In this Entspresso episode, host Evan Carmichael opens with a short Tina Fey clip in which she emphasizes the importance of trusting one’s instincts when writing and producing, noting that regret only comes when she fails to question a story point. Evan and a co‑host (Speaker B) expand on the theme, sharing personal anecdotes about second‑guessing themselves, listening to others, and diluting their authentic vision. They argue that true leadership and branding require staying true to one’s gut, even if it alienates some. Evan recounts several "crazy" ventures—creating entrepreneur trading cards, the Toronto Dance Salsa project, and various YouTube series—describing how he ignored skeptics, followed his instincts, raised over $100,000 for charity, and learned to view failures as learning opportunities rather than setbacks. The conversation stresses a growth‑mindset: act quickly on ideas, fail fast, iterate, and keep the next crazy project in the pipeline. The tone is conversational, motivational, and enthusiastic, encouraging viewers to trust their instincts, act on bold ideas, and not be swayed by external opinions.
Chapters
Bum bum bum ba dum bum bum bum ba dum bum bum bum bum bum. Good morning, Believe Nation!
Today's message is: Trust your instincts. Over to you, Tina Fey.
I've learned to, and continue to try to learn to, trust my own instincts when it comes to writing and also producing sometimes. The only times I have regret about something we've done is if I didn't kind of follow my instinct to at least ask a question about a story point or something we were doing.
So what do you think?
I think it was a really short clip, but there was so much there. And maybe I'm reading more into what she's saying, you know, from my own experience. But like her, the time where I'm like, "Oh gosh, I wish I hadn't done that," is when I second-guessed myself. It's when I listened to other people. It's when I made an effort to try and be more politically correct, so to speak. I'm gonna try and consider more candidates even though I found a candidate for employment that I really think is great. I'm gonna try and be more open to listen to everyone's feedback even though in my heart I've already made up my mind on what I wanna do. And then it waters down what I know to be correct only because when you're making a decision, when you're running a business, when you're hiring people, when you're marketing, when you're doing anything, it's an expression of you. People are buying into who you are. As the owner, as the brand. And every time you take in all those other things, you're just watering down who you really are. Who you really are, people are gonna love or they're gonna hate, and that's fine. But if you just water it down with all these other things, you're not trusting your instincts. Ah man, it's just— the times that I regret are when I'm listening to other people even though I know what I should do.
For me, I think it's about when you have those crazy ideas, to do something about it. As entrepreneurs, we come up with the crazy ideas, right? Like, "I wanna try this!" And then the next morning you wake up and you don't have the courage anymore to do it because of whatever. You don't believe you have the skills or capabilities, or you're worried about what people are gonna think about you. You've come up with all these reasons why you can't go and do it. And more and more and more, when I come up with a crazy idea, I just do it. Just the next morning, wake up and find a way to do it. I was up till 3 in the morning last night thinking about Toronto Dance Salsa and thinking about family, it's our one word, and thinking about what smell is family. And I walked in here asking these guys, "What does family smell like?" Cinnamon and apples. Right? You ask that question to most people and they'll be like, "Are you crazy? Like, you're at salsa school, what does that have to do with cinnamon and apples?" but it's relevant and it's important. It's something I want to test out and try. Maybe it doesn't work, but more often than not, it does work, even though the people around you think that might be crazy. And so, trust your instincts for me is when you have those crazy ideas, you owe it to yourself to go out and just try it because you don't want to live with regret, then like a year later thinking, "Ah, I really wish I gave it my shot." Can I share some stories?
How about you?
Okay, yeah, go.
You can cut this out.
No, keep it, keep it. Okay.
So I remember a few years ago Evan came to our mastermind group and he said that he wanted to create entrepreneur trading cards. And you came to the group and you said, "I want to create a baseball card of famous entrepreneurs." And I was like, "That is crazy. That is ridiculous. Why would you spend money and time on it? Why would you do this?" And you know, today he called me the little man, and that's fine. But I remember at the time thinking, why? Like, this makes no sense. And you proceeded with it, you went through with it. It's like one of the coolest things I've seen someone do because it makes no sense in my very kind of logical, rational mind why any of that stuff would connect. But Evan didn't listen to me, you didn't listen to the other people who questioned why it would happen, and you just ran ahead with it. And you found like baseball card companies and you got licenses for artwork and you, You lined up like all these cool people, and it became one of the things that I'm like most proud of you doing, which was a total passion play which had nothing to do with business at all. And I learned from that, that like Evan's tenacity to just be like, "Hey, I'm doing this," and then run off and do it. I've learned from that, and personally I work to try and instill a little bit of that myself.
That was a fun project, and you know, the business side of it, it put me on the radar of of Tony Hsieh from Zappos and Tim Ferriss and Seth Godin, Mike Arrington, and a bunch of big power players in business. And we raised over $100,000 for charity. All the proceeds of those cards went to charity for entrepreneurs in Africa getting started. And so that helped raise— we just crossed over $100,000. So it's pretty cool.
Okay, that all makes sense now. But years ago, I did not— I did not see it.
Right. And you know what, like, to the point, I didn't know either. Right? Like, it's always— hindsight is always 20/20. I can look back and say all the benefits that I got from it, but when I got into it, I said, "I'm gonna do this crazy thing and create entrepreneur trading cards, and I don't care who doesn't like it. I'm just gonna do it and trust that it's gonna work out." That's just my mantra now. It's just, you have a crazy idea, you go and you try it out.
What do you do when everyone around you thinks that your crazy idea is crazy? And when your instincts— have let you down in the past? What do you do?
They almost never. I don't know, like, so first of all, I'm used to having everybody around me think that I'm crazy for Toronto Dance Salsa, for my business. I'm the crazy one.
Guys don't even know the half of it.
I'm the crazy one. And I'm used to the weird looks, and I'm used to the like, that makes no sense for our business. I'm used to that, we're gonna lose money on this. I think part of being the boss is I get to decide what I do. And I never force people to come along. It's like, I am an army of one. I will will this into existence. I will do this myself. It's going to happen. I'm going to make it happen. Come on board if you want. If not, cool. I'm going to make it happen regardless, because I don't— I hate pulling people alongside who don't want to be—
they don't believe—
who have to be like convinced to do it.
What do you do if you're at a point in your career where you've tried a few things and they just didn't go well and you're lacking that confidence? That's what I mean. When you believe so strongly in something, and it's your fourth, you know, idea, or it's your fifth business, and everything kind of just went this way, and everyone's like, "You're crazy." How do you push through?
I think, I mean, I may be the crazy one. I may be the wild card. Maybe I'm not enough of a pragmatist. I think for me, I have a really short memory. Like, I'm an optimist. If something goes wrong, I learn from it, and I see that as a positive experience, not like, 'Oh, I failed, so I'm gonna fail at everything else. I'm never gonna take my shot again.' I tried it, it didn't work, so I pivot and do something else. Like, the cards were great, and then, and then I grew tired of making them, and so I stopped. Like, I haven't done a second run. Like, that could have been like 10 series. I just moved on to something else. Like, I know I'm used to trying a lot of different stuff and not have everything stick. Fail fast, I guess. I guess, like, we'll try a million different things on the YouTube channel. We've tried a lot of different series. Some of them I like, some of them I like at a time, and then we rotated and shifted it out and done other things. My channel's evolved. If you go back and look at the channel from the start to where it is now, done a lot of different things, uh, but I don't see those other videos as failures. I learned through it, I got better, and I'm excited about the next thing. Like, there's always the next thing. Next— I'm addicted to growth and innovation and crazy ideas. I need to always have something crazy going on for me to feel fulfilled and that I'm having an impact. And so I'm used to the crazy faces and looks. I think once you show that you can get through it, then you— I'm used to it, so I don't care. Your opinion— have you done what I want to do? No. So your opinion is meaningless to me. So I'm going to go and do it and move on.
I love it. I love it.
Longest espresso ever.
This guy's getting me so fired up. So the question of the day today is: of this rant, what was your favorite part?
Favorite part of the rant? Leave in the comments, we'll join the discussion. Thank you so much for watching, have an amazing day, continue to believe, and we'll see you again tomorrow morning for another shot of espresso. I wake up every morning, espresso keep me going.
