Ep06 Brian Cressey, CEO, and Venture Capital Pioneer: Leadership Development podcast

Welcome to Leadership Messengers Podcast. I am your host, Ovi Vasquez, born and raised in Guatemala with no electricity, now bringing you experts to help you develop our next generation of values-driven leaders.

Great CEOs and entrepreneurs drive quickly. They switch lanes because they're impatient. If they're impatient, it helps their chances of succeeding. People that drive slowly and cautiously may be suitable for other specialized jobs, like being an accountant or something like that, but nothing where you need to be aggressive. My wife is a surgeon and she drives carefully, but surgeons have to be ultra careful and detailed about every step when they're opening people up and, and sewing and things. And so that's appropriate. But for entrepreneurs, And CEOs and executives, they should drive a little faster.

Welcome to the Student Success and Leadership Podcast, which those of you who will watch the video will see this video as well. We have Bryan Cressey, a phenomenal gentleman who is very generous, generously sharing his time so that now he will share his wealth of knowledge and wisdom with us about his life. And let me just share with you that I came across his Instagram page first. As soon as I saw that he had some YouTube videos, I watched all of them as a marathon. So you can guess, you know, why would Ovi put some of his time aside to watch all the videos at once in the channel? I could not stop watching. So much knowledge, so much wisdom, and his delivery style is very engaging. And so I just love his storytelling style as well. So Bryan Cressey, I don't have the, you know, normal corporate introduction that you get, being that you have such a successful background as a businessman, but I know that in your story right now, everyone would learn the level of achievement that you have achieved and why they would benefit from it. So Bryan, welcome.

Thank you, Ovi. I'm happy to be here and excited To talk to the students and the educators.

Awesome, awesome. So I was, you know, I was reading your book and I have it right here. And in all your videos, you also pull it out from somewhere. I was like, yeah, works like magic, right? I appreciate that you sent me an autographed copy, personalized. And so in, in the book you shared, if you— if someone would ask me about how do you, do you define Be a Winner, the book, I would define it as a college degree in a book. I mean, there's an entire college degree in this book because you talked about gratitude, you talk about the business advice, you talk about entrepreneurship, but you grew up with some challenges, right? But you were very special and you are still very special. But tell us about your growing up time, especially the time that you had your own Christmas tree, your own little tradition that you made up. I know people will appreciate that very much.

Yeah, I grew up in Seattle and kind of a middle-class family. Um, I, when I was a boy, speaking of the Christmas tree, I liked to climb very tall trees and I strung wire up for shortwave antennas about 70 feet up in the air. And luckily my parents let me do that. Um, when I was teenage years, I would go to the Christmas tree lot and buy a little old worn-out tree, didn't have many limbs, and then I'd pick up limbs off the lot. And when I got home, I'd wire them to the tree, and that would be by our front door to welcome people. So every year, I loved doing that. I had part-time jobs, and eventually I decided I'd go to college. And I went to University of Washington. I worked part-time. I had a driving job where I drove at night.

Uh-huh.

And, um, unfortunately, I'd fall asleep sometimes in class. After about 2 years of college, I was a little bit bored and wasn't getting the grades I wanted. So, I stopped and went to work. And I worked for a company that made, sold, and repaired conveyor belts. So I got to go repair conveyor belts and learned how to do that. After a year, I wanted to go back to school. Then the grades came easily after that, and I graduated and decided I'd go to grad school. And so I went to law school and business school, and during that time I decided I want to help build young companies. That's what excites me, help growth companies. And so I Got in the venture capital business and started helping to build companies. We invested in them, helped build companies, we started companies, and I've done that now for 40-some years, and I've learned so much and made plenty of mistakes.

Yes.

And mistakes have been my best teachers, even better than professors. I learned so much from my mistakes. And I learned a lot because I made plenty of mistakes, but that's okay because those are your best teachers. And we've been successful at what we've done, investing in building companies continuously, luckily, although I made mistakes and lost money on some. But I've learned so much.

Yeah.

And I learned that a lot of life and the way it works is the opposite. of what we were taught.

Hmm.

And that you succeed by many— doing many things the opposite of what we were taught. In other words, for instance, great entrepreneurs— take Elon Musk or any of the well-known entrepreneurs today— great entrepreneurs don't work on improving their weaknesses. Guess what they do? They improve their strengths. And they work on their strengths. They don't care about their weaknesses. If you see great entrepreneurs, whether it's Jeff Bezos or Bill Gates or Elon Musk, they're just enthused about what they're doing and pursuing their strengths. They also, I've learned, ask a lot of questions like, what if? What if this is the case? What if that is the case? What if it's different than this? They're always trying to innovate. So I'll stop there for a minute and see if you have any questions or directions you'd like me to go.

No, wonderful, wonderful. I thought, hey, you know, he's already giving advice to all the young adults out there that are trying to figure out life decisions and life choices. And so in his book, he has so much more detail, right? Because we can only share so much within the time we have. Especially there is a chapter here, chapter 12, on how to rate your manager. He breaks it down one bit, one bit on pretty much everything. But let's see if we can get more specific, Bryan. Imagine I am an 11th grader in high school right now. Life is challenging. Everything is moving. When COVID came, a lot of people had to change the dynamics of their house and how it all worked out. What would your advice be to an 11th grader in terms of life advice and then how he or she can see himself or herself going into higher education?

For a high school student, a junior in high school, I would recommend the following: figure out what you're passionate about. You may want— what you want to study in the future, and really learn that well. Certain things come easily to everybody, and certain things are tough. Figure out what comes easily to you and what you're passionate about and then pursue that. Many of you will decide, I want to go to college, and then you got to decide where to go. But pursue that which comes easy to you and what you're passionate about in college. And if you don't want to go to college, maybe go to trade school, learn to be an electrician, There's so much need for people that know how to do things in America and in fact in the world that— but get— learn a trade or go to college and do well there, and you'll have a great career. Without a college degree, your options are more limited, and that's a good reason to go. And also, you don't know where life is going to take you. And if you've gone to college and studied and learned a lot, wherever life takes you, you're going to have some knowledge, background, capabilities that'll really be valuable to you. So when in doubt, I go to college. I wasn't sure what I was going to do, but I went and just gradually figured it out.

And you went for about 2 years, and then you went to work as a conveyor belt technician, something like that, right? And you're like, I'm going to go back.

Yeah, I— yes, I stopped college because I wasn't getting the grades I want. Got a job. I remember one day I got called up to a big company. Their line, their conveyor belt was broken.

Yeah.

And I had to go fix it, but I'd never fixed this type before, and so I didn't know what to do. So I, I had the instructions, but I couldn't read them because there was a gentleman there with me from Weyerhaeuser saying, get this done. Put the instructions in my toolbox and put it on a bench a little ways away. And every 3 minutes, I'd go get another tool and read the next instruction.

Yeah.

So it went back and forth. Eventually, I cooked it. And thank goodness it worked. I was so happy to get out of there with their conveyor belt working.

Good Jesus. Yes, I remember that story in the book when you said, yeah, this is my way of getting it fixed better or something like that, right?

Yeah, I was the only one available that day and I was kind of the kid. Yeah, I had to go make it work.

So that's how it goes.

Life can be fun and unexpected.

Very much so, very much so. I could picture everything that you said in the story Because I myself work in a warehouse and I offloaded trucks at night, putting thousands of boxes on the conveyor belt every day. And I would see the technician guy come and fix it, you know? So I imagine you trying to fix it up and figuring it out because you never fixed this type of conveyor belt.

We both have conveyor belt memories.

Oh, indeed, indeed. Yes. So, and what about now, let's say, you know, I'm an educator who happens to be kind of like maybe career counselor in college. And our college is kind of struggling with retention rates and engagement rates because the students have— now they're adult students, so they have more struggles, maybe even financial struggles. How do I keep them engaged and retained so that they can go through that finish line, would you say?

2 things. One is let them know this may be really important to their future, and they're going to live another 70 years after college. Yeah, so That really counts. They want to invest in that, even though it's a little painful now sometimes. Secondly, encourage them to take some different classes, different types of classes. Find out what they really like. They may— I hit upon something, and most people probably can hit upon something that they really like. And so find their joy, seek their happiness in college. And then go forward from there. So I think people— but also, if it's the wrong time for you to go to school, I quit for a year and got a job. If it's not the right time, then quit and work and then come back when it is the right time for you, because you don't want to do anything like that hesitantly or reluctant.

True. And, and you were still— and you, and you were And you were accepted into— what was it, a double major Harvard master program, something like that?

Yes, I went— I got admitted to the law school and the business school, get an MBA at Harvard. So I was a very lucky guy.

Yeah, most people wouldn't think of that as an option after quitting college for— after 2 years, right? Wouldn't even cross their mind. But, uh, you, you definitely saw the world much, much different. In, in your book Be a Winner, which those of you watching the videos are seeing that I have the book in my hands right now because he sent me a copy. You talked about the victim's mentality, right? And oftentimes, many people feel like, you know what? I didn't grow up in a wealthy family. I didn't grow up in the right neighborhood. I don't have the right color. Nobody in my family has made it to college. What would your advice be for them? Because you also didn't grow up in a super successful family.

Right.

And now you've done so well for yourself. Some of your investments have made over 100 times the amount that you invested in. What would your advice be to them that think that way and maybe switch their— to optimism or something like that?

Yeah, my advice would be for them, go for it. The world is waiting for you. And you can be very successful. Think about this, you only live once. It's a gift. And what a gift. You'll only live one lifetime. And why block your success by not going to college? Go to college, go for it, and see what you can become. None of us know. When I was 18 or 19, I had no idea. The only thing I knew I wanted to do was be a major league ballplayer, and I wasn't good enough.

Oh.

So I knew That career wasn't happening. So, but I did go to college and worked hard. I worked part-time even to graduate school. And I do think working while you're going to college keeps your life in balance.

Hmm.

You can prioritize better and not do the silly things that people want you to do or professors want you to do. Just do the important things. Focus and prioritize.

And prioritizing, yes. So some people say it's not about time management, but priority management, right?

Yeah, exactly.

You have had a keen eye to see ideas and analyze companies. In your book, you shared that you discovered 3 times different companies that were pretty much committing fraud. And also in the book, you shared some instances where just by the person how the person looked at you, just a glance, it didn't really give you full eye connection, you realize this is going sour. What would you say are some phenomenal skills that young people should, at least 3, that they should focus on mastering or at least get good at so that they can have a great chance in the business world per se? Because no matter the career, it's a business world out there, right?

Yeah. So Start with number one. What Be a Winner, the book I wrote, means is be a win-winner. Want the other person you're with to win as well, because you can both succeed bigger when you both win. And so try to create what the other person wants and what you want. So win-win solutions, and people will love you if that's your attitude. Secondly, is when you meet people, and Ovi was mentioning this, maintain eye contact with them longer than most people do. I was in a room once where a senior fellow from the other company was coming to visit us, and he— his eye contact was very short. He looked away right away.

Right.

And it struck me that, boy, he either doesn't want to know me well or he's not genuine. Or he's coming here to do something that isn't good for us. And it turned to be the latter. He was offering something that made no sense to us, and we of course said no. But eye contact— smile and keep the eye contact a little longer when you're shaking hands or meeting someone, and they will really like you. And then finally, Be positive. It's very simple. Positivity wins. Positivity makes great things come true. Have a positive attitude and a positive countenance when you meet people. Be happy to get to know them. Those 3 things will serve people very, very well.

Indeed, I cannot doubt it, especially coming from you. So I, I, when I received the book, I began reading it and I was taking so many notes You may be able to see it right here.

I do.

I was like, thank you so much. And then it was taking me so long to get through. But one of the things you mentioned in the book also is that you had, you know, some issues with asthma growing up. And I don't know how it is still present in your life. So what I did is I decided to buy an additional copy because the one that I have, you very kindly gifted it to me. And thank you so much. Bought the copy, gave it to our 16-year-old that we have in our home. because she also has had some problems with that. And I said, you know, and not only would you connect with his story very much, but the wealth of knowledge— I mean, it's a whole college degree in a book. And, uh, I appreciate that you sharing your, your wisdom very much, uh, Bryan, especially today, our time, uh, together.

Yeah, thank you so much.

Where can people find you, Bryan? Go ahead.

One thing you could share with your daughter too is when I was young, my asthma was severe. And I missed a lot of school and etc., but it made me love— when I could breathe well and go outside and play with the other kids, I loved it. And I think I still love life extra when I'm healthy. I still have some breathing problems, but got a little healthier over the years. And it makes me appreciate life, appreciate every day, every hour. And especially the opportunity to speak with you. This is wonderful for me, and I really, really enjoy getting to know you.

Likewise, Bryan, likewise. I'm a farm boy from the sugarcane fields of Guatemala, you know. That's where I grew up, in the sugarcane fields.

Beautiful country.

Beautiful country, yes. Yeah, the funny thing that I find is that most people know Guatemala more than I know Guatemala. I was so poor, I never got to go anywhere. So yeah, that's like, oh, Ovi, did you know this place? Yeah, no, in the books, yes. But, uh, that's how it was.

You want me to mention why I wrote the book?

I would love to know, yes. Yeah, well, well, I, I know in some of your videos you shared that it was for your daughters, but maybe, you know, there's even more detail to that reason.

Well, I wrote it for younger people like your audience. And you. I want young people to know how to succeed much earlier than I did. I had to learn these 50 or 100 things, and many of them are backwards from what I was taught. And so, I go through and talk about what's backwards, and I have some videos on that. But I want the book to be the book I wish I had when I graduated from school. That would tell me how to invest, how to work with other people, how to build successful teams, how to build companies, how to interact, how to be positive, and how to create success. I wanted to share that with younger people like the audience that you have, because they can— if they read the book and implement some of it, including the same things I mentioned, already, they can go forward and be far more successful. And it's fun being engaged with other people. Part of a winning team is really, really fun, and they can have a lot of fun and succeed. That's why I wrote it.

I, I mean, when, when, when I was going through the book, because I went through it I read about a third of it. I did not read the whole book. I've never been a big reader, so I can't seem to get into the habit. So what I did is I bought it on Audible and listened to it twice. And then I watched all your videos, maybe 3 times, all of them, like a marathon.

What?

So I watched it the very first time that I came across you, and then the second time I was on a flight to Chicago. And then yesterday I was watching all of them again, and I was thinking, when I was in high school, I was a senior and I was in ESL shelter classes. These are classes for English learners that almost are good with English, but not quite there yet. So they had a book called Where Is Cassie? And I think, man, if they could only replace that book with this book, holy cannoli. Because you even talk about investing, you know, how can you choose Internally instead of being a day trader and things like that. And this comes from you who have made millions and millions and millions, not only for yourself but for many other people as well. Yeah, I cannot thank you enough.

We invest people's money that are pension funds— state of Illinois, California pension funds— so the pensioners benefit because we have been fortunate to do very, very well for them. And we keep doing it. And that's quite a motivator to think of teachers and police, firefighters that you— who are retired now and you're working on their behalf.

Yeah, that is true. One last thing I'd like to say that I found so much interesting was that the driving test, when people fail your driving test, right? How do you go about that? Because My thinking process was, wait a minute, what if the CEO was driving so cautiously because he had you as a guest in his car? You know, that was what I was thinking. But please share some more.

Yeah. No, I've learned that great CEOs and entrepreneurs drive quickly. They switch lanes because they're impatient. If they're impatient, it helps their chances of succeeding. And so, I look for that. People that drive slowly and cautiously may be suitable for other specialized jobs, like being an accountant or something like that, but nothing where you need to be aggressive. My wife is a surgeon and she drives carefully.

Yeah.

But surgeons have to be ultra careful and detailed about every step. when they're opening people up and sowing and things. And so that's appropriate. But for entrepreneurs and CEOs and executives, they should drive a little faster. That was—

I was like, hmm, this is interesting. Thank you so much for sharing that. Let's see here. Once again, for those watching the videos, this is the book, Be a Winner. Find it in most all bookstores you can find. His website is also bryancressey.com. We'll also add it on the description. Bryan, any last words you'd like to share with our audience today? Because this, after it's recorded and edited and send it out, we're gonna purposely send it out via email to all the colleges in our email list because I go everywhere, you know.

That's wonderful. Yeah, my final advice is have a wonderful life. You can do that and go forward with enthusiasm. Recognize this is your chance. When you were 15 to 25 years old, you set yourself on the pathway to your future self and future success. So go for it. You can have fun then and succeed and have a great time with your family too. So do all those things. You won't regret it.

Will not. Thank you everyone for listening, and keep this in mind: you don't have to learn only from me. You have Bryan here and everyone else that you'll be listening to. Choose who you can learn from, but at the end, make your own decision. Would you agree, Bryan?

Totally. You are the only one that can decide for yourself.

All right, all right. Thank you, thank you, thank you. Thank you for being part of our community. Who is a leader you believe should be interviewed in our podcast? We would love to hear your thoughts about it and interviewing the leaders that you admire most. See you on our next episode.