In this conversational interview, Jesse and Coach "Speaker B" explore why successful founders treat rejection—whether from investors, sales prospects, or even their own children—as a form of training rather than a threat. They introduce the "presence dojo" metaphor, framing life’s challenging moments as sparring partners that help develop a state of presence. The dialogue delves into the psychological layers that surface when a founder hears "no": an initial grief over unmet expectations, a threat to self‑identity (the image of the successful entrepreneur), and deeper triggers tied to childhood wounds and unmet needs for love and approval. The speakers discuss how most founders default to a survival‑reactive stance, trying to control outcomes, whereas an orientation that views each rejection as a growth sparring match can reveal unhealed parts of themselves. Practical guidance is offered through a "rule of threes"—specific actions founders can take when facing prolonged rejection in fundraising or employee challenges. Ultimately, the conversation argues that unconditional self‑love and an orientation toward growth transform rejection into a training opportunity, reducing fear and reactivity.
Chapters
I'm working on something new and I'd like to fashion myself as this enlightened human who's done all this work on himself and whatever. And then I'm like pitching someone something and they're not paying attention and they're going to, then they say, no, no thanks. And I notice I go below the line, which sort of means I get into a state of threat or I'm questioning myself and all these things that I typically maybe coach someone else. Yeah, you just gotta accept yourself and be okay with it. But all of a sudden when you're in the game itself, there's, there's real I don't know. There's real challenges or like your psyche and your mentality. It's easy to talk about it when you're not necessarily in it every day. But I think as I've been reentering it, I'm like, oh, well, that's interesting.
Just like it's easy to say, oh, in order to grow, you got to get outside your comfort zone. But it turns out getting outside your comfort zone is quite uncomfortable.
It feels uncomfortable. I think for me, I would like to believe that I would feel different. I think I do than maybe I did 10 years ago, but I'm still like, whoa, this is pretty interesting. So, what I wanted to talk about today, just for fun, maybe rule of threes, for any entrepreneur listening out there, again, we talk a lot about fear and how do you accept your fear. And we've talked about a bunch of really—
Mm-hmm.
And you always give me this feedback like I'm too heady. I'm in my head. And I'm curious to go, Okay. Let's spend the next time, like, what are— when people find themselves in these situations, whether it's fundraising, whether it's challenging employee situations where they're for an extended period of time, they may be in like a threatening experience or they may just be in an experience that they're noticing. What are some of the things you would like pretty specifically have them do?
Well, first of all, Orientation-wise, I mean, you know this, but for audience, for me and a number of clients I work with, thinking of life as your presence dojo or a specific aspect of life like your work, building a fund, a startup, I find really valuable. And just to be clear, dojo like karate dojo, right? It's like, okay, this is the place where I train to learn to be in a state of presence. With different sparring partners, so to speak, like sparring partners, investor meeting where they ignore me and then say no, or someone I really thought was going to say yes says no.
Yep.
And what I think is so helpful about that orientation is, at least I'll just speak for myself, like I had a conversation with my 16-year-old recently and he told me, I'm not interested in college. Like, I don't want a 9-to-5 job. I think school is pointless. Like, I want to be a race car driver.
Yep. Having not ever shown any signs or interest in race cars.
Yeah, this was like a new— or it wasn't that quick. It was— I was sort of like, okay, like, well, what are you— what are you interested in? And then, yeah, then he dropped the like, I want to be a race car driver. And I felt a lot of fear. And what I really appreciate about the orientation of like life as a presence dojo is there's some part of me that's also able to be like, oh cool, like, this is triggering me. So, this is yet another life circumstance that I today can't be fully present with, present, accept, open, curious, right? I got scared. I noticed I want to control my experience, especially his experience, right? I imagine these futures where he doesn't do school, doesn't go to college, and has like a hard or crappy life. So, I noticed all that, but there's enough of me that's like, oh, this is a formidable sparring partner in my presence dojo. Right?
And just to contrast that, what's the typical way a founder goes into a sales meeting or a fundraising meeting or a parent deals with a kid saying, Something like what your son said?
Well, the typical orientation, again, if we start with like orientation is my job is to have life go a certain way.
Yeah.
Right. You know, my job is to make sure, make sure, right? Control like that my son, whatever, studies hard, you know, like whatever idea I have in my mind of what his path is supposed to be.
Right.
There's actually a good overlap, right? Or my startup child, you know, like whatever ideal path.
I need to raise this round and every time If someone says no, it's going to be painful. And I—
and they say yes, it's actually bad. You know, it's a— it's bad because it thwarts me from achieving the thing that I know with certainty is the right thing for me to achieve that will lead to the good life. And because it's thwarted, that means maybe I'll end up with the bad life. And so, I really resist it and want to control it and feel a lot of fear. And similarly, you know, Well, parenting, I think, is one of the ultimate journeys in letting go. But I think startup is too, right? Because you get pretty attached, maybe not quite as much as you're attached to your kids' outcomes, but close. And if you don't have kids, it's like the closest you get. You get pretty attached to like, this thing must be successful. So, let's come back to you, Jesse, right? Like, you have a lot of success, you've achieved a bunch. And so, you have kind of an image of yourself.
Yeah.
like an identity of yourself as this successful guy who, like, in your mind, of course, people are gonna, you know, be grateful for the privilege to get to— Get in business with me. Yeah, be in business with you and give you money that you believe you're gonna, you know, return, you know, wonderful return for them. And so, when someone says no, there's like a couple layers, right? One is the, like, That's not what I thought was going to happen, right? And so in general, we, you know, it's like, but my mind imagined this thing. And so there's a grief process that we generally resist of like, can you grieve and feel disappointed? Yeah, that like it didn't go the way you imagined it would go, right? Then there's the like, this doesn't fit with my identity of who I am, so that it's threatening to the identity, like It gets much bigger than just, oh, this one investor said no. It's like, maybe I'm wrong. Maybe I'm not really that great. And then, I think there's a deeper level. We're still just a bunch of humans playing startup or playing fun.
Right.
And so, we have all our childhood stuff of any lowercase t trauma, any ways you didn't feel fully loved or seen or appreciated also get triggered by the essentially the rejection, right? Like, we're social beings. Like, we are wired to want approval. And we perceive someone saying no to investing in our startup or our company or our fund pretty similarly to like someone rejecting you. Like, I don't want to be your friend. I don't want to be your partner. And so, it just hits us at all these layers. And again, if you're oriented toward Well, life or my startup or my fund is a dojo. I'll keep using that word, a platform for my growth. Then, a part of you is like, oh, interesting. This is showing me I still have some unhealed stuff.
Right.
Like, I think if you fully love yourself unconditionally, you're less likely to get triggered by somebody else who you perceive to not be loving you or to be rejecting you or not approving of you.
Right.
It just shows you, okay, there's still some part of myself that I haven't fully loved or integrated.
Like, it's revealing. I want to like, I want to go to, I want to double-click a bunch into these. So, the dojo thing makes sense. And I think what you said is typically people don't relate to it that way. They relate to it as like a survival and then it's like reactivity and reactivity. And so, you talk to any entrepreneur and now I'm talking to people who run funds and they're all just like, It's the worst. Raising money is the worst because you're just, you know, you're literally like, to your point, those 3 things are happening to you every day and they feel existential. But I want to ask you—
But also, you kind of have to like, in order to just be doing, putting all the energy into doing the thing, you know, you sort of have to convince yourself it's this like really awesome thing, right? And so like, I remember the feeling of like almost like this being like this little boy with this beautiful golden ball that's my toy. And I'm like, look at this. And people are like, eh, not that great. And it's like, oh, it just—
Yeah, yeah.
It's ouch. There's a real ouch to it. So I just want to acknowledge that dynamic.
