Nov. 19, 2025
Put to the Test: Rising Above Adversity with Derrick Girard
This week, we dive into a candid conversation with Derrick Girard, former financial advisor turned tech entrepreneur, author of Put to the Test, and speaker.
He shares his powerful journey navigating lawsuits, scaling a business, and embracing a “Figure It Out” mindset.
Derrick discusses how:
- Personal responsibility and relentless problem-solving fuel entrepreneurial success
- Facing three lawsuits simultaneously became a catalyst for growth and resilience
- Building solutions by deeply understanding customer pain points differentiates you in the market
- Instant responsiveness and rapid iteration empower business agility and client trust
- Leaders must prioritize asking meaningful questions and truly listening to their teams
- The path to leadership involves continuous learning, humility, and embracing discomfort
- Effective entrepreneurs focus on solving problems, not just chasing the title of entrepreneur
Resources Mentioned:
- Put to the Test: When Life Demands More, Will You Make Excuses or Figure It Out? - https://www.amazon.com/Put-Test-demands-excuses-figure/dp/196619059X
- Website and contact: https://derrickgirard.com
WEBVTT
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This podcast is a proud member of the Teach Better
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More at Teechbetter dot com slash podcast.
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I don't care what the problem is. We have to
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find a solution one way or the other. I was
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the user of the product. Again, I solved the problem
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that I solve for myself. Whatever it is you're dealing with,
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an excuse doesn't solve the problem. The problem still exists.
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We have to solve the problem.
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Do you want to be a leader in a constantly
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changing world? Our emerging leaders look different, come from various
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backgrounds and from all different age groups. Leadership is changing
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and it's hard to keep up. But the good news
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you can be a leader too. You can be an
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e merging leader. Welcome to the Limitless Leadership louanch A
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try generational conversation for emerging leaders.
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Come spend some.
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Time with us to discuss leadership from three angles. The coach,
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Jim Johnson, the Professor, Numah Kareem, the host, John Gering,
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a monthly guest, and you get in on the conversation
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on Apple podcasts, Spotify and Speaker. So come on in
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and make yourself comfortable.
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Our debt today is unscripted. He's loose and he's a
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lot of fun. We're excited to welcome in Derek Gerard
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on the Limitless Leadership Lounge. I'm John Gerring. Joint is
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Always by doctor Numa Kareem, Coach Jim Johnson, and today's
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conversation we know will benefit you as a young and
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emerging leader. Whether you're a leader of a business, an organization,
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maybe a leader in the educational world, or just a
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leader in your community or in your family. This is
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for you. So Coach, go ahead and introduce Derek. Let's
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dive in today. Yeah.
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Absolutely.
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I got a chance to get connected through one of
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our connections, and I get a chance to talk to Derek,
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and he's got some fascinating stories. I know he's going
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to be able to share with us. So let me
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just give you a little bit of background. Derek Gerard
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is a former finance advisor turned tech entrepreneur. He founded
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the my rep chat to solve a real problem in
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the industry, skilled it with all the sales team, and
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landed major financial firms nationwide. Despite facing three lawsuits at once, which.
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I'm sure we're going to delve a little bit into.
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From an investor, a competitor, even a family member. He
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fought through and won and ultimately sold the company in
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twenty twenty three. Now he helps others embrace what he
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calls the FIO to figure it out, mindset to the
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key to navigating obstacles and building something to the last.
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And he also is a speaker, and he's the author
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of put to the Test. When life demands more, will
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you make excuses or figure it out without further ado
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Derek Gerard, Welcome to the Limitless Leadership Lounge.
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Thank you for having me that. It was a great introduction.
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I appreciate that.
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Yeah, absolutely, I got to ask you. I did get
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a chance to talk to you, but we got to
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share this to the audience. So tell us a little
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bit about your journey from financial advisor to being a
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tech entrepreneur and that certainly we've got to add a
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little spice to it with maybe a little bit about
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the lawsuits.
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Yeah, yeah, it was. It certainly wasn't planned. It certainly
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wasn't intentional. I never had any desires to do that.
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It was accidental. So I found myself in this unique position.
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I worked generally with retired people and people that are
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hearing retirement, and I found myself in this position where
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my clients kept texting me. And back then in twenty sixteen,
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this would have been it was against the rules, against
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the regulations to communicate through texts. You weren't allowed to
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do it, and so all the different requirements in order
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to have written communications couldn't be met through a text
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message at that point. And so I went to my
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compliance officer and said, hey, there's got to be a
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solution to this problem. What do I do? When my
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compliance officer said, there isn't, so you just cannot do it.
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So I told my clients I can't text, it's against
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the rules. Don't communicate through text with me. We have
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to use email or phone call. And what I learned
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was that my clients didn't really care. This is how
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they chose to communicate, so they just kept texting. And
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so figure it out to me is it's one of
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those things that I think a lot of people say
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that sometimes when it means not my problem, Like when
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you hear that word use or that phrase us, or
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like you figure it out what that means is not
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my problem. To me, I felt like, this is my problem.
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I have to solve this otherwise I'm going to break
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all these rules and get in trouble. And so I
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just started on this journey of asking questions. I just
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wanted to know how to solve this problem. What was
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the regulations, what was the problem, what was the challenges,
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what was getting in the way. And that ultimately led
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me to my uncle, who was a computer programmer, and
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I said, Hey, this is what I want to build.
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If I tell you what to build, can you build it?
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And he said, yes, I can do that, and we
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were just off to the races from that point on.
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And then I started showing it and sharing it with
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other people because I knew the industry was looking for it.
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And when I started showing it and sharing it with
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everybody else, I realized, Holy cow, this isn't a solution
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just for me. This is a solution everybody wants. And
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that's one from this really cool idea to something much bigger.
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And that's where I ended up as the founder of
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a tech company.
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And I think I resonate with you on figuring it out,
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because everybody tells me that I am crazy, like leaving
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my full time job and then starting my own nonprofit.
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Then I'm planning for another startup company, and I was like,
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I will figure it out. Everybody keep telling me you
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don't have the experience in the business world. I will
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figure it out. And there are so many tools. But
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one thing I have realized that crisis and chaos gives
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opportunity to learn and grow. So I have learned so
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much from I started a school and there was like
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this lady who took control of my school. Then I
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have a lawsuit and all those kinds of things, and
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now I'm learning what to do and what not to do.
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So from your point of view, how do you see,
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how did the crisis help you to grow? What are
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some is that you learn from these crisis.
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It's the biggest crisis obviously, was the lawsuits. Feeling like
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we were hitting this point where I knew the trajectory
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of the company. I knew it was going to take
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a little bit of time. The financial services industry is
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very slow to adapt new things, and so I knew
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I had to get the name out there. I knew
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I had to get the solution out there. But I
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also knew it was going to take time, and the
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pendulum started swinging. Were not only were we landing real
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substantial clients, we were landing the biggest fish in the pond,
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like the big ones were coming to us. And it
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was right at that point when everything went sideways. And
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so for me, it was a test ultimately of can
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I actually do what I preach and can I do
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what I believe firmly in my heart. But the also
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the other thing was, and I said this to my
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son the other day, it was an opportunity for me
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to prove how much I enjoyed learning, which is weird, right.
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I wasn't the greatest students in high school. My son's
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in high school. And he said to me the other day, Dad,
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I feel like now I'm actually enjoying learning. And he
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said it like this was an epiphany. And I said,
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I'm glad you figured that out in high school. I
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didn't figure that out till college, right, that I actually
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enjoyed learning. And so that crisis, that chaos, it was
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just this moment of I can either step up and
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do what I believe is right and learn and educate myself,
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or I can just shut down. And I think a
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lot of people do because that scares them and they
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don't know what to do, so they crawl back into
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what feels comfortable. And so for me that was, like
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I say to everybody else, when these lawsuits hit, I
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became a law student. And it sounds crazy, but I
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just paid three different lawsuits in three different areas. All
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I did, on top of running the business, I barely slept.
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All I did was just study the law. I had
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to know everything that was going on, so I wasn't
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just being surprised day in and day out.
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Yeah, he became a student of it. And that's what
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we all have to do in leadership. Now, going back
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further a little bit, because some call you an accidental entrepreneur.
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You found a problem and you solved it. But I
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would argue that there has to be mindsets and processes
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in place that you had before you came across this
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problem and became an entrepreneur. Is there even such a
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thing as an accidental entrepreneur? What mindsets did you establish
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throughout your career before finding a solution to that problem.
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So many things you just said there that I'm so
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excited to touch on. The First thing is I love
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speaking on college campuses and getting in front of students,
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and I love getting in front of entrepreneurial students and
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students because there's now degrees, there's majors for entrepreneurship, which
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I think is really interesting. What I've found in my
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experience is that most entrepreneurs don't start off and don't
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set out to be an entrepreneur. Most of them are
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just problem solvers. And so it's in my experience I've
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met students before that have said, look, we want to
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be an entrepreneur. We're going to start a company to
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do this, and I go, great, walk me through why that?
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And they go, we don't know what's the market for it.
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We're hoping to figure it out. What's the need? I
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don't know, So in their mind like, we're going to
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be an entrepreneur, and then we work our way back
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to the problem. And I think most really great entrepreneurs
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and products and success story start with the problem and
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then you become the entrepreneur, right and you just find
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yourself fitting in that bucket. And so I never really
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had this idea that I'm going to be an entrepreneur.
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Previous in my career, I was given the opportunity to
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run my own firm and step out and be that
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entrepreneur and I failed. And I talk about this in
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the book. Perspective is massive, right, It's so important to
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have that perspective to know what I did wrong, so
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I know how to get it right. And I think
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a lot of people that crushes them as well. So
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it wasn't that I was an accidental entrepreneur. I never
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saw myself going into the tech space, but I always
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saw myself and I have been my entire life a
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problem solver. So when there's a problem, I firmly believe
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excuses don't solve problems, so I don't care what the
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problem is. We have to find a solution one way
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or the other. And in this case, it just led
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me to being the creator of a problem in a
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company that solved the problem.
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Very cool, Derek, you said you like to speak to
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college students, so let's delve into it because obviously with
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the Limitless Leadership Lounge and we want to help young
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in emergent leaders can use the zero down to if
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you were helping young college students, and not necessarily all
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college students are young, but most of them are. Is
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that what advice would you give them on how to
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be a more effective leader.
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The biggest thing that I say all the time is listen,
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ask questions, and listen all of your I firmly believe
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this in life and in business and in leadership. All
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of your answers are in your questions, not your statements.
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And so many people, especially young people, who in my experience,
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again I was the same way, So I'm not blasting
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somebody else. I was the same way. I think young
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people that get to a position of authority or management
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or leadership, they think the title means something, and the
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reality is that the title doesn't. It's how you behave,
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it's how you interact, it's how you ask questions. The
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greatest leaders in the world don't have the answers, but
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they know how to engage the audience and ask the
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right questions and empower people. And so I think, especially
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when people are young, they get real sort of power
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hungry and title hungry, and they realize it really doesn't
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make you a good leader. In fact, it can do
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the opposite really fast. Again, I learned that the hard way, right.
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I came out of the military and went into leadership
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in the civilian world, and I had to learn in
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real time that military style leadership doesn't work in the
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civilian world. Right, So all these different lessons you learn
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as you grow and you develop. That was really important
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