In this motivational monologue, the speaker confronts the common fear of failure that holds aspiring entrepreneurs back. He argues that initial failure is inevitable and the only true failure is giving up, emphasizing that the real cost of starting a business is merely feeling embarrassed. By pointing out that basic needs like shelter and food are often secured, he minimizes perceived financial risk. He then critiques the habit of seeking external approval—citing imagined judgments from a partner named Sally and deceased parents—as a major barrier to action, urging listeners to unlearn this mindset. Drawing on his own experience as a high‑achieving management consultant who felt trapped despite academic and professional accolades, he illustrates the internal conflict between external expectations and personal desire. The speaker concludes with a call to persist, even when loved ones think the venture is a mistake, and to stay committed for years, asserting that such resolve leads to success.
Chapters
Everybody here who's listening to this right now, on some level, you're like, I want to do this thing, but what if it doesn't work? Like, deep down, like, for real, I know because I've been in your seat and you just got to fucking get over it. Like, you're going to suck. Of course you're going to fail. Why would you be good? You've never done it before, right? And for somebody to hold you to a standard that you're going to win on the first shot is ridiculous. And so the idea is that you go to business school the first day you open shop and you keep getting better. And the nice thing about the game is it doesn't end. And so the only way that you actually fail is if you give up. That's literally it. And giving up translated into reality is I can't live at these standards. But most of you probably have a couch somewhere that you can live on for free. And food is also available given the way our government works. And so you can actually try at no risk because you will not be homeless and you will not starve. And so the only real cost of entrepreneurship is you feeling like a bitch. And so, but the thing is, it's like the real bitch in my mind is you not doing it because you're afraid Sally thinks about you differently. Like when you're 80, Sally's dead. When you're 80, Sally's overweight because she married some other random dude and then traveled to a different state, and you don't even see her, but you're worried about what she thinks. Also, by the way, when you're 80, your parents are dead too. So like, it's just— what a terrible existence to just have lived and not do what you want to do because you're afraid of other people. But the thing is, is that wanting other people's approval is what got you in this room. That drive. And so it's like you have to unlearn that to be able to start something new and being willing to take the risk and look stupid. Like, I was a management consultant. I had my— my dad was thrilled. I did the right thing. I graduated in 3 years. I was magna cum laude. I did, you know, I was president of 2 of the things. Like, I had all the shit. But, but then, like, we had steak. We had steak 3 times a week. We'd go get lunch. He loved it. We went to the same place. It was like awesome. I fucking wanted to kill myself. 'Cause I was like, is this it? Am I just gonna be in Baltimore for the rest of my life? Sucks. And so like, you just gotta be willing to do it. You gotta be willing to have the people you care about most think you're making a huge mistake and do it anyways. And also have them be right for not months, but years. So if you're willing to do that, you'll do great.
