Brooklyn Bridge Venture’s Charlie O Donnell painstakingly explains his thought process

But some people don’t always get it. Like at this not-a-pitch event last week, one guy stumbles through pitching a social sharing mechanism, using a Chrome extension.

“But what’s wrong with sharing through Facebook and Twitter?”, poked Charlie.

“I’m trying to get to that.. users will have lists that they could share to — “, guy-with-meh-idea restated.

“Why would I download your Chrome extension and create these lists — “, Charlie interrupted.

“You’re not letting me finish. I’m trying to explain — “

Tension shot through the room. Both Charlie and the hopeful pitcher were not hearing each other. The audience is scattered across five rows of wooden seats, perfectly aligned towards Charlie,casually leaning against the table, who elaborates—

“You have to help me get through this hump, as stupid as it might be. When you’re pitching to an investor, you need to help him over these hurdles before moving on.”

And with that said, it was time to move on to the next pitch. His time was up, and he had failed to complete his pitch. This led to two insights:

  1. Take the time to fully understand what the investor is asking when pitching, don’t make any assumptions on his knowledge, and answer it with details. Whether or not he may have already known the answer, at the very least you prove yourself capable of honing in on the exact question in the investor’s mind, synthesizing it, and clearly communicating it. This is valuable on its own.
  2. Having a model of the user is of utmost importance. This involves some insight on the psyche of users, their tendencies, their problems, etc. Additionally, if these insights are backed by surveys or actual user behaviors, with a prototype, that’s a huge bonus.

The evening was littered with gems like these. Charlie’s feedback not only cut into what every VC is looking for from potential investments, but offered a framework of analysis for what every entrepreneur should use for his or her own venture. I’ll go through several of these in this format: 1) the pitch, 2) Charlie’s precise feedback. I think this layout of entrepreneurs pitching their ideas from a diverse distribution of industries and business models and having a VC candidly provide feedback is really useful, and it’s worth sharing a recap to those who couldn’t attend.

Here are a few snippets of the night

Pitch: A lawyer who worked w/ two large firms over a period of 15 years pitched an idea of building a document-storage system geared towards enterprise deals. Gathering documents in preparation for fund-raising is an ordeal that can take months. It’s a bottleneck for most companies and ripe for making efficient.


  • At what size of company does document management become a pain point? 50, 100?
  • Is the space large enough between the kludge of all these big players? Dropbox, Google, Microsoft, Email, etc.
  • Showing me a landscape of the competition and where you fit in and how you differentiate yourselves would be really useful.

Pitch: An investment platform in between Betterment and Robinhood. Trades are free, users are given some hints or insights on their next move.


  • Who’re the people willing to spend the time here? Is this population growing or shrinking?
  • Can a big player like Charles Schwab do this and push you out?
  • You’re going to need a strong customer acquisition person on your team.

Pitch: The world’s next CIO’s need mentors. Post detailed mentorship content (interviews and such) from today’s up-and-coming CIOs on a site. Use either a subscription based model or a coursera model where you get a certificate at the end.


  • Why would up-and-coming CIO’s charge for their content?
  • Why not put it for free on Medium or their own personal site?
  • Maybe you can keep running these conferences for CIOs to speak at, and scale to different cities
  • You can still run a very successful company without scaling to $500 million in market value. I may not invest in you, but you can still make a lot of money.

Pitch: Group search on rental property. For instance, two people might be independently looking for a two bedroom in Bed Stuy at a certain price point. Connecting these people can solve their problem.


  • Is it Tinder for roommates?
  • Is the number of people experiencing the problem growing? Don’t most people just figure it out, using mutual friends or Craigslist?
  • Can you license out this group search to rental listing sites? Don’t create yet another rental listing site. I’m not interested in that.
  • I can introduce you to the Streeteasy guys.
  • Even Streeteasy only sold for $65 million. There’s not too much growth/money in this model.

Pitch: Hands free vaping. The vaporizer is a bracelet around your wrist, that you can smoke directly from.


  • Do you want to build a product or a company? You can still make a lot of money from selling a product
  • I can introduce you to a product/marketing guy. This guy’s a wizard.

Other bits of gold from Charlie from other pitches

If other people have tried it and failed in the past, you need to know exactly why they failed and how you’re different.

In a competitive space, provide a visual layout of the landscape and how you differentiate

If an enterprise signs up for your services and it doesn’t work out as expected, what’s the downside for them?

You’re asking a lot from the user to [install this extension|video-chat a stranger|download another app]

Key insights

  • Rapid growth potential is a prerequisite for VC funding. Simply adding another store or getting a product in the hands of users is not enough. Having a plan to scale is something that Charlie looks for, as well as most VCs. If you can show rapid growth and cash flows, investors will come.
  • In a competitive space, it’s important to be able to succinctly describe the landscape and how you differentiate from it. This includes past failures.
  • Make as few assumptions as possible. For instance, you might understand consumers of product or content, while making assumptions about the producers of such content. Or for instance, some idea might not be immediately clear to users, so have a way to step the user through any complex process (or simplify the process)
  • Showing up and putting your idea in front of Charlie can definitely change your business. Charlie offered to make a few introductions to key people he knows. It’s clear that he wants to be helpful, and had shown some clear examples of it during the event. If you can get face time with a VC in a casual setting, do it!

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