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Hi, I’m Brad Feld, a managing director at the Foundry Group who lives in Boulder, Colorado. I invest in software and Internet companies around the US, run marathons and read a lot.

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AngelList Syndicate Feedback From An Experienced Entrepreneur

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We recently funded Blinkfire Analytics using our FG Angels Syndicate. The CEO and founder, Steve Olechowski, was co-founder / COO of FeedBurner, which Google acquired in 2007. I was an investor and on the board of FeedBurner, which is how I got to know Steve.

If you don’t know the FeedBurner story, there were four FeedBurner founders – Dick Costolo (now CEO of Twitter), Eric Lunt (now CTO of BrightTag and until recently a board member at Gnip, which Twitter just acquired), Matt Shobe (now at AngelList), and Steve.

In addition to bootstrapping his new company forever (since he’s a multi-time successful entrepreneur), Steve could easily raise an angel round any time he wanted to. So, we were psyched he was willing to do an FG Angels Syndicate with us.

Steve had some unsolicited comments for me, AngelList, and angels as a result of the process. I asked him if I could post them – he said yes. Following is a thoughtful set of reasons AngelList is so powerful, along with some constructive feedback for us to consider.

1) Some of your backers are really good citizens.  When it was oversubscribed they kept their syndicate commitment, but offered a much bigger investment outside the syndicate.  When 50% of the money didn’t close, they went back and put it back into the syndicate.

2) You have a bunch of “shadow backers” who seem to follow your investments, and then try to go direct to invest to avoid paying your carry.

3) There are some backers that request an awful lot of due diligence for a $1000 investment.   If they are that worried about losing $1000, perhaps AngelList isn’t the right place for them to be investing.

For us, the benefits of the syndicate are:

1) Access to capital we wouldn’t have otherwise been able to raise on angel list, and offline

2) Keeping the number of entries on our cap table relatively small

3) Though #2, we still have the transparency of knowing who the “LPs” are, and can mine them for help if needed

For the investors, the clear benefits are:

1) Access to deal flow they wouldn’t otherwise get

2) Ability to diversify their funds without a huge minimum ticket

3) Piggybacking on an investment thesis without having to do the research

The only negatives so far are the days of uncertainty where do you don’t know how much is going to get filled and if you need to generate more demand or turn people away on a daily basis.

Mentors 1/18: Be Socratic

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Since today is the first day of the new Techstars Boulder program, I figured that it’s time to get rolling Deconstructing The Techstars Mentor Manifesto.

My goal with this series of posts is not to get the detail right, but to flesh things out and get your feedback. So please comment on anything and challenge everything to help me get it better.

First up (of the 18 items) is “Be Socratic.”

If you think “be socratic” means “ask questions”, you are partially correct. When David Cohen was crafting the mentor manifesto, it was obvious to start with “be socratic” since such a key part of the Techstars mentor process is to ask questions. But it’s not just the act of asking questions, it’s how you ask questions, what you try to accomplish with the questions, and what your responses to the answers are.

The “how” is important. As a mentor, it’s easy to establish a 1-up / 1-down relationship with the entrepreneurs you are talking to. In most cases, you start that way, especially with first time entrepreneurs. However, your goal should be to create a peer relationship, where the mentee learns from the mentor and the mentor learns from the mentee. As a result, tone matters. A lot.

The cliche “there are no stupid questions” applies. Body language matters. If you – as the mentor – don’t understand something, ask a question. You don’t have to show the mentee that you are smarter than her. You don’t have to establish your credibility – you already have it.

While one of your goals with these questions is to learn more about the company and the problem you are exploring, recognize that if your engagement with the mentee is a one-way Q&A session with no clear goal, your mentee will only be getting part of the value out of the experience. Use your questions to guide the discussion, presumably toward testing hypotheses you might be developing in real time. Be explicit about these hypotheses as you are testing them and try to show your thought process through the questioning. This can be subtle, where you just guide things along, or it can be explicit, where you state your hypothesis and then start asking questions.

Your goal should not be to come up with the answer and state it, but rather to help the mentee reach the answer or a set of new hypotheses she can test. This is a collaborative process, especially if you are trying to develop a peer relationship. It won’t happen comfortably in your first interaction, but after a lot of time together you’ll find you are learning from each other during the process and reaching a better set of answers, or at least new hypotheses to test.

In the same way that how you ask the question matters, how you respond to the answers matters just as much. The corollary to “there are no stupid questions” is “there are no stupid answers” and it’s just as important to realize that. For most people, answering questions in real time, especially when you are getting them from lots of different directions (as in multiple mentors over a short period of time) can be intimidating. When a person hasn’t thought deeply about the answer to a question, or hears a new question for the first time, the answer often doesn’t really address the question.

When this happens, just ask “Why?” If you’ve never heard of 5 Whys it’s one of the most brilliant things I ever learned about getting to the root cause of any issue. The example in Wikipedia is wonderful, since it reminds me of Zen and the Art of Motorcycle Maintenance.

The vehicle will not start. (the problem)
Why? – The battery is dead. (first why)
Why? – The alternator is not functioning. (second why)
Why? – The alternator belt has broken. (third why)
Why? – The alternator belt was well beyond its useful service life and not replaced. (fourth why)
Why? – The vehicle was not maintained according to the recommended service schedule. (fifth why, a root cause)

What matters here is the root cause. And that’s what you are trying to get to with your questions. So don’t dismiss the first answer – keep digging. And use the third answer to set up a few hypotheses because at this point you are actually getting into the meat of the discussion.

The goal is not to end up with the definitive answer to the questions. Rather, you are trying to use the questions to set up a new set of hypotheses to go test. You are at the beginning of a long arc of inquisition – use being socratic as a continuous process to try to find answers.

How Can This Be A Billion Dollar Company?

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I was in the bathroom this morning catching up on all the blogs (via Feedly) that I hadn’t read this week since my head was in a bunch of other things. I came across one from Nic Brisbourne (Forward Partners) titled I’m a stock picker. I wish he had called it “This Unicorn Thing Is Bullshit For Early Stage Investing” but I think he’s a little more restrained than I am.

My original title for this post was “How Can This Be A Billion Dollar Company and other bullshit VCs ask early stage companies.”  It was asked by VCs to several companies I’m involved in last week. While I get why a late stage investor would ask the question when the valuation is in the $250 million range, I really don’t understand why a seed investor would ask this question when the valuation is in the $5m range.

Now, I’ve invested in a few unicorns in my investing career, including at least one unicorn that went bankrupt a few years later (I guess that’s a dead unicorn.) But I’ve also invested in a number of companies that have had exits between $100m and $1b that resulted in much larger returns for me, both on an absolute basis as well as a relative basis, than unicorns have for their later stage investors.

I’ve never, ever felt like the “billion dollar” aspiration, which we are now all calling “unicorn”, made any sense as the financial goal of the company. Nor have I felt it made sense as a VC investing strategy, especially for early stage investors. We never use the phrase “unicorn” in our language at Foundry Group and while we aspire to have extraordinarily valuable companies, we never approach it from the perspective of “could this be a billion dollar company” when we first invest.

Instead, we focus on whether or not we think we can make at least 10 times our money on our investment. Our view of a strong success in an investment in a 10x return. Our view is simple – we don’t really view anything below 3x return a success. Sure – it’s nice, but that wasn’t a real success. 5x – now that’s nice. 10x – ok – now we are in the success zone. 25x – superb. 50x or more – awesomeness.

We also know that when we invest in three people and an MVP, we have absolutely no idea whether this can be a billion dollar company. Nor do we care – we are much more focused on the product and the founders. Do we think they are amazing and deeply obsessed with their product? Do we understand their vision? Do we have affinity for the product? Do we believe that a real business can be created and we can get at least a 10x return on our investment at this entry point?

I recognize other VCs have different strategies than us, especially when they are investing at a later stage. Applying our model, if the entry point valuation is $100m or more, then you do have to believe that the company is going to be able to be worth over $1 billion if you use a 10x filter. But in my experience, most later stage investors are focused on a smaller absolute return as a threshold – usually in the 3x to 5x range. And, very late stage / pre-IPO investors already investing in companies worth over $1 billion are interested in an even smaller absolute return, often being delighted with 2x in a relatively short period of time.

So, let’s zone this in on an early stage discussion. Should the question “how can this be a $1 billion company” be a useful to question at the seed stage? I don’t think so. If it’s simply being used to elicit a response and understand what the entrepreneurs’ aspiration is, that’s fine. But if I asked this question and an entrepreneur responded with “I have no fucking idea – but I’m going to do everything I know how to do to figure it out” I’d be delighted with that response.

Dear VCs: What Happens When Your Words And Your Actions Don’t Match

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Almost exactly a year ago I wrote a post Your Words Should Match Your Actions. It was a generic rant that resulted from me watching a couple of VCs blow up their reputations with entrepreneurs I know because of how they treated them.

This morning I ended up on an email thread about this. I’m going to anonymize it, but you’ll get the point. The two people (who I’ll call “Entrepreneur” and “VC”) are both very successful, extremely smart, and very visible.

Entrepreneur: Thread below is 2+ years old, but resulted from VC asking me similar questions. Interestingly, when I (a year later) pinged VC about my new company, not even the courtesy of reply from him. Bad mojo. :-)

Me: Welcome to the “assholeness-VC-factor.” Hey – I’m important – give me info. Oh – you are now raising money – fuck off.

Entrepreneur: I’m amazingly appreciative to short, polite “no thank you’s”. I don’t know whether VCs think that’s too much work, or whether they want to leave open the possibility of the “must have been caught in my spam filter” excuse when the startup becomes a rocket in 2 years?

I then went on a more serious rant explaining what I think is going on.

It’s worse that that.

In my book Startup Life (that I wrote with my wife Amy) I said that one of the key things that has made our relationship work is that I realized “my words had to match my actions.” After about decade of telling her she was the most important person in my life, and then being late to dinner, canceling things at the last minute because something else came up, or taking a phone call without even looking at who was calling when we were in the middle of a conversation, she’d had enough and our relationship almost ended.

My biggest behavior change 14 years ago was to focus hard on having my words match my actions, and my actions match my words. Simple to say, really hard to do.

Of course, it also works in a business context. I’ve learned, and deeply believe, that it’s the essence of being authentic. You can have any style you want – these two things just have to match up.

Sadly, many very successful people simply don’t understand or appreciate this. They put huge amounts of energy into developing a public persona. It could be PR, it could be speeches, or writing, or systematic campaigns over a period of time about themselves and their businesses.

But then their words and their actions don’t match up. Over and over again. It can be subtle or overt. It can be mild or jarring. It doesn’t matter – if they haven’t internalized the idea of their words and actions matching up, there is a long negative reputational effect.

And, as our email exchange demonstrates, it lingers. I have heard the same thing about that VC and I’ve experienced it personally. Yet his public persona is “entrepreneur friendly”, “very accessible”, “incredibly smart”, and “highly capable.” Yet, he completely blew you off, after asking you for something when you were a powerful and well-connected executive at a large company. Stupid behavior on his part.

Oh, and in addition, this VC missed a chance to invest in what is now a rocket ship. And the entrepreneur didn’t go back to him for the Series B because he got blown off the first time, so the VC missed two chances to invest.

Do your words match your actions? If you don’t know, ask yourself at the end of each day “did my words today match my actions.”

Digital Paralysis

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I heard a great phrase from Jenna Walker at Artifact Uprising yesterday. We had a Blackstone Entrepreneurs Network Colorado meeting with her and her partner and in the middle of the discussion about their business Jenna used the phrase “digital paralysis” to describe one of the things she thinks is driving the incredible engagement of their customers.

Her example was photography. Artifact Uprising came out of her original experience with photography, the dramatic shift to digital photography on iPhones and picture storage on Dropbox and Instagram, and the massive overwhelming feeling of having zillions of digital photos. In Jenna’s case, it’s caused a slow down of her photo taking (digital paralysis) because she’s overwhelmed with the massive numbers of photos she now has, doesn’t really have the energy to deal with them, and resists taking more because they’ll just end up along with the other zillions in Dropbox.

I totally identified with this. Amy and I have a huge number of digital artifacts at this point – with our enormous photo library being just one of them. The feeling of paralysis in dealing with them is substantial. After a brief tussle the other day over “hey – just share the photo stream with me of the stuff you are going to take today” followed by a struggle to figure out how to do it the way we wanted to do it and still have the photos end up in the same place, tension ensued and digital paralysis once again set it. I sent myself an email task to “spend an hour with the fucking photos on Dropbox” this weekend which I’ll probably end up avoiding dealing with due to digital paralysis.

Yesterday, my friend Dov Seidman wrote a great article in Fast Company titled Why There’s More To Taking A Break Than Just Sitting There. It’s worth a long, slow read in the context of reacting to being overwhelmed digitally as well as in the general intense pace of life today.

As I sat and thumbed through some of the beautiful photo books that Artifact Uprising creates, I could feel my brain slowing down and being less jangly as I settled into observing and interacting with something not-digital. Try it this weekend, and ponder it while you are taking a break. Pause, and explore why you are pausing, how it feels, and what you are doing about it. And see if it impacts your digital paralysis when you end the pause and go back to the computer.

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