Shoot Your Shot : The Anatomy of a Cold Email

Successful cold outreach starts with two mindsets: ditching the imposter syndrome, and showing up as a bold version of yourself. Taking the shot now means no “what if” feelings later, and the potential of unlocking opportunities you didn’t think were on the table. 


Just ask Sam Wicox, a Stanford MBA student who landed an internship at Permanent Equity with a single well-crafted cold email. Sam’s success story is a prime example of how a properly executed reach out can unlock unexpected opportunities.

The Delicate Balance

Like most things, cold outreach is a tactical mix between showing genuine interest and respecting boundaries. You want to stand out without coming on too strong. Approach each outreach with confidence while understanding that timing plays a crucial role in the outcome.

Personalization is a Power Move

Communication should never feel templated or mass-produced, regardless of the format. Each message should be crafted specifically for the recipient by incorporating: 

  • References to their specific work, content, or achievements

  • Thoughtful observations that demonstrate you've engaged with their material

  • A thread between their work and your background

Personalization proves you’re worth a reply. 

Crafting an Impactful Subject Line

Your subject line determines whether your carefully crafted message ever sees the light of day. Consider Sam’s subject line: 

Yes, it’s simple, but there are key elements to this subject that make it effective:

  • Highlights relevant credentials concisely

  • Clearly states the purpose of the email

  • Is direct and easy to understand at a glance

The Message

Hi Brent, 

I’m a few weeks into my first year at the GSB and starting to think about internships for next summer. I was wondering if Permanent Equity ever brings on MBA interns in Columbia? I've been following Permanent Equity over the last few years through your (semi-ish) annual letters, and really admire how you've built out the fund. 

I have a bit of a nontraditional background, but I think it might fit with Permanent Equity’s "weird" structure. I started at Oak Street Health right after their Series B, then cold-emailed my way into an investment banking analyst role and worked my way up to VP in just three years. After that, I served as Deputy Mayor of Nashville, managing policy, communications, and strategy teams, and led negotiations on behalf of the city for a new stadium with the Tennessee Titans. Most recently before starting school, I co-founded Vamos Health—a direct primary care startup focused on serving Spanish-speaking communities.

It’s been an unconventional path, but it has given me a lot of perspective on the type of work I want to do (collaborative, interesting, and hard) and what kinds of people I want to work with (not assholes). If there’s a chance to chat or explore internship possibilities, I'd be thrilled to connect.

Best,

Sam Wilcox

FWIW, my wife's family is from St. Louis and we are looking to move back closer to family after school. 

Sam opened by referencing something specific about Permanent Equity. It showed he wasn't just reaching out to anyone. The body of his outreach validated his familiarity with Brent’s's work. Referencing the "semi-ish annual letters" showed Sam had been following Permanent Equity’s communications patterns closely.

He presented his background as a narrative rather than a resume. People don't connect with titles; they connect with stories. This approach helped Brent understand not just what Sam had done but why his experience made him relevant to what PE might need.

Sam's strategic callouts to unique aspects of the organization demonstrated genuine research and interest. Mentioning the company's "weird" structure (which PE proudly embraces) showed he understood their organizational values.

Clear Intentions and Alignment

Sam was specific about what he was looking for and why. He named the type of work he wanted to do and the kind of environment he thrived in, clearly articulating he was looking for work that is collaborative, interesting, and hard.

Clarity = confidence.

It helped Brent know exactly how to help (or who to forward him on to in the event the Brent wasn’t the best contact).

The Closing: Adding Final Value

Sam ended with a professional sign-off that included an additional benefit and clear connection opportunity. Mentioning relevant circumstances like "moving closer to St. Louis after graduation" provided practical context for why this connection made sense.

The Result

Sam's carefully crafted email did exactly what he hoped—it started a conversation that led to his internship at Permanent Equity. The difference between a deleted email and one that opens doors comes down to these key principles:

  1. Research thoroughly before reaching out

  2. Show you’ve done your homework with real references.

  3. Be concise but comprehensive in your communication

  4. Demonstrate value alignment with the organization

  5. Respect their time with focused, relevant information

  6. Follow up thoughtfully if you don't receive a response

Don't wait for the "perfect moment" to send your thoughtful outreach. Companies' priorities shift, hiring needs evolve, and decision-makers move roles. Your well-crafted message today could align with an opportunity that won't exist tomorrow. A thoughtful cold email is simply an opportunity to make a connection that wouldn't otherwise exist. The rest is up to you.