Hi.
I’m Charlie O’Donnell and I was a venture capital investor for over 20 years—investing in over 100 startups and putting tens of millions of dollars to work. I worked at Union Square Ventures, First Round Capital, and my own firm, Brooklyn Bridge Ventures.
I advise companies on their fundraising on a very limited basis.
I’m not here to sell startup support or give you a pat on the back for deciding to launch something. I’m here to tell you hard truths about whether a VC is likely to get behind this and whether something can be done to improve your chances.
If you have a real shot at a raise, you’ll have a better deck at the end of our meeting, but I might also walk you through my opinion of why you’re not going to be able to raise venture or how your startup needs more work.
No amount of fixing the deck is going to solve the problem of a broken business model or a startup idea that is far from the most promising opportunity for a VC to make money.
This isn’t a branding, wordsmithing, or graphic design exercise. You’re about to quit your full-time job or ask your closest connections to invest in your business—or you’ve already done that.
What you’re buying is my experience.
I’ve been in hundreds of partner meetings. I’ve invested in over 100 companies, syndicating these deals to thousands of potential co-investors.
I can tell you how VCs think about opportunities based on firsthand knowledge, not from podcasts or Medium posts.
I don't treat every opportunity as a rewrite away from a successful raise. That's patronizing—and disrespectful of a founder's time and resources.
I treat each company as one of 2000 opportunities a VC could see in a year to help explain the gap, based on firsthand experience, between where you are and where the 5 or 10 deals are that get across the line to an investment.
Testimonial:
“I engaged Charlie after spending 6 months fundraising for my business. During my time fundraising I struggled with finding the right message and positioning for my startup. I pitched and met 100’s of investors but had limited success in closing them, and they never gave any feedback or detailed information about why they weren’t investing.
I felt like I was pitching in the dark and I felt I didn’t truly understand my customer (i.e. VCs) enough to get my pitch right.
Charlie’s advice and guidance was immensely valuable. He helped me see fundraising from the other side of the table and understand what VCs are looking for and how to tailor my pitch to that.
He understood my business very quickly, he was able to tie it back to real world examples of similar situations he’d been in as an investor and that really helped frame my thinking.
Charlie left me with clear actionable insights for improving my pitch and my pitch deck so I would be more attractive to VCs. I came away from our workshop having learnt more in my time with Charlie about VCs and fundraising than I had in 6 months of consuming every online resource I could find, and pitching to 100’s of investors. - Ben Tilley - Founder, Pencil