The Gift of the Black Sheep: Belonging by Being Yourself with Jake Knight
Jake Knight
Contact: jake@joinenclave.com
Jake Knight is the co-founder of Enclave, a highly curated community for Rising Gen peers from Ultra High Net Worth families. As a Next Gen himself, Jake is passionate about empowering others to navigate the unique challenges and opportunities that come with wealth, balancing identity, purpose, and connection in a world where wealth holders are often both idolized and misunderstood.
Through Enclave, he fosters authentic relationships, meaningful dialogue, and personal growth rooted in kindness, empathy, and vulnerability. Jake believes money is an amplifier of our values, insecurities, and potential, and that the judgment or isolation often experienced within wealthy families can disrupt identity and fulfillment. His mission is to create spaces for honest conversations about the experience of wealth and to help others build lives of contribution and authenticity.
Driven by radical responsibility and self-exploration, Jake invites others to lean in, embrace life’s natural tensions, and discover what’s truly possible when we lead with openness, curiosity, and generosity.
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Kirby Rosplock
Welcome to the Tamarind Learning podcast. I'm your host, Dr. Kirby Rosplock. And today we are talking about a subject that is near and dear to my heart because it's something that at times I've related to personally. But we have a guest today that I just think is the bomb. Jake Knight is here with us, and he's going to tell us a lot more about his own personal journey and his experience in growing up and maybe feeling like an outsider at times. We're going to talk a little bit about what it feels like to be the black sheep in the family or the outsider. Sometimes looking in. And maybe sometimes you don't always know that you are that outsider looking in and what it feels like to discover or find out during your own personal journey and how maybe you might find out somewhere along the way that maybe you are a little bit different. Maybe you don't exactly fit in with all your other family members. So Jake, welcome to the Tamarind Learning podcast today.
Jake Knight
Kirby, thanks for having me. I'm excited to have a great conversation.
Kirby Rosplock
So this is a topic, like I said, near and dear to my heart, because I myself at times, have felt like maybe I am dancing to a different drummer out there. And I'd love to hear a little bit more about your personal journey. In your background, what in your personal history led you down this path to discover that maybe you were different?
Jake Knight
Yeah, it's a great question. It gave me time to reflect even on when I maybe started first having those thoughts or recognition. And I reflected back. My sister actually sent me a picture of me the other day, and I was in kindergarten. And that's probably like, there's many ways to feel like a black sheep, maybe both inside of a family system, inside of a culture. And that was maybe the first time I felt quite different. I was what back then was called a husky kid or a chubby kid. And then on top of that, when I went to kindergarten, they realized my eyesight wasn't very good. And back then, the glasses were pretty thick and not very cool. And so that was probably my first recognition of understanding maybe feeling like a bit of an outsider, both within my family. My family is very healthy and slender, and none of my siblings had glasses, as well as maybe within my class of feeling a little bit different. And then as it relates to our conversation and probably this audience, another pivot point for me was third or fourth grade. I started getting teased about being wealthy or being a rich kid.
Jake Knight
And so that was another black sheep moment moment of like, wait, there's something different here that I don't understand. What's different yet, of course, as I've went through my journey, I can now understand. And and look back. That was, one, a time developmentally when you start becoming more aware of comparison. And two, my dad's trucking company was exploding. And so So it was a very visual business with our last name on the trucks. And so people couldn't escape it. And so it was always something that brought judgment. And then maybe fast forward through adult years and things, I think I was always a very compliant child. I learned there was safety in compliance. And so as I became an adult and started having my own voice and getting more comfortable with sharing my ideas, I quickly recognized that they were unique and different, both culturally, sometimes different than the religion I was raised in and also different than maybe the way my family or my family system system thought about things.
Kirby Rosplock
So you're sharing with me a lot of ideas of where you showed up differently. So both how you looked and maybe both how you related socially, right? So people could see that your family had means, and maybe that made you stand out and look differently. And then maybe some of your views, maybe how you thought was different, even from your own family tribe, right? So how did that tension of knowing that you were literally different, peeling apart from where your family was and then who you were becoming, how did that tension between, Oh, should I be trying to come back into the fold and get along, go along, get along, just mask up and just pretend like I'm really one of them, just be with my family and put on that mask, what was that tension like versus saying, No, I got to be true to myself. I got to just honor the fact that I'm not. I'm not like the rest of my family? What was that like?
Jake Knight
Well, there's a lot of it. There is tension, I feel like is an accurate term and something that I've always lived with. And I think even as I've matured and done a lot of personal development work, I still sit with that tension. I think now I'm getting more comfortable in sitting in that gray area of honoring the family I come from, honoring their beliefs or patterns, respecting everyone in their own unique way, while also being true to myself and having the courage to say, It's okay for me to be different, and I can be respectful and different. I don't need to be disrespectful in any way. But there's been a lifetime of tension there. And, Kirby, I've shared with you in the past, but maybe where the biggest tension point in my life was got married young, to my high school sweetheart, started a family young, went to work young. And really, I always say I was in a pressure cooker and was really trying to conform to what I thought it meant to be successful and living up to the big shadow that my father cast, even though he didn't intentionally cast it.
Jake Knight
It's just those are the messages I received in my childhood, and I was so bound and determined to prove everyone wrong. And so as I went through that process, one, I learned there was nothing I was going to do that was going to prove. Haters hate people who love and appreciate or will see the good. So there was nothing I was going to do to prove, but it was self-destruct. Destructive. And I got to a point where I was... After having my daughter, she would have been around two years old, I really suffered from a deep, dark depression. And my world was just caving in. Thankfully, because my natural way of doing things, I got into action. I got myself into treatment. And that really opened up this lifelong process of self-exploration and decoupling what society or what family might need from me and what's actually true to me. And I would say that work continues. And as part of that process, I think, especially in my 20s and 30s, I felt uncomfortable with my uniqueness. And through this self-development process, I'm actually seeing the power in being black sheep, whatever term we want to use it, disrupter, challenger of the status quo.
Jake Knight
I'm now starting to embrace and recognize the positive aspects of that and still learning to tune in and be comfortable with that tension.
Kirby Rosplock
Well, I honestly see more what I would call black sheep becoming family champions because they're a galvanizer. They're a catalyst. They tend to be change agents. So I actually think many of the black sheep of the family are the ones that end up being the biggest growth agents within family systems. They're the ones that tend to create a shift in power balance, and they oftentimes are the ones who speak truth where everyone else falls back into the recesses of power, in the voids of power. They don't want to expose themselves. And so the black sheep are the ones that sometimes fall on the sword, and they literally are the ones that either stir the pot or at least create the energy to break open systems that definitely need that opportunity to bring voice where there's oftentimes no voice. And so I have to say how much courage It's a message, right? I don't know that black sheep often get the attention in the right way. I think today's segment is really talking about the positives, the gift of being the black sheep And the fact that we don't talk enough of the belonging by being yourself and the power of the positive side of being the Black sheep, which is really, I think, the emphasis of our conversation today versus the stigma.
Kirby Rosplock
I think we have such a negative stigma, and I think that's what we're trying to maybe write the ship of our discussion today. Tell me a little bit more going back to that turning point and And thank you for being so vulnerable and telling us about that dark part of your life, because so many people don't go there. So thank you for sharing that. But coming out of that incredibly dark period, can you How did you just talk about the shift and the healing that happened coming out of that and how that internal struggle actually helped you maybe bridge relationships and maybe have a new relationship with others that you didn't have prior, maybe after? Yeah. Did it shift? Did it shift those relationships?
Jake Knight
Yeah. I think a lot shifted, right? I mean, when I was in a really tough spot. And so coming out of that, when you disengage with the day-to-day life and you're surrounded by others who are also in a really tough spot, right? I was in a treatment inpatient with people who are suffering from addiction, alcohol, crippling anxiety, depression, suicidal ideation, all of those things. And so that one, there was power in that, in sitting in a room and recognizing, okay, I'm not the only one going through this. And so it created a safe space to really learn to be vulnerable and maybe start sharing parts of me that ultimately were out of alignment. I view depression as just a different form of addiction. It's like internalized confusion and self-loathing. Coming out of that, it really gave me the opportunity to play with questions in a much deeper, authentic way. I moved through a process where prior to that, I was raised quite religious. And so as a result of that, I ended up leaving the church that I was raised in. And there's a lot of stigma around that. But for me, it was quite simple.
Jake Knight
It was just, do I feel better or worse after church? And I felt more shame, more guilt, more not enoughness after. And that was my experience, right? I think church can be a wonderful thing for many. And it also helped me decouple and understand that being religious can be different than being spiritual. It allowed me space to explore the more spiritual sides in my own unique way and having some freedom to do that. The other big takeaway for me, Kirby, was I think part of part of what happened that I was struggling with at the time was I was becoming aware that I was replicating some patterns that didn't necessarily feel good to me as a child. And so I was on the road all the time. I was a total workaholic. I was bringing work home. I was anxious to leave dinner so that I could prepare for the next work day, all of these things. I had experienced that because I watched my dad build this company and take it public. And that, too, was an interesting piece. From that, I gained a lot of empathy and compassion for my dad, of seeing the pulls on his time and the pressure and all the responsibility and the intensity required at work, and that there wasn't just an easy switch to turn that off.
Jake Knight
And so from all of that, I think one of the biggest things would just be that it helped me recommit to get true to myself and really get anchored in on being a good father, a good husband, a good son, brother, friend, And to do that, I needed to be more authentic. All of those masks, all of those structures I had built up to project out that everything was okay, weren't actually creating vulnerability or depth in those relationships. And so that's been my life's greatest work, really, is tuning in to myself so that I can better tune in to others and especially better tune in to my children.
Kirby Rosplock
And so literally, you flipped the switch from being on the outside to now shifting to a focus of building a community all to help all those that might feel like they're on the outside, right? So your whole life has been about dedicating to help the black sheep and anyone who's feeling being lost, isolated, alone, or just needing to find connection and community. So tell us more about how that has shifted in your world and what that looks like and how that has all synthesized around from where you come from to where you are today.
Jake Knight
Yeah. Well, it certainly wasn't a planned path. As much of these things are, they just they happen, and they make a lot of sense when we look back, but I could have never, never predicted. And it's actually interesting. The idea of Enclave and having connection and community around this experience of wealth, growing up as a next Gen or rising Gen within a financially successful family. This idea had been brewing in the back of my head for a long time. And yet when I finally took action on it, there was many reasons why I wasn't ready to build this five years ago, 10 years ago, 15 years ago. And so you really named it, Kirby. It's all about we find a lot of the members who join Enclave, whatever terminology they identify with, they're very much seekers. They're typically family champion. Some of them very much feel like black sheep or scapegoats or outcasts. Some of that comes from a place of high achievement. So the high achievement and the personal development and the emotional maturity that they have learned and developed actually can make them an outsider to the homeostasis of the family system. And others, being the black sheep, might be that they've really struggled through life, right?
Jake Knight
Whether it be with engaging with their contribution in the world or struggling with addiction or mental health challenges. And yet, regardless, whether it's viewed as overproducing or underproducing, I hate to even use those labels, everyone has a common interest of not feeling isolated and being able to let their guard down and come into a space where they don't have to withhold what their name is or that their dad or grandpa or great grandpa or grandma founded XYZ Company. And because of that, those things actually aren't talked about often. Nobody's posturing around their family business or how much financial success they've maybe had. It's more around personal development and how do we do this well. And so it's really a result of taking my life and my experiences and the things that I've exposure and wanting to build something that I wish I had access to 15 years ago, as well as what I want to have access to for the next 15 years to continue my own personal development.
Kirby Rosplock
Tell us a little bit more about what members get out of being part of Enclave.
Jake Knight
Yeah, everyone comes for a different reason. There's some practical tactical, where people get to join Zoom calls with experts or with other group members. Some come who have never talked about their wealth. They've never reconciled their identity. And so usually something has sparked it. So we have a member who's one of our more senior members, we will say, well into their 50s. And what got her into action was she's never reconciled her own identity as an inheritor, and she's about to send her daughter off to college. And it hit her like, wait, if I don't do this work for myself, how am I going to model and help my daughter get it comfortable in her own skin? For others, it's really about friendship and conversation and being able to talk about parts of themselves that they can't openly speak about. And then I would also say we have some members that it's like it's an insurance policy. Our members are very busy individuals building families, careers, helping family offices or philanthropic endeavors. So there's no one size fits all. But for some, they recognize that it's not if they run into life challenges, it's when.
Jake Knight
And when they do, they want to know that they can quickly plug in to people and not have to get them up to speed on from unique family dynamics because of wealth or why they're feeling lost in their work or whatever the case may be. And so there's really a variety, but ultimately, they're all coming for connection and personal growth.
Kirby Rosplock
That's awesome. That's really cool. So I can see how this really fits nicely with where you've come from, where you're going, and then how this is also So giving back so much to you, but also paying it forward to a whole community that you're cultivating. Just talk to us a little bit more. If someone were interested, how would they find you?
Jake Knight
Yeah, just ping us or reach out. We have a website, joinenclave.com. You can always reach out to me directly, just jake@joinenclave.com. We are a little a little bit on LinkedIn, but just track us down. We would just love to talk, love to share. We're not pushy, salesy type people. This either resonates or it doesn't. And would also be happy to be a resource, Kirby, for advisors or maybe family office individuals who are really trying to connect and understand how to better serve their next-gen, rising-gen clients. To me, it feels very redemptive to be able to share a story which at times was very difficult. If that can impact someone else or help someone else, or if something took me five years to figure out and through a little bit of walking through life together or perspective or experience sharing can help someone shorten that learning curve to two or three years, then it feels to me like the challenges, the pain, the confusion is worth something, and it's meaningful, and it's valuable, right? There's beauty that comes from some of our most painful life experiences. And so I I really get a lot of joy in being able to help others just through sharing and connecting dots.
Kirby Rosplock
So back to connecting dots. When you look at your own family of origin and enclave, do you see how this healing journey has helped you bridge some of the things in your own personal fact pattern? Has this been a way for you to some of the things of your own family? I mean, has this helped you figure out a way not to feel so disconnected or to be able to have a better working relationship with your family and just Has it helped?
Jake Knight
Yeah, it actually has. I've involved my siblings in various ways, and a couple of them have either joined or came to an event or a dinner. And so, yeah, that's been a really beautiful thing for us to be able to learn to be more open and to get to know each other better. These family systems are so complicated and so complex, and it takes effort to rework some of our identities and beliefs about maybe the roles we played growing up or the ways we viewed each other. And so there has been some healing there, some deeper conversations. I think the other thing it's done for us is we're being more collaborative and accepting of... Again, we come from a place of honor and gratitude. This is not this is not to disparage prior generations or our parents. We truly honor and respect and know that everyone does the best they can with the tools they have. And yet we all still have some shared experiences. And so this has created additional touch points and ways to share content and ideas with them, as well as some of my nieces and nephews and now my own children who are working towards their later teenage years.
Kirby Rosplock
Yeah. Oh, my goodness. You're coming right into it. I'm sure maybe you're seeing black sheep. I don't know. I have a couple of kids myself, and I know one of my children is potentially a little fringy and maybe a little black sheepish herself. All right, let's go into a little lightning round here as we're rounding out our of our podcast. Let me ask you a couple of questions to reflect back on some things we talked about. What's one thing that keeps you grounded on your hardest days?
Jake Knight
Misty and my kids. Yeah, they really keep me grounded. They pull me through the hardest days to say, one step at a time, tomorrow will be a better day. As well as, I will add, one of the things I found for myself as well to stay grounded is just building in slow mornings and space for myself, for spirituality, reading, journaling, meditation, those kinds of things as well.
Kirby Rosplock
That's awesome. All right, here's another good one. What's a belief you had to unlearn in order to grow?
Jake Knight
I grew up in a very black and white world, and so I'm continually learning and unlearning that there's so much more nuance to how the world works, how humans operate. And so really learning to lean into the gray or as we talk about now a lot more often, the both and and holding two truths that may seem contradictory to each other. I've really been challenging myself in that area.
Kirby Rosplock
I love that. Okay. Who's a black sheep hero in your life or someone who inspired you by walking their own path?
Jake Knight
Yeah, great question. Who comes to mind is my uncle. Again, he was raised in a small town, a very religious, tight-knit community, and he's gay. And so he didn't fit in. He had to hide that part of himself, really, most of his life. And so he's been with his same partner over 30 years. And as I've become an adult and got to spend much more time with him. We've had deeper conversation. I've got to see the challenges of his life within those religious structures. On top of that, he's the only brother within his sibling group that didn't work for the family business. He also was an outsider. In that way. But I've loved learning about him and just grown to have such a great relationship with him and seen him face so much adversity And yet he's the most loving, kind, thoughtful human being I know.
Kirby Rosplock
Okay. What gives you hope, brings you joy, or gives you inspiration?
Jake Knight
The younger generation. I have this unique... There's always this friction and tension around these younger generations, and they're not this, they're not that. And I've had such a good time watching my children grow up in a world that is very different than mine and extremely different than my parents. And they give me hope. While they have a different set of challenges, I see how much more in tune they are with their emotional well-being and being vulnerable and even meditation and concepts that I didn't learn about until I was well into my 20s. Their they're already tuned in on. And so I get really excited to see what this younger generation brings to the table in helping the world.
Kirby Rosplock
Okay. Last question. What is a quick resource, a book, article, movie? What comes to mind that might be helpful to all of our Black Sheep listeners listening today?
Jake Knight
Okay. I'm going to go out on a limb here. I I've read this book. I go back to it. It's been really helpful. It's a book by Lindsay Gibson called Adult Children of Emotionally Immature Parents. And I share this, again, not from a place of judgment, but it really helped. It's helped me make sense of some of my experiences, as well as like, ways to reverse engineer into how I need to develop to be more emotionally mature, because we all just naturally repeat patterns unknowingly, because that's all we know. And so I've just found it to be a great personal development tool to understand others' behaviors and maybe where that comes from, as well as to look at How do I purposely become more mature in the emotional side of my life?
Kirby Rosplock
Oh, fantastic. Jake, you are such an inspiration. Thank you so much for being here today. What an impactful journey you've had. Such honest humor, heartfelt, the whole thing. Conversation was such a gift. I am just so grateful for all all this sharing that you've done. And I mean, honestly, I feel like the black sheep moniker doesn't really fit. It is probably a little passé. We should probably just move on from it. But I mean, for all of us who felt like we've been on the outside. It's so wonderful to know that we can take that and we can make it something much more powerful and positive, and we can turn it into something really golden and really show how it can leapfrog us into a whole new realm. And I thank you so much for taking that wisdom and channeling it into Enclave, which I hope more folks will check out and learn about and join that powerful community. So we'll have a lot more links to it to be able to learn, find you, join the group. And again, thank you so much for being our guest today on the Tamarind Learning podcast.
Jake Knight
Yeah. Thanks, Kirby. I've enjoyed our conversation and appreciate you creating space.
Kirby Rosplock
Yeah, it's fantastic. So for all of you listening and being part with us today, if you liked it, please subscribe, whether it's on Apple, Spotify, Amazon or YouTube. Share it with your friends. Like us, subscribe. And again, thanks again for listening. And until next time, curious, stay bold and stay true.
