Not Boring Capital's Upside-Focused Investing Approach
A high-volume, minimal-diligence venture strategy built on trusting co-investors and chasing upside
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 6
- Confidence
- 65%
Packy McCormick describes a distinct venture investing approach built around his newsletter's audience and time constraints: rather than leading rounds, negotiating terms, writing exhaustive memos for every deal, or sitting on boards, he makes many small, non-controlling investments (91 in Fund I), trusting that a lead investor or another trusted co-investor has already done the downside diligence. His own role is to focus purely on identifying what could go spectacularly right about a company, publish his reasoning transparently (often the same memo goes to LPs and readers), and stay equally available to portfolio founders whether the company is thriving or struggling. This trades some downside protection for speed, deal flow, and reach — a trade Packy is explicit and transparent about with his LPs.
Origin
Emerged from writing a memo to help a friend explain his company, which turned into a syndicate deal, then a full fund because writing a new memo for every deal became too slow.
Core principles
- 01In venture, only the big wins matter — the strategy should optimize for upside, not for avoiding every loss.
- 02Delegate downside diligence to trusted co-investors rather than duplicating everyone's work.
- 03Write shorter, faster investment memos to keep pace with high deal volume.
- 04Stay equally responsive to underperforming and outperforming portfolio companies.
- 05Publish reasoning transparently so external observers can hold you accountable.
How to run it
- 1
Build Inbound Deal Flow Through Content
Use your public writing and audience credibility to have founders come to you, rather than sourcing cold.
- 2
Avoid Leading Rounds or Negotiating Terms
Let other investors do the heavy structuring work (term sheets, valuation negotiation) so you can move fast on many deals.
- 3
Trust a Credible Co-Investor's Diligence
When a reputable fund or investor is leading the round, rely on their downside diligence instead of duplicating it yourself.
- 4
Focus Your Own Analysis on Upside Potential
Spend your limited time asking 'what could go really right here?' rather than hunting for every possible flaw.
- 5
Write Fast, Not Exhaustive, Memos
Keep investment memos short enough to not slow down your ability to say yes quickly to founders.
Watch out This means you will sometimes be wrong or miss red flags other diligence-heavy investors would catch.
- 6
Stay Equally Available to All Portfolio Founders
Answer calls from struggling companies as quickly as from the obvious winners, since you know what it's like to be on the other side of that.
In the wild
Packy deployed a $9.99 million Fund I into 91 different startups, without writing a full investment memo for each one, relying on trust in the ecosystem and other lead investors' diligence.
→ The volume-based, upside-focused approach let him build a broad portfolio quickly despite operating alone with no analyst support.
Common mistakes
Confusing this approach with due-diligence-free investing
Packy is careful to note he's not ignoring fraud risk entirely — he's trusting an ecosystem of co-investors, which could still fail if that trust is misplaced.
Treating founder relationships transactionally
Packy explicitly avoids becoming an investor who only pays attention to companies that are 'winning,' since that abandons founders when they need support most.
Is it for you?
Best for
Solo GPs or creator-investors with strong inbound deal flow but limited time/staff for traditional diligence
Not ideal for
Investors managing very large funds who need to lead rounds and take board seats, or those without a trusted network of co-investors
From the transcript
“i trust that if a good fund is leading the round or somebody that i trust is is leading the round that they've done that…”
“venture capital's never about the mistakes the only thing that matters in venture capital are the ones you get right and that's kind of the…”
From the episode
Not Boring (with Packy McCormick)