April 2009 Archives

On Hacker News, someone posted that they could not find a good tutorial on becoming an angel investor. As I wrote in my previous post, "What I've Learned in Angel Investing, March 2009", there is practically no one to teach you or we're all too busy to hold your hand. So I thought I'd write a bit about starting out.

I thought about writing a whole tutorial, but I kind of backed off on that. I've only got about 2+ years of angel investing under my belt; hardly "expert" status on this topic! There are plenty of people who have been doing angel investing for decades and would be much more qualified to teach angel investing than me. However, I thought about what I could do to help budding angel investors start out and figured that I'd start by talking about whether or not you have the basic qualities for becoming a successful angel investor.

Don't Get Caught Up in the Glamour

Angel investing is glamorous. It's like sitting at the Monaco blackjack table that has a minimum of $10000 per bet. People look at you as if you're some rich celebrity. It's the same with angel investing. People think that you're going to make it rich as you go find the next Google and make a gazillion dollars. In fact, they think you are making a gazillion bucks even as they talk to you.

I would be the first to say that I get some attention for angel investing. But that's because they always hear about the great successes of venture capitalists and startups getting acquired or going public. They never hear about all the other startups that fail miserably, and taking investors' money with them down the tube.

So if you are thinking about becoming an angel investor because you think it's glamourous and you'll gain fame from it, I think that's fine but I can probably think of other less money-wasteful ways of gaining fame (for instance, join Twitter and challenge Ashton Kutcher to see who gets to 2MM followers first). Personally I would not become an angel investor because of this reason so don't get caught up in the glamour.

What is Your Reason for Angel Investing?

I think you need to think hard about why you'd want to angel invest. I would also suggest that you should have alternative reasons for angel investing beyond making money. That's because angel investing is probably one of the riskiest ways of making money and betting it all on this as an overall portfolio strategy.

So have other ways of gaining return from angel investing since there is a good chance you're going to lose all your money doing it. Feel good that you're getting something back from it even if the money doesn't.

My alternative returns from angel investing are:

1. I love hanging with smart entrepreneurs.
2. I love learning something new.
3. I love teaching and get joy from watching others learn.
4. I love being part of something growing.
5. I love the challenge of the process of startup and product building. I love the brainteaser aspect of trying to solve this problem.

You Need Money to Angel Invest

Angel investments range typically in the $25K-$100K range but can go lower or even much higher, upwards of $1MM. You can just do a few angel investments, or even one. But this substantially increases your risk of losing your money. To maximize your chance of making your money back and hopefully a bit more, you should consider that you need be able to make at least 10 investments to spread your risk.

Ideally you'd have a minimum of $25K x 10 = $250K to deploy. And the amount goes upwards from there depending on your target investment size.

Then, if you think about popular overall personal portfolio investment strategy, then you shouldn't have more than 2-3% in any one investment (ie. single stock) to mitigate risk. So is $250K (or whatever amount you are thinking about investing in total) only 2-3% of your overall personal holdings or less?

Remember, betting it all on angel investing is a dumb dumb dumb move.

Are You A Risk Taker?

In order to angel invest, you need to be comfortable with deploying huge sums of cash. You need to be able to do this decisively and without regret or anxiety.

If you are a conservative person, angel investing is not for you.

If you have anxiety about throwing large sums of money out there, this is not for you.

If you can't let go of your money emotionally, this is definitely not for you. You'll drive everyone crazy because you'll be so worried about losing your money and it WILL NOT BE A GOOD THING. Please PLEASE...just do us all a favor and don't angel invest.

Just Because You Like To Gamble, Doesn't Mean You Should Angel Invest

Angel investing is a lot like going to Vegas and gambling except for one important point. In Vegas gambling, the money is gone instantly; you have no recourse but to let go of the money at the moment it's gone. In angel investing, your money isn't instantly gone; if anything it can seem to drag out the loss process for an incredibly long and painful time.

Can you deal with that?

Do You Deal Well with Chaos and Uncertainty?

You might be a risk taker, but if you lose your head during times of great chaos or uncertainty, this is not good. Every startup goes through periods of high stress and low periods. As an investor, you'll probably be dragged along with those sentiments. I've lost my head once and blew up with entrepreneurs once, and learned my lesson that it just isn't productive. You gotta keep a cool head so that you can think clearly and strategize correctly.

Are You Disciplined?

Can you develop a plan and stick to it? Or are you tempted to toss your plan to the wind when something comes along so juicy you can't pass it up, even if it violates your plan?

I have found that sticking to your plan is crucial. It keeps you honest and focused. It also keeps you out of trouble. There is nothing wrong with altering your plan; that's not what I'm saying here. But once you figure out what is right for you, don't mess with it or else you'll get yourself in trouble.

Can You Exercise Tough Love?

As a parent, I often think about tough love with respect to my kid. The same applies to startups and entrepreneurs. When things are going south, somebody has to step up and say that you are heading south and something needs to be done. This can mean things like saying to the CEO that he needs to go, or closing down a startup because it's going nowhere. Anyone can say positive things during good times, but can you tell someone that something is really going bad and that they need to change/stop/leave?

Some of the hardest conversations I've had occurred beginning last year, when I began having talks about cutting burn due to money running out, and the lack of possibility of further funding. With the economy the way it is, I fully expect to see more tough conversations coming up.

An effective angel investor needs to be able to exercise tough love.

Are You Good at Saying NO?

Some people have this issue where they just can't bring themselves to say "NO". It's painful, it risks dealing with negativity coming from the other party, it's uncomfortable as you worry about hurting another person. It also feels bad being negative.

In angel investing, you MUST absolutely have the ability to say NO decisively and stick to it. Clarity is critical and wishy washiness sucks for everyone involved. If a deal is wrong for you, you just need to be able to say NO no matter how much an entrepreneur is begging, making you feel guilty or inadequate. Remember it's their job to sell you on investing in their company. Can you not fall for that and just say NO when you're supposed to?

Do You Have Great Intuition?

I run with intuition a lot. I listen to my gut and if something doesn't feel right, I just don't invest. I don't care what it is. If my gut just doesn't feel the least bit good about a deal, I just say NO. Intuition detects those things that are immediately obvious or things that are hidden. What is it about this deal that sets off the butterflies in my gut?

Intuition is that primal survival instinct that our ancestors and apes gave to us, but civilization just destroyed. We all know people with zip intuition; you know, the ones with seemingly no common sense whatsoever or always getting in trouble? Are you one of those people?

If you have a highly developed intuition, it will pay you in spades with angel investing.

Do You Have Something to Offer Startups?

I'm fond of talking about angel investing as a probability game. You always want to do a whole bunch of things that maximizes the chance that a given startup will succeed and return your investment with profit.

One of those is your money. That's easy.

The other is how you yourself can help. How can you help a startup you're investing in? Can you lend your experience to the entrepreneur? Your business contacts? Your ideas and creativity? Did you specialize in a particular area that you can teach? What else?

If you don't have anything to offer, then you should consider not angel investing, or at least not in the industry in which you have no experience to offer. Remember that you want to increase the chance of your investment's success always; why invest in something that has a lower chance of success? Why do people learn how to count cards to play blackjack, or at least learn blackjack strategy?

Are You Willing to Learn?

You should not be arrogant in thinking you know everything. I thought that by coming from Yahoo!, I could pick successful startups. And I was wrong. There will be a lot to learn, lot that you will not expect, skills that you will realize you do not have. To go into angel investing thinking that you know everything is only going to cloud your decision process. This is bad.

Following on the previous comment, you should be open to learning. If you are not receptive to finding out that others know more than you and learning from them, this is a big problem. You're going to think that with all your previous experience that you're going to be successful, and I guarantee you that you will miss the important finer points that will throw the odds in your favor and not against you.

Regarding Picking Companies

You have to be good at spotting opportunities. I have already said I have fooled myself in the beginning in thinking I was good at this, but then discovered there was much to learn beyond just the idea. Let's just say you have to be willing to learn and deploy intuition and objective measures for picking entrepreneurs and their ideas in order to be good enough at picking companies that you're not throwing money away.

Someday I may write more about what I've learned in picking companies. It's a tough subject with many moving parts. Suffice to say that if you somehow are good at this before you start, then it's a great quality to have. But if you don't have this quality or are unsure, then let's hope you learn because if you can't ever pick great startups, then you're toast no matter what. Go to Vegas and hang out with hot chicks at the $1000 Blackjack tables instead. At least you can hang with the hot chicks while throwing your money away.

Do You Have These Important Other External Factors?

Over these last 2+ years, I have found these external factors to increase the probability of success as an angel investor:

1. Your business contacts include those at companies which can result in strategically important partnerships or acquisitions.

Right now, one of the biggest problems that early stage internet startups face is access to customers, whether they are consumers or other businesses. If you know someone who can create a distribution deal for your startup, that would accelerate the growth of the startup, potentially past competitors who don't have those contacts.

Also, providing more opportunities for acquisitions is also strategically important. This can be as simple as just providing an exit for investors, but in times of economic crisis, it can become a survival lifeline for a business who is running out of money and options. Casting the net as wide as possible can only increase chances for a startup to be acquired.

2. You know and are trusted by other investors, either angels or venture funds, and can invest alongside others who will be helpful and advantageous to a startup.

Again, it's a probability increasing thing. The more helpful people involved, the better the chance of a great outcome. Thus, having experienced investor friends who will allow you to get into the deal is a very positive thing. If you're investing alongside not so helpful or experienced people, it just reduces the chance of success especially if you're in a tough situation, like running out of money and are looking for further investment or facing hostile competition or in need of strategic partnerships.

3. You have access to great dealflow.

This is always critical. If you don't have access to great deals, then why invest in only crappy deals? If you live in the middle of Montana and all the internet deal flow exists in Silicon Valley, how are you going to get included in those deals and/or pitched? There are probably a myriad of ways to access great deals: location, relationships, going to conferences and startup/entrepreneur gatherings - probably worthy of an entire post in itself. But this is a critical part of being a successful angel investor.

Last Important Attribute: LUCK

Are you lucky? Do good things fall in your lap out of the blue? Does opportunity knock for you more often than for other people?

As in all forms of gambling, being lucky gives you an edge over everybody and everything else.

If you are UNLUCKY, angel investing is DEFINITELY not for you.

Over the last 2+ years in angel investing, I learned a lot about myself while doing this. I also learned a lot from interacting with others and learning from them. Exhibiting these intrinsic qualities will enable you figure out if this occupation is right for you, and whether or not you'll be successful in it.

Endnote: Did I miss any essential qualities?

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This page is an archive of entries from April 2009 listed from newest to oldest.

March 2009 is the previous archive.

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