Office Hours: I'm a comedian and co-host the new HubSpot podcast, The Shake up. I previously built GTM at Patreon.Featured

Hello hello! My name is Alexis Gay, I’m a comedian and podcast host, and I used to work in tech. On my podcast, Non-Technical, I interview influential leaders from tech and business and beyond about everything *except* their resumes. I also co-host the new HubSpot podcast, The Shake Up, where venture capitalist Brianne Kimmel and I explore the business decisions that dared to be different. You can find my jokes on videos on Twitter and Instagram.

Prior to all that, I built out GTM business operations and ran Creator Partnerships at Patreon. Before Patreon, I spent time at Twilio, and a few NYC startups.

Ask me anything about podcasting, interviewing, growing your audience, content creation, partnerships, managing a team, and more!

Thanks so much for joining us @alexisgay!Elphas – please ask @alexisgay your questions before Friday, September 3rd. @alexisgay may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
Hi Alexis, you have such interesting and varied work experience. Did you ever make a big career shift (going from one position to another), where you felt a little out of your league? If so, how did you deal with it? Asking for a friend ;-D Thanks in advance and will give your podcast a listen!
Hi I do standup and just fangirling that you're HERE!! I guess I'm curious how you as a comedian can balance punching up at systems of dehumanization and exploitation in tech (which you poke fun at) while also profiting from those tech companies supporting your work? How do you find the place to stand within the system while also critiquing it? I ask because it's a balance we all have to strike, not just you, and think humor is a unique tool you can use to deconstruct systems of oppression and make things better for everyone. TIA!
COOL! I love that you have brought your whole self into your work, the creative and the technical. I spent so long touring with my band as a primary endeavor that my resume sort of sags. Now I'm doing the work to finally finish that bachelors degree in business! I'd love to hear any wisdom around using your creative side to boost your career options. KUDOS TO YOU! It's inspiring to all of us. :-)
Sags?! Emily! You were in a band!!!! OKAY let’s get into it. I do have some thoughts on this—I’m going to come from the perspective of using your creative experience to enhance your professional life outside of the more typical “use your art degree to do graphic design” or “put your musicianship to use writing jingles” path. Not because there is anything wrong with that path, but it’s not mine, I’m assuming you’ve already considered it, and I want to speak to my own experience.I grew up acting as a hobby. The first time I was on stage, I was 5 years old and in my school’s Christmas pageant. Even though I threw a HUGE fit from stage fright right before the show, the second my feet touched the stage I was hooked. I grew up getting my hands on whatever acting opportunities I could while still balancing the fact that I loved getting good grades (the only thing cooler than an academic nerd is a COMBO academic nerd + theatre nerd… what I’m saying is, I was extremely popular ;) I promise this is going somewhere!!!I kept acting + kept caring a lot about school, which landed me at NYU getting a degree in Individualized Study at Gallatin, and subsequently getting a job at a new tech startup that I thought would keep me intellectually stimulated and give me the flexibility to figure out the whole being-an-actress thing. When I first started at that company, I was embarrassed about my acting background, even though I had internships and a business minor under my belt. I was fearful that my new coworkers would look at my creative experience and be judgy. I thought they’d reduce me to all the negative things people think about actors. I didn’t even tell my new work best friend. (I remember literally ~~confessing~~ it to her months later in line for salads near Madison Square Park.)I carried this attitude with me for YEARS. That my acting background, my creative side, and later my comedy hobby were to be kept AWAY from the office, away from the place where I needed to be “taken seriously” as a professional.I promised you this was going somewhere… we’ve arrived: I didn’t start really feeling like I was thriving in my career until I did a COMPLETE and total 180 on the narrative I was telling myself about my creativity.After working in a few more tech jobs, I found myself wanting a company that was more aligned to my passions (creative stuff!!!). I found Patreon, a platform that lets artists and creators run their own membership businesses. SO, FINALLY, SOMEHOW, I was able to take all that fluffy, silly, creative stuff that I thought was holding me back from being an Important Business Development Person and completely reframed it to this amazing, creator-first company as “this is actually a tremendous value-ADD to my candidacy.” I was basically like, “Look, Patreon, I can build operations, I can close deals, AND I can sit across from a creator and say, I know how this feels.” I didn’t hide away from who I was. I didn’t try to keep it a secret. I found a place and a position that valued my skillset—the whole skillset.But I’m not saying, “oh it’s easy, just find a good company lol” to you. What I’m suggesting is that you, like I did, ask yourself “what am I currently telling myself is a detractor from my hireability that is actually a unique and awesome component to it? What do I have that nobody else does?” and then think about where that special sauce might be valued. I’m so excited for you. It’s cool as hell to go back and get your degree, and it’s cool as hell to be in a band. I am so grateful to you for asking this question and letting me share my experience. Good luck. You got this
Hi Alexis, it seems that you are using all parts of your creative and technical background at your current position with HubSpot. I have my own podcast "Your Spectacular Life" and would love tips to grow my audience. Also, if there were three main points that you like to discuss with a guest on an episode, what would they be? Thanks.
Hi Jodi! I’m actually self-employed :) I contract with HubSpot to co-host The Shake Up. ANYWAY, first of all—congrats on producing 28 episodes of your podcast! Producing just one episode is hard, I applaud you for keeping up with it. One thing I think is always valuable for online content is consistency—it looks like your episodes come out roughly every two weeks, more or less? I would see if you could really stick to that commitment so that your audience comes to anticipate and look forward to a new episode from you every two weeks (or whatever cadence you choose!). I would also consider creating some promo content for each episode and sharing it with your guests to share on their channels. I do this with my show. Each week, I create an Audiogram using Descript (, and tweet it out from @yayalexisgay tagging the guest. Almost every time, my guest shares the little snippet with their audience. I make sure it’s a fun clip and looks/sounds professional. Three main points to discuss with a guest….. hmmm… it really depends on the show! I always, always, ALWAYS want my guest to look, sound, and feel amazing while creating a fun show for my audience, so I try to ask specific questions they’ve never been asked before. I also like knowing the little things… I’m not sure why, just something that makes me feel connected to people as humans!BEST OF LUCK!
Thanks so much, Alexis. I appreciate the suggestions. And kudos for you for getting this great gig with HubSpot.
And, the Descript program looks fabulous. Thanks for that suggestion as well.
Hi @alexisgay, thanks for doing this. I'm a huge fan of your work!I was wondering if you had any good GTM playbooks or templates? Thanks!
Hi Alexis! How do you balance your work as an artist with your work as a professional? Im a comedian as well and i was working as a bartender last year, but now im starting a job in tech and I'm not sure what to expect. Thank you - Sam
Hi Sam! Thanks for the question. Simply put, there are only so many hours in a day!!! And I’ve always found it challenging to fill them in a way that leaves me feeling like I truly accomplished everything I wanted to by the time my head hits the pillow.I worked in tech for seven years before I left my full-time role in December to be self-employed as a comedian and podcaster. For a long time, working “business hours” in tech and “after hours” as a comedian was enough for me. I would run to open mics or improv practice after I finished up my workday, write jokes before my first meeting, or film and edit videos on the weekends. For a long time (years!), this was the right balance for me. During the day, I found my work managing a team at Patreon incredibly fulfilling. My role grew and evolved and expanded in my three years and I *loved* it. And then, over time, the balance between my work time and my comedy time started to feel less right. I felt pulled to spend MORE time on comedy and LESS time “at work.” But unfortunately, as a manager of a team of 7 (!!) people, I knew it was not okay to give any less than 100% effort in my “day job.” It was honestly really hard to admit that I no longer wanted the thing I had worked so hard for, and had come to love so much. Ultimately, I left my tech job in December to do my comedy and podcast full-time and I am so grateful I did.I think it’s a falsehood we tell ourselves and each other that “work/life balance” is an end-state goal that will always look the same for us. For me, it has evolved over time and I anticipate it continuing to do so. Even now, I struggle in trying to figure out how much of my time should be spent on purely creative pursuits like writing and creating videos, and how much time I should spend on more business-y stuff like managing my inbox and negotiating sponsor deals. I think, given that you’re about to start your first role, it’s hard to say “what to expect.” My advice to you—if you’d like to hear it—is to be curious about and open to how it feels when you get there instead of trying to anticipate and plan for what you THINK it will feel like. I say this because you might surprise yourself (I have) and what you want/need might change over time (mine did).Wishing you all the best!
👋Just want to say hi and share how much I've loved watching your videos (been following for a long time now!)
Thank you SO MUCH!!! I don't think I'll ever get tired of hearing that. I appreciate it from the bottom of my heart. Making people laugh brings me more joy than I ever thought possible. Thank you so much for your support.
Hey, that's so cool! Were you a comedian before you transitioned into tech, vice versa, or was your experience something else entirely?
Ahoy! Thanks! I grew up acting as a hobby (though I wanted it to be my career). But after college, I went into tech in NYC. I moved to San Francisco after 3 years and started doing comedy on the side when I got there…… and then…. well, now it’s my full-time gig! Thank you for the question :)