Stop Asking for Permission to Do Your Best Work
Real stories of people who skipped the gatekeepers to get what they want out of life
Dear subscribers,
Have you ever caught yourself thinking:
“If only I can get into this [company/role/school], then I can do great work.”
I spent most of my life stuck in this mindset. But I’ve come to realize that you don’t need anyone’s permission to do your best work. So let’s talk about:
Why chasing credentials is ultimately a dead-end
How to land your dream job with no credentials
How to build a business that skips the gatekeepers
How to raise kids to seek the permissionless path
I wrote this with Jeston Lu, a 19-year-old exploring his own path. Give him a follow 🙂
Why chasing credentials is ultimately a dead-end
I’ve spent alot of time chasing credentials:
Degrees from Brown and MIT
Jobs at Meta, Reddit, Amazon, and other leading tech companies
Countless hours spent on getting good grades and prepping for interviews
Don’t get me wrong — fancy credentials can open doors. But chasing them blindly will ultimately lead to an unfulfilling career because:
You stop following your curiosity. I wasted years in consulting because that's what the other "smart" kids wanted in college. I wish I had spent that time chasing my real interests instead.
You don’t build real skills. Getting perfect grades and memorizing PM interview frameworks takes time away from developing real skills like building, selling, and writing.
So, how do you land your dream job and build a business without permission? Let’s cover some tactical tips and real examples next.
How to land your dream job with no credentials
If you don’t have brand name credentials, it’s easy to get your job application filtered out by resume software and recruiters. The solution:
Reach out to the hiring manager directly with undeniable value.
Let me show you three people who did exactly that:
1. How Jay became Head of Growth at 18 years old
Jay Yang is a 19-year-old who worked for two successful founders before college.
He landed his first job by emailing Tyler Denk, founder of the fast-growing newsletter platform Beehiiv. Here’s the exact cold email that he used to land his job. Note how he makes a convincing argument for Tyler to hire him in just three bullets:
Relevant experience: “I’ve grown my brand to 50K followers…”
Trusted referral: “Abhi Shah (previous intern) thinks I’m a perfect fit…”
Genuine interest: “Beehiiv is my top choice…”
For his next move, Jay went even bigger. He made a full deck showing Noah Kagan, CEO of App Sumo how to grow his newsletter:
The result? Noah hired him over candidates with "better" credentials. Now, Jay runs his own $10K+/month business.
2. How Akshar skipped the resume to reach Shopify’s CEO
Shopify is notoriously hard to get into — their hiring rate is as low as 0.3%.
But Akshar, a Waterloo undergrad, found a way to reach Shopify’s CEO directly. He built an app helping students find study spots on campus and shared it on X/Twitter.
His post went viral and got the attention of Tobi (Shopify’s CEO). From Akshar:
Having Tobi meant I could skip the initial screening process and take-home assignment.
I followed up with Akshar over e-mail and confirmed he got the job!
3. Shishir went from idea to YouTube CPO
Shishir Mehrotra is the CEO of Coda and ex-CPO of YouTube (see our interview). But 15 years ago, he used the same strategy to join YouTube’s early product team:
I wrote down some thoughts on making ads skippable and only charging advertisers when viewers watched them. I sent them to Jonathan at Google, and he called back immediately. He said, "We don't have anybody working on this. Why don't you come and do it?"
The truth is that hiring managers and senior leaders rarely have time to “grab coffee” or “have a quick call” with strangers. Instead:
They're always hungry for thoughtful feedback from people who actually use their products.
I've sent detailed product feedback to folks like Notion's CEO and LinkedIn's CPO. They always respond with genuine appreciation. As you can imagine, this is also a great way to build relationships and get job opportunities.
How to build a great business without permission
Naval has a great quote that changed how I think about careers:
"Code and media are permissionless leverage. You can create software and media that works for you while you sleep. An army of robots is freely available…use them.”
AI makes this "army of robots” more accessible than ever. So, instead of seeking permission from admission officers, recruiters, and even hiring managers — why not solve real problems for real customers?
Want some inspiration? Check out my interviews with people who built great businesses in a permissionless way:
How I Built a 7-Figure Business in <1 Year with AI | Ben Tossell
The Least Risky Way to Start Your Business This Weekend | Noah Kagan
How to raise kids to seek the permissionless path
Living in the Bay Area, it seems like:
Every parent is obsessed with getting their kids into Stanford and FAANG companies.
As a result, they pack their kid's schedules full of after-school programs and weekend activities. I want to teach my kids to think independently and pursue their curiosity instead. Here's the advice I’m giving my kids:
Try many activities to find what fires you up.
Follow your curiosity (be your own best teacher)
Build something valuable for real customers
Learn how to deal with failure.
Keep showing up (consistency compounds)
I'll even do their homework if it allows them to explore what matters. 🙂
Stop asking for permission
I share this advice probably once a week with students and folks trying to transition to product management:
So stop asking to have a call, pick someone’s brain, and grab coffee. Stop chasing the same schools and jobs that everyone else is chasing. Stop being proud of “ex-(company)” on your LinkedIn.
Don’t wait for permission to do your best work.
The only people you should seek permission from are real customers who want to pay you to solve their problems. This path isn’t easy, but it’ll make work feel like play and help you build real skills, relationships, and confidence that nobody can take away from you. Let me know in the comments if you have any questions!