That night could have been the end of the story. Instead it was the middle of it. Decades before the crash, thirteen-year-old William had landed in Honolulu with a green card pressed into his hand before he’d even cleared customs, then spent high school as one of the only Asian kids in a nearly all-white Huntington Beach, eating lunch alone in the cafeteria. He’d go on to call himself “a loser” for barely graduating USC and failing to get into grad school with his friends — before working his way up to director of sales at 25, only to walk away and start over on his own. This is a story about resilience and perseverance.

In this episode of Hyphen Nation, Dave talks with William about all of it: the crash and the debt collector waiting for him back home who forgave the timeline out of guilt, the two thousand plasma TVs he talked Costco into betting on that sold out in a week and helped found VIZIO, the near-collapse when a $2 billion acquisition fell through in 2015, the 2021 IPO that peaked at a $5.2 billion market cap, the 2024 sale to Walmart for $2.3 billion, and the belief he had to unlearn along the way — that the company was still his — in order to let it grow past him. It’s a conversation about survival, relationship building, and what it actually costs to build something that outlives your ego.

Every boat needs both sails and anchors. Without a sail to catch the wind, a boat can’t take you anywhere. Without an anchor, a boat can drift and crash into the rocks. But an anchor doesn't just prevent the bad outcome. It also prevents every good outcome that requires you to leave the safety of the harbor.

People rely on sails and anchors as well. Sails are anything that helps you move forward on your journey and make progress towards a destination. Sails can be the people in your life that motivate and inspire you. Or they can be the experience and education you build up to give you momentum in your career. Anchors are the people and mentality that keep us grounded, but also hold us back from going anywhere.

Like boats, people need both sails and anchors in their lives. What I have found is that far too many people rely on their anchors more than their sails. They stay in the safety of the harbor, never venturing out to explore or take journeys, because they are afraid of the rough waters. They never find out how far they can go and miss out on the new places that their sails can take them. It’s depressing to think about how many brilliant lawyers, accountants, doctors, and engineers are quietly miserable and have no idea how to leave the harbor they're sitting in.

The Anchors We Inherited

Most Asian Americans and children of immigrants were raised by parents who only taught us how to drop an anchor, but never showed us how to raise a sail. The irony is that they boldly set their sails (some literally) to get here. They relied on anchors, because they had sailed through torrential storms. They left behind their homelands and loved ones, to go to a foreign country where they knew no one, could barely speak the language, and only had a few dollars to their names. They prioritized security and stability over everything. Because anchors were how they survived the storms.

That scarcity mindset kept a generation of immigrant families afloat. It is also, I've come to believe, the single biggest thing standing between a generation of their children and the life they actually want for themselves.

After weathering the violent open waters, our parents settled in calm harbors. They expressed their love to us by not wanting us to endure the same suffering. So they pushed us into careers that would be reliable and pay the bills. Their idea of what is best for us, is to stay in the harbor and play it safe.

Playing it safe isn't actually safe. It's just a bet you've made without admitting you made it. A bet that the harbor will always be calm, that the credentials will always be enough, and that stability is the same thing as security. It rarely is. I've watched people ride the "safe" path straight into a layoff, a burnout, a mid-life reckoning. I also know people who feel trapped in a harbor of their own making. What is the real cost of this “security"?

I frequently get messages from miserable people who are in terrible situations at their jobs, but they can’t leave because they are afraid they can’t find something better. Their identities are inextricably tied to their brand name company or firm. Their self worth is tied to their title. They are worried that no one else will want to hire them. They are scared that they will fail if they go out on their own. They are terrified to leave the harbor. Even though they’ve spent their lives building up their sails with their resumes, they can’t pull up their anchors.

Trust Your Sails

Sails don’t work by fighting the wind, they work by catching it and using its force to go somewhere. A sail requires you to trust something you can’t fully control. That is precisely what a scarcity mindset cannot tolerate, because scarcity thinking believes control is the only thing standing between you and disaster. Scarcity thinking gives you the false sense of security that if you eliminate any risk or uncertainty, that you are in control.

But I’d argue the opposite is true. The people I’ve watched build real, compounding, exponential lives: the founders in my portfolio, the executives I’ve profiled on my podcast, the friends who left “safe” careers to become writers, investors, builders, didn’t succeed because they controlled every variable. They succeeded because at some point they stopped asking permission and raised the sail anyway, trusting that the wind would take them somewhere even if they couldn’t chart the whole route in advance.

I didn’t ask permission to start a syndicate to invest in Asian American founders. I didn’t ask permission write a letter in the Wall Street Journal letter signed by CEOs and a former president. I didn’t ask permission to finance a documentary that would win an Emmy Award. I didn’t ask permission to start a fund or build a media platform out of nothing. Every one of those was a sail, not an anchor. None of them were safe. All of them compounded into the next opportunity, and the one after that. None of this could have happened while parked in a harbor, avoiding the unpredictable open seas.

Honoring the Anchor, Choosing the Sail

Morris Chang was 55 when he started TSMC. He was a VP at Texas Instruments, where he was respected and compensated handsomely. But after being passed over for the CEO position, he decided to move back to Taiwan, where he pioneered the dedicated semiconductor foundry business model, allowing tech companies to outsource chip manufacturing. TSMC is now worth almost $2 trillion and is the backbone of the AI boom.

On the flip side, Sarah Guo was named general partner at Greylock Ventures at the age of 28. She was the youngest ever GP since the firm was founded in 1965. Instead of staying at a prestigious firm with lucrative carried interest, she left to start her own fund aptly named Conviction. She has gone on to invest in 6 of the 21 AI-native companies that are valued at over $10 billion on revenue run rates above $100 million.

Both Morris and Sarah had the security that every immigrant and child of immigrants longs for. They were already financially successful and had extremely respectable positions. But that wasn’t enough to satisfy either of them. They didn’t want to set their anchors down, because they weren’t done writing their stories yet. Their success, their networks and their reputations were massive sails that they leveraged to take them even further.

Surround yourself with people who will be your sails: People who encourage and support you to pursue your big dreams. People who will indulge you in your crazy ideas. People who will make introductions to others who can facilitate and enable those ideas to become reality. People who have gone ahead of you on that same path who can mentor you. People who will invest in you and believe in you. People who will celebrate your success and not begrudge you for it.

None of this is a rejection of our parents sacrifice. In fact, it’s a direct result of their love and scarcity mindset, that we can even consider these options. I’m not saying you should cut your anchors loose, because you will always need them. You just need to know when to use them to weather real storms. Stop using anchors as a crutch because you’re afraid of what will go wrong. Those are the hypothetical storms we create in our own heads to avoid opening our sails, because we’re so afraid of where they might take us.

Apply for that new job. Move across the country. Move to a new country. Make that career change. Start that new business. Write that book. Create that content. Every choice you make can take force your sails in a new direction, but first you have to open them.

You only have one life to live. It seems a waste to spend it anchored in a harbor just to avoid uncertainty. Imagine if you raised those sails that you’ve invested your entire life building up, how far could they take you? The networks you’ve created. the experiences you’ve had. The skills you’ve learned. You are more than equipped to navigate the unpredictable waters. You may not know where the wind will take you, but that’s what makes life an adventure.

What are the anchors in your life that are holding you back? What are the outcomes that you’re missing out on outside the safety of the harbor?

You owe it to yourself to raise your sail and find out just how far you can go.

In this episode of Hyphen Nation, Dave Lu sits down with his longtime friend Yul Kwon — Survivor: Cook Islands champion, former FBI advisor, ex-McKinsey consultant, and now a VP at Google — for a conversation that goes far beyond the show. Yul opens up for the first time in detail about growing up in Concord, California, as the child of Korean immigrants: a childhood marked by racist bullying, undiagnosed OCD, severe social anxiety, and a private, deeply shameful condition called paruresis (shy bladder syndrome) that shaped nearly every decision he made — including almost keeping him off Survivor altogether.

Yul traces the full arc of his life: a bullying incident in elementary school that triggered decades of hidden struggle, the loss of his best friend Evan to leukemia at Stanford (and the bone marrow donor registry campaign it sparked), his pivot from law and public policy to McKinsey and Google, his winding path to Survivor, and the personal reckoning that came with sudden fame. He also shares the “competence, integrity, benevolence” trust framework he now uses to build relationships at work and at home, and reflects candidly on why so many Asian Americans are trusted to work hard but not trusted to lead — and what it takes to break that pattern.

This is a conversation about identity, mental health, and the difference between being liked and being trusted — from someone who spent years hiding his story before deciding to use his platform to tell it.

Topics covered:

• Growing up in Concord, CA as a child of Korean immigrants

• Undiagnosed OCD, social anxiety, and paruresis (shy bladder syndrome)

• A childhood bullying incident and its decades-long psychological impact

• Losing his best friend Evan to leukemia at Stanford, and organizing bone marrow drives for the Asian American community

• The path from Stanford → Yale Law → Capitol Hill (Sen. Joe Lieberman) → McKinsey → Google

• Nearly turning down Survivor because of his hidden condition

• Becoming the first Asian American to win Survivor, and the disorientation of sudden fame

• Being named one of People’s “Sexiest Men Alive” and navigating stereotype-breaking visibility

• The “competence, integrity, benevolence” framework for building trust

• Why Asian Americans are often trusted to be hard workers but not trusted to lead

This is a photo from 2007 that I took with Anne Hathaway, who plays Penelope. We were both shopping at the same store in the West Village in New York. She was shopping for Christmas gifts and we started chatting. This was after The Princess Diaries and the same year The Devil Wears Prada had come out, so I obviously knew who she was. But I talked to her like any other person, because at the end of the day, she’s running errands like anyone else. After we talked, I asked if she would take a photo with me and she happily obliged.

Recently, an extremely influential and powerful friend of mine in the sports industry, was with me in a room full of billionaires and industry titans. We’ve been friends since we were in business school in our mid-twenties, so he’s seen me in many situations. He asked me after we left the room how I was so comfortable in that room just floating around from person to person like it was nothing. He said he even he still gets intimidated around people like that, even though he’s around NFL owners and players all the time.

I told him, they’re all just people. No one is better than anyone else. They each have their own stories and journeys. Some people are born into money and power, and other people find their way to it. But that doesn’t change the fact that they worry about their loved ones, they worry about their health, they still have fears and insecurities, and are still human. At the end of the day, famous or rich, they still want to be treated with respect and care.

I find that too many people make themselves small when around other people. They think they are not worthy or that they have to defer to someone else. That makes people either feel uncomfortable or it makes them feel superior to you. And that is never a good position to be in. People can take advantage of you when you put yourself in a position of weakness. Whether it be at your job, negotiating the price of a new car, or in a relationship. Always be your full self and don’t change that because of who you are with.

When people feel superior to you, they can be dismissive at best, or abusive at worst. They can use that power to intimidate and take advantage of you. It could be a bad manager who takes credit for your work. It can be a spouse who controls you. People abuse positions of authority all of the time if you let them. This is why it’s so important to know your self-worth and remind yourself that they are just a person like anyone else. When stranded on a desert island, without their money, fame or titles, they are just as vulnerable as you are.

People will respect you more when you respect yourself. The sooner you realize this, the more powerful you will be.

In this episode, Julie opens up about growing up as one of the only Asian kids in Northeast Ohio, living a “double life” between her American school friends and her tight-knit Korean community, and the pivotal moment at her mother’s funeral that reshaped how she thought about leadership and relationships. She shares the hard feedback from a mentor that pushed her to “lead from the front,” how she learned to manage being an introvert in the spotlight, and why staying true to herself — not conforming to a stereotype of what a CEO should look like — is what got her to the top.

A conversation about identity, quiet resilience, and redefining what leadership looks like.

In this episode, Neela shares how her early experiences growing up in the UK’s immigrant community taught her resilience, cultural agility, and the importance of authentic communication. You’ll discover how her backgrounds—an English literature major turned marketing strategist—became her superpower in leading diverse teams and turning around brands. She breaks down practical tactics: how to raise your hand for leadership opportunities, the importance of managing P&L to reach executive levels, and why embracing tangents in your career can unlock unexpected growth.

We also explore the often-overlooked organizational nuances—how navigating cultural gaps, political savvy, and code-switching are critical for success in global and diverse environments. Neela emphasizes the value of mentorship, building a network, and being relentlessly curious beyond your comfort zone—especially for Asian-American professionals seeking to break ceilings or those eager to lead with impact.

Why does storytelling matter most in leadership? Because it creates trust, aligns teams, and influences decisions—especially when managing complex challenges like the COVID vaccine rollout or navigating market disruptions. Neela’s insights on embracing imperfection, taking risks, and prioritizing significance over success are invaluable for anyone aspiring to elevate their career and influence.

This episode isn’t just a career deep-dive—it’s a masterclass on authenticity, resilience, and strategic storytelling as essential tools for modern leadership. Perfect for business leaders, aspiring executives, and anyone eager to make an impact while staying true to themselves.

I’ve recently been seeing many social media posts from friends who attended Cannes Lions, the world’s largest and most prestigious annual gathering for advertising, marketing and creative communications industries, that is held in Cannes, France. It looks exactly like it sounds, big budget parties and soirees on the French Riviera with celebrities and influencers. It’s a place where advertising executives and social media influencers are hanging out with Oprah, EJAE and Kevin Durant. It’s one giant networking event where brand deals are cut and where valuable connections are made. Most people believe these events are impactful because you’re meeting important people at exclusive parties. What is far more powerful and transformative is the moment when you realize that you have always belonged in those same rooms.

Making Yourself Bigger

Cat Goetze (askcatgpt), a social media influencer, compared going to Cannes Lions to attending Stanford. Many people who have not experienced both or either might think that this is an absurd statement. I haven’t been to Cannes Lions, but I’ve had many similar experiences like the Milken Global Conference among others. And I think her assessment is accurate.

When I was accepted to Stanford business school, I thought that it had to be a mistake and that I didn’t deserve to be there. I suffered from self-inflicted imposter syndrome, and believed that I didn’t belong in a class of such incredibly accomplished people. But when I finally got there, I realized that I was just as capable as anyone else in my class of doing great things. I learned that even the most accomplished people have insecurities and flaws. It was as if I was a teenager wearing an adult suit that didn’t fit well, and I grew into the suit. My brain was rewired into believing that anything was possible, just because I was in the same classrooms with others who believed that to be true. Even the professors were telling us the same, teaching us through stories of regular people who accomplished great things in case study after case study. Our brains were rewired to believe in ourselves and take bold risks in life. It helped to have a cohort of peers who shared that unique experience and belief as we graduated together to the real world.

Attending conferences or events like Cannes Lions or Milken, you have a similar experience. Perhaps not as extended as two years of business school, but a powerful condensed version. You are chatting at cocktail parties with world class athletes and celebrities and sitting at panels next to prominent executives and billionaires. You are literally in the same room as some of the most successful people in the world. At first, your instinct might be to shrink and act like a wallflower, because you think you’re a fraud and shouldn’t be there. But once you realize that there was a reason you were invited to be in that same room, something clicks. You were invited to be in the same place that they are. You are not there by mistake. Those people are not better than you. You have just as much value as they do. You might bring something different to the table, but you are sitting at the same table.

Once you’re over your pinch yourself moments, it starts to sink in that you belong. And your view of yourself changes. You start to feel a little bigger and more confident. Your aspirations grow and your ceiling for yourself starts to rise. A funny thing happens when you allow yourself to grow to your full potential. Other people notice, and they start to invite you to more of these rooms. And as you build more connections and confidence, you start to see opportunities materialize that weren’t there before. New levels of the game appear before your eyes. You are no longer bound by the same self-imposed limits of what is possible.

Making Yourself Smaller

My friend Yul Kwon has had one of the most circuitous careers of anyone I’ve ever met. Growing up, he was a shy and scrawny Korean kid in Concord, California. He went to Stanford and while he was there his childhood friend and roommate, Evan, was diagnosed with terminal leukemia. Yul organized a nationwide bone marrow campaign to help find a bone marrow donor and successfully found a match. Sadly, the procedure ultimately failed and Evan died two years later. Yul would go on to graduate from Yale Law School, before working as an aide to U.S. Senator Joseph Lieberman and clerking for a Appellate Court. Instead of joining a law firm, he went into the private sector and was a consultant for McKinsey and worked in strategy at Google. He essentially had the resume of every Asian American parent’s wildest dreams and every Asian American kids worst nightmare.

In 2006, Yul was recruited to compete on the thirteenth season of Survivor. He ended up winning Survivor: Cook Islands. He became an instant celebrity and a high profile Asian American. After his victory, he lectured at the FBI Academy while also becoming a Red Mango frozen yogurt franchisee. He ended up taking a job as Deputy Chief at the FCC, before taking a year off to host the PBS series America Revealed and become a news host on LinkAsia. In 2013, he returned to Silicon Valley and became a product management director at Facebook and is now a VP of Product at Google.

Needless to say, Yul has seen a lot more than most people in his lifetime. He has had exposure to medicine, law, business, technology, entertainment, and government throughout his career. We caught up recently, and he brought up an interesting observation: When given a role that is big, Asian Americans will step up and grow into the role. They will rise to the occasion to meet the demands of the position. Alternatively, when they are given a role that is too small for them, they will shrink themselves to fit that role. Rather than show their true ability or shine beyond the role, they will make themselves small to accommodate their managers and peers.

Because so many Asians are raised to follow the rules and accommodate others, they are not comfortable with pushing boundaries or crossing lines. It’s a transactional mentality of “do the task that you were asked to do, no matter how big or small, and don’t complain or ask questions about it.” That translates extremely poorly to the workplace, where if you are overqualified for a job, you don’t say anything. You accept what is given to you and hope that someone will give you more. You essentially wait for permission to live up to your full potential, instead of giving yourself permission.

Yul is still the same shy kid from Northern California. That didn’t stop him. Time and time again, he’s gotten himself into those rooms. He believed he deserved to be in those rooms and no one was going to tell him he didn’t belong. Yul filled every suit he tried on.

So many people think that we are limited by our capabilities and talent, when in reality it is our belief in ourselves that holds us captive more than anything. When you don’t give yourself permission to take risks or to fail, how can you succeed? When you make yourself smaller to fit in someone else’s box, you are only cheating yourself. You cannot accept being a victim, because you have the agency to break out of that box. Sometimes we really are our own worst enemies. Not everyone will get to attend Cannes Lions or Stanford, but hopefully they will get to experience a similar unlock at some point in their lives.

Find your way into the right rooms and I guarantee you will never be able to look back again.

We talk about:

• Growing up as one of the few Asian Americans in his hometown

• The sacrifices his immigrant parents made and the entrepreneurial lessons he learned from them

• Why he walked away from a traditional engineering career

• The power of relationships, mentorship, and playing the long game with your network

• How to discover work that genuinely energizes you

• Why too many people stay on the “default path” instead of pursuing what they truly want

• The early struggles of Gamma and the lessons learned when growth stalled

• Building conviction as a founder when everyone doubts your idea

• Leadership, storytelling, and what Asian American professionals can learn from leaders like Jensen Huang

• Why it’s never too late to reinvent yourself and pursue your life’s work

Grant’s story is a powerful reminder that success isn’t about following someone else’s definition of achievement. It’s about finding the work that gives you energy, having the courage to leave your comfort zone, and taking ownership of your own path.

Whether you’re a founder, creator, aspiring entrepreneur, or simply wondering if there’s more to your career than the path you’re currently on, this conversation will challenge you to think bigger about what’s possible.

Last year, I visited Stanford Business School, my alma mater, and stopped by Professor Jeffrey Pfeffer’s renowned class Paths to Power. Professor Pfeffer is widely regarded the leading expert on power and has published multiple books on the subject including Power: Why Some People Have It and Others Don’t and 7 Rules of Power: Surprising—but True—Advice on How to Get Things Done and Advance Your Career.

I was speaking on a panel later that afternoon, and decided to sit in on his class before having lunch with him. He started the class by announcing that I was a special guest and praising me for all the things I’ve done and how famous I was, before asking me to introduce myself. I wasn’t expecting to be introduced and shyly played off my accomplishments. Professor Pfeffer wasn’t having any of it. He promptly reprimanded me in front of a class about power, for making myself seem small. He said that many people will brag about things they never really did, and I won’t even talk about the amazing things I actually did!

It was a vivid lesson I will not soon forget.

Asians tend to internalize their failures and externalize their success, because of their upbringing. This is rooted in a culture of saving face and avoiding shame. Parents focus on your flaws, not your strengths, and rarely provide positive reinforcement or praise for success, because success is expected. When you do something well, you are reminded that someone else did it better. So whenever you have a big win, you tend to ascribe it to luck or other people. Although if things go wrong, you tend to blame yourself for the outcome. You won’t take credit for the good, but you always take credit for the bad. This leads to a lot of negative self-talk and misguided imposter syndrome. It creates self-doubt and a lack of confidence that is detrimental to your identity.

For some people, this attribution is reversed. They place the blame of failures on others or to unfavorable circumstances. Meanwhile, they are willing to take full credit for any and all successful outcomes, even if they weren’t responsible for them.

When you own your successes, you build self-confidence and pride in yourself. You carry yourself differently when you walk into a room. You act like you deserve to be in that room and others can tell. You sit at the head of the table, because why wouldn’t you? You contribute heavily to the conversation, because you believe that what you have to say needs to be heard. You have what they call “executive presence”.

When you beat yourself up constantly over small mistakes and give away credit for your success to others, you make yourself smaller and smaller. You walk into a room feeling “grateful” to be included. You sit on the outside chairs, because you want to let the more important people have a seat at the table. You don’t want to draw any attention to yourself, because you are afraid you might say something wrong.

Who do you think is more likely to be promoted to an executive someday? Who would you promote if you were a board member, shareholder or CEO?

Sometimes it doesn’t matter if you’re always right, it matters if you’re willing to speak up. People have to be willing to buy in to what you are selling. If you don’t believe in what you are selling, why should anyone else? Especially if what you are selling is yourself.

Cultural Programming

When you grow up in a household where you brought home a 97% on an exam and your parents ask what happened to the other 3% instead of praising you, it’s not hard to understand where this self-sabotaging mindset comes from. You never think that you are good enough, because nothing is ever good enough. Even getting a perfect score on the exam gets you a lukewarm response because that is what is expected. It is difficult to feel very special when you never receive any positive reinforcement as a child. You begin to focus on all the negatives and internalizing any failures. Your self critic becomes deafening and needs to be shut down because it is harmful.

You rarely if ever hear, “Good job, you gave it your best!” in an Asian household. In fact, even when you do succeed, you are reminded that someone else did it better. Nothing seems to impress parents, even when you so desperately want to earn their love and respect by performing well. They want you to succeed, but not to get too cocky when you do. This doesn’t mean that they don’t love you, they just show it very differently.

Meanwhile, in other households, you are encouraged to try things and praised for effort, even with mediocre results. When you are raised with positive reinforcement, you carry that attitude with you throughout your life. When your parents vocally cheer you on and instill confidence in you, you start to believe anything is possible. When your opinion is valued and heard at a young age, instead of always deferring to your parents, you are more likely to believe your opinion matters. Instead of being made to feel small, you are made to feel big.

Like many Asians, I was raised to be humble and to think of others before myself. Arrogance and drawing attention to yourself are frowned upon in Eastern cultures. That’s why we instinctively deflect credit to others before accepting any ourselves. But I’ve learned that humility doesn’t mean minimizing yourself or becoming invisible. You can be aware of others, while still being fully yourself. When you shine your light, it doesn’t drown out others light. Everything just gets brighter.

The Power of Owning Success

It is hard to beat a team that is on a win streak. They build momentum and confidence, which compounds into more wins. People underestimate the impact of self-belief. Knowing you have the talent and ability gives you a certain boldness and audacity to take on bigger challenges.

In order to have self-belief, you need to give yourself credit when things go well. You have to own it. You have to say it out loud. Don’t play it down for others. Don’t minimize your success. Don’t give away credit that you deserve.

Being raised to deflect attention and play off success with words like “it was nothing” or “it could have happened to anyone” is detrimental. Self-deprecation is self-sabotage. By diminishing your accomplishments you only end up hurting how others perceive you. They will believe you when you say it wasn’t a big deal or that you got lucky. Instead, simply acknowledge the hard work you put in or the fact that you are very good at your job. It isn’t arrogant if it’s accurate.

The Danger of Internalizing Failure

When you turn external setbacks into personal flaws, you turn “I made a mistake” into “I am a failure.” Self-blame turns emotional distress inward, often leading to negative self-talk, anxiety, and reduced motivation. You overgeneralize a setback as proof that you will never succeed, so you give up trying again. You fall into the trap of focusing entirely on internal and unchangeable traits (talent and intelligence), while ignoring external factors.

While some unreasonable people always blame external circumstances for everything that goes wrong for them, and never take ownership, it is entirely valid to look at external circumstances. Things like timing, bad luck, or other systemic issues are out of your control and always in play. It is irrational to believe that you can be 100% responsible for any outcome.

Many Asians I know are deferential and play defense. You tell yourself that it’s okay if things don’t work out because you’re hedging against failure. You’ve been beat up so much growing up that you use this as a way to cope with bad outcomes. You inevitably suffer from imposter syndrome because you continue to focus on and magnify the 3% you missed, not the 97% you got right. You have all the talent and ability in the world, but none of the confidence, because you have been programmed to fixate on the flaws.

A prime example of how this plays out in the real world is when you are looking for a job. If you suffer from this failure fixation mentality, you will see a job posting and not apply because you only hit 7 of the 10 bullet points listed in the job requirements. Meanwhile someone else who only meets 3 of those bullets will have all the irrational confidence and self-belief in the world to apply. They honestly believe that they are capable of doing all 10 even if they haven’t before. These individuals aggressively play to win, they don’t play not to lose. This shift in mentality makes a huge difference not only in self-perception, but ultimately how others perceive them.

The real world isn’t a meritocracy. Self-perception often drives reality.

How to Shift Your Perspective

When you’ve spent your whole life beating yourself up over mistakes, it’s hard to change. Here are some ways to catch yourself from internalizing failures and mistakes by reframing them:

Separate Behavior from Identity - Recognize that failure is a data point, not a verdict on your self-worth. It’s always helpful to see yourself as a third party. If a friend was in this exact situation, would you tell them they are a failure, or help them to see what went wrong? Would you beat them up over it? We would never do this to someone else, so why do we do it to ourselves? One mistake or outcome does not define who you are.

Name the External Factors - Step back and evaluate the situation objectively. Acknowledge the uncontrollable factors (environment, resources, others’ actions). that contributed to the outcome. The more you are able to understand why you failed, the less likely you are to internalize and blame yourself. Doing this actively allows you to reframe your negative self-talk. It gives you the opportunity to learn from the situation and grow from it, instead of merely chalking it up to a “you” issue.

Limit the Scope - It’s always helpful to put things in perspective. When you take a failure in one area (not passing a test, a presentation going badly, a disappointing job interview), it is easy to project that to everything else in your life. Shrink the impact of your setbacks, because these incidents are just that, isolated events. They do not define you or your worth.

The process of changing self-perception takes time. Be kind and patient with yourself as you transition your mindset into one of self-belief, so give yourself a lot of grace.

I am obsessed with golf. I discovered it in my mid-thirties and spend any free time I have playing golf. There is something about playing a game where it’s just you vs. yourself. When you hit a good shot, you take full credit for it. When you hit a bad shot, you can only blame yourself and not an opponent or a teammate. But my friends have always told me that whenever I hit a good shot, I still manage to find something wrong with it or say I got lucky. And when I hit a bad shot, I beat myself up and become so negative that it compounds into more bad shots.

My golf game is a metaphor for this essay. I won’t take credit for the good, and I beat myself up for the bad. I constantly think I have a bad swing that gets lucky with some good shots every now and again. Whereas a good golfer has the confidence to trust their swing, even if they occasionally make bad shots which are the exception. They let the mistakes roll off their back like it’s no big deal, because they are anomalies. They don’t suddenly think they’re bad golfers because they hit a bad shot.

Even though I still struggle, I am doing my best to trust my swing with confidence because I know I hit far more good shots than bad. And when I do hit a bad shot and make a mistake, I learn from it and move on. There’s no sense in dwelling on it, because it’s done and I can’t do anything about it. I just need to regather my confidence so I can hit the next shot. My game has improved so much because of this positive shift in self-perception.

Trust your swing, because even if it feels lucky, it’s still all you.

Learning how to shift your mindset from owning your success and accepting your failures takes time and effort. That’s why so many people have executive coaches to help point out the self-sabotaging thoughts and behaviors. It’s why I encourage so many people to seek out coaching, because it’s the best investment you can make in yourself and your career. All of these things like having a growth mindset, embracing conflict, pursuing power, not being so transactional, having main character energy and the importance of storytelling, are a process. We are all works in progress, but we have to be self-aware enough to recognize that the work has to start somewhere.

One of the greatest American investors of all time, Charlie Munger, only trusted his own money with one other investor: Li Lu

Everyone knows the names of Berkshire Hathaway legends Warren Buffet and Charlie Munger. But few people know about Li Lu.

Munger referred to Li as the "Chinese Warren Buffet" in a 2003 Financial Time profile. They met at a Thanksgiving dinner in 2003, which began a lifelong mentorship and friendship. When Li launched his new fund Himalaya Capital the next year, Munger entrusted him with $88 million. Li grew that to 4-5x by 2023.

"In my life, I've given money to one outside manager, and that's Li Lu," he said. "No others in my whole life. And I have no feelings that it would be easy to find a second."

In 2002, Li famously invested in Chinese automaker BYD in 2002, when it was still a battery maker. His conviction led Berkshire Hathaway to purchase a 10% stake in 2008 for $230 million. BYD went onto become the world's biggest EV maker. Berkshire has cashed in an estimated $8.4 billion on the investment since then.

But most people don't know his story. Li was born in China to an engineer and botanist in April 1966. One month later, Mao Zedong’s Cultural Revolution would begin and his parents would be sent to labor camps for being intellectuals. His parents were able to pay other families to take him in. He would eventually be reunited with his parents after they were “rehabilitated” but he felt distant from them.

After surviving the Cultural Revolution, one of the deadliest earthquakes ever (7.6 magnitude) struck his home of Tangshan. It was so bad he thought they had been hit by a atomic bomb. It was the third deadliest earthquake in history with over 242,000 killed including all of the members of Li’s adopted family. He was only 9 years old.

In 1989, Li was a 23 year-old student from Nanjing University protesting in Tiananmen Square, when the government violently cracked down and stormed the students. Student leaders estimate that up to 3,400 civilians were massacred that day. The government named 21 students for leading the uprising and Li was one of them. Li went into hiding and managed to be smuggled to Hong Kong and then to France.

With no money and unable to speak English, he was granted asylum in the U.S. He would make his way to New York, where he was supported by other human rights activists like Robert Bernstein, the CEO of Random House, who helped him get settled. And Trudie Styler, who gave Li her husband’s second-hand clothes. She was married to rockstar Sting and would later produce a documentary about Li’s life.

He would learn English over the summer and enrolled at Columbia where he became one of the firsst students to simultaneously earn a bachelor's, JD and MBA. After attending a lecture by Warren Buffett, Li started investing his student loan money in the stock market with significant returns.

After working at esteemed law firms and investment banks, he was encouraged to start his own fund in 1997. With $2M of capital from a real estate magnate he met while giving a lecture, he started Himalaya Capital. Today, Himalaya manages an estimated AUM of $15-20 billion.

In 2021, amidst the rise of anti-Asian hate during the pandemic, Li rallied fellow prominent Asian American business leaders Jerry Yang, Joe Tsai, Joe Bae and Peng Zhao to found The Asian American Foundation. TAAF was established to combat the severe historic underinvestment in the AAPI community, which traditionally received less than 0.5% of charitable giving from foundations.

This past week, I got to spend some time with Li Lu at the fifth annual TAAF Heritage Month Summit attended by 1,000 leaders from around the country. The summit featured panels of influential AAPI leaders like Sunisa Lee, Min Jin Lee, Andrew Yang, Neal Mohan, Jeremy Lin and Vera Wang among others. It was inspiring few days of community and fellowship, made possible because of an idea Li had five years ago.

Li Lu suffered losing his parents as a child, surviving a devastating earthquake, fleeing communist persecution, and rebuilt his life from nothing to become one of the most successful investors in the world. And now he's started a movement to empower AAPIs.

He never allowed his circumstances deter him from writing his own story. From getting on that train from Nanjing to Beijing in 1989. To moving to New York without knowing the language or a single person. To starting his own fund and making bets on a country he wasn’t allowed to return to. Li has continued to live an exponential life, and still has more of his story to write.

Most people live a linear life: They go to college, get a job or go to graduate school, work hard to get a promotion, save up for vacations, and repeat until they retire. Every step is predictable and safe. This is why so many immigrant parents push their children to get into the best college, because it puts them on track for the highest potential salary. The higher the salary, the more financially secure and stable their lives will be. All these tracks are linear. You take one step after another in a straight line to get to your final destination: death.

I’ve often equated this linear life to playing Super Mario Bros, an old Nintendo game where there is only one way to complete the game. Like most linear games, you sidescroll through level after level beating bosses to get to Bowser, the final boss, to save the Princess. There are no shortcuts and you can’t deviate from the path, because it was designed that way.

In terms of the real world, this is like becoming a doctor. You go to college, you take your pre-med requirements and MCATs, you go to medical school, you get matched into residency, you might do a fellowship to specialize, you get hired at a hospital or private practice. You are literally on a track your entire career. It is quite possibly the most meritocratic career you can choose, because your scores and performance get you to the next level. Your MCATs, your medical boards, your medical licensing exams are all the bosses you have to beat to progress in the linear game of medicine.

In contrast, Grand Theft Auto is a game with an open world. You can freely choose where you want to go and what missions you want to complete. You can also choose not to participate in missions and skip them. You can literally win the game and not finish every mission, which is very different from Super Mario Bros., where you can’t progress without finishing each level.

Growing up, I was raised to believe that I couldn’t skip levels. I was told that I have to go to an Ivy League school, get a prestigious internship, get an MBA from Stanford or Harvard, and work to become a VP at a big company, before I could even consider starting my own company. This was all a lie. I could have started a company out of high school, but instead I chose to follow the linear track that was laid out before me. I was told I needed to pay my dues and get years of experience before I could pursue my dreams.

The Chef

Many young chefs that were told that they had to “pay their dues” in established kitchens before they could open their own restaurants. The old school thinking is that you can’t possibly be a good chef if you haven’t done your time and learned from the best. Now we’ve seen what it’s like to “learn from the best.”

Meanwhile, I’ve watched young chefs like my friend Kwame Onwuachi rise to the top of the culinary world and open the best restaurant in New York. He staged at some of the best restaurants in the world like Eleven Madison Park and Per Se, but he didn’t spend years toiling away in those kitchens. After being on Top Chef, he developed his own style of Afro-Caribbean cooking and took a risk to open a restaurant in DC that failed spectacularly, but he didn’t give up and followed it up with a wildly successful restaurant. The secret? He stopped trying to emulate what other chefs were doing and started being true to himself.

Kwame no doubt has detractors and haters who say he never did his time. But does it matter if he didn’t complete every level of the game before he beat the final boss? He skipped all of the levels he was told he had to complete to get there and he ultimately won the game anyway. Now he has a New York Times Bestselling autobiography that is being adapted by A24 into a feature film, Notes from a Young Black Chef. He has brand partnerships and collaborations with American Express, Lexus, Motorola. His followup restaurant Dōgon in DC is critically acclaimed and he is opening another restaurant in Las Vegas with Sahara.

Kwame is living the exponential life. Instead of going step by step, he carved his own path to achieve is dream. It’s like he used a cheat code in life. Except the only cheat code is not following the standard protocol accepted by everyone else. Consensus is that you are required to check off all of the boxes before you get to the top of the mountain. But according to who? Just because everyone says you have to climb the mountain, doesn’t mean you can’t take a helicopter and end up in the same place. You don’t need permission from anyone but yourself to live the exponential life. It is a choice.

Some people are born into the exponential life by inheriting wealth or being a child prodigy. The rest of us have choose to pursue it ourselves. You go down the path less taken. You don’t accept the status quo. You don’t believe in limits. You are willing to fall and get back up again and again, because you refuse to fail. You are fine being bad at something so you can get good at it. You want to be inspired and pursue your passions. You have a purpose and a mission that drives you to want to leave an impact and legacy that goes beyond yourself.

The Fashion Designer

Vera Wang spent her entire childhood training to be a figure skater for the Olympics. She began skating at the age of eight and competed in the U.S. Figure Skating Championships but failed to qualify for the U.S. Olympic team. After going back to school, she earned a degree in art history from Sarah Lawrence College and joined Vogue upon graduation. She eventually became one of the magazine’s youngest-ever senior fashion editors.

After spending 17 years at Vogue, she finally left in 1987 to serve as a design director for accessories at Ralph Lauren. While searching for her own wedding dress, she became frustrated by the lack of options and opened her own bridal gown boutique at the Carlyle Hotel in 1990. She has made wedding gowns for Mariah Carey, Chelsea Clinton, Kim Kardashian, Vanessa Hudgens, Victoria Beckham and many more. She also designed costumes for figure skaters worn at the Winter Olympics for Nancy Kerrigan, Michelle Kwan, Evan Lysacek and Nathan Chen. Although it wasn’t for her figure skating, Wang was inducted into the U.S. Figure Skating Hall of Fame in 2009 for her contribution to the sport as a costume designer.

Wang would eventually build an empire from her brand. She opened bridal boutiques in New York, London, Tokyo, Seoul and Sydney. She expanded into fragrance, eyewear, homeware and shoes. She went from selling high-end wedding dresses to partnering with David’s Bridal to sell more affordable bridal gowns and with Men’s Wearhouse to sell tuxedos. Her namesake brand would catapult her into one of America’s richest self-made women, worth half a billion dollars.

There are countless stories like these, of successful people who refused to live a linear life. What they all had in common:

• No Limits. Never allow others to tell you what you can and can not do. People project their own fears and insecurities, and rarely have firsthand experience.

• Reframe Failure. Every mistake or failure is a learning opportunity that you can build upon. You must persevere or pivot and find another way.

• Compounding Experiences. Each experience is additive and contributes to your future endeavors. The more experiences you have, the better.

People choose to live linear lives, because they are much safer and more stable. Many who live exponential lives are only able to because they are born into wealth, which gives them a safety net to take risks without fear of failure or negative consequences. It’s much less intimidating to live an exponential life when you know you can keep trying again and again, because you have nothing to lose.

If you come from an immigrant or lower income family, however, you cannot afford to take as many swings. You are raised with a scarcity mindset to seek a life of security and stability, because the alternative would be disastrous. You become a trained and obedient workhorse, who is rewarded with carrots for doing a good job. You study hard and get good grades, so you can please your parents and get into a good college. You work diligently in college so you can get a high-paying job. You do everything asked of you at work so you can get promoted. But when you hit that ceiling, you are confused because you aren’t getting the recognition you are used to receiving for doing what you’re told. No one is giving you a carrot any more and you feel cheated. But you haven’t demonstrated any leadership potential, because all this time, you’ve just been good at jumping through hoops and following orders.

Fleas in a Jar

What holds people back is not the fear of not having enough, but believing that they themselves are not enough. When they are off the beaten path, they are confused and uncertain, because they’ve followed the path laid out for them their entire lives. When you go from Super Mario Bros. to Grand Theft Auto, you have no idea what your next mission is or how to make progress, because it’s not obvious. If you were raised to follow the rules, this will feel uncomfortable, because no one taught you how to choose.

All of your life you’ve been raised to achieve success in the eyes of the world, which usually is some form of financial wealth, because that is what is measurable. But what if success for you looks different? What if you defined what a successful life is on your terms?

What if success is being able to:

• spend more time with your family

• create art or music that stirs people’s souls

• teach others how to be their best selves

• travel the world with a backpack of your belongings

• do research that helps cure cancer or disease

When you reframe what success looks like for you (not for others), it might not actually be that far off.

Fleas are able to jump vertically up to three feet in the air. When they are placed in a jar with a lid, they strike the lid when they jump and fall back down. After about three days, they are conditioned to stop jumping as high to avoid hitting the lid. They have adapted their behavior based on their circumstance and environment and have effectively capped their own potential. When the lid is removed, the fleas continue to jump below the height of the now non-existent lid. Even if new fleas are introduced or new generations are born, they inherit this limited, conditioned before, acting as if they are still constrained.

Though this is only metaphor, it applies to people who have been conditioned by invisible limitations that are placed on themselves. They tell themselves that these ceilings have been holding them back, but ultimately these are excuses for not making certain choices that they have to own. They don’t know how high they can go, because they’re unwilling to even attempt breaching their self-imposed boundaries, for fear they might “fail”. This results in imposter syndrome, especially for immigrants, minorities and women, which is a rational response to a system that wasn’t designed to benefit them. You are not broken, you have been accurately reading a room that was designed to make you doubt yourself.

Just as we must define what success looks like for ourselves and not for others, we need to understand why failure makes us so afraid. For some it is the shame. Shame is something we feel when we care too much about how others perceive and judge us. In reality, we are in control of feeling shame. Being shameless is often seen in a negative light. But being shameless makes you bold and fearless. For others it is fear of ending up empty-handed. If failure is based on opportunity cost or financial anxiety, ask yourself what the real cost is. How much do you really need to give yourself a shot? You built up that resume for a reason, do you really believe you couldn’t get a job if things don’t work out?

Most people have an inner voice that tells them why they can’t do something. Instead, try asking yourself: Why not me? You need to stop believing that successful people are somehow born “special” and different from you. Kwame Onwuachi was a kid from the Bronx that sold candy bars on the train. Vera Wang was a figure skater who didn’t make the Olympics. They made choices along the way that changed their trajectory from linear to exponential.

AI Changes the Equation

The world is rapidly changing with uncertainty around how AI will upend different sectors and industries. Jobs that seemed safe and secure choices in the past, will be obsolete. Anything that can be automated will likely be replaced by agents: lawyers, accountants, bankers, doctors, engineers, etc. All of these were careers that were pushed by immigrant parents because they were a surefire way to earn a good living. They didn’t require taking any risks, just keeping your head down and working hard. The very reason these jobs were reliable and predictable, is the reason they will be the first to be automated. UC Berkeley has one of the top computer science programs in the world and 23% of recent graduates are unemployed. The linear life is the one that is most at risk.

In a world being rapidly automated, people need to rely on adaptability, creativity and resilience. You need to be thinking on a higher order plane about what builds value for people. You need to be flexible and able to pivot without fear of failure, constantly being curious and agile. You have to be the one who is calling the shots and managing the automation, not being replaced by it.

Think about it this way: AI can easily do anything you can program into a formula or decision tree, or anything that is easily repeatable that can be learned. And it does it 100x faster than a human. If your daily work is made up of routines, then it can likely be automated. A radiologist looking at X-rays or MRIs to detect fractures? Automated. A CPA that fills out your tax forms and filings? Automated. A lawyer that reviews contracts, checks for regulatory compliance, and drafts documents? Automated. In a world of gatherers, you need to be a hunter to survive.

How to Become a Hunter

As the child of conservative Taiwanese immigrants, I spent my early life living linearly. I jumped through all the hoops of Ivy League college, big name consulting firm, top business school, and numerous fancy corporate jobs. My identity was completely tied to my resume and I was terrified of leaving that secure path. I was afraid of my parents disapproval and disappointment. I was anxious about being judged by friends and even strangers. I cared so much about how others viewed me and my success. When I finally decided to leave that path and start my own company, I realized how little all of that mattered. I was so fulfilled by being my own boss and doing what I wanted to do with my life, that I couldn’t care less what strangers thought of me. And if they were friends who weren’t supportive, I didn’t need them in my life.

That was my first taste of agency and making my own choice, not the choice of my parents or society. Since then, I have continued to make choices that have empowered me to live an exponential life. Choosing to create a community of Asian American founders. Choosing to pool angels to invest over $30 million in 100 companies. Choosing to write an open letter condemning Asian hate crimes and publish it in the Wall Street Journal. Choosing to finance a documentary about Jeremy Lin. Choosing to launch a venture capital fund. Choosing to start Hyphen Nation to publish essays and a podcast to inspire others. I didn’t need permission, I had to make choices.

Every one of these decisions led to an experience with compounding returns that created more opportunities and choices. I didn’t escape my linear life, I just learned how to leverage and compound it into an exponential one with my decisions. This isn’t about leaving your life behind. Nothing you’ve lived is wasted. Your life is a book, and every chapter adds to the last one. This is about proactively investing in the life you’ve built in a way that will hopefully yield compounding returns. Was it easy making these choices or was it a smooth journey along the way? Not at all. But looking back, each of these decisions shaped who I am today and I am grateful for making them.

The founder community gave me access to entrepreneurs and investors for my angel syndicate. Together we’ve invested in multiple billion dollar companies like Gamma, Formation Bio, Persona and Super.com among others. The syndicate I grew, allowed me to instantly recruit hundreds of prominent signatures for my open letter which helped raise millions of dollars. Through this group, I also found fellow financiers to help produce 38 at the Garden which resulted in winning my first Emmy Award. This notoriety has led to speaking opportunities, awards, board positions like the Smithsonian Asian Pacific Center and even being featured in museums like the Museum of Chinese in America and the Milken Center for Advancing the American Dream. All of these amazing experiences coupled with my network have inspired my essays and conversations for the podcast, which has motivated me to write a book. Instead of asking myself why I should do something, I’ve started asking myself why not?

My first-hand advice on shifting from a linear to exponential life:

Take small steps to gain confidence. Define success for yourself. Work backwards and figure out what it takes to get there. When you take small steps towards a dream, it can gradually help to build more self-confidence and belief in what is possible. When I started working on a side project and gradually convinced myself that there was a there there. I only needed a little bit of proof that I could earn a living to quit my job and start my first company. Before I started my first venture capital fund, I invested in numerous startups by syndicating SPVs (special purpose vehicles). Once I realized the value I could bring to the table and started seeing returns, I knew I could build a fund. The only way to find out if a dream is worth chasing is to start working on it. That is by far the hardest part. Whether it’s a book or a business, just get started. Once you’ve achieved your goal, you will realize that you can start taking even bigger swings.

Surround and inspire yourself with other people living exponential lives. It’s a lot easier to take risks and think big when you see others doing it regularly. Watching them not only succeed but fail, and realizing the downside isn’t as bad as you projected it to be. Naysayers and passive people will only project their fears and doubts onto you, and you don’t need that kind of pessimistic energy around you.

Say yes to more opportunities that come your way. Take that coffee meeting when someone reaches out. Join that non-profit advisory board. Go to that conference that you’ve been interested in attending. If there’s one thing I’ve learned, opportunities will come your way when you least expect them, but you have to make room for them. Expand your network because it will open up more doors that weren’t available to you before.

Stop worrying about what others think. We underestimate the power and influence others have over our decisions. Many children of immigrants have spent their lives seeking the approval of their parents, because they feel indebted to them for their sacrifice. If you’ve been on a track your whole life, you are also afraid of judgment by your peers who have been on the same track with you. Only when you free yourself from the burden of others expectations, can you truly start living your life.

People can become very successful living a linear life, but they might not find fulfillment, especially if that life path was decided for them by someone else. I know plenty of financially successful lawyers and doctors who hate their jobs. Now even those jobs are at risk of becoming made obsolete in the new era of AI technology. An exponential life is about finding success as defined by you, which means it will be inherently purpose-driven and fulfilling.

So to those who have recently been laid off from their jobs: Don’t despair. Reframe it as a blessing that you are free from the hamster wheel. Now you have a head start to figure out how to become a hunter and start living an exponential life. You don’t need to manufacture audacity from scratch, it should come from knowing that your story is worth telling. I realized that I didn’t need to become someone else to start living the exponential life, I just had to give myself permission to be fully me. Everyone has the power to give themselves that permission. You don’t have to follow a script that wasn’t written for you. This week, take one step by doing something not on the script you’ve been given. It’s up to you to start writing your own script.

If you are never uncomfortable, it means you’re not growing. There is a reason they are called growing pains. Growing means expanding your horizons and doing things that you’re not good at. It means falling, failing and making mistakes that make you feel embarrassed or judged. You can’t get better at anything if you don’t work at it. No one learns to ski without taking some bad wipeouts and tumbles. You can only ski black diamonds after you’ve fallen again and again on the greens. There is no sense of accomplishment when something comes easily. Amazing things can happen on the other side of discomfort.

Too many people suffer from inertia in their careers. They get too comfortable and stop taking risks. Then they wonder why they aren’t getting promoted. They go into cruise control and do things that are easy for them. They blame their managers for not recognizing their contributions, when in reality, they are meeting their job requirements but nothing more. They aren’t pushing themselves by taking on more responsibility to justify a promotion. In reality, these people are afraid of being pushed out of their comfort zones. People remember those who are bold not those who maintain the status quo.

Other individuals are afraid of failure so they refuse to take any risks. Taking on a new role or pivoting careers is scary because it is uncomfortable and unknown territory. We need to learn to show ourselves more self-compassion and grace when things don’t work out the way we hoped or planned. Only then will we be able to continue to embrace being uncomfortable.

Close Your Eyes and Jump

Often the hardest part about uncomfortable situations is the build up of tension. The sooner you break that tension with action, the less stressful it becomes. Once the deed is done, the tension dissipates and relief sets in. When you do this enough times, you begin to realize that the benefits of taking action far outweigh the anxiety that leads up to it. That anxiety is very real and can be paralyzing. It’s like standing at the edge of the bridge before a bungee jump or skydiving jump. It is terrifying right up until the point you jump, and once you do, it’s freeing because you can’t go back. And you are left with the exhilaration and accomplishment of overcoming that fear instead of letting it overcome you.

It doesn’t have to be bungee jumping, even asking the first question in a meeting can be scary for some. The fear of judgment from others can be even more anxiety-inducing than jumping off a bridge or plane. Until you realize that you can’t control what others think of you, and understand that they really don’t think about you as much as they think about themselves, you will never be free of that fear. But once you hear your own voice and others hear it, it becomes a lot easier to do again and again. Like anything else, getting good takes practice and repetition. Ask the first question. Volunteer to take the hard project. Step up to make the presentation at the conference. This is how you get seen, earn respect and ultimately get promoted.

Do What Needs to Be Done

Sometimes doing what needs to be done or saying what needs to be said, can mean having awkward or difficult conversations. This includes firing people at your job who aren’t performing, giving feedback to an administrator at your child’s school or confronting a neighbor who is causing problems. There are many situations in which we tend to avoid, because we are afraid of the discomfort and anxiety that comes with having these tense interactions. But like getting a vaccine or flu shot, it might hurt a little for a brief moment, but it needs to be done for the long term benefit of yourself and for others.

You will never be seen as a good leader at work if you are unable to handle letting go of a problematic employee. By delaying the inevitable, you merely destroy credibility with your other good employees, because they can’t trust you to do the right thing for the greater good. Avoiding your personal temporary discomfort leads to a lot of pain for other people, because you’re unwilling to do what needs to be done. I outline this in my previous essay about learning to embracing conflict.

If you want something, you should ask for it. You want that raise or promotion? Ask for it. You want to be on that project? Ask for it. You want to go on a date with that guy or girl? Ask for it. Yes, it might feel uncomfortable in the moment, but you owe it to yourself to know the answer. The worst that can happen is that you get a “no” but at least you will have an answer and can move on without speculating any longer. Life is too short to linger on the what ifs.

Speak Up for What is Right

It’s okay to speak up when you aren’t sure if others agree with you. There is nothing wrong with saying the unpopular or contrarian thing if you can back it up. If people are wrong, they are wrong, regardless of consensus. Many people agreeing that the wrong thing is right, doesn’t make it any more right. It might be uncomfortable at the time, but as Martin Luther King, Jr. said, “The time is always right to do what is right.” Moral action should not be delayed by convenience, fear, or seeking the “perfect” moment. You should always act with integrity, regardless of external pressures.

During the pandemic, I wrote an essay for a community that I had built over the years. It was not meant to be shared publicly. But a member of the group tweeted it to her 100,000+ followers, and I panicked. I thought I would be judged or make people angry with the essay. I wasn’t ashamed about anything I wrote in the essay, because it was all true. It was the fact that I was saying the quiet things out loud and calling out the discrimination against the Asian American community. I was afraid that there would be blowback, because I rarely saw someone with my resume take any risk by speaking up about the ugly truth. I wasn’t sure if I should take it down for damage control.

Prior to writing this essay, I had been extremely vocal in my condemnation of the murder of George Floyd. I was outspoken for the Black community on public spaces like LinkedIn and Twitter. But all of the sudden, when it was time to speak up for my own community publicly, I was scared. I was uncomfortable because I hadn’t gotten permission or seen anyone else in my position say these things openly before.

Rather than allow my discomfort or fear consume me and take down the essay, I embraced it because I knew it was the right thing to do. And because of that decision, Hyphen Capital was born and it became my life’s work. I have now invested over $35 million in Asian American founders and launched my own venture capital firm. If I had deleted the essay, none of this would have been possible.

Embracing Uncertainty

I speak to far too many people that are miserable at their current jobs, but they refuse to quit without having another job in hand. They would prefer to be miserable with a job they have, than risk not finding another one. Being comfortable with uncertainty means having the self-confidence and mindset that you can bet on yourself. Some people see the unknown as terrifying and scary like staring into a dark abyss. This is a result of a scarcity mindset that makes you live fearfully, always expecting the worst possible outcomes. Others see the unknown as an opportunity like an open field with multiple paths. This is a reflection of a growth mindset, believing in your own agency and ability to forge your own opportunities and success. For some, having the comfort and security of the bird in hand is worth far more than two right in front of them.

I know many who have fully embraced the uncertainty and changed careers. They gave up high-paying jobs that the world would label successful. My friend Abigail Hing Wen was a powerful lawyer working at Intel before becoming a bestselling young adult author and film producer/director. My friend Joyce Tang left her marketing job at Facebook to open a nationally acclaimed pastry business. Simu Liu famously got fired from his accounting job to pursue a successful career in acting. Robert Wang was a laid off software engineer who decided to solve how to make a healthier dinner, so he invented the Instant Pot. There are countless stories like these, of people who took a chance, even though they were unsure of what their future would hold on the other side. And while these are selective stories of success, I’ve spoken to those who have failed to make the pivot, and they have no regrets. You only get one life to live. Few people ever regret pursuing their dreams, but many regret never doing so.

Personality Types

I want to acknowledge that not everyone is wired to take risks. When I was working with an executive coach, I took an Enneagram personality evaluation. My Enneagram is a Type 7 or “The Enthusiast.”

The Enthusiast is characterized by a zest for life, optimism, and a drive for new, exciting experiences, seeking to avoid pain, boredom, and limitation by staying busy and planning future fun. While they are spontaneous, versatile, and good at generating ideas, they can become scattered, undisciplined, and avoid difficult emotions, potentially leading to overcommitment or escapism, but at their best, they are joyful, appreciative, and content.

As a person who is optimistic and drawn to new experiences, it is easier for me to take risks than a Type 6 or "The Skeptic.” A Type 6 prefers safety over uncertainty.

The Skeptic is characterized by a deep need for security, guidance, and support, stemming from a fear of threats in an unpredictable world, leading them to be vigilant, responsible, and loyal, yet prone to anxiety, self-doubt, and seeking reassurance, often becoming excellent troubleshooters by planning for what could go wrong.

I highly recommend speaking with an executive coach to better understand your personality type and how to deal with being uncomfortable. Everyone experiences fear and anxiety differently, and it’s important to know how you can most effectively deal with yours. Nothing is more helpful than self-awareness of how you personally are wired.

The fear we build up in our own minds is almost always scarier than reality. We usually anchor to the worst case scenario which is the least probable one. “I will get fired from my job if I say that.” “I won’t be able to find a job if I am unemployed.” “I won’t be able to earn an income if I change careers.” “Someone will come after me if I speak out or take a stand.” We create a bogeyman in our mind that keeps us from taking risks. But everyone knows that the bigger the risk, the bigger the reward. Because when you have agency and control, you have more earning power. Starting your own business. Building your own brand. Creating and producing your own product or intellectual property. Ownership and equity is the fastest way to freedom and success.

If you were raised in a culture with an immigrant scarcity mindset, then you likely brought up to plan for and expect the worst possible scenario. You choose a career based on security and reliability. You choose the most predictable jobs that will pay the best, lawyer, doctor, engineer or finance/accounting. The problem is that now these jobs are all being replaced by AI, exactly because they are so predictable and programmable. The safest careers are no longer safe. Nothing is guaranteed and it is a myth that anything is a sure thing anymore.

What I do know is a sure thing, is that no one gets ahead without taking chances. And taking chances requires putting yourself into uncomfortable positions. The only people who succeed are the ones who stand apart from the crowd. They are the ones who get noticed because make others take notice. They speak up, they create new products or content, they take on difficult challenges.

I recently hosted a fireside chat with Julie Kim, the CEO-elect of Takeda Pharmaceuticals. She will be the first Korean American and Asian American to lead a multinational big pharma company. She said she wouldn’t have gotten to this position if she hadn’t “led from the front.” She took on managing big business units and P&Ls. She spoke at conferences. She moved around the world solving problems. None of these things were comfortable, but she did all of them. That’s what it takes to make it to the top.

Like Julie, every successful person I know has had to step out of their comfort zones and take chances. They have had to bet on themselves time and time again. But each time, it became easier, because they learned that the odds are better than they had originally assumed. If you continue to fold every hand in life, you will never have a chance at winning. You will just continue sitting on the sidelines waiting to get in the game. Stop waiting, and start making bets.

You probably know the names Oprah Winfrey, Taylor Swift, Kim Kardashian and Sheryl Sandberg, because they are all self-made billionaires. But did you know that a Korean American woman is worth more than all of them?

Thai Lee built IT provider SHI International from next to nothing to generating $15 billion in annual revenue, making her worth $6.1 billion. She is the president and CEO of SHI and owns 60% of the company.

Lee was born in Bangkok and grew up in South Korea. She moved to the U.S. for high school at the age of 15, before attending Amherst for college where she earned a dual degree in biology and economics. She was part of the first class of women allowed to attend Amherst. Her father was a prominent economist who was the first Korean to graduate from Amherst, after working as a translator for the US army in Korea and earning a full scholarship. Thai Lee earned the title of Amherst’s most successful entrepreneur ever in 2016.

After graduating from Amherst, Lee returned to South Korea to work at auto parts manufacturer, Daesung Industrial Co. to save money to pay for graduate school. She also attended Harvard Business School, where she became the first Korean woman to graduate with her MBA. She would work in Brand Management at Procter & Gamble for two years and then in the corporate card division at American Express after business school.

In 1989, she and her ex-husband purchased a software reseller called Software House for less than $1 million which later became SHI. The company focuses on designing cloud, data center and end-user computing strategies. It has over 15,000 customers including Boeing and AT&T and is ranked among North America’s top 15 largest providers of IT solutions. SHI recently invested $20 million in a newly launched AI lab where it tests out AI solutions for customers using NVIDIA’s technology. SHI is recognized as the largest minority and woman-owned business enterprise in the United States.

At the 2019 Women in Cloud Summit, she told aspiring female entrepreneurs: “It’s OK to fail. At least you would have tried and have done your best.”

Lee is a devout Buddhist and credits Buddhist teachings for helping her maintain perspective. "The foundational belief in Buddhism is that life is unavoidably about suffering. So, learning to adjust my expectation was really a huge advantage for me, combined with hard work and learning that education really allows one to achieve mobility.”

She established the Thai Lee Foundation after meeting an inspirational young girl who was hit by Syrian government shrapnel and paralyzed. The Foundation has helped humanitarian projects from building orphanages and libraries in Turkey as well as psychosocial support centers and schools in Syria, According to the website, the foundation has benefited 3.5 million individuals and organizations with $485M in previous and current financial contributions.

She sits on the Board of Trustees of Memorial Sloane Kettering Cancer Center.

Time Magazine recently named MyFitnessPal as one of America’s Top 25 Most Iconic Companies.

Mike and Albert Lee were Korean American brothers who grew up in upstate New York in Schenectady where there were few Asian families. Their father was a metallurgist who worked at General Electric. Their mother went back to school to get a computer science degree at SUNY Albany when Mike was in middle school. He audited to her classes for fun and help her with her homework. He played baseball and volleyball in high school and went to Princeton where he could continue playing volleyball. Albert would go on to UC Berkeley. Both of them graduated with degrees in economics.

Mike would start his career in consulting at Mercer Management Consulting. Instead of applying to business school, he decided to work at the NIH for a year to do medical research. He applied to medical school and was accepted to UCLA. But after speaking to doctors who deterred him, he realized he wasn’t that passionate about it and turned them down. This was during the time of the tech boom in Silicon Valley, and decided to move from DC to San Francisco without a job and slept in a friend’s closet for six months. He finally found a job in marketing consulting for tech companies before joining a startup called Software.net which became Beyond.com (the Amazon for software). Mike would eventually join Handspring to run the e-commerce team before it was acquired by Palm.

After leaving Palm, Mike started working on a free dating site with a friend. On the side he was trying to lose weight for his wedding and was told to count calories. He didn’t want to use pen and paper, so he looked for an app or website, but they were all terrible, so he decided to build it himself. He got back into coding and MyFitnessPal was born.

Albert began his career in finance as an analyst at GE Capital before joining Yahoo in 1999. I was a product manager at Yahoo! for Yahoo! Finance and Albert was one of my fellow product managers, working on Yahoo! Shopping. Eventually we both went to business school at Stanford and Berkeley, before ending up at eBay after we got our MBAs. Albert would eventually leave eBay and return to Yahoo and work at some startups. Mike had been managing MyFitnessPal by himself and the website traffic continued to grow to the point where it exceeded the dating site, so he quit to work on it full-time. He called Albert and pulled the big brother card, telling him to quit his job and help him work on MyFitnessPal.

Mike and Al bootstrapped MyFitnessPal for eight years and never raised outside capital. They stayed lean and did everything themselves for the longest time. They had four employees when they had 30 million users visiting the website. When they launched their mobile app, they became a top fifty app in the entire app store.

VCs were literally knocking on their office door trying to give them money. They were afraid of taking outside money, because they didn’t want to have a boss again. Mike and Al hadn’t taken a salary for three years, but now the company was very profitable, so they finally paid themselves. They didn’t need the money, so they didn’t want to take on any investors.

As they talked to investors, they realized that there was value in having some of these investors help them. With the right firms, it would be more like having a partnership than having a boss. They also had heard that a lot of the big tech gorillas like Google and Apple were moving into the health space, so raising some capital would give them ammunition to defend their position.

In 2013, they decided to raise $18 million in venture capital in a a Series A from Andrew Braccia at Accel and John Doerr at Kleiner Perkins along with a $20 million secondary to take care of their families. It would be their only institutional funding round. Andrew and John were pivotal in making introductions and open doors.

MyFitnessPal had grown to the largest nutrition database in the world with more than 5 million foods. In its nine years of existence the firm has amassed more than 80 million registered users for its website and app.

In 2015, the Lee brothers agreed to be acquired by Under Armour for $475 million. They felt like it was a good cultural fit, because they had a very entrepreneurial culture driven by their founder, Kevin Plank. Mike became the only Asian on the executive team. He only cared about doing what was best for the company, and because he wasn’t trying to be political, he was promoted.

The best part of building MyFitnessPal for Mike and Al was hearing the personal stories and testimonies from their grateful users. Their product was literally changing and saving lives.

We have reduced our values to metrics, but how much of what actually makes our life valuable is easy to count?

On the latest podcast episode of Pablo Torre Finds Out, talks to the author of The Score: How to Stop Playing Someone Else’s Game, written by philosophy professor C. Thi Nguyen. He talks about how we now live in a society where everything is gamified and measured in metrics. Michelin stars, Netflix ratings, likes and followers and more.

I am old enough to remember the time before the U.S. News and World Report College Rankings existed. Back then, there were books with profiles of every college describing their values, campus life, and programs strengths and weaknesses. It required you to choose based on which school was the right fit for you. The rankings came along and simplified that choice by giving every school a numerical value with an arbitrary formula. And people just wanted to go to a school based on the rankings, rather than ask the hard questions.

As children of immigrants, many of us are forced to play the same game from a very early age: Get good grades so you can get into a good college so you can get into medical or law school and make lots of money as a doctor or lawyer. Eventually computer science engineering joined that elite group. Secure careers that were lucrative and stable. Although with AI, the game has changed and all three of those fields are a lot less stable now.

I played that game for most of my life until my 40s. Wanting to win the game by getting into the right college, the right business school, the right consulting firm, the right corporate job, raise money from the right venture capital firm, all because I was programmed to believe that at the end was a pot of gold that would ultimately bring happiness and satisfaction.

Since I stopped playing that game, I started identifying my superpowers and working on the things I care about. I have been far more successful and more fulfilled every single day because of it.

An undergraduate sent Nguyen an email that said his talk pulled her out of a five year depressive cycle. She was also an Asian immigrant kid like him, pushed to get a 4.0 GPA, a varsity athlete who suffered from anorexia.

She realized that her life had been trapped in bad games. She didn't know that she had any choice. She had taken the games that life had shoved at her and they were making her suffer. She said that something about this framing allowed her to believe that she had some choice about what she was doing and how she was going to be measured. She changed the background of her iPhone to remind her everyday of this: "Is this the game you really want to play?"

Ask yourself, are you playing the game you really want to be playing? Or was this game forced on you? Remind yourself that you always have agency and can stop playing the game any time if you want to.

Last month, Gamma announced that it had raised $68 million from Andreessen Horowitz at a $2.1 billion valuation.

In 2023, I was fortunate enough to meet Gamma CEO Grant Lee through my network and he had been following my work. Hyphen Capital ended up investing in their seed round and I obviously couldn’t be more thrilled for our LPs and for the Gamma team.

This is only the beginning for the company. Raising a round means nothing, it is just another mark on the road to liquidity. Grant and his hard working team of 52 employees and growing are generating over $100 million in annual revenue with over 70 million users. They efficiently accomplished all of this after raising only $22 million through their Series A and have been profitable for a while now.

Grant is a special founder, because he builds authentically and transparently. He regularly shares his personal learnings on LinkedIn, where his audience of 80,000 followers are. Many of whom are the target audience of Gamma and highly likely to create presentations. Grant creates value by providing insights on product, marketing, sales, fundraising and countless other business topics. These are also topics that people need to generate presentations about all the time.

Getting to Yes

I didn’t know Grant before I invested in Gamma. A trusted mutual friend who was his first investor, knew that I was supporting Asian American founders, so he introduced us when Grant was raising a seed round led by Accel. They were classmates at Stanford together and have known each other for years.

Lesson #1: Your network is your access.

If you can meet a founder through a trusted referral who speaks highly of your character and integrity, you will increase your probability of investing infinitely. Friends and existing investors are strong filters for other new investors joining the inner circle. The broader your network, the more likely you are to have a connection with a founder you want to reach. But having a wide and shallow net doesn’t mean you will catch anything. The quality and depth of that net makes a big difference.

Lesson #2: Founders want to work with people they know and trust.

Founders don’t want a wildcard in the mix, because starting a company is hard enough without having additional unnecessary drama or unpredictability on the cap table. A founder is more likely to trust you through a very warm referral than a cold outreach or lukewarm introduction. If you don’t have a warm referral and manage to connect with the founder via cold outreach, build trust in that first meeting. That means demonstrating that you will add value with your insights and questions, providing strong references from other respected founders, and simply finding commonality with each other. Sell yourself and your expertise or how you can open doors for them.

Lesson #3: Your reputation precedes you.

People often form an opinion about you before they even meet you. They do Google or LinkedIn searches and do their research. They will also backchannel you through their network to make sure there aren’t skeletons hiding in any closets. Ideally you’ve invested in companies they know of or better yet, know the founders of. Your reputation is what people say about you when you’re not in the room, and founders talk to each other and other investors.

Luckily for me, Grant had been following my advocacy work and investment in the Asian American community well before meeting me. He resonated with the Hyphen Capital mission and we clicked immediately. He saw value in my network and it helped that I was also a fellow startup founder.

Investing with a Mission

When I started Hyphen Capital, my mission was to change the false narrative that Asian Americans are not good leaders. I wanted to shatter the bamboo ceiling with story after story of successful founders who proved the naysayers wrong. I pulled together a community of investors from founders to executives to law partners to surgeons and even an NBA assistant coach, to support these founders. Our powerful network includes the founders of Old Navy, YouTube, MyFitnessPal, Gusto, Credit Karma, StitchFix, Peloton, Honey, Webflow, Patreon, Rotten Tomatoes and more. It includes the CEOs of Calm and OpenTable, CFOs of Visa, LinkedIn, Masterclass and so many others.

Together, we’ve invested in several successful companies: Safebase was acquired by Drata for $250 million. Pry Financials sold to Brex for $90 million. Revela sold to Oddity for $76 million. Formation Bio raised at a $1.7 billion valuation. Persona raised at a $2 billion valuation. In total, we’ve invested over $30 million in 100+ companies founded by Asian Americans, half of whom have female founders. Here are just a few of my favorite consumer investment stories:

The Gaming Console

An iPhone app propped up on a chair turned into the #1 selling product in Toys & Games on Amazon.

Four years ago, I invested in three co-founders from Hong Kong named David Lee, Tony Sung and Reggie Chan. My friend Alex Wu was part of my founder community Asian American Founders Circle and he ran partnerships and business development for them. Their company Nex was building a basketball AR skills app called Homecourt, which my nephews and their friends used and loved. My son tried it and he was also hooked. We found ourselves propping up my phone on a chair while he dribbled and watched the screen light up with points and sparks. It made practicing more fun.

They created another mobile app called Active Arcade and added new fun augmented reality games. Eventually they saw an opportunity to build a new gaming platform device that they would call Playground. It was a huge risk to bet the company on a hardware device, when software margins were so much better. But the team had conviction and rolled the dice, and it has paid off big time.

Now this little engine that could is sitting right next the Nintendo Switch, Sony Playstation and Microsoft XBox at Target, Walmart and Best Buy. Playground now has titles and partnerships with the NHL, Barbie, Bluey, How to Train Your Dragon, Kung Fu Panda, Care Bears, Sesame Street, Gabby’s Dollhouse, Teenage Mutant Ninja Turtles and more. The Wall Street Journal called it the “Hottest Toy of the Year.” It’s gotten rave reviews from The New York Times, USA Today, Parents Magazine, and Polygon.

It quickly became the top selling product in Amazon’s Toys & Games category, and will sell over half a million units this holiday season. Our family loves our Playground and we’ve played with it every week since we’ve gotten it, because instead of the kids staring at a screen, the games are up and moving with the interactive games.

All from a team that started with a basketball app, who believed in their tech and had the conviction and confidence to bet on themselves. They refused to play small and be put in a box. Instead they will be selling millions of little cubes into households around the world. They are practically sold out everywhere, but hopefully you can get your hands on one before Christmas!

The Soup Dumpling

Restaurant quality frozen soup dumplings steamed to perfection in 11 minutes.

I was first introduced to Caleb Wang via the founder of Italic, Jeremy Cai. Caleb and his wife Jennifer Liao had been following my AAPI advocacy work during the pandemic as well. Caleb and Jennifer are the founders of MìLà, a Chinese frozen food company that started with soup dumplings as their first product. They sent me some samples and I was hooked. As an avid regular of Din Tai Fung restaurants in Taiwan, the fact that I could have xiao long baos at home, any time, in 11 minutes, seemed like black magic to me.

I was shocked to learn that most if not all of the major frozen Chinese food brands in America are actually owned by non-Chinese companies like Ajinomoto who owns Ling Ling dumplings, CJ Foods who owns Annie Chun’s, and Conagra who owns PF Chang’s frozen foods. There’s an estimated 40,000 Chinese restaurants in America and Martin Yan has filmed over 3,500 episodes of Yan Can Cook for PBS, and yet none of the major frozen food brands here are owned by Chinese Americans.

Caleb and Jennifer wanted to create an authentic brand of Chinese cuisine, by Chinese American entrepreneurs. I wanted to support their dream, while also helping to spread quality Chinese food to parts of the country that do not have access to it. This was an investment in not just a company, but a mission.

When we invested, they were a predominantly direct-to-consumer business with some distribution in specialty retailers. Now they can be found at Targets, Walmarts, Whole Foods, Krogers and Costcos nationwide in over 7,000 retail locations. They’ve even partnered with Marvel Superhero Simu Liu as their Chief Content Officer to promote their products. MìLà will continue expanding their products from dumplings and noodles in the future.

The Sparkling Water

La Croix but with Asian-inspired flavors.

I had first heard about Sanzo sparkling water with real Asian fruit flavors like calamansi, lychee, yuzu and mango through my good friend Andrew Chau, co-founder of Boba Guys. He connected me with Sanzo founder Sandro Roco and I loved his vision for bringing Asian-inspired sparkling water to mainstream grocery aisles. Most people had never heard of calamansi before, a citrus fruit native to the Philippines, but Sandro was changing that.

Sandro understands the importance and power of representation which is why he wanted to bring these drinks to shelves of grocery stores around the country. He even partnered with Disney to put Turning Red, Raya and the Last Dragon and Shang-Chi on Sanzo cans when they premiered. We also worked together to do a limited edition Asian Pear flavor with Jeremy Lin on the cans for when 38 at the Garden premiered on HBO Max.

These cans are sitting on my desk right now as I type this:

Sanzo can now be found in Whole Foods, Panda Express, Sprouts, Target and other retailers all across the country. Sandro is introducing people from South Carolina to Indiana and from New Mexico to Ohio, to new Asian flavors that they have never experienced before.

One of their newest investors is model and mega-influencer Chrissy Teigen who currently has over 40 million followers on Instagram.

The Petite Clothier

Stitch Fix for petite women

5’1” CEO of Short Story, Isabella Sun, cold e-mailed me after hearing my name several times talking to other Y Combinator founders and reading my post about building your own house. I also happened to work at Yahoo with one of her investors and advisors, Tim Brady. Isabella founded Short Story because as a petite Asian American woman, she was frustrated with the limited clothing options for her build. She wanted to solve the fit problem for herself, and the 33 million other petite women in America.

Since we invested, Short Story has gone from selling $1 million in petite clothing to tens of millions of dollars of inventory, including private labeled pieces. They have cornered the market in petite women’s fashion by meeting the demand of a large niche of customers.

Short Story has been the USA Today Reader’s Choice #1 Clothing Subscription Box for five years in a row. They have glowing reviews from Business Insider, Refinery 29 and Buzzfeed.

Asian women are the least likely demographic to be promoted in Corporate America, because the narrative is that they “lack leadership potential” or “have no presence”. Meanwhile, women like Isabella, Vicky Tsai, Ju Rhyu and countless others are successfully building massive businesses and debunking the false narrative with their highly effective leadership.

I have story after story of investing in underdog founders like David and the Nex team, Caleb and Jennifer, Sandro and Isabella. Over the years, I have invested time in building a community and network of seasoned founders and executives who can add tremendous value to every single company we’ve invested in. I have also curated extensive relationships with investors who can help support the growth of these companies.

Investing in early stage companies is not a numbers business, it’s a people business. You can identify all of the best founders in the world with your models, but if you can’t get on their cap table, it doesn’t matter. The founders have to choose to take money from you. Your reputation, your network and your insights are all critical in differentiating yourself from anyone else who can write a check.

I’ve poured my heart and soul into making Hyphen Capital stand for something. An investment from us is more than access to capital; it’s access to a pool of domain expertise, potential customers and partners, a community of fellow founders and future investors. Ultimately, these all are part of the story you tell to convince founders to take your money. You are responsible for crafting the story you want to tell as an investor to set yourself apart.

What is your story?

Caroline breaks down the biggest myths (like “you must be a CEO to qualify”), and explains how her first board opportunity came not from a recruiter, but from building visibility outside her day job—speaking on panels, getting known for a clear point of view, and making her expertise legible to decision-makers.

You’ll learn what boards really focus on—CEO succession, strategy, capital allocation, and risk—how board seats are commonly filled (often not through search firms), and why serving on a board is a long-term commitment where fit and governance dynamics matter as much as credentials. Caroline also shares hard-earned lessons from navigating activist shareholders, founder-controlled environments, and the fine line between giving oversight and getting too operational.

If you’ve ever wondered how to position yourself for board service—especially as a woman, person of color, or “non-traditional” candidate—this conversation is a practical, behind-the-scenes playbook on how the game is played and how to start playing it.

Born in Chongqing and raised in Toronto, Domee grew up as the child of two academics — a mother with a PhD in education and a father trained in fine arts — a combination that shaped both her discipline and her creative voice. From drawing alongside her dad in life-drawing classes as a teenager, to uploading art on DeviantArt and Tumblr, to ultimately earning a coveted Pixar story internship after an initial rejection, Domee’s path is a masterclass in resilience, craft, and self-motivation.

In our conversation, she takes us behind the curtain of Pixar’s legendary story process — from pitching boards with sound effects and temp music to collaborating with icons like Pete Docter and Ronnie Del Carmen. She shares how Bao started as a personal side project, why she nearly sabotaged her own pitch by softening its “too weird” ending, and how an unexpected nudge from Pete helped preserve one of Pixar’s most memorable, emotional story twists.

We also talk about the deeply personal roots of Turning Red — her Toronto upbringing, the overachieving Asian kid experience, the aunties, fandom obsession, and that uniquely Asian tension between love, control, and vulnerability. And Domee opens up about learning to harness her own emotions — something we’re often taught to bury — as the key to becoming a better storyteller and filmmaker.

From the surreal chaos of winning an Academy Award handed to her by Awkwafina to navigating the heartbreak and silver linings of seeing Turning Red shift from theatrical release to Disney+ during the pandemic to her reflections on being Pixar’s first solo female feature director and the importance of not being the only — Domee’s story is inspiring, hilarious, honest, and filled with wisdom for any creative, builder, or leader.

If you love storytelling, animation, creativity, Asian American identity, or just want to learn from one of the most powerful voices in filmmaking today, you’re going to love this episode.

Growing up in a largely white Texas town, Vicky endured open hostility, slurs, and isolation—sometimes even from teachers. Later, on Wall Street and in corporate America, she faced the kind of harassment, bias, and power imbalances that many women experience but rarely speak about. Yet through every chapter, she found a way to survive, adapt, and keep moving forward. As she puts it, so many of us—especially in the Asian American community—are raised to chi ku, to swallow pain, to endure, to stay small. But Vicky’s story shows what happens when you stop shrinking and start reclaiming your narrative.

Before creating one of the most beloved skincare brands in the world, Vicky was navigating careers in finance, corporate marketing, global strategy, and even acute dermatitis brought on by stress and harsh products—an affliction that ultimately pushed her to rethink beauty itself. Her path to Tatcha is filled with moments that are heartbreaking, eye-opening, and deeply human. But it’s also filled with bold choices, unexpected mentors, and the incredible perseverance that would one day lead her to build a global company rooted in healing, wellbeing, and Japanese skincare traditions.

This conversation goes far beyond entrepreneurship. It’s about trauma, identity, self-worth, and the lifelong work of reclaiming power. It’s about the invisible burdens many Asian Americans carry—and what it looks like to finally set them down. And it’s about how one woman transformed surviving into thriving, and turned her deepest wounds into the foundation of a brand that has touched millions.

Vicky is one of the bravest, most openhearted leaders I know, and I’m grateful she courageously chose to share her story here.

“The downside of speaking up is usually not as big as anyone imagines. Whether it’s asking for what you want or putting it out there that this is your ambition or “this is a new idea that I’m bouncing around”.

Oftentimes, we almost self-censor because of that downside risk, when that downside risk is actually very, very low. And so getting into that mindset is definitely a shift.”

In this episode of Hyphen Nation, Dave sits down with Faye Iosotaluno, former CEO of Tinder and one of the very few Asian American women to lead a major global tech company. Born and raised in West Covina, California to Indonesian-born, ethnically Chinese immigrant parents, Faye grew up speaking Mandarin at home, navigating multicultural environments, and learning early what it meant to balance assimilation with pride in her identity.

Faye shares how her curiosity and love of learning shaped a career that has been anything but linear. After studying both finance at Wharton and English literature at Penn—an education she credits for sharpening both her analytical and storytelling abilities—she began her career in media investment banking at Merrill Lynch before moving into corporate strategy roles at Viacom and other major media companies.

Driven by a desire to build digital-first consumer products, Faye made the unconventional jump to SoundCloud, embracing a startup environment where she could learn new industries, work globally, and help shape the future of music streaming. That leap eventually led her to Match Group, where she rose through the ranks and ultimately became CEO of Tinder, helping transform a product used by millions worldwide. As she explains, her leadership was grounded not just in operational expertise but in bringing more women’s voices into product design—because a dating platform can only thrive when it meaningfully serves women.

Faye opens up about navigating male-dominated tech environments, the importance of storytelling as a leadership tool, finding allies in the room, and learning to speak up—even when it’s uncomfortable. She shares how she eventually put her ambitions on the table, telling her manager she wanted to be considered for CEO, a pivotal moment that taught her the power of naming your goals out loud.

As one of the very few Asian American women to ever serve as CEO of a major tech company, Faye also reflects on the responsibility and privilege of being visible representation. After stepping down recently, she discusses the emotional complexity of leaving such a role—and the profound notes she received from people inspired by seeing someone who looked like them leading at the highest levels.

This conversation dives deep into identity, ambition, leadership, risk-taking, and the mindset shifts required to grow into your full potential. Faye’s path is a masterclass in how to build an unconventional career, claim space in the rooms that shape culture, and lead with both substance and humanity.