What in the world inspired you to create a dating coaching business? Like what inspired
you to just say, you know what, I want to go out here and fight for other guys that were, I guess,
potentially like me. I don't know the story. But I think we would love to know more about you,
your dating life and what just really inspired you to do this. I think for me, and it's not just with
dating. It's a lot of things. It's like in life, when I figure something out I have this urge,
I guess we could say, or even desire to teach and help someone through it. And I'm not saying look
at me I'm Mother Teresa here, I'm Gandhi. Really it's more venting. It's selfish. I just enjoy it.
I enjoy when I figured something out and I'm like, you know that feeling when you figure something.
It can be anything. You're a videographer, well you're a lot of things; producer,
director, musician. Don't do this, stop. This is not about me. We're just talking about you. I'm
just saying. When you solve something, when something clicks, the click, there's a high.
It's like wait, I figured something out. Come see this. I've got to tell someone about this. Like
recently for me, I mean it's always dating because that's my business and that's what I do. And
I'm learning new things over the past 10 years of doing Tripp Advice. I've learned new things about
business, marketing, digital marketing, sales, and just all the above, like everything. And so I've
had so many different clicks over the years and still clicks about dating site. But just recently,
I'll have clicks on things with business and a couple of weeks ago, my friend said, hey,
you know a lot about digital marketing. I want to I want to start something.
Can I come over and you can just give me some advice? And it's like music to my ears. Let's go.
I love giving advice, thoughts, having conversations about stuff that I feel I
know well. I wonder if all people are like that. I don't know. I wouldn't imagine they would be,
it's not a very unique trait. I think it's a time consuming trait. And what I mean by that is if you
are a natural teacher, you have these moments where you just take time out of your day to do
it. No real reason why, it's just I know this, you want to know this, of course I'm gonna show you.
It's just a natural knack for helping and being resourceful. But you hadn't gotten what I want you
to get. Like, I get that you want to help people. But tell me about the linkage between dating.
Yeah, so we're getting there. So... I'm impatient Tripp, as you can see. I had to explain that
desire that's in there, because that's what made everything click. Yeah. Okay. So when I was 20...
I mean we can go real far back, but we'll just keep it somewhat recent. When I was 22-23
I was forced to learn how to get better with women. I say forced, because I didn't have
a choice. Yeah. One, like many men, I had the desire to be good at women, to want to be with
attractive women. But two, I was in a situation far outside my comfort zone because I came from,
so what happened was I was in Illinois my whole life up until 22 years old and I traveled to Los
Angeles to start a career in film. Did you know that, did I tell you this before? Yeah. I had to
look but I'm just listening. Yeah, so I wanted to be a producer. I want to be a movie producer
and as I'm in California, and I just left all my friends and family, but mainly for this story,
friends with groups of people where you can easily meet women because you have an ingrained social
circle. Yeah. Now in LA where one of the hardest cities to meet people in the world, because of the
way that the whole city is set up. You can go to LA it's one of the biggest cities in the country,
and you feel it's post apocalyptic because everyone's in their cars and you don't really
see people. Anyway, now we're in LA, really hard to meet people. I am terrified, beyond terrified
to go up to a woman and start a conversation, especially one I found myself attracted to.
And so I was at this point where the desire was strong, it's like a big disconnect. You have a
strong desire, but you need to build this bridge to get there. Yeah. So I had to figure out how to
build this bridge, while being super shy and not really good with women having no idea or having a
clear understanding of what women were attracted to. I thought I did. But I was wrong. Okay, so...
unless you have any more questions about this, long story short, I solved it, I figured it out.
And we're back to what I was saying earlier, the clicks.
It's like I get how to do this. And also, it was not just the clicks, but it was all the stuff that
I learned when I was learning from other coaches at the time and in the pickup artist scene at the
time and the books that were out. Things were, it was just not simple. Nothing was simple.
It was a lot of unnecessary work. Of course, it should take work. But there's a lot of unnecessary
work in order to get results in data. Absolutely. So I, this is where I will say I pat myself on
the back for, here's where my ego comes out. Here we go. I think I am really good at explaining to
people and dumbing down things to a degree where someone can understand it. Got it.
At this point in my life, I'm obviously, I'm the best at doing that in the category of women.
Business, that probably comes in second. Like I can definitely explain business,
but I still have so much more to learn there. But with women and dating,
I've been doing it for so long that it's even more second nature. But at that time,
I really felt I can explain this to a guy in the simplest terms and he can get quick results.
And obviously, that's happened. Well, the story goes, it was a rainy Los Angeles evening.
And I had drinks with a guy who I met through, I don't know, another friend, I actually forgot how.
But I met this guy for drinks because at this time, this is pre Tripp becoming a dating coach,
but post learning it. So like I learned it, I started a podcast with a friend for fun just
giving dating advice. We called it Dudes Talking About Chicks. It was not to make a living or
business or anything. Meanwhile, I'm over being a movie producer. I did not like the industry
anymore. It's a really terrible industry. I still believe it to this day. It's just
brutal. This is pre me too, by the way. So that made it even worse. But I wanted to get in the
movie industry and I got drinks with this guy to network to learn more about the industry himself
from him. So we get drinks, we're talking about the music, whatever, I have no memory of this at
all. But the memory I have was what happened at the end of the conversation right before I was
about to walk back to my car to go home. He goes, so what else do you do? Do you have any hobbies,
do you do anything else interesting? And I said, yeah I have a podcast. Oh cool,
what's the podcast about? I give dating advice to guys. And he goes, interesting.
Do you mind if I ask you for some advice? I was like, yeah, for sure.
He asked me a question. Whatever it is, I think it was like a friend zone question.
And I just vomited out, just like ok... blah blah this is what you gotta do. This is what
happens. This is how it's supposed to work. Blah, blah, blah. And he was kind of like a deer
in headlights afterwards. He was like damn that was pretty good advice. I was like, thanks man.
I was like, alright man. Nice to meet you. Take it easy. I leave the bar, I walk outside. There's
a light drizzle. You could see the light drizzle in the headlights that were coming
towards me in the street as I crossed it. And I'm walking on the sidewalk. Halfway to my car, and
a non literal lightning bolt hit my head. It just hit me out of nowhere. I was like, this is what I
have to do. This is it, not music, not movies. At this time I was doing this podcast with my buddy,
I was so passionate about it. I loved it, it was so much fun. I loved creating media,
obviously, I wanted to be a movie producer, so I enjoyed creating media. And I really
enjoyed talking about social dynamics, female male dynamics, relationships,
mating, all that stuff. So it's like this is it. This is what I got to do. So my girlfriend at the
time was a graphic designer. I get in my car in my Honda 1997 Honda Civic. I mean classic.
Stick shift. Oh, very classic. Five speed, just saying. You could do some things with
that. You can do some things with it. EAM intake which gives it this nice airy sounds
when you hit the clutch and switch gears. Anyway, I get in my car, I call my girlfriend
who was an entrepreneur herself, because she was a graphic designer and I said,
what would you think if I became a dating coach? Not for permission,
but I wanted to get her opinion. What do you think of this? This is a person to business person.
I gotta give it to her. We are not together anymore. But
she immediately without hesitation said I love this idea. I'll build a website.
Which by the way, in 2000, this is not 2010. If you wanted to build a website in 2010,
first of all, do you remember how much it costs? Wix wasn't really around. No Wix wasn't around.
There was no Squarespace. WordPress just kind of started being used and built. Yes, but you had a
needed to have a developer. You needed someone to code it so it was thousands of dollars. My
girlfriend at the time would charge minimum five grand to build a nice but simple website.
And so I was like, wow, this is amazing. By the way, this is when websites were a thing. Whole
tangent here we don't want to go into, have you realized that websites just don't really
matter anymore. A lot of my work, I mean some high profile work I've gotten I would think I
was required to have a website. They mainly want your social media. Exactly. So crazy. Nowadays,
you don't need a website. At all. You needed a website in 2010. For sure, that was the only
way for people to find you. Until like 2017, right. Anyway, got lucky there. Because the
nicer your website, the more people are going to. You look more reputable. Yeah, take you seriously.
So over the next year, as I kind of figured out how am I going to market this,
how am I going to get clients? How am I going to make this something I can just do?
And what was cool was it was so organic. It didn't come from wanting to be super wealthy or like, oh,
I felt like... you know, do I consider myself an entrepreneur? Kind of, but I don't know if
I'm an entrepreneur. I started a business. To me an entrepreneur is someone who's starting
multiple businesses. And they have multiple streams of income like real estate. Yeah,
like what makes money right? That's not why I started it. You were passionate about it. So
passionate about it. I was like, if I can just make a living off of this. I can feed myself
and just buy the things that I need, I will be happy.
So where would you like, any questions so far? We can keep going. But that was the inception.