TE 28: Alex Obert: Journey of a Frontman


Alex Obert is the founder of Journey of a Front Man. The website transitioned from a journal of Obert’s attempts to become a front man of a rock group to an interview site featuring front men of all types. Obert offers his definition of a front man, talks about his love of music, and how it helps him land some of the biggest names in entertainment for interviews.

Today, you’ll learn 

  • The hustle it takes to build an online business
  • Working for little or no pay while you’re building your internet presence.
  • How Alex was able to overcome his social anxiety.
  • Being creative — using the things you love and live for — to build your empire.


Alex is the founder of Journey of a Front Man, which started as a journal of Alex’s efforts to become the front man of a rock band. “There were no interviews yet,’ Alex explains, “it was just me talking about going to voice lessons, and writing songs, and keeping my supposed viewers, and readers updated on everything.”

When his efforts failed on that front, Alex fell in love with interviewing other people. Saying “it attracts far more people because everyone knows the people I’m interviewing, for the most part. And it’s just far more interesting,” Alex decided he’d keep the title, since most of the people he interviews are musicians, or front men of some sort.

Alex also says he’s redefined the meaning of the term “front man,” as well.

“A front man is someone who leads their life, and takes control, and action. That’s how I see it.” says the front man interviewer.


Jordan asks about Alex’s recent birthday when he turns 25 on the same day of Jordan’s mom’s birthday – September 29. He also mentions that his birthday is very close to Alex’s. Jordan turns 20 on the 12th of October.

Alex stopped in Georgia (not far from where Jordan lives) for Southern Slow Bar-B-Q on his way back from Florida.


Alex says the first album he really considers listening to as an entire work, was the Blink 182 live album, The Mark, Tom and Travis Show. In the seventh grade, Alex took the album on a trip to Williamsburg.

Having discovered a passion for music at an early age, music takes a back burner as Alex found writing as a passion. He writes for the school paper during college, “I was the music guy writing music articles, interviewing faculty and staff. It was a good time,” explains Alex.


Alex tells how his “Journey of a Front Man” was a failure.

In 2013, Alex was seeking an opportunity to front a band, eventually ending up being kicked out of a band he helped start by a friend.  “I guess I wasn’t their cup of tea, or something like that. And that friend calls me that Monday and just doesn’t hold back on it. He’s not trying to be a dick or anything, but he’s just paraphrasing, and quoting what they said. So that was the final straw of the whole band ridiculousness,” he says.

So, once his attempts to be selected as the front man of a band, Alex returns to his college days of interviewing artists and musicians – something he has already returned to during his auditions, already having interviews with Andrew W.K. and others.


Alex says his journey to find himself took several different directions in college. “I didn’t know what I wanted to do, because I went to college wanting to get into video editing, and then I lost interest in that. I got into radio, the college radio station, lost interest in that. And then I found the opportunity to write for the paper. It was early 2009, and the first article I submitted was an editorial piece of Seth Rogan, of all things. And I just – it was like seeing your own work in the paper just blew me away, it was so cool.”

Alex replies to a request from Teenage Entrepreneur host, Jordan Agolli to offer advise for others who may be seeking for what it is they are supposed to do, “ust try different interests and hobbies to find yourself. Because, like I said, I went into college in 2007 with one thing in mind and I left doing a complete 180.”

Jordan relates with Alex, recalling a time when he had sold his first business and was sitting around doing nothing. After a friend confronted him, Jordan gets a job at California Pizza Kitchen, and two months later, he started Teenage Entrepreneur.


Alex Obert says he graduated with an Associates degree in 2012, which was longer than expected because he kept changing majors. “A lot of it (college) was experience… how would I know I wanted to write, or even try radio, or video editing, or anything like that. That’s half the battle right there,” Alex continues, “I also made great friends. So, it’s a lot of different things going into the recipe.”

Journey of a Front man started in June, 2012, a month after graduating, says Alex. “it was pretty basic and careless as the point with the whole Front Many Journey itself, and I left the site unattended for several months in the beginning,” he says.


Alex says he knew he wanted to be a front man even before he graduates from Community College. “I was doing the voice lessons, like March or April of 2012.”

Alex says he left the website alone pretty much until the following year, “that’s when the whole interviewing started.” In the months between voice lessons, auditions and starting the interviews, Alex “was working at the movie theater, leaving there, working at CBS, because I wasn’t in school I wanted to make money. The resume world is crazy right now, so, just take what you can get sometimes for money.”

“It was just for fun in the beginning,” he explains, “because it was going on while I was doing the chronicling of the Front Man Journey.

Alex admits that he and his mom nad one argument about what he was doing. “I’m like, ‘yeah, but, I’m doing stuff, I’m doing this site.’ She’s like, ‘no, you’re not. It’s just sitting there, you haven’t done anything with it in months.’” He says he guesses that whips him into action, and before you know it, he’s interviewing stars in the entertainment industry.


When Alex transitioned his website from his own Journey of a FrontMan to that of other leaders, he started with an email interview, explaining, “this was just the novice way.”

Jordan says he loves that Obert wouldn’t take no for an answer, “a lot of people would be like no, they’re not going to answer my questions, they’re not going to respond. How did that (conducting email interviews) go?”
Alex admits that he had to ditch the email interviews, in part due to the long delay in responses. In a phone interview, “you get everything you need right away,” and, he says, “without naming names, some people just dodge questions.”


Journey of a FrontMan’s Alex Obert says his big breakthroughs comes as a result of his interview with Andrew W. K. – a well known musician. Referring to him as a “renaissance man,” Alex says “I wrote an honest email, and a concert review that was passed along to him, and he shared it on Facebook.”

Alex says he didn’t think the review would go anywhere, “I was just testing my chops as a writer. And then, all of the sudden, through that, and an honest email without any legit names that I interviews, I was granted that first interview. It was insane.”

He recounts how he wrote a review of a concert which included Steel Panther and Andrew W.K. Then, he contacted W.K.’s agents, pointing them to the review he wrote on his website. “That must have been what got me the opportunity. I don’t know for sure, But I certainly think it helped.”

Alex says that at the moment of the interview, “I was so nervous. But, I just pulled through and I just pulled through and just tried to believe in myself.”


“I give the whole email to interview confirmation about a week. I mean, sometimes it varies, and you just need that right level of persistence where it’s not too much or too passive,” Alex explains.

Teenage Entrepreneur Host, Jordan Agolli asks Alex if he remembers any of what he said in that email to Andrew W.K.

“ I didn’t really have any names to mention that anyone would know that I interviewed, I was just treating it like a piece that I was writing. Just being honest about hey, this is my Front Man Journey, and Andrew W.K. is a giant influence on me, and I’d love to pick his brain for the site. And then sent the concert review a couple days later. That’s how it all started,” Obert offers.


Alex explains that you have to have confidence to request an interview with one of your heroes. “Because I didn’t have much depth, I didn’t realize I could back myself up” like he did in that email to Andrew W.K’s publicist.

But, he confesses, “Rejection is my Kryptonite.” Whether it’s jobs or girls, or even interviews, “

I got discouraged a lot in the beginning because I’d get rejected when I didn’t have the depth of the roster, and was just trying to write. Not everyone was as accepting as Andrew W.K.’s publicist, unfortunately. So rejection, sometimes I’m nervous to put myself out there. But with all the names I have that I’ve interviewed, it’s like I’m way more apt to put myself out there now.”


Alex recently landed an interview with comedian Dane Cook, a favorite of Teenage Entrepreneur host and founder Jordan Agolli. “How did that work?” asks Agolli, “because he’s very well known, and he’s not an easy guy to reach, how’d you get in touch with him?”

Alex says, “I was just thinking of who to interview, and I mentioned the band Steel Panther before. He has performed on stage with them, and he’s friends with them. So I was on my phone and I didn’t have copy and paste, and getting my list and all that together as easily, so I just looked up his rep and just sent another honest email saying, listen, I would love to get him on the line to talk about his love for Steel Panther and music. And welcome a different type of conversation, as opposed to what he’s used to.“

Jordan notes that Alex didn’t approach Dane the way everyone else who ever landed an interview with the star comedian did. “You were just different than everyone else. “Because, I guarantee, if I emailed him, I’d probably ask him stuff about what everybody asks him about. I bet no one’s ever asked him about Steel Panther in an interview.”


Alex explains that the real trick is to be a great interviewer. “You really have to consider the interviewee, too.” Because I will spend hours looking up past interviews from the past year or so, to avoid certain questions that are — have already been asked.”

Alex also admits to subscribing to IMDBPro. “That’s where they give the info for who you need to contact to get these interviews. I realize that anything that says ‘manager, publicist, or agent’ is good,” he explains. “Some people might not have into, and some people will shock me if I see their info. That’s when I send all the emails. And that’s when the courage is built up.”

Alex says he sent the email to Cook’s publicist in mid-April, and conducted the interview in mid-May. “To candidacy talk about music. I just had to get that out there to give him props for (how quick the response was), just two guys sitting down and having a conversation over coffee.”


Confessing that he’s uncomfortable in public situations, Alex says he’s heading to New York City to cover a show and sit down with one of his favorite musicians, Pauly Z. for a candid one-on-one discussion.

“He’s releasing an EP, so, I was checking in on it, and offered to do a coverage, so we agreed to meeting up today at his show in New York City. I lived in Connecticut, so , it’s just a two-hour train ride. Going to heat there after this, get to the show and just sit down with him for an hour before-hand. It’s just going to be an awesome time,” Alex explains.

Alex Obert says he’s learned to treat stars like real humans. “Treating them like human beings. You can respect their work, because they put out great stuff, and it has an impact on our lives. But, when you’re fact-to-face with them, be a human being (not a fan).”


Noting that Alex admits his troubles in public and social situations, Jordan asks Alex how he is overcoming that pain involved in personally asking musicians for interviews.

“Just a couple of words,” begins Alex, “don’t be afraid to ask… and the persistence.”

Alex says he’s a big fan of business cards, “I get the highest quality ones. Some wil be free on the site, and they’re jut flimsy basic ones. Some will be ten dollars, and they’re a little better. Mine come to forty dollars for 250.”

Alex says his cards are sturdy, glossy “and they have a custom design on both sides. So, I feel that, right off the bat, makes an impression that it separates me from the person who has the lousy business card.”


Alex admits that he’s making very little income from his website. “It’s making a little bit from advertising, which goes into my PayPal account. I have to make like, with the views, it has to be $100 before I receive payment. And when I got that recently, it all went to advertising,” he explains.

To keep doing the interviews, Alex keeps working, “’m in between jobs right now, and trying to work on my résumé to make it stronger and more noticeable. I’ve done the retail thing. I did a restaurant job … it’s just finding a fit. It’s a struggle.”


Jordan explains that he asks his guests and audience alike, “what do you want your legacy to be?”

Alex responds, “the guy who valued hard work, passion, and a love for what he does over anything else. And just being the guy who took a chance, and had it pay off. And the diverse list of interviewees.”

Teenage Entrepreneur host and founder, Jordan Agolli follows up with a question concerning Alex’s desire to follow his passion, “what advice would you give to someone that has an idea that — whether that’s similar to Journey of a Front Man, or my show Teenage Entrepreneur, what advice would you give to someone who wants to pursue something – but it’s not going to bring them any money, and they’ve got to put in that hard work initially?”

Alex responds simply, “work twice as hard.”

“It’s motivation,” Alex explains, “and it just feels good. It feels like you’re getting a lot accomplished.”