Posts from life lessons

Routines

I am often asked for advice on productivity. People want to know how I get things done.

The truth is I am not well organized, I don’t use any productivity tools.

I work hard but I don’t work all of the time. I have a decent work life balance.

My secret, if I have one, is routine.

I try to do the same things at the same times every day or every week.

Some examples:

– I like to meditate first thing after I wake up.

– I like to handle personal financial matters on Saturday mornings (something I learned from my Dad).

– I need to blog before I leave home or I have a hard time getting that done.

– I work out before breakfast.

When I stick to my routine, I seem to be able to get a lot done.

When I get out of my routine, things fall apart quickly. It is like dominoes. One falls down and knocks down all of the others.

There are challenges with relying on routine. Lots of traveling, for example, makes it hard to stay in a routine.

But I have not found any organizing principle more powerful than routines and I try to apply them to as much of my life as I can.

The Send To All Mistake

I believe I’ve written about this before but I see it made so often that I feel compelled to write about it again.

Entrepreneurs, VCs, and others in the startup ecosystem often send an email introducing a company to all of the partners (or most) at our firm. And that email is addressed to all of us, not one of us.

The result is that none of us feel ownership in the introduction and though we generally figure out who should reply, it can result in the email going unanswered for a while or longer.

On the other hand, if an email is sent to one partner, with possibly a copy to others, then the recipient feels a responsibility to reply and the email is generally answered.

I send emails to busy people a lot. And what I have learned is that I need to address them directly, write the note personally so that it is obvious that I have written it myself, and then copy someone (usually their assistant, but often a colleague as well) to make sure they see it.

Email is such a challenging medium to operate in that when using it, you must be very careful to optimize the chances of a reply.

Sending an email to all is generally not a form of optimization that works.

“If The Train Is Delayed, Find Another Way Home”

I worked for a man named Bliss McCrum (and his partner Milton Pappas) in my mid 20s. They taught me the venture capital business. They were in their 50s, around my age, at that time.

Bliss one time gave me this business travel advice. He said, if the train is delayed or stops at a station and can’t move, get off the train and find another way home. His experience told him that once delays start happening, they tend to get worse, and you are better served by ditching plan A and finding a plan B.

I have used that advice many times over the years, and while it is not perfect, it has been on point more often than off point.

Today I had a 6:30am flight to SFO from LAX. When I picked up my phone as I was leaving the house for the airport, I saw a text from Alaska Airlines that my flight had been cancelled and they were booking me on the next flight.

Bliss popped into my head and I thought, “I’m going to get to LAX and get on the 7am flight that I usually take.” I had wanted to get to SF super early today so I booked the first flight out of LAX to SFO instead of my usual 7am flight.

Once I got to LAX, I was able to get onto the 7am flight, and then headed to the gate where my new flight was leaving from. That required getting on a bus and heading to a new terminal. This is what the guts of LAX look like at 6am.

Once I got to my gate, I learned that my 7am flight was delayed into SFO by 90 minutes, thus pushing my arrival back two hours from when I wanted to be there.

Again Bliss entered my head and I thought “what about San Jose?”. So I went to the board and saw that there was a 7:30am flight getting into San Jose at 8:50. I went to the service desk and asked if there were any delays getting into San Jose this morning and was told there were not.

So I swapped my SFO ticket for a SJC ticket and got basically the same seat on a similar plane.

I’m in the air to SJC right now and hope to land in about 30 mins\utes and then get in a car and be taken the hour+ that it will take to get to into San Francisco. But at least I can call into the start of my meeting instead of missing the first couple hours completely.

I have to thank Bliss for the inspiration to scramble today instead of just taking what the airlines were giving me and being chill about it. I think it worked out well and I’m going to be able to participate in the entirety of my meeting today. Thanks Bliss.

Taking A Stance

As is always the case, I got a lot of feedback on yesterday’s predictions post. Most of it was constructive. Some of it was fawning (yuck). And some of it was snickering.

That’s how it goes when you stick your neck out and take a stance, make a bet. I am used to it.

I am surprised at how few people are willing to do this sort of thing. They have opinions, for sure, but they don’t put them out there and get the reactions that help shape those views going forward.

I would encourage everyone to share your views, opinions, and predictions publicly. It is a practice that produces great value for me and I think would produce similar value for others.

Speaking of predictions, this one on crypto from Arjun Balaji is quite good (and quotes me too 🙂

Today is a back to work day, so I am going end this now and do that.

Litigation

Litigation is something I try to avoid. It is way better to work out differences by sitting down and negotiating a reasonable deal for both parties.

But litigation is a fact of life in business. You cannot avoid it all of the time. Companies and people will sue you even when you have done nothing wrong. So you need to have a framework for thinking about litigation.

Here are some of the things I have learned over the years:

1/ Litigation is expensive and can go on for a very long time. There is no sense of urgency in litigation. You can easily spend more money litigating than settling. If you can settle for less than the likely litigation expense, even if you have done nothing wrong, it is usually better to hold your nose and do that.

There are some people who argue that regularly settling for less than litigation costs will give you a reputation as someone who does that and it will make you a target for lawsuits, often baseless ones. I understand that argument, but I still think settling for less than likely litigation costs is generally the right approach. 

2/ You can lose in litigation even when you have done nothing wrong. I have a friend who is a litigator and he advised me a long time ago that “assume you have a 50/50 chance of losing, no matter how strong your case is, and then you will tend to make the right business decisions.” His point is that you should not fall back on the comfort of a “strong case.” Life is not fair. You can lose when you should win. Plan for that.

3/ Litigation expense is leverage in litigation. Early on at USV, we ended up in some minor litigation. We spent a lot of money on discovery and the other side figured out how to spend very little. We got very far over our skis on the case and we ended up settling on very favorable terms for the other side. We let the other side use expense to their favor. I promised myself I would never do that again. But I see companies we work with do that all the time. It is very easy to want to “lawyer up and fight” and often that is not the best strategy. It can be better to do the rope-a-dope and let the other side spend all of their money and get over their skis.

4/ There are times when you have to fight even if you can settle. If settling a case would materially harm your business, to the point that you would have a hard time operating it, then you must fight. These are existential cases. They are very rare, but they do come along once or twice in a career. When one like this comes along, “lawyer up and fight” is the right strategy and you should amass the best legal team money can buy and you must do everything you can to win. Figuring out when something is existential is the key. Often things feel existential when they are not. That is where the mistakes are often made.

5/ There are lawyers who are great business advisors. I like the term consigliere for them. And there are lawyers who are great litigators. Make sure you have both of them working for you in a litigation. If you can get a consigliere in your company as your General Counsel, you will be way better off in litigation. If you can’t afford that, have one on your board or in your life. The consigliere will help you manage the business side of the litigation and the litigator will manage the legal side of the litigation. It is hard for a business person to manage a litigation without a lawyer at your side.

Those are few of the things I have learned over the years. But my first rule of thumb is to avoid litigation if you can. It really sucks.

PS – I realized after re-reading this post that I left out something very important. Arbitration is an excellent replacement for litigation. Think of it as “litigation light.” It is very important to have arbitration clauses in your everyday contracts (employment, construction, sale of software, provision of service, etc). Arbitration clauses require arbitration in lieu of full blown litigation in the event that there is a dispute over the contract. Arbitration is like litigation in that you can lose even though you did nothing wrong, but it will cost you a lot less time and money to reach a resolution and if you lose, the damages are often a lot more reasonable.

Track Record

I’ve had a few conversations in the last few days about a VC’s track record, which is a schedule of investments over the years with the wins, losses, and everything else.

I was seeing an old friend who has been in the VC business as long as I have yesterday. We got to talking about the notion of a track record. I told him that what is most valuable in a track record to me is not the gross returns, IRRs, or even big winners. What is most interesting and valuable to me is the cumulative experience you can see by looking at the track record. You can see how long someone or some firm has been at it, their mistakes, their successes, how they have evolved as investors, style changes, risk appetite, and a lot more.

Then this morning, I was talking with one of my partners about USV’s track record and we both were cringing at some of our big mistakes. Neither of us were focused on the winners. We were just stung by the mistakes. 

And I think that’s important. We should not stare too much at our big winners. We don’t learn that much from them. We should stare at our big mistakes, because we do learn a lot from them.

I am proud of USV’s track record. We have produced fund after fund of strong performance, something that is not easy to do. But I don’t think that is what differentiates us in the market. And we rarely talk about it with entrepreneurs. We do talk about the difficult lessons we have learned over the years and how those lessons may allow us to help them avoid a similar fate. And, ironically, maybe that is what allows to produce the track record we have.

Giving Thanks

Happy Thanksgiving Everyone.

I appreciate the annual ritual of surrounding ourselves with family, making a big dinner, and enjoying all of that.

I also appreciate taking some time to look back on things and be thankful for what we have.

I am most thankful for what I have around me today, my wife, who makes everything better for everyone around her, and our three fantastic children.

But I thought I would also talk about something that has helped me a lot in the past year – taking a more meditative posture to life. I started meditating last fall and have now been doing it every day since then. But that’s only part of what I am talking about. I am also talking about doing yoga two to three times a week, and making the most out of those sessions. And then taking all of the experiences and sensations and feelings that those things give me and introducing them into the rest of my day.

I have always been high strung. I throw myself at the world and keep throwing myself at it until I am exhausted. That personality has made me who I am and produced much of the success I have enjoyed. But it is also the source of the anxiety and worry that I have experienced regularly and, at times, acutely.

Breathing, deeply and repeatedly, and taking it down a notch and sitting with that feeling is something I wish I had learned as a child. I am sure that there were people who tried. But it took me until my mid 50s to really get it. But now that I do, I have found a balance to the “go go go” way of life that I still live and enjoy.

I am very thankful for that.

Mementos

I keep little things that remind me of events over my career in venture capital. And I have been doing that for most of those thirty plus years. I keep them on a bookshelf I have in my office at USV.

It started with the lucite “tombstones” that bankers would make up when a deal closed. I started collecting them in the late 80s and had them on my bookshelf until recently. I finally got rid of them. Over time, I moved onto more interesting things and started putting them on the bookshelf.

I moved offices at USV this fall and I had to put my bookshelf back together. I did that on Saturday afternoon this past weekend.

The new configuration looks like this:

The third shelf has my collection of useless consumer electronic devices that were a big deal at one time. I have a Apple Newton there, a first generation Blackberry pager style device, and a whole lot more.

I have a bunch of family photos and things my kids made for me over the years. The peace sign painting on the left of the third shelf was made by my daughter when she was ten. I love it.

I put my old Mac desktop on the right corner of the second shelf. I plan to put some digital art on there but have not yet gotten to that.

It took me about three and a half hours to put everything back on the bookshelf on saturday. I had to wipe stuff down to get the dust off. Dusting off memories, literally.

There are a few gems that I had forgotten about. The lighter that Jerry and Dan brought back from Beijing when they did the diligence on Sina.com in the late 90s. The matchbox Porsches that Mark Pincus sent me when we exited Freeloader. The “move to NYC” booklet that Rob Kalin made to convince engineers to leave Silicon Valley and move to the greatest city in the world and work for Etsy. The Dick Costolo mask (partially hidden on the upper left) that the entire Feedburner board put on before he walked back in for exec session. I chuckle every time I look at that one.

I have a ton of stuff that did not make the cut this time. Including all of the lucites. I can’t throw them out so they will collect dust in a closet somewhere and drive the Gotham Gal crazy.

Memories are important. A career of memories is a blessing. And I like to live with mine. It reminds me why I do this work and why I love it so much.

Broken Syndicates

One of the most challenging situations in startup/venture capital land is the broken syndicate. It is not a topic that is talked about much, but it is fairly common, particularly for companies that succeed in building a business but falter at achieving escape velocity.

A syndicate is a group of investors that come together to support a startup financially. They tend to be built over time. Some investors get involved with a company in its seed round. Others get involved in a company in the Series A round. And some get involved in the Series B round.

By the time a startup has raised three or four rounds of venture capital, it is likely to have built a syndicate of between three and five venture capital firms and other investors (corporate, strategic, individuals, family offices, etc).

The idea is that the syndicate supports the company financially until it no longer needs capital. That can happen via a sale of the company, an IPO, or achieving profitable operations.

And that is typically what happens in the best situations, when the company executes well and finds that happy financial chart that goes up and to the right with a steepening slope. In companies like that, the syndicate almost always sticks together and more investors clamor to get into it.

And then there is the company that never really figures out how to build a business. In those situations, everyone around the table, including the founders, figure out how to wind things down, either through a sale of the business, an acquihire, or a wind down. This happens all the time and is generally not a particularly painful process.

But there is a middle ground, where the team figures out how to build a business with customers, revenue, and lots of employees. But often the business stumbles and revenues flatten and losses pile up and more capital is needed, often a lot more than the existing syndicate is prepared for. This is when there are often management changes, founders depart, and there is a lot of drama.

And holding a syndicate together during the “stumble” is very hard. Some investors are managing huge funds and need exits that will produce hundreds of millions to their fund. When they see that a company will not do that, they often move on. Some investors have small funds and don’t have the capacity to fund a company round after round. Corporate and strategic investors can lose interest when a company stumbles and they no longer believe the business is strategic to them. 

Those are the “rational” reasons that syndicates break.

But there are other reasons. There is a fair bit of churn inside venture capital firms right now. Younger partners leave to start their own firms. Or are asked to leave because they are not producing the expected returns. When a partner who leads an investment inside a venture capital firm leaves, the investment is often “orphaned” and the other partners will pretend to support it but they really don’t want to and don’t.

Or even more upsetting is when a venture capital firm finds another company in the same sector that they like more and they lose interest in your company and stop supporting it.

All of these things happen to companies who stumble and they happen way more frequently than anyone talks about. It really doesn’t benefit anyone to go public with these situations. So they are worked out quietly.

Often broken syndicates lead to early exits, when the founder(s) and remaining investors realize that they are screwed and decide to find a home for the business before they run out of gas. Many times these exits are disappointing outcomes relative to the opportunity and they can make for fantastic acquisitions.

Another thing that happens with broken syndicates is the recapitalization. This is when the remaining investors reset the valuation in order to bring in new capital, either from their funds or ideally from fresh sources of capital. The losers in this situation are the early investors, founders, and investors who walked away. 

And sometimes what happens is the business shuts down, leaving people scratching their heads. Why did that company which had lots of customers, revenues, and employees suddenly close up shop? Well the answer is often that their syndicate broke and they could not put it back together.

At USV, we have worked through these stumbles and broken syndicates many times over the years. We often find ourselves in the position of trying to put Humpty Dumpty back together again. We have managed to do that many times. But we don’t manage to do it every time. 

It is incredibly difficult work, probably the hardest work we do in the venture capital business. And we often are asked why we bother.

We have found that we can make excellent returns when we stick to our conviction around an opportunity and work to restructure the team, the operations, and the syndicate (and the valuation). We also have found that we are rewarded reputationally in the market as investors who are supportive when times get tough. And we believe that it our job to support companies and the founders who create them.

We wish everyone in venture capital land saw things the way we do, but they do not. And that is the reality of the world we operate in. 

Founders need to understand all of this when they put their syndicates together. You should ask around about the investors who want to put money in your company. Look for companies that have stumbled and get to the people who know what happened in those situations and ask about how their investors behaved. That will tell you a lot.

The bottom line is that syndicates are fragile things. They break. And putting them back together is hard. So figure how to build one that is strong and will stay strong. The best way to do that is to under promise and over deliver on the business plan. But you can also do yourself a lot of good by finding resilient investors and getting them into your cap table. So do that too.

Jet Lag

Jet lag is such a challenge for me.

We got back from Japan four days ago and I was doing great.

I figured that I had it beat this time.

Then last night at 2am, I woke up and I was wide awake.

We’ve got a series of meetings today that I need to be coherent in.

So I took a half a pill and got back to sleep by 3am and slept until almost 8am.

The good news is I am rested.

The bad news is I don’t have this thing beat like I thought I did.

I have tried a bunch of things to manage jet lag over the years, many of them recommended by folks here at AVC in reaction to a post about this I did a few years ago.

And they have all worked, to a degree.

But, I think the truth is, at least for me, that it takes me about a week to get truly back to normal after a long trip to Asia.

And as much as I thought I could shorten that timetable, I don’t think I can.