Recently in Angel Investing Category

Traction trumps everything

 
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If you ask an angel investor what they look for in a company, they'll usually rattle off a list of things that describe the ideal angel investment: huge market, great team, superior product, sustainable competitive advantage, etc. Trouble is, even if your startup has those things (and most don't), you still have to convince each investor.

Good thing there is a shortcut: traction. If you show investors some traction, the rest of the conversation becomes a lot easier. They'll generally be willing to overlook some of your deficiencies, probably even more than they should. 

Traction is real customers. If you charge for your product, it's real paying customers. If your product is free, it's a real user base. In other words, traction is a signal that your team can produce real results in a real market.

You don't need much traction to entice investors. In fact, people like myself prefer just a little because when you have a lot your valuation will probably be too high. The ideal scenario from my perspective is you already got a bit of traction, and you know how to get more with some investment. 

You played around with various traction verticals and you identified a few promising ones that brought in your early customers. Now you just need $x to experiment more heavily with those channels. That's a compelling story.

I should also point out that once you have traction, you may not need investors at all. 

How-to learn about angel/vc term sheets

 
I think every startup entrepreneur (and angel investor) should have a good understanding of financing term sheets. Yes, even bootstrappers. I haven't raised any money for my companies that required a term sheet (just friends & family money in my first company), and yet I still think it is important for a number of reasons.

First, most companies will raise money at some point, and you don't want to be learning everything when you need to raise money because it will be distracting and you'll make mistakes that in hindsight seem stupid. Second, you never know exactly when you're going to be in a financing situation. Third, a lot of the same principles carry over into M&A term sheets, and even if you don't raise money I hope you may be involved in an acquisition at some point. And perhaps most importantly, fourth, it doesn't take very long.

I've written up the following directions to help you get there efficiently. Don't do it all in one sitting because you want your mind to digest the concepts over time. I suggest doing it over the course one week, setting aside a half an hour each day to go through this stuff.

Fortunately there are now a lot of great free, public resources to learn about financing term sheets. I would start by familiarizing yourself with some actual term sheets. For seed rounds, check out these (reading them slowly from top to bottom):
Now that you've seen what a term sheet looks like, go through each term and read the associated post in Brad Feld's Term Sheet series, a series of blog post where he explains each term. Some of these terms he covers are not in those docs, because they are more for venture rounds. You can skip those for now.

Once you feel you understand what the terms in the seed docs mean, read this Startup Company Lawyer post explaining how they differ from each other. Once you understand that, then you're ready to get a bit more complicated and look at more complete venture term sheets:
Launch the Term Sheet Generator, and open the NVCA doc. Now go through each term and go to the relevant section in the generator by accessing the select box at the top. Some of the terms will be familiar from before. The generator offers a lot of additional background/insight from the context of building a term sheet. Look for the links on the right entitled 'Click here to hide/show explanatory ntoes.' Also look for the market data links, e.g. liquidation preference.  And of course refer back to Brad's term sheet series for any posts you skipped before.

By now you should be familiar with pretty much every term and its place in the term sheet, and you're ready to digest some more advanced material. First check out this Startup Company Lawyer post on how the YC seed docs differ from traditional Series A docs and this Series Seed post on the same topic. Then check out these applicable Venture Hacks posts: Term Sheet Hacks, Option Pool Shuffle, Term sheet tune-up, & Terms that hurt. Finally, here are ome other posts that I think round out term sheet knowledge: The Challenge of The Ideal First Round Term Sheet (Brad Feld), Ideal first round funding terms & Don't shop your term sheet (Chris Dixon).

If you'd really like a book, I'd suggest the brief Term Sheets & Valuations, although I want to underscore that I don't think it is necessary. I purchased this book a number of years ago before I knew about any of the above (and most of it existed!). I found it useful then to get an intro into this stuff, and I just took it out and skimmed it and think it is still useful.

hacker angels

 
hacker angels is a new group of hackers who are also angel investors. The group currently consists of myself, Joshua Schachter, Jeff MillerRoy Rodenstein and Jim Young

You can follow us all on twitter via the new hacker-angels list. You can also email us at ha@hackerangels.com.

We are all generally looking to invest in other hacker entrepreneurs like ourselves. We are also looking for other hacker angels to join us.

I believe that there are many good hacker entrepreneurs who are not getting the funding or advice they need to get traction for their startups. I also believe hackers relate well with other hackers, which is why I think the concept of hacker angels is so compelling.

We're currently just an informal group that I'm sure will evolve as we get interaction and new members. I look forward to hearing from you!

What I learned at Angel Boot Camp and Techstars demo night

 
I just got back from the Techstars Boston demo night. Last night I went to Angel Boot Camp. I live outside of Philly, but made the trek up to Boston for both events. Here's what I learned.

  • Lots of companies won't need VC. Chris Dixon recently wrote about how old VC firms should get ready to get disrupted. That was painfully obvious at both these events. 

    At Techstars, every single company was raising a small angel round. Not one company pitched for a Series A and yet a decent portion of the room seemed like VCs. This could have been due to a lot of reasons (advice, selection by TS, etc.), but bottom-line everyone felt it was in the interest of the companies to pitch this way.

    Technology and customer acquisition are now cheap. $200K can get you a lot of validation. But interestingly, because validation is cheap, if it works, the companies may not need to raise more because they'll be instantly profitable. And if they do need to raise more, the valuations will be good.

    I felt validated in my strategy to look for companies that, if everything goes as planned, may not need VC money at all.
  • I need to do more deals. I was already planning on doing more deals, but this need was reinforced. There are two main reasons. First, the simulations show you need to do about twenty deals to guarantee some return given a reasonable distribution of hits. Second, deals create deal flow, and deal flow creates returns. By doing deals your network grows, and in turn, your deal flow.

  • I should invest in hackers. I'm a hacker and I believe I understand the hacker mentality pretty well. I want to invest in people I trust, understand, and most importantly that I personally want to spend a lot of time working with. Basically, I want to invest in people like me :). It's become clear that doing so will both increase returns and increase satisfaction in my angel investing.

  • I need to get plugged in more to the community. I suck at "networking." Like most people, I'm known in some circles, and completely unknown in others. I'd like to be more known in the angel investing community, and should find ways to make that happen.

  • Philly needs work. Boston kept comparing itself to Silicon Valley. Philly is well behind Boston. It's clear that some local super angels would help. Boston seems to have a few.
Thank you to Roy Rodenstein for pushing me over the edge to come up to Boston and attend these events.

My angel investing strategy vs Joshua Schachter

 
Joshua Schacter has a great AMA thread on HN about angel investing. He shares a lot of interesting info about his strategy, and it's about as diametrically opposite to my strategy as you can get.

I think his strategy is essentially the Ron Conway strategy, and at his rate ("34-ish investments" in 1-2yr?), he'll be the next Ron Conway in short order. 

The strategy is pretty simple. 
  • Get access to all major deals (super high deal flow);
  • Invest in anything that seems like it may be big (lots of investments);
  • Don't worry much about terms.
For the record, I think this is a great strategy if you can do it, but I can't do it for two reasons. 

First, I don't live in Silicon Valley, which is essential to getting super high deal flow. Most deals are there, and to get access to everything you seem to have to (at least occasionally) have in-person meetings, go to parties/social events, sit on panels, etc. Bottom line, without being there, you won't get into all the deals you need to be in to make this strategy work. And as I additionally hate short trips and airplanes, I'm even less able to compensate for my home in Valley Forge, PA.

Second, I don't have enough money. Even at his small investment size (10-25K), he's still done "34-ish" deals. Quite frankly, until I show some modicum of success, that is too much outlay for me.

As a result, I'm looking for very different investments. Here are some major differences I found intriguing from the thread.


I've done 34-ish investments.

I've done three :). If you're doing the Ron Conway strategy, you're trying to get in relatively early in the next billion dollar company, or at least in ones that will sell for $100M+. That's why terms don't matter that much. When you get 100-1000x time returns, getting access to that big deal is the most important thing.

The problem is, it's really hard to tell which deals are going to be the big ones. And there are only like 15 100M companies founded each year (reference from Marc Andreessen that I can't find right now). When you cut out ones you won't do because of product area (life sciences, clean tech, etc.), the number dwindles to just a few or less.

As a consequence, you have to do a ton of deals each year, just like he's doing. Given that I can't do a ton, I've taken a different approach.

I'm not looking for the billion dollar company, or even the $100M+ exit. I view it as entering a raffle where I can't buy enough tickets to make the odds decent.

Instead, I'm looking for companies that can go big in the $20-50M acquisition range. Sure, if everything went 100% perfect, they could IPO or $100M+ exit, but the more likely "medium-high" scenario (and the one I look to) is a decent sized acquisition.


I can't or won't negotiate terms, lead a round, syndicate a deal, or sit on a board.

I'm on two boards (of my three investments). I led one and half-led another. I'll negotiate terms--you sort of have to if you're leading. Note that I'm also willing to take terms as is if it makes sense; I've done that once already.

This also follows from this standpoint of doing less deals. Less deals means each one counts more, so I'm putting a lot of effort into each deal, both before and after investment.


Use of capital is a typical open question. But no, I do not ask for a budget. They should spend most of it on people and the rest on other constraining resources.

This is an example of effort I spend before deals. I do a lot of due diligence. I do want to know about use of capital, for example, and everything else for that matter. I'm not the guy who is going to write you a check after one conversation, which you should be wary of btw. 


Startups don't generally tell me about their decisions often enough for me to be able to benchmark this, I think.

Post-investment, I'd like to help as much as possible. I don't nag or even am very pro-active since I don't want to bother founders. But I'd love to help move the investment forward, even technically. For example, I've helped with scaling/downtime/dns/email/testing issues in addition to the normal intros/strategy type help.


What portion of your investments are outside of the bay area? None.

I've done one in Philly (though they just moved to SV), one in SV, and one in BOS. Location (as long as it is US) is not that important to me.


Are you doing it for financial reward or for the enjoyment of it? Probably the second, currently. I haven't seen a lot of return in real dollars.

I have enjoyed it so far immensely, though I am definitely in angel investing to make money. As such, I'm looking to get a decent equity % so that when an exit does happen, I can make some return and do more angel investments. As I've tried to articulate above, if you're not expecting a 100M+ exit, then the deal terms matter more.


Valuations are often in the $2mm-$5mm range. Sometimes much higher. Never lower. 

I'm looking for $750K-2.5M. For deals I'm leading, the target is <=$1M. For deals I'm joining, it's above that. So there is a bit of overlap, but not much.

I think that means I'm looking at earlier deals and never "hot" deals. You don't want to go over 20% dilution, so we're talking about a minimum $200K round, and scaling up as the valuation goes up.

7/10 companies coming out of accelerators aren't getting funding. There are a lot of reasons for that, e.g. solo entrepreneurs, ideas that need major pivots, etc.  However, I think there are some great potential companies in there if they had the right mentors.


In my experience, companies raising less than 500k are making a huge mistake ... The point of raising funds is to hire people who can accelerate the growth of the business. $200k gets you a person or two, which doesn't do very much. So you find yourself raising again pretty much immediately. The fundraising process is a colossal waste of your time. An entrepreneur going this route is not making good trade-offs. In my experience, most of these companies fail.

In my opinion/experience, this is not the case if the company is already making revenue (even if just $1K total) and has some good user acquisition ideas. That's really what I'm looking for. And in those cases, I think a $200K round makes perfect sense because the money goes to acquire customers and not to head count. If the process works, then the earnings that ensue can fund head count, if and when needed.


If $200k is good but $500k is not as good, it smells like a lifestyle business. That's not bad, but it's not a good investment for me.

There are two issues here. First, that's why use of capital is so important. If the $200K is for a specific marketing purpose that fuels a viral engine, then it makes perfect sense and is not a lifestyle business. That is, if you have a real customer acquisition channel that you can pour money into, then you shouldn't need more than $200K to test that assumption. Or even less. 

Second, dilution/valuation is directly related to round size. If you're talking really early where I want to be (at lower valuations), round size is essentially capped at 20% dilution.

In any case, I agree that fundraising is a major time sink, but raising a small amount can go really fast if you have a group of co-investors that believe in what you're doing. That's what I'm trying to be part of in Philly.


I expect it will take 5-10 years to get a return in many cases.

I expect a much shorter time horizon, avg 5 years. I think the diff here is related VC exit times

Again, it comes down to strategy. If you're looking to 100M+ exits, you basically need VC. I'd fund a deal that may not need to take VC, ever.

***

Just to show that I'm not a complete contrarian (crazy person?), here are some things he said that I completely agree with.

Communication is key. If you want people to do things, you must communicate in ways that facilitate the action. Make it easier for me as I am bandwidth constrained.

I don't understand b2b and am terrified of it. [bc of] Sales. Seems very hard. Not that that route is bad but I understand b2c better.

I really want to see a working prototype first. Rarely do i invest without that. ... You aren't learning anything until you are interacting with users, and learning is the most important thing you can possibly be doing. Through friction the apple is polished, I think.


Will the real standard terms please stand up?

 
I got a lot of feedback from my post on liquidation preference (some constructive, some very critical). This post essentially addresses those criticisms and makes some new points about seed financing.

First off, I'm not a so-called super angel, which I've made abundantly clear from the beginning. I'm just an entrepreneur who is starting to get into angel investing. And even then I'm an outsider/outlier. I've never taken investment beyond friends and family for any of my companies. I don't live in the valley or Boston or NYC (Philly actually). And I'm very-technical hacker (the good kind).

I'm opening up my new angel thought processes in real time as I get into it. I think this approach is very rare and that there needs to be more of it, so I figured I'd start in hope others would follow! I realized from the get-go this approach would generate a lot of flack, but that is par for the course. I grew a think skin a while ago, mainly from stuff like this. Needless to say, however, personal attacks, condescending tones, and snide remarks still annoy me. I'd appreciate it if you kept those things off of my blog (and everywhere for that matter). 

Anyway, in effort to continue my thinking and engender some more discussion, I want to address the various criticisms that have come up in response to my first post. The biggest point, which Nivi made best, was that I was proposing a non-standard term, and non-standard terms should be rejected out of hand for process reasons (as they will hurt your deal flow, among other things). 

I want to make clear I was never suggesting I would insist on this term in mass syndication deals. In fact, I'm not insisting on it at all. I thought it was obvious I was talking in the context of a term sheet negotiation where I was leading, i.e. playing off of valuation, etc. I realize now that wasn't clear and I should have qualified my post from the get-go. You live, you learn. 

That said, the bigger point I want to make is...

  • Would the real standard terms please stand up? Everyone's talking about "standard terms" without naming them. I've personally been collecting angel financing agreements over the past few years and they're *all different*. When people continually make reference to this magical standard they're implying that 90+% of deals look the same, and I'm proposing something in that wacky third-rail 10%. 

    There is no 90%. For each term, there are certain leading types people use. But often the leading one within those types doesn't even get a majority. And that's not even addressing specific language (implementation of the term type), which definitely matters btw.  When you vary each term across the whole term sheet, each final term sheet looks pretty different.

    Every angel or angel group has their own lawyer, and in turn, their own docs they'd like to push. And those docs are all different. And not just slightly different; widely different. As I said, they not only vary on terms, but also on specific language for those terms. They also vary on side-agreements they want to you sign, e.g. employment/IP/vesting agreements, etc.

    Only in the past few years have so-called standard docs appeared on the seed scene. By my count there are four of them that people take seriously--Techstars, YC, Series Seed & Founders Institute--and they vary widely too! There's a great post on some of the macro differences between YC, Techstars & Series Seed. 

    For example, Techstars has broad-based weighted average anti-dilution whereas YC and series seed have none. Each has different protective provisions. Series seed has a right of first refusal, whereas YC and Techstars are silent on that point. Series Seed also has drag-along rights while the others don't. YC has no future rights, whereas both Techstars and Series Seed have different future rights. etc. etc. Bottom line is they're different. And none of those differences even addresses the macro convertible debt trend. (Even when they agree on a macro level, again, the micro language varies.) 

    Recently, Brad Feld tried to get these to converge into one set and then quickly gave up because basically no one could agree and had no compelling reason to do so. So bottom line, I reject the premise that there are standard terms in seed deals.

    I've tried to find hard data on it, and I'd welcome/encourage/love more experienced people to provide some. All I can find on liquidation preference in particular is WSGR's market data (part of their Term Sheet Generator). As you can see, it varies a lot. Yes, I realize these are Series A rounds, but it's all I have at the moment (besides the deals I've collected personally, which I said are all over the map). In any case, the VC world is being disrupted. VCs/angel groups who do Series A rounds are also doing seed rounds, and as far as I can tell they're bringing their terms with them, or at least some of them. 

  • There are good reasons there are no standard terms. Why can't anyone agree on magical standard terms? There are a lot of reasons, e.g. people have varied experiences (edge-cases they want to cover), people see different types of deals (even seed deals), and it's hard to get rich lawyer types to agree in the first place :).  Brad has another good post on why it's hard to agree to particular language.

    But there is an important underlying point here that all seed deals and their terms shouldn't look alike. That is, every deal is indeed different. Three examples are 1) each deal has a unique set of risks and sometimes you want specific terms to account for those risks; 2) some entrepreneurs and investors want specific terms, e.g. certain valuations, and so other terms need to crop up to come to an agreement (if both sides really want to make a deal); and 3) deals come in different shapes and sizes.

    On this third example, consider my case. I'm ideally looking to deals really early in really small rounds (<=250K) where, if everything goes well, there will be no need for follow-on VC. Those specifics change a lot of things with regards to terms, and I hope put my original post into a bit more context. This is another thing I should have made abundantly clear in my first post, but failed to do so.

    In that context, convertible debt doesn't make sense since there will ideally be no follow-on round. Additionally, a pile-on preference is likely to matter less, since if they do end up taking VC, it's likely to be a smallish Series A (or even another angel round).

    For the record though, I welcome standardization as much as it is possible. I don't want to pay any legal costs like anyone else (well, mostly everyone), and I'd love to use these converged standard docs, which is why I think...

  • My proposed docs are arguably more standard than you're going to find elsewhere. Like I said in my first post, I'd like to use the Series Seed docs pretty much *verbatim*. In fact, my proposal was literally to change one word in them, from a one to a two. I'm guessing other people using Series Seed are changing things here or there and adding side agreements on top of them. But more to the point, if you go out and try to get financing, you're, for the most part, not going to get open source docs that you can read ahead of time. I'd personally like to be able to offer those.

  • Liquidation preference is a negotiation wrt to the whole term sheet. As I said above, if you want to insist on particular terms, all you're doing is pushing all the negotiation onto valuation (and option pool size). That's fine I suppose, but you can arrive at better compromises in certain situations by opening up more terms to negotiation. That's what I heard from Fred in his post. He negotiates in various types of liquidation preference in certain situations, mainly when there is disagreement on valuation.

    OK that's all well and good you say, but 2x liquidation is still non-standard and no one wants it, to which I reply.

  • I'm not wed to a 2x non-participating preference. Several well known angels commented to me that they prefer other liquidation preferences (other than 1x, non-participating) including 1.5 participating (with a cap) or dividends. George Grellas (startup lawyer) said on Hacker News "in my experience, in all normal investment environments, founders will resit it for 1x only (usually going for participation with a cap)." First of all, this further goes to the point of there not being a universal standard. Secondly, I don't so much mind any of these choices. They're all basically the same if you run the different scenarios on them.

    I picked 2x non-participating as an alternative to participation, in response to Fred's comment (and my limited experience) about entrepreneurs hating so-called "double-dipping." I have also read that dividends can cause accounting headaches and in some cases on-the-books insolvency. So my response was basically summed up in: OK, people hate participation and dividends, and you can get to the same place using 2x non-participating, so why not go there? The insistence that it is somehow worse than those seems a bit silly to me. Is it for no other reason than you see that less nowadays? Btw, in Brad's post on participation he notes how the so-called "standard" has evolved and is different to begin with across coasts.

    Going further, why is that all these other things are allowed to vary across the docs, but people have some problem with liquidation preference in particular? Or is it just that I brought it up, everyone has different opinions, and people just react to things they're not used to within their experience? 

    But like I said, I'm pretty much indifferent across these economic terms. At this point I'm just intrigued.

  • I don't want the entrepreneur to take all the risk. A bunch of entrepreneurs were pretty angry that I had the audacity to even suggest making a term more investor friendly. Again, I want to be clear that this is in the context of an overall term sheet (including valuation) discussion.

    My point was that I'd prefer to give on valuation a bit to make it more likely to make a modest return on a liquidation event such that I can continue to make angel investments, which would of course be allocated to fund more entrepreneurs. I'm putting up my hard-earned money (I got from entrepreneurship btw), and, if five years down the road, the company liquidates assets for some small amount, I don't think it is unreasonable to get a small return on that investment. 

    Let's consider two cases. I was essentially advocating for approximately a 15% nominal return. The real return would be less due to inflation. A 1x straight preference (non-participating) would be a 0% nominal return, and it's really significantly negative, again because of inflation.

    The second case is if you just got common, which a bunch of people said they would insist on. In that case, I would essentially lose most of my money whereas the entrepreneur would get most of the sale price (in this liquidation scenario). I'm not saying I know for sure what is fair, but that doesn't seem fair to me. And more to the point, I'm not going to invest in anything for just common. As Fred said in his post's comments, "i think everyone who has cash at risk in a deal should have preferred stock. i have no idea why angels do these investments in common.".

  • I hope the liquidation preference never triggers. Contrary to what some people implied, I never want the preference to trigger. People seem to think at a 2x, nonparticipating preference (in a small round) skews incentives so much that I would want the entrepreneur to take a small exit. Nothing could be further from the truth. I only want to invest in things I think will have a decent chance of a medium sized return, i.e. one where this preference would never come into play because everyone involved will have done very well.

    That was sort of my point about choosing this value. Sure, weird preferences in certain situations can skew incentives, but I don't think this is one of them, especially in context of the deals I want to do. I'm considering very small rounds where the preference amount wouldn't exceed 500K total.

  • I'm looking for investments that, if all goes well, won't need VC. Of course, this could be a terrible strategy and I'm open to changing it, but that's what I'm going for right now. The most insightful argument I think was from Mark Suster, who said in the long-run this is bad because later investors will pile-on preference. Other people suggested every one should just be using convertible debt. I'm not saying any of that isn't true or great, but it doesn't work for this current strategy. Like I said above, when there is no VC, convertible debt doesn't make sense. And also, there is less of a risk of screwing up an eventual VC round.

    The point for the preference discussion in the first place, which no one really commented on, was that new angel investors could make more deals, and that's good for the ecosystem. Not that people should make personal decisions based on externalities, but I do think on a macro level more angel investments should be encouraged. So in small deals where there is no need for follow-on VC, why shouldn't the standard be for a modest preference to allow for those angels to do more deals?
All that being said, I'm really not that obstinate about any of this. I'm thinking out loud so of course my thinking is likely to evolve over time. Thank you all for the continued constructive discussion.

Liquidation Preference (my case for 2x, non-participating)

 
I recently closed my third angel investment and the first one I led from beginning to end. Leading made me think a lot about deal terms. We ended up using slightly modified Series Seed docs, which I plan (and would love) to continue to use. 

The one term we slightly modified from the model term sheet was the liquidation preference. As I seem to be at odds in this change with people much more experienced than myself, e.g. Fred Wilson and Chris Dixon, I want to lay out my thinking and hopefully get some feedback.

First, why would I ever differ with these guys? I think it's simply because I don't have as much money to invest, and as a consequence, my angel investing strategy is different. 

These guys are so-called super angels. And if I had more money I'd probably end up being one too. But right now, I have a limited pool of angel money. It's enough to do a bunch of deals and I'm fine with losing it all, but it isn't enough to do the YC/Conway (super angel) strategy.

Here's my basic argument. Suppose you have a "hit" rate of 10%. I realize it's more complicated than that and I've developed a spreadsheet to model it better, but for sake of simplification just go with me for a moment. 

At this rate, every deal you do has a 90% chance of not being a hit. People then think intuitively, OK, I need to do 10 deals then. Nope--the default intuition is wrong. What's the probability that you do 10 deals and don't get a hit? (9/10)^(10) =~ 35%!!! That's a massive %. At 20 deals you're down to 12%, but that's still pretty high.

So basically you have to do a lot of deals if you're at all serious about making money off of angel investing. A recent Monte Carlo simulation by Jeff Miller confirms this thinking. He concludes 20 deals is a sweet spot. 

If you're a new/small angel like myself with a fixed investment pool, what can you do to maximize the # of deals? Two things really. First, make smaller investments--though this isn't great because there's a lower limit where you'll get shut out of deals ($25K is probably the realistic minimum) and, when you do hit, you won't get that much back.

Second, liquidation preference. In my previous post on angel investment scenario planning, I noted that small returns (1-3x) don't influence overall deal pool IRR that much. And that's true in a static scenario. But the real world is dynamic and if you can do more deals you can increase the chances of hits, as noted above. Getting money back through liquidation preference won't move the IRR needle, but it will enable you to do more deals. And to the small angel (me) that is the most important thing.

If you have no idea what liquidation preference is (and you want to know!), check out Brad Feld's two great intro posts on the subject. The default term from the Series Seed Term Sheet is essentially "One times the Original Issue Price." That means in an exit event, the investors have a choice to a) get their money back or b) get their equity %. It's an economic choice. If it's a small exit and the equity % doesn't yield as much money as was put in, you'd opt to get your money back; otherwise, you'd opt to get your %.

Tweaks on this model are:
  • Get multiple times your money back (e.g. 1.5, 2 or 3 times) in choice a.
  • Get your money back first, and then also participate in the distribution of what's left based on your %, which is called participating preferred.
  • Participation, but with a cap. In this one you participate up to a limit, like 3x. So you get your money back, and then your % allocation, but if that exceeds 3x your money you have the choice whether to get that or your straight %.
Anyway, entrepreneurs seem to hate this stuff, especially the participation part. Some people call it "double dipping" because you get money back and then you double dip and get more money back out of what's left. I think this is somewhat of an understandable knee-jerk reaction, but everyone should look into different realistic scenarios to see what the actual implications might be. 

I woke up today to read Fred Wilson's evolved view of liquidation preference, which is that he used to insist on participating preferred, but now only does (and with a cap) in certain specific situations. 

Apparently Chris Dixon agrees with this view, and goes further saying "[a]nything more than that (participating preferred, multiple liquidation preferences) divide incentives of investors and the entrepreneurs. Also, this sort of crud tends to get amplified in follow on rounds."

My current thinking is that a 2x liquidation preference is a sweet spot. Let's look at a concrete example. Here is a spreadsheet I made where you can play around with it and other scenarios at your leisure.

Suppose you put in 50K in a 500K round on a pre-money of 2.5M (post-money 3M). You end up with 1.67%. Let's say the company doesn't take any more investment (for simplicity sake) and in year five it exits/liquidates.

In scenario 1, you got the normal 1x liquidation preference. In scenario 2, you get 2x. And in scenario 3, you get 1x, participating. Here's how those scenarios play out in terms of IRR at different exit sizes.

 1M - 0.%, 15%, 6.%
 2M - 0.%, 15%, 13%
 5M - 11%, 15%, 22%
10M - 27%, 27%, 34%
20M - 46%, 46%, 50%
30M - 58%, 58%, 61%

At high exits, the term doesn't matter much--they converge pretty quickly. It clearly matters <=5M (at least in terms of IRR). With 2x liquidation preference, your IRR jumps from 0 to 15%, a healthy % that you can use to re-invest (and do two more deals at the same size). And interestingly, you can see the participation right does worse than 2x at small exits, does better in the middle, and smooths out at the high end.

Now let's take the cons in turn.

  • Splits incentives. When you get crazy preferences, this can certainly happen. And if you have participating with a cap, as Brad notes in his post there is a plateau range in the middle at which the investors are indifferent to exit size, which is weird. But at 2x, non-participating, in a smallish round (<=500K) I don't see much issue with regards to incentives. The preference only kicks in for low exits (in this case sub 6M). The entrepreneur should not be getting financing if they would be happy with an exit lower than that.

  • Mucks up later rounds. There is a risk here in that, at the very least, you can expect later investors to get similar preferences. Brad points out scenarios where you can actually lose out as an investor by having these rights (if the next investors get them too). Again though, if they get limited to 2x, non-participating, I think that is a manageable risk.

  • They'll get thrown out anyway. I've heard this, but don't have enough experience to know if this happens or not. Ideally you'd also get some control rights on the next financing so at least you can be sure you won't get screwed in that next round.

  • IRR doesn't matter for low exits. It matters to me :). In particular, as stated above, if it did return the preference amount, this would yield the ability to do 2 more deals instead of 1. A few of those, and an initial pool of money allocated to 10 investments may easily stretch to 20.
Update: some good comments on HN

Update 2: I made a new post explaining more of the background on this post and addressing the comments. 

Angel investing portfolio scenario planner spreadsheet

 

irr.jpgSeveral friends have told me angel investing is not a good way to make money. If you can do the YC/Ron Conway strategy that is one thing, and if you just want to give back that's another, but doing it at my level is a waste of money.

I do want to give back, but I also want to make money with my angel investing. So I've been thinking a lot about strategies to employ to fulfill both goals. To that end, I've been creating spreadsheets that I'd like to share with you.

First, check out the Angel investing portfolio scenario planner (Google doc spreadsheet). To get an editable copy, select 'Make a copy...' from the File menu (or Ctrl+Shift+S).


This spreadsheet shows you the internal rate of return (IRR) of a fictional set of 10 investments of $25K. Really the amount per investment doesn't matter.

The investments have 5 year time horizons, i.e. the payout happens in year 5 (row 15). And each investment outcome can fall into 5 buckets: lose everything, return money, medium, medium high and high. The payouts of these outcomes are in column B, and the % breakdown (how many investments are in each bucket) are in column C.

If you play around with column C you can allocate different amounts of investments to each bucket and see the effect on IRR (G15). If you want you can also mess with column B to change the payouts of the buckets.

The following are some of my takeaways. I'd love to know yours.

  • My ambitious goal is for a 30% IRR. The default scenario is one way to get that, which is like the 1/3, 1/3, 1/3 a lot of good investors report. In this case, it's 40% lose everything, 30% return money, 10% medium, 10% medium-high and 10% high.

  • The return money bucket really doesn't influence overall IRR that much. If you change the default to 70% lose everything, i.e. take all the return money % and move it to lose everything, it only changes the IRR by about 2%. It certainly matters psychologically and it may free up more money to invest, but in this static scenario it doesn't really move the needle.

  • If you change the outcome of the high bucket (B11) much higher, you can see what it is like to invest in the next Google. You can also see that if it is just one of your investments that's fine, i.e. the oft mentioned 1 in 10 home-run strategy.

  • If you want 30% IRR, you really need to get a high outcome in there. This leads me to again wonder whether I should only consider events where I can see a realistic path to that high exit going on what is put in front of me.

  • The time horizon really does matter a lot. I added rows 16 & 17 to show the difference between a 5 year time horizon vs a 4 and 3 year one. VC-backed companies have significantly later exits on average. These scenarios make me wonder if I should really be looking at companies (at least in part) that could make it without VC.

Can the YC/Ron Conway angel strategy work for me?

 
index.gif
The YC/Ron Conway angel investing strategy seems to me to be: focus on finding really smart, determined people, and the returns will follow.

Their strategy makes perfect sense for them, but not necessarily for me.

FileRon Conway 1.jpg
Here's them:
                • Essentially unlimited funds to invest in who they want.
                • Incredible deal flow, probably capturing a large % of promising early stage startups in their investing spaces.
                • Lots and lots of deals.
Here's me (you probably know what's coming):
                • Orders of magnitude less funds.
                • Orders of magnitude less deal flow.
                • Orders of magnitude less deals.
Paul Graham was just on Mixergy saying potential exits are so unpredictable, he doesn't even think about them when making investment decisions. 

My premise is I can't do that because I simply don't do enough deals and don't have similar deal flow. Given these facts, I think angels like me probably need a modified strategy. Essentially, we should have a higher bar to invest. 

Yes, we should only invest in smart, determined people. Yet I think we also need to think at least a little bit about exit probabilities and magnitudes.

But doesn't that contradict Paul Graham's point that they are inherently unpredictable? I don't think so if you concentrate on more realistic exit possibilities.

That is, I agree that exits are unpredictable, but big exits are way more unpredictable. Googles are pretty much black swans. IPOs are less rare, but still pretty rare (at least in the past decade). And 100M+ exits happen somewhat frequently, but are still rare enough that YC hasn't had one yet in its five year history. 

But they will--it's just a matter of time. Ron Conway has had many big exits over his longer time span. Both YC and Ron Conway will make their great returns on these rare, unpredictable events. 

And that's the thing. I don't think I can count on being part of any big exit event at my small deal rate. But I think I can ensure more of a chance of decent returns (as opposed to super great returns) by thinking a bit about potential exits.

I should probably look for founders with some idea about customer acquisition and/or market. For example, a founder doing something interesting in the dating space would probably be more interesting for my strategy than a founder doing something in a brand new market with great yet completely unproved potential.

The bottom line is their strategy might get them in on the next Google. However, me following their strategy at my deal rate will most likely not get me anywhere close to the next Google. But with a modified strategy, I can probably still make decent returns and work my way up to their strategy, which I would of course love to do if I could.

How should I value prospective angel investments?

 
I've gotten more serious about angel investing lately, and I'm struggling with how to value prospective angel investments. 

Let's say my target is to get 30%/yr on my angel investments. If my investments have 5 year time horizons (on average), and 10% hit the high mark, that 1 out of 10 that hits needs to have a 37x exit event (on my share). If I was more successful at picking winners, say 2 out of 10, that drops in half to 19x exit events.

By the above logic, which I'm starting to believe, I should only consider investments that have a realistic opportunity, albeit unlikely, to return 20x on my investment. Should I have such a cutoff?

As my share in the company goes up, it gets more likely that their high exit outcome will return the required amount. I probably won't put in much more money per deal, so a higher share for me means getting in early and/or being really hands-on.

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