Angel financing

In a few months Lijit Networks will be two years old. We started the company in a fairly common way, finding employees that wanted that “ground zero” experience, having the seed of a good idea, and finding Angel Investors that would invest and keep the idea alive long enough to germinate. It wasn’t easy but we got it done. A question I get a lot from new entrepreneurs is “how do you find Angel Investors?”

Many young startup entrepreneurs tend to look at Angel Investors as a group of people with more money than sense (which sometimes is true) but generally not. They give no thought to the motivations of their Angels, what their Angels should get from the relationship, or simply why the Angel should be interested in investing. Like anything, understanding your audience is half the battle. Don’t trivialize your Angels Investment by rationalizing the money isn’t important to them; I find that $25K is important to everyone.

I have been on both sides of the Angel Investment table. Lijit was Angel funded for the first year of its life. We raised approximately $900K from a combination of friends, family and seed professional investors. On the flip side I have made several Angel investments in other local companies – with varying success. Based on this sample set plus other random data I have collected along the way, I have established a basic way to look at Angel Financing.

Types of Angel Investors:

The Family Investor: The Family Investor is likely not really a classic Angel Investor at all but rather a supportive family member that “knows you”. Their motivation is likely out of support (sometimes guilt), but their basic investment thesis is they trust you. For me these are the worst type of investor because you likely have intimate knowledge of their financial situation and whether or not they ’should’ be investing. Likely, they have no inherent feel if your idea is good or not, but may have changed your diaper at one time or another and have overcome that experience to hand you a check for $25K or $50K. Personally, I like this category of investor the least because the investment is totally emotional and personal – and that sucks in business. But based on the financial situation of the individuals involved and the relationships this can work ok if everyone comes into the situation with their eyes open, but go out of your way to make sure.

The Relationship Investor: The Relationship Investor is probably one or more co-workers from a previous gig or business friends you have known for a while. They may or may not understand what your new company is doing but they have had a track record working with you. They want to be supportive, but are looking for a return. You won’t lose them as friends if things go bad, but the investment for them is likely not ‘trivial’. In my experience these are good Angels to have, again as long as their eyes are open going in. These people can also be wildly supportive of you in terms of finding employees and other resources.

The Idea Investor: The Idea Investor is probably very familiar with the space your company is targeting. These are in some ways the very best types of Angels because to some degree they validate your idea. There investment is based on the Idea and there is little emotion around the table (always good). If you can get them onboard they can open doors into partner relationships and just generally good advice. You will spend most of your time convincing the Idea Investor that you and team are the right people to attack this problem (as they likely don’t have a strong relationship with you or the team). Often an influential Idea Investor makes a good early board member for the company.

The Once Removed Investor: The Once Removed Investor is likely connected through a personal or professional relationship with either the Relationship Investor or the Idea Investor. They likely don’t know you, and they likely don’t have a clue if your idea is good or bad but they have translated the trust in the investment to the person they know. This is a great way to get additional Angel Investors onboard, but without a solid Relationship Investor or Idea Investor it just isn’t going to happen.

I personally have never seen an Angel Financing come together without some mix of the first three investor types plus a few Once Removed Investors. Be warned that the Once Removed category of investors will also supply the softest money in the upcoming financing. Simply put - as you verify amounts before close, the Once Removed guys are the ones that tend to “go away” or “get smaller” as the deal progresses. A friend of mine that has successfully financed several companies gave me the rule of thumb that most investors will end up being about half of what they initially committed to. This is definitely true of Once Removed Investors; I once had a $400K guy turn into $50K guy, and $50K was like pulling teeth.

Finally, there is a concept I refer to tongue-in-cheek as the Arc Angel. An Arc Angel is a Relationship Investor or Idea Investor that has a track record of success making other Angels (and perhaps non Angels) money. These people are valuable as they can be very influential attracting quality Once Removed Investors. If you can find this person and get them excited about your deal, do it.

The bottom line on Angels, spend your time looking for solid Relationship Investors or Idea Investors, they are the ones that will get you over the hump. Bring a few Family Investors along for the ride if they won’t get sick on the Rollercoaster and hope that you can mix in a good set of Once Removed Investors.

Size of Investment

Next, you have to consider the size of the investment. Money never goes as far as you think it will. My experience is you need to raise between $500K and a $1M to do almost anything. Using Angel Investors to achieve this goal you are likely looking at investments all over the board but usually in the $25K to $100K range. You may have a few smaller and a few larger but in my mind you have to target having no more than 10 to 15 total investors in an Angel round. It’s just too hard to herd the cats when the group gets larger than this.

Pre-Money Valuation

A friend of mine with much more experience then myself told me, Angels should get a good deal. They are putting money in at a time when presumably no one else will and they are taking a huge risk. I can’t tell you how many people have said, “Yeah, but its only $25K and they have lots of money”. That’s total bullshit; show me someone who lights $25K on fire for no reason.

Having been on both sides of these kinds of deals, I totally agree that Angel Investing is very high risk and the road ahead as an Angel is fraught with investment disaster. Lots of wonky things can happen to the Angels when VC’s come into the company including investment preferences that take away the Angel Chocolaty goodness. I have also, unbelievably, had meetings with entrepreneurs where they are indignant I won’t accept their pre-money valuation on their imaginary business. I always tell them the same thing, if my money is so unimportant, do it with yours. If you feel compelled to twist the valuation screws do it in the A round with the professional investors.

Investment Mechanism

There was a period of time where nearly every startup was doing convertible financings. This is where as an Angel you invest as if the investment is a debt type financing but can convert to an equity investment based on some outcome or the will of one party or the other. I tend to think these deals kind of suck. They are usually setup to attract money fast, and often in the case of the entrepreneur are empowering some kind of fantasy that the investment could be paid off based on success of the company and he won’t need to give any equity away. As an investor that’s the last thing I want because that just turns my investment into a very high risk bank account. The only time I saw this work well was a company that had plenty of investors around the table and incented them to invest early to get the company jump started faster. Early investors got some warrants to make it worth their while to have their money show up to the party sooner (and deal with the risk of being the first money in). Just skip this stuff, get all your Angels aligned, do one close, and make it a pure equity round. If you aren’t ready to sell equity in your idea, finance it yourself.

Liquidity

With the exception of possible investors in the Family category, Angels are not in it to finance your dream indefinably. You would not think it to be the case, but I have had several conversations with people approaching me for Angel investments who simply could not articulate how I would ever get any money back. They were so focused on getting money from people they forgot ‘they are an investment’, and investments have terms. Almost without exception, I don’t want to own your dream, I want to make money and have a little fun along the way. If you never sell the company, I never realize a gain.

Conclusion

There are probably 5 more posts I can do on this subject but my goal was simply to put together a primer on this subject. So many people approach me not understanding the dynamics of early stage financing. Brad Feld has written good stuff in this area on his blog as well as some quality stuff on AskTheVC. Use these resources to understand the numbers, but don’t forget to understand the motivations.

What we learned by moving to Boulder

In a follow up to our Who We Are post, Ryan and I thought we would compare VC life in Boulder, CO to that of the Silicon Valley. In some ways it’s remarkably similar and in some ways wonderfully different.

For those of you who don’t know, Ryan and I met in 2000 while at the California offices of Mobius Venture Capital, became quick friends and even started a band or two. (Shameless Plug Alert: Our band Soul Patch has recently released a new album. Check out the web site and buy on CDBaby, iTunes and Amazon. Become a fan on Facebook!). When the concept of the Foundry Group was born, one thing that the five of us agreed on was the need for one (and only one) office.

It didn’t take us long to decide that both the Boulder and Foundry Group opportunities were what we wanted to pursue with our careers, so, after a combined 27 years in Northern California, we sold our homes in the Bay Area and moved to Boulder in mid 2006. We’ve now been here almost 2 years. What have we learned?

Boulder is an entrepreneurially vibrant community. We were both surprised and encouraged by the sheer amount of startup activity there is in Boulder. It’s not just a by-product of having several good universities nearby; rather it’s really part of the culture and fabric of the community. I’d compare this to Ann Arbor, MI, where I went to school. Many people compare Ann Arbor to Boulder (without the mountains). While I see plenty of similarities, Ann Arbor is missing the ingrained culture of entrepreneurship (and associated risk profile) although it may have similar engineering and management talent.

Boulder is a supportive community. There really is a sense of community here. While there is a ton of activity, I don’t know if we’ve ever been to place that is as supportive in each other’s efforts. Instead of competition, there is collaboration. Whether it’s the Boulder NewTech Meetup, the Boulder OpenCoffee Club, Boulder Software Club, or TechStars, there is a general sense of community and responsibility to help the entrepreneurial community grow. I can’t say that I ever felt that sense of responsibility and “giving back” in the Silicon Valley that I feel here.

Boulder makes nationwide travel much easier. As national investors, it’s much easier for us to travel anywhere in the US from a central location like Denver. We’ve even been able to take day trips to New York, an impossible feat from the Bay Area, at least without a private jet. While an East Coast day trip is not the most fun one can have, our families appreciate us being home at night. And getting back and forth to Los Angeles and San Francisco, where we travel most frequently, is a relatively painless and efficient experience.

Speaking of travel, both Ryan and I (coincidentally) live on the same block in a neighborhood a few blocks away from our office. Our “commute” to the office is infinitely easier than our prior commutes in the Bay Area. The time saved can be spent on work or play, but either way, it’s not spent in the car. (For those voyeurs among you, you can check out our neighborhood by going to Google Maps and clicking “Street View”.

Being in Boulder helps focus our West Coast activities. There is no doubt that the volume of startup activity in the Bay Area dwarfs that of Boulder, and we have often been asked if we are concerned that we are missing out on opportunities by not having an office in the Valley. On the contrary, we consider being outside of the (sometimes provincial) echo-chamber of Silicon Valley to be genuinely useful. After experiencing life as VCs in the Valley for several years, we experienced a very real “time tax”, which resulted from taking meetings with entrepreneurs and executives we knew we were unlikely to invest in, but we felt were ultimately necessary to participate in in order to maintain our relationships with friends and colleagues in the area. Not being in California every day means we can opt out of that process. With our new location in Boulder, we still have our great networks and deal flow in California, but we have removed the Sand Hill Road friction from our day-to-day lives. When we do go to California to look at deals, meet with entrepreneurs or attend board meetings, we are better focused at the matters at hand and tend to have higher quality meetings, since those meetings have passed the “is it worth hopping on an airplane to meet face to face?” test.

Boulder’s culture encourages a healthy work-life balance. Boulder has an incredible amount to offer with easy access to mountains, hiking trails and natural beauty. People actually have time and focus to concentrate on things outside of work. It’s definitely a slightly saner pace. It’s not that people don’t work hard – they do – but there is a certain amount of balance that isn’t completely explainable unless you live here. For us, it’s meant that the hours we do work are more efficient and our brains are sharper.

So is Boulder utopia? No, nothing is. Ryan and I will “forever” tease our partners who told us that winters were mild in Boulder. Upon our arrival, we had the “opportunity” to experience the worst winter “ever” in 2006-2007. We’re also being told this winter is “below average,” which means that we’ve clearly brought bad luck with us. Either that or we were sold a bill of goods. More on that next year, I suppose. Also, we both miss some of the culinary options of the Bay Area, but we’d be in the same situation if we lived anywhere else but New York or Los Angeles (with apologies to Chicago). Finally, we must mention that the Denver Airport has the worst parking facilities in the world. They are regularly full, making for some tense moments pre-departure.

But in general, Boulder is a great place to live, work, play and (in Ryan’s case) raise kids. We’ve embraced our new hometown, and we look forward to continuing our integration into the community, both from professional and personal standpoints.

Filtrbox gets better every week

I have a very patterned daily information consumption routine. The left-most tab in my browser is called “Daily” and contains a set of web sites that I open up each morning and look at as part of my routine. Recently, Filtrbox - one of the TechStars companies - graduated to be part of this tab.

I try virtually every news alerting system that I come across. I have a set of about 100 keywords that I track daily - all of the companies we’ve invested in, a number of people that I follow, and a handful of random things I care about. My current staples are Google Alerts, Yahoo Alerts, and Technorati. I can only seem to get Google and Yahoo via email, so they show up in my inbox and get moved to my “Daily” email folder (which I read - er - daily.) Technorati comes via RSS so I read it each morning in FeedDemon.

The vision for Filtrbox when they started at TechStars last summer was to create an integrated single dashboard of all this keyword alert information. The tagline “more knowledge, less noise” says it all. My partner Seth Levine and I totally resonated with this - Seth has a great post about Filtrbox up titled Know what you don’t know which addresses how he thinks about the problem and how Filtrbox solves it for him.

For a while I found the Filtrbox data interesting, but not really that additive. In addition, the UI was “ok” but there where lots of little things that slowed me down. About three months ago I noticed I was finding new information from it that wasn’t appearing in my other keyword searches and that it was streamlining this information in ways that I hadn’t expected, such as eliminating duplicates (e.g. the same alert coming from Google, Yahoo, and Technorati - which happens many times each day - only appeared one in Filtrbox) and allowing me to filter based on thresholds for each keyword. In addition, as the UI evolved, I found I was spending less time scanning the alerts and more time clicking through onto the interesting ones.

I hit a tipping point about a month ago where Filtrbox became more useful to me than Google+Yahoo+Technorati. I haven’t turned off the other alerts yet, but I find that I’m not getting much additional info from them anymore now that I use Filtrbox as my top level sort.

Filtrbox is still in private beta, but if you are interested in playing around with it you can get a golden ticket by clicking on the special magic Brad Feld Filtrbox link. I’m really proud of Ari Newman, Tom Chikoore, and team. They have reached the point where their service is very valuable to me and gets noticeably better every single week.

Jobs galore at TechStars companies

Wanna have some fun? Many TechStars 2007 companies are still hiring.

Brightkite (location based social networking) which recently raised a little over $1M in funding is hiring Rails developers and Flash/Flex developers. Their office is in downtown Denver.

J-Squared Media (social communication services) in Philadelphia is hiring a UI designer.

Filtrbox (content monitoring service) is looking for a Java developer and is located in Boulder.

Intense Debate (blog/media comment replacement) is looking for a technology evangelist, a systems administrator, and a Javascript & PHP developer. Intense Debate is located in Boulder.

Community Direction

First, I’d like to say thank you to those of you that have made this community so strong. It is an honor to join the team.

TechStars has a special place in my heart. I was lucky enough to sit in on last year’s session, observe how the program worked and what made the teams tick. I am excited to help out the teams, the program, and the greater community.

Though TechStars is primarily about fostering the success of the 10 companies, in the end, it is all about community. A large part of my participation here is to build upon that by connecting with these groups:

Local Community

Boulder is an amazing place; in all my travels, I would argue that it is the best place to start a startup. I love it here, and the local community is both helpful and humble. One of the challenges I face is ‘how I can help the founders integrate into the community?’

Founder Community

How do we make the program better for the founders? What additions can be made to last year’s program?

Startup Community

Although there are 10 teams every summer, thousands watch their progress. I think it would be great to create easy ways for the founders to interact with the community via blogging, podcasting, vlogging, live streaming and anything else that would be contribute to interaction between the founders and the greater community.

I am very excited for this chance to work with an incredibly driven, bright and talented group of startups this summer. To start it off right, here is a podcast with David Cohen and I talking about choosing the companies for TechStars.