on Community Foundations and Impact Investing, and Nicole Bagley, trustee on Arca Foundation, Brenn Foundation, and Sapelo Foundation) have their sights set on a national marketplace, and they want to invite you in on the ground floor.

Last year’s inaugural CO Impact Days led to over 20 impact investments from first-time, direct investors. They included Nicole Bagley’s investment in Silvernest (a tech platform that provides a matchmaking service for the aging population to find housemates and additional income, companionship, or help around the house) and the Kenneth King Foundation’s investment in Colorado Lending Source’s Main Street Character Loan Fund (providing up to $50K loans to Colorado for those of who have a good idea and good character), among others.

In addition to producing CO Impact Days, IFC is also rolling out a new tool, impact investing giving circles, to catalyze new investors and source Zebras, Ponies, and Donkeys. Impact investing giving circles will provide philanthropists and investors with a low-cost, low risk, first safe investment opportunity by using a donation in a pooled donor advised fund (to be hosted by a community foundation, thus supporting their work as well).

IFC plans to pilot these impact investing giving circles in Colorado in the areas of Conservation & Water, Women, Rural Community Investment. Its Food Impact Investing Giving Circle will be piloted in multiple cities including Chicago, Boston, and Denver, with Chef’s Collaborative and an Immigrant & Minority Impact Investing Giving Circle is being launched in Seattle in partnership with Ethnic Business Coalition to refinancing payday loans for restaurants.

To Get involved in CO Impact Days 2017

Register as an Investor: http://bit.ly/2vMVtFb

Register as Community Attendee: http://bit.ly/2gIgQSf

Volunteer to be a Social Venture Judge: http://bit.ly/2gN41tO

Donate to support CO Impact Days & Initiative: https://goo.gl/3282Tg

Join CO Impact Days & Initiative Mailing List: http://tinyurl.com/y76n29ma


The retrades have begun. Since the beginning of the year, I’ve experienced four retrades – two early stage, one growth, and one late stage – and I’ve heard of a number of others.

If you’ve never experienced a retrade, or don’t know what I’m talking about, it’s the situation when you have a firm deal agreed upon or a term sheet signed and are proceeding to closing a deal, when the investor (or acquirer) decides to change the terms of the deal. And, in case you were wondering, it’s always to make the terms worse, not better.

This happens regularly in M&A deals especially with buyers who are buying thinly capitalized companies or ones who don’t care about their long term reputation. It’s very prevalent with buyers who over time get the reputation as bottom feeders and is often something floated during the diligence process to test the conviction of the seller.

However, for the past six years or so, I haven’t seen retrades from VCs or angels investing in companies very often. Occasionally a deal will fall apart in diligence, some famously so, but they rarely have been retraded.

This lack of retrades, however, is not the historical norm. When I started investing in the 1990s, I experienced a lot of retrades from VCs at many different stages. While a term sheet isn’t binding, part of the reason it tended to be long and complicated was to avoid the retrade dynamic and spell out all the terms of the deal explicitly.

In the late 1990s into the mid 2000s, I viewed the risk of a retrade as continuous background noise in any deal – investment or M&A. The notion of deal certainty became important to me and I started spending more time working with investors and acquirers who I believed had a very high likelihood of following through on what they said they were going to do. In contrast, once I found myself being retraded by someone, I noted it and had a higher bar for working with them going forward, since I expected there would be a future likelihood of a retrade if I did something with them.

By the late 2000s, I had stopped being emotional about the notion of a retrade. I viewed it as a normal part of business, which impacted an investor or acquirer’s long term reputation, but was woven into the fabric of things.

And then the retrades more or less stopped. From 2010 forward, the entire VC market shifted into a mode that many describe as “founder friendly.” Investor reputation mattered at both the angel and VC level. Retrades were a huge negative mark on one’s reputation and word got around. As more and more investors showed up, valuations increased, and time to close a deal shortened, there was little tolerance for a retrade, so they disappeared.

As we are now about five months into a broad market reset, both for public and private market valuations, the retrade has reappeared in private investments. The first indicator of it is that it now takes longer for a deal to close. I expect the days of transactions closing 15 days after a term sheet is signed are probably gone for a while. While some lawyers are breathing a sigh of relief, a deal that takes more than 30 days to close often starts to have a little bit of retrade risk. And, when a deal stretches out over 60 days, there’s a lot of risk around deal certainty – both retrade as well as a full deal collapse.

Recognize that I’m talking about investments, not acquisitions. I never saw the retrade dynamic go away with certain buyers and certain type of acquisitions. However, what’s notable to me on the investment side is that the retrade is happening up and down the capital stack.


There will be a downturn. It might be in a day. It might be in a year. It might be in a decade. We have no idea when it will come, but it will come.

I was talking to a VC yesterday who was an entrepreneur in the late 1990s, which we now commonly referred to as the Internet bubble. He was very successful as an entrepreneur and has continued to be very successful as a VC. A VC who has been around for a long time recently told him that you aren’t a real VC until you’ve been through at least one downturn. He commented that while knowing this, it’s hard not to be a cynic when things are going well and he wondered out loud if there was a way to balance optimism and cynicism as a VC. I had a quick reaction about continually being deeply rational about what one encounters, but it didn’t feel very satisfying to me as an answer.

We are in a very positive part of the startup / entrepreneurship cycle. Given that, there is a regularly occurring discussion about whether or not we are in a bubble, or this is a bubble, or is a bubble forming, or some other bubble thing. The conversations devolve quickly into “yes we are” and “no we aren’t.” This is often followed by justifications of positions with a bunch of random data to support the position, where most of the data is either inaccurate, narrowly chosen with huge selection bias, or a function of what the public market guys like to call “talking your own book.”

I have no idea if we are in a bubble or not. And I don’t care since, as an early stage investor, I play a long term investing game, because I have to. I can’t control liquidity or timing, especially when I initially make an investment. The market is going to move wherever it is going to move and is completely exogenous to me so timing it is irrelevant.

I’ve lived through several severe cycles – both positive and negative – as an investor. I’ve had successful companies created and built at all stages of the cycle. I’ve had failure at all stages of the cycle. There are great strategies for success in both the positive part of the cycle and the negative part of the cycle. And you can do completely stupid things that blow up your company in both the positive and negative part of the cycle. While the stage of a cycle has impact on a company, it’s only one factor.

As I pondered the cynic vs. optimist question this morning, I landed on a synthetic view that feels right to me. I was walking around my office looking at my physical book shelves, mostly for words to try to characterize what I was thinking about, and I landed on Andy Grove’s amazing book Only The Paranoid Survive. I bought the physical copy after reading The Intel Trinity (one of the business / history books I’ve read recently) which inspired me to go back and read – slowly and on paper – each of Andy Grove’s books.

Boom – that was it – I’m a paranoid optimist in a business context. As a human, I’m optimistic. I believe in good. I like good. I hope for good. I prefer good. I am hopeful about the future. I love the work I do. I love helping create companies. I love playing with technology. I love seeing amazing new ideas come to life. I love being alive. I hope to live a long time.

But I know that there is plenty of bad out there. I’ve experienced a lot directly in business, whether it’s bad actors, stupid decisions, unintended negative consequences, self-inflicted trauma, passive aggressive behavior, or outright deceit. I’ve made assumptions about what I think will happen only to have my assumptions be completely incorrect, or correct in my parallel universe to the reality that actually ensues. Some of this has been under my control or impacted by my viewpoint while some of it has nothing to do with me in any way, but is like the proverbial elephant that accidentally steps on and crushes the ant.

When I link this to the cynic vs. optimist dichotomy, I’m definitely not a cynic. But I’m not an unbridled optimist that can only expect more positive. And I don’t vacillate between cynic and optimist based on individual situations, companies, or the macro.

Instead, I ignore the macro. I recognize that I have no control over it. I try to use the experience and lessons from the last 30 years of being in business to guide me steadily through whatever part of the cycle we are in. I know the cycle will change and the companies I’m part of will have the opportunity to be successful regardless of the situation. But I also know they have the opportunity to fail. And that’s where the paranoia comes in. It’s a powerful calibrator.

When I reflect on Andy Grove’s leadership of Intel, it was through a series of intense up and down cycles – both within the semiconductor industry as well as the global macro environment. While he leads with the idea of being intensely paranoid, there’s a thread of clear optimism through his big decisions. When faced with brutal challenges, he dealt with them. When there was daylight in front of him, he ran incredibly hard in a positive way to cover as much ground as possible. But he always knew he’d face more challenges.

The next time I get asked the question, “How can you avoid turning into a cynic when things are going well and you know it won’t last forever” I now have an answer. Be a paranoid optimist.


I know I’m getting old. I remember in 2007 when the idea of a super angel appeared, where successful entrepreneurs were suddenly angel investors making 10 or more seed investments a year. This was a “new” innovation that was celebrated with much fanfare.

Between 1994 and 1996 I made 40 angel investments with the money I made from the sale of my first company. I was referred to as an “angel investor” – I didn’t get the super angel moniker back in the 1990s, but I was often referred to as promiscuous.

Every day I’m reading about a new thing in the startup world. Big corporations are splitting in two or spinning off divisions that are being funded by VC firms. The amount of VC investment each quarter is growing, with us now in the $10 billion / quarter zone, rather than the $10 billion a year zone. Strategic investment is in vogue again, with virtually every large public company trying to figure out how to fund startups. Hedge funds are once again allocating big money to private companies and lots of cross-over public company investors are trying to get large dollars into private companies pre-IPO.

What’s old is new again. As we know from BSG, “All this has happened before, and all this will happen again.”

There are definitely new and interesting things happening this time around. If you haven’t noticed AngelList, you are missing what I think is one of the most interesting phenomenons around. And I’m deep in another one, Techstars, which has helped spread the mentor-driven accelerator model around the world.

Every cycle has a different tempo. We are in a very positive part of the current cycle. But it’s a cycle, and we know that by definition we are likely to have too much, and then a correction, and then too little. Welcome to life.

This part of the cycle always makes me uncomfortable. I love innovation, but when things that have been done before get talked about as though they are new, and no one bothers to try to remember what happened, why it happened, and what went off the rails, that’s uncomfortable to me.

Don’t live history, but study it. Remember it. And make better decisions and choices the next time around.


I was on an airplane for the first time for business in a while and when I woke up from my nap I found my self staring at CNBC on the DirecTV seat back display. I never watch CNBC so I was attracted to the talking heads, who were silent since I didn’t have earphones in. I kept thinking I was watching ESPN with all the sports metaphors, blinking lights, constantly changing headlines, and tightly coifed and good looking men talking at me in rapid fire.

Between a headline about Carly Fiorina exploring a run for president and Zebra Technologies equipping all NFL players with tracking devices I noticed one about companies who were raising prices to inflation proof their business. At least, that’s what I thought it said since it flashed up there quickly between a headline about “Steel is on Fire” and then a video of Warren Buffett walking around without a headline so I had no idea why they were showing him.

The inflation proofing headline stuck in my head. We’ve had a very long period of low to no inflation, at least based on the way the government calculates it. While my cynicism around government math and how inflation is calculated is substantial, there isn’t much question that since 2008 capital has been extremely cheap. Fred Wilson wrote a great post titled The Bubble Question a while ago where his punch line was:

It is the combination of these two factors, which are really just one factor (cheap money/low rates), that is the root cause of the valuation environment we are in. And the answer to when/if it will end comes down to when/if the global economy starts growing more rapidly and sucking up the excess liquidity and policy makers start tightening up the easy money regime. I have no idea when and if that will happen. But until it does, I believe we will continue to see eye popping EBITDA multiples for high growth tech companies. And those tech companies with eye popping EBITDA multiples will use their highly valued stock to purchase other high growth tech business and strategic assets at eye popping valuations. It’s been a good time to be in the VC and startup business and I think it will continue to be as long as the global economy is weak and rates are low.

But I think cheap capital is only half of the equation. The other half is ever increasing labor costs across all aspects of the wage chain. When I was in business school in the 1980s, we talked a lot about the productivity paradox. The premise was that computers and automation would drastically improve productivity, making labor less important as tasks were automated, resulting in lower cost of labor.

As the technology industry rapidly evolved, the notion of non-productivity kept coming up. Nicolas Carr’s HBR Article “IT Doesn’t Matter” was probably the capstone piece around this and how companies could take advantage of the commoditization of IT, rather than how IT was a transformative input into companies and societies.

Suddenly, in 2010, technology was disrupting everything and the technology industry was booming. By 2013 everyone was talking about a bubble, even though the companies being created this time around were substantial. Once again, wages for IT employees and computer scientist were skyrocketing and suddenly coding schools were popping up everywhere, to the point that people are now saying that Computer Programming Is a Trade; Let’s Act Like It.

Capital remains incredibly cheap, so it’s flowing into wages. But that’s only at the high end of the market around technology jobs. At the other end of the spectrum, we have the famed jobless recovery with the elimination of massive numbers of jobs that previously existed, especially in industrial and Fortune 5000 companies. While this is happening, we have an entirely new class of entrepreneurs, or self-employed, being created by companies like Uber.

Yeah – this shit is super complicated and it plays out over a long period of time. In fact, it might only be really possible to understand what is happening in hindsight. But the combination of cheap capital and expensive labor has created a very powerful economic dynamic which right now is driving massive innovation across virtually every industry sector around the world.

We know that extremely low cost of capital will not last forever. We know that eventually there will be real inflation again. And we know that wages can’t increase endlessly. I wonder what happens to the allocation of capital, entrepreneurship, and the impact on society when capital gets expensive again?


Last night Amy and I had an awesome dinner at Perla with Fred Wilson, Joanne Wilson, Matt Blumberg, and Mariquita Blumberg. Fred and I have been involved in Return Path for a dozen years and this has become an annual tradition for us when Amy and I are in NYC. At 12 years of service, Return Path gives a six week sabbatical and a pair of red Addidas sneakers as a “get ready for your sabbatical” gift. Fred and I got the sneakers, but not the six week sabbatical.

I sat across from Joanne and since the restaurant was noisy our table ended up having two separate conversations going. Joanne is awesome – if you don’t read her blog, you should start right now, especially if you are interested in NY entrepreneurship, women entrepreneurs, food, and the thoughts of an amazing woman. I still remember meeting her for the first time around 1995 and thinking how dynamite she was.

Oh – and if you are a seed stage company in NYC looking to raise money, you are an idiot if you don’t immediately reach out to Joanne and try to get her involved. She is one of the most thoughtful angel investors I’ve ever met.

We talked a lot about seed stage investing during our part of the conversation. Joanne has done about 25 investments in the past few years and has a very clear strategy for what she invests in. She works incredibly hard for the companies she invests in, is deeply passionate about the products and the entrepreneurs, and clearly loves what she does.

During the conversation we had a moment where we were talking about feedback. I told her about my approach of saying no in less than 60 seconds. She told me a story about giving entrepreneurs blunt feedback in the first meeting, which I always try to do also. And then she said something that stuck with me.

Joanne will often start a meeting by saying something like I give you permission to hate my feedback. You can decide that you want to tell me ‘fuck you’ after the meeting. But I’m going to tell you what my direct and honest reaction is.

Now Joanne is a New Yorker through and through. Aggressive, direct, and clear. But never hostile. Ever. And a deeply loyal supporter. So this feedback, while direct, is incredibly powerful. It’s often extremely hard for someone to hear, especially if they are in “I’m trying to convince you to fund my company mode.”

I play the same way. At Foundry Group, one of our deeply held beliefs is that we always be intellectually honest, no matter how difficult it may be. At TechStars we pride ourselves on providing direct feedback, but always saying “this is only data”, letting the entrepreneur make their own decision about what to do.

These are versions of Joanne’s permission to “hate her feedback.” It’s a powerful way to frame any discussion. And I know I’ll be using the phrase “I give you permission to hate my feedback” many times in the future.


We describe Foundry Group‘s behavior as “syndication agnostic.” When we make an investment, we are completely agnostic as to whether or not we have a co-investor. This is true at early stages but also true at later stages. We make our own decisions to invest, or not to invest, independent of what other investors are thinking. As part of this philosophy, we’ll lead follow-on rounds for companies we’ve already invested in, including those making great progress where we will lead an up round that we price. We aren’t looking for outside validation from other investors of any sort – either positive or negative. Because we are syndication agnostic, we are delighted to work with great co-investors and welcome and encourage the interaction and partnership. But we don’t have any dependency on it for our decision making.

I saw two important posts this morning – one by Fred Wilson titled Social Proof Is Dangerous and one by Hunter Walk titled The Death of Social Proof. Both are worth reading along with the comments. Naval Ravikant, the co-founder of AngelList, also has a thoughtful comment on Hunter’s post, although I disagree with some of it.

For me, the essence of the conversation comes back to making your own decision as an investor. As an angel investor, I invested in many things and passed on many things. As a VC investor, I invest in a few things and pass on many things. When I look at what drives my decision to invest, it’s the entrepreneurs and the product. It’s never the existing investors, even if I like working with them. When I look at what drives my decision to pass, it’s the entrepreneurs and the product and occasionally the existing investors if I simply don’t want to work with them.

Within Foundry Group, we use a qualitative process to determine whether we are going to invest in something. Once we are actively engaged exploring an investment, all four of us independently interact with the company (although this may happen in groups of us.) To get to this point, it’s going to be a company we likely would invest in. However, we can only invest in about 5% to 10% of the company’s we see that reach this point based on the size of our funds, our tempo, and our deal flow. So we pass on 90% – 95% of companies that “we’d like to invest in, but for some reason don’t get there.”

The reason is almost always qualitative. If the sentiment from one of us trends down during the evaluation process, we immediately pass. This sentiment is driven by our individual interactions with the entrepreneurs and their product. But we each make our own decision, and a single qualitative negative trend causes us to pass. We make mistakes often – there are plenty of companies we pass on that in hindsight we would have liked to be investors in, and in some cases we get a second change and invest in the next round (Fitbit and SEOMoz are two that immediately come to mind.) We always offer to be helpful to the entrepreneurs if they get to this point – some take us up on this. But regardless, we aren’t looking to other investors, or “social proof”, to drive, or even influence our decision making.

This is especially powerful for follow-on rounds. We leave it up to the entrepreneurs whether they want to go find a new investor or not. We express our opinion early in the process and are supportive with whatever the entrepreneur wants to do. If we are going to invest regardless, we’ll make a commitment before the fundraising starts so the entrepreneur knows it is there, even if he isn’t able to attract an outside investor. And, if for some reason we aren’t going to invest, we are clear about it upfront.

I’ve found this interaction to be fascinating with other VCs who are our co-investors. Some are very comfortable with this approach and, as a result, we are attracted to working with them over and over again. Others aren’t, but aren’t offended by our approach, and, since we don’t need them to commit to co-invest along side of us for us to follow through on our commitment, tend to be thoughtful about what they want to do. And some don’t like this approach, although we rarely find this out until we’ve worked with them at least once. When we encounter this kind of situation, we tend not to seek them out as co-investors in the future.

All along the way, we try to be painfully clear with the entrepreneurs that we are making our own decision, independent of the behavior of other investors. This has come from many years of seeing “the investor syndicate” make bad decisions either in the case of a successful company (where they don’t lean in) or an unsuccessful company (where everyone keeps dragging each other forward to “one more round.”) We’ve evolved a deeply held belief that we need to make our own decisions, independent of everyone else, communicate them clearly, and move quickly one way or another.

I’ve tried to scale this personally to my whole life. I don’t really care what other people think – I just try to do my best all the time and learn from everything I do.  I describe that as being intrinsically motivated by learning. Sure – I listen to all the feedback I get, but am mostly looking for content, especially content that I can use to improve what I do (and learn from). Praise and validation go in the same bucket as social proof for me – I appreciate it but ignore it.

Are you making your own decisions?