To begin, I have nothing against someone trying to start a company. And I love the fact that people are doing whatever it takes to make a living, or go for the gold, or both. But I won’t stop saying there are too many startups out there – so what’s the problem with too many startups? In fact, I don’t have an overall problem with that – again, I love the fact that many people are looking towards entrepreneurism to support themselves rather than finding a job (or the lack of finding a job in today’s jobs environment). I may talk about investors having too many to choose from, or the growth of competition stifling the ability for anyone to get big, but in general, I don’t have any issues with there being as many startups as there wants or needs to be.
My issue with the proliferation of startups boils down to 2 problems in dire need of solutions. Here they are:
Entrepreneurs are to the rest of the workforce, as Navy Seals are to the rest of the sailors in the Navy
In meeting with many entrepreneurs, I find that many lack a lot of the crucial characteristics of really making it as an entrepeneur. Everybody wants the good outcomes, but they are unwilling or lack the ability to gut through the bad parts. They lack the essential personality traits, like adaptability, able to deal with chaos, a never quit attitude, the ability to keep going no matter what even if it means their lifestyle is threatened. Or they have some notion of what it takes to build a company from scratch – maybe they took a seminar or read some books – but they did not actually take the time to work in a startup or build a business from scratch with someone more experienced to see what it is like and learn (by the way, one of those things they may learn is that they are not cut out to be entrepreneurs!). They all want to be entrepreneurs, but for some reason do not have the right characteristics or training.
This where I liken entrepreneurs to Navy Seals. We’ve probably all read about the crazy training that Navy Seals go through. According to Wikipedia’s Navy Seal page, the drop out rate is over 90%. And that’s after being selected from the normal soldier ranks for having the *potential* for becoming a Navy Seal. Not everyone can become a Navy Seal and their training is designed to weed out those who lack the essential traits that every Navy Seal must exhibit or else they put their mission and their lives in danger.
Entrepreneurs experience of their job is exponentially more intense than that of someone who has a normal day to day job. Like Navy Seals, not everyone is cut out to be an entrepeneur. But yet we set 1000s of people each year off thinking that they can become entrepreneurs.
We desperately need some better training systems and systems to help people determine whether they have the right personality make-up to be great entrepreneurs. What we have today is not enough. Book learning at college is not enough, and neither is a day long seminar.
Perhaps there are those of us who would say that setting them off into the real world building companies is the right way to go. Yes that may be true, but I would love to find a way to do it that does not require investors to put up their hard earned capital just so people can learn how to do it better, or learn that they weren’t cut out to be entrepreneurs in the first place.
We desperately need a way to fund startups that become small to medium sized businesses
Suppose you find a way to become a Navy Seal like entrepeneur or something close, and you work on an idea that seemed awesome at the start, but resulted in something less so. Instead of generating 10os of millions of dollars a year, it only generates a few 100K/year, or maybe millions.
At that level of progress and revenue, the company is doing great. It is generating money, paying real people to work for them so that they can support their families, and outputting useful products and services to others who need them.
For the record, I LOVE THIS. Our economy is in shambles and we need more businesses that simply employ more people. If you walk down the streets of Palo Alto, you see so many small shops that are now closed; so many For Lease signs even in a place like Palo Alto. Our country needs to fix this. The banks aren’t helping and new business creation requires other avenues for funding.
These companies don’t need to IPO, they don’t need to be acquired. They have great reasons to exist in their current state forever and generate enough money to support all their workers and the products and services they provide.
The problem is that we are funding startups like they all are going to IPO or get acquired for tons of money. We are not accounting for the case where the business levels out at a much lower place where IPO is not possible, and the likelihood of M&A is also very low. If a startup reaches a much lower place, we investors’ money is essentially trapped within the company; the company has no real way of repaying the investors unless they are making a lot of cash.
We often meet startups which are really cool and interesting, but when we look at the team, product, vision, and the macro factors, we sometimes can tell pretty early that this company is heading towards small business status. Sometimes the startup is cool enough for us to really want to put money in but cannot simply because we do not know how to get our money back, or make money when the deal is structured like a traditional startup financing and we are trying to make money from equity ownership. So if something smells like it won’t get big, often we won’t invest simply because of that.
Having said that, and despite the fact that we investors think we know everything (HA!), we really sometimes don’t know if a startup will end up as a small business or grow to IPO or M&A greatness. But I would argue that the immense proliferation of startups makes it highly unlikely probability wise that someone you meet will get huge; on the other hand, the probability that they will make it to some smaller state of revenue generation is much much higher.
Thus, it is my belief that our ecosystem desperately needs some way of financing startups that takes into account success at IPO/M&A greatness or success as a sustainable, smaller, revenue generating business. If we have this, then we should be more comfortable investing in more startups since we have greater comfort that we can get our money back or even make some money on our investment, versus seeing it essentially static within a company where we can never extract it.

I had the pleasure of meeting up with Oren Jacob, formerly of Pixar, now CEO of his own startup, and fellow 500startups mentor. The valley is filled with interesting individuals who have done some amazing things, and I always try to seek them out to hear a little about what they’ve done, assuming they have the time or openness to meet up with a total cold call!
We spoke about a lot of things but one thing we talked about encouraged me to get going on this post, which was about becoming an Entrepreneur In Residence, or EIR at a venture fund. Oren related to me how that, before starting his startup, that he went through an interesting process to become an EIR. My conversation with him allowed me to fill in some needed information about what I had already observed with EIRs. Also, I thought that this would be a perfect follow on to a recent post by Rob Go of Nextview Ventures titled So You Want to be a VC… and my resultant post The Path to Becoming a VC. After all, becoming an EIR is yet another way to get hired by a venture fund right?
What is an EIR?
First, what does that E stand for? I have seen E to stand for Entrepreneur, which seems the most popular. However, I have seen E stand for Executive (ie. “Executive in Residence”) and also the E has turned to D, standing for Designer (ie. “Designer in Residence” – see Jason Putorti who is most likely the person who became the first ever DIR at Bessemer). This does suggest some different functions that these folks do. So let’s discuss them first as xIRs, where x can equal any of the 3 meanings.
What does an xIR do?
There are many things that a venture fund might expect an xIR to do:
1. Discover/experiment/develop some next big idea for a startup – You are given an office space, phone, internet, maybe even a computer and then you spend time thinking up new business ideas. You then are given some time to work on them, and hopefully one of those develops into something that the venture fund will invest in.
2. You park until you find your next gig – Venture funds like to have smart people around. You might not have any real expectations although there may be some underlying ones, like they hope that you might join one of their existing portfolio companies and leverage your talent. So you becoming an xIR may actually be a recruiting tool. Or not – you might find a job elsewhere, but hopefully there was some goodwill generated for the venture fund by letting you park there for a while.
3. Due diligence help – Your areas of expertise may be of great help to the venture fund in helping to look at deals. You may be able to help them with due diligence and evaluating whether something is a great opportunity or not. .
4. Help their existing portfolio companies – You may be asked to go around to all their portfolio companies and help them if possible in your areas of expertise. I’ve known at least one Executive in Residence whose role was chiefly to help portfolio companies.
5. Sourcing more deal flow – It is well known that entrepreneurs hang out with other entrepreneurs. It may be hoped that you will bring some deal flow to the venture fund.
6. Any combination of the above.
What are the terms?
1. Compensation ranges from zero dollars to up to $250K/year.
2. Carry in the fund’s returns doesn’t seem to be something that is offered.
3. This arrangement can last from about 6 months to 1-2 years to until they let you go or as long as you need.
What else do you get?
1. You get to see the inner workings of a venture fund. Often you will get invited to sit in on deal meetings and board meetings.
2. Hang out in a posh Sand Hill Road office, or hopefully still posh but in a different location.
3. Get an office, phone, maybe computer in addition to pay. You will probably get business cards which improves your notoriety.
4. You get to attend firm events and parties, perhaps even speaking engagements.
How does the process start?
Venture funds are a highly relationship driven business (see Christine Tsai’s comment and my reply on my Path to Becoming a VC post). The probability of you getting an EIR job without knowing the VC beforehand is pretty low. So getting to know some folks in venture funds makes the process a lot easier than if you didn’t know any. They will want to have the most confidence that you can be valuable to the fund. Knowing you beforehand helps with that.
Part of knowing you is about what you have done, how well you have done it, and your expertise. I have never heard of someone coming out of college to become an EIR. Perhaps it has happened but I think very rarely. You don’t have enough experience or a track record behind you yet. I could see it happening from a Ph.D program where someone may have been working on something while at school and then is ready to commercialize it. More likely, you will be known to the venture fund through a portfolio company or through your notoriety in another company.
If you get noticed by a venture fund, you’ll probably get invited to come in for an interview. Most likely these positions aren’t advertised so venture funds tend to be able to choose the candidates; it would be a rare circumstance if you were able to interview for EIR positions at multiple venture funds.
How do you make a decision?
There are the usual considerations like compensation and health insurance, the poshness of the office, the reputation of the fund as you leverage it, and fringe benefits like free food in their fridge. However, the most important considerations are:
1. You like the people you will be working with, and they like you. Relationship is everything. If they offer you a job, obviously they like you, but do you like them?
2. The expectations and goals of the venture fund in your role as EIR match yours. If you are thinking that you just want to park somewhere until your next gig shows up and the venture fund is expecting you to build something so they can fund it, that’s bad! You could leave the fund with them thinking you’re not able to execute or are just a slacker. Make sure the reasons for you becoming an EIR there match theirs as closely as possible.
By the way, it does not appear that becoming an EIR is a good way to becoming an investor. Yes you’ll be working for a venture fund and see a lot of the inner workings of one; however, the expectation is not to train you to become an investor but rather to work on startups and startup ideas. That does not mean that you could not jump on the path to becoming a VC later on (see my post, 3 effective ways to jumping on the path, especially path 3).

Rob Go of NextView Ventures just wrote a great post: So You Want to be a VC? where he describes what it’s like to be a VC, to the many people who tell him they want to get into VC.
I thought I’d repost and expand on part of my comment there as I thought it was complementary to his post. So how does one get on the path to becoming a VC?
Getting a job at a venture fund is one way to start your path to becoming a VC. But trying to work your way up through the ranks of a venture fund is tough and there aren’t that many jobs to go around.
Becoming an associate or principal is a great way to get introduced to the inner workings of a venture fund. However, your path to becoming a partner or someone of decision making power is very difficult – after all, most funds require their current partners to work on them for many years, including maintaining their control (ie. “we investors bet on this person’s skill for making great investments”) and incentives (ie. carry on the investments). It’s not likely that a partner is willing to give up any of that on their current funds, or even on future funds that they raise. More than likely you will have to work your way to becoming part of a team that raises a new fund in order for you to start gaining some independence and the incentives that come with it.
Some of the more effective ways are:
1) First angel invest and then raise money. In true startup fashion, you put up your own resources to make the bet that you’re on to something (your own skill as investor). Others notice you and then invest in you to invest their money. Putting up your own money, investing it, and making money proves more than anything you can do this work. Of course, losing it all is also in the cards so make sure this is not a substantial part of whatever wealth you have.
2) Get wealthy people to know and trust you. Investing is very much a trust based business. Who do you trust with your money? If you have connections and relationships with wealthy individuals and build their trust with respect to investing their money responsibly and with integrity, you could begin your venture career that way.
3) Start as an operator. The four big places I see this work are: CEO of a company, Corp Dev person, entrepreneur with big exit, and engineer at a “celebrity” firm like Google or FB. These positions can give you credibility to raise your own fund or get hired by an existing firm. More likely, the $ outcome results in you being able to start the path with step 1 above.
But given the lack of available positions, and the lessened ability to woo wealthy potential limited partners in today’s competitive and economic environment, you still have to exhibit something *really* special. There are too many people out there who are competing for that attention and their cash, and you really have to do better than “I want to become a VC”. More than ever, you have to answer “I am the best up and coming VC because….”
Also you’re going to have to let go of any arrogance about how great you are right now. I learned this back in 2006 when I tried to raise my own venture fund. I was just out of Yahoo and thought I had enough skills to pick companies and make money through investing in them. I had 9 years of work experience at Yahoo, 1.5 at frogdesign, and 3.5 at Apple before that, and a Stanford degree to boot. How could anyone NOT give me money to invest?
However, the investor community all said that my partner and I had great skills as operators, but they had no confidence in us to manage investments. After 4 months of raising, I got frustrated with hearing the same message over and over again. I stopped fund raising, set aside some personal funds and started angel investing to build up some investing track record. After 5 years of doing that, I realized I didn’t know diddly about venture investing back then and only now I’m starting to build some confidence that I know a little about what I’m doing. Through time and on multiple fronts, I’ve built some credibility as an investor in world full of investors who have a lot more celebrity and notoriety than I do (this alone is probably worth a post in itself). Thankfully, earlier this year, Launch Capital has taken a chance on me and I can begin learning more as an investor of someone elses money besides my own.
So even though I had that wonderful resume and education, about 14 years of work and a BS and MS from top schools, it has taken me 5 more years to *begin* to learn about a business I really knew nothing about, even though I thought I knew.
In the comment I left on Rob’s post, I mentioned talking people out of becoming a VC. I talk to them about my journey and all the really hard parts of the business underneath all the glamour and press. After I tell them all that, I look them in the eye and see what their reaction is, my intuition perking up to detect any sign of understanding or lack thereof. It’s usually at this point where I can see if they will *really* give it go and stick with it, or just quit in frustration because they couldn’t raise a fund fast enough.
Looking back on my path, it was a LOT harder and took a lot more time to build up to becoming a VC than I thought. There will always be people who happen to fall into it via luck or circumstance; awesome for them but they are definitely in the minority. Most of us have to spend a lot of time working at it AND proving that we actually can do this, and it will take a lot longer than you think.