When Not To Nail Your Pitch

to a hammer everything looks like a nail

I’ve heard two stories in two days about entrepreneurs who pitched when they shouldn’t have. Part of the art of pitching is to know when to nail your pitch, and when not to pitch at all.

In the first instance, an entrepreneur was asked to speak on a panel at a technical conference. Instead of talking about the technology in general (blockchain in this case) as requested by the panel chair, the entrepreneur instead gave his fundraising pitch.

It was so unwelcome that the next day, the conference chair singled out that presentation as “unfortunate” to the entire conference audience.

Bridges burned, network disconnected.

In the second instance, a student entrepreneur was granted entry to a closed trade show on the condition that they wouldn’t pitch participants. But the head of the trade show just got word from one attendee that they’d been pitched via email. Now, no more students will be allowed to attend the show in the future.

Bridges burned, network disconnected.

Here are some other instances where giving the formal pitch is the wrong move:

  • You’ve scored a coffee meeting with a prospective mentor, and instead of being human, you roll right into your well practiced investor pitch.
  • You’ve scored a coffee meeting with a very experienced prospective investor, and instead of giving the elevator pitch and letting them ask questions, you roll right into your well practiced pitch uninvited.
  • You’re invited to speak at a conference on a particular topic (technical or otherwise), and instead of doing the extra work to address that topic, you just give your well practiced pitch.
  • While you’re in fundraising mode, you speak at a local chamber of commerce or Rotary meeting and you give the full investor pitch to an audience mixed with accredited investors and those who aren’t accredited.
  • You’ve been told specifically not to pitch. Defying etiquette isn’t being persistent, it’s showing low EQ.

The Full Pitch Is Just One Tool in The Toolbox

Despite the fact that you’ve worked hard on your pitch and you can do it easily now, it’s not always the right thing to do. In my Art of the Pitch talk, one slide emphasizes that the pitch is just one tool in the marketing toolbox.

The pitch itself will come in multiple sizes:

  • Elevator pitch (30-60 seconds)
  • Short pitch (3 minutes)
  • Investor pitch (10-15 minutes)
  • Due Diligence deck (many more slides)
  • Customer pitch
  • Prospective employee pitch

And you’ll need other tools besides the pitch for fundraising. Verbal tools include practiced answers to anticipated questions, thoughtful insights on important industry trends, stories about real customer problems, and lessons learned from interactions with industry thought leaders.

The key with all of these tools: know your audience. What do they want to hear?

An industry analyst that could help you gain visibility wants to hear your industry insights, not your pitch. A trade publication reporter may want to understand customer problems more than your pitch. And those same verbal tools can be helpful in fundraising. Depending on the specific context they might be much more effective than the formal investment pitch.

Pitch Perfect

When I was embedded in the a cappella singing world, more as a singer than as an entrepreneur, I was keenly aware of the importance of knowing your audience.

Don Gooding in high school quartet

As a young enthusiastic barbershop quartet singer, and then a college a cappella group singer, I was too often inclined to break into harmony in public with my fellow acappellists.

This was not always welcome or appropriate.

I don’t remember any particular incidences of cold stares while singing in harmony at an iHop or a McDonald’s. But I know that by the time I started leading groups, I was more aware of the need for restraint in public singing. That included ignoring requests from random people to sing, in surroundings that wouldn’t lend themselves to a good musical experience.

Good selling and good singing include the ability to read your audience and read the situation. What do they want to hear? Can you achieve your goals in your current environment? What are good options?

When Not To Nail Your Pitch

There’s a famous saying: to a hammer, everything looks like a nail.

Don’t be the hammer for whom every situation looks like an opportunity to nail your investor pitch.

Don Gooding

1 comment

  • I’ve often found that the best way for me to get high quality opportunities in life AND in fundraising is to leave the pitch deck and my laptop in my bag and rather ask for advice and GENUINELY accept and engage in feedback conversations. I am genuinely interested in growing my network, in learning from experienced people, and I offer updates to them to thank them for the feedback and share the progress I’ve made or action I took as a result. This kind of interaction teaches me a LOT and is a terrific way to get to know people and engage with them. It actually led me to my lead investor and chair of my board (thanks to an intro from you, Don!), and several of my investors. I highly recommend that. Secondly, I speak at a lot of conferences and events, and unless explicitly a pitch contest they are NEVER the time for a pitch deck. I find the softer I sell and more I share / educate / empower the better it works. People are there to learn and seek inspiration, not to be pitched. Love this piece, Don thanks for sharing!!

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