I want to hit four of these most common mistakes so you can simply skip them! I promise you, I’ve made them all and there’s really no reason to go back there. Most importantly, once you get your foot in the door for an investor meeting, you want to keep it going. The four common mistakes I’m going to address are assumptions, making promises you won’t keep, talking too much and looking desperate.

Today we’re talking ASSUMPTIONS. The assumptions we make can go over the top and they can be so obvious, but we do it all the time. We’re not supposed to walk around society and profile, make assumptions about somebody – it’s that “don’t read a book by its cover” thing. As we’re going through our investor conversations, we do that a lot. We make assumptions that can derail this conversation. It shows a lack of discipline on our part.


If I have someone in my office talking about an investment and I realize they are making assumptions about their market, what they know about me, how their product or service is going to be received by the market, or how they’re going to market, I’m going to have a lot of questions. For example, if I already have a relationship with this person and they bring me a complete business plan, I can tell that s/he has really thought through this and have asked enough questions to really know what they’re talking about. That shows me that they’re very, very disciplined and that they’re actually committed to not just a really cool idea that makes them feel good, but something that can actually be done. I can have confidence that they’re going to be able to see the road ahead and not make assumptions with my money.

You don’t want an investor saying, “Well, you made an assumption about something simple, I’d hate to see what you’d do with a lot of cash.”


It’s not just discipline. Discipline is so important to an investor to know that you’ve got the grit to push through. A lack of information is super, super scary. Your investor probably knows by experience that there are some cliffs out there, some huge holes, and some sinkholes that you’re going to get mired down in. That’s reality, that’s life. There’s nothing wrong with admitting to those things. The investment dollars are to help you get around or through those, but you have to know the information.

You have to have walked that path, looked down that path with a flashlight. Make sure that you can identify those huge holes for your investor and say, “Yes, I’ve done my homework. I know what’s out there that’s why I’m asking you for the investment. I’ve calculated it, I understand the risk, I understand the opportunity and I see how we can do this.” That’s good information. It’s a whole lot better than saying it’s going to be the easiest thing in the world. Everybody knows that there’s nothing that easy in business. Anybody who has investment experience knows there’s risks. It’s okay, you can calculate it, you can work through it many times. If somebody doesn’t understand that there are risks, that’s usually a huge red flag to investors. Good or bad things, risks or opportunities – you need to have information.


Making assumptions shows a lack of care. Care meaning “I’m thinking for the investor here.” So, if I’m making assumptions about the investor or about the market, it shows the general lack of care. You’re asking for someone to give you what they have worked long and hard for (which has probably taken them decades) to put in the bank. They may be making money hand over fist and you think, “Hey, what’s an extra $100,000 or an extra $1,000,000 to this person? They’re so rich, it doesn’t matter.” It does. They understand the value of a dollar, that’s why they have so many. They understand how to get them and how to keep them.

Not making assumptions shows the investor that you truly do care about them and their investment because they do really want that money back. Show them you care about them enough to care about their money and to try to put it back very safely in their hands in pretty short order.