#10xThinking: How to Train Your Investor Brain

Issue #25

Venture capital (VC) investing is one of those roles you usually have to prove that you can do before ever landing the role. Hiring managers will want to know if you understand the landscape, whether you can work with founders, if you can run diligence, defend conviction, and present a deal credibly to an investment committee. That is the whole point of the intense, multi-stage hiring process.

Founders should care about this too. Improving your investor lens helps you sharpen your pitch, anticipate the hard questions, and present metrics that actually map to what investors look for. It will make fundraising faster and give you clearer signals about what to build.

If you want to move from admiring startups to sizing up winners, you need new habits. This issue walks through practical, low-friction steps to start thinking like an investor and build the instinct founders and aspiring VCs need.

Learn by doing, read the firm playbooks, listen to investor conversations, watch pitches, and refer to our #10xOpportunity series.

If you want to know how investors think, you should spend time where the work happens. Apprenticeships, fellowships and other cohort-based programs give you the rhythms of the job: sourcing, the way investment memos and diligence notes are written, and how investors build conviction for a deal. For a founder, this could be accelerator or other founder / startup programs that can help you sharpen your pitch.

If you missed it in our weekly roundups, check out Venture Cooperative. It is a hands-on apprenticeship built to give aspiring VCs real-time exposure to the day-to-day of venture capital. The application window closes tomorrow, September 21, 2025 at 11:59 p.m. Eastern. 

Actionable moves:

A quick note: Applying for these programs itself can be useful training. Read about my experience flagging Moove as a "soonicorn" during an application exercise last year here. Or see how Conor Brennan-Burke, founder of Hyperspell, treated 6 Y Combinator rejections as a training loop and, on the 7th attempt, finally broke into YC F25.

VC firm websites are not just marketing. They are operating playbooks. Thesis pages tell you what the firm thinks is getting big. Portfolio pages show you what the firm actually bets on, and “why we invested” pieces show which signals convinced them in the moment.

Here are some website pages to interrogate:

For a concrete example of a “why we invested” post and how it reads at the moment of conviction, see this sample by Catalyst Fund. It is a good model of the format and the kinds of signals firms cite when they announce an investment. Also, feel free to check this post for more.

Podcasts let you sit in on investor conversations and founder debriefs without applying for a job. They are free office hours for pattern recognition.

Here are some podcasts I’ve found recently:

How to use episodes: make a playlist, listen to two episodes a week, and for each episode, write down one market signal, one team insight, and one structural or exit-related takeaway.

Your feed is your daily training set. Follow investors and founders who publish thoughtful deal write-ups. Save the “why we invested” posts that make you think differently, and collect term-thread highlights and deal post-mortems to read later.

One newsletter I found recently is Playing Point — Musings of an Emerging Market Investor. Subscribing to one thoughtfully curated newsletter can save you hours of noise filtering each week. 

Another type of post to collect is investor reflection on missed opportunities. Those “anti-portfolio” notes are short lessons in what investors would do differently. They reveal risk frameworks and failure modes that rarely show up in press releases.

A final perk: following the right people uncovers events, panels, and live pitch sessions (more on this next).

Pitch sessions that feature seasoned investors as judges are a condensed masterclass in what founders choose to highlight and what investors look out for / push on. The best lessons are visible in the questions investors ask on stage.

How to get value from pitches:

A small hack is to volunteer at an event. You get backstage access and a lot more time with the investors who judge the pitches.

VCs usually underwrite deals that can return at least ten times the capital invested. Our #10xOpportunity series uses that requirement as a test and a frame for analysis. The series breaks down why a startup could scale to the kind of outcomes that justify a VC check and what aspects of the business model might have driven the VC firm's conviction. 

As an example, see our Cerebrium piece here and if you want a shorter example, this intella write-up is a good micro-case.

Core checklist for 10x thinking:

Practice this once a week by building a one-paragraph path-to-10x for a company and then listing the three things that would most likely stop that outcome. 

Thinking like an investor is about building habits. Over time you will find your questions sharpen and your judgments align with real-world outcomes.