Never Trust Dating Advice From A Guru In Another Field

For those who aren’t aware, Gary Vaynerchuk is a famous social media business guru. He has millions of followers across many platforms, so many creators turn to him for advice and he’s really established himself as the expert in the space for entrepreneurship and social media marketing. Yet I recently thought about something he said in one of his older books that turned out to be not true.

He was addressing a question about dating advice and how he met his wife and he said that “when you know, you just know.” He met his wife and got married within a short period of time.

Well, it turns out he was wrong. Years later, he got divorced. And the new woman he is wife is more attractive, which isn’t that big a surprise since his fame, status, and wealth shot up since his last time in the dating world.

Now, I love Gary, and he gives a lot of great business advice. But it’s just one of many examples I’ve noticed recently of when a guru starts to step out of his niche and give advice on everything. And then, his fans assume he’s great at everything since he’s rich and famous, so they take his advice. This behavior is dangerous, especially since any bad advice that was proven wrong is often swept under the rug, forgotten, and not highlighted.

People see the status and the level of flashy things they have and a sinister influence starts happening. Their content and advice start bleeding over to areas of expertise where they’re not so great at even if they think they are. Surely, they must be a master of dating and have all the answers there too, right?

I love Alex and Leila Hormozi as they seem to be legit entrepreneurs at the top of their game, but I can’t help feeling the same danger. And yet I can’t help but to eat up a lot of their new relationship and dating advice videos. They tend to stay away from that, but lately, they’ve been posting more about that.

Frankly, their success in dating has yet to be played out. They’re both young, without a single gray hair, and whether their relationship will be a success is still to be decided. They could be divorced in ten years. I personally think they’ll still be together but who knows? So, to give a lot of advice on what keeps a relationship together is dangerous, especially since they live a unique life with unique values where they believe it’s okay to not see your partner much for months if they’re in a season where they’re focused on their business.

I’d rather listen to advice from someone who is already near the end of their life with a proven a track record of 50+ years of marriage and a successful business. We have thousands of years of history. Surely, there must be a couple like that that we can turn to, not just the latest, newest flashy people in the spotlight of social media? I’m sure they’re out there, but my knowledge is limited. The only couple I can think of off the top of my head similar to that is Jack Welch and his wife, although even Jack got divorced. You may have better luck looking for one through a nonprofit business mentor organization like, which matches you with successful entrepreneurs volunteering their time. If anyone has any ideas on who to follow, leave a comment.

Another recent example of gurus straying from their niche to give dating advice or discussion on the topic is Humphrey Yang, a new but very popular personal finance TikToker and YouTuber with 1+ million subscribers. To be fair, he probably didn’t want to make this video but his audience begged him to talk about his dating life and were nosy.

Nonetheless, I could tell he doesn’t really know what he’s doing in dating. It’s not my first time encountering someone who is rich but struggle in dating. I see it all the time. For example, I recently found out Robert Kiyosaki, author of Rich Dad Poor Dad a popular book on getting rich, got divorced. I’ve seen clips where he talks about it and how he’s learning about common dating principles and terms now. He’s clearly a beginner with it all. And you realize while he has some “alpha” traits from being wealthy, there’s a lot of low-value or “beta” behavior he shows and a lack of understanding or knowledge about basic dating principles. (As a side note, just like in the book Mate by Tucker Max, I don’t believe in the alpha/beta male dichotonomy because it’s too simplistic for complex human societies, but I’m using it here because it’s easy for readers to understand and gives you a general idea of my point.) He admits he stopped trying in his marriage and got very overweight.

So what does Humphrey say in his latest video?

Here are his main points about why he’s still single:

– **Reasons for Being Single:**
– Last real relationship was 7 years ago. That’s not really a reason but more of a fact.
– Dated multiple women for short periods since then.
– Prioritized career over dating, especially since age 28. He only made $50k a year at the time, which is not much in the Bay area.
– Viewed success and wealth as a prerequisite for serious dating since he believed women wanted someone rich to take care of them. (This is a false limiting belief. I discuss why Humphrey is wrong about this later.)

– **Career Prioritization:**
– Now, he’s fairly wealthy. He’s still staying focused somewhat on career. But then, he contradicts himself and admits he has plenty of time for dating.
– Acknowledges the challenge of balancing career and dating.
– He realizes wealth isn’t everything. Now, he’s saying it may not even matter (I think it does to a bit to not the extreme he’s claiming) and there are traits anyone can work on before they’re wealthy. Women care more about confidence, ambition, and your potential. He doesn’t think he’s confident.

– **Perception of Success:**
– Believed financial success was crucial for serious dating.
– Influenced by societal views, especially from online content.
– Found it hard to date seriously in the Bay area without a significant income.

– **Challenges in Modern Dating:**
– Meeting people has become more challenging. Everyone defaults to dating apps.
– Online dating is the default method, impacting in-person interactions.
– Fear of rejection and potential negative labels of being creepy prevent him from in-person approaches even though he thinks it could be better than apps.

– **Paradox of Choice:**
– Overwhelmed by the abundance of choices in online dating. Or at least the “perception” that you have a lot of choices.
– Leads to the emergence of “situationships” and commitment issues since everyone thinks they could find someone better.

– **Societal Norms and Dating Advice:**
– Dating advice suggests diversifying options before exclusivity.
– Struggles with dating multiple people simultaneously due to a desire for commitment.

– **Money and Dating:**
– Acknowledges having money is beneficial but not everything.
– Now, he emphasizes traits like support, confidence, and shared values as crucial after realizing the problems of just dating the most attractive woman without any other criteria. (I’m thinking no, duh. You just realized that? But I get it. I’ve been there. Many people I know still fall into this trap. They rate women purely on looks from a 1 to 10 scale. At least for long-term dating, this is a short-sighted, overly simplistic approach.)

– **Social Media Presence:**
– Admits that a social media following can be advantageous to building trust and meeting people.
– Stresses that a substantial following doesn’t matter at all and they’re not better than you or have their life together because of a following.
– Social media is making it difficult now more than ever. You’re bombarded with people flexing on social media and have to compete with those images of people better than you. Or at least it seems like you’re comparing a lot more. In the past, you were limited to your geographic pool when there was no internet.

– **Self-Reflection and Growth:**
– He thinks personal growth and understanding oneself contribute to confidence.
– He is learning to prioritize traits like kindness, consideration, and integrity in a partner over looks.

– **Conclusion:**
– He’s single in the last 7 years because he didn’t know what he was looking for, focused on his career, and lacked self-confidence.
– Optimistic about finding the right partner with newfound awareness. He thinks if you stay passionate and work on yourself, the right person will come along when you least expect it.
– Believes having a good partner is crucial for making better life decisions.

While I love Humphrey’s personal finance advice, I think a good portion of his points are malarkey. Good-intentioned bad advice can lead you astray. I really recommend we stay away from dating advice from other men who are also struggling. That’s a recipe for disaster. Sure, he’s learning the truth slowly from his mistakes, but it’s still like following someone who is feeling around in the dark.

Yet there’s a lot more of this content these days. I’m often hit up with ads, DMs, or content from dating advice coaches or just people spouting their dating opinions, and some of them aren’t that impressive when it comes to their credentials, testimonials, or their partner. While I do invest in some, it’s important to be selective.

And I’m not surprised to find that Humphrey has a lot of basic, beginner, stereotypical limiting beliefs about dating even though he’s successful with social media, wealth and his career now. Because I’ve seen it happen all the time. Those are two different skill sets. In rare instances, men know how to use their wealth and status to level themselves up in other social areas properly.

So, what’s off about Humphrey’s points?

First, he acknowledges that he was operating under a failed belief system until recently. He thought getting rich would solve all his problems, and it didn’t. That’s not a good sign. He’s admitting his beliefs up until recently are off. So who is to say his new beliefs are on point? I’ve encountered a lot of rich people online, in-person, and through stories that can’t get a date with a quality woman to save their lives. I’ve known for years now that money alone won’t solve your dating woes if your social skills and various other dating attributes (physique, style, humor, mental health, etc.) are low stats.

Yet it’s disappointing that I often still encounter people who believe that wealth will solve everything even if they suck at everything else. I used to believe that too partially when I was young; it’s a common Asian American immigrant cultural programming. But I see it in many ethnicities. They think once you’re rich, you can have status, nice flashy things, and that will attract everything you want. But then, they discover they’re rich but still single.

There’s variations of this flawed belief in other single-trait stats as well. For example, a long-time bodybuilder YouTuber I followed called Healthy Gamer made a whole video years ago about how he thought getting jacked would solve all his dating problems, and it didn’t.

But when you think about it and look around, you’ll find (or you may already know) plenty of rich men who have no personality, charisma, or game. They may be completely out of shape, have no social skills or street smarts, have poor grooming, or another off-putting trait that their money can’t make up for. Or they have no system or idea for how to meet women effectively. Think of all the off-putting socially-inept men in Silicon Valley and Seattle that make six or seven figures.

I’m not saying wealth doesn’t matter. It certainly helps, and studies prove that. I’m saying that a lot of money alone won’t solve everything, as Humphrey and others discover, especially if you don’t know how to invest that money properly in bettering yourself.

As mentioned earlier, he contradicts himself a couple times. He says money doesn’t matter at all at one point, mentioning other attractive traits like ambition and confidence that he could’ve started working on earlier. Even though he mentions that, he also says money is really important, and he felt he couldn’t date or have much to offer until he was rich.

Then, he also says he had no time since he was focused on career and still is, but then, he admits he has time for dating if he wanted to now.

I’ve mentioned this other common fallacy numerous times in my writing, but I’ll say it again. You don’t want to use your career as a crutch or excuse for why you’re floundering in other areas of your life. Because sometimes, it’s a lie you tell yourself to justify your failure when you know you have the time, and you’re just avoiding it or justifying working more to cover up. Some people are too scared to face this truth, but at least for me, I really care about improving the other areas of my life. That motivates me a lot, so I’d rather face the truth than avoid it. Humphrey isn’t as extreme an example of this; I truly believe he actually did care about making his career his #1 and it took up all his time. There’s a season of life for that if you want to level up. The issue is he’s passed that season, and you can run some quick numbers on Social Blade to tell he’s making a lot of money now and has the time.

I disagree with the idea that you have to put off dating until you’ve “made it.” That leads to these 30 to 40 year old men men who have had little to no social skills, experience, or game because they’ve neglected that part of their life for so long under this delusion. Ever pause to realize that the hottest women in your local community that you would want to date are often dating men who are well-off but certainly not the richest? I can think of three women immediately I’ve encountered who are dating men who are certainly not rich. They’re local athletes – one owns a local gym and does some extreme long-distance ice skate racing. And another loves soccer. The third is great at hockey – once again, not at a national level, just locally – but he is someone who loves the same sport as his partner. Nothing about their Instagrams yell that they’re mega rich yacht owners. My point is that money and status helps but when I look at local people who are actually successful, they’re not millionaires. They’re doing well enough and have many other athletic and social traits that matter more.

The ones who neglect their body and fitness fall way behind on stats that matter, to use a video game analogy. Similarly, they’re also likely the type to have neglected team sports and socializing in favor of academics growing up, which makes it very difficult to catch up on those stats even if they have money. The belief that you can’t find someone worth dating until you’re rich or high-status is false and self-selects out people from the dating market. You’re just shooting yourself in the foot by adopting a mindset of “just don’t even try. give up.” Frankly, I’m not even sure I want to inspire these people get out of their funk. When I’m running a race, there’s enough people who are savage competitors and trainers, why worry about or help the people with limiting beliefs that convince themselves to not even enter?

I’ll give you one more piece of evidence and then, I’m moving on. Recently, I’ve had conversations with a barber and various Uber drivers. And guess what? They all have girlfriends or wives. These are not high-paying, high-status jobs. Yet they were able to match with someone. You ever stop to consider that many people in various walks of life and salaries are all still pairing off? Doesn’t that run contrary to this belief that you can’t ever meet anyone until you’re uber rich? And frankly, most people never get that rich despite trying.

You may argue it’s good to go away and set aside time to level up to attract a higher quality mate. But that’s a different topic than what’s mentioned. If you want to do that, that’s great. Go ahead and focus on building your career or income, working out, or other areas of self-improvement. The topic at hand is something different, which is believing you cannot date or find someone at all until you’re rich. It’s sad because this is one example of many losing mindsets that just filter out and self-select out competition who want to shoot themselves in the foot and condition themselves on how to flounder in the dating market.

A lot of his other points speak to the same theme of having stereotypical ineffective beliefs about dating that shoot yourself in the foot. I know men who want to meet someone naturally so they avoid apps and they’re still single and without any dates and well into their 30s. And Humphrey here is doing something by avoiding approaching people in person because he’s scared of rejection or being a creep or getting canceled. He’s bought into this idea that it’s impossible to approach without coming off creepy, which is just wrong. Likely, it’s more fear of rejection than anything else. But yes, women can be mean. I’ve encountered vicious rejections, and they do get approached often. But he’s literally cutting out a large portion of his ability to meet women and just hiding behind digital apps by doing this.

Well, news flash. I’m firing on all cylinders. I approach in person and on apps. And guess what? It’s not easy. You will have unpleasant interactions, but you will have pleasant ones as well. You may run into jaded women who jump to conclusions that you’re creepy or rude just because they’re scarred. All you can do is be as respectful and non-creepy as you can. And sometimes, you’ll fail at that at first if you’re a beginner because you have terrible mannerisms you have to iron out. But not even trying is just going to leave you at the starting line.

I had to invest in high-quality photographers with some of the best dating photographers in the world. I have to tweak and analyze what I did wrong when I get rejections from women in person rather than get butt hurt. I have to push past feeling bad and learning from my mistakes. It took a long time to start doing that because it’s easy to get upset. But I did it. If you’re not even putting yourself in the game, you’re in for a rude awakening when you realize the game is hard and competitive when you’re in it and others are willing to work to practice and improve within the game.

I don’t think “cold approaching”  strangers is the only way to meet people. That’s a pick up artist thing, and they’ve introduced some helpful and some bad ideas. There’s plenty of more warm social interactions as well, but that’s a topic for another day. But it does also speak to Humphrey (and many men’s) limited mental model of how to meet women because they’ve been influenced too much by pick up artist social media content.

Then, he goes on about situationships and how no one is willing to commit because there always seems to be a better option on social media. Yet he clearly wants a long-term relationship rather than something short-term, so that’s on him to show he’s open to that. Because most women want a long-term relationship and constantly complain how sick and tired of hookups. I’ve lived and visited 40+ cities in the USA, including San Francisco (briefly), Austin, NYC, Miami, Raleigh, and DC. Women have complained to me in many of these cities about just this.

Therefore, I truly don’t think what Humphrey is complaining about is the real issue. In fact, it should be an advantage that he’s actually looking for someone long term. Any situationship he complains about is highly likely the fault of the man rather than the woman since women biologically don’t typically want short-term things. If he’s really struggling because all the women he dates are “looking for something better”, then he’s not conveying what he has to offer well or he needs to move out of SF as I’ve heard it’s just a terrible gender ratio that makes competition noticeably more difficult.

There are grains of truth in what he says, mixed with a lot of cloudy mud. San Francisco is an expensive place to live. It doesn’t hurt to get rich and not have to feel the strain on your wallet to go on dates and to be able to provide. There’s a lot of wealthy people there that lead with money. But leading with money can attract the wrong type of women and turn off other types of women. Plus, if your social skills and confidence suck, you’re in for a rude awakening still even if you’re rich.

Humphrey seems like a good guy like many friendly fellow Asian men I’ve met. I noticed he follows some dating coaches I do on Instagram. He’s on his way to a better life and probably has the income to invest in fixing his flaws. But he’s not there yet. It’s better to listen to some great coaches than someone who is still trying to figure it out.

Last but not least, his concluding thought to just keep working on yourself and the person will come along when you least expect it is a common piece of dating advice spouted by women that I think is horse crap. This “mean to be” and “it’ll all work out stuff” is a great way to make you feel mystical and feel better about yourself. It’s a great way to delude someone into continuing on a failing path and feel good about it. But just think of all the Jews who dies in the Holocaust after torture and starvation or the Africans who were captured, shipped, and enslaved for the rest of their life in North America. You think it was “meant to be” or “it all worked out?” And don’t give me that crap that some people like to respond with by saying that the pain of the Holocaust could have been worth it in the long run in bringing the world together so it is really was “meant to be” – there’s no need to justify it in that way, and it certainly didn’t feel that way for the victims. So, it’s on you to make the best of your life, rather than just leave it up to the winds of fate.

You can work on yourself but still fail because you’re blind to the traits and skills that are most impactful to improving in ways that attract women. It’s another fallacy to this idea. If you don’t work on yourself in the right ways, you’re not changing skills and traits that will level up your attractiveness and ways of meeting women. For instance, Humphrey didn’t mention his own looks at all, so I wouldn’t be surprised if he’s blind to the fact that he could do a lot to improve his edge, attractiveness, and physique that could help. And I’m not being mean as I am trying to help because Humphrey is me in a way. I also wasted years thinking I could make up for my glasses and Asian nerdy look with my personality or game … but it took a lot longer than it should’ve for me to realize that pick up artist idea that looks don’t matter for men is baloney. If someone told me sooner, it could’ve helped speed things up.

What you need is a great coach. Plus, you probably know some people yourself (I know I do) that are trending in the direction of dying along as they’re getting older and older and there are no prospects in sight despite “working on themselves.” If your results aren’t changing at all and you don’t like where you’re trending in the next 10 to 20 years, then you have to switch it up. I think even Humphrey understands this on an intuitive level even though his words say something else, because he does follow dating coaches I follow on Insta, and I wouldn’t be surprised if he’s signed up for one of them. No shame in that! I’ve written reviews and posted videos with a few myself.

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By Will Chou

I am the the founder of this site and I am grateful you are here to be part of this awesome community. I help hard-working Asian American Millennials get rich doing work they love.

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