Posts from entrepreneurship

Gold, Silver, and Bronze

Winning a medal at the Olympics is a big deal for athletes all around the world. Obviously a gold medal is better but silver and bronze are pretty awesome too.

In startup land, it works out pretty similarly. In each and every big “winner takes most” market there is one big winner (the gold medal winner) and a few other big companies (silver and bronze) and then not much more.

If you look at web search, Google won the gold medal and has a $550bn market cap to show for it.

In social, Facebook won the gold medal and has a $360bn market cap to show for it.

In ridesharing, Uber won the gold medal and has a purportedly $60bn market cap to show for it.

You can do well with silver and bronze. Twitter is worth $13bn. Lyft is supposedly worth $5.5bn. But coming in second or third in a big market is generally an order of magnitude (or two) less valuable in the long run.

And you had better get on the stand and get a medal if you are working in a big “winner take most” market because fourth or fifth or sixth is rarely worth much, if anything.

These are high stakes markets where winning is everything and losing is nothing. And things play out pretty quickly. Within five years, we generally know who won, who placed, who showed, and who whiffed.

It is possible that with the emergence of decentralized networks these dynamics will change and we will be on to a very different market dynamic. But for now this is how it goes. Go big or go home.

Reboot Podcast With Jerry and Brad

Jerry Colonna, Brad Feld, and I go way back in the venture capital business. We met in the mid 90s and worked very closely together during the late 90s. I still work closely with Jerry and Brad but not quite as intensively as we did back then.

We got together a couple weeks ago (virtually) and chatted for an hour about the personal struggles we all dealt with and overcame as we grew up in the business.

It’s a pretty revealing discussion. I just listened to it and cringed a few times. Jerry has this uncanny ability to get people to say things they don’t often say. He did that well on this one.

There is a lead in of about five minutes. The conversation starts after that.

Dear Fred

I get so many emails from people who are thinking of starting a company and they share their idea with me and ask me if they should do it. They want my feedback on their idea. These are, for the most part, people I have never met and have no context for. I came across five of them this morning in my inbox. It reminded me of this tweetstorm from last year.

tweetstorm

I understand the need for validation. And part of me wants to tell them “go for it.” I would like to see more people get up the nerve to chase their dreams. But I don’t want to be complicit in that. So most of the time, I just delete the email and move on. Sad, but true.

The State Of The NYC Tech Ecosystem

Matt Turck has penned a “State Of The City” post about where the NYC tech ecosystem is right now. I get asked this question all the time and I haven’t been doing a great job of answering it. I will use some of Matt’s work the next time that happens.

Here’s some of my favorite points from Matt’s post. If you live and work in the NYC tech ecosystem, or care about it, you should go read the whole thing.

NYC as a leading AI Center:

The New York data and AI community, in particular, keeps getting stronger.  Facebook’s AI department is anchored in New York by Yann LeCun, one of the fathers of deep learning.  IBM Watson’s global headquarter is in NYC. When Slack decided to ramp up its effort in data, it hired NYC-based Noah Weiss, former VP of Product at Foursquare, to head its Search Learning and Intelligence Group.   NYU has a strong Center for Data Science (also started by LeCun).  Ron Brachman, the new director of the Technion-Cornell Insititute, is an internationally recognized authority on artificial intelligence.  Columbia has a Data Science Institute. NYC has many data startups, prominent data scientists and great communities (such as our very own Data Driven NYC!).

 

NYC as a home to “deep tech”:

Finally, one trend I’m personally particularly excited about: the emergence of deep tech startups in New York.   By “deep tech”, I mean startups focusing on solving hard technical problems, either in infrastructure or applications – the type of companies where virtually every early employee is an engineer (or a data scientist).

For a long time, MongoDB was pretty much the lone deep tech startup in NYC.  There are many more now.  A few of those are in my portfolio at FirstMark:  ActionIQ, Cockroach Labs, HyperScience and x.ai.   But there’s a lot of others, big and small, including for example: 1010Data (Advance), BetterCloud, Clarifai, Datadog, Dataminr, Dextro, Digital Ocean, Enigma, Geometric Intelligence, Jethro, Placemeter, Security ScoreCard, SiSense, Syncsort or YHat – and a few others.

 

The Diversification and Broadening of NYC’s Tech Ecosystem:

One way of thinking about New York’s tech history is one of gradual layers, perhaps something like this:

  • 1995-2001: NYC 1.0, lots of ad tech (Doubleclick) and media (TheStreet)
  • 2001-2004: Nuclear winter
  • 2004-2011: NYC 2.0, a new layer emerges around commerce (Etsy, Gilt) and social (Delicious, Tumblr, Foursquare), on top of adtech (Admeld) and media
  • 2012-present: NYC 3.0 – in addition to the above, just about every type of technology covering just about every industry

Certainly, the areas that put NYC on the map in the first place continue to be strong.  New York is the epicenter of the redefinition of media (Buzzfeed, Vice, Business Insider, Mic, Mashable, Bustle, etc.), and also home to many great companies in adtech (AppNexus, Tapad, Mediamath, Moat, YieldMo, etc.), marketing (Outbrain, Taboola, etc) and commerce (BarkBox, Birchbox, Harry’s, Warby Parker, etc.).

But New York has seen explosive entrepreneurial activity across a much broader cross-section of verticals and horizontals, including for example:

  • Fintech: Betterment, IEX, Fundera, Bond, Orchard, Bread
  • Health: Oscar, Flatiron Health, ZocDoc, Hometeam, Recombine, CellMatix, BioDigital, ZipDrug
  • Education: General Assembly, Schoology, Knewton, Skillshare, Flatiron School, Codecademy
  • Real estate: WeWork, HighTower, Compass, Common, Reonomy
  • Enterprise SaaS: InVision, NewsCred, Sprinklr, Namely, JustWorks, Greenhouse, Mark43
  • Commerce infrastructure: Bluecore, Custora, Welcome Commerce
  • Marketplaces: Kickstarter, Vroom, 1stdibs
  • On Demand: Handy, Via, Managed by Q, Hello Alfred
  • Food: Blue Apron, Plated
  • IoT/Hardware: littleBits, Canary, Peloton, Shapeways, SOLS, Estimote, Dash, GoTenna, Raden, Ringly, Augury, Drone Racing League
  • AR/VR/3D: Sketchfab, Floored

 

 

I like the NYC 3.0 moniker. It’s a very different place to start and invest in tech companies than it was even five years ago. Bigger, deeper, broader, and scaling nicely. Just like the companies themselves.

Mission Driven Founders

I’ve written many times about how I/we prefer to invest in mission driven founders vs mercenary founders. The former starts a company because they see a problem they feel compelled to fix. The latter starts a company because they see an opportunity to make money. There is nothing wrong with the latter. It is likely the reason that the vast majority of companies are started. But we prefer to invest in the former because there is an extra something going for a founder who starts with a mission. It leads to more tenacity, more passion, more feel for the product and market, and ultimately a higher probability of success.

For role models for the mission driven founder we need to look no farther than the founding fathers and the opening line of the Declaration of Independence, published 240 years ago today:

When in the Course of human events, it becomes necessary

The key word being necessary. These people had had enough and NEEDED to forge a new path.

So when thinking about starting a company, ask yourself if it is necessary. That will tell you a lot.

The Summer Doldrums

We are entering the summer months when things move slower in the investor community. This is true of venture capital, but it is also true of other investment sectors as well. Summer vacations slow things down and investors also use the time to step back a bit and evaluate how the first half of the year has gone and plan for the second half.

I know many companies don’t like to raise capital in the summer months. While I understand that approach and it is conventional wisdom, I think the contrarian approach of raising in the summer can also work.

Raising money in the summer months will go slower and can be frustrating as you lose weeks at a time to vacations. Partner meetings are harder to get scheduled. And trying to get multiple potential investors on the same time frame is nearly impossible.

But the benefit of raising in the summer is that you are not competing with as many other companies to get the investor’s attention. You can more easily rise above the noise in the summer. Investors don’t take the summer off, they just slow things down a bit. So if you need to raise capital in the summer or just want to, you can make it work. You just need to allow more time for the process and be patient and flexible.

One advantage of raising in the summer is that you can take care of fueling the tank when things are slow with customers and be ready to step on the gas in the fall when things pick up again. The last four months of the year are often a sprint to the finish line and using up some of that energy raising is often suboptimal.

So if you find yourself in the market for capital this summer, don’t fret. But be prepared for a slog that doesn’t move as fast as you’d like it to. It’s the doldrums after all.

Second and Third Tier Markets And Beyond

I am in Nashville for a couple days with The Gotham Gal who is giving a keynote at a startup conference today. I mostly came along for a chance to spend a couple days in Nashville. But I will also be at the conference later today to see her do her thing.

Last night we attended a cocktail party with investors from the southeast and then had dinner with an entrepreneur in Atlanta that The Gotham Gal backed a few years ago. At both we talked about entrepreneurship in the southeast and the funding environment for companies in this part of the world.

The way I think about the startup sector in the US is that the first tier is Silicon Valley. More than half of all startup activity and startup funding activity happens in the Bay Area which now includes SF and the east bay. You could simply focus on Silicon Valley and ignore every other part of the US and the world and do just fine as an investor. Many do.

The second tier is NYC and LA and Boston. Between these three cities, another third of startups and investment capital reside. All three of these startup cities are vital and growing rapidly. You could simply focus on NYC, LA, and Boston and ignore the bay area and other parts of the US and the world and do just fine as an investor. I am not aware of any firm that has that strategy as it doesn’t really make sense. But it could easily be done.

The third tier includes Seattle, Chicago, Atlanta, DC, and a few other smaller places like Boulder and Austin. I am doing this entire post from my head and not referring to any survey. There are a bunch of these surveys and I’ve read them all so I am sure this is directionally correct but I am also sure that I am missing a place or two.

This third tier is a decent place to be an entrepreneur and an investor. But there are challenges. Entrepreneurs in the third tier can access the talent and capital they need to be successful in these third tier markets but it is a bit harder to do both. Investors can be focused on these markets if they keep their fund sizes small enough or they can take a hybrid approach by being focused on these markets and also investing in the first and second tier markets. The latter is how we have always approached being a NYC centric investor.

But there is a dynamic that goes on in these third tier markets where the local investors look to investors in the first and second tier markets to come down and “validate” their investments. And the investors in the first and second tier markets won’t come down and do that without a strong local lead. This game of “chicken” happens ways too often in these markets and is incredibly frustrating to entrepreneurs in these markets. These third tier markets need a few strong Series A focused VC firms who have large enough fund sizes to be aggressive lead investors and also have the conviction and stomach to play that game. That is what USV, and Flatiron before it, did in NYC. That is what Foundry did in Boulder. That is the game Upfront is playing in LA. Every third tier market needs a few VC firms like that. And being that investor is a terrific way to make a lot of money.

Beyond the third tier lies a lot of even smaller markets. I am in one today in Nashville. It has a huge health care sector that produces a lot of entrepreneurial and executive talent. It has a decent amount of local seed capital. But it is not a major VC destination. The southeast VCs will come here regularly looking for opportunities. But it suffers even more from the issues I talked about in the third tier. The same is true of places like Pittsburgh, Des Moines, and Kansas City. I mention those three cities because USV has investments in companies in all three places.

The truth is you can build a startup in almost any city in the US today. But it is harder. Harder to build the team. Harder to get customers. Harder to get attention. And harder to raise capital. Which is a huge opportunity for VCs who are willing to get on planes or cars and get to these places.

There is a supremacism that exists in the first and second tiers of the startup world. I find it annoying and always have. So waking up in a place like Nashville feels really good to me. It is a reminder that entrepreneurs exist everywhere and that is a wonderful thing.

Filling Out A Round: When It Matters, and When It Doesn’t

Almost every financing I’ve been involved with over the years (seed, VC, growth, raising a VC fund) goes mostly like this:

  • Struggle like hell to find a lead
  • Come to terms with the lead
  • Turn your attention to filling out the round
  • The deal gets oversubscribed as all the investors that could not summon up the courage or did not have the checkbook to lead the deal scramble to get into what is now a “hot deal”
  • You end up saying no to a lot of people you wish you could say yes to

So how do you decide who to let into the round and who to say no to?

Well the truth is that it sometimes matters a lot and sometimes doesn’t matter at all.

There are two primary factors that I like to focus on when choosing who to let in and who to say no to:

  • Do they have deep pockets and have they shown a history and a propensity to follow on in future rounds. Yes means try to let them in. No means prioritize others over them at the margin.
  • Can they add value and/or will they cause harm in any way. Adding value is a plus. Doing harm is a negative (obviously). Harm should be avoided at all costs. Adding value is a nice to have but not a must have. And investors always claim to be able to add value and very few actually do. If someone has already added value without even being in the deal, that’s a strong signal that carries a lot of weight with me.

There is one other factor that is worth considering. If someone is a friend, a former colleague, a person you know, trust, like and would like to have along for the ride, that is as good of a reason as any to let them in. But just remember that having friends in a deal that goes bad is a good way to lose friends. So make sure these are friends who have lost money, can take the hit, and aren’t going to hold it against you.

So here is when it matters and when it doesn’t.

  • Seed investors aren’t likely to follow round after round and while some can add value, many don’t. I would not sweat the allocations/syndication decisions that much in a seed deal other than avoid troublemakers at all costs. Otherwise, get the money and move on.
  • VC rounds (Srs A, Srs B, Srs C) are generally where the syndicates matter the most. Find a strong lead who will take a board seat, manage the syndicate, and help you. Then if there is money left over find VCs who have deep pockets, who have demonstrated a bias to follow on in round after round, and are willing to follow your lead.
  • Growth rounds are generally where everyone wants to pile in and there aren’t a lot of board seats or governance issues to deal with. You may find investors that can help in these rounds but they are mostly about getting the money at a good price and getting back to business.

I have seen entrepreneurs try to optimize these decisions and spend a lot of time on them. Investors scrambling to get into the deal will fill your head with all sorts of promises, arguments, and the like. Which makes it even more tempting to spend time on the decision and make the best one.

My advice is to make good decisions and not try to make the very best ones. Focus on deep pockets who are known to follow on and be supportive and avoid troublemakers. Everything else is a nice to have but not a need to have.

Experiment and Scandal

We are living in a time of great experiments. They are not happening in the lab. They are happening in the real world. And they are being financed by real people. We are witnessing the de-institutionalization of experimentation. We are returning to a time when anyone can be an inventor and innovator. Some of this has happened because of the explosion of venture capital, both in the US and also around the world. Some of this has happened because entertainment and culture has embraced the world of experimentation and innovation (Shark Tank, Silicon Valley). Some of this has happened because the tools for innovation and experimentation have become mainstream and anyone can use them.

I am not thinking of one thing. I am thinking of many things. I am thinking of The DAO. I am thinking of Bitcoin and Ethereum. I am thinking of Oculus getting financed on Kickstarter. I am thinking of the launch of equity crowdfunding for everyone in the US last week. I am even thinking of things like Theranos.

All of these things are great experiments that will produce great benefit to society if they succeed. But by their nature experiments often fail. They need to fail. Or they would not be experiments.

And one of the challenges with the de-institutionalization of experimentation is that some of these failures will be spectacular. Combine that with the idea that these experiments are being funded by real people and the idea that the world of media/entertainment/culture has injected itself right in the middle of this brave new world and you have the recipe for scandal. And scandal will naturally result in efforts to put the genie back in the bottle (Sarbanes Oxley, Dodd Frank). And these regulatory efforts will naturally attempt to re-institutionalize experimentation.

I find myself wishing we could keep the dollars invested and hype down when we do these massively public experiments. But the dollar/hype cycle is a natural part of being human. Some dollars are invested. We get excited about this investment. We talk it up. More people find out about it and more dollars are invested. More of us get excited about this investment and we talk it up more. Rinse, repeat, rinse, repeat and you get unicorns and distributed autonomous funding mechanisms entrusted with hundreds of millions before anything has even been funded. Eventually some of that gets unwound and the tape is full of red.

Don’t get me wrong. I am all for distributed autonomous organizations and the innovation behind them and in front of them. There isn’t much out there that I am more excited about. But I am also very fearful that this could end badly. And even more fearful of what may be foisted on us by well meaning regulators when that happens.

So let’s celebrate this incredible phase of permissionless innovation we are in. And let’s all understand that we will have many failures. Some of them spectacular. Money will be lost. Possibly hundreds of millions or billions. Let’s expect that. Let’s build that into our mental models. So when that happens, we can suck it up, deal with it, and keep moving forward. Because an open permissionless world of innovation that everyone can participate in is utopia in so many ways. The good that will come of it will massively outweigh any bad. But bad there will be. I can assure you of that.

When You Have Concerns

I hear this said all the time – “when you have concerns about an employee, it almost always means you will need to make a change.” I hear execs lament that they tend to wait too long to admit that they made a hiring mistake and act on it. I hear them wish they trusted their gut more. And it is not always a hiring mistake. It is often a case of someone doing great in a role or an organization at at time and then failing as the org or the culture changes around them. In this latter scenario, loyalty and appreciation for contributions made loom large.

And yet that conflicts with the idea that you can grow and develop talent and you can coach people to evolve and change.

A friend of mine told me yesterday that “you have to pay attention to the key moments” when you are evaluating an employee that you have questions about. She suggested that concerns always exist and it is not true that when you have concerns, it almost always leads to making a change. And she said that culture matters a lot and can’t be sacrificed when making these calls.

I don’t do a lot of hiring and firing personally, only at the highest levels. But I do observe executives in our portfolio companies struggling with these decisions and have gone back and forth on how to advise them in these situations. I tend to like action, decisiveness, and a willingness to make a mistake over inaction, pondering, and a desire to get everything right. And so I generally coach executives to make a call and move on when they have concerns.

But the conversation with my friend yesterday gave me pause. I wonder if my advice to make a call and move on is always the right advice. I am curious how the AVC community thinks about these things. Because these are the things that matter most of all in building, managing, and leading a business.