The 12 Worst Train Wreck Meetings Between Startups And VCs You Will Ever Hear

Russian Train Derailment

Does public speaking make you sweat?

Do you worry your slide deck is boring?

And you’re stumbling over your words?

Good news!

If all that’s wrong with your upcoming pitch to potential investors, there is NO WAY its going to go badly as the meetings this story is about.

We asked a few VCs and entrepreneurs to share some of their more memorable pitching disasters.

We came up with stories about entrepreneurs dressing like avocados, VCs leaving broke CEOs with the check, and people falling asleep in meetings – plus more delightfully awful details.

Of course we’re not just relishing in all this misery; there are very valuable lessons to be learned from these mishaps.

This entrepreneur made his own VP fall asleep

This entrepreneur dressed like an avocado

The story: There probably isn't anything less appetizing to a VC than someone dressing up as green, mushy food. But that didn't stop one lady who showed up at New York VC Steve Brotman's office dressed like an avocado.

'You lost me at hello,' Brotman told her, according to ReadWriteWeb.

The reaction: 'I'm not about to do a deal with a lady dressed like an avocado,' said Brotman.

The lesson: 'Don't let your product influence how you dress,' they write. 'VCs don't enjoy gimmicks.'

This entrepreneur thought he was special and the rules didn't apply

This entrepreneur was told to go back to the bank he quit and ask for his job back

This entrepreneur babbled on about useless details for an hour

This entrepreneur tried to get around an NDA

This entrepreneur showed up late

This entrepreneur insulted the VC

This entrepreneur was left with the bill for a lobster dinner

Keith Cowing, founder of SeemlessReceipts, thought he was going to get advice from a VC's consultant, but got a bill for a massively expensive dinner instead:

The story: When I was first raising money for Seamless Receipts, I talked to a number of venture capital firms and early-stage investors. At the end of one pitch, a VC introduced me to an 'independent consultant' who could provide expert advice, put us in touch with early customers, and perform some of the VC's diligence. The consultant had been a partner at a big firm, had served on the boards of several successful companies, and looked great on paper.

I emailed the consultant to setup the meeting, including myself and my business partner. He responded by forwarding me a dinner reservation at an expensive restaurant in New York the following night. This was rather unusual. We hadn't even setup a day and time for the meeting and here was a PDF copy of a restaurant reservation. As a scrappy entrepreneur, I tend to eat at restaurants that have dollar menus. But I figured he would pay if he made the reservation. Worst case I'd pay my share and it was a worthwhile expense for his time, which was clearly valuable.

We met for dinner the next day (his schedule seemed awfully flexible). He happily ate his food, but was more interested in the New York party scene than our business. We couldn't get him to muster up any logical feedback or provide any value during the discussion. Then there was the finale, he left us with the bill for his lobster dinner. I was aghast! This was worse than a pay-to-pitch scheme. We paid for the expensive dinner that this guy set up, he wasn't even a potential investor, and he had no expertise that I could discern. What kind of 'successful' business person makes a young, budget-conscious entrepreneur buy him lobster dinner?

The reaction: Cowing writes: 'I have a lot of respect for most VC's and consultants I've met. But this was ridiculous. I wanted to launch a nasty email to the consultant and the venture partner who made the introduction, but I decided to cool off and simply move on to my next slew of meetings. I won't be meeting with him again, and I will give an honest assessment of his character when asked. But it's a small world and your reputation is more important than anything, so I'm careful with my reactions.'

The lesson: After getting burned, here is Cowing's advice to avoid his same fate:

You should approach the fund raising process with the same discipline, focus, and rigour you use to build a product. This means constantly prioritizing your time. There are tons of investors, 'experts', and entrepreneurs you can talk to. There are plenty of people masquerading as each as well.

So make a giant list of people and firms, track it, trim it down to those who can be great partners, and spend your time accordingly. Identify the bad apples as fast as possible, toss them aside, and don't look back. The sooner you develop meaningful relationships with people in the venture community, the more you can triage your schedule (and cut out people who will waste your time), I might have gotten stuck with a useless meeting and a bill for a lobster dinner, but I won't get stuck twice.

This entrepreneur was cheesy and painful

This entrepreneur had too many features

The story: Jared O'Tool, co-founder of, overwhelmed VCs with his pitch and received a room full of blank stares.

He explains:

About 2 years ago I was pitching VCs on a business plan we had made before Under30CEO was around. We thought it was the next big thing and spent hours creating the idea and how the service would work online. Then we went to the VCs.

Problem: To many features. We thought it was great that we had incorporated all these fun features to the service all these ways people could share, react and get involved. What we failed to do was talk about and make the actual service and the target market clear at all.

The reaction: 'The VCs were generally confused on the whole project because we spent more time trying to explain features than explaining the core offering and why people were going to use it,' O'Tool recalls.

The lesson: O'Tool advises: 'Focus on the core and the market. Tell VCs what your doing and why people need it. An investor does not want a project that needs a revolutionary feature or promotional tactic to work. They want a project that fills a need in the marketplace, simple as that. How it will be delivered, promoted and the fun features are all secondary and cloud the actual core business.'

This entrepreneur thought he could change the world

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