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  • Writer's pictureCreative Return


Updated: May 28, 2023

Oren Klaff is the best-selling author of Pitch Anything and Flip the Script, and a successful

entrepreneur and financier. Oren has raised hundreds of millions for companies and has strong opinions on how to do it correctly.

One topic of discussion is Casper Mattresses who’s go-public debut led to a $750+ million drop in valuation. They dropped from $1.1 billion to around $250 million in a few short months. Among many things, we dissect how Casper got to a billion-dollar private valuation and also why they reached their current public market cap.

Oren’s approach to capital raising will make you throw out everything you thought you knew about selling you and your business. He sheds light on why your sales, marketing, or even relationship-building skills aren’t your strongest tools. In fact, they may even hinder your ability to fundraise. His thinking around raising capital for big ideas is a paradigm shift. When you go into a pitch meeting, you need to know your audience while also demonstrating that you don’t need them.

Oren talks about why it’s important to provide investors with only the salient details they are looking for. This information is often not what you think it is. Oren says investors do not need a ‘story.’ In fact, Oren calls these details coloring book materials. Attracting capital is about confidence, traction, and having the market for your product – something Casper had and overplayed their confidence and cards.

The flow of capital rejects neediness, which is why a sales pitch approach falls short. We also dive into why you need ‘cheat codes’ for pitches, and the links between neuroscience and raising capital.



  • Learn more about Oren’s background and how he came to write Pitch Anything.

  • Why raising capital turns every other skillset you have on its head.

  • Plugging into capital markets helps capital flow to you rather than you selling for it.

  • Find out why having a long list of questions after a pitch is a problem.

  • What investors are writing in their Moleskin notebooks during pitches.

  • Each type of investor has a different cheat code, all based on a similar formula.

  • Why the goal is not to get an LOI, but rather to find an investor to close with.

  • How hiring an investment banker can help you raise capital correctly.

  • Oren’s take on Casper, what they did right, and where they ultimately fell short.

  • Bidding wars: Why they do and don’t happen and what it takes to create one.

  • The biggest and most common mistake Oren sees: Going with only one investor.

  • Ways to use ‘frames’ to communicate honestly to investors that you have other options.

  • Some takeaways from neuroscience that are applicable to raising capital.

  • Final words to bake into any pitch, and details about Oren’s books.

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