Reflecting On The First 100 Investments

As I begin Haystack III, I wanted to write down and share the reflections I’ve had on seed investing to date. However, please note (1) I’m still learning; (2) I’ll make new mistakes; and (3) these reflections are for me, and not generally applicable to others — there are 101 ways to invest effectively and different things work for different people. And, ultimately, (4) it is a privilege for me to be even just a small investor, and it’s a privilege I take seriously, and am grateful for all the investors in my fund and founders I’ve gotten to work with — they have all taken a chance on me, and that is a very humbling set of circumstances to keep in mind.

With that, here’s what I’ve been reflecting on with 100 investments now in the portfolio, three years in. I don’t have a technology or investment background, so I wanted to invest in a lot of companies quickly as a way to speed up my learning, but I know in the back of my mind, there are no shortcuts and will be more learnings in the years to come. [I want to dig into some my stats (as I’ve shared on Twitter before), but I’ll do this in another post, as here I want to focus more on what I’m taking away as I move into Fund III.] Finally, I’ve had a tough time organizing my reflections in specific categories, so this may ramble a bit. Apologies in advance.

1/ Out Of Market, Out Of Mind
I made a small handful of “out of market” seed investments, some in LA, one in Canada, a few in NYC, one in Boston, and one in Europe. While I’ve been active with them, it is hard to keep in touch and requires a lot of extra work and communication. For Fund III, I’ve elected to keep my focus to invest locally in the Bay Area. I’m sure it will be tested over the course of this fund, and lo and behold, I met an entrepreneur with operations in Israel and parts of West Africa that I would love to work with, but I am not sure about the geographic divide. At the Series A level, I can see how a VC firm would invest out of market, but at the seed stage, I believe the financing risk is too high generally. I sense some people will take offense to this stance, and I hope local seed markets flow to other geographies. I know I’ll miss out on great opportunities, but for this fund, I’m OK with it, which brings me to the next section…

2/ I Can’t See Everything, And That’s OK
At the seed stage, there’s just no way to see every good opportunity. Company creation is so pervasive, I am not sure how wide one’s coverage at seed could be. By adopting more process constraints (like focusing on local investments, etc.), I’m implicitly saying it will OK to not see a company in another market or in a hot category, etc. It’s OK.

3/ Existential Risk Rules The Day
“Only the paranoid survive.” Or, any similar phrase will do the trick. Seed-stage companies biggest risk isn’t competition or a large company — it’s surviving, and often that comes down to securing future financing venture capital. Every seed stage company, whether they admit or not, strives to “reach Series A,” but we know most don’t make it, so we have an explosion of bridge rounds, or second seed rounds, or seed extensions…whatever you want to call them. While a select few companies will have VCs chasing them or boast insane metrics, the rest have to really fight it out, and it often requires a level of risk, sacrifice, and paranoia among the team to get the deal done, which brings me to the next section….

4/ Founder-Market Fit And Startup-Founder Fit
I have learned that I like to find some connection between what a founder is working on today and what they’ve experienced in the past. It could be a loose connection, but I strive to understand what those connections are and how deep they may be. It could be how they’ve been trained, or where they’ve spent their careers, or it could be personal like where or how they grew up. Additionally, I try to evaluate through conversation and reference checks the level of dedication one has to startup life — Do they have the willingness to take real risks, even if it’s reputational risk? Are they willing to sacrifice in pursuit of their goals? Do they exude a mix of confidence about their abilities and competitiveness to fend off all the copycats that will emerge in today’s startup culture, alongside a healthy paranoia that drives them to understand the next round of financing will be an uphill battle? Speaking of uphill battles…

5/ The Seed Round Doesn’t Really Count Anymore
Receiving an offer to invest early in the life of a company generally doesn’t mean much. Yes, it’s very hard to raise money, but there are so many seed stage financings every day, why announce them or view it as some kind of validation? It is not. Securing a seed round means a team has convinced others to believe in their potential. That is something to be proud of as the recipient, yes, but perhaps more of an internal high-five to one’s self versus broadcasting it to the world. I think what really matters are: Do friends and former colleagues want to work at your new company? Do customers find you and bring business your way? Does your product or service change the behavior of your users or customers in meaningful ways? Do any or all of these exist in your company to the point where a professional investor fights to invest in your company, to join your board, and to work with you on a long-term project? Those are the things that count in the long-term.

6/ What Does “Value-Add” Mean At The Seed Stage?
I’m a very small investor on the cap table. The biggest area seed stage companies ask for help with is, unfortunately, one area I can’t really help much on: Recruiting. Now, I have certainly sent a few ex-colleagues to startups in my portfolio and try to do more when I can, but as a percentage it’s pretty small. I’ve also helped “close” many candidates who are looking to join portfolio companies, which is definitely more effective for me. After a while, one kind of glosses over the standard requests like “Hey, if you know any good iOS engineers, send ‘em our way — we are hiring!” I didn’t want to turn into a recruiter (though I think it’s a very valuable skill), and I believe the talent fragmentation in today’s SF/Valley startup scene is so pronounced that being effective at this may be a waste of effort. Instead, I choose to focus on mitigating the risk in Point #3 above, and from that lens, everything flows.

7/ Being Helpful Via Push Versus Pull
With a larger portfolio and being so early, I initially decided to be available and approachable when someone needed any kind of help or just someone to talk to. To encourage this to happen more casually, I set a calendar alert to BCC email all the founders together on the 1st of the month with a short note to tell them what I was up to, to share where I was speaking, to share generalized opportunities I came across, and to add my phone number. From those more casual emails, conversations would emerge. And as those conversations progressed, I would start to ask about burn rate and runway, and if I gathered that the founder was potentially underestimating how much runway they really had, I would offer to work together on it. Many took me up on this offer. Some didn’t. There will be a higher number of things that don’t work at seed, so I focus on (1) trying to pick well prior to selecting an investment and (2) being in a position to help if it’s welcomed, but then not pushing beyond that. It is not my company.

8/ Investing Pre-Product Or Pre-Launch
Unless I know the founders previously on a personal level or it is someone who has successfully started companies in the past, there are way too many good investment opportunities on my desk for me to consider investing in someone’s concept or dream. In fact, I’m shocked how many people waste time trying to pitch someone about their concept when there are live products in the wild for investors to play with and test. It does feel a bit like people view this very early stage investing as a newfield area to go after, but to me it looks more like grant funding — now, there’s nothing wrong with grants, assuming those grants are made on some type of asymmetric information and/or prior evidence of application of talent.

9/ Leading Rounds Versus Catalyzing Rounds
Being a small investor, I cannot lead a round by investing the most money. However, on occasion, I have been one of the earliest investor in a seed round and then worked to catalyze the round by sharing it with a network of investors who enjoy co-investing with me from time to time. In these cases, so long as the founder is OK with it, I can have a bit more influence on the overall terms (what I think the clearing price will be) before sharing it with the wider network. This has been very successful to date — for both investors and founders I work with. Keeping in line with my views on the threat of existential risk, I focus on catalyzing rounds to make sure they get done versus trying to lead them with the small, inexperienced checkbook I wield. And, as seed rounds are never really closed and therefore this is rarely true urgency around closing a seed round, it is entirely manufactured without real teeth as founders may need bridge capital later on in the company’s life.

10/ The Good And Bad With Party Rounds
I have no clue, statistically speaking, if party rounds impact the trajectory of a company. It is intuitive to think that they do, given that more investors with a smaller share won’t care as much about the company, but then you can see some companies on AngelList which have over a 100 direct investors (not through a Syndicate), and it makes you wonder. Clearly for a founder, managing more lines on the cap table can be a pain, but ultimately, if every seed stage company faces existential risk, and if there are too many investors such that no one has meaningful enough ownership to care for and fight for the company in hard times, that composition may impact how the company fares. Philosophy aside, most rounds I see are split between having 1-2 leads with a few individuals and pure party rounds where the founder just scraps to get it done. For now, I’ve decided to focus on making the sure the round can close if I have conviction versus trying to make sure there’s a lead, though some cases definitely require a lead.

11/ Seed Investors Not Updated Often
I struggled with this initially, because one assumes people will update you. But, most don’t. I’ve learned to accept it for now, and if someone contacts me later for help, I may ask them for more context and an update in order to properly help. Some of the best-performing companies rarely or ever sent an update, despite the investor feeling he/she may want one.

12/ Conflict In Seed
Big VC firms can’t really invest in more than one company in a category, but some get away with it. Incubators and accelerators definitely can, and they take advantage of it. At seed, things are so early and people change course often, a seed investor with a larger portfolio can sometimes fall into a conflict. This has happened to me. On some occasions, there is a direct conflict and I don’t engage; sometimes it’s possible, so I try to ask current founders if it’s OK for me to talk to another company; and the tricky part is that sometimes I don’t see it at all, only to find later that a founder views a company as competitive. Things are so uncertain at the seed stage, I just try to be as honest as possible, but I am going to make mistakes here and have, though I’m not sure what I can do about it given how the market is evolving. At the end of the day, everyone is in conflict with everyone else.

13/ Seed Is From Venus, Series A Is From Mars
Oftentimes, all of this activity gets lumped into “venture capital.” It is not quite accurate. The lessons I’m trying to learn don’t all apply to Series A, which is much more of a zero sum game where investors have to enforce discipline on the system, where they can’t invest in more than one company in a category. (At seed, there is a bit more room to invest in a category, as I described above.) So, I’m hoping people don’t take this post as a proxy for what large VCs do — it is not. Seed is very different and this post can’t be extrapolated to other stages of investment.

14/ On Relationships With LPs
I wrote a series about posts this past summer on StrictlyVC about my experience in meeting, getting to know, and taking investment from LPs. You can read those here. Ultimately, traditional investors in VC funds like to write bigger checks than small funds can provide room for, and increasingly, many of them are looking to make follow-on or even direct investments in the portfolio companies of their managers. This is especially true at seed, where access to companies proves to be most difficult for larger investors to stomach. I learn more about the market, about LPs, and about myself each time I go out to raise — this time around, there were two surprising things: (1) Some LPs first move in diligence was to verify that I actually had a fund and that the fund held previous investments — I had no idea they would do this, but it makes sense; and (2) that no matter how well you think you can pick them as an investor, people will always question your deal flow and judgment. People will question how repeatable your previous record is, and they’ll want to dig into how you get deal flow, which is likely the same way everyone else gets into the flow of deals. As the manager of a small fund, for better or worse, I’ve chosen to meet as many LPs as I can and go into each conversation assuming what I’m doing is too small for them and to focus on building a relationship with them. I’m hoping that over the long-term, with time, that I can build organic trust with a small group of partners.

15/ Investment Pace Matters
This is a learned skill. When I started, I was bad with this, and it got worse being a one-person shop. I got a LOT of feedback on that, and I listened to it — the main change I made is that I have found someone to manage my back-office accounting who is very strict about setting a pace and sticking to it. For Fund III, to start, I can do two wires per month, and he has to have all the docs in place before initiating the wires — then I go into the account and approve them. It’s still my decision, but that little extra process helps with the pace. At seed, the temptation is to make lots of investments because no one is sure what will happen, but from an institutional LP point of view, LPs definitely look over your track record and try to measure and predict how selective an investor can be. Pace is a big part of that equation. Still, two a month for Fund II is still pretty high, but a slow down for me relative to prior funds.

16/ Deal Flow, The Mother’s Milk
Everyone wants to know “How does one get their deal flow?” It’s all the same, everyone is connected to everyone (for the most part), and if you’re seen as a good actor and valuable in some small way, people often share their deals and/or people make introductions. When there’s lots to choose from at seed, picking the right companies becomes more of a challenge, and those who have picked well may do so out of luck, out of process, or some combination. It’s very hard to say.

17/ The Biggest Mistakes I’ve Made: Weighting Concepts Over Market Timing
The most common mistake I’ve made to date (there will be more!) is being seduced by a concept and weighting that over even little signs of momentum in the company or sector. From afar, it’s easy assume investing like this as “people who invest in the future,” but for it to be effective (e.g. to return investments), the size of the market and the market timing are critical, especially when there are hundreds to choose from at any given time. Now when I’m evaluating an investment, I’ll try to find the overlap in a venn diagram of three circles: (1) Is the market huge and evolving in dynamic ways over the next 3-5 years? (2) Is the product or service being offered in that market compelling and defensible in some way (could be based on tech and/or people)? and (3) Do the founders, either veteran or first-timers, have a combination of skill and willingness to sacrifice to make a run at building a company? If the answer is “yes” to all three, then I dig in more for references and socialize it with my close network to get feedback.

18/ Counterintuitive Advice That Backfired
This is easy. I seeded a company earlier this year that started to pick up traction, much to my surprise. The founders immediately turned around and said they wanted to raise a Big A, but summer was approaching, so I shot back with “raise from big funds in the Fall, it’s hard to get a competitive process going in the summer.” Well, that was definitely the wrong advice I gave them, and I pushed it pretty hard. They completely ignored it, and they got their round done before Labor Day, and given how the market reacted then and thereafter, they were absolutely right. Lesson learned.

19/ Reputation, Not Money, Is The Currency
It’s easy to observe the ecosystem and assume all investors have tons of money. Well, many of them do, and even those that don’t write big checks. It’s a great job, no doubt. But, if everyone has money, and all that money is the same color and has the same worth, what differentiates it? Reputation. Reputation, it turns out, is the only real currency most investors have. In a competitive environment, reputation lets an investor see a deal he/she shouldn’t have, or lets an investor convince a founder to work with him/her, or lets an investor be a little extra persuasive when trying to coach a founder. It’s easy to assume investors are conferred power by virtue of having money, but the money isn’t always there and can go away for the next fund — reputation is the real currency, one that takes years to earn and can be washed away in an instant.

The Story Behind My Investment In OneConcern

I am very proud the announce the first investment of Haystack III: OneConcern.

I met the founders through another friend at a fund, he was looking at the company and knew that I liked software plays that sold to national, state, and municipal governments. Most investors don’t like those sales channels, but I do. Why? Because I believe over time the budgets for certain things (health, emergency, climate) will balloon to meet societal needs while many others will fade and erode because we simply won’t have the money in the tax base to get it done. Those essential tasks then will have to be left to technology and software, and in my investing, I’ve found that once an entrepreneur figures out how to sell into governments and builds the right stuff, it is one of the best channels out there because words spread through different networks and it’s harder for a new entrant to cut in.

Anyway, I met the CEO at the request of my other investor friend, and I was immediately captivated by his personal story and academic background. The CEO, a structural engineer from Asia who came to Stanford to study the science behind earthquakes and other natural disasters. This is a tangent, but I enjoy studying the history of earthquakes and learning about how societies have dealt with them. I troll Wikipedia to give my brain a break and read up on these things, so when I met the CEO, I was actually excited to talk about big earthquakes and data, etc. What I came to understand from that meeting, however, was even deeper.

A few years ago, during the major floods in Pakistan, Ahmad (the CEO) was home visiting his family and was caught in the floods. He escaped to the attic of his family’s house and lived on or near the roof for over a week until he was rescued by authorities. I always ask a founder about how past experiences may shape future activities, but I never expected a machine learning engineer focused on building software to help states mitigate disaster response systems say that he himself was caught in a major natural disaster.

If you want to learn more about the company, OneConcern, you can read about them here on New Scientist and here on their website.

While I always try to spend time “in diligence” and vetting a company, I realize now in retrospect I probably spent too much time doing that with OneConcern. The beauty of investing at the seed stage is that I can work with tons of other investors to support companies who start out and have ambitions to grow bigger. Yet, much of the early stages — myself included — have become professionalized, often to the point of placing unrealistic expectations on new companies, new technologies, and new founders, when in fact it should just be about the identification of earnest talent and the relentless support of that talent. I may have conducted my proper diligence, but some things don’t need diligence; a product like OneConcern and an entrepreneurial story like Ahmad’s must be supported — it must be willed into the world, and just like I am trying to do with the creation of Haystack and my own family funds, it will be willed into world no matter what. The solution must exist, and the network of other investors will support it to see it through with their own sweat and passion. That is inspiring to watch unfold and be a part of, indeed.

Clarifying Recent Posts And Tweets

Strong tweets, loosely held. I use Twitter as a dump zone to crystalize my thoughts around a topic in a specific moment, and it’s awesome that people read them, interpret them, debate them, and disagree with them. Lately, I’ve felt that either I didn’t use the most precise words and/or some of the interpretations of my words distorted the whole point I was trying to make, so rather than do that via Twitter, I thought I would briefly try to explain my point of view on three topics below:

On the “VC Drought” post:
A few days ago, I wrote a post titled A New Kind Of Draught In Silicon Valley, which ended up being widely circulated and cited. Many who shared it on Twitter concluded that VCs weren’t investing as much; that’s not quite right, they still are, but it’s not like the summer, for sure. Also, announcements that are made now were likely closed before Labor Day, so there is a lag in the press about funding rounds. I also fielded quite a few media inquiries, and most of the reporters tied my comments as a reaction to valuations. That is a bit distorted. My main point in writing this post was to highlight what many LPs have told me, which is: They see a lot more money going out of their accounts versus coming back in. That lack of liquidity concerns them, and many of them have encouraged their VCs and GPs who managed their money to be a bit more cautious about investing more before returns start to come in. Just like startups, funds have runways, too.

Facebook As A Trillion Dollar Company:
Open this thread to see quite an interesting debate re: the future of Facebook. My two cents is that Facebook is, relatively speaking, underrated as a company and can execute at the highest level, so much so that I see the network growing to one day become a trillion dollar market cap company. Many people on Twitter countered that this is how things felt with Microsoft back in the day, or more recently with Google, and that something new we haven’t thought of may come along to disrupt Facebook. While I agree new things will always come along, I’d hold to my argument because (1) Facebook own’s the most premium, dominant suite of mobile software on the planet and (2) for any new mega-trend that’s emerging to challenge for Facebook’s relevance and attention (VR, Asia, AI, deep/empathetic web, social commerce, bringing the next 3b people online, video, etc.), Facebook not only has an answer, they are either right on or leading the cutting edge. They are distributing mobile software at a time when mobile is not only the largest market in the world — it is also growing.

Charisma In Fundraising:
The latest twisted war of words was today, when I tweeted that “Most assume “the next round” is usually a function of metrics, milestones, etc. when in fact it’s mostly driven by excitement, charisma.” I didn’t realize it at the time, but I believe now that the word “charisma” can be interpreted by many to have some negative connotations, in the sense that it implies by being “charismatic” that one is being inauthentic or fake. Let me state the obvious to be clear that I would never call for anyone to be disingenuous or to fake their enthusiasm like this. I hope that is obvious. Now, re-reading the tweet, if we substitute charisma for something longer like “genuinely engendering excitement about your company, product, service, team, and vision,” well, I would hope that would be OK. Ultimately, this distorted my overarching point, which was to point out in my experience (biased sample, yes), people who were pitching investors to partner with them largely overweighted the importance of metrics and drastically underrated the importance of genuinely conveying the excitement, the meaning, the passion, the vision to the point where their audience (investors) would actually get excited — I mean “excited” in the emotional sense in that they would even start to use emotion over logic to pursue an investment and partnership. The truth usually rests in the middle, and by that both are probably critical to an effective pitch. I just wanted to point out how so many people don’t give enough weight to that side, and how in my experiences, those who can get others (including investors) excited about the opportunity seem to be more successful in receiving larger investment offers.

An Evolving Relationship Between MicroVCs and LPs

This past summer, I wrote some columns on StrictlyVC on the relationship between LPs and VCs, and I realized I never cross-posted them here, so here goes. I reposted them here with subheadings. This may not be of interest to the regular reader, but really intended for venture investors and those who are limited partners in VC funds. Would welcome any feedback or commentary on the notes below, thanks!

Part I: LPs Investing Directly Into Startups

In the few years I’ve been able to meet and learn from limited partners or LPs (those who invest in VC funds), I have noticed an increasing desire to co-invest alongside their general partners. This makes perfect sense. If I was an LP, I’d want to co-invest, as well. Yet, in the process of doing this over the past few years, I’ve found myself repeating some warnings to LPs who have grown eager to do co-invest at the very early stages of seed.

Typically, I cite three key warnings:

One, oftentimes the founders want to meet all potential investors who will be on their cap table. Even though a VC can offer syndication to the founder, that founder may not welcome the introduction and prefer to control the process him/herself. LPs can certainly ask for insight into a GP’s processes, policies, and histories around creating co-investment opportunities, but they cannot be guaranteed. Furthermore, what if a GP has two or three LPs interested in co-investing but there’s room for only one or two. How is the GP supposed to decide?

Two, when there is a real co-investment opportunity for an LP, sometimes the LP doesn’t have the proper resources at hand (domain knowledge, or network, etc.) to independently vet and diligence the specific deal in a few days. If the LP is a family office, they may have enjoy the latitude to quickly stress-test their network and then make a yes/no call; if the LP is a fund of funds managing other institutions’ money, they may have an incentive to seek these types of deals out given their fund economics, regardless of engaging in proper diligence.

And, three, whenever someone is the recipient of an investment opportunity, one should ask: “Why I am so lucky?” In a competitive deal, I often have to fight just to wedge in, and I am not always successful. These are the investments LPs would love to participate in directly as a co-investor, but such opportunities rarely surface. Yes, there are companies that go unnoticed for months or years before breaking out and becoming a sensation, but those aren’t a monthly occurrence.

Again, if I was an LP, I would want to co-invest. After all, LPs are looking for outsize returns, just like the rest of us. More, if an LP doesn’t get in at seed, the bigger VC firms won’t create room for the LP down the road. Still, I’d welcome more conversation and debate around this topic, both from GPs and LPs alike, so that we can all learn more about best practices learned and minefields to avoid. Dangling the opportunity to co-invest may help ink a commitment, but in practice, all that glitters may not be gold.

Part II: The High Cost Of Small Checks

Naively, one of the most profound lessons I had to learn in attempting to raise funds from limited partners is that most institutions prefer to write large checks. By “large,” I mean commitments to VC funds that are equal to at least or oftentimes two to three times more than what a typical decent startup may raise in its lifetime. It is all rational. The time, attention, diligence, legal burdens, and administrative headaches of doling out smaller checks to more funds reduces a larger institutions’ ability to concentrate and, frankly, creates a roster of more egos to manage over a long period of time.

An LP friend and mentor of mine summed it up perfectly to me: “Semil, I like you, but you gotta understand, my friends don’t get out of bed unless they’re writing a $25 million check.”

To those who haven’t raised funds or been around fund formation, it can all seem inefficient. For the rash of micro VC funds that have formed (mine included), we collectively confuse, vex, and overwhelm traditional institutions, including because of our higher pace of investing, heavily reduced levels of ownership, lack of toothy pro-rata rights, and a host of other issues.

Luckily for micro VCs, it doesn’t really take that much money to get going. My first fund was $1 million. It was really hard to raise. Some people have access to wealthy folks, family offices, or corporations, but it isn’t a slam dunk to raise a small fund. The second fund was considerably bigger (relative to the first), yet was still too small for institutions. The third fund will be even bigger — perhaps just at the size where the larger institutions like to build a relationship and track, much like a large VC firm who drops a $100,000 check into a company with the hopes of monitoring its progress.

As other non-traditional LPs (companies, high net-worths, and even funds) have stepped in, it’s created a boon for entrepreneurs. People with the right networks and halfway decent concepts can raise as little as $1 million in a month, even in a category where every early-stage investor knows there are four or five nearly identical competitors working on the same thing. Many of these attempts won’t go on to raise traditional venture capital, and the institutional LPs know that.

So, while there’s a high cost of writing so many small checks, we will have to wait a few years still to see just how costly it is. On the other hand, the cost of starting up may, in fact, decrease during any kind of correction as talent becomes less fragmented and major cost drivers (rent, salaries, benefits) decrease. Founders who are in demand and who are dilution-sensitive may want only specific people on their cap table, and they may want $100,000 to start, not $10 million or even $1 million.

We are a few years away from that, but this is where I see the trend headed — that being nimble enough to be invited to the cap table is what will define individual investors and firms. Those definitions can’t really be bought with money, and that’s what will make the next wave of micro VC investing so interesting — that is the high cost of small checks.

Part III: Stay Small, Or Grow Funds?

The growth in micro VC funds is now well-documented. While there are many reasons to explain why this trend took hold, the more interesting question to ask is: What will happen to those funds which survive?

Grow the Team

A natural desire of any entrepreneurial endeavor — including starting a fund — is to keep growing it. In the context of small funds, traditional LPs will naturally hope this new crop of managers who emerge will grow a franchise, will add people to the team, and ultimately manage more money. Eventually, some of these franchises can grow to manage quite a bit of money per fund per GP and can, in effect, become a new type of Series A firm. This is the theory. It remains to be seen if more than just a few can make this transition, as the models at seed versus Series A are obviously quite different.

Stay the Course as Lone Wolf

While it may sound traditional to turn a good micro VC fund into a more traditional venture franchise, creating a strong general partnership is not a simple, check-the-box activity. Noting the difficulty, some micro VCs have opted to stay as solo operators longer than LPs had imagined. Some, of course, continue to outperform and earn the right to manage more money per fund (if they choose to). In this instance, the LPs aren’t able to invest more and more of their funds into the GP. In the same way a large VC fund may look for opportunities to increase their ownership in a great company in their portfolio in order to make its own economics work, a large LP will often have a similar desire.

Differentiate and Evolve

Just as investors may have “app fatigue” or “food delivery service” fatigue, LPs pitched by micro VC funds have their own flavor of fatigue. As a way to cut through the noise, many of them drill into what differentiates a GP they’re considering an investment in. This can nudge micro VCs to differentiate on the basis of sector (hardware, Bitcoin, etc.), or geography (focusing in emergent areas outside the Valley especially), or stage (pre-seed vs seed, etc.), and more. And the success of Y Combinator and the potential for more steady budgets for an accelerator or incubator could encourage more to let go of the traditional fund model altogether.

I know these choices because I have been faced with them. The LPs rightly ask these questions and conduct references to determine which way the micro VC wants to go. But the truth is that, just like most at seed don’t know how well a company will do at the very early stages, most of them also don’t know what the optimal path to take is. This can lead to an awkward discussion, where LPs may want or need to hear certain things to “check the box” in their processes versus having the raw discussion about what is working and what doesn’t. The truth is that most people don’t know, and in this market, which is changing year to year, the main value in these smaller funds is that their inherent nimbleness by virtue of being small gives them the right level of flexibility to adapt to a dynamic, ever-changing environment.


My cautionary post-script for any later-stage investor (click here to read it). This applies to traditional VC funds or LPs who like to be on the cap table.

Transforming Uber’s Mobile Experience with APIs, AI, and ML

By now we all know that mobile communications and “chat-style” apps have effectively become the browser within which billions of people (many of whom have never before owned a computer) will access the web. Asian chat apps like WeChat and LINE, among have pioneered innovation in this sector, becoming much more than just an “app,” but transforming into a platform to handle payments, connect with brands, transact with businesses, and much more. The moves we see inside Facebook Messenger angling toward payments, a conversational assistant (Moneypenny), and talking to local businesses are just an inkling of what we can expect in the future. It’s hard to distribute mobile apps, and there’s a power law among the apps we actually use (mostly communications-based), we have the text message entry bar as the new command line interface.

Most people think of “chat apps” when they think of this, and that makes sense. We are using iMessage with our friends, texting on Messenger, and talking to friends overseas with WeChat, etc. It’s easy to imagine each of these services offering conversational assistants, powered either by humans or machines, to help us transact or get things done. Why should we leave Messenger when we’re coordinating with a friend about getting dinner, when the system can just know what we want and respond to our requests implicitly and book a table for us via the OpenTable API?

Now, I think another popular mobile app will also transform into having these characteristics — Uber.

When it started, the Uber app was about calling a black car. Then, it evolved into offering us UberX, and most recently, UberEATS. And, they’re not done, with reports dripping out they’re experimenting with commuters, commerce, group rides, and more, I believe we will see the Uber app transform in ways that will be hard to imagine today. For example, there may be a search box or text box to enter information and/or chat with drivers and friends, and in those conversations, the text box becomes another command line interface ripe for bots to interact with. An example: You call an Uber to meet a friend at a restaurant, you can deep-link out to OpenTable to reserve a table, or maybe just text within Uber you need a table at Restaurant X and it takes care of it in the background. even to the point where your credit card is used for checkout (like inside OpenTable right now).

There are many examples herein. The larger point is that just like our chat apps are transforming into colossal platforms hooked into myriad services, Uber’s mobile app won’t just be a place to order your car or lunch…they will want to capture more of your attention and more of your intent, and now that more AI-based, NLP-based, and ML-based technologies are accessible to third parties, we should expect Uber — like Messenger — to want to hook us into a platform where we can search for, discover, communicate with, and transact with a host of local stores and service providers. These apps will pick up on the natural language we use, they’ll leverage artificial intelligent bots which can parse implicit signals and machine learning algorithms which can learn our preferences over time and either compress transaction time or help us discover new things. For many people who live in cities, Uber is a homescreen app, and it will be fascinating to see how it evolves from EATS to commerce to other areas.

A New Kind Of Drought In Silicon Valley

I have some not so fun news for folks.

It is not on the level of RIP Good Times. There are good times to be had, but only for a portion of the ecosystem’s participants. The news is as follows: Traditional venture capitalists have become significantly more cautious since Labor Day this year. I can’t prove it with data or a fancy graph. And VCs likely won’t confirm it because everyone wants to be in the market. The truth is, they are in the market, but they’re being much, much more selective. The premium companies with real teams and real metrics will get even more intense investment interest, but the rest will look like Lake Wobegon.

I can’t prove why this has happened, but I can take a few guesses: We’ve seen a string of public flameouts of well-funded VC-backed startups hit the press now, even though those carcasses were on the highway this summer; we’ve seen some VC firms quite rationally not bridge some of their portfolio companies to the next round; we’ve seen international economics to be more interconnected than we’d imagined them to be; we’ve seen a number of companies struggle to even get their houses in order to go public; and we’ve seen many investors with a newfound swagger on Twitter, as if the pendulum has swung back a bit after years of being portrayed negatively in the overall narrative of how startups form and grow.

But, most critically, VCs hear from their LPs who have been coaching them now (1) to watch their investment pace; (2) to extend the term of their current fund; (3) to focus on previous funds’ liquidity before asking for fresh capital; and (4) to more aggressively consider partial secondary sales, even if it puts relationships with founders in jeopardy for a bit, as there’s very little M&A to be had for highly-valued startups that need to grow into their valuations. There’s no way out.

It’s the flow of money in and out that is now in question. It’s not about a bubble, per se. LPs largely believe in the asset class and in the long-term arc of technology and computing power transforming industries for decades to come — however, they have their bosses to answer to, as well, and a lot of money has gone out of their wires and not a lot has come back. That engine needs to be lubricated with cash, and with a dry IPO market and very little M&A to write home about, many funds are taking a more cautious approach, examining their own runways, the fuel left in the tank, and are circling the landing strips before being cleared to descend for touchdown.

If I’m right (and hey, I might be wrong!), what this means for founders is that raising subsequent rounds won’t be impossible — it will just be significantly harder. It is not unreasonable to prepare oneself for a prolonged process, to be subject to reams of diligence, to have investors push prices down to cut a deal. This maybe how it should be (in the LPs eyes), but it will be a different look than founders have seen in a few years, and that will make things feel different and likely change behavior overall in the ecosystem. There’s a long way to go until the end of the year, so let’s see if I’m right.

On The Eve Of Apple’s Next Generation iPhones

It’s “New iPhone Eve,” the night before the next generation of Apple’s iPhones hit stores. There’s been so much written about Apple in general and this particular generation of phones, so I just want to highlight three elements that interest me greatly. Previous “S” upgrade cycles have seen the introduction of voice command technology (Siri), biometric sensing (TouchID), and this year, an entirely new intra-app interaction design (3D-Force Touch). I want to focus this short post on the latter. I know there’s tons of news about Apple in general, but I only care about the phone.

But, before that, I need to quickly point out two other things about changes to the iPhone line:

One, Apple sticks it to the carriers!
Everyone hates their carriers. We can’t read their bills. They bilk us for roaming. Going into their stores is a nightmare. It’s sad because they employ good people, but let’s be frank, it’s not optimal, and one of the handcuffs forced upon us is we have to wait for upgrades and are tethered to them for service and their complicated pricing structures. It’s all just confusing and time consuming. Apple is now takes a first step in sticking it to the carriers with their upgrade plans. Apple certainly has its own motives for driving revenue, but they also know consumers will love this move; Apple has a power that can harness consumer sentiment and in this case, they score points and help everyone take an important first step away from locked-in service contracts.

Two, Apple sticks it to the publishers!
Yes, I know that Apple wants everything to happen inside native apps, and that Apple wants to cut off Google’s ad inventory on the mobile web, and that the company just plain hates flash (which drags down pages in the mobile browsers or applications that render web pages inside a native app), and so forth. But let’s face it, crappy content is taking over the open web, it’s being propped up by shitty ads (often coded in flash), and it’s just a pain to read. It got to the point for me where I would just not open a link for fear of how long it would take to load. Now publishers, starved for attention (which then may translate to ad impressions) now have to do the hard work of facing the same music newspapers faced in the last decade. And, no one will feel sorry for them, especially when properties like Buzzfeed anticipated such a world, invested in their own tech and mobile distribution, and imagined news in a social world. As a side note, this will also affect retailers who rely on mobile web touchpoints and who haven’t yet invested the resources to get their audiences onto mobile apps. (For all the publishing whiners out there, the best piece IMO on tactical things to do was written by Dave Winer — read it here.)

And, now back to 3D-Force Touch — Shortcuts for Apps!
For years, I’ve bitched on this blog about how hard mobile app distribution is. Brutal. Given that, I believe companies which emerged around 2007-2012 have better chances at growing their distribution and have essentially built up a moat around competitors. Then, in turn, those companies will benefit to even greater levels as new IoT devices that are tethered to our phones will make it easier to call services, largely because many physical interactions are “easier than opening up a mobile app.” It’s not obvious unless you think about it, but taking out your phone, finding the app in question, and then opening it up and finding the right interaction takes time — new devices like Dash Buttons, voice commands, and other triggers will transform the way we call on services that reside on our phones.

One such transformation could also be 3D Force Touch. Click here for a little video example. Because native apps are silos, when we want to view information that rests in another app while in the current app, we have to entirely switch our context, and go through a clunky maze to get to the new destination. Now we can get back with a back button, but we often lose context. Force Touch will enable users to stay in the current app and see a preview or snapshot of the key information that would’ve, in the old days, only resided in a different app. This could have profound changes for how app makers design and measure activity on their properties.

There are countless examples of why this will be a big change for app makers, the most common being that instead of opening an app to do a simple action, we could just tap on the icon and pick from a drop down menu of simple interactions. When I want an Uber, I won’t have to open Uber’s app, and then hit the button, etc.; with Force Touch, I can just hard touch the icon, and likely pick from a drop down menu to say “call a car” and be done with it.

The main example I like to use involves maps. Google Maps is the best maps product for iOS. Everyone has it. In many texts or emails or from calendar, people often leave those apps in order to visit maps. Google gets paid for those API calls, but they then also have our attention and present us with a valuable search bar where we can create new context at the expense of the previous app we were inside. If we were now stuck in Google Maps, Google could encourage us to search, or could layer information right on top of the map and grab our intent. However, with Force Touch, we could stay inside FB Messenger and continue having our conversation in the chat app. Now, this new feature will not be open to all third-party apps like Google Maps right out the gate, but when it does roll out, it will change how we as consumers think of “opening” and “switching between” mobile apps, and it will alter the metrics measurement and strategies of how mobile developers present information to users in a world where their creations may not be displayed to users in traditional apps, but rather as part of a contextual workflow or conversation, conferring more power to the utilities (like calendar) and communication apps (like SMS) we rely on.

Transcript: @Chamath At StrictlyVC’s Insider Series

@Semil Fireside Chat w/ @Chamath 
StrictlyVC Insider Series 
September 16, 2015
AutoDesk Gallery SF

(This is the transcript from last night’s chat at Connie’s StrictlyVC Insider Series with Chamath from Social+Capital. I wasn’t on Twitter today but checked in the afternoon and saw that tons of people were talking about it. It must have struck a chord, so I talked to Connie and got someone to transcribe the Periscope. It is definitely worth a read. Chamath not only candidly says what most others would be too nervous to say publicly, he does so in a way that demonstrates he is a truly big thinker and pushing forward the model and conception of what a technology investor can and should be.)

@SEMIL Intro: Thanks everyone for coming. Connie organizes these events, they’re something I really look forward to, and in particular this one. A lot of you here mentioned me on email that you were looking forward to this event with Chamath, you probably follow him on Twitter, listen to what he says, maybe you don’t agree with everything, but what I find really unique about Chamath, is that when he says something you know he’s thought about it and you know he means what he says. To be fair to Chamath I emailed him twice before the event and I said, “what do you want to talk, plug, you tell me.. and he says just adlib, make it interesting. So, we’re going to rely on Chamath to make it interesting.

Which Becomes A Trillion-Dollar Company First: Facebook or Uber?

@CHAMATH: Facebook. And it really comes down to a very simple thing, which is, the principle of N of 1 vs. 1 of N. This is something I think about a lot, which is, when you look at a company, they become these foundational layers in society, to me what’s interesting is they always start where they’re a set of many, they’re 1 of N companies, and somewhere along the way what happens is a bunch of them fall off. There’s these periods of real, either misunderstanding, or discontent, or frustration, and then they develop something discontinuous. When you put those things together, that allows a company to separate themselves from the pack, and eventually, everything falls away, and they’re an N of 1 company. Then they scale and are effectively a monopoly.

If you think of companies that multi-generationally have done that well, Microsoft did that, I think Google did that, Apple will become a trillion dollar company, even though they didn’t start off as an N of 1 path, and Facebook has done that.

But when you compare that to Uber, it’s interesting, people want to value the company as if it’s an N of 1, but it’s fundamentally a 1 of N. And I think that doesn’t.. it basically limits the rate at which it can grow, and the violent market effects it can have, and I think what you see is probably business features sprawl in order to generate revenue to justify valuation.

So you know, at Facebook, for five years, all we talked about was user growth. Like there’s only one thing that matters: user growth, user growth, user growth. Why? Because at a certain point, it basically becomes this canonical definitional service in the world, by language which they will not use, but is like, you are the de facto standard, and that’s how you become worth a trillion dollars, because you have market effects, pricing effects, the ability to attract talent, that is just completely unique and differentiated.

But if you’re an N of 1 company, you’re competing with different folks, and that’s the problem with Uber is that it has to compete with a bunch of folks here, both private and public, capitalized and not. In china it has a completely different set of competitors, in India, it has a completely different set of competitors, each of them are funded to billions and billions of dollars, so what happens with market dynamics, is basically driving things to commodification, driving things to basically price discovery where you don’t have pricing power, you don’t have the effects that make you monopolistic, and the problem is markets will not deny you that at massive multiples.

The way that they value things that are fundamentally unique and not easily recreatable.. So, that turn of capital, those 3 or 4 multiples of P/E that makes something a 40 X vs. a 12 X is a difference between grossing $150B and a trillion dollars, and it’s beyond a shadow of a doubt that Facebook will be a trillion dollar company, it’s just you’re talking about the delta: T which is probably sub-15 years. In my opinion. Uber’s not there. Great company. But not anywhere near the path of being an N of 1 company.

Semil: One follow up on that, do you see any similarities from your time at Facebook with Facebook platform and connect, and how Uber may supercharge their platform.

Chamath: Neither of them are platforms. They’re both kind of like these comical endeavors that do you as an Nth priority. I was in charge of Facebook platform. We trumpeted it out like it was some hot shit big deal. And I remember when we raised money from Bill Gates, 3 or 4 months after.. like our funding history was $5M, $83 M, $500M, and then $15B. When that 15B happened around literally a few months after Facebook platform and Gates said something along the lines of, “That’s a crock of shit. This isn’t a platform. A platform is when the economic value of everybody that uses it, exceeds the value of the company that creates it. Then it’s a platform.”

If you apply that simple methodology to any company that says they’re a platform, there are only 3 platforms in the world! You know? Windows is a quasi-platform, decaying, but still, iOS is platform, and Android is platform, but that’s easy because the denominator is 0. So, I think, that these aren’t “platforms”, these are APIs, these are developer tools, which is good, and it’s a bridge to something, but it’s not a platform, so let’s stop calling it a platform, let’s call it what it is, which is a bunch of endpoints.

Discuss The State Of Professional Sports In The Bay Area

Chamath: I think the Warriors are an example of basically applying traditional management to sports, which is like a really unique kind of thing, which hasn’t been done before. Take a step back.. we teach our kids basically, don’t listen to anybody. We just don’t want them to be programmed.. (this is when Chamath’s son, who was sitting in the front row, just left the talk and walked out), so if he he can take an Uber home I guess.

I think the Giants are pretty well run, I think there’s a really interesting opportunity to do something around the Raiders. I’ll leave it at that.

Assessing The Health Of The SF Bay Area Tech Startup Ecosystem

Chamath: These are all really interconnected, but if you think about it, there’s way too much money, in the system, ultimately still chasing few really great companies. The problem with that is that you have a bunch of imposter companies that get funded for a lot longer than traditional cycles.

So if you had 1/10 the capital, the mortality rates would be higher, faster, the curves are sharp, and instead of what happens is the decay is longer, and in the long decay, what essentially happens is that you are feeding capital to companies that should really not exist anymore, and those companies then use that capital to take up space. They use that capital to hire other employees, and all these other people spend a lot more time wasting their time. And that’s problematic, and if you don’t get that churn, then the few that have the ability to really get to escape velocity, are forced to figure out for themselves, how to get that sooner?

So what do they do? They start to pay people more, they start to spend more on these things that think will attract all these people, and that has this negative byproduct, which is everything goes up, the cost of everything starts to rise, and you have this really vicious cycle where at some point then that N + first young engineer, can’t afford to come here in the first place, because he can’t even afford a 1 bedroom out of  5 bedrooms because it’s $2000, and all of a sudden a first year engineer is making $170K, and it’s like this violent vicious cycle that helps nobody.

Semil: So a lot of people think the solution to that is just more housing, more affordable housing, sounds like what you’re saying, even if they do that, it still wouldn’t stop the core problem.

Chamath: I mean you need to do a couple of things. If we’re really going to bet on SF, and if we’re really going to bet on startups. In Silicon Valley, you have to do a bunch of stuff privately and you have to do a bunch of stuff publically.

So at the public level, you have to invest in what the city is doing, and I think you could debate on some level, how much work the city should be doing around transportation, around housing, you have to basically get rid of the nimbyism and you have to decide to build up. You need to quadruple the amount of housing, quintuple amount of housing. You need to tell every young engineer from University of Michigan that they can afford to live here on $80K a year. All the other ancillary surfaces you need to be able to do that, as an example, we look at our startups and we’re like, the minute that they start to spend 15% of their burn, money that we give them, good money, on rent?? Huge red flag goes up. It’s like, there’s all of these other simple signals, when you, on a per headcount basis, are spending so much, and we start to look at like, the productivity of the technical team, and it’s like good but not great and they’re spending the same amount of money as a team in Redwood city, we start to ask ourselves, are you so convinced that success is going to happen in this city at 1.5X of cost.

For every dollar that someone in Redwood City or Mountain View is raising, you have to raise 1.5 times or 2 times that. Just to get to the same point in time. So you’re cutting you half-life in half. To prove what?? That you can take an Uber from some shitty bar to another shitty bar? I don’t understand. These are like the things that I start to think about, these constraints that need to get fixed.

So, at the public level, you need to have an approach that kind of creates the attractive incentives, for people to come and be able to survive on a living wage. Then at a private level we need to hold our companies to a higher standards where they’re not just burning money on useless stuff that is window dressing. That’s fundamentally getting in the way of building something useful.

Semil: When you mentioned the rate of churn, is slower, as that churn slows, what’s the effect of that? Is it clogging up resources? Are people sticking in at roles where companies are going nowhere..

Chamath: I actually think it’s more insidious than that, it’s like telling somebody.. startups are this really delicate compact that an employer has with a bunch of employees, these employees are a highly productive, extremely well intentioned, people who want to do something really productive, they’re willing to make huge sacrifices, in order to do something that changes the world, that to use a slightly overused phrase.

But when you suck them in, and now you don’t pay off that contract, yet they’ve been working 20 hrs/day for months and months, what are you doing to that person’s psyche/ what you’re really doing is you betray that compact that they made with you. Now it’s fine to fail, and in fact it’s great to fail, but if you fail because you didn’t have the courage to move to Oakland, and instead you burn 30% of your cash on Kind bars in the office and exposed brick walls? You’re a fucking moron. Do you know what I’m saying?

On Companies Staying Private Versus Going Public

Chamath: I don’t understand why public is a bad thing. I think it’s the most rationalizing thing in the word. Because you cannot hide behind bravado and nonsense. You are forced to show that you have articulated a strategy, and a gameplan, and a set of metrics, and narrative, and you have to explain that to people who may not necessarily care emotionally. That’s not a bad thing. That is like an act of discipline. So as an example, you look at a company like Amazon, they barely generated a dollar of profit, but Bezos has created a envelop of trust in the public markets, which are extremely fickle, which are extremely judgmental, we claim them to be extremely short-sighted. Yet they’ve taken a 20-year multi-decade bet on this guy.

So I think that line of reasoning is just wad. It’s an excuse that prevents you from being held accountable in ways that make you fundamentally uncomfortable, cause you’re afraid of what it means to build a real business. Build a real business. Be around for decades. You have a compact with employees, financial source of capital, and you have  an opportunity to have market leverage, if you’re good, give you a currency that you can use, so that you can get to N of 1. So why wouldn’t you do it?!

The people that don’t do it, is the people that can’t do it. And the people that can’t do it, will, say all this stuff about waiting, waiting, cause the markets don’t understand.. is just a false trade off, it’s just an immature understanding of your own business. And what it tells me, is that you don’t know your business. Jeff Bezos knows his business. Indisputable. He never grew it 100%. But he grew it 20% per year for 15 straight years. Bang, bang, bang, etc… That guy knows his business.

Trump As A Media Sensation

Chamath: I think he’s, whether you agree with him or not, he is his authentic self. I think that people are starved for average, approachable people, that are themselves. And some of us like it because it’s like watching a train wreck, other people like it because it represents their beliefs and values, it doesn’t matter if there’s authenticity there, and I think the problem is, if you’re part of a system and your entire life has been created by getting these small signals that system matters, you’ll always live by the rules of the system and eventually you become part of the system, you become co-opted, you know you’re not yourself anymore. That’s basically all politicians.

Then every now and then you have this window into the humanity of a person, and it’s really intoxicating. All the people that for once in their life were like, Biden’s the best were simply because of a handful of questions that he answered on Colbert, where he was actually honest and authentic, so I just think authenticity is just the thing that’s truly missing, and I think that’s what people are attracted to.

Audience Q1: Getting Sucked Into A Bigger Money Round Frenzy

Chamath: We were doing some work, and I think the data point that saw was that the largest series A of a very successful public company, if you go back and look at every company that’s ever gone public, and you look at the largest market caps all the way to the smallest, and you look at your series A, and how much they raised, the largest was Google. $25M raise. So this idea that you need all this money is a false trade off. Ben just talked about Fitbit. It’s an amazing example of what a company can do on what people thought was probably, “Oh my god, they must of raised billions of dollars” and it turns out that they didn’t, they were just really good at what they did. So, again, I think that if you looked at a company and how they’re spending money today, we probably would be shocked, relative to historic levels, how much of it’s going into Kind bars and exposed brick and how much is going to the per individual basis, which is great for that person, but again it’s emblematic if that person then takes all that money that they’re making..

Like when I came here, my first job, I made $55K. In 2000. I was a product manager. How do you go from $55K to $175K in fifteen years? So it’s great, but if I were taking that $175K and still having less than that $55K of net effective income, because 2/3 of that goes to rent, and another 1/3 goes to transportation, am I really that better off? I have a higher W2, but I don’t feel richer.

So who’s making the money? Cushman & Wakefield, who owns this building makes the money? That makes no sense to me. So the way we react to this is, we’re like, we try to see who’s willing to do the hard work of business building, and who’s acting. And there are very simple ways. We just ask, let me see how you’re spending your cash. The actors just jump off the page. The company builders are just cheap, they’re just grimy, and just, shitty office space, and they’ve got to keep it under 8 or 9% of their total burn, and they find people who really really believe in the thing they’re making, and they decide to just live in Oakland and pay for Lyft, and it’s still cheaper.. They do all kinds of creative things that deserve capital so they can build. So it forces us to ask those questions, “How are you really company building?” And that’s how we get the truth on who’s going to stand the test of time.

Audience Q2: Cite Examples Of Public And Private Initiatives The Region Needs

Chamath: I can answer this question in the context of Social Capital. So we made a really big transition in the last month, where we decided we’re going to build an organization that looks different than a venture firm. That organization is going to be this hybrid, bastard-stepchild of Berkshire Hathaway and Blackstone and Blackrock.

What I mean by this is, we want to have a large permanent capital base and we want to basically take really long discontinuous bets on companies and sectors and trends. One of the things we said we needed to do as part of that is we need to start really thinking through, having almost like a real estate fund. The reason we said that to ourselves was we owe it to our companies to alleviate some of these problems where nobody else is going to.. If we went and built one million square feet somewhere of mixed-use work and live, and we completely conceptualized what it means to have a modular living environment for a millennial cohort of like, folks who want to work at companies who don’t necessarily have kids, etc. We can do that in a way, and give that back to our CEOs, as a benefit of working with us.

You can probably make all the economics work, because frankly we only really care about the employee of the company anyways, and the equity in the long-term appreciation of real estate will take care of itself, if you take the 30-year view. So, we’re at that point now where we’re like, “Wow! We should probably just go raise a couple billion dollars and actually go get into the real estate business and solve this problem systematically for our companies.”

Maybe in that, it becomes a blueprint for how others should do it. So that’s an example of a private solution to what would otherwise be a public solution that’s probably not going to happen. So, we’re just basically going to act as our own little city-state, and decide how to do it ourselves. In order to do that, companies will have to have the courage to be in San Mateo or San Carlos, and oh, by the way, every major $100M company has never been created north of Palo Alto, in case you’re curious.

Quick Thoughts On Today’s Seed Environment

Chamath: I think it’s really amazing that there’s so many people that.. I feel I have the same version of what all these other people feel, which is we all feel somewhere along the way we were a bit of an accidental tourist, we got lucky, there’s degrees of how lucky we all got, but we’re all then willing to pay it forward, and I see a lot of people, e.g. there’s a bunch of Facebook groups of ex-Facebook employees and the number of these people who are writing these really big checks into companies, and it’s not the amount of money that matters, it’s just that they’re willing to pay it forward.

So, whether they’re doing it with the profit motive or not, I think seed stage right now is very healthy. It’s robust. I think the institutionalized efforts around it, people are a little frustrated because they used to have so much proprietary deal flow and now all of a sudden, you can raise $2 million dollars from 10-15 folks who worked at WhatsApp or Facebook, or whatever.

I think that’s fantastic. I hope there’s more of it. Frankly, as some number of us continue to feel out and be in this ecosystem, and be fortunate enough, you have a responsibility to plow back. Somewhere along the way, it’s our responsibilities as institutions, to actually do a better job at enforcing discipline so that these guys can actually get a chance to get to this stage, and I think that that’s probably another thing where we’re not doing a great job. There’s a lot of sheepish, “follow me” mentality.

Series A & B Investors Need To Enforce Discipline

Chamath: The problem right now, is that venture is completely undifferentiated. Everybody’s the same. Everybody’s the same. Everybody has a set of services that every other person has. So, when everybody’s theoretically different but the same, nobody has a backbone. There’s fundamentally no authenticity in the marketplace. So as a result, nobody will ask these kinds of questions. Nobody will be disciplined. In a company that’s not working, what they’re not thinking to themselves, is “Wow, maybe if we actually return $2M back, and actually capitalize these three other people with a different idea, or fund that young woman who I kicked out the door because I didn’t understand what she was saying.”

So the discipline is important. Why? Because we have a responsibility to get the best ideas to market. We have the responsibility where we should be taking good capital risk. If at the end of this cycle, whenever this ends, we look at who made all the money, and it’s not Benchmark or Sequoia, or Social Capital or Andreesen, but it’s Pushman & Wakefield, WeWork, and ZeroCater, something’s wrong! Honestly guys, something’s wrong.

So, that’s what I think about.. we have to start.. you don’t have to prognosticate doom and gloom and RIP good times, you don’t need to do that, but you do need to go in and say, let’s just dissect how we’re spending money, and none of this idiotic window-dressing nonsense. And see how they react, because if the people don’t have the courage to make hard decisions, you’re probably wasting your money.

Now, not only are you doing a disservice to yourself and your and your own case, you’re really doing a disservice to all the employees who believe that CEO has the courage and the balls to make it happen, when really what they’re fucking doing is acting. They’re really just a walking failure just waiting for the last shoe to drop. And that’s a disservice to them. So you confront that person, give them a chance to change, and if they can’t change, then you better do something. That’s the hard work of building great companies. Not enough people are willing to do that.

The Story Behind My Investment In Datos IO

I am not an enterprise IT person, but I have made a few investments in the space and will definitely do more. As a small investor, the formation of these types of companies is quite different than what the broader startup/tech population is exposed to for SaaS and consumer-facing businesses. Often in enterprise IT and infrastructure startups, there are real barriers to starting up — the founders need to be of a certain caliber, there likely needs to be some tech breakthrough or promise of one. the dollar requirements out of the gate are much steeper, and the question of sales (distribution) can make or break the deal.

As a result, these investments form with very different characteristics. It is not uncommon for an elite team of new founders to raise $5m+ just on a slide deck, pre-product. The likelihood of returns generally in this space are much higher than consumer, but the breakouts aren’t as common or high-flying, though we are on the verge of seeing a company like Nutanix go public soon and hit valuation numbers that very few companies see.

As I started Fund II about 18 months ago, I was introduced to the founders of Datos IO by one of my LPs. In fact, this LP has sent me tons of deal flow that I wouldn’t have ever seen. That’s only half of what’s cool about this; of course, I am not qualified to evaluate these businesses on a technical level, so how do I go about getting conviction to invest in companies like

One of my biggest lessons — one of many, so far — is that everyone assumes “investor diligence” is done (if at all) in a somewhat similar manner. In reality, investors perform diligence and arrive at their own point of conviction through a variety of methods. Some make market maps; some call all references and customers; some hire technical savants to help them birddog the technology’s worth; some just wing it. In this case, I conducted “network diligence” by talking to three of my close friends who are all deeply thoughtful about enterprise IT and infrastructure, and I walked through this opportunity with them.

After testing my network and spending lots of time with the two founders, I was able to gain conviction in the caliber of the team and technology. And, so far, that process worked just fine as Datos IO went on to earn many term sheets from some of the world’s best technology investors, ultimately selecting Lightspeed as its Series A lead, a firm with a string of hits in infrastructure. A better understanding of the company’s offerings verifies what Datos’ investors already know: That the company, which solves recovery issues for distributed databases, is graduating pilot customers to real customers quickly, by providing a consistent view of the data across their infrastructure for recovery needs.

This example provides another reason why I feel investing is such a great fit for me personally. Being a small investor and with a network to help around the edge, I can learn much more about the enterprise IT sector in a shorter period of time. Though my knowledge in this domain will never be on par with those who focus in this area, for now I enjoy having the flexibility to explore new sectors and make investments broadly. In part, it helps me write pieces like this called “The Enterprise, In Lay Terms,” which has turned into one of the most-visited posts on my site. For 30 years, scale-up relational databases ruled the client-server world, where companies like Veritas provided data management tools. Today, distributed applications (IoT, Mobile, Social, Cloud) call for a new data-centric world where five of Top 10 databases are open-source. The stellar team of researchers and operators at Datos IO have not only built and developed this new technology and architecture, but they’ve put in the hands of large corporations who are lining up to harness their technologies. That is no small feat, and I am proud to be a very, very small part of the team’s journey.

Missing This Week’s On-Demand Conference In NYC

Tomorrow is the second installment of The On Demand Conference, this one taking place in Manhattan. My co-conspirators Pascal from Checkr, Misha from Tradecraft, and the entire Tradecraft team have put together an incredible agenda, event, speaker lineup, and topic list. Sadly, I am not able to make this trip, but I can’t wait to hear about it from friends and colleagues who will be attending. If you haven’t already, check out the Line Up and all the great Agenda Topics that will be discussed.

The on-demand startup world has gone through some downs since the last conference. I’ve written about those here. In my conversations with Pascal and other investors about this, there’s no doubt that the bar goes higher and higher now for companies to earn venture investment. While the consumer demand for these services still remains, how that demand is fulfilled is now under question — and that’s a good thing.

In particular for New York City, with its own great startup scene, this is a good venue for this discussion given the competition and density. It will be interesting to see if one coast has figured out tricks the other coast can learn from, and vice versa. On a personal note, I will be sad to miss tonight’s smaller drinks event for the speakers and moderators, will miss hanging out with Shai, Steve, Matt, the Button folks, and many other friends I’d love to have seen, and I was really looking forward to opening tomorrow’s session in a fireside chat with Albert from USV, but Misha is stepping in and is also interested in many of the same issues touching the on-demand space. (In particular, make sure to read Albert’s post today about the connection between on-demand services, automation, and guaranteed basic income.)

Wishing everyone the best of luck with tonight and tomorrow’s big show, and a huge thanks to Pascal, Misha,  for their support. They make this stuff happen with the greatest care and attention to detail.

Haywire is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2015 Semil Shah.

“I write this not for the many, but for you; each of us is enough of an audience for the other.”— Epicurus