In this conversational podcast episode, Dave Kashen and an unnamed interlocutor (Speaker B) explore why founders often internalize investor rejection and how that self‑blame can become a self‑defeating loop. They break down responsibility into two layers: (1) how a founder creates the emotional experience of disappointment by attaching to outcomes, and (2) the factual fact that an investor said “no.” The dialogue stresses that true responsibility is not about blaming oneself for the rejection, but about recognizing the mental habits that generate the feeling of failure. They discuss the importance of moving from a reactive, self‑critical stance to a state of presence, curiosity, and systematic feedback. Practical tools are offered – mental models (e.g., viewing fundraising as a sales process), belief‑checking exercises, external cues (post‑its, index cards, reminders), habit‑building routines (30‑60‑day practice, “domino” attention shifts), and simple breathing techniques (4‑4 breathing) – to keep the mindset light, stay open to feedback, and avoid over‑attachment. The overall message is that taking investor rejection personally is a sign of excessive attachment; by loosening that attachment, founders can extract richer information, iterate more effectively, and maintain emotional resilience.
Chapters
I think the responsibility thing is helpful again, especially to like how you created the conditions for your upset. And for me, that's a really good one.
Yeah, there's 2 layers. Let's talk about responsibility for a second because there's 2 layers to it. One is the, how did I create this experience for myself of being disappointed, feeling this way? And that's exactly what you said, maybe like attachment to the outcome. By the way, there's this Other paradox, which we've talked about, I think, which is the less attached you are to the outcome, the easier it is to create because you just show up with a lot more fluidity when you're not attached.
Totally.
And that's a real challenge for a lot of founders. And it's like, oh, but I really want to raise the money. And so it takes real intentionality and real, I guess, courage. Like, I think there's this fear that if I let go of attachment, then I won't be as motivated and I won't be as driven and I won't drive toward it and I'll be apathetic, which is not what's— it's not true from my experience. So layer 1 is like, how did I create my experience? Okay, I had this expectation, I got attached to it, and then life didn't go— it didn't meet my expectation, right? The meeting didn't go the way I pictured it. And so again, sadness is the energy of letting go. There's no problem. It's just, it's just there's a process of letting go of that expectation. So that you can be with reality as it is. Like, that's what we mean by coming back into a state of presence. And then there's just the, I wanted them to say yes and they said no, so how curious can I be about like, what might I have done differently that might have had them say yes, if anything?
Right.
And the nuance here is people tend to blame themselves and, and say they're taking responsibility because they still are believing that it's bad that the investor said no. So they're like, they're trying to take responsibility, but really they're just like, what did I do wrong? There's like a feeling of you screwed up. Now we need to figure out what you screwed up as opposed to just, oh, I wanted them to say yes. And they said no. Like, I wonder how I might have contributed to that happening. Yep.
Yeah, that really resonates. And I think the, like, there was some order of ops we're kind of talking about, right? It's like, slow your butt, like, still yourself down. Sense what you might be feeling, actually feel the feeling, start to look for ways that your stories are sort of, you know, maybe not true, this responsibility piece. And then, and only then, can you get curious about what you could have learned or done differently. And the reason I'm saying this, by the way, is for myself, really. Because what I do is before I get to even one level down, I'm like, okay, reflect, feedback. What could we have done differently? What are we learning? Maybe the format's not right. Maybe we have to change the way this is structured. Like, And I find myself in that pattern a ton, which is I don't even get to this whole bottom. Like, I don't feel that. I'm just like, ooh, let me adjust the— let me try to find the answer. And I think in sales in particular, it can get very tempting to keep— it is good in sales to iterate, obviously. But I think when you're iterating from that place, you can end up in very bizarre situations or just situations where you're not really learning the thing you need to learn. Yeah.
Yeah, it's like a reactive pattern is what I hear you saying, right? It's just like, oh, I don't want to feel this. Okay, I gotta just figure out what to do so I never feel this again. And the insights you have are— I think what I'm hearing are not nearly as useful or rich as when you shift to a state of presence and you're truly curious about what you could have done differently.
Yeah, I think it's typically when, you know, you're You start spinning essentially. You're like, well, I could do this differently, but I don't want to do that. I want to do this instead, and blah, blah, blah, blah. And then, at least for me, you're not really— you're just playing this game with yourself and you're not actually figuring out the thing that you're hearing. And the interesting thing about selling in general is, man, selling is such an amazing source of feedback, whether it's selling to companies and enterprise, whether it's fundraising. It's a very rich source of information. That oftentimes I think we don't take advantage of because we just get so stuck in that, in that place.
Yeah. One thought I just had when you mentioned selling is like, there's sort of more obvious insights that might come like, oh, this, you know, the way we pitched it, you know, wasn't as clear. We should have said this or that. But then there's like, if you really get curious, you might start asking things like, well, what is even my relationship to fundraising? Right? Like, what's my— oh, fundraising is hard and—
Means to an end. Yeah.
Scary. Or investors are pariahs, but it's like a— what's it called? Like a necessary evil. And those mindsets, even before any strategy, any way you communicate, will affect how you show up and how it goes. So, that's what I like about the deeper curiosity. I just did this retreat in Sun Valley and we did an exercise around that. Fundraising is dot, dot, dot. Hiring is, building a startup is, and really had people reflect, like, what is my knee-jerk, just first thing that comes to mind? What are my beliefs about these different aspects of building the company? And how are those beliefs impacting how I show up and how I perform? And it was really insightful for people to realize just how much those beliefs were shaping their experience. And because we're on the topic of fundraising, one of the participants was like, oh, that's interesting. I love sales. I love sales and I hate fundraising. And we're like, oh, that's interesting. You know, like, I love sales because I'm like giving this buyer like an opportunity to like get real something they really value. And we're like, well, how, you know, how is that different from fundraising? And, you know, they're like, oh, wow. Yeah, I guess it could be that too.
Yeah.
And, and, you know, there's a way in which if you think of it more that way, it's like, okay, like if a buyer doesn't buy because it's not a good fit, it's not, you know, sometimes we take that personally too, but it's a little easier to be like, oh yeah, it's just not a good fit, right? Or like, yeah, again, like all these metaphors, some people—
It's almost like when you— fundraising has just a higher chance that you make it about yourself, basically.
Yeah. And I mean, people do with sales too, but like, right, for whatever reason, like if you're selling the whole company, not, you know what I mean? Like you're selling like a stake in the company.
Yeah.
It feels more like, yeah, more personal.
The, the, the idea of, of the dojo, how do you, how do you remind yourself of that? Or how do you keep it present? Because, because again, these conversations on a podcast on Friday afternoon are great. Yeah. Next week, You got to go back in.
And so, I really resonate with the idea of running lots of experiments. And so, instead of like, oh, there's one answer, you know, like, I invite people like to run a number of experiments around your question, like, how do I keep this front of mind? So, there's a, you know, there's tons of structures that we can use. Here's what I'd say. I would not rely on your memory.
Right.
Right? It's like the time where you most need to remember it is usually the time where it's least accessible in your memory. So, you know, whether it's a Post-it note on your laptop or a printout that you keep, you know, on your desk or a little statue of— like, I have a little Buddha statue I'm looking at, you know, I'm like, you know, or like something like an external cue. A calendar reminder, an app reminder. Some people will like set up like a Google Sheet and—
Yeah. Once upon a time you had me keep index cards in my back pocket and pull them out before a meeting. Maybe I'll try that again.
That's a great example, right? Like some physical structure or some digital structure that you don't have to rely on your memory. Like it's gonna pop up or you're gonna see it. And I do, you know, the good news is there is a compounding effect to practice. So, I do find, like they say, right? You do something for 30 to 60 days in a row, it becomes more of a habit. So, I have found, and many, many founders I've worked with have found that over time, if you practice paying attention to where am I, which is really like the domino habit, right? Like, first thing is just to notice.
Right.
dominoes of like shifting over time, you get— yeah, it gets easier. Like it becomes more habitual for your, you know, to put attention on that.
Yeah. 2 that I've been playing with, with medium degrees of success. One is this, that there's like the Ram Dass line, and this too, where he kind of says no matter what you're experiencing, just like it's, it's part of the universe or God, like, and this too. And like whatever it is, that's been one. And then another one that I've been playing with has been like, this is kind of a crazy one, but it's like, if you imagine like God, universe, you pick your, your source, whatever, like existence, pick your favorite word. I'm like, I have this idea of this thing I want to do. And every meeting I take is, is someone like, it's like God being like, well, what about, don't, like, you should, it's like a, it's like a piece of feedback to shape the idea to make it better or to like make it more aligned to me actually. Which a lot of the conversations I've been having, they sometimes feel like alignment conversations, not yes or no feedback conversations. So I don't know, those— I'm not—
Almost like the universe is mirroring.
I was gonna say, like, each universe is mirroring that. It's the same person just giving me different feedback and guiding me along a path for where this ultimately ought to be and end up. And because a lot of conversations I've had have been rich in feedback in some sense of like, well, what about this way? Have you thought about it this way or whatever? So anyway. Those have just been 2 I've been trying.
Yeah. And what's cool about that is the less attached you are to the outcome, probably the more interesting information you'll get, right?
Totally. Totally.
You'd be more open to hear someone give you feedback or you'd be more curious, like genuinely curious about like, oh, what? So, you're saying no. What makes it not a fit for you, right? Versus if you're just like, oh, shit, you're kind of probably not listening.
And especially like, My thing I'm working on is very Midwest-centric, and I've noticed when I'm staying in a good zone, someone's like, oh, let me actually introduce you. This person would be really good because they'll care a lot about this. I don't care about this, but that person will care. And I'm like, oh, okay. If I do this constantly, I keep getting 3 intros to people who are more likely to care about it. This whole process is going to go back. And in New York, that happened quite a few times. And it's super interesting that there's a lot of big dogs who are from the Midwest or from St. Louis, actually, in particular.
Oh, wow.
And it's like, oh, yeah, those are conversations that'll will be more fruitful.
So, I don't want to tell the whole parable of the Chinese farmer, but I really like the— look it up if you're interested. But I really like the conclusion of it, which is sort of like, good news, bad news, who knows, right? I find that really helpful because my mind just wants to label like, oh, that's bad. That's good. That's bad. That's good. But I'm like, would it have been better if they invested? Like maybe, like you said, maybe this intro will be more valuable or maybe that would have been a pain in my You know, pain in my ass, or like, like just to hold much more lightly my mind's idea of what's good and bad so that I can be more in flow with just life as it is.
Yeah.
Um, there's something we skipped— I skipped over that's like the simplest of all of this, which is just take a deep breath.
Hmm. Right?
And even more so would be like, you know, 4x4 breathing where you breathe in, right? In for 4 seconds, out for 4 seconds. You do that 4 times, about a 30-second reset. Sometimes just that, like, maybe you still have back-to-back meetings, maybe you don't have the 15 minutes in between. Even just the difference of like starting, you know, or giving yourself 30 seconds between every meeting, take a few deep breaths, will make like a huge difference. And that also could be a trigger to then Okay, what am I feeling? Right? So I just, I want to, I'd feel remiss if I didn't come back to like the most basic of shift moves.
It's just simplicity on the other side of complexity. Just, just breathe, baby. Notice your breath and keep breathing.
