Jun 8, 2015 · 27m · 20vc
20 VC 043: How To Be A VC Analyst and Lessons From Union Square and First Round with Charlie O'Donnell, Founder @ Brooklyn Bridge Venture
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Twenty Minute VC, host Harry Stebbings interviews Charlie O'Donnell, founder of Brooklyn Bridge Ventures, to explore breaking into venture capital, managing micro VC funds, and effective deal sourcing strategies.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 19.2% of the talking time here. How this is scored →
Harry as informed peer 1.5 Guest teaching 4.0 Guest disagreement 2.3 Harry pushing back 0.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:55 Blunt rejection of Kickstarter pre-VC framing
Charlie directly shuts down Harry's query asking if Kickstarter is a pre-VC stage with a flat 'Well, they're not making investments, so no, I wouldn't say that.'
Hardest push from Harry ▶ 20:00 Harry pivots to clarify general financing contextAfter Charlie flatly denies that Kickstarter is pre-VC, Harry immediately pushes back to rescue his point by clarifying 'But just of financing in general.'
Biggest teaching moment ▶ 11:30 Explaining institutional LP ticket size constraints for small fundsCharlie breaks down the mathematical impossibility of sub-$40M funds taking institutional money because institutional LPs require minimum check sizes of $10M.
Harry holds his own ▶ 20:05 Restating the premise around crowdfunding as general financingHarry re-asserts his core point after Charlie's quick rejection, steering the conversation back to crowdfunding as a functional layer of startup financing.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Charlie O'Donnell's Journey into Venture Capital | 1 | 4 | 2 | 0 | Harry asks broad questions about breaking into VC and internships. Charlie reframes the premise of how students break into VC, explaining that traditional deal-vetting isn't what junior analysts actually offer compared to community building and operational skills. | |
| Brooklyn Bridge Ventures and Deal Sourcing Strategy | 1 | 2 | 1 | 0 | Harry asks straightforward questions about sourcing and value add. Charlie uses self-deprecating humor about having no real skills before walking through his newsletter and blogging strategy. | |
| Micro VC Fund Strategy and Fundraising Realities | 2 | 5 | 2 | 1 | Charlie educates Harry on micro-VC economics, explaining why funds under $40M cannot raise from institutional LPs who require $10M check minimums. He also mocks the ignorance of family offices who ask basic questions before revealing they don't invest in VC. | |
| Key Takeaways from Union Square Ventures and First Round | 1 | 3 | 1 | 0 | Harry asks for takeaways from Union Square Ventures and First Round. Charlie contrasts his role as a young analyst at early USV with leading deals at First Round, explaining structural differences in partner deal volume. | |
| Personal Branding and Hardware Startup Investment | 2 | 6 | 5 | 2 | When Harry asks if Kickstarter has become a pre-VC stage, Charlie bluntly rejects the premise by noting Kickstarter doesn't make investments. Harry pushes back slightly to reframe it as general financing, but Charlie points out most strong hardware teams raise VC prior to pre-sale campaigns. | |
| Quick Fire Round and Recent Investments | 2 | 4 | 3 | 1 | In the quickfire round, Charlie gently dismantles two of Harry's suggestively framed questions: pivoting Harry's hardware marketing idea to CPG food startup Hungry Root, and explaining why Tinker Garden's curriculum model wouldn't apply to park yoga. |
Statements from this episode (14)
Charlie O'Donnell sourced First Round's early investments in GroupMe and SinglePlatform
“Prior to founding Brooklyn Bridge Ventures, Charlie was at First Round Capital, where he sourced the firm's first investments in single-platform Sold to Constant Contact, and GroupMe, sold to Skype.”
GM Pension Fund has invested in every Accel fund since Accel I
“GM had been an investor in venture funds since the late seventies. They're invested in Excel, for example, all the way on from Excel number one all the way on through.”
Short VC internships fail because deal vetting requires thousands of hours
“Being able to vet deals, I think, requires some amount of experience and just, you know, getting your 10,000 hours in looking at looking at startups. So I think it's really hard to just pop in somewhere for a couple of months and expect to be productive.”
Aspiring VCs should master recruiting, PR, or customer acquisition
“Anybody who mastered the skill of either recruiting or PR or customer acquisition for startups can leverage that skill at a firm, especially as more and more firms are looking to build platforms that add value.”
Brooklyn Bridge Ventures funds pre-seed founders at the PowerPoint stage
“I'm very early, so I'm often the first money in. I've funded Founders with ideas. I've funded PowerPoints. I've funded things coming out of hackathons things before their Indiegogo pre-sale takes off, so.”
Brooklyn Bridge Ventures is currently investing out of an $8M fund
“The fund that I'm investing in now is a little over eight million dollars.”
Raising a venture fund under $40M is difficult due to LP constraints
“Most of the people who are sophisticated enough to invest in venture at any kind of scale are writing checks of ten million dollars. They're not investing in eight or 15 or twenty million dollar funds, and so it's really hard to raise a fund that is less than,…”
Charlie O'Donnell was present for USV's Indeed investment and first Etsy meeting
“Although I was there when we invested in indeed and there for the first meeting when we met Rob Kalin and at Etsy.”
USV partners do 1-2 deals yearly versus First Round's 4-5
“And then also they're two different types of firms, too, so the likelihood that you'd get a deal done at USV when each partner's doing one or two deals a year was, Very different than first round when they're doing four or five because they're seed deals.”
Crowdfunding pre-sales make early-stage hardware VC investments economically viable
“All these various pre-sale platforms are really making it economically viable for VCs to make early stage investments, because you're not funding the manufacturing, the customers are funding the manufacturing, and so, you know, you, it's a lot easier to swallo…”
No hardware startup on crowdfunding platforms has ever delivered on time
“Well, no one's delivered on time yet in the hardware space, as far as I know”
Most of O'Donnell's hardware portfolio raised VC before launching pre-sales
“Three of the four hardware related companies I did raised VC before they went to pre-sale.”
Charlie O'Donnell convinced Tinker Garden founders to go full-time before investing
“I'll tell you the one I most recently announced is a company called Tinker Garden, and Tinker Garden was a company that I not only, I can't say I said yes, because the entrepreneur didn't really pitch to me. I sort of convinced themselves, I convinced the entr…”