This Opportunity Comes Once in a Lifetime by Brian CalifanoSometimes you have to be careful what you wish for — and I mean this in the kindest of ways. A prime example of this is when entrepreneurs get an interested investor to meet and discuss a potential investment in their company.

No matter who it is, we always operate under one principle: you only get one chance to make a first impression. When it comes to money decisions, first impressions often decide whether the conversation moves forward — or ends before it truly even began.

Over the years, as both advocates for clients as well as due diligence preparers, Scott and I have identified a few common themes that can help ensure that an interested party chooses to become an equity investor. 

If they like you, they will find a way to fund you. Even though investors are in it for the money, of course, they also want to feel a human connection. Like most of us, they want to work with people who they admire, respect, or want to get to know better. It is during the pitch process that you can convey your story and how you came up with the idea for your business. Whether it’s rags-to-riches or a eureka moment, it is important to convey enthusiasm and allow your personality and personal/business values to shine through. 

Demonstrate that you’re coachable. When speaking with a potential investor, you need to demonstrate both a commitment to continuous learning as well as a sense of humility, irrespective of what you’ve accomplished to date. If you’re in the room with the investors, it’s because you’re smart enough — and your product is good enough — to get their attention. If you convey that you are just looking for money and not a true partner, then your pitch will quickly come to an end. When you’re pursuing an investor or business partner, you really need to communicate that you don’t know it all, and that with all your accomplishments, you are still striving to do better each and every day. It is by surrounding yourself with smart people and/or people who have access to helpful resources that will further strengthen your pitch to your potential investor. There’s a fine line between confidence and cockiness; yet it’s a line that needs to be acknowledged because nobody wants to work with a know-it-all who can’t listen and value alternative points of view.

Know Your Numbers: You don’t have to be a “numbers person” in order to demonstrate you understand your business. We’ve written a lot in previous posts about key performance indicators (KPIs). There are certain KPIs that you need to know such as sales, net profit, and gross margins; but, there are other KPIs that may be specific to your business or how you run your business that are just as valuable. It is those figures that you need to define and explain to the person in the room. Again, (a) what KPIs do you use to manage your business and why, and (b) what are the key drivers that indicate the health of your business? Being able to both understand what your consumer is looking for and communicating that understanding in the investor pitch meetings are fundamentally vital to raise the capital your company needs.

Prepare, prepare, prepare: In preparation for your meeting, you need to understand the common questions that are asked, but also prepare for questions that you may not have thought of before like: What drove you to start your business? or Where do you see yourself in five to ten years? Many of the questions may be very personal in nature. It’s also helpful to research the investor and what types of businesses they’ve already invested in. You want to convey that you analyze details and do not leave any stone unturned. 

Although each initial meeting with potential investors is never the same, these four areas of focus need to be addressed before you go into the room. The only way you’re going to have a chance for a second meeting is to make sure the first one is well-planned and well-executed. 

Take-away: If you’re not sure whether you’re fully prepared for your initial or subsequent meeting with potential investors, reach out to us at to receive a free diagnostic on how your business looks from the eyes of a potential investor.

Brian Califano & Scott MargolinBrian Califano

Scott Margolin

Co-founders & Managing Partners


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