When raising money from venture capitalists or angels, you’ll want to meet as many as possible. They won’t all invest, but each time you pitch, you get better. Each time you pitch, you get asked different questions, get different opinions and ideas. It’s worth it to pitch as many people as you can, as often as you can. Wil Schroter says it perfectly, pitch everyone, all the time.

Some questions will get asked over and over. And you’ll discover those patterns quickly enough and adjust your pitch accordingly. If you have a less-than-stellar answer to a question that gets asked once or twice, it’s not a big deal. But if your weaker answers are to the most common investor questions, you’ve got a problem.

With that in mind, here are some of the more common questions investors will ask:

1. So what’s your business all about? The wording of this question will change, but this is the classic “elevator pitch” question. Translation: “In the shortest amount of time possible, grab my interest by the proverbial you-know-whats.” Sell them quick, with something simple and powerful they can remember; and keep reiterating that message throughout your presentation.
2. What’s the barrier to entry for competition? For Web 2.0 startups this can be tough. The question comes from VCs and angels that might not be as familiar with the overall industry and the ease with which many web applications can be built. They’re looking for a real technological barrier that might not exist. Some answers that might help you skirt this topic: launching big, building a devoted community, key partnerships and/or customers (before launch), we’re cooler than everyone else (this won’t work.) None of these answers are great (for a host of reasons.)
3. What’s going to stop big monster company in your space from copying you? This is almost identical to Question #2 but it’s more commonly asked because there’s always competition. And, it’s usually from the “big bad wolf” company that’s got tons of money, lots of market share, a huge staff and years of experience.

   For starters, don’t say, “What competition? We don’t have any“. There’s always competition.

   Secondly, this is a tough question to answer. What is stopping “big bad wolf” company from copying you instantly and smashing you like a bug? Generally, you can argue:

   • We can move more quickly.
   • Big bad wolf is too busy managing what it’s doing to innovate.
   • They’ll acquire us rather than copy us (if you have examples, use them.)
4. Why are you raising the money you want to raise? The amount you’re asking for is critical. Make sure you’ve done your financial homework. Don’t tell them your numbers are conservative, just explain to them how you arrived at them.
5. How far does that money get you? Have a good answer to this question. Couch this in product and financial terms, i.e. “It gets us 6 months past launch, when we expect to be cash flow positive.” The best way to think about this is to calculate how long the money will last if you earn zero revenue. Count backwards by 4-6 months and that will tell you when you need to start the process of raising more money. If the money is only going to last you 4-6 months, you need to start looking for more money almost immediately (which isn’t a pleasant thought.)
6. Do you have any customers? Have you spoken to potential customers? Investors are looking for traction, or at least the inkling of traction. As soon as possible, try and get a few potential customers to say, “Sounds interesting.” You might even use them as references. This raises the comfort level for investors and helps answer the question, “What’s the market?”
7. What’s your marketing strategy? For early stage companies this is a very tough question. Chances are “just getting to freaking launch” is what you’re thinking, but that’s not good enough. And “launch big” is equally uninspiring. Think about presenting a timeline of events and customer acquisition numbers that you’re anticipating, tied to marketing. Throw in a variety of strategies that you’re going to do or researching. Marketing will be critical to your success, so you better plan for it sooner rather than later.
8. What are you coding in? Investors do want technical details. This is an easy question to answer at least (assuming you know!)
9. How are you handling the technological infrastructure for scaling? Like I said, investors want technical details. They want to know that you’ve thought about the behind-the-scenes technology to support your system. When you get on the front page of TechCrunch, will the server hold up? When customers are signing up faster than you can process their credit cards (don’t let that happen!), will the system stay running at a reasonable speed? The further you get along in the process with investors, the more technical details they’ll want.
10. What’s the team look like? What are your backgrounds? Investors want to know the backgrounds of the founders. If you’ve got people on staff, they’ll want to know who, why you hired those people, and who else (and how many) you need to bring on board. They’ll want to know how quickly you expect to grow the team over time as well.

Although there are common questions you’ll get from venture capitalists and angel investors, what’s more fascinating is that each investor will ask different questions. You can’t be prepared for every question, but even if you get new ones, the more comfortable you are pitching (because you’ve done it so many times), the better.