The “Men are from Mars, Women are from Venus” analogy might not be that far off when comparing venture capitalists and entrepreneurs. I spent four years as a VC, and I’ve been the CEO of an e-commerce startup for the last two years, so in yesterday’s opening piece, I gave some pointers to VCs, and particularly associates, on how to better work with entrepreneurs. Today, I’m going to give some advice to entrepreneurs based on my personal experience on how to work smarter with VCs.

• It’s a numbers game. Expect casualties. I’m not kidding. Preparing to reach out to VCs, particularly if it’s your first time, is not unlike the preparation one does when preparing for battle (and this comes from a former air force pilot). You should prepare for a process that can take six or nine months or even a year, depending on the market conditions. You need to prepare for people with little knowledge of your technology or market who are comfortable telling you that there is no market for your technology.

  With VCs investing in very few companies, a successful entrepreneur has about a 2% chance of securing funding. This means that if you had a good meeting, the chances have just gone up to 4%. If you had a mediocre meeting, the chances have gone down to zero.

  Therefore, my recommendation for a first time entrepreneur is to meet with as many (tens) VCs as possible so that according to the numbers and of course, the quality of your offering, you can potentially get to the term sheet level with two VCs.
  I’m not writing this to discourage anybody. The rewards are sweet when striking an investment and ultimately, a partnership with a VC who can help you take your company to the next level, but there are many obstacles in this path, and every entrepreneur should understand the difficulty and frustration of this process.

• Develop a VC pitching strategy. Because of the challenges in securing VC funding, I strongly recommend that entrepreneurs develop a strategy which includes casting a very wide net of VCs to contact. You should divide perspective VCs according to key parameters such as investment history, industry focus, relevance of portfolio / connections (to your needs), potential conflict of interests and geographic location. Then rank the VCs according to your key criteria.

  I’d recommend beginning the VC outreach process with the lower ranked VCs who are also less likely to invest in your company, so that you can get some practice under your belt, and if you make a mistake, it won’t be critical.

• You need to play your cards right. The VC community is pretty small and close knit, so it’s likely that most of the VCs with whom you’ll meet will know each other. And like most communities, the VC community has its patterns of action. Given the inherent risk involved in VC investment, VCs like to know who else is considering investing in your company because they too tend to follow a herd mentality. If you can somehow covey the feeling that you are sought after by many VCs, it could definitely help you.

  Also, if you are negotiating with several VCs, they may try to communicate between themselves in order to consider investing together (split the investment between them). Having two VCs that you’re negotiating with join forces can hurt your negotiating power. It is much better to keep both horses competing against each other in the race for as long as you can (term sheet). Divide and conquer. Once they join forces your valuation goes down.

  Therefore, until you’re at the term sheet stage, it’s best not to disclose to other VCs the names of the VCs with whom you’re talking.

• Don’t seek funding under pressure. As I noted above, the fundraising process can take a long time, therefore it’s important to begin early, and not when you’re under pressure to raise funding. VCs will sense this pressure, and will use it as leverage in order to extract better deal terms. How does the VC saying go: “you should raise money when you can and not when you need it”?

VCs can be tremendous partners that enable a business to soar. But just as more than 50% of marriages end in divorce despite the best intentions, given the risk inherent in venture capital investment coupled with the 10% success rate of investing in start-ups, there are many potential obstacles that await the first (or even) second time entrepreneur reaching out to VCs.

Tomer Tzach is the CEO of an online marketing company DPlace Marketing, which operates Zoara.