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The Leap: Talking solo entrepreneurship with creative founder Alex Wolf

Every other Wednesday, Wethos CEO Rachel Renock hosts an IG Live series highlighting the stories of creative entrepreneurs who took the leap toward working independently or starting their own project. For this episode, Rachel sat down with Alex Wolf, creative executive producer and founder of Alex Wolf Productions, a creative branded content studio. They discussed Alex’s leap toward building a production company that’s worked with brands such as Dropbox, Snapchat, and more. 

Note: The following interview has been edited for clarity.

RR: Alex has built this really awesome community of over 30,000 creative entrepreneurs that are super engaged, talking a lot about meaningful technology. Today’s episode is for all of you out there who maybe want to go big or go home. So Alex, in your own words, I’d love to hear a little bit more just about your background and how you got to where you are. 

AW: Yeah, so I’ve been into technology since I was a little girl. Both my father and my grandfather were super nerds who were into building radios and, you know, connecting to computers. So I was an early adopter by default and I was able to take advantage of the huge cultural shift of the Internet, kind of going from a hobby into a way of life. So that history is what got me to start my own business and really leverage the exponential potential of the Internet. 

RR: Did you always consider yourself to be an entrepreneur? Or was there a significant moment that sort of made you go down that path?

AW: Well apparently I sold a Pokémon card in third grade and I got in a lot of trouble. But to this day, I don’t remember doing that. So I don’t even know. I didn’t start to see myself as an entrepreneur until about 19 when I was really underwhelmed by my college experience. My parents are both college educated and they expected me to go to college and I really just didn’t want to go. I mostly didn’t want to pay for it. That was the real thing I was trying to make it make economic sense. And it never was. And so I was like, OK, what else can I do? And there was a lot of fear because of course, I was afraid that I’d be flipping burgers for the rest of my life and stuff like that. But I just kind of kept pushing buttons until it all made sense. 

So, yeah, I would say around 19 or 20 is when I started to take entrepreneurship more seriously, but I still had no fucking clue what I was doing, like not even an inch of what this all really means. I’m just now learning what being an entrepreneur means 10 years in the game. 

RR: What was your very first move when you were just trying to get that figured out? You’re like, all right, I’m going to start something. Now what? 

AW: So the story is that as a 19 year old, I was super desperate for fame and fortune, just like every other American girl. I was like, how do I become a star? Like, how does that happen? And how do I get to the other side of this mountain? And it was pretty dark. I struggled with eating disorders and all types of mental health issues and had trouble just accepting myself and loving myself. 

And I really saw being an entrepreneur as the answer to those things, which was crazy in retrospect. But I went down to L.A. and I took a seminar on how to be a host. And I was really focused on how to get on TV. This was how little knowledge I had about how businesses work, because I thought you just became famous and then you became rich. 

The whole premise of a lot of my work now is demystifying that as much as possible so people don’t fall in the same rut. So I went down there and this was fresh out of high school. I cut class half of my high school experience, and when I would cut class, I would just be on Twitter all day, just chronically sickly, going back home to be on Twitter. 

So when I went down to L.A., I was trying to figure out how to get on TV, how to become famous. And the lady there was like, TV is dead, focus on social media. And it was my “a-ha” moment because I was like, OK, I’m already focused on social media every day. And then I came up with the concept for Boss Babe, which was my first company, and it had the right elements. It spoke to the right time and it took off. 

RR: I love that. It’s so interesting. Talk to me a little bit about that process that you went through in eventually selling Boss Babe. How did you come to the place of feeling like, OK, I’m ready and this is?

AW: I knew I came to that point when I was no longer interested in taking care of it. You know, it’s kind of like having a pet and knowing that you’re about to move. And the reality is you’re not going to really be the best caretaker. And you have like a crowd of people who would love to take this pet and would do right by this pet. So that’s the kind of position I was in. I was really kind of struck by how much social media was changing society. And I really wanted to just talk about that. That interest was clashing so much with my daily duties and what I had to do to run the business. So I took a huge risk. It was not even a financially motivated thing. I just wanted to pivot to spending my time focusing more on tech philosophy.

RR: So process wise, because I’ve never sold a business before, what does that look like? Did they come to you or did you look for somebody?

AW:  I had already operationalized it for about a year, meaning that I wasn’t really touching it and I would just get reports from two of the people who were running it. But I believe that being a real CEO means getting your hands dirty, talking to everybody on every level. And so I was more like a distant board member type than an employee of my own company. So after a year of seeing how smoothly that went, the people who were managing it were interested in buying me out.

That time was such a blur for me. Part of the plague of early success is that you’re dealt with all these responsibilities before you even know what you want to really do or who you really are. So it was a relief in a lot of ways to be able to say, OK, that was weird. That was fun. That was cool. Let’s go focus on, like, who I really am. 

RR: Yeah. So I want to talk a little bit about your pivot to meaningful tech and this conversation that you’ve been sort of having since. Where did you start with talking about this topic and how it evolved over time? 

AW: I think the biggest pivot happened as I was writing my book. My dream was like, I’m going to sell my company and I’m going to become a writer and I’m super low key and I’m just going to have a free bohemian writer lifestyle. And I am very sensitive to media literacy. And it means a lot to me as a content creator to have high comprehension in not just what I’m talking about, but the medium in which it is being expressed. And here I was, Miss Bookworm in New York, walking around thinking, I’m Carrie Bradshaw. And I realize that people aren’t reading as much and that I was going to walk into an economic trap by committing to writing. 

And I was again really asking myself, is this really what you want to do? As much as I’m an artsy fartsy, I am also very much a business person at the end of the day. And so I was like, how do I grapple with the media climate of our time, the comprehension landscape. It’s not that people don’t read. Obviously that’s a generalization. But I throw my content and at the end of the day, my livelihood into risk, into a higher liability by committing just to printed word, especially about complex topics like tech philosophy. 

I saw it as an opportunity to ask, “How do I open this?” You only have a small window of time before the attention span gets so short that you can’t even get a complex idea through the door. And so that’s when I decided to do my documentary and just focus on high comprehension media, which is video and images and audio and less printed word, even though I do want to do more printed word. 

RR: What do you think is part of shifting the solution into more meaningful interactions? How do you think maybe existing platforms or new platforms transform or change from what we have today, which is like social 1.0? 

AW: I have a presentation where I break down qualifiers of what I think makes something human-friendly technology. So anyone listening who wants the in-depth answer, that’s where you can find that. But just to briefly go over it, one of the biggest components of effective communication is presence. And from a lot of our current communication tools, telecommunications kind of takes the presence out, which was firstly put in there for convenience, meaning I can send this person a message and they don’t have to be present to get it. But once they get it, they will respond back. And I don’t have to be present when I receive it. But it’s kind of like let’s dump messages into a dumpster and then it turns into let’s dump images and let’s dump articles and let’s dump everything.

But a lot of us are using it as a primary method, particularly with texting technology, which was invented for very brief short messages, which is now turning into a way that people are learning to, to introduce each other, to date each other, to socialize. And I don’t think it is an appropriate technology because it doesn’t have the same presence unless it is an instant message, which was what we initially had and what the way that a platform like AME or AOL Inc. presents was by communicating to the room when you or when you were or were not available to speak.

RR: Yeah, totally. So I want to, like, just zoom out a little bit and I’m just very curious about what’s going on in your brain and imagination. If you had a full team of designers, technologists, engineers, what do you think you would do? What are the types of features or platforms that kind of float around in your head? And what would you like to see brought into the world? 

AW: Well, I definitely don’t want to give that idea away on this program. But I do think that social media platforms are a really rude awakening in regards to understanding that they should build incentives in favor of the creators instead of against them. The algorithm is this obstacle when it really should be a friend, because creators are obviously providing the media, the information, and the entertainment, but platforms are so committed to selling ads and only ads. I think we’re starting to see the shift just now. We’re seeing the success of Only Fans and people realizing, “Wow, people will pay directly for my content.” 

It’s like we have to sift through garbage, not only to hear from the people we want to hear from, but for those people to find us and and all in the name of selling ads in between. It’s just too hard to stay in contact with your audience and to have real ownership over distribution to access them and the trust that you built. So we have really nasty landlords, in my opinion, and I don’t think they really see, like, “Hey, dude, I’m helping you out. Sorry for making you billions of dollars.”

RR: It’s frustrating. I hope that there will be some new emerging platforms, people building those platforms. So, last question. For anyone who is thinking about taking the leap, what’s your biggest takeaway for them in terms of making that move to go for it?

AW: My two pieces of advice would be: One, don’t expect anyone to believe in you. It’s totally normal. You’re asking too much for people to believe in you. But know that you’re not doing anything wrong if you’re in the beginning and people are like, “What do you know?” I’ll never forget in 2013 when I said I wanted to go into social media marketing and the one person I trusted was like, “You really think there’s money in that?” 

And then the other thing is practice discipline and have pride in that discipline. And like, I have this idea and we’re just going to do this all Q1. We’re just going to do this. And then we’ll talk about that other really exciting thing I want to work on in Q2 or Q3. You know, there’s a time for everything, but you just can’t do everything at once. I do believe that.

RR: Yeah, I feel that really. I feel both of those points too hard, maybe. Well, thank you so much for joining us. I’m really just grateful that you came on and we got to chat. And I’m excited to see what you do in the next year or two because I feel like you have something big. 

AW: Awesome. Thank you so much.


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