Many founders say they learned the most from their first failed investment meeting. That's another way of saying they failed to prepare properly...

Here are four techniques I recommend people use to be sharp on pitch day that I have not seen elsewhere. 

In brief, they are - low stakes testing on your business pitch before you meet investors - it makes a huge difference to your knowledge, performance and confidence. Tell your story with purpose - to inspire emotional connection. Profile your target investor, to improve relevance and stickiness; and finally, build your reputation - investors don't invest in strangers.

1. Low Stakes Testing

Most advice says 'know your numbers' or 'rehearse your pitch'. That's fine - but you'll do better if you expose yourself to multiple low-stakes mini-tests.

Even before you put pen to paper, sit opposite someone who you know will call 'B.S.' on you, and pitch them your business.

Brief them to ask investor-type questions and be as punchy as possible - make sure you get asked and have ready answers to your numbers, especially how much money you need, what you need it for, what returns you expect to provide, and when - as well as evidence of your success and the potential scope of the market.

Do this before you even put pen to paper. It will be uncomfortable - that’s part of the training. [Doing things before you're ready and taking slightly delayed feedback embeds learning - see more, below.]

2. Tell your story with purpose. 

Communicate clearly, concisely and with emotion. It inspires confidence and gains commitment. Find your answers to these three statements to help connect your audience to your business emotionally. The questions might be short - but it takes a lot of work to unpack and reassemble them. 

  • Who you are. [Your unique reason for being - your 'Why?' see the classic Simon Sinek video.] 
  • What you do. [Your 'What' should spring from your 'Why?' and be unique.] 
  • Why it matters? [Why your audience should care.]

Now, go back to another low-stakes test.

Pro-tip: Maximising benefit of low stakes testing 

Record these 'low stakes tests' on your mobile, and then run it through the 'closed captioning' process on YouTube or Teams [or just do speech to dictation on iPhone]. I prefer capturing the audio, too. This speeds up the note-taking process. 

Put yourself in a positive frame of mind and review the notes and the video. What felt good? What didn't? Where did you flub your story? 

Embarrassment prevents many from reviewing their own videos. Don't let it happen. See your awkwardness for what it is - a restraint on future growth, take two deep breaths and crack-on. 

The key questions to ask yourself in this review are 

  • What emotions would a stranger feel watching this? 
  • What key facts and stories would a stranger remember? 
  • What actions would they be recommended to take? 

Write down your answers to these questions, you will need them later.

3. Profile your target investor. 

There are some excellent guides for what to include in your investor decks. A fabulously useful list of past decks can be found here.

What I am saying is to consider each meeting as you would a conversation - if you’re not interested in the other party, you are a bore.

You'll be amazed at how much you can learn about each investor from their blogs, investments, thesis, and articles on sites such as and

How to best engage with this investor? You have another 3-tiered question to ask. What do you want this investor to FEEL, THINK and DO? 

Successful meetings only occur when the desired feelings, thoughts and actions land with the target customer. If your answers don’t match your thoughts from the end of your last low-stakes-test review, you still have work to do.

If possible - give this investor context to a trusted friend, and ask them to grill you - consider it just like the presidential debate prep you've seen on TV.

Many founders say they learn a lot from their first failed meeting. That's another way of saying they failed to prepare properly. Testing is the best way to mastery.

4. Build a reputation. 

Investors don't invest in strangers.

Speak to people you know, and the people they know. Find well-connected board members who can recommend you to investors. Speak to journalists. Find a superb PR firm to position well-placed articles for you - the whole point here is to walk into that investor room with a reputation. Don't be a stranger.

There's lots more I could say, of course, but these are the tips I haven't seen elsewhere and I hope are useful and practical. If you're looking for more practical tips, there are hundreds of exceptional resources out there for how to best prepare your content, I love the thoughtfulness of Paul Graham at Y-Combinator and Naval Ravikant at and Venturehacks.

Flagship has worked with many companies through Angel, VC, PE and IPO to help shape stories and connect with the right investors. 

If you think you might like to speak with us, get in touch via Twitter: @flagshipcons or