Startup Fundraising According to Paul Graham

by Ben Yoskovitz

Paul Graham is well-known in the startup world for his past successes and most recently, the launch of Y Combinator. Y Combinator continues to garner a ton of attention, from a combination of the sheer volume in startups being launched through the program, the successful exits, and the way in which they’re shaking up the venture capital industry.

I’m a big fan of Y Combinator. I wish I could have gone through the experience. From the outside looking in, I see an insanely talented and dedicated group of people running the operation, who are working with a slew of bright, young, hungry entrepreneurs. I’ve met several Y Combinator folks and have been impressed with all of them.

I think Canada needs a similar model, although for a whole host of reasons, it can’t be quite the same. But that’s a topic of discussion for another time.

Paul Graham recently published his Fundraising Survival Guide, and I wanted to take a few moments to go through some of his key points and add my own thoughts and experiences to the mix.

  1. Fundraising is brutal. That’s Paul’s first point, and he’s absolutely correct. He goes on to explain his reasons, but I think one of the biggest problems with raising capital is that no one teaches you how to do it. And if you don’t know what you’re doing, you’ll get eaten alive. Obviously, Y Combinator and other similar early stage “incubators” are helping with the education process, but they can’t reach the real masses of people trying to raise money.

    I’ve written quite a bit on the challenges of raising money, but reading about it and actually going out there and doing it are two very different things. Having said that, here are some starter points for you:

  2. There are no secrets. Paul Graham points out that, “Startup investors all know one another, and (though they hate to admit it) the biggest factor in their opinion of you is the opinion of other investors.”

    You would think that all venture capitalists would hoard opportunities that come in and not share them, but that’s definitely not the case. They have to speak amongst one another for a variety of reasons, and of course, they realize they can’t own the relationship — if you’re speaking to one VC, you’re almost certainly talking to others (if you’re not that’s another problem).

  3. Consulting is the only option you can count on. Paul talks about the fact that bootstrapping is hard. Very true. He then goes on to say that consulting is the only option for bootstrapping if you don’t want to (or can’t) raise capital. That’s true, but it’s extremely hard to do (which he points out as well). The fact is I have rarely met any founders who were able to successfully run multiple businesses, and even fewer (if any!) who could use one business to fund another. It’s just too hard. If you’re running a business that generates modest cash, but you’re trying to start something new, you will eventually have to make a choice between the two.
  4. Low expectations. Paul points out that you should have low expectations dealing with investors, because the fact is you will be rejected way more than you’re accepted. If you let the rejection get to you, you’re in big trouble.

    He’s 100% right. It still sucks that it has to work this way though. And the worst part about it is that it creates an us vs. them attitude. Even when you do raise money, you may be so soured by the experience that you’re already drawing lines in the sand against the people who are investing (let alone those that didn’t!)

    Paul talks later on about how to respond to a VC when they ask, “How much are you trying to raise?” He suggests that you don’t provide a definitive number, but instead offer different scenarios. Each of those scenarios is painted so that you’ll succeed, regardless of the actual amount of money you raise. That’s extremely tough to do, because the pressure will be to given VCs an amount. But nevertheless, having those various strategies is a way of buoying yourself against rejection. If you feel you can execute on $50,000 for a year (albeit much more slowly than $1M in a year), you can defend yourself emotionally against the inevitable rejection. If you feel like you can only succeed if you raise $1M from VCs (in the next 20 minutes no less…) you’re in big trouble.

  5. Keep working on your startup. This is obvious, but as Paul points out, it’s harder to do than it looks. I’ve been told on numerous occasions that a CEO will spend 60-70% of his time raising capital. That’s a lot of time…I’ve never measured that myself, but anecdotally that sounds about right. Scary, but true.

Raising money is hard.

That’s one of the key take-home messages in Paul Graham’s essay. I think it should go further than that, because no first-time entrepreneur raising capital will really appreciate the words.

Raising money without really understanding the process is almost impossible

Y Combinator (and others like them) helps by providing a ton of education / training to its startup members. The rest of us … well … we’re not quite as lucky. You can’t rely on reading alone, although that helps. You need to sit in a room with experienced entrepreneurs and have them talk you through their experiences. You need them to critique your presentations. You need them to help you review term sheets. You need them to walk you through the roadblocks and minefields of the process.

Raising money for the first time alone is almost impossible.

I’m not suggesting you hire consultants to help you, because that’s a minefield in and of itself. I’ve always been wary of consultants stepping in to help in the process, especially when they charge money … after all, you don’t have any, that’s why you’re raising it in the first place!

First-time entrepreneurs need active mentors and advisors who can walk them through the process. Heck, let’s call it what it is — hand-holding. There’s no shame in that and without it your likelihood of success is significantly lower.

August 18th, 2008
More in Startups
  • Wow a CEO spends 60-70% of his time fundraising? I expected it to be high, but I was expecting more in the range of 30%ish. Although I suppose really any time spent briefing people, evangelizing the product, etc could be considered as fundraising depending on how you categorize it.
  • Hey Ben,

    I may be a masochist, but I truly enjoy fundraising. I've been raising VC since 1999. Many of Paul's points are bang on, but you can get good at it (in fact, as you point out - you have no choice - you're either good at it or you don't get funded).

    The rejection sucks, but it is possible to become highly effective at raising VC$.

    I may put together my own version of a survival guide soon.

    Mark
  • @Mark: I think there are very few people who like raising money. Those that have done it a couple of times might feel empowered in the process (knowing what they know, and who they know), but I'm sure the people who actually enjoy it is very few.

    There are certainly aspects of it that I enjoy, and the learning process was an exceptional one ... and if I was starting something new now (or in the future) I would probably enjoy it more having gone through many of the growing / learning pains previously.

    Still, you're a rare breed :)
  • Jay
    Y Combinator along with other high-profile VC firms, have really captured the imagination in the UK. Dragon's Den is becomming a bit of a cult here.
  • @Sid - I found it hard to believe as well when I was first told this, but it seems to be the norm. Meetings are just such a huge time sink in terms of preparing, thinking, transportation, etc.

    Some companies, when possible, will dedicate one founder to raising money, while the other (often more technical) founder stays home and keeps the product moving forward.
  • The meetings take up a lot of time, but equally, if not more demanding is the preparation. From building out presentations, to figuring out what hockey stick revenue projections to put in, to figuring out how much you want, to deciding which investors to reach out, to networking, etc. etc. It all takes up a lot of time.

    And once you've raised capital, generally, you have to keep doing it.
  • Testing out the new Disqus comments implementation.
  • yeah dragon's den is the best show on tv in the UK. it's definitely the way to go, trying to get a businesss loan from the banks is becoming increasingly harder. it's a question whether you want to sacrifice a percentage of your start up but recieve mentoring/help along the way or just go solo and risk rejection from the bank.
  • I can't speak about Dragon's Den in the UK (having never watched it) but in general, I wouldn't recommend it as "the place to go for funding." In Canada I know that they've funded very few things, the terms are generally unfavorable and behind-the-scenes you get a lot less help than what's sold upfront.

    Dragon's Den is about entertainment. I think it's fun, but I don't think of it as anything more than that.
  • Have someone experienced in a company to work to the requirement imposed is crucial in this respect, as plan / proposal need to be follow up and refined along the process to get it through.
  • It happened I was reading about Paul Graham, very friendly explanation how to do fund raising. This is a very informative guide http://www.paulgraham.com/fundraising.html.

    It's true that "Raising more money just lets us do it faster". :)
  • Al
    Kudos to Paul and thank you for sharing his wisdom!
  • I studied financing briefly recently, and you are absolutely right about what you said. Financing is a difficult, frustrating process, but for the majority of companies, that needs to be done. I'm lucky I haven't needed to approach anyone for financing yet, although I may have to at some point.

    I liked the "What Your Brain Looks Like on Funding" post.
  • Thanks Rick. To-date the "What Your Brain Looks Like on Funding" post is one of my favorites. And it's so, so, so true...
  • If you want to do it right I agree with Kristina. Must READ about Paul Graham Folks. He is a mastermind in my opinion.
  • James
    You mentioned that first-time entrepreneurs really need mentors to guide them through the snake pit of fund raising. Do you have any suggestions on good places for a new startup to seek a mentor?

    I know about Y Combintor and similar incubators but not everyone has the option for that experience.
  • James - this is a big problem, and something that I do think groups like Y Combinator and others help address. But for the larger population of startups there are no immediate answers. I have some ideas on what can be done within individual communities to create mentor-like opportunities, but that's for another day (and a longer post).
  • @James - one avenue for you to check out is regional incubators. I work in a technology incubator that is part of a regional collaborative of incubators (http://neoinc.org). We provide no-cost coaching and mentoring to high-tech startups and have good relationships with our regional funders. Generally, if we refer an entrepreneur to an angel group or VC, that entrepreneur will get a little extra attention due to our relationships.

    There are no guarnatees of course, but this could be a good avenue for you. Especially if your region's incubators, like ours, offers services at no cost.
  • Joe
    The last thing I would ever want to think about or spend time doing is raising funds for a start-up business. I did work for a start-up and the CEO did spend most of his time on the phone or in meetings with potential investors. Eventually he rarely, if ever, got involved in the shaping and direction of the product and his creativity was sorely missed.
  • Joe - What happened to the company?

    This is part of the reality of being CEO of a funded startup, and balancing your time between raising capital and managing the rest of the business, including product development, is a huge challenge.
  • Joe
    The company went under. The company was in the gift card business and was attempting to add an innovation to the industry. It looked pretty promising except that they had a faulty distribution system. The idea behind the card was that when you bought it you got two DVDs that you could pick from the company's website. Things were fine there, but when it came time for customers to pick DVDs they could choose titles that were physically in different places. This raised the price of shipping and made the product not very profitable.

    I think the company was around for a few years in different stages until it tried to launch the product nation wide around Christmas time a few years ago. It tanked shortly after that.
  • Interesting. Live and learn, that's the best we can do...thanks for sticking around and keeping the discussion going.
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