What It Takes To Rebuild Your Life with Griff O’Brien

Josh Felgoise (00:00.204)

Welcome to Guy's Set, a guy's guide to what should be talked about. I'm Josh, I'm 24 years old, and I'm here to find all the tips, advice, and recommendations for everything you're wondering about. Let's get into it.

Josh Felgoise (00:17.634)

Welcome back to guys set a guy's guide to what should be talked about. If we haven't met before, my name is Josh. I'm 24 years old and every Tuesday I come on here and try to find the best tips, advice and recommendations and have conversations that should be talked about for guys in their twenties. This week I have Griff O'Brien on the podcast.

He is the CEO and co-founder of a company called Estate Media alongside Josh Flagg, who you may have heard of from a show called Million Dollar Listing. I met Griff through my real job a few weeks ago and found his story to be incredibly fascinating. From starting his first company in college to taking a year off from college after junior year to get the help he needed, to now building and founding a real estate media company.

I think one of the coolest and probably my favorite part about having this podcast is that I have a medium to have a conversation with somebody who I find to be really cool and has a story that should be shared with the world and should be heard by a lot of people that may not have been heard from had it not been through this podcast or I don't think I would have ever known or known his full story and all the amazing advice he had to share if it hadn't been for this conversation and seeing somebody who's so successful now at age 29 who fought a really hard battle.

around his twenties and came out on the other side so much better and so much better for it is just really cool to hear and really inspiring to hear. And he really talks about that experience in such depth in this podcast. And I have such admiration for that level of bravery to share something that really is so stigmatized and has such a taboo around it that guys don't really talk about in general.

And being able to share that to anybody is just really incredible. So I'm grateful that we had that conversation on here and it's just an amazing resource to have for anybody. So thank you, Griff, so much for doing that and having this conversation with me. And I think somebody will be really inspired by you. So that's to you specifically, if you ever listen back to this, I don't know if you ever will, but if you do anyway, Griff also talks about all the lessons he's learned from starting his own company.

Josh Felgoise (02:15.136)

He talks about previous managers he's worked with and the way he now wants to manage the company moving forward because of the experiences he's had. He gives advice on confidence. He gives advice on networking and mentorship and finding mentors. It's just a really great conversation overall. And there's just so much advice in here and so much knowledge he dropped. And I'm really thrilled to put this one out. So without further ado, please welcome Griff O'Brien to GuySight.

Josh Felgoise (02:45.838)

All right, Griff O'Brien, welcome to Guy's Head. Thank you for having me, Josh. I'm looking forward to this. It should be really fun. We met a few weeks ago from my real job, and I was really fascinated by your story and where you started and where you are now and how much you've done in 10 years. Is that right? I guess so, yeah. Around 10. I'm 29, so roughly. Yeah, roughly.

roughly 10 years. It's a pretty impressive feat what you've done. You're now a co-founder and CEO of a company. We'll get into all of that. But I want to start with your kind of first venture, your first company or like way into entrepreneurship in college. Because I think your story and how you started is really fascinating. So let's let's start there. Share a little bit about who you are and what that was. Yeah, I started my first company sophomore or into junior year of college and

Quick background, I'm from Colorado. I grew up in a household where my dad was in the cable satellite television business. So was always familiar with TV, right? Like I watched TV as a kid and always was interested in the business behind it. I went to college in North Carolina at Wake Forest University, which is not a place where people go that necessarily wanna be in entertainment or media, but I wanted to kind of move away, right? Check out something new and really love this school.

But I did pursue internships in media and entertainment. Something that I was very fortunate to have was mentors early in my career, right, who said, hey, if you want to differentiate yourself and get ahead early, get subject matter expertise. And so right out of high school, right, my first summer out of college, I interned at STARS, which is a premium cable channel, similar to HBO, but smaller in scale, and got an internship there right out of college.

And so I did that my freshman summer. went back my sophomore summer and always knew that for me, being young and not having the experience or, you know, obviously understanding the industry as many people that were senior than I did. What I did know is like the pulse of young people, right? And how young people were consuming content. And that's a thread throughout my career, right? Of like, how do you stand out?

Josh Felgoise (05:02.67)

in environments where you have tenured executives. It's like, bring what you have. And at that point in time, it was, hey, people my age are not watching cable television, right? This is how they're consuming content. Many of them are actually using their parents' passwords, right, until they have buying power out of college. And what I found when I was at Stars, and this was right around the time that streaming was starting. And so Netflix had predated my time there, 2014, 2015, by a few years.

Sling TV was the first like virtual cable company that had launched. And Stars also had what they call an over the top service, right? You can pay on the cart, you can watch it on your phone, you can watch on your television, you can watch on your computer. What I found at that time was all these streaming services were launching, right? But people didn't understand them. from my age to my parents, they didn't know like how they could actually leave their cable subscription that they were paying $140 a month for.

Yeah. Right. And maybe watched three channels and the cable television bundle, right, is one of the best business models ever created. Right. You're paying for maybe three to five percent. Those cable channels are getting affiliate fees are getting paid by the cable and satellite companies, whether or not someone watches it. And so what I wanted to create and at the time when I came up with this idea, I didn't know if it was possible was, hey, go somewhere, right, log in and say, here's what I watch.

right from an app, like a program level that I watch the sports team, right? I want to watch this series. I like this type of programming. What are your internet considerations and how much do you want to pay? And essentially we would be able to have on the backend, right? Someone of a decision tree where if they said, I want to watch game of Thrones. I also like watching my local NBA team, but I want to watch national NFL games. I like, you know, new girl. Where can I find that?

we would be able to feed them a bundle of services, right? That essentially said, here's what you can get at the cheapest possible price to watch everything that you want to watch. And so that was the idea, right? Of basically create this recommendation system. And so what I did is I worked, have much money. With my intern money, I did get it $10 an hour. I found two developers on Upwork. They were based in India and we built the backend of what that could look like.

Josh Felgoise (07:27.63)

I then used my relationships from my internship to get affiliate deals with stars, HBO, and also sling TV. Right? So when someone came in, we recommended that they use sling TV. They subscribe. We get a percentage right of that revenue. Took that and was like, Hey, this is really hard. I was at school at the time. and ended up getting a strategic partner again, through someone at stars to basically come in and invest in the company and help build it. Cause there was only so much I could do.

right from a development perspective to build the product. And so that was like my first journey into entrepreneurship, right? Of like- And how old were you then? So I was 20 at that time. And you know, it was, hey, I have this idea, like, let's go and try to build an MVP, right? Or something that we could take and try to get some strategic investment. At the time when I look back, right, comparing it to my company now, I knew nothing right about business. I didn't really know like how this would scale, how much money it would take to build.

how much money we could actually make, right? And so I look back and I was certainly naive and I think that's what allowed me to do it, right? As a kid, like in college, but the outcome, right? Well, I was able to exit that company, it was not huge, right? And part of the reason is I didn't know how to scale it. I didn't know how to value it. I did not have the people in my network or reach out to people that could actually help me with this thing as much as I should have. And so it was a great learning experience and I have no regrets, right? For how it ended.

Again, I think it was an early win, albeit small, that gave me the confidence right later on down the line that, you can build something, right? You can start something even if it's bold, right? And people don't believe in it. And there is an outcome there that can be achieved. So what drove you during the time that like you that people didn't believe in you or like you may not have had all the confidence? Like where did you find the drive to keep going and build it when you were kind of on your own doing this and at college at the same time, which is wild?

Yeah, it's a really good question. I think some of it was innate, right? Of, I've always had just this drive and desire to succeed, right? And sometimes that is to my detriment, but also has been, I think, a key part of my relative success right in my career is like, I want to prove to myself, right, that I can do difficult things. And I've always done that. I think the other part of it was

Josh Felgoise (09:51.19)

I was very strategic in college thinking a lot about what kind of jobs I could get out of college. And I knew, right, that I went to a good school, but it wasn't an Ivy League, right, or was not like a top 10 or 15 school. Like, hey, this is something too, even if it's not successful, that shows that I'm thinking about this industry in the right way. Right, I'm doing something that hasn't been done and I'm trying at least to build something. And I knew that doing that, right, anyone reads your resume and that's the first point, like it's interesting.

Right, people want to learn about it and sometimes you need something like that, especially out of college, right? Just get an interview. And so for me, it was both a test, right, of can I do this? Right, and I thought it was a real need based on who I talked to and the limited knowledge I had in the business. Also, I knew that it would be highly strategic, right, when I went to actually get a full-time job. Yeah, that's really smart, especially the part about like, it's always a conversation topic. It's still a conversation topic to this day. Like, we're still talking about it.

I like what you said a lot about like differentiating yourself and standing out. What advice could you give to somebody that may be my age a little bit younger, even at that 20 year old mark that is looking to stand out or maybe differentiate themselves and doesn't really know how, especially in where we're at in terms like the job market right now. What advice do you have for that person? Number a couple of things, right? Number one is get incredible mentors and people around you.

Right? When you are young, people are willing to talk to you. And I think that even, you know, our education system doesn't do a good enough job, but most people are open to talking to a college student. Right? People are always open to talking to a high school student. And most people are open to talking to someone early in their career. Form that relationship and plant the seeds before you're asking for something. Right? And people I think are very open to even now, right? When younger folks reach out to me and truly just want to learn about my background.

It's much easier, right? To say yes. And like, you want to give back. So that would be number one, right? For young people of like network early. And I think just being young, you're going to get access to opportunities. I guess the second part of that would don't be discouraged, right? Like I was on LinkedIn, all of college messaging people and most people do not respond, right? But it really takes one person to then like buy in and say, Hey, I want to help this person or share knowledge. And they introduce you to others.

Josh Felgoise (12:14.38)

So find someone that's in the industry you want to get into. Number two, I would say, as I mentioned a bit earlier, is find what value you can provide, especially to executives at a company, and make them look smart. The more you can make the person you're working for or want to work for smart and fill it a knowledge gap, the more successful you're going to be. And number three, which I did not find until I started my business now, is take whatever expertise you have.

So let's say you spend the first three years of your career in media or content as I did. Find an industry with people that in title and perhaps in income level are high above you, but have a complete knowledge gap in terms of what you know. And if you can transfer knowledge between industries, you have a leg up. Everyone in the content space in LA knows a lot, and they think they know a lot.

But the moment I took my understanding of social and digital and content monetization to real estate, right, to an industry that it's not really something, you immediately stand out, right, and differentiate yourself. And so I think the last thing comes sequentially after the first two, like you have to have some expertise in one category, but I think you can accelerate your career path very quickly by taking that expertise and entering an industry.

where other people are not looking at it the way you are, right? Just by nature of you having that even few years of experience. Yeah, that's strong advice. Are you still in touch or like close with the mentors that were there for you at that time or advising you and, and how did you determine like who to kind of decide or who to, who to pick as your mentor and latch onto? Yeah, I would say the majority of them. Yes. Right. There are people from stars and then my third internship was at Turner broadcasting.

which at the time was owned by Wyrm Media and CNN and TVS and TNT. And I still stay in touch with many of those people, right? Naturally, I think some mentors and just professional connections are going to go in and out of your life just as friendships do. But the early people that I did meet, right, that were instrumental then, I'm still in touch with many of them, right? And now some of those relationships have come full circle where I'm in a position to help those people, right? Who helped me when I was 18 and 19 years old.

Josh Felgoise (14:37.038)

The other thing that I did was, look, if you are trying to get a recommendation or an introduction, right, it's only as strong as the person who is facilitating that introduction. Absolutely. And so I look to get a couple of very, very high level mentors, right? People who were at the top of their industry, right? Fortune 500 CEOs. And one of them, a guy named Greg Maffei in my life, he's the CEO of Liberty Media.

They own F1, Charter, Sirius XM. I mean, a ton of companies, right? They owned stars at the time. And I played soccer with his son and just asked him when I was in high school if I could learn about his business, right? And he's on the board of many companies, right? And so just staying in touch, even if it was getting 15 minutes of his time to learn about how he was thinking about this world was incredibly beneficial.

And he's made introductions to folks in his network that otherwise I would not have been able to get access to. And so I think the quality of the mentors, and I'm not saying they all have to be super senior people that run businesses. For me, it was a mix of having people who were maybe a couple of years older than me, folks that were mid in their career, and then people who had really excelled in an industry that I wanted to be in.

And having all three of those levels really helped me paint the picture in my mind, right? Of like where I wanted to be in the next three and five years. And then looking 10, 15, 20, 30 years down the line of what the top people had done really started kind of painting the picture for me. I mean, you're obviously a very confident person, like enough to go up to your friend's dad and say, like, I want to learn about your business. So what maybe do you say to somebody that would love to have the mentors that you've provided for yourself and gone out and found and kept the connection with?

that may not have that level of confidence that you exude in talking to that person. What do you say to that guy? I mean, I would say for me, look, the confidence just comes with repetition. Like it's somewhat of a cliche, but when I first did it, it was incredibly unnatural. And I know people today, right, who still find networking or reaching out cold to people incredibly uncomfortable. And I think you just have to get comfortable with a rejection. And fortunately,

Josh Felgoise (16:54.624)

I think I was just very comfortable with getting rejected by people, right? Like cold outreach, very early. Like the more I got it, I just didn't care. It was like, look, it's not personal, right? The person just maybe didn't have time, didn't see it. They don't want to talk to you. But the more I got, the more someone said no, right? The more confidence I had to just do it. Now I would say the couple early people, right? Who bought in also gave me the other side of that confidence of like, hey, someone's willing to talk to me.

Right. And that's helpful. I think the other side is like, look, if you don't have that confidence, the easiest way to build confidence in anything is just preparation. And so I would sit there and like do a ton of preparation, read all the articles these people had been in, all of the podcasts they had been on, come to them. And especially if you're young, right. It stands out. Yeah. Bring something up about their business, right. That they're looking at are like.

the 18, 19 year old kid knows about our last earnings report and has an educated question. It's not that hard to stand out when you're really young. And so I think if you come with even a factoid or something they said in an interview, immediately it plays into that person's ego, number one, but also shows them that you actually care and did the work. And that goes an incredibly long way. Absolutely. That's great. Thanks for sharing all of that.

came after the first company, like where you were still in college at that time, what was next for you? Yeah, so I had a bit of an interesting path. I was strong academically, but I'm very open about sharing this. While I was strong academically and starting my company, I fell into the trap that, like a lot of young people do, of developing very unhealthy relationships with substances.

And it got to a point for me when I was about nine or 10 months into my first company that I knew it was not sustainable. I come from a family where almost everyone in my family growing up, right, around me either died from alcoholism, right, or is currently dealing with it or did get sober. And so I always had that awareness when I was younger that

Josh Felgoise (19:14.222)

This is something that has plagued both sides of my family for quite a long time. And so I actually decided after my junior year, I had been interning at Turner Broadcasting and knew that going back for my senior year with the state I was in, right in my mental health, was just not going to be sustainable. And so I made the decision after my junior year to leave school.

I ended up getting sober when I was 21. So just, you know, a few months after, you know, I was of legal drinking age and took a year off. Yeah. Right. I use that time to really focus on myself, to get healthy, right. And be in an atmosphere that was conducive with getting healthy and being sober, which I think you can certainly do it in college, but it's very difficult. Absolutely. And then I, you know, I phased back a bit, I think.

in that time I was running my company and going to school and your response was, know, wow, that's crazy, right? Or like, how did you have that time? I think that right at the time, being successful in school, having a side company, it made me think that I was okay, right? And that the substance abuse issues I had were okay, because I was successful, right? In the eyes of other people. And so taking a step back from that and really focusing right on my health was today the best thing I've ever done.

I think it gave me a degree too of emotional intelligence and maturity that I otherwise wouldn't have. Right? When you go through something like that, you get sober, right? You're dealing with addiction. You have to grow up pretty quickly, right? And encounter those things and really do deep work on yourself that I believe has given me an incredible leg up both in my personal life, but also professionally. And so yeah, after that, I took a year off. I still worked at my company.

I ended up essentially selling it to the company that invested initially because I knew that in order to really recover and heal and put myself in a good path moving forward, running a company and scaling a startup is incredibly hard. And so again, good result right at the time. I also don't think I actually had the maturity to successfully scale a startup at that time in my life. Went back to school, graduated, and then took my first job.

Josh Felgoise (21:37.742)

So that was a kind of year digression from the normal four year college career path. But I look, that was eight years ago. And so I've been sober now eight years since I was 21 and I'm now Congratulations. Thank you. And again, without doing that, I very firmly believe that I would not have been able to do what I have, both professionally, also in my personal life, without having that demon.

right, and working through that. It's something I deal with every day, right? Like I have to be vigilant and I have to be aware of that. And it's the underlying behavior, right, that causes that pattern of substance abuse. yeah, that was a bit of kind of a wrinkle in my story, but one I'm incredibly grateful for. Well, first of all, thank you for, seriously, thank you for sharing that. Like I think seeing somebody in your position who is so successful share that.

side of their journey or their life that has such a stigma around it is so important for young guys to hear. Like truly thank you for sharing that. And I'm grateful to have you on here to talk about that. And I just think like it's such a stigma, such a taboo that we don't talk about and like addiction and substance abuse are things that kind of go under the rug for a lot of guys or any young people in general, especially when you're in college. Like people say you can.

It only counts after college and like it doesn't go away. It's not a thing that goes away. So feel free to share whatever you're comfortable with sharing about that topic. And you've shared on it really beautifully. But what did you do during that year to kind of set yourself straight and work through that? Yeah, no, absolutely. mean, I think there are a lot of different paths that I've seen people successfully take. And I agree with you that there is still a lot of stigma, I think.

You know, when I got sober, you know, in 2017, the stigma was greater than it is now. And so it's been cool to see that. I also think that sobriety in many ways has become somewhat of like a feature in Silicon Valley. Yeah. Right. Like we've moved in the past 18 months into this like hyper performance kind of like flex culture where people are obsessed with wellness and betterment and

Josh Felgoise (23:58.094)

you'll often see that like people do it, right? As like, hey, look at me, right? And I think when I got sober, I knew some people, right? But it was really only people who had a problem. People were not getting sober even in like 2015, 2016, 2017, because they wanted to achieve even more in their careers. Like I'm sure some did, but it was not as popularized as it is today. And so I think in some ways it's gotten better, but it's still there. And early in my career, I was very nervous to talk about it.

Going back to your initial question, right, of what my path looked like, I actually went to a treatment facility after that internship, was there, right, and really thought I needed the time to like be in an intensive environment where I was working, you know, on my emotional health going through, right, what had happened in my life, right, that I decided, right, and had that relationship with substances. And I just felt like it was a accelerated path to recovery.

Right. mean, I think it's similar to like, Hey, if you want to go and write, learn about something, let's say you want to learn about Excel, right? You can go to a 30 day bootcamp or you can spend an hour or two every week. Right. And the 30 day bootcamp is going to put you on a more accelerated path to understanding. And I very much looked at that in the same way. that was, yeah, that was my path. I think, you know, a couple of other things like having.

similarly to a career, having mentors, right? They're called different things and different programs of recovery, but having people that you look up to who have had success, it's the same thing, right? Now in this way, it wasn't career success, it was success of being healthy, right? And having, you know, being sober and doing that in a culture that is very alcohol driven. And then community, right? I think like having a community of people around you.

at my age to both normalize the existence of being 21 and not doing those things was incredibly helpful. And just people who, again, can relate. I decided that I wanted to still maintain friendships with my friends in college and be able to be a normal 21, 22 year old. And so I very much like...

Josh Felgoise (26:15.232)

still hung out with those people, still engaged in nightlife, right? But certainly it wasn't easy at times. So I think having that support network, right? Having a community and also just being, you I think this extends to anything in life, but being brutally honest with yourself and having that honesty to be able to get help and step away when you need, right? Has been critical for me. Yeah. And then I guess I'm also curious about like how you integrated back into

And it sounds, it's like amazing that you were able to hang out with those people still. And you made that decision obviously, cause you wanted, like, I think a lot of people would make that very similar decision, but how did you integrate like back into that? Like, especially with this stigma of college students, being like, like an example I have is like one of my friends and I had him on an episode that we talked about before this. Um, we talked about drinking and like the first response from all of our friends when he told us he was going to stop drinking was like, no, like, okay, like, sure. Of course, like for a couple of days. Yeah.

Which is a horrible response and we talked about that on the episode. Yeah, how did you integrate it back into that life? Yeah, it's normal. Yeah Yeah, and I think I mean when I first told like a lot of my friends generally I think there was an overwhelming amount of support, right? But you I still remember people that were like, why are you doing this? Like, you know, come on man Like you're gonna miss out on our senior year, right? Like I had that Integration I think was difficult right like I took about a year off

to focus on myself, right? And be in an environment that I thought was more conducive to that. I think it's incredibly difficult to do in the same environment, especially in a collegiate setting. When I went back to Wake Forest, I worked with, I guess we called it the Center of Well-being, and I actually helped start a collegiate recovery center at Wake Forest, which had not been built. That's amazing. Yeah, it was cool. With the Office of Well-being, we got a space in the gym.

and essentially had a place for students who were sober or thinking about it to come in a judgment-free zone. Also like having other college students who were doing the same thing. Because when I was at school, I didn't know a single person who was sober had gone through that journey. And so it's still around today. Now I think when I was there, there were two of us. So it was still fairly isolating. But 10, 11, 12 students that are there today, and I think like...

Josh Felgoise (28:37.006)

That's incredibly helpful again of finding that community. But I really gave myself almost a year, right? To like really heal and focus on my mental, emotional and physical wellbeing before I like integrated back in, right? To what I was doing. I don't think everyone needs that, right? I have friends, you know, who have gotten sober now at 23, 25, 28, right? Friends that have gotten sober in the past year. And have very much just, you know, gotten that support and been able to.

kind of stay the way they were with the friends they've had. But again, I think you just need to kind of know who you are. And sometimes it just takes trial and error, unfortunately, as well, you know, to figure out what works and what doesn't work. And I think it's so cool that you did that for college for college kids. That's really incredible. And I think it's that type of thing and this type of conversation that breaks those stigmas down. And hearing from somebody like you on this topic, like is what breaks these stigmas down. So I think.

What you're doing here today and what you're doing in general with sharing this experience is just really fucking cool. So thank you for doing that. Thanks for look. Thanks for bringing it up. Right. And for for having the conversations I think it it takes to write to be able to ask the questions is often uncomfortable for people. So I appreciate that as well. Yeah. It's it's thank you. Seriously. Thank you. And I guess I'll ask you one more thing on this and then we'll go on to the next the next topic. But if somebody came to you now

and asked you for their advice about like what to do or they like were struggling with something or not knowing what to do next. Like what advice would you give to that person? Yeah, I mean, I actually right before this call had someone, a friend, text me right with a friend of theirs who is trying to get sober and has a couple of days under their belt. Again, I think it's very unique, right, to each person in terms of like what I would suggest. But I think the initial thing is just getting support and help where you are.

Right? Number one is like, whether it's going to AA, there are a ton of meetings that are both based within their mindfulness based meetings, right? There are so many different built in communities that you don't know about. And all it takes really is a Google search and you'll find really in any city that there are probably 50 different types of recovery meetings, right? And that's from everything from alcohol to drugs, to eating disorders, to really anything you can imagine, right? Technology like.

Josh Felgoise (31:00.728)

there is a lot of support out there and people that are engaging in it and you just probably don't know about it. That would be number one. Number two would be like, as I got that text, right? Like meeting people and building a community to feel less alone. know, finding other people who are in the same position and just reaching out to your network of friends because I think we're at a point in our society now, unfortunately, where like everyone knows someone, generally multiple people, right? Who are either struggling

right, with substance abuse or have gotten sober. Like, I think now there is more visibility and everyone knows someone in their life who is dealing with it has dealt with it, right? And so again, just like reaching out to people, making it known and I think that's also helpful in that like when you're close people know and are there to support you, right? It makes going out, it makes doing all of these things way easier when you're not living with that secret. So those would be my two things, right? Of like,

tap into the resources you know and the people you trust. And I think there are way more people out there struggling with the same thing, right? Or who have overcome or overcoming the same thing than you would actually think. Yeah, absolutely. And I think one of the coolest parts about doing this podcast, and I just thought of this is when you said like, it takes the person to ask the questions, is that like, I would have never had this conversation with you or somebody could have never, would have never probably found you had it not been for this type of setting.

I mean, at least I wouldn't have and hearing this conversation, like I truly believe you're going to be an inspiration to somebody about this. and now seeing where you are is just really incredible. And like the way you turned it around, like a hundred percent. so now I'll transition to where you are now, or if you, anything you want to add in like in between those two areas of your life from that time to now, can fix the gap and then move forward. Definitely. I mean, I think the one thing.

You know, we obviously met through my current company, which I started about two years ago, but after my first experience with entrepreneurship, I think one thing that has stood out to me in my career and that of others is you often overindex, right, from one job to the next. And so if you have a really bad boss, right, your next job, you're probably gonna be more focused on the quality of the boss than other things, right, that perhaps are even more important to you.

Josh Felgoise (33:19.052)

And so for me having that instability in my life and also the startup environment, I wanted to go to the most stable career, right? Stable job, et cetera. And so I went into consulting, right? Big consulting firm, did that. I worked at Snapchat for about a year and a half, then went into kind of where I wanted to be, which was like the big tech media companies, right? I knew that they were on the cutting edge. They were the disruptors. And so I worked at Roku and then went to Amazon.

Prime Video, which is where I was when I started this business. But I would say that, you know, being at those big companies, which are competitive and difficult to get to, right, without those experiences, I would not have been able to do what I am today. Both building that confidence, right, of like, hey, I'm around really smart people, I learn a lot, I believe in my abilities, but also for me, right, is now a manager of a team.

seeing what I like and don't like in management styles and companies and bosses has been instrumental. So, you I think like everyone's path is different in entrepreneurship, but having the big company experience for me has actually been incredibly beneficial. So that was like, you know, the period kind of 22, I guess to 27, those five years was mainly playing in like the big tech media space and was able to work with both.

traditional movie studios and streaming services, but also got to work with a lot of creators and YouTubers and influencers, which is part of the reason I had the idea to start this company. From that time, you said like you learned about the way you liked managers and the way you didn't, and you've taken it into the way you manage now. What are the things you liked and didn't like? Because I completely agree. I worked at one big company and now I'm at a much smaller company. And I feel the same way about the managers I've worked with and the people I've met so far. So what are those for you?

Yeah, I think my biggest thing is honesty, right? Like, I worked at Amazon and I will say that Amazon is not an easy place to work, right? It is very performance driven, but they're very clear about that. And I have been at places too where, you you put out some type of culture and environment and when you get there, it's a complete opposite. And so I think if you put out, right, what actually your values are, right, and what you expect of people, then...

Josh Felgoise (35:36.566)

No one is walking into a surprise and it's not going to lead to resentments amongst people. Right. You're going to see lower turn. You're going to see people that are happier. So that's one big thing of like, be very clear about what your culture is. and don't try to have this like rah rah or this great place to work if realistically, right. It's a very performance driven cutthroat environment. Right. So like that's one big thing for me of just being honest, right. About it. Because like there are many different company styles that work and don't work.

Again, like just be real about who you are and how people work there. I think the other thing is I very much wanted to be, you know, an empathetic leader who built like a very good culture. Now what comes with that, I think is balancing that with a performance driven culture, right? At a startup, like you have to deliver results, you have to continue to grow. And so finding that delicate balance right between being again, not like

dictatorial in how you work, right? And making sure that people feel comfortable with you, but also making sure, right? That, you know, you set a very high standard is important. I also think as a young CEO and manager, we have people older than you, right? You have to build respect. You have to build trust in a slightly different way. And so from me, yeah, and by following people, I think in my last bosses, people who lead by example, right? Like you'll hear this in terms of like sports teams too. It's like,

If you're there busting your ass, right, and delivering results and people see that from you, I think it inspires others, right, and instills confidence. And so if I'm sitting here and not working, just instructing people, right, and feel like I'm above everything, right, that I don't think that's the way to lead. And so that was one other thing. I always appreciated people that I worked for who worked incredibly hard, right, and I saw that, the care they had, the effort they had, and you want to perform for someone like that.

I think. 100%. So that was one big thing for me. you know, seeing what I liked and did not like about managers and trying to apply, you know, the positive things to my working style and management style. I completely agree, by the way, like you want to work for the people that you that are one, like trusting you, sharing everything, being very honest about it and also working hard themselves. Like you just know who they are. So I completely agree about that. So how did you meet Josh Flagg and start this company?

Josh Felgoise (38:00.43)

Tell us about this new venture you've been doing for 10 years and everything. Yeah, absolutely. So while I was at Amazon, I had a friend who I met in LA. So we were like, you know, just met this guy. I reached out to him cold on LinkedIn when I graduated college. He had started a media company out of college and I just looked up to entrepreneurs. Has now become a very good friend of mine and ended up going to high school.

with one of my now co-founders Andrew Schaenfeld. So it's, it's Andrew, Josh and I, and Andrew and Josh had both come from the worlds of real estate, right? Andrew was in private equity, commercial real estate. Josh obviously has been a real estate TV personality and real estate agent in Beverly Hills for the last 20 years. And so they came right with this idea of, Hey, like, is there a podcast or something to be built right around Josh? Like.

You know, we know he's on television, television is regressing, but like, what is there? Like, how do you build a media What's next, right? Yeah, and so I had gotten looped in of like, you know, I was in a position where I understood like big media and tech, right? I also understood social creators, right? And influencers and how to kind of bridge that gap. And so I met the two of them, yeah, probably about two years ago now. And for me, I knew nothing about real estate.

I had never seen any of the reality television shows. I didn't consume real estate content. I was a homeowner at that time, but outside of that experience knew very little. And so I spent the next really month, month and a half just studying the space, seeing like who's creating content both in television, who are the creators that are succeeding? Like how many real estate agents actually make content? How big is the industry?

Are these people making money? Are they spending money to create content? I just wanted to understand the entire space. What were the motivations? What were the interests? What was difficult? And ultimately in thinking about media, was there an audience need? Was there something missing from the content that all of these agents were creating? And so the first iteration was, let's focus on Josh and see what are his pain points.

Josh Felgoise (40:15.286)

and see then if those pain points of a top producing agent who has scale are relevant to other agents as well. And so quickly what we found was that agents were paying money to create content, right? It was not something they are great at. It's not something they wanted to do. Some of them do, right? They were spending money on it, but they didn't look at that content as valuable IP, right? Or valuable intellectual property. It was generally a marketing expense that they wrote off, right? To appease a potential client or an existing client.

Got it. So number one for me, right, coming from a content background, I was like, that's interesting, right? They're spending a lot of money on something they don't view as valuable, but audiences, right, the general public does, and they're not making money on it, right? So it's basically a cost center. Number two was what I found in looking at the content that was being made. It was very much bifurcated between like showy reality television, right? That was like applicable to the masses and was fun and had manufactured storylines.

And then like old school publications, right? There were the text-based kind of news breaking more traditional news players that had been there for 20 years. But there was nothing in the middle, right? There was nothing and, you this was kind of morning brew's early thesis was like make business news fun. Real estate news was not fun, right? The industry was not fun. It was either sensationalized, right? Or fairly boring into the point.

And that boring information was generally only being read by the top 10 to 15 % of the industry, right? Because it was high brown, it was not easily digestible. And so we tested those concepts with Josh, right, in the following six months and the content performed, right? We went across every platform, we optimized for each platform and we exploded his socials. Right, the third side is like, how do you actually make money from this, right? Like, how does this scale?

And ultimately for any content business, right, there are three pillars of making money. It's advertising, right? It's community. So it's a direct one-on-one relationship with your customer. And then number three, it's generally some type of commerce or product, right? Build the audience. The audience is happy with the content. Form a deeper relationship with that audience. And then third, build something that that audience wants. And so we had to figure out number one, right? Like, was there an advertiser need?

Josh Felgoise (42:31.928)

what advertisers spend money against this content and why would they spend money here rather than where they currently are? And we found a lot of success, right? Like fundamentally the premise behind this company too is people follow people. And it was not easy to reach the voices of influence in real estate, right? They were all disaggregated. They weren't repped by people, right? And they were like, why would I do that? And so there was a gap between real estate technology companies.

many of the interior design and appliance companies, right, really had architectural digest and dwell in a couple other places to spend money that were very expensive. And so we tested it with Josh first and found success, right? And so early on, and I was still working at Amazon at this time, was like, let's test this around one person, see if it works, and then how do we scale it? And so that was phase one of this, right? Derisking ourselves by testing it with someone, right? And then saying, hey,

if we are to launch this thing, this is how we apply it to other talent. And so very much that was the first phase of things. then, yeah, happy to kind of go into the rest of it and how we did the early build out and where we are now. How do you make money from it? So right now, so quickly, right? That was the first iteration. Okay, yeah, yeah. Let's build around this person. What we then found, as I alluded to, is there are all these big personalities, right?

but they either weren't making content or were not making content in the right way. And so our premise and thesis was finding people that agents, real estate agents looked up to. And that required that they were trusted, they actually sold real estate. And two, if they were being looked up to, they had some type of audience or scale. And so the idea was to create a destination with all of these leading voices, with a state media being the umbrella company. This company that is

composed of the top producers in the space, right? It has a certain standard in terms of who we're going to work with. And we're going to create content in original formats across every medium, right? That have not been done before. And so that was kind of the high level goal. And we launched a business about a year ago. launched a pretty cool. And, you know, today, yeah, we have three podcasts, which are three of the five biggest residential real estate podcasts today in the United States.

Josh Felgoise (44:53.262)

We have six newsletters with over 120,000 readers, 70 % of those being real estate agents. And then we have over 210,000 followers on YouTube, Instagram, Facebook. Okay, wow, that's incredible. So we've built that in a year. So our audience overall, we've built an audience of about 330,000 on our owned and operated channels in less than a year. And have done that, right? By creating original content with these people, right?

we found that audiences have responded to it. So where do you go from here? What's next with that? That's first of all, really impressive. like you've you found a gap. found like a niche that you bridged the creator with the consumer and both sides were interested parties. And like I think one of the biggest things like people have seen in real estate now is the Netflix show. What's it called? Selling Sirhant or something like that. They're selling Sunset and then there is a new Sirhant show. I can watch that too. Is it buying Manhattan?

I believe it's name of our show. Is he like a competitor to you or what's that landscape like? Yeah, good question. And just to quickly address how we make money and that also then plays into how we see the company moving forward today, right? It's an advertising business. And so anyone from the big real estate platforms to real estate technology companies that want to reach agents, spend money with us.

luxury appliances, interior design, financial services, right? Those are key advertising categories. And those companies sponsor our newsletters, right? They sponsor our podcasts. They sponsor our original series. And then we do bespoke custom integrations, right? As well for advertising clients. Smart. As I mentioned earlier on what I believe are the three pillars of a media business, right? Number two is that direct connection from your audience. And so we've spent the last year basically A-B testing what our audience likes and doesn't.

The great and difficult thing about content is your success is right there. And viewership and engagement and shares, it can be incredibly demoralizing when you think you have a hit and put a lot of time and effort into something that is viewed by very few people. Then it can be a wonderful surprise when you expect the opposite. And so we have a good understanding now of what we believe our audience wants more of and what they've asked us for. And the great part again about having...

Josh Felgoise (47:15.928)

this relationship with consumers as we can pull them in our newsletters, right? We can ask them on Instagram. And so the next phase for us is launching a member community, which will be- we go into that, can you give an example of like what works or what the community likes? Yeah, absolutely. So a couple of things that we found, right, in terms of what the community likes. Number one is putting these big talent into formats, right, that they otherwise have not seen. So it's something new and novel.

And maybe these formats exist in other niches or broad scale media, but putting our talent into situations that people have not seen them in. An example of that is with my co-founder, Josh Flagg. We've taken the traditional house tour, which is loved by people. People watch it right in the background. And we've turned that into a comedy series, where he tours a house with a comedian. And so you have Bill Burr ripping this $18 million house in Beverly

hills to shreds, right? That's an original concept flows into his personality, right? That's the more consumer fun stuff. The other side is like the education, right? Of we have found that when our talent are raw and vulnerable and have conversations with other leaders in the space, it is inspiring and highly educational and people want more of it. And so with that, right in our podcasts that we have found

the true kind of one-on-one difficult conversations about the market, how people got their starts, what they should be doing now, again, have been really our top performing. And so we took that idea and said, hey, how do we allow this audience and the realtor to have a more direct relationship with these leading voices in this space? And so we'll be launching a member community with five of the biggest real estate personalities in the US next month. And that will be 10 to 12.

hour long AMAs right every month. So we'll have custom curriculum every month, right? The top talent we'll be talking about will facilitate introductions with the talent, right? With other members in the community and are really trying to build something right. That stands out. So it's like masterclass for real estate. Yeah. So it's, you know, a lot of it is live, right? So I believe that like courses, right? Or somewhat like you need to have a vibrant community. And so it's going to be right.

Josh Felgoise (49:34.606)

kind of the one to 10, one to 50, one to 100 education, right? With the biggest names in the space. But then also, to be successful, you can have big names coming in and talking, but you need a really vibrant community. And so we'll have community managers and an entire team that's facilitating introductions between members, right? Trying to set up those relationships, those learnings, and also a referral network, right? So if we have a member in St. Louis,

and they have a client who's moving to Tampa, Florida, right? We're actually generating business for those people. And so those are a couple of highlights of the community as well, virtual in-person events will all be core tenants of what we'll be building. But that's the second step, right? In terms of like, hey, we have this great media business, we have wonderful advertisers, but let's get that talent, right? That's core to our business and have them interact with the real estate community and our audience in a more meaningful way. And so that's a big focus of ours moving forward.

It's a really great idea. Is anyone else doing that right now? So you mentioned Serhant and what he's doing, right? And I have a great deal of respect for Ryan and what he has built. I think the differentiator there is he's building a national brokerage. And so he has used media as no other real estate brokerage in the past has. Sotheby's, Corcoran, Compass, he has put content first, and I think it's brilliant. He's used content to attract new agents into the firm.

And he has used content to get more listings. And I think real estate and content are one-in-one. It's such a visual medium that if you're not succeeding with content in the future, you're not gonna succeed in this business. What he's doing though is he is very much utilizing that media again to build the brokerage, which he's done incredibly successfully. Now, I think our core benefit is we are brokerage agnostic.

So what we want to do is work with the top talent in every state across every brokerage, right? Who can really tell the story that realtors are looking for and can provide the information. And so for us, it's, hey, let's take a far more national approach, right? Let's work with talent. doesn't matter what brokerage they're in. We're not trying to drive anyone to a brokerage. And that allows us to have more flexibility in what we create, right? It allows us to be more flexible and the risks we're willing to take. And so while again,

Josh Felgoise (51:57.858)

real estate content core to his business, a very different angle, right? And what he's trying to achieve versus what we're trying to achieve. Yeah, we work with some of their agents, right? We're making content with them. So again, I think they're in the same space and ultimately, right? As Reed Hastings from Netflix will say, like we're in an attention economy and anyone who's taking attention from me, right? Can be seen as a competitor. So, and that way, absolutely. But they set a very high bar.

Yeah, they set a very high bar in this space and have, I think that's motivating for us. What is the most challenging thing for you about doing this on your own, about starting a company and being 29 years old and balancing relationships and life and everything while doing this? What's the most challenging part? I would say it is what you what you just said, balancing everything. You know, it's easier almost to just be fully heads down and say I'm going to be completely absorbed right into this.

At the same time, I have a life, right? I'm married, I have horses, I have other passions in my life. And, you know, for me, it is very difficult to step away from work, right? As I think it is for many entrepreneurs. So I'm constantly trying to find that balance and show up in the other areas of my life. I think the other thing, right, for me, this go-round is building a team, right? And making sure that you're building a team in systems and processes that work well.

I found that I'm good at taking something from zero to one, right? Like an idea, coming up with an idea, building off that idea and actually getting something on the ground, off the ground, excuse me. But the skillset of building, launching a company, raising money to like scaling, now we have 12 people to, let's say we scale to 20 or 30, it's a very different skillset, right? Than being a solo operator and just building a concept, right? To a point where you can either self-fund it or raise money. And so for me, that's also.

probably the other biggest thing, is how do you build a team, right? And how do you build a team that works well? Like how do you build and scale a well-oiled machine? And so that is the most difficult thing for me today as well, right? Of building that, because I haven't done it, right? With as many people. Yeah, it's, I mean, the first time you're doing anything has to be a challenging time for it. Is there anything you wish you did differently in your career than you had?

Josh Felgoise (54:15.21)

I'm grateful for all the experiences I've had. I think it's led me up to where I am now. I would say the one thing is do a lot of research on a company before you join. Right? Talk to people who work there. Talk to people who will work for the boss you're going to work for. Really know what's going on to the extent you can. Because I have definitely had experiences where I thought I was getting one thing and got something completely different.

And that goes back to my point around expectations, right? And knowing what you're walking into. So that would be one area. The other would I think should be just like to trust your gut. You know, with some opportunities in the past, it's like, this is too good to be true. You know, are they really asking you to do this? Like very much trust your gut and trust your intuition. Griff, what advice do you have or what would you tell your 20 year old self? Put yourself in uncomfortable positions and be okay.

with the difficulty that's going to come from that. I did put myself in some uncomfortable positions in terms of working at difficult places, but I think at times too, right? Like I could get comfortable in a role or a position. And so I think especially earlier in your career when you can, you have to have a high risk appetite, right? Especially if you want to accelerate quickly. And so having a high risk appetite.

early in your career, even for me, even earlier, right? I think would have would have paid dividends. Yeah, that's great advice. This is a really cool conversation. I loved having this talk and I think we went in really cool ways that I didn't foresee completely. And I appreciate everything you said. And I think people will have really amazing takeaways from this conversation. Thank you, Josh. I really appreciated it. Yeah. And we will we'll talk soon.

Sounds good. Talk soon. That is the episode. Thank you so much for listening to this week's episode of guys said if you like this episode I really did please like subscribe give this podcast five stars That's one two, three, four five on Apple podcast Spotify wherever listen to podcast I don't really care as long as you have a five stars in a review. I really appreciate that Thank you so much If you have any advice or anything you want to share with me or feedback on this podcast I would genuinely appreciate that so much if you want to send it to me directly. I have an email address It's josh j o s h at guyset.com g u y s e t com

Josh Felgoise (56:34.668)

And if you want to share anonymously, think one of the best ways to do it is through Reddit. It's r slash guy set r slash GUI SET. Somebody left an incredible piece of feedback on my Reddit page. I hadn't found until a couple of days ago, cause I don't check it that often. Now I will obviously, but he left it about 50 days ago and it's the most incredible feedback. was just like a gift from this person. and it was not all positive. It was like a lot of constructive feedback that I just really appreciate it. So if you have anything you want to share with me,

And you may not want to share it directly. think that's a really amazing place to do it. I would really appreciate that. So also if you have anything you want to talk about, they should be talked about sent to my email or to that Reddit or to my DMS on Instagram, Tik Tok. It's at the guy set T H E G U Y S E T and I will be sure to talk about it. Thank you so much for listening and I will see you guys next Tuesday. See you guys.