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16 Pitching Mistakes and How to Fix Them

An article we liked from Thought Leader Jason Lemkin at SaaStr:

16 Rookie Errors Founders Make Pitching to VCs — And Passing the “20 Minute” Test

The world of venture has changed so much in the last 2 years.

Startup PitchFirst, pitches moved to Zoom. Then, SaaS VC interest exploded. And now, it’s slowed down again. Given all the changes, I thought it would be worth refreshing this classic SaaStr post on things it’s easy to get wrong when pitching investors.

Pitching VCs is like anything. You’ll get better at it over time. Later, you’ll even get great at it. Once you know how it works, it’s not even that hard to knock it out of the park.

But until then, so many founders make unforced errors. Rookie errors. Here are 16 that you can easily avoid / fix right now today. Before your next pitch:

  • Cold emails work. But they need to be truly awesome. Every part of them. At the recent New New in Venture SaaStr event, we asked many of the top VCs, from Aileen Lee to Keith Rabois and more, if they read cold emails. They almost all say that they do, and in fact read almost all of them. So don’t listen to anyone that tells you cold emails don’t work. VCs are in sales themselves, and they are hunting for that next great deal. But a cold email especially has to be awesome. The email subject line. The email itself. The deck. It has to stand alone. A cold email has to be so awesome, anyone would want to invest. Or at least instantly want to learn more. More here.

  • Being cagey with answers. Just answer the question. How much are you raising? Where are you in the process? Being direct (and honest) builds trust. With VCs, you want to build trust quickly, if you can. Especially over Zooms.

  • Bringing the wrong people with you. Do not bring “consultants” to a VC pitch. Do not bring anyone with you that isn’t part of the senior team. As soon as you bring a “consultant” with you — most folks are out. It makes the team look weak and incomplete.

  • Not sending the deck ahead of time. Just send it. You are wasting both a lot of time, and an opportunity, by not letting VCs do basically homework ahead of time. Make it easy on them. And send it as a PDF. Generally, don’t send it to through some “service”. Build trust. Make it easy. If you are the one selling, don’t put hurdles in front of getting a check. Remove objections. Send the deck. Even if they might email it to someone you’d prefer they didn’t.

  • Not doing at least basic homework on the VC firm. You should know their other investments in the space. VCs may be fungible, but no one wants to feel that way. Share why your start-up may be of interest to them based on other investments. That’s, again, Sales 101. And you are selling shares of stock. It’s still sales.

  • Spending more than 2 slides on “the industry”. Do not do this, unless asked. Assume VCs understand what is “happening in the cloud”. This not only is a waste of precious time … I’ll fade away.

  • Going in too strong. If you have 2 signed term sheets, for sure, go in strong. It saves everyone time. But being too aggressive, too take-it-or-leave-it, if you don’t have options — is a big mistake. Creating urgency is part of sales, for sure. But you don’t want to push it too hard. When in doubt, just be...

Read the rest of this article at

Thanks for this article excerpt to Jason Lemkin at SaaStr.

Photo by RODNAE Productions

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