Recently in Angel Investing Category
- We've made eight initial investments and one follow-on.
- Two exited (Notehall and Locately), one died (Wakemate), and the rest are looking good.
- I syndicated (helped them put together the round) in five: Notehall, MyZamana, Locately, Zippykid, and Instinct.
- I took a board seat in three: Notehall, MyZamana, and Locately; I took an active advising role in Instinct.
- Five of these companies are consumer; two are enterprise; Zippykid is in-between.

- How did you (founders) come to be entrepreneurs?
- What led you to this market/idea in particular (and what markets/ideas did you discard along the way)?
- What is your path to victory?
- What are your exit expectations?

I believe that ambitious startup ideas have similar success probabilities to their less ambitious counterparts, if not higher success rates. No, I don't have any real evidence. Call it a highly educated guess.
I've written before about how the very first email to an angel investor really matters, or at least to this angel investor. It's very easy to get thrown in a bucket of wannabes or bad first-timers. Here are a few of those red flags from my perspective.
- Is this person a crackpot?
- Is this person a wannabe?
- Is this vision fundable?
- Is this vision fundable by me?
- Is this vision plausible?
- Is this vision probable?
- Are these people capable of executing this vision?
B. Is this a side project?
C. Is this (for lack of a better phrase) a lifestyle business?
D. How does this get to 1Min revenue?
F. Are they thinking big enough?

Your story either clicks with an investor or doesn't, and in my (albeit limited) experience that clicking either happens really fast or it will take too long to matter.An investor's instinct around something as fundamental as whether your business can reach the scale needed for venture capital returns is one that won't be found scouring the latest market forecasts from Forester or Goldman Sachs. It won't be found in endless meetings and it won't be found in detailed financial forecasts or market sizing exercises.
It will be found in the connection an investor makes to you, your product and your vision. Either they will believe it or they won't. If they do, they'll want to invest. If they don't, they'll simply keep wrestling with the question of "how big can this get" in an unresolvable circle of swirling doubt. All of the Excel wizardry in the world won't resolve it.
This is why that first impression, including your email, intro path and pitch deck is so important. It's your chance to make that click happen, or blow it. It's hard to recover from the wrong framing.
So with that in mind, I'm changing my pitch deck advice for seed rounds to be a bit higher level. Yes, you should stick to six slides blah blah blah, but you should be thinking more about what story you are telling to potential investors. And if you're really good, what story you are telling to a particular investor.
For me at least, I think you want to nail four things in your story:
- What will it take to get this business to 1-3M revenue? This part of the story shows you've thought about how this could be possible, how many customers you'd need, how much they might pay/convert/draw in/whatever, etc. None of it needs to be correct, but it needs to be plausible. If you already have some traction, perfect -- use that as a lead-in.
- What are the possible medium and longer-term exit opportunities? This part of the story shows you understand your space, how you align strategically with it, and how big you're thinking. Again, be plausible. Anything else is a red flag.
- What about your team says you can execute on this? This part of the story shows you personally, and I'd get really personal.
- Why are you raising money? Every story needs an ending, and this is usually it. We're trying to hit this milestone by doing a, b and c. That milestone is important because of x, y and z.
I hope it goes without saying that when you have that meeting you should be telling that story. I wouldn't walk through the presentation at all unless someone asks. Instead, just start story telling.
Update: I have some evolved advice now.::
- US companies. You do not need to be associated with Philly. In fact, last time we had companies from Austin, NYC, Minneapolis and Chicago, in addition to Philly.
- Working demo, preferably already launched with some engaged users. The event format is a five min demo followed by a five min Q/A followed by networking. It's not a traditional pitch event with slides, so a working demo is essential.
- Products matching our investor preferences. Our goal is to get you funded, and to do that you can't look too different than things our angel investors generally invest in. This generally means software of some form.
- Terms matching our investor preferences. Same as above, our angels are looking for good deals. This generally means reasonable valuations and seed rounds (essentially first money in).
- We're accepting applications for OAF Philly II through Fri August 26, 2011.
- Antonio and I will then go through and select the companies that fit the above criteria.
- We will then try to hold Skype demo sessions with all those companies. Last time that was about 25 startups. We may involve some other angels in this process.
- We will then extend invitations until the six slots are filled. We're aiming to do that by Sep 12th.
- Yahoo IPO, Apr 1996. I was ready to put all my money into this. Granted, I was 16, so not a lot of money, maybe ~7K. I had been on the Internet pre-Web and really thought they were onto something. I got talked out of it and didn't do it. Of course, I could have been wrong and lost it at all too!
- Posterous, 2001-2003. I had a thesis (which still seems true) that email is perhaps the easiest path to virality and mainstream adoption of Web services. I had three different projects around that time where you could send an email to an address, and then the service would auto-create an account and auto-publish content. I wasn't thinking big enough though (mine were too nichey) and I didn't have enough staying power. I did ride the same email thesis through my last successful company, but it had very little to do with publishing content.
- Bitcoin, 2010. I was following this closely and ready to pull the trigger here, but just didn't because I thought it would take a lot of time and I'm so busy with DuckDuckGo and other things. I didn't think hard enough about it to realize I should have just bought coins instead of doing calculations around mining for them.
- Angel Investing, ongoing. As like probably most investors, I've already passed on several things that are doing awesome. Now they stare me down every day!
- Fancy Hands (NYC) - personal assistants for everyone.
- RezScore (Philly) - resume analytics.
- Row27 (Minneapolis) - official mobile apps for sports teams.
- SpeakerWiki (Austin) - marketplace for speakers.
- Sqoot (Chicago) - adsense for deals.
- Contently (Philly/NYC) - marketplace for high quality content.
- Hadn't launched.
- No engaged uses after launch.
- Too high valuation.
- No software component.
- Too far along in fundraising process.
- Non-US.
For this investment thesis to work, it seems there has to end up being a long tail of Internet startup acquirers. That is, the tech giants (Google, Microsoft, etc.) aren't going to acquire enough companies to make the numbers work. The concept of acquiring Internet startups must extend to M&A departments outside the tech sector.
The Open Angel Forum (OAF) is dedicated to providing entrepreneurs with access to the angel investor community based solely on merit (and without fees). Additionally, we strive to build collaboration between angel investors and to inspire high-net worth individuals to become angels.

- Raising a seed round. I led the last two deals I've done in the sense that I put together the syndicate of the right angel investors, negotiated the terms for them, and made sure it all closed quickly, fairly and without incident. For both deals we used the open source Series Seed docs, which kept things extremely low cost (actually zero legal on our end). I'd basically like to continue filling this role.
From the company perspective, I think this is quite appealing, especially if you are not a super hot company and not in the valley, which is the space in which I operate. One minor quibble I'd make with Paul Graham in his recent investing essays is that for a lot of startups it takes a lot longer than a few days or weeks to raise a seed round. The median is much longer because most companies fail to raise anything, and the mode I see seems to be somewhere at 4-6 months. - Day to day business advice, i.e. been there, done that. I've been doing this startup stuff for a while now, pretty much all by myself or with one other person. So I've done most startup things, i.e. from incorporation papers all the way to an exit and everything in between. Moreover, I want to be closely involved. For most of the companies I'm involved with, we try to have frequent Skype chats (weekly to every few weeks) to discuss whatever is in front of them.
- Technical stuff. I'm a hacker that has built a lot of sites and scaled some to a decent degree--certainly not facebook/twitter scale or anything, but on the order of 20 million users. I've pitched in when companies have been in a bind, e.g. debugging downtime, writing a script, solving email spam problems, etc. Of course, the closer you are to my core tech competencies (databases, data mining, Web crawling, uptime, etc.) and particular technologies I usually use (nginx, postgresql, Perl, JavaScript, etc.) the more I can help.
- Domain Knowledge. If you're trying to do something very specific that I've already done or am researching, like engineer a viral loop using email, spider and organize a lot of structured content, SEO, etc., I can be incredibly useful.
- Raising a Series A round. Truth be told, I'm looking to invest in things that if all goes decently well, a Series A round may not be strictly needed because the company would be profitable. So if it is raised, it should be easier to do so because of the traction they would have. Nevertheless, things don't always go as planned, and so it is important that I cultivate relationships with the right VCs who could help fund portfolio companies. I've been actively working on that, especially locally. For example, I'm bringing Open Angel Forum to Philly next year and have been meeting essentially everyone in the city involved in funding Internet startups.
- Introductions. You can see from my LinkedIn who I'm connected to. Again, I'm actively expanding my network all the time, e.g. through my Traction Book interviews. It's definitely improving, but there are certainly many investors with more substantial networks. A lot of this related back to amount of deals. Frankly, I haven't done that many, but this should of course improve over time.
- Hiring. This seems to be a major problem for startups. I actually started a local hackathon group three years ago (200+ strong now) to help make connections between people interested in startups, hiring being one type of connection. And I have introduced people that have resulted in hiring, but the problem is still a big one, especially if I continue to invest nationally. That is, things I do in Philly, like copy good programs from other cities, won't help a company in Boston (unless they don't mind a virtual hire). I think what we really need is an organized startup job board (yes, I know there have been some), that is promoted by major startups/startup hang outs and has a barrier to entry to applicants, like HN karma or something. This is half baked atm, but maybe someone will run with it.
- Get you on Techcrunch. Or PR in general for that matter. Honestly, I haven't really figured this piece out yet, though I have been doing interviews on it to learn more. Duck Duck Go has had a lot of good press, but it has pretty much been unsolicited or based on warm intros. I would like to say I'm working on meeting the right people in the press, but I'm not. I just don't have enough time right now, and I don't like to travel.
- Get you traction. Yes, I am slowly working on a book on getting traction. That means I can tell you lots of strategies that you should check out and even tactics within them. But that doesn't mean attaching me to your startup will actually get you traction. In fact, I want to invest in things that have a spark of traction already.
- Help much with managing employees. I really haven't managed many people, so my experience is very limited here. But I do try to include people in seed round syndicates with varying (and relevant) experience so there are investors to go to for this kind of advice.
- Help with big company politics, sales cycles, etc. Same story.


- You get a term sheet, and like some of what you see, e.g. price.
- For lots of possible reasons (don't want it to go away, pressure, excitement, lack of understanding, etc.) you sign the term sheet to get to the next stage.
- You then get the draft deal docs based on the term sheet.
- You start reading through them and consult with your lawyer and see a lot of scary stuff.
- Some of that stuff was actually in the original term sheet at a high level.
- You start pushing back on these terms that you don't like.
- You'll usually end up worse off than if you negotiated the term sheet properly. The problem is you'll get serious push back of the form "you already agreed to that in term sheet." Yes, things are probably still negotiable, but you've lost a lot of your positioning, and frankly, they make a good point. So you'll probably be more likely to get stuck with things you don't like.
- You're significantly lowering the probability of closing. Each term in a term sheet gives and takes off of others. So when you try to clean it up after the fact, you're really asking the other side to go back to the term sheet stage and put everything else back on the table. Again, this is doable, but it puts the deal in reverse, and that is never good. You want to maintain momentum.
