We recently had the chance to connect with Jake Leizear and have shared our conversation below.
Jake, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: Who are you learning from right now?
The past! With rapid technological and societal…movement, to say the least, there’s been a lot of appetite for DIY nostalgia. No subscriptions, no AI, just a creative and fulfilling experience that makes people feel warm. So referencing the early 2000s in promotional material, leaning heavily into analog and DIY aesthetics, and eschewing a lot of 2020s cultural references has made my material and events more noticed.
Can you briefly introduce yourself and share what makes you or your brand unique?
Jake Leizear is a Baltimore-based comedian known for his pop culture addiction, razor-sharp references, and a mischievous streak that keeps audiences coming back for thirds. He’s played Provincetown’s legendary Red Room, lit up stages at the Midwest Queer Comedy Festival, Baltimore Comedy Festival, and Uncloseted Comedy Festival, and reached the semifinals of Delmarva’s Funniest. When he’s not producing and hosting sold-out shows across Baltimore, Jake’s busy turning everyday absurdities into unforgettable punchlines.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What did you believe about yourself as a child that you no longer believe?
That all effort is created equal. Effort without direction or discretion often leads to wasted energy, while focused effort creates meaningful progress. You can spend your life pushing and banging your head against a wall, but if it’s not appropriately applied, it’s meaningless.
Is there something you miss that no one else knows about?
I really, REALLY miss those Reese’s Swoops. Those snacks from the early 2000s that were just a Pringles-shaped piece of chocolate and peanut butter. Just an absolute all timer snack.
Next, maybe we can discuss some of your foundational philosophies and views? What are the biggest lies your industry tells itself?
That luck has nothing to do with success, when it’s really the thing that DEFINES success.
Okay, we’ve made it essentially to the end. One last question before you go. Have you ever gotten what you wanted, and found it did not satisfy you?
I mean, of course. If I was ever fully satisfied by achieving goals, wouldn’t I just stop striving for them?
Contact Info:
- Website: https://jakeleizear.com
- Instagram: jake_my_day
- Twitter: jake_my_day
- Youtube: jake_my_day




