Waiting for Permission is a Cop Out

If you want something in life, it is rarely given to you, you have to go out and take it yourself.

When Richard Branson left school at 15 to pursue his entrepreneurial ventures, his headmaster famously predicted he would either end up in prison or become a millionaire. He would go on to start Student Magazine which led to selling records before becoming the legendary record label Virgin Records. The Virgin brand would expand into airlines, telecom, railways, hotels, healthcare and even space travel. His headmaster was wrong on both counts, Branson never spent any time in prison, and he became a billionaire and visionary leader. All because he believed in himself enough to leave the conventional path that everyone else had walked before him.

Many of us grew up in cultures where we always assumed we needed permission before doing anything. We were taught to be respectful to elders and trust their judgment above our own. We rarely had agency, because we allowed our parents to make most of the decisions in our young lives. What instruments we could play, what majors we could study in college, when we could date, among other decisions. We were always afraid of offending someone or doing the wrong thing. This had long-lasting effects on many in our generation of seeking the approval and permission of others before we acted. It made us behave in a way that was timid and more risk-averse.

Don’t do this. Don’t touch that. You can’t say this. You shouldn’t ask that. We were constantly in self-preservation mode programmed to follow the rules, trying to avoid doing the wrong thing. Meanwhile as adults, others around us were bold and commended for their confidence and brash behavior. It was confusing, because it contradicted everything we learned as children. Study the hardest and behave yourself, and you will be rewarded. The real world isn’t a classroom with a teacher who gives you a prize for getting a perfect score. School rewards those who are compliant and perfect. The real world rewards those who are take risks, are independent thinkers and are willing to challenge the status quo. As we’ve seen time and time again, the smartest or hardest working person in the room, is rarely the most successful. Very few, if any, CEOs or leaders in society were the valedictorians of their class. The individuals who are rewarded are the ones who stand out from the crowd, because they don’t ask permission, they just go for what they want. They know that it’s better to beg for forgiveness than ask for permission. They take the initiative and demonstrate that they can make the hard and bold decisions.

For far too long, industries have had gatekeepers who decided who gets to succeed and get the spotlight. Movie studios got to choose what films would get made and seen. Record labels got to pick which artists get albums and airtime. Publishing and media companies decided who could write books and articles. Agencies decided who could become famous. Venture capitalists got to select which founders could raise money to start companies. The list of gatekeepers goes on and on. And the only way you could make it in any of these industries, was to get permission from the gatekeepers to pursue your dream.

Tearing Down the Gates

But things have shifted dramatically. Technology has democratized industries so that the gatekeepers have lost power and influence. The internet and social media has turned gatekeeping on its head. Filmmakers can make films independently or share their work on YouTube. Musicians can record their own music and be discovered on TikTok or Spotify. People can build followings and become famous via Instagram. Authors can self-publish their books or start a Substack. And startups can start a successful company with a lot less capital, using cloud computing and AI.

My friend Henry Shi and I noticed that a large percentage of founders in his Lean AI Startup Leaderboard are Asian American. I have spoken to a number of these founders, and many of them didn’t see the need to raise outside capital. These founders just focused on doing the work and generating revenue. They didn’t want to bother asking for money from venture capital firms when they could make the money themselves and maintain control and ownership. They needed to prove themselves that there was a there there first, instead of raising capital to find out if a there was there. I believe that half of the reason is not wanting to fail and lose someone else’s money, and the other half is that they may not have had the network to raise from investors. Either way, they started their companies without waiting for permission.

People Remember the Winners

I am constantly inspired by people who seemingly come out of nowhere to get to where they are today. Most of them have no business being in the positions they’re in, based on conventional wisdom. But they find a way, because they defy conventions.

Andrew Yeung was a 27-year old product manager at Google who grew up in China. While living in New York City, he started hosting dinners and mixers to the tech community. His events continue to grow in buzz and attendance and he was dubbed the Gatsby of Silicon Alley by Business Insider. When he was granted an O-1 visa, officially designating him an "alien of extraordinary ability" in 2023, he quit his job at Google to turn his events into a business. Fibe generated $1M in its first year, hosting events around the world that have been attended by tens of thousands of executives and founders.

Harry Stebbings was an 18-year old in England who dropped out of college after 21 days. He was a fanboy of investors and started a podcast called ‘The Twenty Minute VC.’ He precociously reached out to venture capital investors to get interviews. He cold emailed Marc Andreessen 53 times before he agreed to be on the podcast. Stebbings has gone on to speak to over 200 venture capitalists with over 100 million downloads of his podcast. As a long-time listener, it was evident that Harry was very sharp and asked insightful questions. He grew a large following of founders who wanted to learn what investors were looking for. Stebbings turned his podcast into 20VC, his own venture capital fund that manages over $600 million in assets.

Michelle Wu was the daughter of Taiwanese immigrants who graduated from Harvard and became a management consultant at Boston Consulting Group. She resigned and moved home to Chicago to care for her mother who was suffering from mental illness and her two younger siblings. Wu started a local tea shop to support her family before moving back to Massachusetts with her mother and siblings to attend Harvard Law School. After graduation she became the first Asian American woman to serve on the Boston City Council and the first woman of color to serve as president of the council. In November 2021, Michelle Wu was elected the first woman and first person of color to become mayor of Boston with over 64% of the vote. At 36, she was the youngest person to be elected mayor of Boston in almost a century.

All three of these individuals presumably had no business becoming who they are today. Andrew Yeung was a product manager at Google and is now a tech socialite. Harry Stebbings was a college dropout who started a podcast and is now running over half a billion dollars in AUM. Michelle Wu was running a tea shop in Chicago to becoming the first woman and first minority to become the Mayor of Boston. None of them asked permission to do what they did and more likely than not, didn’t believe they needed to. They just went out there and took action.

What I Learned

In my own personal experience, the most transformative shifts in my career and life have been from doing things without permission:

When I started my first company, we bootstrapped it and only raised $100K from friends and family. We were able to turn that into millions of dollars in revenue. We didn’t ever take venture capital despite being offered it, because we wanted to control our own destiny. We were fortunate we didn’t have raise institutional capital, which would have meant asking permission to build what we built.

When I created Hyphen Capital as a syndicate to invest in Asian American founders, I had very little experience investing in startups. But I had the network to pool the capital and the talented founders who were fundraising. I didn’t go and get a job with a venture capital firm or go out and fundraise from institutional LPs. I just wanted to help founders out that needed the funding and started writing checks. I didn’t wait for permission to invest $30M in 90+ companies, I just did it.

When we wrote the open letter and bought the full page ad in the Wall Street Journal condemning all the anti-Asian hate crimes after the spa shootings in Atlanta, we didn’t ask anyone’s permission. None of us had ever done or seen anything like it before. We just knew that we had to do something and make a bold statement. We felt invisible and made ourselves visible. We gave a voice to the voiceless because it was necessary.

When we produced 38 at the Garden, the studios all passed on it, because most of them didn’t think people would be interested in Jeremy Lin’s story from nearly a decade ago. The gatekeepers weren’t Asian American and didn’t understand the lasting impact that moment had on so many people in our community and beyond. So I raised the money we needed to make the film. We didn’t ask permission, we just made a film we knew people wanted to see. More importantly we made a film that WE wanted to see. I made the film so that my kids and everyone else’s kids could see that nothing is impossible.

What I learned from each of these experiences was that most of the time in life, if you want something, you have to go and take it, it is rarely handed to you. For some, they inherit it and it is given to them by birth. For the rest of us, we have to have agency and get it for ourselves. This is what separates the have and have nots. You can sit around and complain about not having this job or that life, but if you aren’t doing something about it, why would you assume they should be yours? Taking action creates momentum, and sometimes that’s all you need.

If you are always seeking permission, then you are just waiting for someone to tell you no and give you an excuse not to do it. “I couldn’t start the company because no one would give me capital.” “I didn’t write the book because I couldn’t find a publisher.” “I didn’t make the movie because the studios weren’t interested.” These are all excuses to avoid potentially failing. But they’re also chains to keep you from succeeding. You can start a company without funding. You can write a book without a publisher. You can make a movie without a studio. If you’re serious about doing something and have conviction, you won’t ask permission, you will just do it. Don’t let someone else decide your destiny for you, because that’s a cop out. Make your own destiny.

If you’re an Asian American professional and want to learn more about how to apply these learnings with executive coaching, check out The Asian Leadership Center

Key Takeaways:

🥇 Winners Don’t Always Come from Where You Expect

• The message: You don’t need massive resources or permission to win—you just need to create something great.

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🚀 You Don’t Need Permission to Build Something Great

The essay highlights three standout individuals who succeeded without traditional credentials or gatekeeper approval:

• Andrew Yeung: Turned casual tech mixers into a million-dollar global events business.

• Harry Stebbings: From college dropout to founder of a VC fund managing $600M, built on persistence and a podcast.

• Michelle Wu: From tea shop owner to first woman and person of color elected as Mayor of Boston.

None of them asked permission—they just started.

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💡 My Personal Lesson: Just Do It

• Bootstrapped a startup into millions in revenue without VC funding.

• Started a $30M syndicate (Hyphen Capital) to back Asian American founders with no prior VC experience.

• Co-led an open letter in The Wall Street Journal condemning anti-Asian hate—without institutional backing.

• Produced the film 38 at the Garden when studios passed—because it mattered.

“We didn’t ask permission, we just did it.”

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🔥 Main Message: Take Agency Over Your Life

• Waiting for permission is a trap. It gives you an excuse not to act.

• Don’t let rejection or lack of approval stop you from doing what you believe in.

• Action creates momentum—and sometimes, that’s all you need.

“If you are always seeking permission, then you are just waiting for someone to tell you no and give you an excuse not to do it.”

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💬 Final Thought:

“Make your own destiny.”
If you want something, go get it—because no one’s going to hand it to you.