Jason Chapman brings a distinctly technical lens to early-stage investing. Before launching Convoy in 2018, he was an engineer at IBM's artificial intelligence division, writing code 12 to 18 hours a day. That background shapes how he evaluates deals: he wants to be the most knowledgeable investor on a founder's cap table, going deeper than the typical mile-wide-inch-deep approach. Convoy writes concentrated $3-5M checks, doing only six to eight investments per year, and Jason has led follow-on rounds up to five times into the same company. His pitch to founders is straightforward: his personal net worth is tied up in the fund, so every check carries real weight and aligned incentives.
The tactical fundraising advice throughout the episode is where founders will get the most value. Jason lays out a specific cold outreach formula: find 50+ funds by looking at who backed tangential, non-competitive companies, then craft a two-to-three sentence email with a provocative opening line. His hot take is that LinkedIn actually outperforms email because most investors have heavy spam filters that catch attachments and unknown senders. He also recommends linking to a DocSend deck rather than attaching a PDF, and shares a pre-call tactic a founder used on him that he loved: sending a prep email two days before with five key takeaways and the top two reasons other investors were passing. That kind of transparency, front-running the bad news, softened the blow and built trust immediately.
Jason is also candid about the red flags that kill deals fast. Co-founder tension on a call is an instant pass, fabricating term sheets or timelines will get exposed because VCs talk to each other, and having all four co-founders on an intro call reads as a yellow flag rather than a show of strength. On the post-raise side, he warns against overhiring in engineering before revenue catches up, and encourages founders to think seriously about whether they even need more than one or two equity rounds. His closing advice gets personal: make sure your spouse is fully aligned before you start, and build a support system because building a company is incredibly lonely.
