Monthly Archives: February 2007


One day, I saw someone handing out these small photographic cards with their contact info on the other side. They were photos that this person had taken and I thought it was a great idea to meld photography, or life imagery, with a personal identity system. I was hooked. I had to make some too! Enter . allows you take photos from flickr or bebo and make cool business cards out of them. These can be from pictures you have uploaded into your own account, or they can be semi-randomly selected from the gazillion photos on either service.
I took some of my own favorite shots and uploaded them into flickr. Then I went to and they have a great interface for selecting which pictures you want, cropping them, setting up the text on back, and the ordering them.
For one batch, the result wasn’t that great; they sometimes don’t print so well. However, my second batch came back really cool and you can see them in the picture above. The second batch was a personal business card and I just ordered another batch of business cards, with candid photos from all the startups I work with on the back.
I love the way they make printing these cards so easy. It’s also an interesting way of expressing yourself (or your business) through the use of photography, a lens into the world through your own eyes. Something to share, something to tell your own story with.
I can’t stop ordering these cards!

FlipperNation: The Future of Real Estate, The Future of Video?

By some fortuitous circumstance, I met these guys at FlipperNation:

FlipperNation is about 2 guys who are trying to make it rich by flipping houses. The episodes show their misadventures at flipping their first house and all the strange people they deal with around house flipping like other realtors and contractors. It’s really great stuff and I can’t wait for the next episode.

What was really interesting about my meeting with them was that it got me thinking about the state of video content today in the world of the Internet, interactivity, and declining TV viewership. As I wrote my first email to them, giving them some feedback on what could make their internet video show better, I thought about the ways that some video outfits were getting really creative at leveraging the Internet and interactivity to engage the viewership in ways that was not possible in the days before the Internet.

Passive TV consumption is waning. Users are getting more sophisticated and want something that involves and communicates with them rather than sitting there like drones and just receiving.

My first encounter with interactivity aligned with a TV show was way back around 1999 when “Who Wants to be a Millionaire?” was the big thing, and they rigged this Internet game that played along live with the TV show itself. You could play against other players who also played along, and winning gave you points which could land you on the main leaderboard. It was incredibly well orchestrated, and it must have been a nightmare to manage as it needed to coordinate with the current live showing in 4 time zones.

Another example of using the Internet is with Sci-Fi Channel’s Battlestar Galactica where, between seasons, they shot a whole series of shorts that connected the last episode of the previous season with the new upcoming season, and showed them on their website. It was a way to inexpensively engage viewers while the new season was being prepared, but yet keep them interested and wanting more as the story line unfolded. Also on the website are podcasts, additional commentary, images, interviews with the stars – Sci-fi Channel did a great job of filling out the blanks for curious fans to consume, whereas in pre-Internet days this information was impossible to see.

FlipperNation already had employed some of these types of ideas. They have employed guerilla marketing such as getting on MySpace and each character has a page as well. Their website includes a whole bunch of content related to real estate and the art of flipping houses. They have an email address where you can submit your house to be on the next episode of FlipperNation. We brainstormed on many more ideas at our meeting yesterday, extending on the usage of the Internet, engaging the viewership and keeping them humorously hooked.

I think FlipperNation has legs. They are now looking to sign up with a studio and go big. I will be watching them and hope one day I can say, “I knew those guys when they were nobodys, and now they’re somebody!” That’s show biz!

Swimming with the Sharks: Part I

Last week I had a meeting with a friend turned entrepreneur. We talked about the company he was forming and it sounded really interesting, interesting enough for me to put in some early money into it. We then moved to talking about possible angels who would fill out a first funding round.
These were angels who were also individuals very prominent in the area of business he was going into. They were definitely going to be helpful in building the business and be able to make the chance for success much higher.
Since he was my friend, he also told me what these people were like. They are very money focused. And they will do anything to maximize their gain, potentially at the expense of others.
I thought about this for a moment. At first, I thought what could happen if I were to invest early, probably into a convertible note, and then convert to the preferred series? Aren’t I protected by preferred rights?
Then it dawned on me what could happen. Let’s say the preferred round closes. Then a few months later, the board is faced with the other angel investors proposing to change their own rights. They propose changing them so that they can, upon majority vote of the shareholders, buy out any shareholder. My friend who will undoubtedly be on the board of directors may oppose this, knowing why this is being proposed, which is to squeeze me out. He tries to defend me but then the angels apply leverage in that they could make life much more sweeter to him and his business if he agrees to the change in rights. My share in the company leaves me no leverage at all. I have not put enough money into the company so that I can defend myself in this proposal through vote alone; I don’t have enough share in the company.
In this scenario, the vote passes with my friend/entrepreneur bowing to the needs of the company and the next vote is buying me out, perhaps with a bit of profit, perhaps not.
There is a possible solution. That is to propose that I go in with my seed money and demand a board seat. This should protect me for at least one round of funding, but after that I will probably need to relinquish my board seat in favor of whomever is coming in with subsequent rounds of funding. I do not know if my friend would agree to this or not, or if I would even want a board seat. I am thinking on this some more…
Early stage angels are definitely in a tough position when we come in early, and often with small amounts of money relative to the cash coming in for later rounds. We take the most risk, but yet we are left with no leverage later on, as the needs of the company outweigh shareholder need.

SunshineNYC: Office Space for the Geek Cool

I really love this office space operation in Manhattan, Sunshine Suites, this one at 419 Lafayette near Astor Place:

The tree branches around the conference rooms is a bit freaky. Makes you feel like they are going to reach out and grab you. Don’t have a meeting here while on drugs!
It’s only about $400-$500/month for a desk. You get a phone, internet connection, unlimited usage of xerox and fax. And it’s decorated in New York chic. The entrance to the floor looks like the W Hotel. There is even sexy house chill music playing in the bathrooms to relax you when you…well…you know…

Legal Help is Showing a Depressing Pattern

So far, my scorecard for legal help for startups and investors has been pretty dismal.
Let’s see. The stories go on:
An LLC agreement costs $6000 to create but upon dissolution of the LLC the agreement has ambiguous terms on who owns what and causes tons of issues upon dissolution. Note that an LLC agreement can be created and filed in about $1000.
A term sheet is created by a new associate who is new to Silicon Valley and barely has any experience in startups and financing. He tries to snow an investor during a call to defend his terms and the investor, who happens to be seasoned and coached by his really good lawyer, refutes every point made by associate, who concedes at the end of the call that investor was actually experienced and compliments him.
The night before the first investor meeting, a lawyer totally flakes on entrepreneur and doesn’t have a term sheet done! It arrives around midnight the night before and there is no time for review at all.
Entrepreneur asks for term sheet, and lawyer delivers one. Investor reviews and finds provisions that have no meaning whatsoever to the current deal. It is obvious that lawyer cut and pasted from a previous deal term sheet and didn’t bother to review and check for relevance to current deal, costing everyone in time and legal fees.
Entrepreneur asks for advice from lawyer on what to do from a financing standpoint, and gets almost no worthwhile advice whatsoever. Friendly investor guides entrepreneur through all the possibilities and helps develop a financing strategy.
Investor asks lawyer for help on looking at startup term sheet and gets back worst case scenario response on the whole thing. Investor initially gets cold feet, but quickly realizes that this particular lawyer is the most conservative, worst case scenario lawyer in the world, and investor realizes that risk is a part of life for the early stage investor and that this lawyer isn’t the right person to advise on early stage investments. If investor had listened to this lawyer, investor probably would never make any investments at all and would rather sit home and stuff money in mattress.
Legal help is crucial to both the entrepreneur and investor. It doesn’t matter that the legal help sits in a big expensive firm or a smaller shop. Why can’t we find good, dependable, and experienced legal help?

Convertible Notes versus Preferred Equity Part III: The Investor

In the last few months in working with financings, I have gotten to know the Convertible Notes versus Preferred Equity issue very well. As an angel investor, I am constantly thinking about maximizing my money and I don’t have the cash to play the field in a broad, diversified way to not care about this issue like some larger angels. Thus, knowing when to take a deal or walk away is part of the game, and certainly financing terms are part of that decision.
Again, I reference Josh Kopelman’s post on Notes and Preferred Equity and think it explains many details well. I’ll talk about this topic with his thoughts and some of my own in mind.
Why would I be OK with a Note?
The terms must be good.
Often Notes have no anti-dilution provisions or special provisions that help us in case the next equity financing does not occur. They seem to be hastily drawn up and many details are left out. I have walked away from Notes that didn’t have enough good terms in there.
They are mostly unsecured, so I’m OK with that. I know that I’m dealing with an early stage startup and they have little or no assets at this point. What would I do with 1/10th of a PC?
I also want to make sure I am not locked into a particular Next Equity Financing by default. I want to have the ability to back out if company conditions change.
If they require an auto-conversion provision in their to the Next Equity Financing, then I want them to insert a minimum on the money raised, to ensure that they don’t do something screwy.
In truth, I don’t pay much attention to the interest rate return for early stage startups. This is usually a make or break time for them. If they don’t get the Next Equity Financing, then often the company will tank and I won’t get any interest payment or my money back yet. I do just make sure it is in range of other Notes I’ve seen which is about 6-8% per annum.
There is a Preferred Series financing imminent.
Most Notes are used to gain cash to continue company operations just prior to a first Preferred Series financing. My goal is to always get share of a Preferred Series. If I know there is one coming soon, then I’m OK with a Note knowing that I’ll convert in a few months. Time is minimized between the Note and the Preferred Series and there is a less of a chance that the company valuation will change dramatically, causing loss in ownership share from when I invested and when it converts.
Why would I NOT be OK with a Note?
There is no Preferred Series in sight, or I am not confident it will happen soon.
If the Note is being raised, but they have nebulous plans for raising the next Preferred Series. I won’t do it. The risk of it dragging on for a long time is there, and the more time that drags on before I gain actual ownership in the company, the more chance that it goes not in my favor. The valuation could go up (meaning I convert to less ownership than I originally thought), the company could go under with not enough funds, or I mayjust get paid back and not reap any benefits of having ownership in the company, if the company starts gaining revenue. The company need not be going under for you to not gain the benefits of investing in a company.
Or they may SAY they are going for Preferred Equity fund raising, but I get the feeling they will drag their heels or avoid seriously doing it. As soon as I get some intuition that this is true, I won’t do it.
This is a second (or beyond) Note they are raising.
This begs many questions. Is the company trying to be greedy and not give up any ownership? If so, they can build their company on other people’s money then. I want to maximize return and getting interest rate return on my money is not the way to go.
Or you have to wonder why this is yet another Note. Why do they need another Note? Why haven’t they raised their Series A? Or what is wrong with them that they can’t raise their Series A? Many Notes are written vaguely that the Note will convert to Next Equity Financing. They may actually want to convert the last Note holders to the terms of the second Note which may be less favorable to them!
Unfavorable Terms.
Although this may seem like a given, it could mean that the company opportunity is really good, but the Note terms are not.
Terms always take care of the worst case scenario and nobody wants to see them come into action. But sometimes, the terms are there and you can’t change them. I’ve already had a case where I wanted to change the terms but the entrepreneur did not because the current terms were already approved by the lead investor, and he did not want to scare the lead investor off. But, it was obvious that the lead investor didn’t really read the term sheet carefully because some of those terms were bad even for him.
By the way, I think this happens frequently in the Valley. There are so many large investors that when they invest, it is a small amount for them but large enough to make them lead investor. But they go through so many deals that they don’t seem to be spending time on the terms at all. I’ve heard from one person that they just write off investments that get diluted to nothing or fail, and employ diversified investing across many different investments and hope that a few make it big to cover the many that return little. Very frustrating for us smaller angel investors.
Always be ready to walk away no matter how good parts of the deal looks…
Investors are not aligned with interests of the company in building value.
Clearly stated in Josh Kopelman’s post, it makes sense that as investor I want the valuation kept as low as possible so that I convert to as high ownership as possible. But my model is to help entrepreneurs as much as possible. So if I end up helping them and sign up as advisor, but feel that a Note they may be presenting may not be in my best interests, I may end up not investing at all.
Why I like Preferred Series.
I have ownership in the company.
I gain immediate ownership in the company and this point is not nebulous, as in the situation of the Note.
Generally, preferred terms are pretty favorable to me.
There will be provisions for voting, company control, preference in paying back, potential dividends, etc.
I am aligned with the interests of the company.
Once I have ownership in the company, I can freely and without reservation help the company build value, as my own value in the company will also grow.
Why not Preferred Equity?
Not many reasons to not jump into an investment if Preferred Equity is offered, assuming all other factors are positive.
Sometimes, there is a gotcha in the terms.
Potentially the terms could be not quite right. This happened once where the voting rights were not favorable to the Preferred Series Angel round. I caught this at the eleventh hour and thankfully the entrepreneur agreed to a change in the docs to make this more favorable. Otherwise, our terms and rights could have been wiped out without us having any say in it! You always need to review the terms no matter what and I would do it with a seasoned lawyer who has done many financings before, and hopefully from the perspective of company and investor.
Caveat Emptor – “Let the Buyer Beware” – words to live by and in the investing world you have to dig into every little detail in every deal. It costs more in time and money, but it keeps me out of trouble.

The Amazing Pace of Change at My Alma Mater, Yahoo!

I just found the email that detailed the re-org at Yahoo! from Sue Decker, head of the new Advertiser & Publisher Group. It’s posted at Techcrunch:
Text of Email to all Yahoos, Techcrunch
I have been out of Yahoo! since Sept 2004, and in 2+ short years, I see:
* Lots of EVPs and SVPs. They used to make you run the gauntlet before making even VP.
* I only recognize about 6 names in the email out of about 15. The influx of new people is staggering at the higher levels. Where did all the people I knew go?
* The company is organizing in a very “large company” way. The changes were in the making while I was still there, but now they are extended more.
* Valleywag’s post about slightly less kneeling before Zod is a bit cutting, but it does make a point. I am not sure that splitting engineering (and by the way I heard through the grapevine that my old user experience group is reporting into the product teams now too) is going to be good for the company in the long term.
To me, companies always undergo cycles; they try things, they work or don’t work, and then they go back to try old things, and then they work/don’t work, and then you’re back to trying stuff you tried before. I suppose it’s one way to keep the world off balance to distract you from other possible issues with the company.

Convertible Notes versus Preferred Equity, Part II: Enterpreneurs

In reading my last post, one may start to think on why either method may be more or less desirable to an entrepreneur seeking to raise cash.
Why a Note?
It is Cheap.
Early stage startups typically have little cash to spend. Closing a Note allows them to bring in money in the cheapest possible way. Preferred Equity will cost them 10 to 20 times more.
It is Fast
Often startups need cash as fast as possible to fund short term operations. A Note closing can be accomplished in as little as two days.
It is Unsecured
For early stage startups, every Note I’ve seen has been unsecured. If the company goes under, there is no obligation to pay the Note holders back. It could be secured by assets, but generally for early stage startups it is not. Why would you get paid back with 1/10 of a PC?
Maximum Flexibility
In the case of early stage startups, we talk most often about a Convertible Note which Note holders want to convert to some version of stock in the company. Depending on how vague the language of conversion is, a startup could convert the Note holders to common stock, to Preferred Equity, or even to the terms of another Note. There is the potential for maximum flexibility on the part of the company as, in theory, it could convert to anything if they word it right. Another aspect of flexibility comes in next financings. For instance, with a Note, valuation for the company has not been set yet so there is freedom to adjust. It also means there are no preferred shareholders and could be more attractive to certain large investors who want more control in the company.
It is Low risk
The Note holder often has an interest in helping the company and getting in on the ground floor, and they can be generous with the payback period and the terms. Assuming the company either gets to a place of generating money or raising more, a Note of this type can be paid off prior to the due date, or converted to preferred in the financing, in which case the Note turns into equity and expunges the debt.
Why not a Note?
Not many reasons to not use a Note first, from the company perspective.
It misaligns helpful investors with the company.
The startup may have some investors whose contacts you want to leverage, or who are actively giving you help. By executing a Note, the startup creates a situation where the investor is not incentivized to help the company. If the company grows in value, and since Note holders don’t have actual ownership in the company yet, then Note holders gain smaller share of the company when the Note converts. Helpful Note holders want to help, but they will see their potential stake in the company if they help drive the valuation of the company upwards.
But read on for some thoughts on Preferred Equity.
Why Preferred Equity?
It aligns the interests of helpful early stage investors with the company.
In Josh Kopelman’s blog post about Bridge Loans vs. Preferred Equity, he explains it well. Once investors jump into a preferred series where they have actual ownership in the company and feel good about building value with the company, as their own value in the company increases with whatever value they build.
It rewards early stage investors with their support of the company.
Early stage investors have the riskiest position. They go invest in a company early, and often they get their stakes diluted by subsequent investments until they get nothing back. This seems grossly unfair for people who supported the entrepreneur at such an early time when there is barely no clear value built yet. With a preferred series raised with the earliest investors, they are rewarded for giving their support early on and the preferred equity will most likely resist dilution with the proper provisions.
It attracts investors.
Like with the previous item, preferred series are just more attractive to investors simply because you gain immediate ownership of the company and not have to deal with potential uncertainty of Convertible Notes. Entrepreneurs can increase their chances of getting more investment by offering this early on. Many investors are gunshy of Convertible Notes and want ownership immediately.
Why not Preferred Equity?
It’s expensive in time and money.
You spend more money executing the paperwork, and there is a lot more paperwork to do. This may be too much for an early stage startup to bear financially.
It could deter future investors.
Venture funds don’t like to have others in potential control of the company. They want it all. Other preferred shareholders could present a problem here as they may have preferential voting rights, perhaps even a board seat. Also, preferred equity terms often have anti-dilution provisions which prevent future financings from grabbing a larger stake in the company.
Operationally, it adds a bit more complexity.
Now a preferred shareholder elected board member may be present, so there may be another voice in the operations of the company. Potentially, other large directional moves by the company may require the preferred shareholders to agree via vote.
Still not an exhaustive list, but some thoughts I’ve picked up along the way. More interesting thoughts in Part III from the investor point of view, coming up next!

Convertible Notes versus Preferred Equity, Part 1.5

Oh one other quick word.
When I started dealing with term sheets in both Notes and Preferred Equity, I strove for understanding. I went in thinking that this was an orderly process and that there were standard contracts for this sort of thing.
The one thing I learned is that NOTHING IS STANDARD.
Terms are written purely on whatever the entrepreneur and the investor(s) want. Yes, there are standard things like interest rate payments or anti-dilution provisions, but as for what interest rate to pay or which type of anti-dilution provision of which there are many…all up for grabs.
So if anyone tells you their term sheet is standard in the industry, don’t believe them. Everything is negotiable, so just say, “Thanks I’ll take a look and get back to you.”
Onwards to Part II…