Be prepared. In the initial pitch you have a limited amount of time to cover all aspects of your deal. Highlight all essential elements, preferably in a structured sequence. The more solid the framework, the more it appeals to seasoned and professional investors. No need to re-invent the wheel, you can use a proven pitch structure. I personally always hawk pitches for covering the 4 pillars of their foundation. These are Team, Market, Financial and Corporate structure and governance. If you clearly 'miss' one of them – I'm OUT.
Raising funds for your company and managing the process is (almost) a full-time job. Help yourself and the prospective investors by professionalizing this. Use a streamlined flow of information through various stages of the due diligence. You must have a Data Room where you can direct, manage and interact with stakeholders. Just by raising the level of professionalism, you increase the chances of receiving funding. Money likes to follow professional, meticulous and prepared CEO's. Do not tell me, show me.
Even the concept of bringing in outside shareholders changes the game. Many entrepreneurs, especially start-ups, do not clearly understand the ongoing implications. It's okay to be inexperienced, but I will pass when I sense ignorance in this department. Because ultimately, my fate as a shareholder is directly related to the CEO's understanding of this. Please address this as it is important to (prospective) shareholders you're asking for funding.
Understand it's a numbers game for you. One of the largest miscalculations I've witnessed over and over again is that entrepreneurs overestimate the ability to raise funds. Lots of competition as we said earlier. No matter how GREAT your opportunity, you will be returned by at least 90% of the prospective investors. One of the best tips I can give to the CEO's I working with, is to generate a PIP-list (Professional Investor Prospect List). I recommend you spend a reasonable amount of time here. Categorize by geography, size, and their investment focus, stage. This becomes your central working document. Secondly, please budget for your fund raising round. Invest some dollars, even if you do not have many, in order to set yourself up for success in completing the financing. As a rule of thumb, budget for 2-3% upfront and 7-10% at the back end of your round (depending on the size of the round of course).
Avoid the Biggest Turn-Off pitfall. One of the hardest parts in Direct Investments is VALUATION. Countless entrepreneurs have (in my eyes) ridiculous expectations in regards to their company valuation. Often solidified by sharp 'hockey-stick' financial projections (always in the future). It's perfectly fine to be optimistic and somewhat opportunistic when evaluating your equity. As a professional investor, I always assess for risk-adjusted calculations. Your valuation should be a fair and realistic derivative from your plan and numbers. Not an arbitrary number.
Every beginning has an end. You're asking me to invest along with you to make your venture a success. Not the operational success is what matters to me, but a financial success. You're proposing to invest cash in, so at some point it must lead to cash back out (to me the investor). You're an entire pitch should absolutely revolve around that concept. Show me your plan HOW, WHO, WHEN and what's in it for the investor.
Not all investments are necessarily cash. In the priority cases I've been directly or indirectly involved with, the best investments are combinations of cash and other resources. Many investors, certainly our Inner Circle, have tremendous experience and connections. When put to work for your venture, you may be propelled forward further and better than any cash amount could ever do. Keep your eyes open and value each prospective investor for all possible resources, not just cash. And even if not every investor is able to donate beyond money, just the sheer proposition of you thinking about it, makes a great case for YOU as the ultimate entrepreneur I want to back.