From Success to Stuck: How to Reclaim Your Business and Your Life with David Hochberg - EP07

From Success to Stuck: How to Reclaim Your Business and Your Life with David Hochberg

In this episode of The Wealth Clock with Steven Weinstock, I sit down with David Hochberg, a trusted advisor to business owners, founders, and CEOs who built the companies of their dreams, only to wake up one day and realize they feel trapped inside them.

We talk about what happens when the business you built no longer reflects who you’ve become—and how to break free from that quiet frustration. David shares the patterns he’s seen over decades of advising leaders, how to navigate moments of transition, and how to realign your work with your values.

This is a conversation for anyone who’s built something big, but feels like something’s missing.

We cover:

• The moment successful founders realize they’re stuck—and what to do about it
• Why growing a business can sometimes leave you feeling smaller
• The mindset shifts required to take back control of your business and your life
• Practical steps to reconnect with your original vision

Tune in for an honest, eye-opening conversation about business, fulfillment, and the freedom we all chase.

🎙️ Guest Spotlight: David Hochberg

Name: David Hochberg
Title: Strategic Business Advisor | CEO, DH Group | Former Mortgage & Radio Host
Website: dhochberg.com
Email: david@dhgroup.com
Phone: (410) 764‑2029 

About David:
With over 25 years blending psychology and strategic business insight, David helps founders who feel "stuck inside the company they built." He’s a trusted advisor for business owners, CEOs, and founders navigating growth, transition, and reclaiming agency 

Connect with him on LinkedIn:
linkedin.com/in/david‑hochberg 

🎙 About Steven Weinstock
Steven Weinstock is a real estate investor and founder of WeCapital and the Goethals Capital Fund. Since 2001, he has built a diverse portfolio of residential and multifamily assets while helping investors access passive income through strategic real estate opportunities. On this podcast, he shares real-world insights on investing, capital raising, and what it really takes to build and scale in today’s market.

📩 Want to invest or get in touch?
Visit: www.WeCapitalX.com

📱 Connect with Steven:
LinkedIn: www.linkedin.com/in/stevenweinstock1

Instagram: https://www.instagram.com/wecapitalx/
YouTube: https://www.youtube.com/@TheWealthClockPodcast

Transcript

0:00

Hi everyone, and welcome to the Well Clock with Steven Winestock. I've been investing in real estate for over 20 years. Started with single family homes, now moved on to multi-family properties and launching my own real estate investment fund. This podcast is brought to you by WE Capital and the Golf's Capital Fund, where we buy properties in cash. We lock in deep discounts, and we eliminate the mortgage risk. We later refinance so we can scale up all without asking investors for more capital. This show is not a Boun me, it's about operators, founders, closers, other producers, other leaders in the business industry. Today I'm sitting down with David Hochberg, a strategic advisor to founders and business leaders who've built companies they once dreamed of, but quietly and realized those companies no longer reflect who they've become. David brings more than 25 years experience at the intersection of a psychology and business strategy, helping clients find and fix misalignments at the root. His work is sharp, personalized, and designed to help leaders make bold, clear decisions with integrity. We're going to get into some deep waters today, intuition, identity, goals, and the emotional side of money. David, thank you very much for joining. Honor and a pleasure, Steven. Thanks for having me. Okay, we're gonna go right into it. I have a question for you. When you deal with a founder who says to you, I no longer trust my gut, what do you tell them? Oh, that's a great question because that leads into one of my favorite topics, which is intuition. Everyone has intuition and it, I believe it's the most powerful tool you have to make decisions. I'm gonna say a gonna sound like a farfetched guarantee, but I will stand behind it and have a challenge. Anyone who, who disagrees, it gives you the absolute best decision 100% of the time, not 99% of the time. Once you can identify your intuition, once you can identify your gut, once you can learn to trust it, it gives you the best decision 100% of the time. It can't predict the future. No decision. You can't. Of your choices of decision, it gives you the absolute best decision. So when a founder tells me I can't trust my gut, that's one of the first things we have to get into. Learning to do that again.'cause that clears up a lot of things. Do you think intuition is something we're born with or something we're able to learn or relearn? I think we're all born with it. And again, there are many different definitions of intuition. The one I use is intuition is the sum total of all the information in your head. I. Everything you've learned, experienced, heard, read, knowledge, you picked up everywhere, brought to bear in one moment on the particular challenge that you have in front of you. That's how I understand intuition. So everybody's got that. The problem is the intuitive voice gets lost. It gets lost. I give this analogy. Imagine a giant conference table, right? 50 people around the conference table and you're sitting at the head. Your intuition is sitting immediately to, to your right. You have a question, should I go into this partnership with this person? Should I hire this a new employee? Should I go forward with this project? Your intuition quietly answers that question, and then everyone around this giant table, all 50 people start yelling at you. This one was the voice of that time that you jumped the gun on a decision and it came back to bite you. It's screaming at you, don't do it. And this one is the voice of your fear of being afraid that you know this is gonna fail. And this one is the voice of the excitement that loves every shiny new item and says, let's go. And that one's screaming and they're all screaming very loudly. And your intuitive voice, which is quiet, gets, you can't hear it over the noise. You just can't hear it. So everyone has intuition, but what winds up happening is most people don't. Know how to identify that voice over all the others because it's the quietest one. Most founders pride themselves on being either analytical and decisive. Where does intuition fit into that picture? It's a good question. I think to, you talk to people, you ask someone how to make, how do you make a decision? So most people will say, you make a list of the pros and cons, but when you actually talk to people about it. It doesn't leave them more confident about their decision. They're either making a list of pros and cons because they're trying to reinforce what their intuition already notes, or they're just as confused after they write the list. And if that doesn't work, then they go find the next support for one of the, one of the sides of the one, one of the directions they're thinking about. People who are analytical are simply taking what I believe is their intuitive answer. Then applying analysis and they will come to the exact same conclusion. That's why I really stand behind it, that once you identify and can use your intuition, it gives you the best and best decision 100% of the time. Now, just a key point about that intuition can't give you information you don't know. If you put me in the cockpit of a, of a fighter jet and said, fly the plane, my intuition would say, I don't have enough information. I can't intuitively fly, fly a plane. If I don't have the information, but my intuition is wise enough to tell me you need more information to answer the question, so you never have to worry that your intuition's taking you in the wrong direction. If it doesn't have enough information to answer the question, it will tell you that. Can you share a story either on your own or from a client? And feel free to share names, but I understand if you know where ignoring intuition led to a costly consequence. Sure. Just off the top of my head, and this is a pretty common one, people will hire, will go into a partnership where they will hire a new team member and they have their red flags. There's something in their gut that tells them, be careful this isn't the right move. They go ahead, they ignore it, they do it anyway, and they discover three months, six months, or even two weeks later, that this hire absolutely made a mess of things. And it's much more difficult for them to get out of it. The longer you push, the longer they push off that decision, the more difficult it is to extricate themselves from it. So that's a common one. The wrong hire, the wrong partnership that you knew wasn't right for you, but you did it at a lot of the people. A lot of people assume that once you have money, everything else gets easier. What have you seen in practice in your dealings with company founders? Successful, uh, successful business owners, money makes you more who you are. If you are a very giving kind person, you're going to use your money in a very kind and giving way. If you are a very self-centered, narcissistic person, you're going to use your money in a very self-centered way, and money simply amplifies your identity of who you are and money simply options. So you have more options. You do more. Of who you are, but it doesn't change who you are. What are some of the hidden beliefs about money that keep founders stuck in their position? So a common one is just the belief, I would say it has less to do with money and more to do with just the concept of being successful in the way that they want to be successful. This is an actually interesting thing. If you ask somebody, do you wanna win the lottery? So everyone's knee-jerk reaction is yes, but very few people will actually sit down, think about that question, and really envision what their life is gonna look like if they win the lottery. And what you'll find is it brings its own set of stress, its own set of challenge, and its own set of all kinds of demons. You didn't even know you had. Because our relationship with money is really like everything else in life. It's determined very early on our experiences, what we learned, what we saw, and what we went through in regarding money. And then that doesn't necessarily change just because you now have a lot of it. So I think our beliefs are set very early on and then it takes work to change them. They're changeable, but it takes work and it takes awareness of recognizing that, that you're gonna be who you are. So you may have a lot of money, but you're going to be who you are and if you want to change your relationship with money, you have to change the way you view it. David, I'm gonna ask you some personal questions here. Obviously, I'm not gonna ask your social security number or, or your current net worth, but what's a belief that you held earlier in your career that you've had to unlearn? I had, I, so my background's in the world of psychology and therapy, and I always wanted to own a mental health clinic. I went through a lot of the motions and I went, I hired my leased office space. I hired staff. I hired clinicians. I, I was building it, but it, I kept finding myself getting stuck at a certain point because it wasn't something that I really wanted to do. So what I personally found is I would build things to a certain point and then I would stop. So that was one interesting belief I had to unlearn that recognized that. What you really want to build and your greatest success financially and in every other way is going to come when you are completely aligned with what you believe and what you're actually doing. People get stuck when what we think we should be doing is up with what we're actually doing. Another one I found is that, that if, that I, if for me, it needs to flow. The money needs to flow. The sales need to flow, the contacts need to flow, the project needs to flow. And if I am bumping up against something and it's not flowing, I find that I have to take a giant step back. I. Really look at what I'm doing because there's something I'm doing, which is not, I'm stopping myself in some, somewhere along the road. I'm pulling over from the side of the road at some point, and I have to figure out exactly where that is and what that is. But I've noticed that the, the concept of it flowing is very important for me. In your business, you are speaking with successful people for the most part. And when you deal with successful people, they typically assume or they think that they're the smartest person in the room. What are some of the challenges you have when you speak to these people to get them to be more honest about some of their mistakes? I find that I tried people who believe they have all the answers. I try to discourage them from working with me. I tell them that if you believe the answer is that you want to continue doing this and you want to keep going in this direction, go right ahead, but we're talking because it's not working. We're talking because you're bumping up against something and you might even not, you might not even know what it is, but you're bumping up against something. I highlight the disconnect. I highlight the misalignment. I highlight what they're doing. That reflects something's going on someone, one of the things that I, I tell founders, just, you're circling a move for two months now, if you knew what to do and you believed what you were doing was the right thing, you would've acted a long time ago. You've been doing it your whole life. You've been doing it with every other stage of your business. Why are you stuck? Now? I highlight the disconnect between what they're telling me and what they're doing. That's probably the most powerful tool. You ever find that you have a client who I, I guess they already agree with what you're telling them, but they just need to hear it out loud and maybe from somebody else. Just to give an example, I, I need to lose weight and obviously I know I need to eat right and exercise, et cetera. Now, if I were to go out and hire a nutritionist, I feel that. The only reason I'm gonna be listening to that person is because I'm spending money and I'm paying for this advice, so therefore I'm going to take the advice because I'm shelling out $75 or$150 a visit just for them to tell me, eat less pizza and eat your broccoli. You ever find that you really just almost like the inner, the inner angel for these people, and you're really just telling them what they already know. Or is it, are you really telling them something totally new where they totally didn't realize what was going on and you highlighted something that is so refreshing to them that they're gonna take your advice, et cetera? So. Two points on that. Number one, I've found that even when people pay money, it doesn't mean that they're ready to necessarily hear what you have to say. I can speak personally, I know I, over the years, I signed up for, spent a lot of money on different marketing courses and different branding courses and different things like that, and I wouldn't show up to any of the calls, and I did absolutely nothing with it. Because even though I was spending a lot of money and you'd think that would be the motivator, it wasn't, I wasn't ready. It just, it wasn't connect, it wasn't aligned for me. So number one, I don't always believe that paying money or paying a lot of money is a real motivator. It's a, it's a very superficial motivator. And the minute the pressure is off of the money, the minute you're finished, whatever it is, the minute you stop paying. You are right back where you started from, and nothing really fundamentally changed for you. So that's one thing that I've, one point I'd like to make. The second point is I find that often, and it happens more often than not, I'm not sharing anything with them that they don't already know, but I am allowing them to bring it out into the open. And we both look at it and it's very clear to them. And there are different ways to do that. For example, one of my, one of my favorite techniques is one that I actually found in the book Atomic Habit. I had been using it be before I could tell the book, but it's one that he uses in there and it's a very powerful one. The question of behavior change is not long lasting change. I'm not going to eat. Pizza is not long lasting change. I am a person who eats healthy, so then naturally what happens is I'll eat less pizza. So the identity change is much more powerful than the behavior change because if you say, I'm gonna eat less pizza, no I'm not. I want eat pizza. I enjoy it. So that's what I'm going to do and I'm gonna have that battle in my head. But if I'm a person who is as healthy as I could possibly be, then I will come to the conclusion on my own and create the behavior change that I'm not gonna eat the pizza. And I find that's a very powerful tool for people. In other words, who are you gonna be? I just had this conversation with the founder recently. I said, who do you need to be to build the next level of your business? Who do you need to be? Not the specific steps. You're smart. You built the first stage. You'll be able to figure out the second stage. I'm not worried about that, but who do you need to be to build the second stage? Then he started to say, I, I need to be more confident in whatever it is. I need to be less afraid of the market. I need to be less afraid of testing the market. I need whatever it was that he said he needed to do. Then he created the behavior once he was plugged in to who the identity is and who he needed to be to get the goal he wanted to reach. And how, you mentioned you signed up for branding courses, marketing courses. What are you doing today? I know you're from LinkedIn, you're active on LinkedIn. We all know the best business comes from referrals. What are you doing to market your business, your talents to others? So I use LinkedIn a lot and I use, have conversations with people. I try to have a lot of conversations with people and I find that networking just on LinkedIn and in the dms and like you and I, we connected just over over LinkedIn and I try to do a lot of that. I find that that's helpful and I. It teaches people what you do. And this person knows somebody who knows somebody. And referrals roll full flow in. Now we all know sales, so to speak, is a numbers gang. You'll reach out to a hundred people. 90 might ignore you, three might 10 will respond, three will engage, and maybe one you'll get, they'll get hired, et cetera. And obviously those numbers vary. How do you not lose focus? How do you not lose? The passion to go out and try to connect with a potential stranger and not get bogged down by the rejection and just keep going and keep doing it. Because this applies really in all businesses. There is a level of sales. Uh, I was just having this conversation with my son, who I'm trying to convince him, uh, to a law school. He's told he's just graduated high school and you know, I'm trying to tell him that being a lawyer, you're also a salesperson. And he didn't understand that. And I said. You have to go out and try to get coins. Oh no. What if I work for a big corporate firm? Then you have to go out and just try to engage with your coworkers, like in some sort of sales strategy, so to speak, so that they like you, so that they give you the right jobs. Sales is really in every aspect, every business, so it's great that you're bringing that up because I went through a period fairly recently where I was going back and forth between the concept of volume. Versus the volume leads versus the quality leads. What am I looking for? Am I truly looking for a numbers game, reaching out in mass and really trying to run the numbers? Or am I really looking for the person who I connect with? I understand their problem well, I believe I can really help them, and they believe exactly the same thing. I was actually going back and forth and in different directions to try to find, and I've discovered for myself, and I think this is probably true of most people, for myself, the best sales approach is the more targeted, warm approach. And I think in general, you use the word sales. What's your gut reaction when someone says, oh, are you in sales? What's the, what does the word sales make you feel? So in general, I'm supposed to answer and say, no, I'm not in sales and sales. I'm thinking a guy is selling used cars. A guy is making cold calls every day to sell some sort of product. In my old life, in the late nineties, I was doing sales, I was selling advertising. I didn't go around saying I'm a salesman. I went around saying, Hey, I work on Madison Avenue. I'm coming up with great campaigns. But in reality, I was a salesperson, and even now in my business of real estate. I am in sales, whether it's selling myself to the best brokers out there so they could send me the good deals, not just send it to their favorite clients. I need to impress investors or potential investor. I need to impress everybody because everybody is a potential investor for me. Everybody is a potential referral for me. Now, how I answered that question years ago is a lot different than I would probably answer it over the last five, 10 years. But yes, the answer you're looking for is, no, I'm not in sales. Sales is a guy who sells ad space and is local or classified ad such. But yeah, everybody's in sales. Uh, to some degree you're a hundred percent correct and I think the biggest change people can do in their own head. The word sales, and that's what I was looking for. Like I said, when you say sales, you're thinking used car salesman. You're thinking what you're saying because they think of the more, the sleazier side of sales. Probably one of the most powerful things you could do is if you just replace the word sales with a word, which is more useful and in line with what you're saying, it can be. You are in, you're helping people. That's all you're doing. If you look at your sales calls. Literally and sincerely that you are trying to help someone and as if you got, if you're talking to a broker or you're talking to whoever you're speaking to, and you genuinely are interested in seeing if you can help them, you're not selling, and yet you're going to come across knowledgeable, experienced, and enjoyable to work with. And you can have a lot of the positive factors that the any, that any sales course or sales training will teach you. That's gonna come across naturally because the idea of sales, because there's so many people out there who abuse the concept. The idea of sales turns people off, but substitute a different word in your head. You've worked with people who've made it. You're dealing with people who are not broke. For the most part, you're dealing with people who have extra money to improve themselves. These people obviously still feel a bit off if they are going to hire somebody to help them improve. What makes them feel the need to seek help. Even though they have money, they're paying the bills, they have their two cars, the beautiful house, the beautiful family, they're going away for Passover, but what makes them decide to reach out and try to get help to try to improve themselves? They're noticing, probably one of the first signals they see is their fire is dying out. They're not on fire the way they used to, you know? And they might be going through the same motions, running the same meetings, doing the same things, but the fire is dying and there's a reason for that. That's usually the first clue. Does that mean you're dealing with people in a certain age bracket? Are you dealing with 26 year olds or are you dealing with somebody who's 42? They've been successful for a number of years. Uh, I'm dealing with people age 35 and up generally. See someone who's in their twenties is still on fire and they're naturally on fire. They're just naturally on fire, and they're also new in the building process of what they're building. Even if they built their business, it's. A couple years old. It's not, not, hasn't been around for 15 years. They haven't been doing the same thing. And therefore what winds up happening is they have a natural fire. So they're just, they're, they get up every morning, they're ready to go. And someone who's been doing this for a while, and they're still doing it and it's working and that's the biggest challenge is that what they're doing is working. It isn't that the business is failing, the business is working, but something has changed with them. They're less interested. Something about it is just the fire's going out. So it's not just a function of time, it's a function of misalignment, but nobody sees it at, see, that's the conversation that all they see is the fires going out. All they see is that they have the same decision, they're circling the same decision. Their team says, are we moving on this or not? And they say, we're doing strategic due diligence here. That's what they see, and that's why they come to me. What's really going on is something almost always much deeper than that, and that's the first question I ask them. I say, why are you circling on this decision? You've made a hundred other decisions more complex than this one. Why are you circling this one? And that's where the conversation begins. Yeah. In real estate, we call that analysis paralysis. We're just gun shy. Maybe they had some rough patches and they were just afraid to move on to the next level or to chase another deal. Exactly, and that's, you get a couple times, you're gonna be careful and that's where intuition comes in, because your intuition will say to you, this deal is a solid deal. I can be afraid of doing it, but that doesn't change my intuitive analysis of this and this is a solid deal. Why does certain goals that once excited us sometimes start to feel irrelevant or even a burden we change? That's just the, the answer. We change what was important to us in the past might not be as important. New things become more important and our goals just as just chart that through life we change. And that's usually what happens. The gold usually doesn't change. We're the ones who change. You work with successful people for the most part. What kind of goals do they secretly regret chasing? I like that question. I. A goal that they secretly regret chasing. So I'm gonna have to think about that one. A goal that they secretly regret chasing. I think a lot of what their regret is, they knew it was the wrong decision, and that can be different things. They knew it was the wrong move. They knew they shouldn't have opened up a branch in this particular city. They knew those things and they regret doing it. But in terms of a theme of a goal, I have to think about that one. Yeah. Yeah. You operate at the intersection of business and psychology is what I said in intro. What do most leaders or most of your clients miss about their own thinking? What are they, what mistakes are they making most commonly? So I would tell you the two biggest mistakes where people get themselves in trouble is fear and ego. Fear and fear can come in a lot of different forms. There's something that they believe is the right move. They're afraid of something. They're afraid the ripple effect it's gonna have, they're afraid what it's gonna do to their team. They're afraid what it's gonna do to their business. They're afraid what it's going to do to their market. The ripple effect of whatever it is. Fear is a big one, and ego is another one because you're dealing with people and if you're managing people and you have to always, they get themselves into trouble. And we all do this because we, we like to think that we know what we're doing. We like to think that we have it figured out. We like to figure, we'd like to think that at the meeting, we are the smartest people in the room. Listen to everyone else. We won't say this out loud necessarily, but we're thinking and we're talking to somebody and we're already thinking what we're gonna say next. Even though they may have something valuable to add, and I find that gets in the way. David, this was incredibly insightful. I appreciate your clarity, your perspective, and how direct you are with these topics. People avoid, most people avoid these topics. For anyone who's listening, who wants to dig deeper or work with you where they reach out, tell us your company name, website, any, anything you wanna say. LinkedIn is really the absolute best way to reach to find me. Okay. To our audience, thank you for tuning in to the Wealth Clock with Steven Westock. Make sure to subscribe, leave a review, check out some other episodes. We speak to real operators. We're having real conversations and these people are doing the real work and we'll catch you on the next one. David, thank you so much for visiting and hope to see you on LinkedIn. Thank you very much, Steven. Thanks for having me. No problem.