Leonard Kim is not your everyday, run-of-the-mill personal branding consultant. He almost personifies the concept of “starting from the bottom.” He started his career living with his grandmother while cycling through a series of failed startup jobs and dead-end positions at big companies. Now he’s a personal branding whiz whose writing has racked up more than 10 million views and who counts more than half a million people among his social media followers.
In addition to this inspiring story, Kim is known for his unconventional approach to self-branding and building a following. Instead of presenting a squeaky-clean, successful image to the world, he says, try being open and honest about your struggles and failures—and how you’ve overcome them.
The Business of Business chatted with Kim to learn more about how he’s made it all happen.
This interview has been edited for length and clarity.
Q: Everyone, thanks for joining us. This is Akil Alleyne at The Business of Business. I'm here with Leonard Kim here today to discuss some inspiring aspects of his story.
I'd really like to just get a sense, Leonard, for our viewers of who you are, your background and how you came to be an entrepreneur and embark on your career journey.
Sure. So in the past, I tried a lot of different startup ventures and, you know, tried to get rich and all those things that a lot of people try to do when they're younger. But a lot of things just didn't pan out, and it was because of things that were outside of my control, such as budget and finances and how they were controlled or managed, and all of these companies continued to fall apart. Because of that, it became extremely hard for me to end up making a living from myself and just being able to survive.
That caused me to fall into a situation where I almost became homeless. I was unable to pay rent for a long amount of time; the lights were shut off in my home; I wasn't able to pay electricity; I had to shower in the dark; I had to get my phone charger plugged into the hallway of the apartment complex just to get it charged...things were extremely tough. I didn't know what to do because I thought I was going to end up homeless. I called my mom and I told her I had lost everything and I didn’t know what to do. She called my grandmother. My grandmother, bless her heart, was able to go and save me and let me stay at her place.
During that time, I went to work for another startup; things didn't work out too well there. Then I got a regular job, and I spent two years there. By the two year point, I was only making $16.25 an hour, which in California is enough to take the bus, not really enough to pay rent, enough to buy $90 of groceries a month, which doesn't really feed you that well. It was a really tough and challenging place to be...but I got to the point where I became sick and tired of being sick and tired, and I knew I needed to make a change. I didn't know what to do because I tried all these different things; they didn't work. So what was I supposed to do? I applied for hundreds of jobs; I got 3 calls back; no one hired me. I realized that getting a new job was probably going to be next to impossible. The only reason I even had the current job was because my friend was working there and she gave me a referral to get in.
I tried going back to school. School is a long term play; it takes years and years and years to finalize that out. And I was reading some content by James Altucher. He was talking about what it felt like to lose a lot of money very quickly, and once I read that post, I was hooked. I'm like, “this guy's just like me”—except that he made a lot more money than me and lost a lot more money than me, because I had only lost money, I didn't make that much.
So I started consuming his content on an everyday basis, I read every single thing I could, and a lot of his content says, “Go out there and do something; go out there and do something.” So after about a month of consuming his content, I felt a little bit braver, and I'm like, “I’ve got to try this, right? Maybe it’ll work.” So I started posting about my life online. But instead of talking about the good things, because I had no good things going on, I talked about the bad things. A lot of people were like, “No, don't do that! People are gonna judge you, you're never gonna get hired, your life is gonna be screwed.” But I thought, “My life’s screwed already; I might as well give it a shot!”
And I did it, and I got hooked. After a month, someone read that post and shared it with about a thousand people, and I got super excited. From there, I began writing every day, and it became engraved in me. I was excited about doing this; I wasn't looking at the results. I didn't know what would come of it, I was just excited to be sharing my stories.
So you would say that actually sharing some of the challenges and obstacles—and maybe even failures—that you encountered was actually beneficial? That drew in more attention from the public?
Yeah. I cover more of that in my book, “Ditch The Act: Reveal the Surprising Power of the Real You for Greater Success” with McGraw-Hill Business, which came from that. That was back in 2013, when I started writing; in 2020, the book comes out, seven years later. Writing about failures landed me a book deal with a major publisher—something that not a lot of people are able to accomplish and something that I never thought would be in store for me. But within six months of writing content, I got 2 million reads on it. I was named a top writer on Quora; in 2014, I got 10 million reads on my content. That grew into me booming and freelancing up to $5,000 an article for something I was writing—which was crazy, considering the fact that I was only getting paid $16.25 an hour. $5,000 from one gig was a sixth of what I made for an entire year of working 40 hours a week!
Then it just increased from there and increased from there. I started writing for Inc. Magazine, The Huffington Post, Entrepreneur; then it flipped to them featuring me and my story. Then they started showcasing me in the media, and I have over 300 media features in Fast Company, Fortune, Forbes, Inc. Magazine, and all these other places. That leveraged into this book, speaking engagements around the world; I got to stay at the Four Seasons in Istanbul, in a beautiful castle, and it's just so beautiful out there and they covered everything. I got paid to speak, got invited to go guest lecture at John Hopkins University, doing another MBA program—all these things I never thought would come out of my life after almost being homeless. And I've been able to work with a lot of successful people, help them build their personal brands and...life’s been okay!
So you were able to sort of leverage your writing and your personal branding online into actually creating value for other clients. Can you tell us a bit more about that? How were you able to sort of parlay the way you started out, and how you got your foot in the door, into actually creating a service that you could use to benefit your customers, thereby enabling you to make a good living?
So one of the things that I've always loved doing—and personally, I've fallen in love with people in general based on their public profiles and how they're structured and everything—and seeing so many people in the public spotlight, if you follow news media and look them up and follow their personal blogs and everything, I've been able to research a lot of the ups and downs that people go through and the mistakes that they made and what really drives and connects them, what really drives and connects me and makes me gravitate towards them. So I incorporated a lot of that stuff into the content that I was creating. And when people began to see the results I got for myself, they wanted the same results for them.
Interesting. So, can you give us an example? I think I've seen on your LinkedIn profile that you've been able to create a lot of value for certain customers that you've served. Are there any particular standout success stories that you're really proud of?
One of my clients, we worked on an article together, and that was read over a million times from just one piece of content. People do business with people that they know, like, and trust—but if you take things further and get people to fall in love with you, That's how you really make that connection and drive an established relationship that's ongoing for the rest of your life. And to get people to fall in love with you, you can't share these good moments, you have to share the good, the bad and sometimes the ugly as well, and kind of intertwine it all together. Most people, if you look at Instagram pictures, it's all about showcasing the very highlights of one's life, and people kind of do get inundated with it. They think, “I could never become like this person; it's not something I could ever do; I'm not relatable to this person.” But when you share the good, bad, and sometimes the ugly as well, then you become a lot more relatable—and because of that relatability, you’re able to connect with more people and grow massively when you build your platforms online.
Can you tell us a bit about your upbringing, your education? What did you study in school, and did it end up playing much of a role in what you do for a living now—or did you end up veering off on a completely different path?
So when I was aged 17 through 19—I don't remember the exact year—I went to a college called Westwood College, which is now defunct, and I majored in E-business. I thought I was going to learn how to build an electronic business—but they taught me how to build a computer, how to network computers together, how to do a little C++. I'm like, “I don't want to learn this stuff; this isn't something I want to do.” So I ended up dropping out.
I didn't go back to school until about 2013, and then, when I was at Glendale Community College—no major university or anything—I studied Business Administration, so I could learn about the legalese, how to run a business, and things like that. I took a lot of communications classes, because I really enjoyed communication. I think my favorite class in college was actually Ethnic Studies, because it showcases so much of what goes on in the world that I never even knew about. I'm like, “There’s so much discrimination and all this stuff, this is something that definitely needs to change.”
I think last year, I was invited to potentially become a student at NYU Stern's business program for a Master's program. A few months ago, I was approached by Pepperdine to be a part of their MBA program. And I'm someone who doesn't even have a Bachelor's degree! Now, I don't know if I want to go and pursue that education, because it's, like, $200,000. That's a lot of money, like a Lamborghini, and I don't know if I want to go and invest that right now. So that's something I'm debating about whether I want to do in the future or not. But as things have gone so far, having as much education as they have, community college helped a lot—but a lot of my experience comes from the real world and facing most of those challenges in the business world.
That's actually interesting. Do you think that your experience has [...] any lessons to teach to young people—maybe teenagers today in high school, who are trying to decide whether to pursue a college education or whether they should maybe dive into the job market and try to gain experience? Do you think that your experience has anything useful to offer people in that position?
Well I, I value college, I don't value the $100,000 price tag that comes along with it. Education is extremely important—being able to find mentors and be taught the ropes, and learn the insights. Like, Business Law: If you don't take that class and you try to do business, you're going to probably get into a lot of trouble that would cost you more than that class itself. Accounting: I suck at accounting, but I got a B in class. I realize the importance of it and how important it is to have an accountant who can handle those things for me. Going to school lets you realize what you're good at and what you're bad at, so you can figure out what you need to do yourself, what you're passionate about, and what you could allocate to others to do because it's just not the strong suit within your personality, if you know what I mean.
But then, having that real world experience is good, too, because you get your feet wet and you get to figure out what you actually like and don't like as well. The problematic part is a lot of people go into college, and they don't actually know what they want to do, so they make a random guess; then they spend four years; and then they're doing something that they don't actually want to do.
I know that you mentioned—and you also mentioned this on your LinkedIn profile—that you were involved in a number of startups that failed. What were some of the experiences that you had working on those projects, and what lessons did you learn from them that you find useful in your current journey?
I think it was an extremely heartbreaking process, being from the Asian culture. A lot of Asians tend to fall in love with their work; it becomes like their wife, right? It felt like my wife kept dying!
Yeah, and then going through that heartbreak. Not only that, let's say you do have a wife at home, and she cooks and cleans for you and takes care of the house and shows you love and compassion. A job or a business, in the same way, takes care of you by providing the finances so you can buy your own food, so you can have shelter and all of these other things, as well as an automobile so you can drive to and from work. It gives you the necessities that you need to go out there and survive and take care of yourself. But then, when things fall apart, that falls apart, too—so it becomes the emotional struggle of trying to go out there and deal with survival over anything else. Because it's not just the emotional heartbreak that you have to go through; it's figuring out how you go out there and survive. And I went through so many heartbreaks myself that I just kind of gave up and I was like, “I just can't do this anymore.” It's too hard to continue to go and try over and over and over again, and that's why I ended up in the situation I was in.
It sounds like a big part of your story is taking negativity—or at least, what on the surface looks and feels like negativity—and turning it into something positive, just on an emotional level? How were you able to sort of pick up the pieces and keep pushing on in those moments?
Well, a few years ago, I know, in popular culture—especially in the startup scene—they were like, “Fail fast, fail fast, fail fast.” I don't buy into that, because failure is extremely heartbreaking. It's traumatizing. You have to go through a lot of personal development, self-growth, reflection—asking, “Is this my fault? What really happened? What can happen the [next] time?” But that only happens after you go through that “Oh my God, my life is over, I don't know what to do, I'm dealing with so many struggles and everything.” And it takes a lot of time to overcome each [one] and the more failures you have, the harder and harder it becomes to pick yourself back up and dust yourself off and try again. So while failure is important, and while it does shape who you are, it's not something I wish upon anyone.
Interesting, interesting. I'm actually really glad that you brought that up, because there is a sort of narrative out there that's popular in society that you have to be persistent and persevere, and when life knocks you down, you dust yourself off and pick yourself up and try again. And that's true—but at the same time, like you just said, getting knocked down is a painful experience, and bouncing back from it is a painful process and it's easier for some folks than it is for others. I think I remember reading somewhere in the past that you do need to take some time to grieve, almost, and sort of absorb the defeat, and get over it fully before you can move on. Would you say that that was something that you were able to do—especially after you may have suffered numerous defeats or encountered numerous obstacles? Were there any specific techniques that you used to help speed that process along?
You know how in therapy, they kind of ask you a lot of questions, and then you work through these questions, and then you kind of learn more about yourself, and then you have the “Aha!” moment? I kind of did that with myself, where I turned back and reflected upon myself and had to ask myself these questions. I didn't have a background in psychology or anything like that. But then, I have a therapist nowadays, and a lot of the questions that he asks me are very similar to the ones I asked myself. So I don't know. There has to be...a common thread based on the questions that you kind of ask yourself to really go out there and overcome these situations.
Right, right. And so looking forward, what do you envision in the future, maybe the next five to 10 years? Do you envision expanding your business operations to any new domains that you haven't covered yet?
My business has touched a lot of places, like Italy, a lot of other places in the United States, overseas in Asia...and it's kind of had a pretty big impact. I see it continuing to grow. As far as the big things that are going to come in the future, these aren't things that I kind of look out for, but hopefully they're things that come. I realized that when you have expectations, you kind of put limits on yourself, and you kind of get frustrated because you try to get towards those expectations, and it causes more harm than good. But when you have no expectations, you're doing something, and when a result comes in, you're positively surprised, and you kind of take advantage of it. Hopefully, one day maybe in the far future, I can become maybe a professor who can teach my business lessons at some kind of school.
Well, I guess you did mention earlier that several universities reached out to you to try to recruit you for their programs, right? So I wouldn’t be surprised if that does turn out to be an opportunity that's available to you.
We are The Business of Business; our focus is business. What insights do you think your experience can offer people who are already in the business world and those—particularly young people—who want to get into the business world, or maybe people from other professions who might be considering transitioning into starting their own businesses or what have you? What do you think are the main takeaways from your experience that can be useful to others?
So many people focus on trying to build up their business brand, but then with their business brand, they're limited to a corporate image, and they have to stay within the guidelines and limits [of] exactly what they could do or say, because they're constrained by the company mission and the company's products and services. So then they're not able to fully go out there and share exactly what they want with their audiences. On the other hand, as a consumer, a lot of people, when they gravitate towards these company messages, and they read it, they automatically assume that it's completely polished— that it may not be the full truth, because it's a corporate image, and they feel that there might be a lot of padding within it. With a personal brand, compared to a company brand—even with legacy brands like Amazon, like Adobe, like IBM, Cisco, and places like that—if you go out there and you build a personal brand as opposed to a corporate brand, your results are going to be at least 10 times higher than what you would get as a brand message itself, because people are looking for people that they know, like, and trust, and hopefully fall in love with. But then, if you have a logo and a company, it's very hard to fall in love with a company, unless you're, like, Oreos or something.
A longstanding brand that is famous in its own right and it's been around forever—that sort of thing. Right, I can see that. I’m glad you just mentioned that distinction between personal and corporate branding, because that's something that I don't think always occurs to a lot of people, and probably wouldn't have occurred to me if you hadn't brought it up. So thanks a lot for that.
When it comes to branding, I do wonder. Because I've known people who...went to university and they studied marketing and that sort of thing at the undergrad level, at least. I do wonder: Do you think that's the kind of thing that it's advantageous to go to school to learn? Or is that the kind of thing that you can pick up on your own to experience more efficiently—or is it more or less even either way?
Well, school teaches you the fundamentals. Like, these are the four P's—price, product, [etc.,] and then they teach you the basic fundamentals of how to do the marketing. It's like the mechanics behind the scenes of how it all works. You can learn those mechanics anywhere; you can learn it at school, you can learn it in the real world—it doesn't really matter. But there's theory, right? And then there's actuality. A lot of people teach in practice. I remember when I went to Glendale Community College, I had to do a simulator for business growth for a $200 million company. I would click on these different things and make different results, and it would change this company drastically. But if you do that in the real world, and you try to go get your coworker to change his mind and do something else, they're like, “No, I'm not doing that. Oh, we’ve got to hold a meeting; oh, we’ve got to make these changes.”
So while theory is important, how things react in the real world is extremely different, because there's a lot of different politicians...and stakeholders and businesses who kind of dictate direction. So you can't make these moves as freely as you can in a simulation or anything like that. So having...that real-world experience is important, because then you get to understand the human component of how everything works.
Just making a product at $5.99 does not mean it's going to sell. You have to understand the public personas of the people who are buying it. You have to understand what kind of people are buying it, what are their personalities like, what do they do? And while you can learn how to gather that data from school, you don't really know what it really looks like until you're in the real world, if that makes sense.
So in a nutshell, to wrap up, what concise advice would you offer to a young person who is maybe looking to get into the field of business—maybe a lane similar to yours—but who's also been knocked down a few times and is on the verge of giving up? If you had to sum up your overall insight for them, in a nutshell, how would that sound?
So I think one of the scariest things for me was at the moment when I lost everything. I was scared to tell everyone...the exact position I was in, because I thought I would be judged, mocked, ridiculed, called a failure, and all these other things. But the nice reality of everything is that people are a lot more compassionate than you might think. When you open up about your vulnerabilities and struggles, people want to help you get out of situations and offer a hand and help lift you up.