Not everyone is a salesperson, but everyone has the ability to sell their dream. Gotham Gal talks about a game changer moment where she learned how to push back.

By Joanne Wilson (CEO, Gotham Gal Ventures)

Raising money sucks. It doesn’t matter what series you are at, it is just not something that is enjoyable.

I am invested in a few companies that are raising money right now. There is no doubt that money will be a game changer but more important they are businesses that will succeed. At what level?  Well that is always a crapshoot but they have each proven the model and understand how big they could each grow. With that being said, it still is not easy to get cash. You have to find someone who believes in the vision and actually is interested in that particular space.

I was on a call with one of the women I am invested in and we were discussing her first pitch. I told her straight out that raising money is all about sales. How can you connect with the person on the other side of the table. How can you own the conversation? How can you get across what needs to be said by answering their questions? I suggested to think about the pitch like you are talking to the media.  Sometimes the questions are irrelevant but the information in and around the questions are relevant. How do you answer that so the person asking the question gets the “aha?”

I told her a story that I thought was relevant. When I was working as an assistant buyer at Macy’s, the guy who ran the division was a hard-ass. Most of the buyers were women and they were all unhappy and miserable. He was not exactly a warm and fuzzy person but someone who was gruff and had zero tolerance for stupidity. Truth is, I could appreciate where he was coming from.

I was working for someone who got promoted and then a new person came in who I adored. She got promoted and I was left holding the bag. All the financials for the season were due. This was before computers. The spreadsheets were insanely long and by the time you finished working on them they had holes from erasure issues.

Keep in mind I was 22/23 years old. I did all the preparations and went into the office of the division head. He took a look at my spreadsheets, barely looked at me and tossed them back in my face. He said, these are not right, go back and do them again. OK. I went back to the office and reworked the numbers. Then I returned to his office, hanging at his door until he acknowledged me with the financials. He took a look at them and did the exact same thing to me that he did before. This time I did not take the financials and walk out the door. I looked at him and said I do not want to play this game. We can go back and forth all day but if you don’t show me what you want I am never going to get it right. Show me what to do and I will get it right and I can then move on to other things. He looked up from his desk and told me to sit down. He showed me what he was looking for. After that he treated me totally different. When he came to visit me after I got promoted he could not have been more proud of my accomplishments. By pushing back I won his respect. It was a total game changer.

Investors can be tough but they want to invest in someone who pushes back, who is so committed to their business that is oozes out of them and that they believe that you are the person who can execute on the vision. Not everyone is a sales person but the reality is when you raise money, you have to sell the dream.

This post originally appeared on Gotham Gal.

Was there a time you gained respect because you chose to push back?