4-Day webinar with Penelope: Make money selling your ideas


This course includes four days of video sessions and email-based course materials. You can purchase this course for anytime, on-demand access. The cost is $195.  

Sign up now.

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.


23 replies
  1. lynn
    lynn says:

    The course will be Mon. Dec. 15 through Thurs. Dec. 18 at 8pm EST. It’s $195. But if you sign up before Dec. 21…

    oops. Did Melissa check this over before you blasted it?

    • Melissa
      Melissa says:

      Ack! Haha. She didn’t let me edit it first, obviously, but I’ll fix it right away. Thanks.


    • Penelope Trunk
      Penelope Trunk says:

      It’s actually pretty easy to close a $500 pitch.

      You find the people who can send you the $500 via PayPal. Then you think of what they need to buy – what will make them say, “Okay, here’s the money.” Then you write an email pitch. Then you do it 20 more times in one day. One of those pitches will work, and you’ll get the $500 that day.

      That’s a high-level version of what the webinar will teach you to do. This is literally how Cassie feeds her family, and it’s how I used to deal with my startups running out of money in between investor checks. I’d just find $500 online.

      When Melissa lived with me she used to say I’m a magnet for money. But actually I’m just very disciplined about teaching myself the survival skill of getting small amounts of money quickly.


      • Cassie
        Cassie says:

        I also want to add that INTPs typically have amazing skills that people would pay a ton of money for. The problem is that INTPs are terrible at selling themselves, because they need so much alone time to process their ideas.

        Learning how to pitch via email will help you sell yourself without having to talk to anyone. :)

        • Nur Costa
          Nur Costa says:

          I am an INFP, does that mean I am an awful self-seller?
          I wish I could afford this! I want to be a magnet for money too.

          I know this is not meaningful content, but it was so long since I last commented on your blog, Penelope. And I want to show you that I still read your content.

          • MBL
            MBL says:

            I hope that Cassie or PT answer this, but want to jump in and comment as an INFP.

            I am always able and willing to “sell” for someone else, if I deem them worthy. And do it as a matter of course since I feel obligated to try to support them. Like you, I also sometimes feel that I need to “justify” my comment if it doesn’t seem meaningful or potentially helpful to others.

            Below I noted how little the course costs (for me) if I break it down into a cost/week based upon how long I have been reading this blog. I did that in hopes that it might spur someone else to think in those terms and maybe throw some money PT’s way, thus exemplifying my willingness to “sell” for someone else. It all circles round…

            For the record, I always like reading your posts and hope to “see” you more often.

      • Dave
        Dave says:

        OK, for $145, you have sold me, just to understand what exactly an idea worth $500 looks like. I can’t imagine any idea being worth that much unless it includes some insight of how to actually make it happen. And who are these people on paypal who have that much money to throw around just to get an email response with something they hadn’t thought of already?
        In my experience, the idea is the easy part. It’s making it happen that is the tough part. Are there really people with lots of money to spend who just can’t come up with ideas on their own???

        • Dave
          Dave says:

          I should amend that to say that of course I can think of ideas worth $500, but that is like valuing my time…it is subjective without having the customer. There are probably ideas I think are obvious which might be worth something to someone else, but yes, I have no idea how you can get compensated just for sharing an idea. It seems like a fantasy, like people who consider themselves “inventors” when all they need to do is sell the amazing original idea to somebody else.
          In 1995, my friend and I were talking about how it would be really useful to create a website where people could post classified ads to sell their stuff. And technically…not so hard to design how it would work. The idea for ebay was obvious to a lot of people, but of course it was up to “doers” to actually make it happen. Similarly with Facebook…watching the movie at least, what he did at Harvard was sort of obvious; to scrape some websites and automate a localized version of “hot-or-not.” I have always felt these ideas were not the sale-able thing–it was the entrepreneurship to make it happen along with a fair amount of luck.
          I’ll sign up. If we could have pitched ebay to the right person in 1995…who knows?

  2. Vukani Nxumalo
    Vukani Nxumalo says:

    I know someone just as interesting as Cassie. I’ve always asked why she acts the ways she does. For some reason I think I now understand why. An interesting and look forward to discovering the ‘HOW TO’ part.

    To great ideas, and Cassie

    • MBL
      MBL says:

      Absolutely! And I’m doing my part, for once.

      I have thought about taking a course but nothing was applicable enough to get my INFP self to commit. And, of course, once the discounted deadline has passed, there is no way I would pay a higher price. And once the course is over, there is really no way I would pay the higher price for the recorded version over the live one. This is regardless of how valuable it might be to take the course even at the higher price.

      While I have no immediate need to apply this course, I went ahead and signed up. This way, even if I don’t participate in the live version, I still get the recorded version at the “sale” price. And even if I never watch it, I figure I have been reading this blog for 4 years and have only purchased her book. So $25 + $150 = $175 which is less than $.85/wk. Sounds like a bargain to me!

  3. Jay Cross
    Jay Cross says:

    This course sounds great! As someone with no connection to it, I want to point out another reason people should sign up.

    Some might be reading this post and thinking “I don’t want to BE in a position to desperately need $500. I want to build a business that puts money in my bank account 24/7!”

    (Similar to the Four Hour Workweek.)

    That’s a perfectly fine goal to aspire to, but you actually NEED to master the skill of pitching BEFORE you can ever do that.

    Making money on autopilot is essentially pitching at scale. Of course, you can only do at scale that which you’ve learned how to do manually.

    All of which is to say: if your eventual goal is to have a HUGE flow of money rolling in, I can think of no better starting point than learning how to close a $500 pitch when you desperately need to.

    The reverse also strikes me as true: if you CANNOT close a $500 pitch when you desperately need to, you probably wont ever build a high-income business either.

    Good luck with the course!

    • Cassie Boorn
      Cassie Boorn says:

      This is such a great question!

      Most people are either great at selling or great at a very specific skill. We will show you how to package the skills you already have in a way that sells.

      I can come up with ideas for almost any business, but I am incapable of activating almost all of them.

      This course will leave you with plenty of ideas on how you can package the skills you already have. Hope that helps!

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