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You can judge if you are one of my good friends by whether or not I’ve fired you. Melissa, for example, is my really really good friend because I’ve fired her three times.

I fired Cassie twice. In fact, I was going to throw out that picture up top because it was from when she was working for me, but before I could even get to my delete button, she had reinstated herself as my favorite freelancer.

Cassie was supposed to be the salesperson for Quistic. There’s a corporate side of the company that sells to companies. And every day she would have a new idea for a pitch for something Quistic doesn’t do. And I was like FOCUS FOCUS FOCUS.

And she’d say her ideas are so good. And that just made me want to tell her more why her ideas would fail.

And then she’d go do them on her own. I’d be so annoyed that she was an employee at my company doing her own stuff on the side. And also I was frustrated that Cassie is great at pitching her ideas and her skills and terrible at pitching a company.

When I told her, she said, “You would do the same thing if you worked at someone else’s company.” And probably she is right. Which was even more annoying.

But the most annoying thing was that all her pitches worked. All the stuff I thought was nuts? She could sell it. People who I thought would never return her calls ended up sending her money. Emails I thought sounded like she was a sociopath were the pitches that people loved most.

Cassie doesn’t want to work at a company. She likes to have a million ideas. She likes to read a lot and think a lot. She wants to be home for her kids when she wants to and she wants to have a job when she wants to. The perfect life for her is getting paid for her ideas.

Now that I’ve done fifty bazillion coaching calls, I see that so many people who don’t like their jobs really just need to learn how to pitch. If you have skills, you can make extra money on the side by getting freelance gigs. If you can pitch yourself. And if you have tons of ideas, you can make tons of money by selling your ideas. But only if you can pitch yourself.

You need to understand where you can make money fastest, and how to go after people who will be clients. You need to create a system that can be really system-y if you are Melissa (INTJ) and really haphazard if you are Cassie (ENTP). Whatever system you come up with, though, should allow you to make money whenever you want to.

I’m not saying you will have a gazillion dollars. But actually most people who want to work for themselves or want to make some money on the side, or want flexible hours—all things you might want—you can get by learning to pitch.

This is a good time to tell you that I’m excellent at pitching. Part of the art of pitching is knowing where your audience is. My audience are VCs who don’t read my blog until they are fifteen minutes from meeting with me, so it seems safe to tell you that I get funding for my companies because I’m great at pitching, not because I’m great at running companies. In fact, I would love to just write pitches all the time, and it’s so annoying to me when I have to actually execute on the company once it’s funded.

That last paragraph is the anti-pitch. It’s like, please please do not fund me, I will make your life hell.

I told Cassie that she should write a guest post about pitching. But her post sucked. And here’s why. One of the things that makes Cassie great at pitching is that she doesn’t do stuff that isn’t going to make her money. I mean, she does. She has her son. Here is a picture of Cassie in a rare moment when she is not thinking about money. Well, actually, I’m sure she is thinking about money but she is not talking about it. She is being a model mom.

So although Cassie’s post sucked, I had to pay her for it anyway, because Cassie does not even wipe her butt without getting a retainer fee, so I figure, I’ll tell you the best stuff that she wrote. Which my editor hates, but whatever, here’s what Cassie wrote:

1. Pitch startup founders late at night

They always work insane hours and most executives are catching up on emails late at night. Also, it makes you look like a total hustler, which is like the biggest asset you can have when working with a startup.

2. Pitch Agencies and big companies early in the morning 

Big companies value people who are productive, efficient and work normal hours. So schedule all your pitches to go out at 8am, which makes you look like the type of person who wakes up early.

3. Think big and pitch high

The goal to making a ton of money freelancing is to think of really big ideas, and pitch really senior people at companies.  Senior executives are much more likely to respond to a pitch than other people in the company because the senior executive can write a check.

4. Sell multiple products 

Keep a list of people who told you “No,” and pitch them a new idea a few weeks later.

5. Don’t pretend to be something you are not

Most freelancers think they need a fancy website and corporate email address to get started.  Forget it. Send your pitches from your personal Gmail address.

Companies that hire you might ask you to pitch from their corporate email, but this will always reduce the numbers of replies. Why? Because people hate companies. But people love to hire interesting people who are building a business on their own terms. Its exciting (and cheaper) than hiring a huge company to help grow a business.

Be who you are. Tell them you are a one-man shop. Be focused and specific on what your specialty is.

There. That’s Cassie’s advice. Great advice, right? I was thinking I’d publish this and send everyone who needs to learn to pitch to this post. But then I realized that people need more help pitching. Here’s what everyone should know:

  • How to figure out if you should pitch ideas or a service or both.
  • How to find your most valuable skill.
  • How to determine the best people to pitch.
  • How to develop a slew of things to pitch instead of just one.
  • How to make $500 in a day when you are desperate for money.
  • How to pitch without picking up the phone.
  • How to escape your cubicle by learning to pitch.

So I am doing a course. With Cassie. It’ll be four days and by the end of the course you will have that crazy, “I can conquer the world” feeling that Cassie has because she can pitch to save the day any time she needs to.

Sign up now.

You will learn a lot about yourself. For example, what I learned about myself, just now, is that we each have to pitch in a way that’s true to us. I pitch in a story. Cassie pitches in a deluge of ideas and manic enthusiasm. We each need to be able to sell ourselves sometimes, even if it’s just selling an idea to a manager. And you always feel better selling when you are being true to yourself while you do it.

That’s what this course will teach you. Not to be Cassie, or me, but to be yourself. You should do that.