10 clips
BBuilding Great Tech
Daniel Cheaib shares the darkest moment of his startup journey when the team ran out of cash, stopped working on the product, and he had to take a second job while facing his fear of failure. Just when everything seemed lost, an investor reached out and changed their trajectory in three weeks.
VVillage Global Podcast
Henry Shi reflects on his transformation from founder to VC, sharing how getting rejected 144 times while fundraising gave him unique perspective when he moved to the other side of the table as a venture partner. He discusses how pitching investors is one of the least enjoyable parts of starting a company and what he learned about the investor mindset.
TThe Pitch
A founder successfully secures investment from VCs during their pitch, raising $700K of their target $1M round. The VCs express interest in participating and the founder confirms they're planning to close the round with a term sheet the following day.
TThe PMF Show
Chaz Englander explains his direct approach to fundraising outreach, emphasizing the importance of establishing credibility in the first few words of any cold message. He discusses how networking compounds through introductions and shares his strategy for crafting opening messages that get responses from investors.
TThe Full Ratchet
This special segment explores the most insightful questions that allocators (LPs) have posed to venture capitalists during fundraising or evaluation processes. Three VCs share standout questions that challenged their thinking and approach to investing.
RRiding Unicorns
Manny Medina warns founders against scaling too early with investor money, emphasizing the need to understand customer problems and establish genuine market advantage before pressing the gas. He uses the humorous example of wasting funds on Times Square advertising to illustrate how quickly misallocated capital can lead to investor frustration.
LiveKit's co-founder Russ d'Sa reveals how he and his cofounder strategically used a 'good cop, bad cop' approach during investor negotiations. One founder would negotiate while positioning the other as unwilling to accept certain terms, creating leverage in fundraising discussions.
A founder discusses the necessity of SOC 2 compliance for enterprise customers and outlines their fundraising strategy. They're raising $1M pre-seed to hire ML and full-stack engineers, having already secured $165K, and emphasize ending free proof-of-concept work.
Equity · Build Mode
VC Yuri Sagalov explains why founder dilution above 25% becomes a major red flag for investors and why it's extremely difficult to fix once it happens. He discusses how some investors will pass entirely on over-diluted companies because unwinding bad cap table structures requires uncomfortable conversations about people owning less equity.
Gauthier Van Malderen explains how he and his co-founder Matt leverage complementary skills at Perlego, with Gauthier handling sales, fundraising, and vision while Matt focuses on technical execution. He describes how this division of labor helped them successfully pitch AI solutions to investors, with Matt building the technology and Gauthier packaging it into a compelling investment narrative.
