Today we had our second Betaday at betaworks in NYC. It was at the Soho House, a posh movie screening house right next door to our offices in the Meatpacking District:

It was a great event and provided the opportunity for media companies and ad agencies to network with the startup community of NYC. One exec remarked that without Betaday, it would be next to impossible for execs to find and connect with these startups. It’s so true; without events such as these, where would they meet young companies like these and look to do potential partnerships with them?
Looking forward to the next Betaday!

The economy is affecting everyone. But it’s also interesting to see how it is affecting my angel investing strategy.
Like all other investors, I sent out my own doom and gloom email to my companies. Here is mine:
——email——————–
Well, I should have been more closely following the blogs, but for some
reason missed this. Of course, you may have seen this already.
I am sure by now I am not the first investor to be telling you this. More
data from a presentation from Sequoia to its portfolio companies. Better
hunker down the long haul. This problem is now worldwide which means it
isn’t just a local US problem. Thanks to some of our once esteemed
financial firms, we’ve now taken down the system worldwide.
Early stage is the most risky. It’s where cash is very scarce, and you
don’t have revenues yet. The problem is the economy is going to be
harshest on all you guys because in a good economy, you may not have
problems.
Make the hard decisions now before you’re laying off people and in
survival mode. Extend your cash as long as you can and work as hard as
possible to get your metrics into a great place. VCs have cash to give,
but they will not give it to you if your metrics aren’t anywhere but
great.
Also, the more you can find revenue that is not advertising based, this is
a good thing. Over and over again, the forecasts for positive advertising
spending have turned out to be wrong.
Read on and see the embedded pres:
http://gigaom.com/2008/10/08/sequoia-rings-the-alarm-bell-silicon-valley-in-trouble/
http://gigaom.com/2008/10/09/what-startups-can-learn-from-sequoias-doomsday-warning/
Thanks for listening…Dave
——email——————–
The Sequoia deck was very enlightening and pretty much says it all. The world has changed; many early stage entrepreneurs are too young to have experienced as adults any economic cycles. I lived through the dot-com boom and bust cycle, and also the other one back in 1990 when the first Bush invaded Iraq. It’s a sobering thing to have done so.
During the 1990 downturn, I was working on a Master’s in Product Design at Stanford. I had completed a summer internship at Apple and managed to land a job continuing my work there, which allowed me to stay on as a full time employee and take a year off from school. The fall/winter of that same year, the US was into Iraq, beating back forces bent on invading Kuwait. Shortly thereafter, the economy goes downward. EVERY ONE of my fellow students in my Master’s program did not get a job for OVER 9 MONTHS after graduation the following June. I was incredibly ecstatic and thought myself super-lucky that I had a job, and one that didn’t lay me off thankfully.
During the dot-com bust, I was at Yahoo and we came through it with a stock that was down to 9 bucks and laying off 1000s of people. If you’ve ever laid off people, let me tell you it SUCKS. First there are all the planning meetings beforehand, behind closed doors to see who would be let go and who would stay. Then the big day comes; everyone is supposed to wait in their cube until the whole process is over. You just sit there and wait, in anxiety, wondering if you are going to be axed or not. When you go and get them, there is a mix of emotions: tears, fears, anger – you have to know how to deal with it all. This isn’t about the people anymore; the corporation exists to survive for itself, not for its people. The harsh reality is that we’re all expendable in corporate terms. No more IBMs with their plush retirement and pension plans, no more thanks for all the loyalty you’ve given the company for 30+ years. If you’re not part of the solution, you’re gone.
Personally I was also extremely lucky again. There were two things that pushed me through the dot-com bust in decent position. First, I was so freakin’ busy at Yahoo that I did not deploy my personal funds into any stocks. Thus, when the markets crashed in 2001, I was heavily in cash. Geez. A bit of laziness saves me from a superb drop in stock market value. Second, I told my broker that whatever funds I did deploy, I did not want to be in PC manufacturers, ie. Dell, HP, etc. I told them that these were now commodity products and that these guys were going to get killed at some point in the near future. Little did I know that during the dot-com crash, these guys took down the value of many a fund, and because I told my broker not to buy these stocks, I managed to keep my stock portfolio breaking even, whereas other portfolios were heavily invested in these companies which just tanked at that crash.
Freakin’ lucky bastard I am.
Now we’re in another downturn. It’s too early to tell what personal moves I’m going to make although I think about it every day and there is ongoing strategizing with my broker.
But it’s effect on one part of my portfolio strategy has been growing clearer. Angel investing at the early stage is inherently risky. But now, the economy is going to make certain strategies even more riskier, and this is compounded by the fact that further fund sources are going to be even more conservative and picky on which companies they invest in. This means that whereas great metrics alone may have gotten you your next round, now it’s not enough.
Early stage startups typically raise about a million. It lasts them for about a year. However, raising money in 2009 is going to be SUPER TOUGH.
Now my strategy has shifted to investing only in companies which are either generating revenue, or have businesses that naturally generate revenue from usage. That means no more exploratory forays into social networks or consumer companies that depend chiefly on advertising. As I said in my doom and gloom email, every positive forecast about advertising spending has turned out to be DEAD WRONG (kind of calls into question forecasting and research in general).
This economic downturn is a worldwide phenomenon now. All our economies are intertwined, and I’m sure many countries counting on the ol’ faithful US to prop up their own economies were slapped rudely in the face. Guess what. Build up your own economy and make it great. Depending on someone else to do it for you is not working!
But it also means that we’re going to take a long time to pull out of this. Early stage is super risky because we can’t give them enough to survive long enough to prove out certain types of business plans. Only the ones who are generating cash from the get-go are going to be the strongest. Everyone else has a greater chance than ever now that they will run out of money before they can prove out their biz models. We don’t know how long it will take to recover, and we don’t know if the bailout plan will affect things quickly or slowly.
So I’m really only investing in clear revenue producing startups now. It seems to be the only thing that reduces risk. By the way, since the economy is way down, it just happens to be a great time to invest since prices will be really low; you just have to have cash to deploy.

This has happened to me several times now. I’ve found an amazing lack of caring when it comes to negotiating terms amongst supposedly experienced investors. This is both among angels and venture firms. It doesn’t happen every time, but it happens enough. I have also found that people who put the most money in have the most to lose, but yet don’t step up to lead a negotiation on terms.
Why would this happen even with seemingly experienced individuals who have put up a large sum of cash for investment? Here are some reasons I’ve seen:
1. There is inherent trust in the entrepreneur. This occurs most in rounds with family and friends. Experienced individuals who jump into these rounds may not negotiate over terms and just sign whatever paperwork comes their way, on the assumption that the entrepreneur won’t ever do anything to screw them.
2. Some investors have lots of money, but don’t have enough knowledge on financing terms and their future implications. In my own experience, the only way I have learned (and that learning is burned into me) is to have done lots of deals and continually do them. Most angels don’t invest that often and it’s easy to forget how terms can affect their investment.
3. Some investors simply don’t care. They just put money up for investment and they are totally passive, and are happy to be part of the deal and gain some sort of return later. They don’t care about the details at all.
With 3, I believe that even at large sums of money, and this can be upwards of 500k-1MM dollars, this still is a drop in the bucket for their entire holdings and thus can afford to not care about the details.
Also, I think that for many investors, they are just doing it as a hobby and they are not serious about it. Thus, their level of care drops considerably on the details.
4. I have also seen investors simply avoid confrontation. They don’t want to get into an argument over terms, so they don’t start.
5. Some investors don’t want to spend lawyer fees to deal with the terms. They don’t want to spend anything extra and just want it done.
6. There is also something more serious, which is that if you lead, you could take on extra liability in case something in the terms causes the entire deal to go sour at some point. I’ve heard of cases where you could get sued for that. So investors get cold feet and avoid leading.
On some deals, I have pushed back on the terms because they weren’t to my liking. I do that even when I go in at my very low investment level, and I am never large enough to be a traditional lead investor. Entrepreneurs often counter that their most experienced investor is OK with the terms and thus the terms must be acceptable. In fact, because the other investors have not spoken up, the terms get accepted by default.
I have to say that this is frustrating. I have met only one other investor who invests at my level and ALWAYS speaks up about the terms. Everyone else just follows whatever is happening and assumes someone else is dealing with the details.
The problem with the terms is that, unless a lead investor produces a term sheet, you’re almost always given a term sheet that is company friendly. It will always favor the company and provides zero protection for investors from negative events.
My message to entrepreneurs is this:
You’re probably doing the right thing from a negotiation standpoint in starting out with a document that favors you totally. But I would truly warn you against making the assumption that since an experienced investor(s) have reviewed it, that it is truly an acceptable document. As discussed before, there are myriad of reasons why an investor, or group of investors, are OK with what you produced. But bear in mind, that if you as an entrepreneur truly want to take care of your investors, then you should query your lawyer on why an investor might object to the terms set forth in the document that he gives you, so that you understand why we would have issues and the ramifications for us in the extreme cases.
By the way, a lawyer will ALWAYS produce documents that favor you initially. It’s their job. If they are being a proper lawyer they will always seek to protect you and the company first UNLESS you specifically ask for a document that is more balanced. Also, NOTHING IS STANDARD. No matter what anyone tells you, it’s true. In every deal I’ve worked on, the terms are always slightly different.
My message to investors:
First, following on the very last comment previous, NOTHING IS STANDARD. Don’t believe it if someone hands you a term sheet and they say it’s standard, in hopes that you will believe them and just accept it blindly. I’ve worked on many deals now and they are all different in small and large ways, with many of the entrepreneurs and their lawyers leading the discussion with “it’s standard”.
Second, hire a good lawyer and spend the money to have someone review the terms and explain to you the potential up and downsides of the terms. Too many horror stories abound where there was insufficient protection for investors and we’ve gotten squeezed out company ownership, cheating us of larger returns. As an early stage investor, we put up cash at the earliest stage and take the highest risk and it is my belief that we should be compensated for taking that risk early on. Without us, the entrepreneur would never have gotten anywhere.
Third, CARE ABOUT THE TERMS. Make sure someone good is negotiating on your behalf. Never assume that someone else is going to do it. If you’re unwilling to do the negotiation, then at least make sure that there is someone who will do the negotiation. READ THE TERMS. Understand their implications to you and your money.
Fourth, we’d all like to work off of trust and a handshake, but I’ve already seen how friends can turn on friends in a business situation. It happens way too much for my taste. Thus, if we have a trusting business relationship, then there should be no problem putting that down in the terms. Be alert for when an entrepreneur gets upset at you implying that their trust is not good enough because you want it written down – to me, it’s a sign of trouble. It’s a psychological tactic to get at your good, trusting nature so that you won’t require him to write it down. Don’t fall for that. Walk away from the deal.
Last, do not be afraid to speak up regarding the terms either to the entrepreneur or to the lead investor. It’s your money so take care of it! Besides, you never know if the entrepreneur might actually change something based on what you say; it’s happened twice to me now where I’m on great terms with the entrepreneur and just asked nicely if we could make a change, and they did it.

Often I get asked by entrepreneurs to become advisor to their company and they take a look at my companies page and they wonder how I can handle so many companies at one time. Where does Dave find the time? Do the companies actually get enough support from me given that I am advising so many?
It’s actually not so hard. Here’s how:
1. I’ve found that advisor time commitment varies greatly from company to company. Some entrepreneurs use me as traditional advisors are used, which is to meet up once every month or quarter and give me an update and go through their plans and get my feedback. If all my companies were like this, I could definitely advise a ton more.
Others call or email me whenever they need something. I have many hours in the day and definitely can field calls or answer emails. Sometimes they ask for a site review or recommendations. This takes longer, but blocking out a few hours to do that isn’t a problem.
Some have wanted meetings weekly for a while. The weekly meetings never last though; entrepreneurs are pretty busy and they get going on something and they don’t have time to meet up any more. Or they learn enough or have firmed up plans enough to keep them going for a while and then they don’t need my constant interaction.
2. Perhaps the greatest time commitment is just thinking about each company daily. I often have at least one (or more) of my companies swirling in my brain and I try to record any ideas down asap. If I am in front of my Mac, I’ll open an email and just record the ideas in that; also, I have a small moleskin notebook that I carry around with me constantly to jot down ideas. Once I get all my ideas down, I check it over, do some rewrites, insert additional ideas that come to me on the fly, and then send it to the entrepreneur.
I like to get into the mode of a single company and its product and try to immerse myself in the product as a user, and the experience of needing/wanting that product. That enables me to really get into what I would want, and also what others could want in that product and where improvements can be made.
I multitask on this throughout each day, but sometimes I take some focused time and do this too.
Still, once a company receives these ideas and acts on them, they usually don’t need further time from me for a while.
3. Another task I do for my startups is connecting them with potential partners and sources of capital (although definitely I do not bill myself as a fund raiser). This requires me to network a lot with both old and newly met folks. Thus hour long coffees and lunches are the norm and these take time out of my week.
Also, I write a lot of emails introducing my companies to these partners as well. Thinking about which partner to send the company to and also sending the email does take up time, but not all that much.
4. My favorite thing to say about advisor time commitment is that almost all companies need the most time at the beginning of our advisor relationship. There is a big spike in time and thinking from my side and also in interactions and then somewhere between 2 and 6 months later, that time drops to near zero, with little peaks of time to do emails and check-ins.
The rationale behind this is that the company is supposed to learn everything I tell them. They finalize their plans with my input and feedback. They take this knowledge and are off and running building their product. They don’t need my interaction so much after this time because they have what they need from me.
This is one of my main goals: To transfer knowledge from my brain to theirs so that they don’t need me any more. If I do this successfully, they should be able to function for a long period of time without my input. Over time, my goal over the term of my advisorship is to help them find resources that would manage what I help them with day to day. This is finding and hiring a great full time design resource and great product management resource. It can also mean finding/hiring a great sales program person as well, to help them monetize their advertising programs.
I’ve been advising for about 2 years now, so many of the companies on my companies page are off and running without further need of my help.
4a. One thing that I have consistently observed is that if my time requirements spikes again after the initial peak, the company is in trouble…so I keep watch for this and hopefully help prevent this from happening.
5. OK OK I admit it. Even working like the above, I still can get pretty busy in the short term. In fact there was a time when I thought I was overextending myself due to the pace of advisorship signups. So now I am very aware of the pace of companies I advise and have slowed down dramatically based on my current support load.
6. Next, I tell people I shouldn’t be put on critical path for anything. It’s not what advisors do anyways.
A lot of people ask me to be advisor, but really want me to do the design of their site for them. If they want this, they should either outsource their design or find a designer to hire full time, and not try to turn an advisor into a fake full time person. I think this is especially true in product design; in order to do a great job, you have to be immersed 24/7 with the product and team. It’s hard to jump in and out or do it on the side.
If I’m not on critical path, that reduces time commitments from 24/7 to something much, much less and less frequent.
As advisor, I always tell people that I shouldn’t be expected to be put on critical path for anything because we’re both going to end up being disappointed and frustrated. Very bad!
7. Last, I love being involved in many things. It helps keep my interest level up and allows me to see the entire world of internet startups across the board, which is an advantage. I purposely try to get involved across a myriad of projects, across a range of areas.
It takes me out of being myopic into one thing, and allows me to help my startups by being broad in my thinking and not get too trapped into the details of one project. While this is important from an execution point of view, it doesn’t help when you’re helping to plan the strategies of these startups by not looking outward and seeing where the trends of the industry are going. Often I bring the broader view to my startups because they don’t have time to look at it themselves. They’re often too busy to do that. On the other hand, I want them to spend all their time executing and not get distracted.
I’ve really come to love advising startups. The connection with smart, energetic people working on cool new things is really great, and I enjoy helping broaden their vision and give them the help and knowledge they need to be successful.

A little while back I sat with another experienced angel investor and the topic of gut feel came up, as it relates to angel investing.
It was funny for both of us that for all the analysis we can do on a new startup’s prospects, that if our gut said no, we’d not invest. How interesting to use such a undefined force and feeling to make such a prominent decision!
After I left Yahoo, I resolved to develop and listen to my intuition more. I really searched down deep inside myself and really tried to become sensitive to the most minute feelings that emerged about anything. I trained myself to be acutely aware of the good and the bad, and those nagging feelings of doubt or uncertainty. Then, once I could identify those feelings, then I told myself that I would act on them and never ignore them. This is because in the past, I feel that I have ignored my intuition and this has resulted in me getting into some really bad situations.
When I meet an entrepreneur for the first time, my intuition is on high alert. I search my feelings as I hear them talk to me about their business. I not only attune myself to pitch he is presenting, but also to who he is. Is there elation on the idea or some nagging uncertainty? Do I feel this person is trustworthy or not? These and more.
However, what can stymie intuition in the world of angel investing is seduction. This is when the pitch and/or the person delivers such an incredible perceived opportunity that it’s like seeing the hottest, sexiest woman walk into a bar and you just can’t resist. You’re hooked emotionally and you’re already reaching for your checkbook. Somehow, the seducer has blown past all your defenses and even your intuition seems suckered.
This happened to me in a pitch not too long ago. The pitch was perfect. It was seductive. It claimed solving so many problems and the benefits and monetization were straightforward. The team was experienced and veterans of the Internet, so no problem on solving any kind of technical challenge. But I countered by saying to myself that hottest, sexiest woman is still a person despite what we perceive is her perfection, and thus means she can’t be perfect since she is only human. Thus, for this pitch, however sexy it was, I refused to fall under its spell and viewed it with objective eyes. I brought my intuition back online and ultimately felt too uneasy about it to participate.
Walk away from that hot, sexy woman – hardest thing you can do sometimes.
Avoiding seduction is crucial. We have to train ourselves to not fall under the witch’s spell and view the entrepreneur and the opportunity with objective eyes.
This brings back the clarity of our gut and intuition, which we must cultivate to make sure we are not doing something that we’re not comfortable with.
In Blink by Malcolm Gladwell, he doesn’t like using the word intuition but instead he calls it a form of unbelievably quick thinking. For me, it’s both. It’s both the gut, the emotional aspect of immediate, primal reaction to something, and the incredibly rapid thought that allows us to make an instantaneous decision. One is cultivated within ourselves and our feelings, the other via years of experience in dealing in a certain area of expertise.
What does it mean exactly when we pass on an opportunity via gut feel?
Just because we pass on an idea does not mean that we think an idea will fail. It might actually succeed. However, I do believe that it truly means that we are not the right people to be involved and that our gut is telling us that, given who we are, how we work, etc, that this project is not right for us.
For the entrepreneur that gets passed due to gut feel, don’t feel bad. In the end, it will be better if we didn’t work together. Go and be successful, but just with someone else.