323 Gabe DeRita

Jeffrey Feldberg: [00:00:00] Gabe DeRita is a goal whisperer and personal growth nerd who left his fancy job in 2017 to travel the world by bicycle. In the process, he found his calling as a coach and facilitator. Gabe supports leaders at every level to maximize their impact by aligning with purpose, uncovering meaning, and embodying authenticity. Gabe doesn't fit neatly into standard categories, and his approach draws on many sources of wisdom and practice from his colorful career and background.

His experiences across many sectors makes his perspective unique. Prior to starting his own coaching practice in 2019, he held management, sales, and consulting roles in the tech, hospitality, and tourism sectors. He's coached leaders across many industries, from Y Combinator Tech Startup Founders, to Fortune 500 Management Teams in Hospitality, Retail, Financial Services, and Healthcare.

In addition to his coaching work, Gabe is a seasoned facilitator. He's created and delivered a wide range of transformational experiences for participants, both virtually and in person around the world, from boardrooms to [00:01:00] Burning Man. Gabe is a connection and communication specialist and holds a BA in political science from Bard College in New York.

He's trained in authentic relating practices, as well as co active coaching, and holds a professional certified coach certification from the International Coach Federation. He's passionate about cycling, foraging wild mushrooms, and making work feel like play. 

Welcome to the Deep Wealth Podcast. You heard it in the official introduction. We have Mr. Success on the call with us today here on the podcast in the house of Deep Wealth and whether it's from a startup, whether you have an established business, everything else in between, I have a rhetorical question.

You know, I love my rhetorical questions. Do you want to be more successful? And for your success, are you looking externally instead of internally? Are you just missing that picture? We're going to talk a whole lot about that and more. Culture and strategies and all those other things in between. 

And before we hop into the podcast, a quick word from our sponsor, deep Wealth and the Deep Wealth Mastery Program. We have William, a graduate of Deep Both [00:02:00] Mastery, and he says, I didn't have the time for Deep Both Mastery, but I made the time and I'm glad I did.

What I learned goes far beyond any other executive program or coach I've ever experienced. Or how about Bruce? Bruce says, before Deep Wealth Mastery, the challenge I had with most business programs, coaches, or blogs was that they were one dimensional. Through Deep Wealth Mastery, I'm part of a richer community of other successful business owners.

The idea shared forever changed the trajectory of the business and best of all, the experience was fun. And we'll round things out with Stacey. 

Stacey said, I wish I had access to the Deep Wealth Mastery before my liquidity event, as it would have been extremely helpful. Deep Wealth Mastery exceeded my expectations in terms of content and quality.

And you know what, my Deep Wealth Nation, why they're saying this is because Deep Wealth Mastery, it's the only system based on a nine figure deal. That was my deal. And as you know, I said no to a seven figure offer, and I created a system that we now call Deep Wealth Mastery that helped myself and my business partners, welcome from a different [00:03:00] buyer, a different offer, a nine figure exit.

So if you're interested in growing your profits, preparing for a future liquidity event, if that's two years away or 20 years away, and you want to optimize your post exit life, Deep Wealth Mastery is for you. Please email success at deepwealth. com. Again, that's success, S U C E S, at deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as Scale for Ultimate Sale. That's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders just like you who are looking to create market disruptions.

And they want to lock in their financial freedom and have success and fulfillment. 

That's the 90 day Deep Wealth Mastery Program. It has your name on it. All you need to do is take the next step. Send an email to success at deepwealth. com.

Gabe, welcome to the Deep Wealth Podcast. It's an absolute pleasure to have you with us. And I'm really curious, Gabe, there's always a story behind the story. So what's your story? What got you from where you were to where you are today?

Gabe DeRita: Thanks, Jeffrey. It's been a long time coming with this conversation. I'm really excited to be here. [00:04:00] And yeah, the story behind the story. I love the way you ask that because I think narrative is such a powerful way that we create value and meaning in the world. And I'm excited to talk more about that with you, but My story started with disillusionment.

I was working the job that I was told my whole life I should want. I was in a very successful role in enterprise tech sales in San Francisco, California, in the peak of the kind of recent software bubble around 2010 to 2017 was working in Silicon Valley, making a bunch of money living a life that I.

On paper, it was beautiful, but I was so dissatisfied. I now call it spiritual inflammation. This sense of being almost allergic to my daily life, where it was okay, but it was uncomfortable, and something was just off. And in 2018, I quit that job, left that career, left a partner of eight years, sold all my stuff, and actually moved onto my bicycle.

And I traveled solo for almost two years, most of that on a bike seeking deeper purpose and meaning. And I was inspired by this [00:05:00] Japanese concept called Ikigai, which in the West has been lovingly adapted into this Venn diagram with four parts, which is what the world needs, what you can be paid for, what you're good at, and what you love.

And I realized in my tech sales career, I was good at it, and I certainly got paid for it. But it was questionable whether the world needed another app, and I certainly didn't love what I was doing. So I basically burned my life to the ground to rebuild from this place of orienting towards deeper purpose and meaning.

And that's how I found my career in coaching and facilitation, and feel very blessed and honored to do the work that I do today as a result.

Jeffrey Feldberg: Wow, quite the story there. And before we go into the wonderful things that you're doing, let's go back to that because in your words, here you were, you had success by every stretch of the imagination, at least from the outside looking in, and then you just left it all behind and you're on your bike for two years.

So I really want to know. When you're doing that, I mean, what was that like? You gave up, it sounds like your material possessions. You're just going from place to place. What did [00:06:00] life look like then compared to what you had before that and some of the insights that came out of that?

Gabe DeRita: Yeah, I'm reminded of something you said at the beginning in the introduction to the podcast where you mentioned like looking externally versus looking internally for sources of wealth and that process of living on a bicycle was very much a process of looking inward and relying on myself and kind of trusting the resources I had in the moment and trusting the resources that the road offered me, it reminds me of one of my favorite living poets, David White, talks about this process of being one step in self forgetting and one step fulfilled by what you meet.

And that's what living on the bike was like. I had to leave so much of myself behind and just step into whatever was opening up to me in the moment. And I couldn't plan very far in advance. It was really just about how much water could I carry? Where was I going to sleep that night? What was the weather like or the topography?

And it felt much more like a Continuous moment of perpetual intimacy with the world around me instead of like future planning and 401k and the quarter and the [00:07:00] quota and the deals it was like all of that dropped away and all that was left was the moment I was in and the people I was with and that sense of presence really deepened for me and I think that was a radical shift in how I was living my life.

I

Jeffrey Feldberg: I really salute you. I mean, that takes courage. People talk about, yeah, I'm going to be in the moment. I'm going to, Put my material possessions behind and just really go out there. Yet very few do, but you did that. And so when you look at who you are today, compared to when you began that journey, so the first day you're on your bike, everything's behind you.

You made that decision. I imagine a lot of, Oh my goodness, what did I do? Was this a mistake? But fast forward now to where you are, how did that change you? Because really, I suspect you unplugged from a lot of the social programming that we're getting. And what really seemed important at the time, you're probably looking back and saying, I really wasn't, it seemed like it at the time, but it really wasn't that important.

I mean, how did you change coming out of that? I'm just curious.

Gabe DeRita: there are many things about me that are different as a result of that journey but [00:08:00] One of the most prominent is I feel like I have a much deeper trust of my intuition in my system of values now and my system of meaning making. Whereas before I think I had taken a lot of things externally and made them my own Oh, I need this career.

I want this lifestyle or these types of choices matter to me when really they had been things I had maybe been told to want and had never investigated at that deeper level, whether it was something that was deeply true for me and living on the bike and really starting my life over in many ways. Ways, personally and professionally give me a chance to recreate that system of meaning from scratch.

And I feel like I trust the choices I make a lot more now knowing that they're aligned with a deeper, like self knowing. And it's the way I'm guiding my life is rooted from a more interior place instead of things that I'm maybe told to want by the external world.

Jeffrey Feldberg: So important today, and I don't want to get on my social media soapbox of how we're all being told the things that we want to be told and the algorithms and how it's really divisive with everything. What's [00:09:00] fascinating about you though, Gabe, really from the startups and you've worked with Y Combinator, probably one of the best known, most successful startups around in terms of who they're getting out there and the changes that they're making to Fortune 500.

And everything else in between. And even from, as the listeners heard in the introduction, from the boardroom to Burning Man. So I'm wondering, I mean, people are people. When we look at people from a leadership perspective, and now as you're working with leaders, regardless of company size and where they're at in their development.

Are there some common patterns that you're seeing? So if we looked at the most successful leaders that you've really had the opportunity of working with, what would be some of the key traits or really common characteristics across those leaders that you're seeing in them, but not necessarily in the leaders who either aren't as successful or wouldn't be as effective?

Gabe DeRita: That's an interesting question, and I actually kind of want to flip it to answer it, where I think that the ways that people are challenged in relationship and success are all the same. So, all of our inner voices, our inner saboteurs, our [00:10:00] imposter syndrome, our doubt, the ways that we generate fear and limiting beliefs.

Those are the same in every individual that I meet, but the way that we solve those challenges is what's different. So it's the greatness in us and the light in us and the power in us that's really unique across different people. And the magic of my work and the real fun I have in it is finding ways to unlock and uncover those resources in people.

Because the common denominator is actually the challenges. That's what everybody thinks is different. Like my business is unique. My challenges are unique. And, you know, maybe your, market is unique or your company size is unique or your product is unique. But the way that you actually generate fear and doubt and limiting beliefs is the same in everyone.

What's unique about us is the way we solve those challenges and meet that moment. And that's something that's been really interesting. And in many ways, comforting for me in this work is to find out, Oh, we're not so different. I think a lot of the challenges that we have feel so hard and so intractable because they feel so unique to us.

But we all suffer from what's called protagonist [00:11:00] syndrome, right? We're all the main character of our own movie. And so we think we're in this unique moment of challenge, but it's actually a challenge that's been met by many people throughout history. The idea that a myth is not something that never happened, but that happens all the time, right?

We have these narratives in our culture for a reason, because there are so many common denominators in the human experience in our challenges, but our, uniqueness and our, our gift to the world, it comes in how we meet those challenges. So that's how I would answer that. It's not that what's unique about people is the way that they're all kind of struggling in similar ways

Jeffrey Feldberg: And Gabe, let me take what you just said, which I absolutely couldn't agree more with it and really value what you're saying. And you put that back to yourself for a moment. So now you've finished your two year stint on going from place to place, living day to day, you're on the bike, you're looking back.

I mean, what did you see within yourself that really had you come to the realization that you just shared with us now, and you're now taking that and sharing that with leaders? Across the country and around the globe. What was that in you that you saw that was perhaps a surprise for [00:12:00] you?

Gabe DeRita: in terms of a challenge that I was

Jeffrey Feldberg: in terms of your social construct of, okay, you know, here's Gabe.

I went into the bike ride thinking this and I came up thinking, wow, I was either spot on, or I couldn't be more far off a base than what I was looking back now.

Gabe DeRita: That's interesting. I think that change is still ongoing. I don't think it was, like, complete the day I got off the bike or anything like that but I think it really started a process of deeper honesty and self inquiry within myself where I was trying to know myself better and make myself a better human.

developed this concept of wanting to make myself into a masterpiece that I could give away to others and just having something almost unlimited within me that I could share and this concept of being spiritual billionaire was something I heard on the road and it sounds a little goofy, but it's sort of this notion that we have this inner source of wealth and authenticity and character and quality of being that never runs out.

And I think that was something I discovered in myself and wanted to learn how to polish and share that. And I think before my trip, I was very focused [00:13:00] on. Just enjoying my life. I was young. I was like more hedonistic. It was just about money and pleasure and fun. And I think something that shifted in that journey was looking for ways to serve the world in a deeper level.

There was almost like an up leveling in my maturity in the sense that That I, sought to live for something greater than myself, maybe for the first time. And I'm not a parent, but a lot of my friends have become parents in the last few years and I can see how becoming a parent lights this new fire in people.

And so I feel like that's kind of the thing that changed in me was finding ways to, to love the world in different ways beyond my immediate self interest. And the author Susan Sontag was asked about her decision not to become a mother in an interview. And she said, love has other work to do in the world.

Right? So whether you're a parent, whether you have a family or whether you're serving some greater cause, there's love in you that has work to do in the world. And I think that was part of my process of self discovery was finding out that resource was in me and asking that question, what does this love want for the world?

[00:14:00] What do I want to create with it? And I know that sounds very kind of spiritual, but it has very tangible and practical like business outcomes too, in terms of creating from that deeper place.

Jeffrey Feldberg: And really, as you're going through that, it just reminds me when I think back myself to some of the greatest achievements, particularly in the business world, it's coming from exactly what you shared, Gabe, of this is no longer about me and my enrichment. This is really about how can I enrich the world?

How can I make the world a better place? How can I solve people's problems? And if you take that a step further, at least in my books. That's really an entrepreneur, a business owner, founder, isn't that what it's all about in the first place? Hey, you have a problem, I have a world class solution, let me take your pain away, and if I can help enough people first and take their pain away, eventually, over time, I'll be able to achieve my goals as well.

So what you're saying really resonates with me, and if you go back to what you said earlier, Hey Jeffrey, look, before you look at the successful leaders, let's just take the position and Gabe, you can correct me if I'm on base or off base, [00:15:00] that as people, we're all more or less the same. We all have our fears or aspirations, our challenges.

And if I'm hearing you correctly, what you're saying is how you can get to that successful place is really how you're looking at, okay, how am I going to solve this problem or what's my mindset or the tool sets that I'm going to apply or the strategies to really make the difference? How am I doing with that?

Gabe DeRita: I think you're right on in the sense that the common denominator in everyone is our challenges and that the process of creating success is unique. And that relies that on our understanding of the toolkit that you mentioned. And I think that toolkit has some key elements. One of which is self knowledge, right?

How well do you know yourself? Another one is how deeply are you aligned with your why, right? Your purpose, your meaning, that love that you want to bring to the world, that entrepreneurial spirit of how you want to solve the problem or serve the greater good, whether that's your customers or your people, anything else.

Another component is your [00:16:00] relational skill. And your ability to create connections and shared understanding and navigate conflict. How malleable are your ideas? Are you able to change your mind? Are you rigid? Are you somebody who's fixed in the world in their system of belief?

And how do you incorporate new meaning or course correct along the way, right? So these are some examples of things I coach people on. And some of the trainings that I give to teams is to help build those skills of. Intellectual resilience, self knowledge, relational skill and communication and conflict mediation.

And it boils down to creating space for people to show up more authentically in their role. Because the more complete we are as humans, the more of ourselves we can bring to our work instead of feeling like I'm, A father at home, I'm a businessman at work, I'm a coach on the baseball field we're in these different roles.

If we silo our talents in thinking we're only valuable in certain ways in all these contexts, then we limit the impact we can have instead of feeling like we could bring our [00:17:00] whole selves to everything that we do.

Jeffrey Feldberg: And so coming out of this, you've highlighted, Hey, Jeffrey, it's really the ability for a leader to be resilient. How good of a storyteller are you? Can you trust in people and can people trust in you? Can you trust in your own intuition and really look within instead of without as you're going out there to.

Grow the company, make that difference, do that self discovery, go into the unknown. And for me, it's really asking the question then, Gabe, assume I'm a person, it could be a company. I know rightfully so, you can say, well, Jeffrey, with the question you're about to ask, every person is different. Every team is different.

Every business, every culture is different. And I get that. But that said, when a business or a team, when they come to you or a leader and says, hey, Gabe, walk me through your process, have me come out the other end, really my true authentic self so I can really affect and effect change. What does that look like?

What's your secret sauce with your process? What would I expect to go through? 

Gabe DeRita: that's a fair question to ask. It's funny because the process. It's very similar for individuals and for teams. So I [00:18:00] do this work both with one on one leaders and also across organizations, training cohorts with different facilitated leadership development programs. And it really starts with the story of self.

It starts with that. Understanding of values, understanding of purpose, and mission, and vision, and that translates from the individual to the org through creating alignment between what's my individual why, and what's this all for the sake of, and then how does that align with what the business is doing, and vice versa, and then we look at ways that value is expressed in the world through the choices that you're making, and kind of do an inventory to calibrate how aligned is this sense of who you are Inside to how you're acting outside.

And that was basically the process I did for myself when I burned my whole life down. I was like, wow, there's a lot of things about me that are really important to who I am that I'm not expressing in the world through my choices and actions. And a lot of times that process is uncomfortable. I call it the bounce.

Where everybody kind of is excited to begin and then they do the [00:19:00] inventory and they have the honest conversation that there's a lot of things missing or some hard choices need to be made. And we kind of go through that process of maybe peeling away some things or making some different decisions or setting some new boundaries to recalibrate to that deeper source of inner meaning.

And once we're able to do that, a lot of the choices that people make feel easier. It starts to get more effortless because you're coming from that source of deeper power within, and you're more aligned with those important self created sources of meaning. And when you're coming from that place, you're able to really build character and create authenticity a lot more effectively.

And we move to kind of training on communications, relational skill, managing conflict, creating enrollment for these ideas with your team, with your organization, with your shareholders, with your customers, to build that out from that inner system of meaning and ripple out to then how do you enroll people in this vision you have for the world and create alignment around the things you want to build and create?

Jeffrey Feldberg: And so with that [00:20:00] enrollment, because you read my mind game, so it sounds like working with you and going back to the IKIGAI concept, which I love, and we've written about here at Deep Wealth, and we've really embedded that into our Deep Wealth Mastery Program. The question remains though, and we see it time and time again, whether it's a company that goes off on this big retreat, and they come up with this vision or this mission, and if you fast forward six months or six years later, it's really the same, nothing happened, it's these fancy words that really mean nothing on some kind of plaque, Collecting dust on the wall.

So from the bounce, as you called it, to the enrollment, once we've had you work with us and you've really coached us to get out our Ikigai and we're now on center on target with that, how do we actually implement that? What are some strategies that work that we're sticking with it, even through the tough spots, because we're not used to it, it's new, it's easy just to go back to what feels comfortable, even though that's not right and it's not the best way to do it.

How do we see this through?

Gabe DeRita: Yeah, that's a great question because. You don't want to invest all this time and [00:21:00] energy in making a beautiful mission statement that just lives as a source of hypocrisy and resentment for your employees, right? Because they say, yeah, this is not what we're about. It requires practice and consistency and radical candor and honesty with how well are we doing?

How hard does this still feel? And one of my clients jokingly said to me, Gabe, all of this is just about remembering to remember, isn't it? And he was right that like, when we're triggered or challenged by the circumstances we're in, how good are we at remembering the agreements and commitments we made to ourselves and to our people and to our product and to our vision to stay consistent with what we're trying to do?

James Clear got famous for writing this book, Atomic Habits, and in it he says, consistency beats intensity. And I always tell that to my clients. You're going to come back from this retreat or your, you know, big coaching session, you're going to feel so intense and aligned, and you're going to want to get after it and rebuild and do all this stuff.

And I don't actually Recommend people do what I did of this really intense process of transformation. I think it's actually more [00:22:00] effective to just be consistent in small ways that like 1 percent better type thing, but staying oriented to those commitments you made to yourself, to what you uncovered in that values or that IKIGAP process, and just have systems to check in and say, how am I doing?

And that could be accountability with a coach. It could be a peer on your team. It could be a post it note on your wall. Something that really jumps out at you on the day to day basis, in the small ways, not necessarily the big ways, to really make sure that you're just creating measurable, but consistent progress towards true behavior change, whether that's at an individual or organizational level.

It's really just about practice. There's nothing glamorous about it.

Jeffrey Feldberg: I'm with you, as we like to say, Deep Wealth, dreamers dream and doers do, no such thing as perfection. It's just better to keep on going out there. Version two will be better than version three, which will be better than, version four. And off we go with that. The next version is always better, but you got to start somewhere.

To keep on getting out there, to get that rhythm and get those rituals all together and keep all of that going. [00:23:00] And so let's flip it because at the start of the conversation and, you know, most entrepreneurs and business owners were type A personalities and the glasses always half full. And I'm just wondering if it's the opposite of what you shared, when you either observe or even work with leaders who perhaps aren't on the best platform, or they're just not doing the right things, they have somewhat of a losing streak that's going on, for the leaders who are just missing it all together.

What's going into that? What would be some of the patterns or the characteristics that failure as we know is as good or even perhaps a greater teacher than success and knowing what not to do is often as important if not more important than knowing what to do. So when you're working with teams that have just missed it altogether and you're getting them back on point, what are they doing that you can share with us that we should avoid doing?

Gabe DeRita: I think that question is harder to answer because it's a little bit more subjective in terms of doing that diagnostic process and finding out the challenges. But I do think I could give an answer for anybody [00:24:00] who's either in a position where they're really stuck and it's not working or they're actually starting to do well, but still on that path of improvement.

It's welcoming the recognition of the failure as a success. And I can give an example from a retreat that I did. I was in a meditation retreat and I kept getting so frustrated that I would catch myself drifting off and not paying attention to my breath. And on like day three of this retreat, I realized that the moment I catch myself off the mark is actually a cause of celebration because I've successfully brought self awareness to the moment and remembering to course correct.

 Especially teams that are really challenged or leaders who just struggle to get it. It feels really difficult to invite them to welcome that recognition of not doing it right as a moment of celebration, especially like you said, if you're type A, perfectionist, it can be very hard to admit that you're failing.

But if you're not willing to look at it and recognize the moment of seeing your failure as an opportunity to create success, that's almost a zero to one moment. Because then you're using [00:25:00] all of these Moments as learning opportunities instead of moments to beat yourself up or create internal resistance because your brain's not going to want to do it if you think it's a problem.

But if you start to create a little dopamine reward, a little hit of Oh, all right, cool. At least I caught it this time. That's what allows traction to build over time to create success and really change behavior. maybe, I don't know, what are they all doing wrong? It'd be harder to answer because there's so many different ways that like problems are generated, even though the primary colors are the same.

Like I said, at the beginning, I think I And a solution is just welcoming those moments of self awareness, even if it's a failure, as a chance to build success.

Jeffrey Feldberg: And so let's talk about that because At Deep Wealth, we take a very contrarian view in the sense that for a lot of people, we'll hear something along the lines of, hey, success is nothing more than a complicated formula in a spreadsheet.

And for us at Deep Wealth, we're saying, actually. That couldn't be the furthest thing from the truth because success, it's in the art of business. Or if you're having a liquidity event, it's in the art of a liquidity event. A lot of these [00:26:00] things don't show up in a formula. They don't show up on paper as the saying goes.

And Gabe, where you're operating, really working with the culture of a business to ask culture is. Everything, because a rich, thriving culture that has a positive impact on every single stakeholder within the ecosystem of that business and culture, well, you're not going to ever see that on a spreadsheet or in a formula.

And what goes into a culture to make it rich and thriving and replicable in a very positive way, again, that doesn't show up in numbers. It's just a way of being as opposed to, well, I'm just to doing instead of being on that side. So you're operating there, and it goes also back to that Ikigai again, on the art side of life, it's a very subtle but huge mind shift when you think about it that way.

So from a culture side of things, what can you share with us? Because I'm sure you've seen the good, the bad, the ugly, as the saying goes, when it comes to culture, what to do, what not to do. So if I'm being honest [00:27:00] with myself, I'm taking stock of my business, I'm taking stock of my culture, and I'm saying, oh, you know what?

Our culture really isn't that great. It's perhaps even toxic. Where do I start with that, Gabe? What can I do?

Gabe DeRita: Yeah, I think being honest with yourself and being willing to ask those hard questions and maybe hear from people who disagree with you as a leader, you have this, the rose colored glasses on. Ideally powered by a very strong why and a passion for what you're doing, right? So it may be hard for you to admit that you have the law of unintended consequences, right?

And some of the choices you're making are generating results that aren't aligned with the bigger vision that you have. So I think that's step number one is, are you willing to hear the truth and be really honest with yourself and solicit feedback from Your detractors, people who aren't necessarily enrolled, instead of thinking, no, this is about them, this is an individual problem, or they're just not sold, we haven't hired the right people.

Could you listen for the 10 percent right that everybody who disagrees with you might be? Angel Kyoto Williams, another amazing teacher, she has this phrase, she says, we have to allow for the [00:28:00] incompleteness of our truth. And so nobody has all of the truth. And as a leader, it can be really easy to believe, especially if you're successful, that you got it, you got the whole picture.

So can you welcome the dissonance and the things that don't fit with your truth and your system of belief so you can enrich that picture for yourself? That's really where to start. And I think once you're willing to do that and have those honest conversations to seek the ways that you might be missing the mark proactively, then I think the most important piece of a culture is trust.

Psychological safety and trust. And so what can you do as an organization, as a leader, to build that culture of trust? Because if people aren't trusting, then they're hiding something back. You're missing the best that they have to offer your mission and your team because they're kind of playing it safe or close to the vest.

And so do you have a culture where people feel safe to challenge an idea without repercussion, where people feel That high level of psychological safety and trust and support from their peers to take risks and a good leader, right? We think we're supposed to have all [00:29:00] the answers. A good leader is not just responsible for the answers.

They're responsible for creating a space where their team feels safe to experiment, to be inspired, to bring their curiosity, to take risks, to fail and to learn. And in order to do that, people need to feel safe. And so that's typically one of the foundational pieces that I train for, and that I see the most successful organizations doing is that they're really proactive in creating that culture of trust and safety.

So people can embrace conflict as a generative thing, that they can be authentic and honest with who they are and the ideas they have for the business. That we have, it's not like governing by consensus. I don't think that always works but it's a place where people feel safe to speak their minds and be seen for who they are.

Jeffrey Feldberg: Trust, Gabe, you mentioned that word, you've shared that a few times, and at least for us at Deep Wealth. Trust is where it starts and where it ends. Without trust, nothing happens. If a prospective customer doesn't trust you, you can give your services away for free, they're never going to pick you up on that offer.

Or if you're really out there, you're at the high end, again, if someone doesn't trust you, it's just not going to [00:30:00] happen. If your team, your employees, if they're not trusting you, well, they're not going to go above and beyond to get that to happen. And so when it comes to trust, it leads me to one of the questions that we love to ask either business owners or leaders or executives.

And the question is, does the business run without you? And even in instances where there's a leadership team or a management team. Oftentimes, if it's the owner, well, sometimes the management team, it has to pass by every single decision by the owner. So it doesn't really run without that owner, or maybe the owner has done the right thing and there is a leadership team, but you have a leader in there who just doesn't trust and really micromanages and the business revolves around that one person.

So in that, and the person who's listening and hopefully they're being honest enough to say, Oh, geez, Jeffrey, you know what? I'm hearing you talk. I hear some of me that's in that. So to that listener, Gabe, how do we begin to unwind that vicious cycle where, whether we're the owner of the company or we're a team of people reporting into us, we don't necessarily have that trust or it's not [00:31:00] running without us autonomously.

And by the way, I don't go for, abdication, this is delegation in the healthiest of ways, not just walking away and forgetting about it. So what can we do? For that listener saying, yes, Jeffrey, that's me, guilty as charged, Gabe, what advice, what strategies for that leader would you give, okay, you can walk this back, here's what you can think about doing.

Gabe DeRita: love that you double clicked on trust here because there's so much richness to discuss and it is such a powerful topic. And I have the privilege to work with a great man and a wisdom keeper named David Lappin and I learned this from him. He talks about trust having directions. And so a lot of leaders think about trust as like, I am trusted, right?

So I am the source of wisdom or information or I'm the buck stops here. I'm trusted, I'm a rock for my people. But are you also trusting? Are you willing to let trust flow to the people that you work with? And so most people think of trust just as I'm trusted. Not many people think of trust as I am also trusting.

I am willing to put the faith in those around [00:32:00] me to carry this vision with me. And so that's what I would challenge those leaders to do is maybe take an inventory of does the trust all flow towards you? Because yeah, that feels good, right? But are you also allowing the trust to flow out? And that feels risky, but if you are a trusting leader.

That's where the power lies. So not just being a trusted leader, but in what ways could you become a trust, not just a trusted leader, but a trusting leader as well. And I think that's, not a concept that I hear a lot of people talking about is that trust has directionality to it. And if it's only flowing one way, then it's limited.

Jeffrey Feldberg: Okay. So some honest conversations there to be had and looking a lot in the mirror and reflecting back upon ourselves. And Gabe, maybe you've had a situation that you can share with us where the culture wasn't great or it was trust, but not trusting. And I love how you differentiate that because you take trust in and of itself is not an active word, but trusting that becomes a very active word.

And it's very subtle, but it's a huge difference. How do you go about doing that now? So we've really set [00:33:00] this up. We've gone through a few different areas. We've talked about a few different things, but big picture wise now for an entire organization to begin that process to move and you're working alongside and you're coaching and you're mentoring along the way, any insights that you can share with us?

Gabe DeRita: Yeah, if I was coaching an individual leader on this trusting thing, I would kind of ask them, where is it hardest to give up control? Where do you feel the greatest amount of fear in letting something go or where do you not believe it's possible for the business to exist without you, like you said, and really look at those hotspots of maybe your process is not generated by.

Something that's deeply true or good for the business. Maybe there's a lot of fear that's driving the pattern of control that you have in this particular area. And so just kind of doing that heat map of like, where does this feel like you're really white knuckling it, and kind of holding on too tight and using that fear as a guide.

to the places where we might want to soften a little and cultivate that ability to be trusting and then looking at, okay, well, what is the fear protecting you from? What do you feel like you would need in [00:34:00] order to be more trusting here? Is it about you? Is it about the other person? Is it about the system?

Right? And just kind of getting really honest with what's in the way. But really, I think starting with that fear and using that tension around it as a guide to, this is probably where you need to start. Kind of across the board, a bit of a trick of what's the most uncomfortable thing in front of us right here?

That's probably an indicator of where we need to begin our work, whether it's in trust or communications or whatever the topic is.

Jeffrey Feldberg: And Gabe, I've been all over the map and I'm going to throw another question that's all over the map out there, but I promise you there is a method to the madness. And for our listeners, we've really been building the foundation and hopefully what's coming up for the listeners as really you very eloquently have shared with myself, Gabe, and my takeaway, it doesn't really matter if you're in a startup or you're in an established business, thousands, tens of thousands of employees.

It all starts within us as a leader, as one person to really affect and effect that change that's there. And so I know you have [00:35:00] what's called the inner edge and it's a five week journey that you go through with leaders and with people and really the corporate world and entrepreneurs and everyone else in between with that.

So what's that like? I know we've kind of hinted at that, but Gabe, going through that, what can I expect? So I'm okay, Gabe, this is day number one of the five weeks. Where are we starting and where are we ending up? What can I expect? What does that look like for me?

Gabe DeRita: Yeah, thanks for asking. It's funny you mentioned that because I was just planning yesterday like, when am I going to launch that again? This is just another little bit of a push for me to do it. But we really start with that purpose and values place that we mentioned at the beginning. It's really how clear is that inner vision?

How aligned are you with your why? Do you understand your values and how they operate in the world? Because that's the funny thing about values is they're actually guiding our decisions and our choices whether we've named them or not. And so your values are a guide to the tough choices that you make.

And you can actually use those tough choices as a way to see the values in yourself and others. [00:36:00] And that can be a powerful relational skill to have. So that's where that work begins is really in that self knowing. And then follows the same pattern that I mentioned with how I work with teams and train this stuff is like we build that inner self knowing and then we start to ripple it outward into relationships, into creating connections, into negotiations, conflict mediation, building that relational skill set from that deeply aligned and authentic place that's rooted in values and purpose.

Jeffrey Feldberg: As you're going through that, and as I was prepping for this and going through what you're offering and what's out there, it just brought me back to one of the sayings that we have at Deep Wealth, that whoever said business isn't personal. Either they've never been in business, they've never ran a business, or they've never owned a business.

Business is personal in every aspect, and the most basic of which, if we don't have it right within us. So if our personal world is all over the place, it's disruptive in a negative way, and there's really no cohesion there, and it's really taking away from us. It's going to reflect in our performance.

It's going to reflect in the [00:37:00] business if we're leading that business. And it's just not a great combination. But if we can really go within and have that inner calmness and stillness, that clarity, that confidence, that resilience, as you had mentioned earlier, that's going to make a huge difference. And we've heard this different authors, different thought leaders, even ancient civilizations over time.

Our inner thoughts, our inner feelings, that's what manifests and create our outer world. So again, I'm way out there for some of our listeners, and this is definitely on the art side of living life and the art side of a successful business. It's certainly for me, a formula and a strategy that has really proven itself time and time again.

Any thoughts on that? Am I off base, on base? What would you say to that?

Gabe DeRita: Yeah, I actually, I want to use that opportunity to challenge a few things that I see a lot in the personal growth space that I think are ineffective because of the way that they're framed.

The first is this idea of manifesting. And it's funny, I have a friend who has a business all about manifesting and we joke a lot about how this term really falls short [00:38:00] of what's required.

Because we think it's just enough to make our vision board and have good thoughts and wake up every day and the universe will say, yes, thank you for thinking good things. Let me give it all to you. That's not how it works. Our beliefs only create results for us if we use those beliefs to generate action.

And I think Michael Jordan said this, he said, we're only do what we think we're capable of. And so that's really the trick of this air quote manifesting thing is like, We need to expect good things to happen in order to plan for them and build behavior around them. But we still have to do in order to create those results.

Like you said, the being and the doing. The doing starts in the being, but it doesn't stop there. We also need to connect it through to consistency and action. And so I like the concept of manifesting because it does require we Bring the locus of action all the way back to our thoughts and our beliefs about the world, but we can't make the mistake of thinking that's enough.

That's the first thing. And then the second thing that you said was this idea of kind of business is personal. And [00:39:00] I have this somewhat playful belief that work life balance is a myth in a very important respect in the sense that we're the same human being. at work and at life and if we're trying to balance these two different personalities of doing the things at work and play that are very different and kind of fragmenting ourselves then we're missing the whole point of that process which is just to create a balanced human being who can move through every arena of their life with skill and authenticity and grace and so I try to Unlearn some of that concept for myself and with my clients, that we're not trying to balance your work and your life.

We're trying to create a balanced life. And you are the key ingredient there. You are the fulcrum on that scale instead of stacking the coins on one side and the other. And so I think that the idea of work life balance can be misleading for people because they separate themselves into these two categories and it doesn't necessarily.

Jeffrey Feldberg: Absolutely. Some brilliant points that you put out there and working from the end to the beginning in the reverse order. I agree with you. As we say here, Deep Wealth, [00:40:00] take the concept of really balance and a balanced life. Leave it for the movies. Leave it for the fiction books. It doesn't exist in real life.

And for me, it's really more of blending as you're talking about. I can blend. So perhaps I have. A business trip, well, perhaps I can blend and take my family along or take my significant other along. So I'm having some fun, but I'm also having some business at the same time and back and forth with it. But balance, throw that out the window.

And absolutely, if I'm just going to have a vision board, if I'm just going to think good thoughts, but I'm not taking action upon that, well, more than likely, nothing's going to happen. And what's interesting is. Science is actually now catching up with this because science says, okay, when you make yourself aware, so on the vision board, if I put my goal out there, I know I'm aware of that.

But what's going on from a science perspective, some fancy words here, the reticular activation system in the brain. And so for our listeners, I want you to imagine. You're looking to purchase something. Let's keep it really simple. A red sweater and you haven't bought it yet, but you've been thinking about it.

You're [00:41:00] walking down the street and all of a sudden everyone is wearing a red sweater. So the question becomes, do those red sweaters magically manifest themselves or were they always there, but you didn't pick up on it? And it's the latter. They're always there. You didn't pick up on it because you've now brought that to front and center.

Your brain is an amazing. Really tool and instrument, and it's now making you aware of that so you can then take action. So the same thing when we're, okay, these are my goals. This is what I want to manifest or what I want to achieve. But now I'm more open. Oh, Hey, yes, Mary. Yeah. I remember Mary. She does this and that, that can really help me with that.

I'm now taking action on that. So Gabe, I'm right there with you and some powerful takeaways for our listeners. Gabe, let me ask you this before we go into wrap up mode, we've talked a lot of different strategies. And for every episode, wherever possible, if a listener before hopping off of this episode and going into whether it be a meeting or a phone call, whatever activity they have next, if they could take one strategy or one action from what we've talked about or even haven't talked about, what would that one thing be that could [00:42:00] really move the dial?

And maybe it's even a low hanging fruit. It doesn't take a lot of time and effort for them to do, but they'll get the results with it.

Gabe DeRita: I might not have thought I would have said this at the beginning of the podcast, but I want to say act as if, because we're talking about, your thoughts create your reality in some respect. And so any situation you walk into, act as if the thing you want is already happening.

Because that kind of activates that red sweater thing you were just talking about, act as if, you've already sealed the deal. Act as if this person really trusts you and wants to believe you, not in a way that creates assumptions or clouds your reality with what's actually happening.

You want to stay responsive and engaged to what's arising. And that's actually a big part of the practices I teach is assume nothing. So this is a bit of a contradiction or a paradox here in terms of what I'm saying. But acting as if it's something we can do for ourselves to generate that self belief that we have the power to really influence the scenario we're in by how we show up to it.

And so who we are in that moment matters so much, [00:43:00] not more, but like just as much as what we do. And I think that's what I would say to people is just really get into that. And that's the way that you can be in a place of alignment with yourself and act as if the thing that you want to happen is like a foregone conclusion.

Not in a way that detaches you and makes you aloof or like assuming things or naive, but in a way that allows you to ground into this sense of presence and power and peace within yourself because if you show up that way, then you're much more likely to generate that result.

Jeffrey Feldberg: Terrific, act as if, it's great advice, and really, I've heard this before, emotion, that's what creates motion, and all these other wonderful play on words, but act as if, and let me ask you this, is there a question that I haven't asked, or a topic we haven't covered, or a message we haven't spoken about that you want to get out to the community?

Gabe DeRita: I want to talk a little bit about the concept of authenticity because we've mentioned it a few times and it's one of those words that's kind of so overused it's become meaningless. It's like seeing all natural ingredients on the label of something like that doesn't make sense.

It doesn't mean anything. All ingredients are natural. What do you [00:44:00] mean? Authenticity, right? It's like such an overused word. And so if you're the listener and you're kind of in resistance of oh, Gabe and Jeff had just been talking about all this woo stuff. And what does this actually mean?

I would challenge you to really Picture how it feels when you're with somebody who's just so authentic and so themselves and so aligned and how does it make you feel when you're in the presence of somebody who's grounded and regulated and excited and alive and fully connected to the present moment and imagine the impact that has on you, you can have that impact on other people and that's what I think authenticity is, it's aliveness and it's this quality of character that's magnetic, when people have it, When they're in the present, like, where there's no problem to solve and we're just kind of playing with what's here in a way that's non judgmental and open and real, it creates such a different quality of relationship.

And that's what I mean by authentic leadership, is we show up with that quality of being and that presence and that character that's [00:45:00] Enigmatic, it's charismatic. People know what it's like when they feel it. And so if you're thinking, oh, authenticity, it's a buzzword. It's overused. It's not specific enough.

I want you to think about somebody who in their presence, you feel different. You feel more permission. You feel more play. You feel more aliveness. You feel more excitement. That person's authentic. And how could you emulate that for yourself is the invitation.

Jeffrey Feldberg: terrific advice, Ann. And Gabe, before we go into wrap up mode, as you're sharing with that, my wheels were turning and I remember hearing, whether it was from interviews or even people that I've spoken with, that they're working with a Titan of business, a really successful person. And the one common theme that they would say, I never spent a lot of time with this one individual, with the owner or my boss or area leader, whoever it may be, but the time I spent, however little or much that was.

I felt like I was the only person in the world for them. They were listening to me. They got me. I felt safe and I could say whatever I wanted and they really cared about what I was [00:46:00] saying and they cared about me. And even if it's only for a few minutes and that's the only time I had with them for that quarter or maybe even the year, that had me go above and beyond.

And that's been a common pattern that I've heard time and time again of really effective leadership, regardless of how successful or wealthy or how busy, when you're with your team, you're with your team and nothing else is coming in there. That's the only person that exists truly being in the moment at that point in time.

And from being in the moment, going to another moment, it's a perfect segue for our wrap up here. It's a fun question and it's a ritual we here have at the Deep Wealth Podcast. And the ritual is that we ask every guest the same question. So let me set this up for you, Gabe. It's a fun one. When you think of the movie Back to the Future, you have that magical DeLorean car that will take you to any point in time.

So imagine now it's tomorrow morning and here's the fun part. You look outside your window. Not only is the DeLorean car there. But the door is open and it's curbside. It's waiting for you to hop on in. So you do, and Gabe, you're now going to go back to your younger self. [00:47:00] Gabe, as a young child, a teenager, whatever point in time it would be, what are you telling your younger self in terms of life lessons or life wisdom?

Or, Hey, Gabe, do this, but don't do that. What would that sound like?

Gabe DeRita: It's so funny. You use the DeLorean example and the younger self, because I actually almost had a chance to drive a DeLorean to senior prom. And so I, I would go back and drive that DeLorean from, in all seriousness yeah, I would tell my younger self to trust my heart because I really think my heart knew all along when I was off my path, but like my brain resisted and I, really want that for my younger self and I want that for everybody just to learn how to listen I now call it living below the neck, and I don't think anybody, everybody's living squeezed up like a tube of toothpaste into their head.

And so that's what I would say to my younger self, trust your heart, live below the neck, and really embrace life from that deeper place.

Jeffrey Feldberg: Gabe, as you say that, once again, I'm reflecting on some guests I've had on the podcast, as well as some studies that have come out. And we've all heard of the saying, trust your gut, or intuition, or hey, Gabe, why don't you [00:48:00] sleep on it? And what science is showing is that there's an intelligence. There's an intelligence in our heart.

Actually, our heart is one of the most powerful organs, if you will, in terms of emitting waves out there. It's very powerful. It has its own intelligence. And so, to what you're saying, when you go within, There's wisdom there. And sometimes we do need to take a step back, maybe sleep on it, see how we're feeling and, go in that direction.

But well said. Well, Gabe, it's official. That is a wrap. And before we close things off, if someone has a question, if they want to visit you, they want to become a client, where's the best place that they can reach you online?

Gabe DeRita: You can find me at EffectiveConnection. com that's my website. And that's where I share a lot about my work. There's a page on there for Corporate Partnerships that has some case studies from some clients who have done these authentic relating trainings and some of the companies that I've worked with and the leaders that I've coached.

And you can read some stories there.

Jeffrey Feldberg: Terrific. And for our listeners, it's point and click, doesn't get any easier. Well, Gabe, as we love to say here at Deep Wealth, thank you so much. And may you continue to thrive and prosper while remaining healthy and safe.[00:49:00]

Gabe DeRita: Thanks, Jeffrey. It was a pleasure to be here. Appreciate your time. 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. What did you think? So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. Did you find this episode helpful? Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

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