Pitching – it’s an art and a science, a love and a hate, an up and a down (wait, what? get on with it? oh, okay, sorry)…
I spent most of the past 20 years on the sell-side of things, whether to VCs, partners, customers, etc. I learned a lot. As I near my 1-year anniversary at CNET/CBS, I’m getting pitched a lot. And I’m seeing startup after startup making the same mistakes. So I wanted to reflect on and share some of the experiences I’ve had being on the “other side” of the pitch.
So, to my friends and colleagues at startups, in no particular order, here are thoughts, tips, and suggestions on how you can get better results from your efforts:
- Know. Your. Target.
We had a startup in here the other day who clearly had not researched CNET. In fact, I’d wager they hadn’t even visited the site for 5 minutes. So we wasted at least 1/4 of the time with their founder taking us down utterly irrelevant paths. If you cannot tell me why you are a fit for my needs, you are wasting both of our time. - Learn the basics of how my business works
Same startup as above, literally had no idea how we make money. No idea. It’s fine if you don’t know all the nuances of my business, but at least have a rough guess. If unclear, then ask me via email before you show up, so you are ready to fit by the time we are chatting. - Understand our time, use it well
You have 30 minutes (occasionally 60) to get me hooked on whatever you’ve got. And there’s decent odds that, no matter how much I philosophically hate being late for things, I may be showing up late (apologies in advance). So you should come into the meeting knowing exactly how we’ll spend that time, what you hope to get out of it, what you hope I get out of it, etc. Granted this should be de rigeur for all meetings, but I’d recommend getting it to perfection before you show up. If we’re 8 minutes into our time and I still don’t know what you do, at all, it ain’t good. - Don’t re-use your fundraising pitch/story
I understand that having so-and-so on your board is great when you hit Sand Hill Road. Or that your CTO collaborated with whatshername on that last venture of theirs. But that’s 100% utterly irrelevant to my business needs. Further, I don’t necessarily care that the market opportunity for you is unicorn-like. Fundraising and sales/BD are similar, in that you pitch, but different, in that our needs and motivation are not shared. Bottom line: drop the SV jargon when pitching business opportunities. 
Skip the Jargon; Use vocabulary that I’ll understand
And while we’re at it, think very carefully about the terminology you are using. The reality check is most business professionals are paying little-to-no attention on the nuances that impact startups, modern tech, or Silicon Valley trends. We also might not know all the acronyms related to your particular niche/industry. One of your key goals is that I can go tell your story the moment you leave my office. You want me going to my team/peers/boss explaining how much we’ll benefit because of you. So if you confuse/bewilder me with insider talk, rest assured I’ll leave the meeting confused and unable to share your vision.- Also, skip the “tech basics”
We had someone in a recent demo show us how QR codes worked. Literally pulled out their phone, took a picture, showed a website. Unless you are the QR app company, you don’t need to show us this (nor how email works, browsers, etc). Not only are you wasting your time, and effectively talking down to us, you are also creating additional risk in case something doesn’t work (because it’s a demo, something will not work). If I want to see the demo of the QR scan, I’ll ask for it. Again, don’t confuse this with not showing me your core benefits, just we can take for granted the basics of it. - Something won’t work. Be ready.
It’s awful, for both sides, when demos break. First, keep in mind that we want your demo to work out great. We want to be impressed with your tech/app/service. We might be skeptical, but are actually hoping you will help us save time/money/whatever. So if your demo craps out in the middle, that’s fine, but be instantly ready to go with either a slide/diagram/video or just even talking us through what would happen in a successful demo. - Don’t ask Mom if Dad says no!
Had someone come in, pitch, and I politely declined. A week later, one of my peers emails me about the same company. So now we’ve had oodles of wasted time, and you still are not a fit for my needs. Only now, I’m about 1000% less open to you coming back in in a few months with a new option/service. We may be a big company, but we do talk. You are welcome to ask me if I think a different department would be interested – because if I think so, I’d happily send you on that way. Remember, if you are truly solving our problems, we are truly interested in you. - Keep your videos short and/or email me videos separate to our meeting
I watched a founder push play on a YouTube demo of their tech. It was a 9 minute video. I lasted 90 seconds before I asked them to cut to the chase and email it to me later. Remember the part about using time wisely? Send me your 9 minute video to watch later, or share internally with other decision-makers. But use our in-person time for interactive discussion and to understand the opportunity. “Netflix and chill” doesn’t work out so well in the office. 
Don’t Multitask
While one of the founders was sharing the vision, I was listening to the cofounder clickety-clacking on their keyboard – and rest assured they were not taking notes. I don’t think I need to say any more on this one.- Most Importantly: Be a square peg in a square hole.
Every time I hear a startup founder complain about how they keep getting bounced around departments. While its fair that sometimes this is BigCo’s fault – it’s just as much your fault. What your lesson should be from the bouncing is “you are not fitting into their process” which can easily kill a great potential deal. Some products/technologies are easy and obvious fits. Some are not. It’s your job to make your solution an obvious fit.Easy tip here: the very first time someone bounces you, take 5 more minutes to understand the wider organization.It may well be that at company X its a marketing decision and at company Y its a product decision. But that’s a solvable problem. When I was running Dijit, it was “obvious” that TV companies could benefit from having audiences get automatic reminders to watch their shows. But it was far from obvious as to which department at each network was in charge of something like this. Social? Marketing? Reach? Audience Development? So we put in a process that had us uncover this information prior to any in-person meetings. No more bouncing.
I hope these are helpful to any startup trying to get traction – I know it’s hard. Remember to focus on the audience, share your passion, and hopefully great things will happen!