"Networking is kind of like throwing a Hail Mary"

Alex Dobrenko's airtight insurance policy on how to never have a real job.

Welcome to The Net, an interview collection about how connections, networking, and good omens have enhanced the lives of the most interesting and creative among us. 

Today’s guest is a really cool lil weirdo who writes one of my absolute favorite Substacks, Both Are True. He somehow reminds me of Kuzco from The Emperor’s New Groove, but if decided to pursue a career as an artist.

Alex comes from the film and TV world and has done a bunch of cool things as a writer, actor, and comedian. Alex also works in tech as an early stage creative person and currently spends his time at Sublime. 

This was more conversation than interview.

I’m in bold and Alex is in not-bold. Here’s the blurry pic he gave me to use:

OKAY meet

Alex Dobrenko`

in his own words!

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I think of you as, like the troll of Substack, which I mean as a compliment. I would imagine that your take on networking is also very unique and different. Can you speak to that? 

Yeah, yeah. I mean I think the word networking is sort of like, stained, like its a a means to justify an end. It feels like you’re just doing it for something else.

I remember when I started out on Substack, I did a lot of reaching out to people whose work I like, without expecting anything in return and that felt really good. I don't do that as much anymore, but I do talk to a lot of people on substack all the time. Lately, my networking game has sucked, you know? And by that I mean, I am really bad at getting back, and I feel bad about it all the time. And I just like, can't get back to people. And I know no one cares that much, like, I’m okay, but, but for some reason, it really bothers me. I don't know if that really answers your question. 

In my experience, networking is something that just ebbs and flows. At some points in your life, you're like, I am going to reach out to a bunch of people that I admire, whose writing I like, and some points you're like, how come I can't fucking get back to one single person. I think it’s just seasonal. 

What do you think it is about the season of your life when you took networking more seriously, versus now, that has changed? 

That's a great way to put it, because I think I can sense it changing again right now. I was just posting some truly heinous things on LinkedIn, just kind of rejecting all of it wholesale because, because I do think LinkedIn is kind of bullshit in a lot of ways. I like satirizing it inside of itself. 

Also what I try to do my notes a lot, totally, yeah, because I think notes can start to have a LinkedIn vibe too. There's a lot of posturing so I try to do the opposite. 

Where do you get the confidence to be so outrageous on these very serious platforms? What made you think that that kind of weirdness was going to work?

I guess I didn't know it would but I didn’t know how to do anything else. I think it felt like no one was having any fun. That's an over exaggeration, but people were taking it really seriously. Because I think people thought that they had to be really serious with their writing. And I was just like, I don't think so. And I think that's just been my approach with writing period–seeing if I can do that, sort of combine the philosophical ideas that I do genuinely have with, like, poop jokes. It's also sort of like an insurance policy for, like, making sure I never get a real job. Burning Substack and LinkedIn helps me do that. 

There's something very Tim Robinson about your writing. 

He's a hero of mine. I'm obsessed with that show. I'm obsessed with him. People think it's just funny and dumb, but I think it's doing very complex things comedically that I could talk about forever. I just have been so seeped in it, that I think a lot of it comes out in my own work. 

Who are your other comedy icons? 

There's another dude who's pretty similar on Twitter named Eric Rahill, who, like, there's a lot of like Twitter comedians. Kyle Mooney from SNL and especially his earliest stuff with Good Neighbor. 

Another influence are The Daniels– from “Everything, Everywhere, All At Once.” They do that so well blending the two– the real deep feeling with the craziest wackadoo shit. The two work well together. They complement each other and make each side more palatable.

I want to come back to the insurance on never having a real job thing. I want to hear more about what that means for you and also want to hear the stories of how you found your two recent jobs through Substack and through showing up as yourself.

I mean it was mainly that, I’m writing it in my own way and people have been like, yeah, dude, I'll pay you. That's what I was doing when

Sari Azout

, who runs Sublime, reached out, and she was like, "hey, you know, Sublimes growing, and Substack is a big part of what we're doing, would you want to join? I weirdly have always been very into that world of PKMs and knowledge tools. And I also think that world's largely bullshit. And so I have a lot of things to say about it. 

I think the difference is I view myself not as negatively. Some of the trolling is a defense mechanism but people think it's funny, and I think it's funny too. They're both true– they're not mutually exclusive. I never want to make fun of anybody, and I really try hard not to. I think it makes fun more of myself and the stuff inside of all of us. 

Something that I really admire is that it seems like a lot of things that you make fun of are just like the systems that we all operate in. It makes me think, wait yeah, I fucking do that too. That's so stupid. 

Yeah and nobody wants to. We're all just doing it. And that's weird, you know?  

I think a lot of people feel this way about networking. We all have people we know we should reach out to and then something happens where you’re like, I don't want to seem fake or weird, or I don't want to bother them. And then you just don't. Something that I'm interested in hearing more about is how you do it anyway, even when you get that uneasy feeling, whether that's posting on LinkedIn or reaching out to new people. 

I think the way that I've found my way through that is also similar to sort of how I found my way into my voice as a writer, which is to just be very honest. I will also make sure it doesn’t look like a networking email.

I'll usually say, like, “this is probably a bad idea, and you can feel free to ignore it.” Those are things that maybe you “shouldn't do” but I think that's all shit. I think some people see that and they're like, “this guy's weird,” and then other people are like, “oh, this is kind of charming, he's honest. I feel something. I want to respond,” and it's worked more than not. 

You know the light phone? It's, like, this dumb phone that only makes calls and whatever. I really wanted it and so I reached out to them, and I was like, Hey, this is probably a really dumb idea, but I write a little newsletter, can I review your phone? And they were like, Sure. And they sent me this free phone. 

Networking is kind of like throwing a Hail Mary— thats what I call them. I remember reaching out to this guy I admired so much,

Douglas Rushkoff

. He's like a writer and podcast dude. I just like, love, love his stuff. And he responded, it was really cool. I don't think anybody's getting that many of these emails. 

Also so much of my relationship to this stuff is skewed because I come from the film world. In that world, especially as an actor, you don't email people. There's no worse sin than emailing an agent. With acting, people are like, “don't you fucking dare.” 

Yeah, it's so true. With theater too. I remember going to so many master classes where they tell you the rules. And it's really interesting, because it's not until you really chuck the rules of networking out the window, when it starts to work. 

We all think that we have to be this fake person, and then when we try to do that, it doesn't work. I think the thing that works, which is also the thing that works in writing, is being honest and being genuine. People can always tell when you are and when you aren’t. And so I like to just lead with that, even if it's awkward.

Do you find it difficult to ask for what you want, or did you at that point in your career, and how has that changed?

Yeah, I think, I think it's gotten easier because I believe in myself more now. I also think I have more credibility now. I think couching things in that, “no worries, if not” language is frowned upon, but it works for me? Again, maybe that's easier as a man, it doesn't have the baggage that it comes with for women. What do you think about that? 

Well, a lot of people will tell you to never include apologetic language in emails… never use the word sorry or just blah blah, but sometimes I am sorry or nervous or insecure. Sometimes that language helps me communicate. 

Oftentimes when I write something, even if I don't include it in the final email, I'll just type, “hey, I'm nervous right now. I don't know why, but I am sweating currently as I'm typing,” and then it'll loosen me up to write the thing. Then I can decide at the end if I want to delete that line or keep it. 

It's very similar to your take on being honest– the word I love even more is earnest. It's just rare to see someone be vulnerable in that way. So if that means you're apologizing or saying the word just, who fucking cares, right? 

Ernest is a great word. It’s like you’re naming the unsaid thing. Like, “I'm sweaty, you know?” It reminds me of the improv comedy perspective. I just want to communicate on a level that doesn't feel so fake. When you can bring yourself and the other person into a real place, that’s where the best comedy comes from.

Speaking of naming, my Substack is called

a good omen

because it’s both vague and specific enough to mean something different to everyone. What is a good omen for you?

Good omens are a rare thing for me. I think I'm always looking out for bad omens. 

Right now, I'm writing about something that's really scary and that's hard for me to write about. It's new. I've never really written about it before. It's like a new level of whatever, honesty, vulnerability, whatever. And I think I didn't realize it, but I was talking to my friend right before this, and he was like, you know, when you're scared, that's usually a good sign. And obviously that has caveats, but I think that fear is a good omen. I'm exploring the right stuff, you know, and it reminds me that, like it is hard and it can take time. And that's good. That's a good omen that I often don't even recognize as such. That framing is so key, it changes the entire experience of writing from like, terrified to like, you know, terrified in a fun way. I like that. 

Yeah, that's awesome. Oh, I'm very excited now. Okay I have a couple of quick hits, so just trying to answer these as fast as possible, like first thing that comes to your mind, okay, what's your biggest piece of tactical advice for someone trying to do something worthwhile in their lives?

Tell someone about it. Say it to someone else. 

What is one thing you would do differently in your 20s?

I think I would publish more of my writing before I was ready. It took me a long time. Maybe that is also what I'd also say to somebody. You're good enough to do that.

I love that. Assuming in this season of your life, now that you do have more credibility, you're probably getting more people reaching out to you than you are reaching out to others. What is one thing that you hate and one thing that you love when someone reaches out to you? 

I hate, I really fucking hate, and I really, really don't like, when someone I don't know asks if I want to swap recommendation on Substack. It kind of drives me crazy. It's just, it's weird. The vibe feels very off. Something that I do like is when someone compliments my work, it feels really genuine. Or when they have something really specific to say. 

Absolutely. The advice I give to people when reaching out is, it should be specific enough that it is a message only you can send and only they can receive. 

Yeah, I think, I think it's like specificity without much expectation. Yeah, if you're not expecting much, it can feel more earnest or genuine.

And then speaking of recommendations, what is one thing that you've read or seen that you are desperate to recommend? 

I mean, the main one is always I think you should leave. 

Will include a tim robinson pic

Okay, last question, then I have one little surprise ending. What is one thing you believe to be true that most people think is untrue.

Sometimes I don't know if free will is real. I think we might all be predetermined, including the illusion of free will, which I don't think is a bad thing. I do sometimes think that we have very little control over what happens. And another thing that I believe that other people just probably don't think about, is I think like everything in life is pro wrestling. I think like all of life is like us acting like pro wrestlers, like heels and faces and like taking on these identities. And it's all basically pro wrestling and like, now that's becoming more true. 

Okay what the hell I love that hot take. Ok so congrats you've won the prize. This is inspired by an NPR podcast I love. And the prize is that you can go back in time to one moment in your life, recent or childhood, and just like spend the day there, you can't change anything about it, but you can just spend some time there. What would that moment be? 

I think it would be the, like, first date I have with Lauren. We went and saw Tree of Life. It was an amazing day. And I would love to, like, just like, marinate in that– those puppy love feelings– knowing all that's coming. 

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