Transcript: Learn It All Mindset with CEO Damon Lemby

Host: Welcome to the show.

Guest: Uh, it's great to be here. How are you doing today?

Host: I'm doing good. Um, so, you know, you're the CEO of Learn it. Uh, you've done a lot in terms of, you know, education and upskilling, almost 1.8 million people. Uh, you've written this uh book, uh, all about, you know, how to learn.

Uh, and you also have this amazing learn it all podcast. So, I think this episode is going to be all about learning and how we can learn. So, uh, welcome to the show again.

Guest: Well, thanks for having me and it's uh great to be here.

Host: Uh so, to start off, um, you know, can you uh give a little bit of context in terms of your journey on how you, you know, came to work uh on learn it?

Guest: Sure. So, my name's Damon Lembi. I'm born and raised, I was born and raised in San Francisco, California. I grew up and as a kid, um, for me it was all about sports. When it was baseball season, I played baseball and I played football.

And so that was it through in through high school, I always wanted to play uh professional sports. And I realized by the time I was a sophomore in high school that baseball was really my best opportunity. So I put a lot of effort into that.

Um, I was a, I turned out being a uh high school All-American and I was drafted by the Atlanta Braves out of high school. And I had this opportunity. Do I go play professionally or do I go take a full ride to Pepperdine University?

Uh, I ended up going to college route and got hurt at Pepperdine, left. Uh, got another opportunity to go at Arizona, to play at Arizona State, one of the best schools in the country.

And I thought that, um, after having a couple good years there, I was going to be able to continue my journey into professional baseball. Sometimes things don't turn out the way you wanted to.

And uh, I wasn't drafted again and here I was, 22 years old, thinking to myself, well, I identified as a baseball player my whole life. This dream's over with. What do I do now? And are my skills even transferable?

What what can I do that I've learned playing baseball in the in the business world. I was really fortunate. I come from a family with uh a lot of uh businesses from real estates to restaurants to um even a hotel chain.

And uh this was back in 1995, my father Walt was starting a computer training company. He went and took a class somewhere. He thought it was boring and slow. So he came up with ideas of small bite sized classes. That's where learning came up.

I started there as a receptionist, um, and I kind of worked my way up over the years and from teaching classes to doing sales and we've kind of, well not kind of, but we've transitioned from being just a computer training company to being an overall corporate training uh company and we help customers when they're looking to upskill new managers, roll out you know, new programs, onboard employees and that's really what we've done.

And like you mentioned, been fortunate enough to train over 1.9 million individuals over our career at Learn it and what's really made me the most excited is the team we've been able to develop and we've had a great team.

And I share all of these in the book you're referring to, uh the Learn it All Leader, which kind of talks about and I'm sure we'll get into it, but what a learn it all is versus a know it all and how that could positively impact not only your organization, but uh your leadership style.

Host: Um, so talk to me a little bit about, you know, how sort of training and upskilling changed from when you first started in 95, um, to now and sort of how the business evolved and what is the size of the business today and all that.

Guest: Great. That's actually a great question. Back in 1995, it was everything was typically in person. You know, this is kind of pre-internet.

And everything was in person and uh you'd have your physical printed up books and you'd sit in there and sometimes these classes would be two to three days long. And think about that, sitting in a three-day class to learn how to use Excel.

And um and that's what kind of how we kind of disrupted the market back in the day.

You know, one of the things that my father always said is you got to have a unique value proposition and and do something a little different or else you're just vanilla and get lost.

And so we came in and our the way we taught back then was everything was in 90 minute bite-size segments. And that helped with retention, flexibility in scheduling and also like really honing in on what you wanted to learn.

Say for instance, if you just want to learn pivot tables, you don't have to sit there for two days to figure it out. And as you see with a lot of startups that actually make it, a lot of people thought we were nuts.

Like, there's no way this is going to work. This is how we always do it.

But we tried something a little different and that's and that's really, if you look at how the training world is now, everything is short, modular, bite-size, gamification, on demand. So it it's a complete shift.

The training, the corporate training world is about a $160 billion a year industry, uh which is I think back then was closer to probably 20 or 30.

So it's dramatically changed, improved and uh it's one of the things that especially the younger generations, people are demanding the opportunity to learn and grow in their position.

Um because a lot of times they're not looking at as, okay, this is a job I'm going to work at forever. I want to pick up the skills I need to be able to continue on in my growth.

Host: So, I think you, you, you know, running a company of this scale would have a great vantage point in terms of like, what are people actually trying to learn and what are companies want their employees to learn. So, talk to me a little bit about, you know, what are the trends that you're seeing about, you know, what people actually want to learn.

Guest: Yeah, it's definitely changed over time. And I think one of the great, one of the great things about learn it for me personally is I've been able to evolve our company. We're small. We have about 75 employees.

But I've been able to see behind the the curtain really of of what some of the largest organizations in the world um think about and when it comes to people development and to leadership.

So, what most of the organizations look for and need these days, as far as what learning core is really, is a lot around new manager skills. You know, a lot of individuals are getting promoted into leadership roles for the first time.

And as as you're aware, it's a totally different skill set.

That's a different as you as an individual contributor, whether you're somebody on the accounting team or in sales, transitioning into a leadership role is a big, is a big jump. is a big change.

So, there's a lot around focusing in on leadership skills. Now, obviously, with COVID, there's a big shift to everybody going to work remote.

So, how do, how do organizations, how do they use the tools at the time, whether it's Zoom or Microsoft Teams or Asana? How are the, how are they using these tools successfully, um, or more successfully.

And how do they learn, how, how would they learn to be able to trust their employees and and keep them accountable without having them physically in different locations.

And for a lot of our customers, some of the the largest companies that we work with, that was a big challenge. It was a big shift in mind shift.

And then when things, when the world went back to let's say a hybrid approach, that was another big shift because now you tell everybody, okay, you're going to work remotely forever because we don't know if everything's going to come back to what it was and now the cat's kind of out of the bag.

So it it's a big challenge getting people to come back into the office.

Outside of, outside of learning and development, I also have invested in a lot of real estate over the years in commercial real estate and so kind of uh that's been a challenge for all of us out there is getting, getting the employees uh to to to want to come back into the office even for a couple days of the week and and seeing the value with that.

So, what we try to work with our organizations around, our, our customers is showing value for their employees to come back into the office so that when you, when you are back in the office, there's actually a purpose.

So, it's not like everybody's back in the office four days a week and they're just on remote calls all, all the time.

How can you get people back into the office with purpose, collaboration, and um, so that, that is top of mind these days as well, of course, what everybody wants to talk about and I'm a big fan of and I know you are as well with your 100 days of AI growth is uh AI and and how, how is AI not only going to impact uh learning and development, which it is, but the the overall, the overall workforce.

What's going to happen with the employees? What are the skills they're going to need? And it's going to be a major shift in in how the world's moving.

Host: I think, uh, since you brought up AI, uh, you know, one of the challenges, I think, you know, product managers or, you know, managers in general, everyone is excited about the technology, but people don't know how to sort of get the buy in from leadership.

Uh, right? So, have you seen any trends or like ways to sort of, and as a, as an educator, people helping do this stuff, right? How, how do you get that buy in?

How do you sort of convince that your team or your leadership that, hey, we have to go do this?

Uh, and, you know, because there's also, whenever there is hype, people sort of tend to say, let's take a step back, let's see if this thing will, you know, this thing sustains uh, the hype that it has and then we'll do something.

So how, how are you looking at in terms of just uh, you know, how someone working at a company can, you know, push their push people around them to sort of focus on this, um, uh on AI initiatives.

Guest: I think it's a great question. And you know, there's a couple ways to do it. I I I I personally think if it comes top down, let let's say the senior leaders in the organization are like me and they're all gung ho about uh AI.

And then you try to push it down on your team, you know, there there's still a lot of, you know, people are worried. Is this going to take my job? You know, is it secure? Is it going to steal all my information?

So it's it's really like a lot of change management initiatives, there needs to be a lot of communication and being clear with what the goals are.

What I've kind of found and what I've tried to do both internally for our organization and I've seen others is have it come from the ground up. Have it come from the individual contributors within the organization.

Give them the opportunity to have use chat GPT, use superhuman, use all these tools out there available. You know, invest in them to have it and give them the time and space to to use them. And um and and until, I mean, to leverage them.

And then give them the opportunity to share with their team some of the successes they've had and in how they've leveraged these tools whether to be more efficient or or or to have better at research, whatever it is.

So try to build up the excitement throughout the organization. A lot of times at the individual contributor level can can be can have a a ripple effect that will lead to a positive outcome for organizations.

And I think all this kind of comes back to what we were mentioning earlier is having, what, whether you want to call it a growth mindset or a learn it all attitude, it's having not having the attitude of the, the know it all.

Like, this is how we do it. This is, this is, there's, this is how it's going to be. Well, what I like to tell people is you're not going to lose your, I don't think you're going to lose your job solely to AI.

I think you're going to lose your job to individuals who know how, who learn how to leverage AI, who are power users or at least have the learning agility, which by the way, I think is one of the top skills or maybe just the top skill out there today and that they have the aptitude and ability to go out and learn these tools to to grow in their careers.

Host: So, I mean, uh, you bought up learn it all, which is, which is also such a great phrase.

You know, I worked at Microsoft and one of the big tenants in Microsoft is growth mindset and the way Satya defines it is learn it all versus know it all.

And you, you when you closely look at that just that six words, you can sort of encompass all about, you know, growth investing.

Talk to me a little bit about, you know, what makes, you know, someone learn it all versus know it all and how do, how does that look on a practical sense, um, you know, when you're uh doing your day-to-day job.

Guest: So, let's start with a know it all. We kind of talked about this a little bit. A know it all is somebody who, who comes into the conversation or come and and they have it all figured out. They're always right.

They're not open to listening to what anybody else has to say and it's my way or the highway. This is how we do it. This is how we always done it. Now, on the flip side, you, you have a learn it all.

And to me a learn it all and yes, it's it's big at Microsoft, you know, the growth mindset and everything. But to me a learn it all is somebody who comes in and says, I don't know everything.

And I'm going to keep an open mind, a flexible mind and be willing to learn from others, not being afraid to say, to be vulnerable saying, hey, you know what?

I don't I don't have this all figured out, getting diverse opinions, learning what other people have to say. Being, I think a lot of it is being curious. Being curious and interested and and learning to adapt. For me, I I call it learn it all leader.

My definition of a leader, you don't have to lead a 50 person team, 100 person team or be a small business owner. I think we're all leaders.

You know, it all starts with self-leadership and with that, you can have the skills and the ability to want to always continuously grow, continuously learn and continuously grow.

And the key traits that I really look at is humility, uh to have curiosity, to always be curious like we mentioned, integrity. I think it's always important you want to do the right thing. And then also courage.

Now, I'm not saying the kind of courage that risk-taking, I mean, maybe bold decisions when it comes to work, but what I say in courage is step out of your comfort zone. Don't be a try, you know, uh don't be afraid to try something and fail.

You know, learn from your failure. I those are all to me the qualities or the traits that are that are necessary to to be a learn it all and to continue to evolve and grow in your career. Personally and professionally.

Host: Yeah, so one of the things, I mean, I often sort of think about when I do things because, you know, I do couple of things outside work is uh, you know, sort of the imposter syndrome.

Like, uh, I was judging an event the other day and I felt like, you know, whether I should be judging, you know, other folks, right? It's sort of like uh a classic imposter syndrome.

But then after the event I felt like because I saw so many deals, I, you know, invested, then okay, I rationalized in my mind, okay, I definitely did more deals than some of the other folks there, so I sort of rationalize that, you know, okay, maybe I don't have to worry about imposter syndrome.

But, you know, it's sort of like a constant struggle I see with a lot of people and it also sort of, um, I would say slows down people's careers because people always think that I'm not enough or um, you know, I'm not yet there to sort of take a plunge and take the next step, you know, either career wise or something that you want to pursue uh to making that ideal career or ideal profile for yourself.

Uh, how do you, I and I know like you wrote a lot about imposter syndrome and how to overcome that. So how, how does one overcome imposter syndrome?

Guest: So, first of all, I would say everybody struggles with imposter syndrome at some point in their life. If if they don't, they're, if they tell you they don't, they're either lying or a sociopath.

So, you know, for those of us, for your listeners out there who have struggled with imposter syndrome, self-doubt, didn't think they believed, you're not alone. It it happens, happens to all of us.

My real first experience with imposter syndrome was going back all the way back to when I was at, when I went from being a high school All-American in baseball to college. So you're used to being like the best player around.

You know, nobody even close. Then you get into college and everybody is as good as you or better. And you know, for the first time in my life I thought to myself, I mean, do I even belong here? Am I good enough to be here?

And unfortunately at the time as a 17-year-old kid, I didn't really have the tools or the mindset to to to make it work and and that's kind of why I I I I failed that originally at Pepperdine and it took me by the time I got to Arizona State to learn how to deal with imposter syndrome.

And really, I build a formula.

I use a formula that uh or a framework so to speak on on on how to overcome it and the first thing is you got to identify what you're upset about or what you're worried about and and it could be, I'm just promoted into a new role as a manager.

Uh, I don't know why they promoted me.

I don't think I'm good enough to even get the job done or um, I really want to go in on this investment but what if, what if I give my advice and it doesn't work out and and people lose their money or my group, whatever it is.

And so first, identify label what you're worried about. Then the second thing is a a coin that I termed called purposeful awfulizing.

And so what I mean by purposeful awfulizing is let's use the example of of being promoted into becoming a manager and then you think to yourself, okay, if I take this job and I completely fall flat on my face, in a year from now, what's the absolute worst thing that's going to happen?

And let's say that maybe that I lost my job. Maybe that's the absolute worst thing that can happen. Well, I can go out and get another job. It may be tough, but I can overcome the worst case scenario.

So, if you've realized that you could overcome the worst case scenario, then go for it. And that moves into my little framework that I have is, so there's a, it's a three-step framework. Number one is work hard.

I'm not saying put in 10 to 15 hours a day, but I'm saying put in hard work and just there's no short, shortcut for hard work. You, there's no hack for it. You have to put in the hard work. You got to roll up your sleeves and do the work.

Number two is focus on what, what your challenges. Deliberate focus. It's really easy when something is tough for you to lose to lose sight of it. It's you know, let's say you're working on a big project at work and it's you're stressed out over it.

It's really easy to get distracted and and go do something else, even busy work to get it done. But no, you have to work hard and you have to be really focused and put in the deliberate practice. And then my, the third step is learn and let go.

So what I mean by that, let's say uh you're you're you're worried about giving a presentation. You know, you're not a great public speaker and but you're you've you've accepted an opportunity to do a speaking gig.

Well, if you've worked hard, if you've put into practice and you've really focused, when it's game time, it's game time.

You leave leave all your techniques, not, I mean, stop thinking about what your techniques, stop thinking about what you're going to do. Go in there and give it your best shot. Do the best you can do.

And it might work, you might work out great, it might be terrible. But at the end of the day, I think people don't give themselves enough credit. Give yourself a pat on the back for even trying.

And through every opportunity successful or failure, you can learn from that. A lot of times you can learn from failure even more. But pat yourself on the back for for sticking your neck out there and trying it because a lot of people won't even try.

They'll just sit, like you said, they'll say, well, I'm not good enough. What if I, what if I don't do well. Well, here's a little news flash as well.

You don't do well in a presentation, well, maybe you lose a deal or or maybe you're you're giving a talk somewhere and people laugh or they're embarrassed. People have their own lives.

They don't, they'll think about that, honestly, for about 5, 10 minutes and then they'll move on. You know, you're not, you're not necessarily all the time as important as you think you are.

So, uh, get, get out of your own head, um, put in the work, put in the practice and learn and let go. Learn from what you're what you're upset about or you're worried about and just give it your absolute best.

And to me that's really also an epitome of a learn it all too. It's having the courage um to step out of your comfort zone and and try something and learn from it.

Host: Yep, uh, so one of the uh ways I sort of block my imposter syndrome is uh there's this great quote. I forgot who said it, but uh, you know, everything great that you see around you is, you know, created by a normal person like you.

I'm paraphrasing it, but um, that that's sort of like the uh essence of it. So I always use that in my mind that sort of like, you can go and do things. The worst thing is you'll fail.

And that sort of quote is basically also motivates that, you know, everything, like you will not become great if you don't, you know, sort of go and do it, right? You have to do it, take your chances.

There's no other like way other than just going and doing it. Um, Yeah.

Guest: I agree with you. I mean, I I I I think all of us have to learn how to get comfortable with failure and and get comfortable with learning how or learning for to hear the word no and and to to deal with failure.

And I think it's it's great what you said. I mean, for you and your investing and and and the work you do, I'm sure not everything goes great all the time, right? So you have to, how do, how do you overcome it?

Host: Uh, I mean, the only way I always look at is, okay, what is the worst thing that you already said about? Like what is the worst thing that could happen? And let's say you got into podcasting. What's the worst thing that can happen?

Like no one listens or you might, you know, get nervous during the recording, but you, you can, you always have the choice to not publish it. So there's no fear of anything really.

It's sort of like, I think most of the fears are they're bigger in our mind than uh in reality, right? So I think, you'll fail. And the only thing I would say is in all the bets that you take, never risk ruin.

So for example, if if you know that there's a risk on any investment, don't invest everything into it.

That's the only thing I sort of um tell people, like, you know, you take, you can take any number of bets as long as, you know, they're not ruining you completely. Uh, so I think that is sort of like the balance we need to strike.

Uh, so I don't want to do a public speaking gig so outrageously that it will destroy my life. So that is a risk that you're taking, right? Um, So that's not a risk worth taking.

Uh, so there are certain, so that's how I sort of reframe risk and then most risks are actually not risks.

Like even I tell uh people who start companies is a risk taking thing, they really didn't look at it because, you know, there's investment dollars available. You have people ready to work with you.

If everything fails, you can come back and do the job that you're doing. So what is the real risk here? You're still getting paid while you're doing that company.

So these are most of the times I think the risk, the true risk we sort of over exaggerate in our mind itself. Uh, so that's how I rationalize it uh, you know, in my mind.

Guest: I think you bring up, I think you bring up a really good point and what I didn't add to the whole purposeful awfulizing, which is basically the same thing you're saying, but in another way, is that if you look at it and the worst case scenario is you lose your house and you go bankrupt, well then don't do it.

You know? Don't, don't do it. You know, only only do the size of the bet that you could afford to lose. So, you know, think that through. And sometimes people aren't rational.

They get all excited and they're like, oh, this is a, this is a sure win or I'm going to, I'm super passionate about starting this company and I put my all eggs in one basket.

You know, I I think you really have to take a step back and think through uh what what what the scenario could end up to be.

Host: Yeah, and there are founders who do that like they put whole life savings into it. Then you're doing the wrong bet. You I mean, you're taking the right but in a wrong way. There are right ways to take the same bet. Uh, is what I would say. Um, but uh, you also talked about this concept called trust tax. Uh, tell me a little bit about that more.

Guest: Sure.

Trust tax, what I mean by a trust tax is, let's say we all go into relationships and whether it's at work as a, you know, a manager to an individual, you know, to your direct reports or or just personal relationships and nobody has a perfect perfect perfect record.

You're going to get burned at one time or another. But there's really two ways to go about it. You know, as a manager, let's just use a business perspective. As a manager, you have really two choices.

You could, you could trust your employees, you could, you know, that you've given them the skills and then you you could put them off on an assignment or whatever their tasks or responsibilities are that they can get it done, or you can be skeptical and you could be looking over their shoulder all the time, right?

You could do one of the two of those ways.

In a professional relationship, you can trust that whoever you're working with or or whoever you're friends with has the best intentions or you could always come into slide into every relationship thinking this person's going to, you know, screw me over.

I the trust tax, I believe is you're you're better off going into relationships giving people the benefit of the doubt, believing that people have the best intentions.

I mean, you got to be smart about it, but giving people the best intentions and 90% of the time or if you live in California, 60% of the time, it's going to work out and the other, you know, what I'm making a joke, but the you got to pay the tax.

So the tax is the time it doesn't work out. I you know, I'll give you an example. This is, this is going back about eight, eight or nine years ago.

Uh, one of our uh senior level leaders um on the product development side, curriculum side, asked to go to a a conference and um said, sure, send them, send them off to the conference, you know, it was a full week.

It probably cost about eight to 10 grand. Um, great. Great investment. You know, as a you know, as a company that does training for people, we want to invest in our own people.

The gentleman came back, he stayed, waited till he collected his uh annual bonus about uh two months later, then quit and took a job for the the the people who ran the conference.

You know, and that's to me that's not a lot of integrity and and it's uh, you know, you it didn't turn out the way you wanted to. But that's not going to prevent me from sending people to conferences again.

That's not going to prevent me from giving somebody else a chance.

You know, I'm going to believe that people have the the best you know, the best intentions and at the end of the day it's going to happen every once in a while where they where they won't.

But overall, I think people will surprise you and people will do a great job and that's just the way I've I think there's too much uh takes too much effort to put negative energy into something and be smart, come in a relationship with open eyes, but um give people the opportunity to prove you're right.

Host: I think there's another sort of um trend that we are seeing is this idea of uh, you know, your company is not your family.

Um, and I think more and more especially in the remote first world or recently what we have seen even in like, you know, how uh, we have seen a lot of layoffs and you know, some of the biggest companies as well and um, we often see that I think during non recession or non layoff period, we often use this phrase that, you know, my team is my family and stuff like that.

Uh, so talk to me a little bit about, you know, your philosophy of how do you look um, how should employers, you know, look at uh their teams uh our the company that they're working for.

Guest: And I think this is important for your listeners out there who are running a startup or maybe a small business or, you know, or on the flip side if if if you're an employee at a company uh and and you feel really loyal to them.

I I have a lot of friends, a lot of friends um that I've made through my relationships working at learn it and uh who are alumni.

And but the reason why I believe that you should treat your company as a team instead of a family is for sports terms, as a leader, it's your responsibility to put an elite team on the field at all times. Okay? At all times.

So if you're a startup, you know, series A company and you're just getting off the ground, you might have a you know, somebody who's great at the uh at at a director of operations role who can, you know, manage your manage your team at 10 to 50 employees, you know, up to let's say $5 million in revenue.

And then things take off. That same person may not be the person who's going to get you to 50, $100 million in revenue, who can run these larger teams.

And at that point, it's it it's tough, but you know, as a leader as a as a founder, you you have to make bold, tough decisions and you have to always constantly put your team, the the most elite team out there that's going to be able to help you scale and get you to go where you need to go.

Now, I'm not saying just walk in one day and and fire this person. You know, work with them and give them a heads up, like if there's if there's another role in the company where they can crush it, great.

Otherwise, I've had plenty of conversations with individuals who have been at learning a long time who have hit their capacity and sometimes it's just like, hey, you know what? This is just like you know, you're doing this on auto these days.

You need to go out there and stretch and go do something different, you know? So we're we're we we're buddies outside of work. I I appreciate all your loyalty, but you know, you've reached your capacity here and you need new challenges yourself.

So whether it's from the organizational level, the leadership level or for your listeners out there who are um individual contributors or or leaders that don't feel like that you you have to stick with where you're at all the time.

You need to continuously learn how to grow and and evolve in your in your career. I'm not saying take a job and leave it leave it two months later, but don't stick around for years at a company because you think it's like you owe it to them.

Host: Um, so you did, you know, well, uh, as someone who's running a company, uh, and this is a podcast where we talk a lot about investing. Uh, so I wanted to ask like how do you, uh, what is your sort of investing philosophy and how does, how do you like split your investing between, you know, different asset classes?

Guest: Yeah.

So my investment philosophy is is to first off, well, for real estate, it it's trying to, you know, look at the comps in the areas and try to forecast what things are going to be like in in the future, which obviously uh is really rough right now, especially on the, on the commercial side.

Now, on, on the non-real estate if we as far as investing in startups and whatnot is try to understand more about the actual the the leadership team. Who's on the leadership team? You know, what is their their past success?

What you know, what are they going to be able to execute on what the the product is that they're launching and where does it fit into, where does it fit into the to the market?

I mean, right now there's so much out there around AI again, that we're talking about, AI and crypto. Crypto, which I don't, I don't know much, much about. Um, my my investing um, you know, it also, I also really want to get in and learn and and talk

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