Posts from entrepreneurship

Face To Face

As we all prepare for the fall back to school/back to work season, I thought I’d touch on a topic that has been top of mind for me for the last six months.

The covid pandemic taught many of us that we can be productive and our companies can succeed in a fully remote work environment. But just because you can does not mean you should.

In the venture capital business, this has meant making investments in teams we don’t meet face to face. For founders, this has meant raising rounds from their offices instead of getting on planes.

As the pandemic has eased and offices have gradually reopened over the last year, we are meeting more founders face to face. But we have not gone back to a world where we meet every team we back in person. I don’t think we will ever go fully back to that world.

But even if the way we work has changed permanently, it does not mean that it has changed for the better. I believe that all change has positive and negative impacts. We can meet more founders than we used to. And founders can meet more investors. That is good. But matches are now being made over video and that is not always great.

We know that humans are better to each other in person. We know that in-person interaction is more meaningful, we are more present, and we connect in more fundamental ways.

So I believe that we must work in the coming years to get out of our offices (or homes) and see each other in person more often.

That means we should run fundraising processes that include meeting in person. We can do the initial screens (on both sides) over zoom, but the final selection process should include face-to-face meetings whenever possible. And board meetings should be done in person at least a few times a year. And those in-person meetings should include some social time in addition to business.

For companies, this means hiring should include a face-to-face meeting. Teams should meet in person regularly. Going to the office should be a regular occurrence for those that live near one.

It is time to get back to the office, at least some of the time. It will make for better business. And I also think it will make us happier at work.

#entrepreneurship#management#VC & Technology

Bridge Loans

When fundraising gets tougher for startups, the existing investors (insiders) will often provide a bridge loan to the company to extend the runway for getting another round done. There is more of this sort of thing happening in today’s fundraising market and I thought I’d share some of the things I have learned about setting up bridge loans.

First, bridge loans are a bridge to something else. Most commonly they are a bridge to a round of financing with new investors (outsiders). They can also be a bridge to the sale of the company. Occasionally, but not often, they can be a bridge to getting cash flow positive. If none of those things is going to happen in a relatively short period of time, then it is a bridge to nowhere and you really want to avoid that. A bridge to another bridge is never a good thing and should be avoided at all costs.

An alternative to a bridge is an “insider round” where the existing investors provide sufficient capital to fund the business for eighteen to twenty-four months. That is a real round of financing and it is not a bridge. While that can sometimes be the right answer for a startup, I strongly prefer bringing new investors/new capital into a company in every financing round. New investors strengthen the investor syndicate which makes the company more resilient. New investors bring new ideas, new experiences, and new sources of funding to the business. New investors in every round are a very good thing and I like to try for that whenever possible.

So let’s say your company really wants to bring new investors into the business with another round, but it is taking longer. But you and your investors are confident that the new round will happen. Then a bridge is a good idea.

Here is how I like to structure a bridge:

  • All material existing investors should participate, ideally “pro-rata”, meaning the investors participate based on their respective ownership interests. When you have an existing investor that owns a large percentage of the business and they won’t or can’t participate, you have a problem. You can get a bridge done in these circumstances but it will be painful because nobody likes to “carry” a large existing investor who can’t support the business.
  • The ideal structure is a convertible note, with nominal interest, and a discount upon conversion into the next round of financing.
  • I like the discounts to be based on the amount of time the bridge note is outstanding. This creates an incentive to get the round done quickly, which is what everyone wants in this situation. It is also easier to explain the discount to the new investors in the next round when the discount is small if the bridge has not been outstanding for long. And it is understandable if the discount is larger when the bridge has been outstanding for a longer time period.
  • I like to start with a 5% discount and cap the discount at 25%. The ideal discount is between 10% and 20% and so the time frame for the various discounts should be set with that in mind.
  • A very important consideration in structuring a bridge loan is what happens if the company is sold when the note is outstanding. If the bridge documents do not specify anything in this situation, the noteholders will only get their money back, plus interest, in a sale. That is not really appropriate given that they are providing the capital to get the company to a sale, and so I like a premium to be paid in the event of a sale. I like somewhere between 2x and 3x depending on the circumstances.

When it is time for a bridge, the lead investor, which is typically the investor with the largest capital invested and largest ownership, should “step up”, suggest terms, and work with the investor syndicate to come together and provide a bridge loan. That kind of leadership is very important when fundraising gets harder. The startups that have strong leads will do a lot better in tough times and this is a really good example of why that is.

#entrepreneurship#VC & Technology

How This Ends

Back in February of last year, I wrote a blog post with the same title and said this about the asset price bubble we were living in and investing in over the last few years:

The big question is how does this end?

I believe it ends when the Covid 19 pandemic is over and the global economy recovers. Those two things won’t necessarily happen at the same time. There is a wide range of recovery scenarios and nobody really knows how long it will take the global economy to recover from the pandemic.

But at some point, economies will recover, central banks will tighten the money supply, and interest rates will rise. We may see price inflation of consumer goods and labor too, although that is less clear.

When economies recover and interest rates rise, the air will come out of the asset price bubbles that have built up and the go go markets will hit the brakes.

Well now the markets have hit the brakes and the new question is how that ends.

I have been using the early 80s as a bit of a mental model. The late 70s saw oil prices rise and stagflation emerge and while that is not exactly what has happened with COVID and the war in Ukraine, there are some similarities.

In the early 80s, the G7 economies tightened the money supply, raising interest rates dramatically, in an effort to bring inflation under control. You can see the effect in this image:

The early 80s had a double dip recession (one in 1980 and another one for 18 months in 1981 and 1982). The economy was weak for three years at the start of the decade. But the latter half of the decade was one of the best economies in modern times.

So I suspect we are either in a recession right now or headed to one, brought on by tightening money supply/higher rates that are being used to control inflation. That recession could easily last until the end of 2023. But we don’t really know how long it will take for this cycle to play out.

Markets have already corrected and I think that public tech stocks have already seen most of the damage they are going to see. I don’t know if we have hit bottom but I think we are closer to the bottom than the top now. But that does not mean they will turn around and go right back up.

This is a price chart of the NASDAQ during the early 80s recession and you can see that prices did not start to move up until the second half of 1983, when the recession was starting to end.

So how does this market meltdown that we are now in end?

First, we need to see the economy slow down and inflation slow down. We need to see stocks bottom out and hang out there for a while. And we need to be patient. None of this is going to happen fast.

I would be planning to ride this thing out for at least eighteen months or more.

#Current Affairs#economics#entrepreneurship#stocks#VC & Technology

The Founder Resolve

Investing in founder-led businesses is comforting to me. They have the ability to see the forest through the trees and do what is necessary to evolve the business.

Two great examples of this are Microsoft in the mid 90s and Facebook a decade ago.

Microsoft had spent more than a decade competing and winning the desktop software market and then Netscape came along and presented an entirely new market opportunity that had both major upside and major downside for Microsoft. Microsoft reacted by moving aggressively to compete with Netscape by launching Internet Explorer and using its desktop software dominance to establish IE as the dominant browser by the end of the decade.

Facebook had spent about a decade competing and winning the social networking market and then Apple launched the iPhone and new mobile social networks like Instagram emerged that both threatened Facebook’s existing dominance and also presented new large opportunities in social networking. Facebook went on a year-long effort to become a “mobile-first” company and also acquired Instagram that year. This all happened in Facebook’s first year as a public company.

I was thinking about that because as many are wringing their hands about the collapse of crypto prices and stock prices and cutting back costs and playing defense, Coinbase announced yesterday that they are investing heavily in the next wave of web3:

The application era of crypto is upon us and products/companies like Metamask and OpenSea are showing how important and lucrative that market is. Coinbase has reacted by making huge new bets on Coinbase Wallet and Coinbase NFT and is committed to winning in those markets like it did in the investment era of web3.

It is very hard to do this sort of thing when your stock price is under pressure and when the markets are in free fall. And yet that is what leaders must do when new use cases emerge and present themselves as both an opportunity and a threat.

Disclosure: I am a Director of and our family is a large shareholder of Coinbase.

#entrepreneurship#Web3

Competing To Win Deals

So I saw this tweet by Semil Shah yesterday:

So I clicked on the link to my Competing To Win Deals post, which I wrote in 2010, and read it. I often read things I wrote a decade or more ago and cringe at how out of date they have become. Not this one. It is as relevant today as when I wrote it almost twelve years ago. So I am reposting it below:


The venture capital business is highly competitive. There is more money out there chasing good deals than most people imagine. It is also true that there are good deals and good entrepreneurs that can’t find anyone to invest in them. That is a failure of the system. But this post is not about that. It is about how a VC can compete and win a deal that many others want.

Here are my rules:

1) Do your very best to connect with the entrepreneur. If you don’t have a great personal connection, you won’t win the deal. Don’t even bother to try to win a deal where you don’t have good personal chemistry with the founder/CEO.

2) Bring your full partnership into the deal process early and consistently. Entrepreneurs are smart and they know they are doing a deal with a firm as well as an individual. Let them see the full picture early. Make it easy on the entrepreneur to meet the full partnership. Don’t make the entrepreneur do all the work.

3) Encourage the entrepreneur to get feedback on you and your firm. Instead of references, I like to give a list of every entrepreneur I’ve ever worked with and an email address. I tell them “throw a dart at that list and talk to four or five of them randomly. you’ll hear the same thing from everyone.”

4) Don’t pressure the entrepreneur to make a decision. Don’t issue exploding term sheets. Don’t put no shops into your term sheets. Those kinds of things are signs of insecurity. I prefer to tell people that we’ll have an exclusive relationship when the deal closes and not before then. If someone wants to leave me at the altar, better it happens then than after we are married.

5) Make your offer in person and don’t do it via a term sheet. Tell the entrepreneur you want to be their business partner. Tell them how much you will invest and how much ownership you want. Leave it at that. Tell them that if they are interested, you will send them a term sheet. Leading with a term sheet focuses the discussion on the wrong things. The process should be all about personal fit and very high level deal terms. Once the decision is made to try to work together, you can get into the specifics of the deal.

6) Add value during the process. Talk about the strategy issues facing the company. Talk about the hiring challenges the company faces. Try to help with these issues even before you are an investor. Show what you can do right away.

7) Use the product or service. Ideally you should be using it well before you start chasing the deal. But use the product/service actively and smartly. The entreprener will be watching. I assure you of that.

8) Don’t feel the need to pay the highest price. Offering a crazy price to win the deal scares off most smart entrepreneurs. They will be wondering why you are so aggressive. Offering a fair price that is in the range is what you need to do. And communicate that if the entrepreneur chooses to work with you, you will be flexible on your offer. That way you put yourself in the position to win and you can work the specifics to close the deal when the opportunity presents itself.

9) Don’t team up with another firm. We’ve made this mistake a few times recently. Entrepreneurs want to choose their syndicate partners. By pairing up with another firm, you signal to the entrepreneur that you want to choose the syndicate and that is a mistake in a highly competitive deal.

10) Be prepared to lose the deal and if you do, lose gracefully. There are plenty of good deals out there. You don’t have to win them all. Lose gracefully and maintain your good relationship with the entrepreneur at all costs. They might come back to you on the next round.

Many of these rules are counter intuitive. But they work well for my partners and me. You might say they will only work for you if you are a top tier investor. That may well be true, but you have to act like a top tier investor to become one. So you might as well play the game that way from the start.

#entrepreneurship#VC & Technology

A Return To Fundamentals

I wrote a fair bit last year about the disconnect between how companies were being valued and the fundamentals of those businesses. It seemed to me that many companies, from the founders, to the leadership teams, and the rank and file employees got more focused on raising capital and valuations than the basics of a business (people, product, customers, revenues, profits, etc).

That is starting to shift. I can feel it. With the public markets bringing high flyers back to reality, you can now buy the best companies out there at multiples of earnings and profits that make some sense in a historical context. And we are seeing reports that many mutual funds and hedge funds are leaving the private markets because the values in the public markets are so compelling. All of this is healthy.

Vitalik Buterin, the founder of the Ethereum project, said this at ETH Denver this past week.

The winters are the time when a lot of those applications fall away and you can see which projects are actually long-term sustainable, like both in their models and in their teams and their people

Vitalik was talking about a “crypto winter” but the basic point is more broadly applicable.

Business models need to be sustainable. Teams need to stick together and ship things. The fundamentals need to be in place for a business to succeed. All the money in the world at eye-popping valuations won’t do that for you.

I have no idea if we are in for another crypto winter. I have no idea if the stock market will continue to go down. I have no idea if the slump in the public markets will seep into the private markets. All of those questions are above my pay grade.

What I do know is that the businesses that focus on the fundamentals will succeed in any market, up or down. And I do feel that there is more of that going on in 2022 than we saw in 2020 and 2021 and that’s a very good thing.

#entrepreneurship#management#VC & Technology

The Great Formation

On Friday, the US jobs report produced a confusing result. From Bloomberg:

The jobs report is composed of two surveys — one of employers and the other of households. The employer survey, which determines the payroll and wage figures, showed hiring slowed across industries, including declines at automakers and retail outlets. The household survey, which determines the jobless and participation rates, showed employment surged by 1.14 million people and many came off the sidelines.

So employers are reporting sluggish job growth (and an inability to hire in some sectors) and households are reporting a huge surge in newly employed.

What is going on?

I don’t know but I have a theory.

I believe more people are going to work for themselves and/or going into small businesses that are not part of the employer survey.

Here is US Census data on new business formation:

What was an upward trend for the last decade has become an explosion during the pandemic.

Maybe what we are witnessing is not the Great Resignation but the Great Formation.

#entrepreneurship

Founder Led Companies

I remember about fifteen years ago, a well-known VC said to me “you need to sell a company within a few years of the founder leaving. Companies can’t sustain their innovation after a founder leaves.” I told that VC that my experience has been different on that measure and that I did not agree.

I have seen leadership teams take over great businesses from founders and get them to the next level. Etsy, where I am Chair of the Board and a large shareholder, is a great example of that. There are many others in my career as well.

However, there is a special something that founders provide companies. I’ve heard it called “moral leadership.” I’ve heard it called “the soul of the business.” I’ve heard it called “long-term thinking.”

This podcast with Brian Armstrong, founder and CEO of Coinbase, another public company where I am on the Board and a large shareholder, is a good example of that.

If you are into crypto or a Coinbase shareholder, you might want to watch the entire one hour and forty minutes of this video.

But if you want to see what I am talking about with founder-led businesses, there are a few conversations in this podcast I would direct you to. They are:

  • 25:48 The Drive and Vision
  • 29:36 The Future of Coinbase
  • 47:30 Public Goods & Decentralization
  • 51:39 Eating All the Banks
  • 1:32:12 Maturing and Growing

#crypto#entrepreneurship#management

Startups Galore

When you look at the recent Q3 numbers on seed and early-stage VC fundraising, you might think we are in the late stages of a VC bubble:

The words I would use to describe the current environment in early-stage VC are “fast and furious.”

And yet the thing that makes me think this could be the new normal and not the late stages of a bubble is the dramatic increase in the number of people who are choosing to work in or form new startups. It has never been easier to start a company, build a team, and build a product. And many people are choosing to do just that.

It could be that we are in an environment where too much money is chasing too many good deals.

#entrepreneurship#VC & Technology

NYC's Tech Resurgence (continued)

A few weeks ago, I wrote about NYC’s Tech Resurgence. I observed that NYC continues to develop as one of the world’s leading centers of tech innovation.

And then yesterday, I saw this tweet:

NYC startups are getting funded at 2/3 the rate of Silicon Valley startups. That’s a huge change from where NYC was even two or three years ago.

It wasn’t that long ago that a NYC-based startup had to agree to move to Silicon Valley to get money from the VCs out there. I think that was still a thing into the latter part of the 2000s. Now a decade and a half later, we see NYC startups raising capital almost as much as Silicon Valley startups.

Wow.

#entrepreneurship#NYC#VC & Technology