Packy McCormick’s Not Boring parlay: Angel S6 E3 + Producer Rachel visits Miami Hack Week | E1372

Episode Summary

Executive Summary: Packy McCormick discusses building Not Boring as a media-first venture platform, raising Fund Two with a parallel structure for accredited and qualified investors, using syndicates/SPVs to increase access and follow-on flexibility, and navigating valuation swings transparently. The episode also highlights Rachel’s on-the-ground Miami Hack Week interview with TAP co-founder Eric Button about hiring, community, and the role of in-person tech events.

Main Topics: Packy McCormick’s media-first venture strategy (Priority: 5/5): Packy explains that his newsletter and public writing are central to his investing edge, not just marketing. He emphasizes humility, learning in public, and using writing to explore industries rather than pretending to be an expert. Fund One performance and Fund Two structure (Priority: 5/5): The discussion covers Fund One’s early portfolio results, Fund Two’s fundraising status, and the use of a parallel fund structure to accommodate both accredited investors and qualified purchasers while maximizing participation from readers. Regulatory constraints and capital formation access (Priority: 5/5): Jason and Packy debate SEC accreditation rules, investor caps, and how current regulations limit broader participation in private markets. They argue for more inclusive and educational pathways into venture investing. Syndicates, SPVs, and investor allocation management (Priority: 4/5): Packy details how he uses syndicates and SPVs to extend access to deals beyond the fund and to manage tension between LPs and public readers by offering priority to fund LPs first. Investing through volatility and communicating with LPs (Priority: 4/5): The conversation addresses how to report performance honestly through market corrections, the importance of long time horizons, and why IRR can be misleading in early-stage or token-driven investing. Miami Hack Week and the future of in-person tech community (Priority: 3/5): Rachel’s interview with TAP co-founder Eric Button shows how hack weeks create recruiting, networking, and community-building value, especially among Gen Z tech Twitter participants who benefit from real-world interaction.

Key Arguments: Packy argues that writing as a VC should be exploratory and humble, because he is learning alongside readers and often investing in industries he is still studying. He says his failures and outsider perspective make it inappropriate to act like a guru; transparency is part of his credibility. He contends that public fundraising via a media brand is new and needs guardrails, but current SEC limits are overly restrictive and arbitrary. He believes private-market access should be broadened through higher investor caps and better financial-literacy tests, rather than excluding most people. He says syndicates and SPVs help maximize access and allow readers to participate alongside the fund when the fund cannot take all of a deal. He frames Fund Two as a more concentrated, larger-bet strategy with a bigger Web3 allocation and a goal of being more helpful to portfolio companies. He emphasizes that LP communication should be honest about market volatility, because long-term outcomes matter more than short-term paper marks. Rachel and Eric argue that in-person events like Miami Hack Week create stronger relationships, better hiring, and real opportunities that online networking cannot fully replace.

Data Points: Fund One size: $9.9 million - Packy’s first Not Boring fund was raised publicly and is the basis for the current platform. Fund One portfolio count: 79 companies - Packy described Fund One as a broad, early-stage portfolio. Fund One SPVs before the fund: About 25 SPVs - Packy built investing momentum through syndicates/SPVs before launching the fund. Fund Two target size: $25 million to $30 million - Packy initially aimed to raise this amount for Fund Two. Fund Two demand: $130 million expressed interest from about 1,470 people - Public opening of Fund Two drew far more demand than available capacity. Accredited investor cap: Up to $10 million and 249 people - Packy and Jason discuss the SEC limit for accredited-only fundraises. Qualified purchaser structure: Up to 2,000 people with no practical cap - Used as the larger-check side of the parallel fund structure. Fund One investment cadence: About 100 investments - Packy says Fund One was roughly 100 positions, mostly small checks. Web3 allocation in Fund One: About 15% - Packy says his first fund had limited Web3 exposure compared with Fund Two. Web3 allocation in Fund Two: About one-third - Packy plans to increase Web3 exposure meaningfully in the second fund. Average age of Fund One companies: 5.5 months - Packy notes how early the portfolio still is, making performance hard to judge. Syndicate size: About 1,500 people - Packy says the syndicate is largely made up of Not Boring readers. Syndicate volume: About $4 million invested - Reported amount deployed through the Not Boring syndicate. Typical syndicate check size: $100,000 to $200,000 - Earlier syndicate allocations were in this range before larger fund checks increased. Typical Fund Two average check: Approaching $250,000 - Packy says his average check size is rising as the fund becomes more mature. Major check size: $500,000 to $1 million - Packy has already begun making much larger lead-like investments. Annualized return example: 15 billion percent IRR - Packy jokingly cites an extreme early token investment result to explain IRR sensitivity. Hack Week recorder cost: About $500 - Rachel’s first in-person reporting setup required a Zoom recorder purchase.

Pivotal Quotes: "If I'm going to be writing about a bunch of industries where people who are reading the newsletter spend their whole entire lives working in that industry, and then I come in from the outside after having read a few things in a week and say, This is how you should be doing it... of course, I'm going to get something wrong." — Packy McCormick: Packy explains why he avoids pretending to be an expert and instead learns in public. "I think the mandate should not be to protect people from losing money, it should be to educate people on to be more financially literate and to make money." — Packy McCormick: Packy argues for a more participation-friendly SEC and broader investor access. "I'm learning in public too... it is not rocket science to do this." — Packy McCormick: He describes his approach to demystifying venture capital for readers and LPs.

Implications: The episode argues that media-led venture funds can work if they stay transparent, disciplined, and helpful. It also suggests private-market access will remain a major policy and product opportunity, while in-person communities like hack weeks are regaining strategic importance.