Angel Investing/Venture Funds: November 2006 Archives

Sometimes I get asked what it takes to be an angel investor. It also leads to insight into whether or not being a venture capitalist is the right career. While I am not an expert at either, I do have some observations from the many months I spent trying to raise a venture fund and now ending up as an angel investor. These observations are by no means complete or exhaustive, but for now I think they serve as one man's look into the world of investing in startups. These are the results of conversations, feedback, and personal thinking and experiences:

What Does it Take to be a Venture Capitalist?

Beyond that magical ability to pick companies/businesses/the next Youtube, there are a number of things to be aware of.

Investors need to trust you. They are handing you their millions of dollars and want to have maximal assurance that you'll not run away with it, make stupid or poor investment decisions, keep to discipline (which is what you sold them on investing in your fund), and want you to do better than the next guy.

If you've created companies and built them to success, that's a plus. But it's only one piece of the puzzle. Building a great company doesn't mean you can go and pick other companies that will win. Investors like to see that you have engaged in activities that show you can pick successful companies AND make lots of money from it. The 'AND' is important; just saying "I knew Youtube was going to be big" isn't the same as saying "I bet on Youtube when they are two guys in a garage, put my money in it, helped them with XYZ when they needed it, and saw the potential and put my own money where my mouth was, and made 10X on my investment."

How to develop a track record? Angel investing helps, as does working in investment banking or some other similar investment outfit. If you've worked with other prominent investors like in an angel network, that's great too. People who have invested alongside you and made money off your introduction of a company to them is a great trust builder. Experience as an entrepreneur also helps but not as much as (successful) investing experience. (Working in a previous venture fund helps a lot, but hey this paragraph is about whether or not you should be a VC in the first place.)

If you are thinking of joining a venture fund, they need to also trust you, see your commitment, and they have to like you and be able to work with you.

Joining a venture fund is not like taking a job at any other company. With a regular company, you can quit at any time and go to a new company. The commitment is typically 5 years, with potential to extend to 10 years if you still have companies in your portfolio that you have not exitted out of. This is spelled out in the Private Placement Memorandum (PPM) and is a condition for investors to commit. If you decide to leave the fund before the 5-10 years are up, this can, at a minimum, cause uncomfortable questions in investors minds as to the viability of the team they put their money in. It can, at a maximum, cause all the investors to bolt and your fund is left with nothing.

Therefore, venture fund partners want to know that you're in it for the long haul no matter what. It's pretty tough; 5 years is a really long time to commit. You'd really have to want to do it that long and the moment a partner smells wavering commitment, they'll back off you.

Since you're in it for a long time, you want to know that you can all work together and also must like each other. Again, 5 years is a long time to be hanging out with someone. You'd better all be drinking buddies as well as love working with each other to stand each other's company. That is why a lot of venture funds are made up of partners who have known each other for a long time and have worked with each other in the past. Investors like this also; they want to have assurance that the team can function together well and prevent an unrecoverable implosion of the team at some point in the future. They want to know that the team will exist long enough to make them money for the period of time they commit.

Lastly, almost all venture funds require the partners to put up their own capital. I've heard 1% is the norm, but I've also heard it can be higher as well. Doing some quick math - if your fund is $100 MM, you would need to put up 1% of $100MM which is $1 MM of your own cash. It doesn't have to come all at once; venture funds do capital calls when an investment is imminent. So the cash would come in portions as you went out and found companies to invest in. But over 5 years, you'd have to find $1MM to invest. All is not lost; a venture fund has many partners, so the 1% is spread out amongst all the partners. Still, it could mean many 100s of thousands of personal money to commit to the fund, in order to gain trust of the investors. How many people have that kind of cash lying around?

So after reading this, does the above apply to you in the positive sense, if you aspire to be a venture capitalist?

What Does it Take to Be an Angel Investor?

Simply put, being angel investor requires nothing more than cash. I don't think there is any other requirement than that. Of course, if you want to be GOOD at it, you'll need more than that. Read on..!

Things That Apply Both to Angel Investing and Venture Capitalists

Beyond those mentioned above, you will need to be able to pick companies well. The topic of picking companies is beyond the scope of this post, but no matter whether you're an angel or a VC, you have to do this well. You'll probably want to have some expertise in the area that you are picking companies in, like for me I work on Internet companies because that's what I know most about.

Having an extensive business network really helps. Connecting your entrepreneurs with the right folks will help from a company building standpoint, and even potentially on generating an exit at some point in the future. When you are calling on your friends or previous business associates, it works much better than going in cold. They already know you and there is a level of trust built already.

You also can't be risk averse. You need to be more of a risk taker and be able to get behind an entrepreneur, even when there seems to be no intellectual proof that it will be successful. Startup investing is not for the conservative soul; you'll drive yourself crazy if you are conservative by nature.

The Money Aspect

Here is where it differs slightly between venture capitalists and angel investors. When you are a VC, you are playing with other peoples' money; when you're an angel, you're playing with your own money. I say 'slightly' because in the case where you have to put up your money into the fund, then you'll also be playing with your own money as you invest the fund's money.

But with a fund, the bulk of the money you're investing is not yours. So if this is true, you need to feel some kind of fiscal responsibility to that money, and not feel that you can just take unnecessary risks with it. After all, these people entrusted you with their money on the assumption that you wouldn't just piss it away on stupid investments.

When it's your own money, other things come into play. I'll throw some out there which I think are important.

Most financial planners say that you shouldn't put more than 2-3% of your assets into any one investment. This ensures diversification minimizes the impact of any one investment in case of a downturn in that investment. In either case of whether you're committing money into a fund or designating it for angel investing, is that amount larger than 2-3% of your total assets? If it is, you are potentially taking too high a risk with your assets. Investing into these types of companies is not a sure thing. The potential is greater than zero that you could lose it all.

Still, it has been shown that statistically speaking, if you put money in 10 investments, about 6 will tank, 3 will break even or make back a little, and the last one makes back everything you lost on the previous 9 and then some.

Let's do some math: say you put $50K into 10 companies because you want to employ this diversification concept to maximize your chances of making money. That means you need $500K to do this. If we say that we don't want to commit more than 2% of our total assets, then our assets must be $25MM total.

Certainly this can be modified by many factors like are you a risk taker or not. Maybe then 2% isn't the right number but maybe 4 or 5% or maybe more. It definitely bears some thought into what kind of person you really are, and the comfort level you need with respect to your assets.

I think also that you need to be able to let go of that money. You need to be able to say that you will be OK if you never see that money again and just move on. If you cannot let go of the cash emotionally and intellectually, you'll be in a really poor mental state when your investments aren't doing well. Remember, that even if you employ the diversified/statistical method of investing, something like 6 of those companies will fail completely. I would not recommend you get into venture or angel investing if you're going to collapse mentally every time one of your portfolio companies dies. You'll go nuts and probably drive everyone else nuts around you. Because it WILL HAPPEN and you need to be able to deal with it.

You also need to have a healthy attitude towards money. Some people just can't. They assign way too much importance to cash in their lives. They can't let go of it, and they may do a Dr. Jekyll/Mr. Hyde thing on you. I've already experienced this once already in my life, and I have heard stories about many more. Friends, family all turning from loving people to the nightmares of your life. They will do things like hate you for losing their money, and never let you forget it. They will lie, cheat, steal - literally money does bring out the worst in people. Are you a closet Dr. Jekyll/Mr. Hyde with respect to money? If you are or even think you are, stay away from startup investing!

What's Your Real Motivation?

I am big on getting real insight into why I do anything. I want to really understand my motivations and feelings on it. So I think it is worthwhile asking yourself why you REALLY want to do this. If after all your inward analysis you still want to do this, then by all means go for it assuming the other stuff we talked about applies positively to you.

One big thing is to not delude oneself about the glamorous life of a startup investor. It ain't glamorous all the time and it takes a lot of work to do it well. And as much as you may say you want to build great companies, you won't be able to ignore the monetary aspect of it and how you're going to get your money out of the deal. Sometimes the two don't sync up exactly and you need to be ready to make a decision contrary to what you really want. You need to prepare yourself on the realities of what is going on here. Can you take your blinders off and really see what it takes realistically?

The Last Word

The last thing I'll say about whether you can be successful at this is: Are you a lucky person? By fate, or by creating your own luck (which I am big into - creating opportunities rather than just sitting back and hoping it will happen), I think luck plays a bigger role than people think. It is that slight edge you get by the will of the gods that will enable your video company to succeed, whereas the other 99 will not...

Really the Last Word

Don't create the 100th video company when there are 99 out there. But if your video company makes it big; then I would say you are lucky. Go invest more and call me to bring me into your next deal (haha).

I've learned a huge amount about angel investing over the last few months. It started with me sitting down with my lawyer and getting a brain dump of terms, term sheets, provisions of all sorts, talking about notes and preferred series: the list goes on and on. But it's all theory until you get out there and try to invest in something yourself.

I told myself I would try to be a sophisticated investor, meaning that I would spend the time (and money) to get every deal reviewed by my lawyer and I would make best efforts to read everything. It was the only way I could understand everything, which was to experience it in real time.

When I started looking at deals, many things emerged. Here are some of them:

It's the Wild West

There is no such thing as standard. All term sheets have similarities, but everything is different, sometimes subtly different. Every law firm has its own style and favored terms to present, and modify that by the entrepreneur or the venture fund and you get every kind of combination of terms you can think of. All I can say is that I'm glad to have my lawyer around to look at terms with an experienced eye, and I can only hope that over months (years?) I too can gain enough experience at looking at terms and their ramifications.

Law Firms Protect Their Clients

And that's a good thing. The law firms that startups hire will produce documentation that is always company friendly. Which usually means that it's not very friendly for the investor. The terms will inevitably have provisions that don't protect the investor at all. This confounds the process because sophisticated investors will always push back and alter the terms. If there is pushback, then legal fees will mount, as the process of negotiation goes back and forth on the terms.

The downside is that entrepreneurs are typically new to the financing aspect. They don't know enough to ask for more balanced terms when developing term sheets. They just take whatever the lawyer gives them.

I always push for balanced terms that favor neither investor nor company. In my limited experience, it has resulted in the fastest way docments get approved and signed with minimal fuss and cost.

Money Gives You the Lead Position

One thing I found out was that at the amounts I'm angel investing ($25K - $100K per investment), I am typically not the lead investor. That unfortunately means that I have little leverage to modify the terms; if I had put in more money, the entrepreneur is incentivized to negotiate with me and keep me happy in order to get my cash. If I am only putting in a small amount relative to others, or as a percentage of the total raise, then it is up to me to do my best in gracefully pushing for better terms.

Sophistication or Attention to Detail is Severely Lacking in Angel Rounds

During angel rounds, it is often the case that the entrepreneur went to their friends and family to get much of the money. These folks have cash, but almost always have no experience with terms and what is good and what is not. They rely solely on trust of their family/friend to not screw them when it comes to protecting their investment. When I arrive on the scene, it is often the case that a lot of the money has already been raised, and now we have a whole crew of people who have accepted the terms, albeit not fully understanding them, and now I have little leverage to ask for different terms because the entrepreneur would now have to go back to each investor and approve and sign off on changes. This will incur extra costs and perhaps even uncomfortable dialog between the entpreneur and family and friends (ie. you asking for my approval for better terms now...? why weren't they in there when I signed the documents in the first place...?).

Big Experienced Angels Mess Up the Process for us Little Guys

Another issue I have encountered is the prevalence of angels in Silicon Valley with large sums of money. Throwing $50K, $100K, even $1MM into a startup during an angel round is done without attention to terms. How do I know they aren't reading the terms? Because they invested in a company with investor un-friendly terms! And with the amount they put in, they could have easily negotiated changes in the terms.

Now that the entrepreneur has a big investor signed up, I show up with my investment and again I don't have leverage to change terms, even if they favor the big investor, because the entrepreneur doesn't want to go back and re-approve terms.

I asked around as to what these guys were doing. I found out that many have 40+ investments. With that many investments, it is impossible to keep their attention on any of them. And some of them are not experienced enough to know if a given company is good or not. Remember, this does not mean that they aren't smart; it just means that sometimes you're putting money in an industry that you may not have deep experience in. So they spread out their investments as much as possible in order to employ what I call the "Random Method of Investing". Basically, this means you employ the theory that has been proven time and time again by venture funds, which is that for every 10 companies you invest in, about 6 will tank, 3 will do about even, and the last 1 will make back all that you lost and then some. Now you can see the reason for 40+ investments. It's very much a passive investing operation.

My bet with David Shen Ventures, LLC is that I will improve that success ratio by being smart about the busineses I involve myself with, and I get involved with them to give them the benefit of my knowledge and experience. I am betting on an active investing operation and I hope to prove that this will be more lucrative than the passive route, as well as more fun.

Timing is Everything, But Not the Last Word

So far, in every investment I've done where I came in middle or towards the end of the round period, I generally have found that I lose leverage to change the terms. But I ask anyways. And it looks like dependent on the entrepreneur; often they will make best efforts to make changes or even make the change.

When I am at the beginning, I find that I can negotiate much better, even with my small amount going in. Over time, I hope to generate proof that going for funding with balanced terms results in lesser negotiation, less cost, and faster fund raising.

What's the Future?

I think the route that others have taken may be the best. And that is to employ enough capital to be the lead investor in the round, angel or otherwise, and to be able to effect change in the terms because you are bringing so much cash to the table. Definitely, I am not there yet; my hope that is David Shen Ventures, LLC will be successful over time to be able to make succeedingly larger investments to the point where I can manipulate terms to the benefit of both investor and company.

The concept of an incubator keeps coming up in my travels. Everybody knows about the big Internet incubators like IdeaLab during the Internet boom years. Lots of investors pouring money into these operations, big plans and huge infrastructure was built to support the development of business ideas, on the assumption that certain resources could be pooled together and shared to increase efficiency and cost. These were building space, internet access, servers, expertise - you name it and you could find it at an incubator in the late 1990s.

The spectacular demise of these incubators put a damper on the creation of new huge incubators. Even now, the lawsuits still go on where angry investors, having lost hundreds of millions of dollars in these investments, are litigating to get some of that back. When I started into this investing business, my ex-venture fund partner and I tried to form an incubator called Ignited Brains where we would employ inexpensive outsourcing to Internet ventures and try to let the marketplace decide on their viability. When we went out to get advice on our operation, we were met unanimously with negativity; incubators, we discovered, was a dirty word in the venture/investing community. Nobody wanted to have anything to do with us at all, which caused us to switch gears to try to raise a traditional venture fund.

As we worked on our traditional venture fund, we also discovered that incubators did exist in other forms. Some venture funds developed the concept of Entrepreneurs in Residence (EIRs), where entrepreneurs with a track record got office space and sometimes were paid staff and they were free to work on whatever projects they wanted. If they were on to something good, the venture fund would then finance it and off they would go. In fact, we had an "lab" in our venture fund which we would activate, with permission of the investors, to operate essentially as an incubator for our own ideas. Another interesting model came up with YCombinator where the two principals would get college students to work with them for 3 months and they would fund them for that time and help them get an Internet business prototype out the door. This is interesting to employ college students who have lots of energy, are super smart, and have skills to throw at a given problem. Another incubator model was tried by those who came through the Internet years with at least one large exit, and thus could fund their own ideas. Basically, they would get some of their smart buddies together, form an LLC or corporation, and work on an idea with minimal cash to see if they could get traction with it.

For me, I think I would have tried the last model, which was to take my own ideas, form a team, and run with it to see if it would work in the marketplace. Upon further thinking and research into this, I think there are limitations on this model. In short, my belief is that you can't work on many ideas, if they are your own AND expect them to be successful in the way you envision them.

The problem has to do with resonance with an idea, and transferring that resonance to other people.

First, an idea has to resonate with me. I must love the idea, understand it, and know how it could be successful. So naturally, I get how to make it work, what a target user might want from it, how to market it, etc. You might say I would be a natural to lead the business.

Herein lies the problem. You can only work on so many things so that they get enough of your time and benefit of your ideas and leadership. It's pretty hard to be CEO of one company, let alone 2 or 3.

And you can't rely on others to take your idea and run with it. That's where the transferrence of resonance comes into play. Since everybody is different, it is a very rare event, in my experience, to be able to transfer your own resonance with an idea to another person so that they feel it as deeply as you do. Without that shared resonance in others, they'll never be able to take an idea to the place you can take it to.

Over the years, in various jobs, I've tried to sell concepts time and time again. And I can't recall a single time that an idea survived longer than me driving it. As soon as I stopped working on an idea, it was impossible for the people there to continue work on it. I believe the same applies to incubators. In fact, I talked to an entrepreneur who actually launched a personal incubator with all his own ideas in it and he also had the same experience I had, which caused him to kill all the other projects and focus on the last two. Once he did that, the two are now flourishing, whereas previously they were actually languishing without his focus on them.

If someone can figure out how to transfer resonance to others, please let me know. Otherwise, are we ADD entrepreneur types doomed to only work on one or two things at a time?