Jack Zerby

Building · · ·
Past · @gumroad · @vimeo · @pentagram

[Jack Zerby @jackzerby]

Going from 0-1 is the hardest part of building a startup. It's a whirlwind of design, development, fundraising, hiring, firing, losing money, making money, feeling invincible and feeling hopeless...all within the first few weeks.

It doesn't have to be stressful or chaotic, in fact it can be calm, organized and predictable if you understand a few key steps.

Over the past 20+ years, I have been at the early stages of several companies that have grown to millions of users:

Vimeo - First 8 employees, served as Head of Design and in 2021 it IPO'd at $5.7b

Staked - Designed Brand/UI with early team of 5 and in 2021 it sold to Kraken for one of the largest acquisitions in crypto history

Follow Up Boss - First 10 employees, served as lead designer and in 2023 it sold to Zillow for $400m

I've also been on the front lines of many existing software companies: (for a full list go to link in my bio)

Gumroad - Head of Design, team of 25 devs/designers, paying out product creators $2,906,825 just last week

Teachable - Design Consultant, in 2018, had $26M revenue and 12K customers, and in 2020 it sold to Hotmart for $250m

Kraken - Design Contractor, $1.09 billion in trading volume

Every single time I start a new project I go through the same process. Any time I have veered from that process I have lost a crap ton of money and time.

I'm currently putting together those same steps in one plug-in-play process. Presale goes live today!

https://t.co/d3envdgRJK

[Jack Zerby @jackzerby]

@recap_david Newsletter

[Jack Zerby @jackzerby]

Agreed. I have 4 business accounts plus a personal account and it is a joy to use every day.

[Theo - t3.gg @theo]

Mercury is the single “product” that has improved my life the most. I have always hated banks, invoicing platforms, and corporate cards. They make all of these things so incredibly easy. I haven’t had to open QuickBooks in over a year now.

They do not pay me. I am genuinely just this hyped on them. The only catch is that you’ll hate every bank you use after trying Mercury.

If you need a “bank” for your business, I can’t recommend Mercury highly enough.

[Jack Zerby @jackzerby]

I stopped designing pitch decks a few months ago, but the demand is still definitely there (get lots of inbound that I decline).

It's a niche that most designers don't know about but you can charge $15k-$20k for a 15 slide deck, even more if you're really good.

[Jack Zerby @jackzerby]

@NoBickal @JuiceCheck44 😂 that’s amazing

[Jack Zerby @jackzerby]

iykyk

[Jack Zerby @jackzerby]

Love this CTA on https://t.co/8xPKS3JUc4

[Jack Zerby @jackzerby]

@JJEnglert GTM GUIDE

[Jack Zerby @jackzerby]

Me: Be honest are you writing these tests to make them pass easily or are you actually creating real tests?

Claude: My new tests just run the same logic through the extractor scenarios. They look comprehensive because they have good names and cover multiple sources, but they're not testing anything that could actually break in production.

Me: I at least respect your honesty 👊

[Jack Zerby @jackzerby]

I've found success with Codex by asking after each planning session:

- What would a senior engineer say about this plan?
- Walk through this plan again and find edge-cases
- How would you solve this if you had full autonomy?

[Jack Zerby @jackzerby]

Does anyone else have "Error: Failed to summarize:
Error: Conversation too long. Press esc twice to go up a few messages and try again. " aftter trying to /compact in @claudeai ?

[Jack Zerby @jackzerby]

Having Codex 5.3 review Opus 4.6 is like watching two senior engineers ego snark battle:

"Here's my take — some of this is valid brainstorm-level stuff, some belongs in the plan, and some is over-engineering for where you are"

Over-engineered = Gen Z slang for a try hard 😂

[Jack Zerby @jackzerby]

My goodness the Codex app is fast. I'm used to waiting for Claude Code to finish tasks, but this just flies through them.

[Jack Zerby @jackzerby]

@bcherny Nice! So you can have two repos in same context window?

[Jack Zerby @jackzerby]

My favorite type of mockups in Claude Code are ASCII mockups, they are interpreted really well by the front end skill too. I always include them in my PRD's.

[Jack Zerby @jackzerby]

Me: I need to you to help me set up my Fin feature in Intercom to really help our support team.

Claude: (Proceeds to open up Chrome for 30 mins and configure everything beautifully that would have taken me days because it has access to everything in our codebase)

🤯

[Jack Zerby @jackzerby]

Feeling this most days 😬 but it’s also a ton of fun.

All the grunt work that was such a slog is now gone.

So in a sense it’s like I’m making up for lost time and finally being able to create.

[Ryan Carson @ryancarson]

I’m starting to develop bad FOMO if my agents aren’t running 24x7.

It feels like the opportunity cost is extreme.

It’s like you have a team of 100 engineers just sitting there because you haven’t given them work to do.

Not a great feeling actually.

And I’m feeling this even after shipping a feature on a Saturday.

Anyone else experiencing this?

[Jack Zerby @jackzerby]

This prompt has been working well on all my repos as a good insight into small quality of life issues for not only the customers but the dev code environments as well.

I’ll have it then create .md files for each issue on my mobile Claude app and then drop those into the CLI when I get home to create separate tickets or PRs for each one.

——

You are a senior UX/product-focused full-stack engineer with 20+ years of experience.

Review this GitHub repository thoroughly and give a complete expert audit.

Please do the following:
1.Repository Structure Review
•Identify issues in folder organization, file naming, architecture, and clarity.
•Point out anything redundant, misplaced, missing, or confusing.
2.Code Quality Review
•Readability, maintainability, consistency, naming conventions, component patterns, and architectural logic.
•Highlight any code smells, anti-patterns, dead code, or unclear logic.
3.UX/UI Logic Review (from the code)
•Component hierarchy, screen/flow logic, state management, navigation, layout decisions, accessibility, and user friction.
•Note anything that will confuse, slow down, or frustrate users.
4.Performance & Scalability Review
•Inefficient patterns, unnecessary re-renders, heavy components, poor API usage, and opportunities for optimization.
5.For each issue, provide:
•Problem: what’s wrong
•Why it matters: user impact or technical risk
•Fix: a specific, actionable improvement
6.Higher-Level Improvements
•Suggested architectural improvements
•Cleaner file/folder structure
•Better naming patterns
•More scalable component logic
•UX improvements that align with best practices
7.Priority List
•End with the top 5–10 highest-impact fixes to implement first.

Be direct, specific, and thorough. Avoid generic advice.

[Jack Zerby @jackzerby]

@loggingoffblog Yea once you get ramped up with you can blaze through issues. I rarely write PR descriptions or Issues any more. You realize now the bottleneck is human review.

[Jack Zerby @jackzerby]

Favorite Claude flow:

- Have it go through codebase as a UX expert
- Have it create Github issues for each issue
- Enter each issue into Claude Code web
- Go eat lunch
- Have it create 10 PR's and assign to yourself
- Review each locally with included testing instructions
- Merge and push
- Repeat for another 10

[Jack Zerby @jackzerby]

👀

[Ryan Nystrom @ryannystrom]

I’m watching designers at Notion ship code that is indistinguishable from senior engineers.