Guyset Toolkit: Friday June 27

Welcome to my first-ever newsletter, Guyset Toolkit!

Welcome to my first-ever newsletter, Guyset Toolkit! Guyset Toolkit is a weekly newsletter that will be delivered to your inbox every Friday. The sections are

1. What To Talk About On A Date

   1. pop culture updates to keep you, up to date)

2. This Week on Guyset Podcast

   1. a recap of this week’s episode, this one was Phoebe Gates!)

3. Worth Your Time

   1. my recommendations and things I’m excited to tell you about that I think are worth your time

What To Talk About On A Date:

• Love Island (it’s going downhill and I’ve stopped watching)

• Vogue editor-in-chief stepped down after 37 years

• Lorde’s new album

• Jeff Bezos and Lauren Sanchez wedding in Venice

• Brad Pitt got robbed (new movie F1, unrelated)

This week on Guyset Podcast:

I had the incredible opportunity to sit down with Phoebe Gates, co-founder of Phia, the shopping app that's changing how we discover and buy clothes. What I loved most about our conversation was Phoebe's brutal honesty about her journey—from those late-night roommate arguments with her co-founder Sophia in their Stanford dorm to building a comprehensive price comparison tool that's genuinely solving problems for shoppers. She doesn't pretend she built this from nothing, but she's also not letting her privilege stop her from creating something truly useful. Her refreshingly authentic response to being called a "nepo baby" is exactly why I wanted to have her on the show.

The insights Phoebe shared about entrepreneurship were game-changing for me personally. Her approach to handling criticism by filtering it based on whether someone is actually her target consumer is brilliant, and I'm definitely stealing her ChatGPT strategy for preparing smart questions before important meetings. But the moment that really stuck with me was when she shared Whitney Wolfe Hurd's "water pitcher" metaphor about energy management—the idea that we wake up each day with limited energy and need to be intentional about whether we're watering real plants or wasting it on plastic ones. It's completely changed how I think about where I spend my mental energy every day. Whether you're building something, figuring out your career, or just trying to navigate your twenties more intentionally, this conversation is packed with practical wisdom you can actually use.

@theguyset#stitch with @Guyset Phoebe Gates on Guyset #alexcooper #callherdaddy #billgates

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What really resonated with me was Phoebe's transparency about the mistakes she made early on—like spending months perfecting a desktop version when their customers were actually shopping on mobile. Her biggest lesson about staying close to consumers and talking to them early could have saved them months of wasted work, and it's advice I think applies to anyone trying to build or create something meaningful. Plus, we dive into how she balances the intensity of startup life with maintaining friendships and taking care of herself, including her Saturday morning phone-free walks that have become non-negotiable. This conversation is a masterclass in authentic leadership and building something real in your twenties.

Worth Your Time:

1. Phoebe Gates gave me some advice on how to dress better and where to shop. Here are the 5 brands she recommended:

phiaco

A post shared by @phiaco

2. I started reading Stephen King’s book “On Writing” and I’m really enjoying it. If you’re interested in writing, creativity, productivity, or anything in between, I’d recommend it to you.

   You can find it here: On Writing by Stephen King

3. My advice on if I was starting a new job today:

   

   @theguysetWhat I would do if I was starting a new job #corporate #newjob #worktips #postgrad

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4. I saw the show John Proctor Is The Villian and have not stopped thinking about it. I’m going to write a separate post on it this week. If you’re in or near NYC, planning a trip sometime this summer, or wanting to see a show, I really think you should try to go. It was laugh-out-loud funny and incredibly important. I know it’s a play but it feels more like a movie. I could have stayed for 2 more hours oustide of the fact that the woman in front of me had the biggest hair possible and got a booster seat. A full adult woman got a booster seat just to block my view, very kind of her. I wish her all the best.

5. I started watching Veep. It is the funniest show I’ve ever seen. I know I exaggerate a lot. I know. I’m working on it. Believe me when I tell you, you will be non-stop laughing out loud. I am loving it and can’t wait to watch more.