March 25, 2026

Former Wall Street CFO Ruchi Pinniger Exposes Hidden Money Patterns Destroying Profit & Peace of Mind (#528)

Former Wall Street CFO Ruchi Pinniger Exposes Hidden Money Patterns Destroying Profit & Peace of Mind (#528)

Send us Fan Mail “Appreciate the loved ones in your life.”-Ruchi Pinniger Exclusive Insights from This Week's Episodes Profitable founders do not always feel secure, and that gap can quietly damage pricing, decisions, and peace of mind. Former Wall Street CFO Ruchi Pinniger reveals the hidden money patterns behind that tension and why the real breakthrough starts inside. Listen now. EPISODE HIGHLIGHTS [00:04:00] Ruchi shares the Prada bag story and reveals the costly lie that external success...

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Send us Fan Mail

“Appreciate the loved ones in your life.”-Ruchi Pinniger

Exclusive Insights from This Week's Episodes

Profitable founders do not always feel secure, and that gap can quietly damage pricing, decisions, and peace of mind. Former Wall Street CFO Ruchi Pinniger reveals the hidden money patterns behind that tension and why the real breakthrough starts inside. Listen now.

EPISODE HIGHLIGHTS

[00:04:00] Ruchi shares the Prada bag story and reveals the costly lie that external success creates internal prosperity.

[00:06:00] She explains why business revenue will never outperform your relationship with money.

[00:08:00] Ruchi introduces her RIR method, Recognize, Interrupt, Reframe, to break disempowering money thoughts.

[00:20:00] She exposes how undercharging and trading time for dollars quietly cap growth and create burnout.

[00:28:00] Ruchi explains why founders can be profitable yet still feel broke, and why profit is not the same as cash flow.

[00:30:00] She names the hidden cost of bad financial visibility: anxiety, poor sleep, and weaker decisions.

[00:33:00] A client story reveals how childhood money patterns can drive overspending even after revenue grows.

Full show notes, transcript, and resources for this episode:

https://podcast.deepwealth.com/528

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00:00 - Prosperity Beyond Numbers

03:07 - Podcast Kickoff Abundance

03:46 - Ruchi Origin Story

05:51 - Beliefs Drive Revenue

08:30 - RIR Mindset Tool

10:55 - Wellbeing Creates Joy

13:12 - Healthy Relationships Money

15:51 - Contentment Over Chasing

18:04 - Unlearning Worth and Wealth

20:09 - Pricing Value Not Hours

21:50 - Proving Yourself Mindset

22:56 - Working With Watcher Prosper

23:24 - Financial Partner Model

24:52 - Founder Bottlenecks

25:41 - Bookkeeping Rescue Story

27:23 - Cut Costs Fast

28:39 - Profit Versus Cash

29:46 - Hidden Anxiety Costs

31:02 - Money Shame Origins

32:26 - Beliefs Drive Behavior

34:25 - Team Abundance Contagion

34:52 - Reticular Activating System

36:59 - One Action Today

39:05 - Giving Through B1G1

41:10 - Prosperous Life Calculator

43:04 - Back To The Future Wisdom

44:25 - Phoenix Through Loss

46:17 - How To Connect

47:05 - Subscribe And Support

48:53 - Final Thanks And Farewell

528 Ruchi Pinniger

[00:00:00]

Prosperity Beyond Numbers

Jeffrey Feldberg: What if financial clarity wasn't about spreadsheets, but about self-worth? Ruchi Pinnegar is the founder and CEO of Watcher Prosper, a modern financial services firm on a mission to help women entrepreneurs build profitable, scalable businesses without burning out or second guessing every decision. 

But Ruchi didn't start here.

Her journey began inside the world of traditional accounting where numbers ruled the conversation and founders were often left, overwhelmed, under, informed, and quietly ashamed of what they didn't know. She saw brilliant women building impactful companies while privately struggling with cash flow, pricing, payroll, and fear.

Instead of accepting that as normal, she built something radically different. Watch her Prosper Blends Financial strategy bookkeeping, CFO, support and Education into a People First experience designed to empower women to understand their money, not hide from it. Ruchi's work sits at the intersection of profitability [00:01:00] and power.

She helps founders move from reactive to intentional, from guessing to knowing.

 Her mission is bigger than balance sheets. It's about shifting how founders relate to money, leadership and their own ambition. 

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 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 [00:02:00] 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 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 C E S 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 [00:03:00] 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.

Podcast Kickoff Abundance

Jeffrey Feldberg: Deep Wealth Nation, welcome to another episode of the Deepp Podcast. Well, deepp Nation, let me ask you a very upfront and personal question. What's your narrative specifically when it comes to abundance? Money prospering doing well? Do you even have a narrative? Maybe you're not even aware of it, and if you're saying, Jeffrey, Jesus, I'm not so sure, or It's not so great, or I don't feel so worthy, guess what?

We have a very special guest in the House of Deep Health. You heard the official introduction. Richie, welcome to the Deep Health Podcast. It's an. Absolute pleasure to have you with us. There's always a story behind the story, and you have quite an interesting story. So what's your story? What got you from where you were to where you are today?

Ruchi Pinniger: Yes. Well, great to be here. 

Ruchi Origin Story

Ruchi Pinniger: Let's rewind on that story. So, Thinking about me as a young girl, I was the daughter of immigrant parents, mostly a single mom, which imagine back then, in the eighties growing up here with a single. A mom from [00:04:00] another country that was not the norm. And one of the things I really noticed, first of all, is obvious how different I looked, how different I felt.

But I also, I. Would see all of my classmates and my friends with all the designer things. So I thought the designer things meant happiness because that's what I saw on the outside. They were all happy. They had the white picket fences and the, both parents and they look like they fit in.

And I thought, well, I guess I need those designer jeans. Back then it was the DoorDash jeans. I don't know if y'all remember those. You might have your own version of those growing up. That was mine. And so now fast forward, I get onto Wall Street. I'm thinking I finally made it. I'm successful. I have money now, and I buy my current version of the DoorDash jeans.

It was the Prada bag. I thought, oh, my Prada bag's gonna change everything. I feel so much different now. Of course, yes, I got the dopamine hit, but guess what? Nothing changed. My bank account changed, [00:05:00] but that's it. And I had a pretty bag, but I felt the same inside. So that was that moment of realizing it's not about the outside.

Prosperity is an inside job. So through this work at Watch Her Prosper all these years later, working with thousands of people, I have created my framework, which is my three pillars of redefining prosperity, and I help people to see prosperity in a new way.

Jeffrey Feldberg: Deportation. As you're listening to this, I'm now speaking specifically to the quote-unquote guys out there in DE Nation. I have a confession. Personally I've always found that the women tend to be a little bit smarter than us and do things a little bit better. And although Ruchi focuses on women founders, guys, we have a lot to learn.

So listen up. This does not exclude you. If anything, it's inclusive, not exclusive. And listen up to what's going on out there, because Ruchi has some incredible things to offer. 

Beliefs Drive Revenue

Jeffrey Feldberg: And so, Ruchi, let me ask you this from a very high level. One of my favorite questions in this kind of scenario, it's PATOS Law, what some people call the 80 20 principle.[00:06:00]

And it goes along the lines for palpation if you're not familiar with it, that as an example, 80% of your profits might be coming from 20% of your clients, and sometimes it's not even 80 20, it might be 90 10 or 95 5. Richie, in your work when you're working with founders, entrepreneurs, business owners, when it comes to, I'll take the glass half full for just a moment, the challenges, I call them opportunities.

Are there patterns there that, yeah, Jeffrey, 80%, 90% of challenges are actually coming from the 15 or 20% of these issues over here. What would be some of the bigger picture patterns that you're seeing that perhaps are holding us back?

Ruchi Pinniger: Absolutely it is our beliefs. What I always say is, your business revenue will never outperform your relationship with money. So I have seen so many times where everything looks great on the outside, the money's there, but there's something deeper down that is not right, that needs to be looked at. Work through.

And then once we work through what's deeper, the beliefs, that's [00:07:00] when we were able to really increase the revenue. So for example, we have people who don't trust themselves with money. So I can tell you a story, for example, about Mary as a young girl goes to the mall, her parents. Going for a mattress and she goes to the arcade, she's playing video games.

They come over, Mary, it's time to go, honey, let's go. She goes to grab her bag and guess what? It's there. It's empty. So instantly in that moment, Mary doesn't trust herself with money that shows up for decades in her business. She doesn't feel like she, can charge the rates she needs to charge. When she does make money, she spends it immediately.

She doesn't have money for taxes. It has impacted her. She spends tens of thousands of dollars on therapy. It's when she realizes, huh, I'm carrying this with me. I don't trust myself with money. That's the shift. The awareness is the beginning.

Jeffrey Feldberg: And what's interesting as you're talking about that Ruchi, I'm going back to a classic book, Napoleon Hill Think and Grow Rich, [00:08:00] and he puts it out there very early for his time, actually ahead of his time. He says, thoughts are things, and so in other words. What we're telling ourselves, that mental chatter, the internal narratives on the inside that manifests our inner thoughts becomes our outer world.

And for someone in Deep Nation, they may not even be aware of the prosperity or lack thereof of the narrative that they're telling themselves. How do we begin to find what our narrative is when it comes to abundance and prosperity or lack thereof?

RIR Mindset Tool

Ruchi Pinniger: First of all, we start to pay attention. So the awareness is the start. We have an average of six. Thousand thoughts a day. 80% of them are negative. Imagine what would shift in your life if 80% of your thoughts were positive. So I wanna give everyone out there a tool so that they can actually keep this in their head and start to pay attention.

This is actually one of our three pillars is spirituality, and it's really paying attention to your thoughts. If all day you're thinking about lack and [00:09:00] scarcity, what do you think you're calling in? Lack in scarcity, right? So think the things that you want to be not necessarily what you feel or believe is reality.

So start to look at your thoughts. Recognize, interrupt. Reframe RIR. So that's my RIR method. Recognize the disempowering thoughts you're carrying with you. Interrupt them. Take a breath. Is this truth, reframe them. So something like a thing that I hear so often is it's so hard to make money. A lot of us come from parents who tell us, you have to work really hard to make money.

And we don't realize, ah, I can actually make money with ease. So that, that recognizing the thought, it's so hard to make money and reframing it with something like, wow, I'm so grateful for my abundance. Money flows easily to me. And the biggest thing about this, it's not just the thought, it's not just the words.

It's how does it feel in [00:10:00] your body to feel so abundant, to know there's always enough to pay the bills, to know that everything you need is available to you. What does that actually feel like? And that's the missing piece in mindset work, the body, the feeling.

Jeffrey Feldberg: Okay. And so you put one of the pillars out there. Let's talk about the other two. I know the wellbeing and the healthy relationships are also interconnected. I love how you single them out. So you started with spirituality and I'm sure for some in Deep Wealth nation, they're saying what? Spirituality in business.

Don't think so. And I gotta tell you, deep old nation, the further we get along in our science, I'm not gonna call it religion, I'm gonna call it God, I'm gonna call it the universe, whatever you'd like to call it. Science and God are merging to become one in the same. There's really no difference.

The quantum field or the field, you may have heard of some of these terms. It's fascinating what's going on. So from spirituality you put out there as the first one, where do you wanna go next? Wellbeing or healthy relationships.

Wellbeing Creates Joy

Ruchi Pinniger: Yeah, let's go into wellbeing. I also just really wanna quickly echo what you [00:11:00] said. Spirituality doesn't have to be complicated. It can be whatever you believe is out there supporting you. As you said, Jeffrey, God, universe, source. And if none of those connect, it could just simply be your higher self, like your next level.

Okay, so wellbeing. I know a lot of us think about eating right, exercising right, all of that. And yes, that's wellbeing. But I want you to think bigger about wellbeing. I want you to think about what really brings you joy, incorporating that into your life. Because we have this society where a lot of us.

What we feel about ourselves is based on how wi busy we are. If you think about when's the last time you ask somebody how are you? And they said, oh, I'm so busy. That's by the way, not a feeling. That's not how you are. So really thinking about what are the things that you love to do that you've stopped doing, that you haven't.

Prioritize. So for me, I'm here in New York City. I love my long strolls in Central Park. I took one this morning listening to music, nobody bothering me. Just really feeling like I was caring for [00:12:00] myself and doing something that I love. I love my regular massages. I don't need to wait until I'm on vacation or at a resort to get one.

I go when I feel like I want to go. So thinking about how can you incorporate the things that you truly love that have fallen by the wayside and. Getting them on your calendar because later is not on the calendar.

So that's I, love that, we're speaking to prospective members of the Deep Health community. Yeah. Jeffrey, I'll get to it tomorrow or I'll get to a little bit later and I'll share with them last time I checked. There is no tomorrow. There is no later. Let's talk about right

I love that. I love that. I love that. And you know what that is? That's their mind. Like wanting to keep them the same. Our minds are wired to keep us the same, which is why we call it the comfort zone. Anytime we're thinking about or making a decision that would expand our comfort zone. It's trying to push us back to the old way because that's where it's familiar. So anybody who's thinking about Deep [00:13:00] Wealth Nation now, you know the science behind why you're not making that decision to move forward.

Jeffrey Feldberg: And for the ones that are in deportation, congratulations. You broke the status quo. You did the unknown, the uncomfortable. And here you are. 

Healthy Relationships Money

Jeffrey Feldberg: And actually it's a great segue into the third pillar healthy relationship. So what's going on there? What would you want us to know?

Ruchi Pinniger: Yeah. Thinking about healthy relationships, both with people and with money. Thinking about people first. You've heard that saying you are the average of the five people you spend your time with. So think about this as just simply a reflection point of who are you spending your time with?

What are those relationships based off of? Are you gossiping, complaining, or are you lifting each other up? Rising each other, connecting each other, celebrating each other, allowing each other to brag, just really having those moments and also thinking about what are the money habits of the people you're hanging around with.

Are they aligned with your next level version of you, or are they back there where you've already been? Meaning are you [00:14:00] having to pretend sometimes you're having to pretend to keep up? It could be both ways. It could be that, maybe everyone you're spending time with. Has lots of money and they're going on big vacations and you maybe aren't in a place where you can, afford that right now.

And that's totally okay. are you sharing that? Are you being open about it or are you just pretending it could be the other way? You have so much more and you're pretending like you don't. So just start to pay attention because I always say those money habits can be contagious. So that's people piece.

Jeffrey Feldberg: Yeah, Ruchi and putting myself under the microscope. I have been on both sides of that coin, and I gotta tell you, at least for me. There's one side of the coin to not be on and one side to be on. And when I look back at that, it is like another saying, birds of a feather flock together or frog in boiling water.

And when I was in no judgment here, when I was with a certain group of people whose values at the beginning weren't aligned with me. With my values going into it. Little did I notice that I began to [00:15:00] change as a person, my thinking process, my values, everything else that went along with that. And lo and behold, I caught myself moving away from who I was at Equilibrium Point, if you will, and going down a path that was not becoming of me.

And wow, it's hard to start momentum. It's also hard to stop momentum and get back to center. And so Deep Nation. Who are you spending the most amount of time with? If you zoomed out, and again, no judgment here, you looked at those people, would you be walking away saying, wow. What terrific people, incredible values, what a great example they are.

Or you're walking away saying not so sure about that. Because if that's who you're spending your time with, then heads up, you're likely gonna become more like them. And is that what you want to be? Is that what you want your legacy to be like your business will be like? So you've walked us through this spirituality, the wellbeing, the healthy relationships.

Contentment Over Chasing

Jeffrey Feldberg: I wanna go back to something that was subtle. But also important. You mentioned joy, and I'll often use joy or gratitude, even [00:16:00] fulfillment. In fact, one of my sayings here at Deep Wealth and Deep Wealth Nation, success without fulfillment is failure. So all the zeros in the bank, all the accolades, all the accomplishments.

If you're not fulfilled and I'm using fulfillment over happiness very specifically, then something's missing from that. So I really love how all three pillars. Begin to point us towards that joy or that fulfillment. We'd love your thoughts on that.

Ruchi Pinniger: I love that. I talk a lot about contentment because of the way we are in society. We don't even stop to celebrate our successes. We, It's a check the box. It's a to-do list. Oh, I got to hear, I get to do this. I got to do that. I won that award. I made this amount of money. I closed a new client.

Next thing. about just pausing and like reflecting on, wow, what did I accomplish here? How much have I done and How am I feeling? Am I feeling really content? if this were my life, would I feel really good? That's something.

Jeffrey Feldberg: big question. Yeah.

Ruchi Pinniger: Yeah. Yeah, because it doesn't always have to be [00:17:00] about chasing the next thing.

Sometimes it can just be there's mornings I wake up and I literally say to myself, oh my goodness. How beautiful my life is. Like really, truly how beautiful my life is, how grateful I am for this life. for the family, for the support, for the, the home to be able to pay the bills for health, for all of it.

Now when's the last time you really were able to just pause and step back And say that to yourself. And if you're not, that's also okay. 'cause that's just information. So this is important for all of you. This conversation. It's not about judgment. It's about reflection. It's about awareness, and it's about looking at what it is you've created.

All the hustle, all the hard work to make six figures, seven figures, eight figures, nine figures. Sell the company, start the company wherever you are on your journey. Just look.

Jeffrey Feldberg: I couldn't have said that any better, Ruchi, what I feel so privileged when I have the opportunity to speak with founders [00:18:00] like yourself, and we're gonna talk about watcher Prosper and your secret sauce. 

Unlearning Worth and Wealth

Jeffrey Feldberg: Before that could happen though, you had to go through your own journey and in your own journey. If I can ask a personal question, was there a time when you look back, was there a specific belief about Wealth that you had to unlearn?

Ruchi Pinniger: I think it's that when I had my own Wealth, it's that everything would change, that I'd just be happy that I'd feel good about myself. That's truly what it was and it really relates to that Prada bag story and the DoorDash Sheen story. I realized that no matter what I have, look let me be real.

I love beautiful things, right? I do. I love me a Prada bag. I love me a Gucci bag, I Valentino shoes. Okay? I'm not gonna lie, I wanna be real with you. But the difference is they don't make me whole. That's not what makes me happy on a day-to-day basis. That was my biggest unlearning to know that no matter what I was wearing, that I am enough, no matter who I was talking [00:19:00] to or where I was.

I belong in that room if I choose to. So it was a lot about my own feeling of myself and my own wholeness that I had to work through.

Jeffrey Feldberg: Interesting. And as we talk about that on the business side of things, let's now. Position that on the business. So from the personal, okay, I'm gonna get this bag. I'm gonna feel whole life is grand, my problems are solved, look at me. So that feeling. Perhaps lack or not being worthy, whatever term you wanna put around that.

On the personal side, how was that beginning to show up on the business side for you? And the reason that I'm asking RCI for someone in nation that they're hearing us talk. Oh, Jeffrey, yeah, whatever. I don't care about bags. I'm not even a fashion, it's not my thing. That's okay. Deputation. It's gonna be something else for you.

But as we hear Ruchi of what she went through from the personal now to the business, something's gonna pop out. Oh my goodness. I never even realized that feeling that I have, that's where it's coming from. Wow. Now that I know that IPI can begin to either in a [00:20:00] good way, leverage that, amplify that, or Hey, it's not so good, perhaps I'm gonna begin to eliminate that and replace it with something else.

So how was that showing up on the business side for you?

Pricing Value Not Hours

Ruchi Pinniger: So on the business side, when I started, I was charging hourly. I was way under charging. I was thinking, I'm new at this, but actually I had over 15 years on Wall Street. And in finance, I wasn't really new at it, it was just a new business. And I think that's what a lot of us do. We create a story like we have to undercharge 'cause we're just starting, but actually you're starting because you're an expert already.

So that was where it started to show up where charging way too low and. Like literally trading time for dollars that if I'm not working, I'm not making money. And what I started to see is, yeah, I got to six figures, but at that point I was totally burnt out. I couldn't even take on more clients. And someone said, how do I connect people to work with you?

You're so great at what you do. And I was like, I don't even have capacity to take on more. Like I literally don't have the time. So it [00:21:00] was in that period where I started to reflect on how am I charging and really started to realize there's so much value in this work. It's not about the time for the dollars, like me being with a client and charging by the hour didn't make sense because I'm adding so much value into the work.

For all of you really who are maybe doing that, like really start to reflect on what is the value you're bringing? And really maybe even if you've got a service based business, let's say, how do you productize that to create sort of a package or a retainer that's indicative of the value would be my biggest piece of advice.

Jeffrey Feldberg: It's interesting because what you're talking about there, that's really the entrepreneurial theme. We are the underdogs. We've got something to prove. That said, in the beginning, at least, we may not have the belief in ourselves. And so when you were starting out. 

Proving Yourself Mindset

Jeffrey Feldberg: You're an immigrant, you're a female. And so from someone looking from the outside and oh my goodness, strike one, strike two.

How did you look to put that [00:22:00] aside and despite that come out on top?

Ruchi Pinniger: I think honestly it was this personal work that I do, it was the beliefs, it was hiring coaches, it was letting go of the stories. I think I had to prove it to myself. 'cause my whole life I had to prove it to others. would walk into the conference room in a suit and heels looking professional, and the guy next to me, who was my right hand, everyone would talk to him and he'd say, you've gotta ask the boss.

That. Literally happen to me all the time I already had to prove it to everyone else. At some point you just get over it and you're like, I don't need to prove myself to anyone. My value, my worth. It's inherent in me now, but it doesn't just happen overnight. It happens because of my thoughts and my beliefs and my own, working through these pillars, I do myself all the time.

I still do it.

Jeffrey Feldberg: It comes from the mindset. It's not what you're saying, it's the body language and what you're projecting and how you're feeling at the time, which is actually a great segue to what you're doing. 

Working With Watcher Prosper

Jeffrey Feldberg: Bit of an unfair question. I'll throw it out there anyways though, [00:23:00] imagine now I'm showing up and I know it could be.

Well, Jeffrey. Sure. Your journey is different than everyone else in your business, different than any everyone else, but generally speaking. What does it look like? I'm showing up. Okay, Richie, heard you on the Deep Wealth Podcast. Love what you're doing. I'd like you to work with myself, my company, my team.

What's going on, how long is it taking, what's the process, the system, what can I expect?

Ruchi Pinniger: Yeah. 

Financial Partner Model

Ruchi Pinniger: So in terms of the work that we do as a company, we're working with small businesses. They are pretty small, typically up to about five employees providing services, and we are your sort of your financial partner. I would say somewhere between a mindset coach, a bookkeeper, and a fractional CFO.

That's what makes us different. Just marrying the fact that you've gotta look at the finances and also have those, the mindset beliefs. So we'll come in we'll take over your QuickBooks, clean 'em up. 'cause usually there's a big cleanup job in there. And then we will start meeting with our clients on [00:24:00] a regular basis to go through the numbers, create a space for safe conversations, judgment free conversations, work with you to do projections, to do planning.

Making sure you're ready for tax time with your CPA, making that time easier instead of really stressful for a lot of people. Like January comes and you're like, I know I have this covered. And really all of that is through the lens of money mindset. when we're with a client in a meeting, we're not just talking about the numbers, but we're really listening to.

What it is you're saying, what's deeper under there? And we may get into that with you. You might say everything's great, and then the next minute you might say, there's no clients and it's, everything's really slow. So we're not gonna just glaze over that. We're really gonna dig deeper and get you to a place of, ah, okay, there are possibilities.

Where are all those possibilities Helping you to see them.

Jeffrey Feldberg: Absolutely. 

Founder Bottlenecks

Jeffrey Feldberg: And Ruchi, when people come into Deep Wealth Nation, when they're going through our Deep Wealth Mastery program and a nine step roadmap, one of the biggest, I'll call it, some people call it [00:25:00] an obstacle, a challenge. I call it an opportunity. The business doesn't run without the founder. They have no projections.

They have no idea about cash flow. They're doing everything themselves with the wrong belief. Well, I just do it better than everyone else, or I can't trust anybody else. I've gotta be the one that is all over it. But the end result is they're doing things they really shouldn't be doing. They should either automate, delegate, or eliminate, and they're doing none of those things.

And so as we talk about this, is there any particular client that comes to mind as a successor? Yeah. Jeffrey, when came to us, here's what was going on. Fast forward however many months or years now as a client hears what's actually going on because of what we've been doing.

Bookkeeping Rescue Story

Ruchi Pinniger: Yeah, I mean we have a client who was outsourcing her bookkeeping to her CPA, who did her taxes. She felt she had no control. She just felt like something was off. She listened to her instinct because they really weren't looking at numbers. None of them made sense. what she was seeing.

And I'm glad she did because we took over the [00:26:00] bookkeeping. We found there were like negative bank balances. There were employee credit cards. That weren't linked to her QuickBooks, therefore the expenses weren't being deducted. There were lines of credits that weren't linked, and therefore the interest expense on those weren't in there.

It was a kind of a nightmare, frankly, and we took it over, we cleaned it all up. We got it to be accurate. So now she has really great data to make decisions. And that's the thing, of course, the founder. is, and absolutely should be involved in the finances of the business. It doesn't mean that they're doing the bookkeeping, though, so that's why we're partnering with the founder to be their financial guide, it is pretty lonely being an entrepreneur many times, right?

So imagine having a thought partner when you're thinking about when's the next hire, is this the right time to do this? And also, helping you see things that maybe you're not seeing, just what are the other possibilities? Let's look at the expenses. We're not gonna come in and say, I want you to cut everything.

We're gonna say, what are the things that are just here that [00:27:00] you're not even using? What are the easy things where we can save? And then what are the possibilities from a revenue perspective that, we can talk through? Are there other offerings that you can, put out there or when's the last time you raised your rates?

Just really accountability in many ways.

Jeffrey Feldberg: And as you're going through that, again, another unfair question because the right response would be, well, Jeffrey, come on. Every business is different. There is no one size fits all. 

Cut Costs Fast

Jeffrey Feldberg: Generally speaking though, what would be some low hanging fruit that most businesses have where you can come in and say, Hey, let's cut out these expenses here.

It's not really needed. You get an instant boost in your profits, and if you're looking to grow your profits, keep your company forever, wonderful, you now have a more profitable company. Or if you're looking at one point to sell in the near future, terrific. Your enterprise value just went up. What would be some low hanging fruit that as founders, we tend to overlook, but they start to pile up and one thing leads to another.

Small expenses here and there can make a huge expense at the end of the year and over the years and even decades. So what's going on with that? Any low hanging [00:28:00] fruit that you can suggest.

Ruchi Pinniger: Absolutely The one theme that I often see is the software and subscriptions and the dues and memberships. So the things that you're paying for monthly that maybe aren't big amounts, so you're ignoring them 'cause you're like, oh, it's just 129. Oh it's just 99. But when you actually add them up, they're thousands of dollars that you're not even potentially using.

Like a lot of times people, we find that our clients like maybe signed up for a free trial of something and then they forgot and it. It went on Autorenew and now they've been paying that, and then we bring it to their attention and they're like, oh, I didn't even know I had that. So those things are, I think those are a really great starting point.

Profit Versus Cash

Ruchi Pinniger: And then just in terms of like money habits, right? Which I know you didn't ask, but I just wanna share, I so often hear from founders, I'm profitable, so why do I feel broke? Because people think having profit is the same as your cashflow and it's not. If you're a founder and you're paying yourself through an owner draw, not through payroll, [00:29:00] depending on your, structure the owner draw isn't on your profit and loss statement, but it comes out of your cash.

So that's one big piece. And also saving for taxes, like in many cases as a small business, your taxes are personal taxes. They're not corporate taxes or business taxes. So when you're paying taxes. You're not paying them out of your business or they're not coming into your profit and loss report.

So really making sure that people are not only looking at profit and loss, but looking at the actual cash flow. And are you saving for taxes? Are you saving for growth? Are you paying yourself? All those pieces that don't come into the profit and loss and planning for those is really key.

Hidden Anxiety Costs

Jeffrey Feldberg: So rci, as you're talking about that you have my wheels turning and I'm wondering because there's a whole other narrative, there's a whole other conversation that as founders, it's easy for us to avoid the painful topics, the things we don't wanna look [00:30:00] at, or they bore us, or we have no idea what's going on with that.

And so when we don't truly know our numbers, yes, there is a cost of perhaps lost revenue or lost profits. That's at the surface when you're working with your clients and through the Watch or Prosper methodology through your system. What's the real hidden cost when I don't truly know the numbers in my business?

Ruchi Pinniger: The real hidden cost is, I think, on our mental health, our peace of mind when you don't really know, like how do you grow something when you don't even know what's actually happening? I mean, Just think about that. So there's an underlying anxiety that you're just living with that you almost might, it might be subconscious, you don't even realize it, how differently you feel when you know the numbers versus when you don't know the numbers.

There's that. People sleep better. I mean, Literally we're told like beautiful things all the time. I can now sleep better, I can make better decisions. I have this information now. It's the information, but also having the thought partnership, being in a safe space with [00:31:00] someone to be able to talk about your finances.

Money Shame Origins

Ruchi Pinniger: There's something there, from a woman perspective, 61% of women would rather talk about the details of their own death, like dying than talk about money. So there's a lot of shame we carry with us in many cases as well around our money.

Jeffrey Feldberg: Why do you think that is? Where's that coming from?

Ruchi Pinniger: I think the younger generations are a little different now because we're having a lot more conversations. but I think my generation, a lot of people were told like, you know, it's not polite task about money. You don't need to know this.

We weren't taught about money, but we have, we're now expected to run a business without. Learning it. And so there's shame in that. There's shame in, I don't know how to do this. it's a lot of judgment. We have it's self-judgment in many cases.

Jeffrey Feldberg: And wow, it is, I'm gonna use the word dangerous when we. Suppress it, put it back down there. We don't deal with it from a mental health perspective. There's all kinds of issues, and so you begin to talk about that when your clients begin to open up and, [00:32:00] okay, let's talk about finances. Let's put everything out in the sunlight.

Sunlight's gonna cleanse everything. There's nothing hidden in the dark anymore. People are feeling better, they're sleeping better. What other emotional patterns are you seeing once you get that topic of finances and money and profits or losses, whatever the case may be, when you get all that out there.

What kind of changes do you begin to see within your clients?

Ruchi Pinniger: We start to see more revenue truly, and we start to see better habits. That's the biggest thing. 

Beliefs Drive Behavior

Ruchi Pinniger: For example, we had a client who, when we were meeting, we talked about what do we need to do to get your business revenue to be able to meet your business and your personal needs. That's one of the things we do is really aligning what the revenue goals are to our personal needs.

That's something not a lot of people think about. So with her, we came up with these targets of what do we need to do? To increase the revenue to live the life that you want. And in her case, it was really interesting 'cause she raised her rates, she took the advice, but then it was really interesting.

Then [00:33:00] she was just continuing to spend and we started to pay attention to that and say what's actually happening here? This is where the story comes in. The beliefs come in. Ah, when I was a little girl, my father weaponized money, so I don't feel safe holding onto money. And so this is where the work begins too.

Like now we've gotta look at the business habits, but also that mindset piece and work through that with you. How do you begin to feel safe with money? How do you begin to trust yourself with money? And that's, I mean what you see with many people is they carry those beliefs with us and with them, and you see the effect of that in the business.

Jeffrey Feldberg: What I love about that story, it's a sad story in so many ways. At the same time though, we're putting it out there for Deepal Nation to hear, to listen from and to prosper from, because what I'm thinking about this Ruchi is as the founder, I'm really the focal point for the company. So I imagine your client who looked to money as being weaponized from when she was a little girl, [00:34:00] that's just how it was with her.

I would imagine that in her company, whether it was five employees or 500 employees. That was probably the theme in the company because her team would look at her, oh, okay, well this is how she's, so I'm gonna be like this, and next thing we know, it's magnified 10 x 20 XA hundred x in the company. Because now everyone is following the lead of what they're seeing, what the leader thoughts about that.

Ruchi Pinniger: It's exactly right. 

Team Abundance Contagion

Ruchi Pinniger: I said it earlier it's the idea that your money habits are contagious. thinking about that, let's go there with the team. How are you showing up? if you are not feeling abundant, How are you paying your team? How are they feeling about your generosity and their worth and value?

You as a leader want to come showing the abundance and the possibility and leading them into seeing what is available to you and what is available to the company. 

Reticular Activating System

Ruchi Pinniger: It's a little off topic, but I think it's really important to share this with you all thinking about this part of our brain called [00:35:00] the reticular activating system.

It's the RAS Jeffrey knows all about it, right? The RAS is like the bouncer for your brain. So imagine there are 11 million bits of information available to you at any second. Your brain can process 40. So your brain is looking for evidence of what it is you believe and what it is you're looking for. So if you are thinking about the RIR, like if you are saying there's never enough money, there's not enough clients, then.

If that's what you're saying, your brain is looking for evidence that there's not enough clients and you're missing all the possibilities. All the clients that are out there now, instead, if you are talking to, you, know, your team about sales and about possibilities, and you're saying they're clients are everywhere.

Everywhere we look, we get to see clients that are ideal for our company. They're gonna start to train their brain to look for those possibilities and to look for those opportunities.

Jeffrey Feldberg: And as you're talking about that Rja, I'm thinking actually in Deep Wealth Mastery, our 90 day [00:36:00] program where we go through the nine step roadmap, we talk exactly about that and the story that we use. Deep Wealth Nation, you can relate to this. Perhaps I'll use a very simple example. You were looking at a red sweater.

We're gonna go with your fashion theme ruchi of how you like some fashion. Not that it defines you, but you like it. You get enjoyment. You're looking at this beautiful red sweater, you end up buying it because you love it so much. And now as you're walking around, wow, look at all these red sweaters. I never saw them before.

Look at them. So was it that the red sweater just magically manifested everywhere because now that you have it, everyone else has it? Or was it always there before? You never saw it. And that's what I love about the whole brain and the reticular activation system is what's really top of mind. What we tell our mind, Hey, this is what I want.

Subconsciously our mind is working 24 7 even when we're sleeping. Okay, this is what Ruchi wants. This is what Jeffrey wants. Let me figure out a way of how we're gonna manifest that, how we're going to get that very powerful system in regards to doing that. And so I love that story that you're sharing with that.

One Action Today

Jeffrey Feldberg: Let me ask you this. [00:37:00] If there was one action, a low hanging fruit that someone in Deep Health Nation could do right now today after listening to this episode, before they go on to the next meeting, and it's coming from the watcher prosperous system that could make a meaningful difference in the business, what would come to mind?

What would you be suggesting?

Ruchi Pinniger: I would always send you back to RIR. Start to pay attention to your thoughts immediately. That's where your biggest change is going to be. What are you putting out? What's the energy you're putting out? What are the thoughts? What are the words? Those words, those thoughts, that energy has so much power. You have so much power.

I want everyone to know that they have so much power just within themselves to make change. You don't need anyone else. You can do this on your own in terms of the way you think. So start to really look at when you're going in that next meeting, what do you want to accomplish? What do you visualizing for the meeting, let's say?

And start to put those thoughts out there and those thoughts and those words.

Jeffrey Feldberg: What an opportunity, [00:38:00] what a gift we have. Of we can keep it local with our team members, with our loved ones, with our family, ones family dinner or the next team meeting that we can bring that to them. And I wanna circle back to something that you said, because I know some in Deep Wealth Nation are saying, Hey, well Richie, you said I should be generous with people.

I should have an abundance mindset. Yeah, I did that and Soandso took advantage of me when I did that. And I've been on both sides of the coin Ruchi where I have been not so nice. I've been a real fill in the blank where I was not putting out the abundance or the compliments or on the monetary side. And then I've been on the flip side of that and sure, along the.

People, some of them took advantage of that and learn live, move on. Don't make the same mistake, and it doesn't mean that everyone else has to suffer, sadly. There's always, not always, but there can be a bad apple, as a saying, goes with that. But everyone shouldn't have to suffer with that. But by and large, I find that as the giver.

Oftentimes I also get more or [00:39:00] receive more than the receiver of that. That's just how the universe works with that. It's really an amazing principle. 

Giving Through B1G1

Jeffrey Feldberg: And speaking of giving, what was interesting when I was preparing for today, sure. You're helping your clients, you're making a difference out there. You're not just stopping there because I know you have a partnership that's a whole giving institute and is making a difference.

So why don't you share a little bit about that, of what is that, why you're doing that, some of the impact that you're making with you and your team?

Ruchi Pinniger: Yeah. B1G1. So we are partners with them and anyone can join. If you're interested, reach out to me. the founders, Masami and Paul really believe that we don't have to wait to meet a goal to be able to give back. What if every time we do business together, we get can give back, and so every time we get a client referred to us by someone and it leads to a consult or we take on a new client, we donate to B1G1.

And there's beautiful initiatives that we get to handpick that are aligned with the mission that we have at Watch Her Prosper. [00:40:00] There's. I think thousands of ways you can give back through B1G1. In fact, since you brought it up, Jeffrey, I would love to say that anyone who reaches out to us as a result of this podcast, and we have a consult with you, whether you work with us or not, I would be honored to make a donation to B1G1 if that were to happen.

So just throwing that out there since you brought it up.

Jeffrey Feldberg: Absolutely love that and deep both nation. What are you doing with your business in terms of your impact with that? It doesn't have to be B1G1. Maybe it is B1G1. You'll learn about that. Love that. Wanna do that? Perhaps it's something else. If you're not doing something, hey, this is opportunity knocking.

Because again, when we have a bigger cause, when we're helping people making a difference, it's amazing. I'm gonna go back. You can call it God or Spirit, or the universe or the quantum field. The more that we make an impact, the more that we give, the more we tend to receive as well. Of course, we gotta be smart about that and do the right things with that, but what a difference that [00:41:00] it can make.

And let me ask you this, Ruchi, before we start going into wrap up mode, is there a question, an important one that we haven't yet covered that you'd like to share with you both nation?

Prosperous Life Calculator

Ruchi Pinniger: I think just really understanding how your. Personal, most prosperous life aligns to your business. So we even have a calculator we can share with you. Have you really stepped back in your true abundance without any societal limitations and said, what is my most beautiful, prosperous life look like?

And how much would I need to make to have that life? What if you just allowed yourself to not limit that and really think about it, and then. allowed yourself to think about the possibilities of how do you get to create that for yourself. So we have a calculator your prosperous life.com.

That you can go to and you can really just play in there and start to think about that. That's an important thing to know, to align your business goals with that personal, prosperous life of [00:42:00] yours.

Jeffrey Feldberg: And what I've been reminded of rci as you're talking about, that when you go back for most children, myself included, back in the day. We didn't know any better, and that was for the better. And we would dream and have, okay, I'm gonna be doing this or that, I'll use the F word. We're having some fun with that.

Somewhere along the lines, sadly. And unfortunately we lose that. And so deep, both nation. And when's the last time you began to dream big about your business? You started your business for a reason. And I suspect somewhere along the line that fun, that passion got lost. The business grew. You got drawn into it, and now it's the same old different day and you're dealing with the fires and everything else.

Why not go back to the beginning? Why you started that and get to the root cause of, Hey, I just love doing this. I'm gonna look at my business through a different lens. Actually, in step one, big picture, we talk all about that of, Hey, how do I channel my business to now find a whole new different problem, an up and coming problem where I'll be world class, make a difference, creative market disruption, and all the wonderful things that can go [00:43:00] along with that.

That said, we are gonna go into wrap up mode and Ruchi. 

Back To The Future Wisdom

Jeffrey Feldberg: It's a tradition here on the Deep The Deep Wealth Podcast where it's my privilege and honor that I ask each guest the same question and it's a fun one. Lemme set this up for you. 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 here's the fun part. It's tomorrow morning, you look outside your window. Not only is the DeLorean car curbside, the door is open and it's waiting for you to hop on in which you do. You're now gonna go back to when you're eight. Child, a teenager, whatever point in time it would be. What would you tell your younger self in terms of life wisdom or life lessons or, Hey rci, do this, but don't do that.

What would it sound like?

Ruchi Pinniger: Beautiful. Okay. There's very few things that would want to make me go back to being a teenager, but my answer is I would go back to when I was 15 before I lost my mother, so I could just tell her how much I absolutely love her and how grateful I am for her. Because family and love and gratitude [00:44:00] is where it's at.

Y'all going back to that pillar?

Jeffrey Feldberg: Wow. So what a traumatic story that must have been at 15, such a tender age of having your mother taken from you. What was that like back in the day of? How were you able to get through that? Because. Some people would play the victim card. You didn't. You're playing the victorious card, the Victor card. So what was going on that you can share with us about that?

And thank you for being so open and vulnerable to share that.


Phoenix Through Loss

Ruchi Pinniger: yeah, at that point I had no parents, I shared earlier I grew up with a single mom. We lost our dad very early, my brother and I. So now here I am at 15. And I moved in with my uncle, my mom's brother and his family, my aunt, my two cousins, and I became a family of five.

So it was very different. And yeah, I think just going back to trust and gratitude, like at the time, obviously, well, I almost don't think I really processed it until I was older, but now I look back and I realize it was all how it was meant to be. Like my whole life was set up.

I trust that [00:45:00] my whole life was set up the way it was for a reason. Because in truth, I probably wouldn't be here talking to you today if that hadn't happened. I would never have moved to New York. I never would've, created my life here with my husband and my son in New York City. I never would've gone onto Wall Street and I wouldn't be doing this work truthfully.

So I look back and I truly just trust that it all happened, how it was supposed to.

Jeffrey Feldberg: And it's number one again, thank you so much being so open with. Does in Deep Nation as you're hearing that, what a heartfelt story and as an example of you just went within and we can't control what happens around us, but we can control how we respond to that and with what you're sharing with us, it's such a terrific example of, okay.

Wow. Incredibly difficult, perhaps challenging situation. Let me see though, how I can pick myself up and fly from the ashes, like the Phoenix and move on and show my mom and the [00:46:00] others. Hey. Was not lost with that. And as I'm saying that Ruchi is showing on camera, you can't see it a picture of the Phoenix on a little sticky note there.

Wow. So talk about that, that is just incredible Ruchi and I really appreciate that and sharing that with us Deep both Nation. Talk about inspiration today. 

How To Connect

Jeffrey Feldberg: And speaking of inspiration, someone in Deep Nation, they would like to reach out to you, speak to you, the team, perhaps even become a client and be the benefactor of all that.

Where would be the best place online to reach you?

Ruchi Pinniger: Our website is Watch Her Prosper dot. Com and you can go on there, contact us. There's an application on there that you can fill out to work with us and we can learn more about you and reach out. You can follow me on Instagram, send me a DM as well and come hang out with me there.

Jeffrey Feldberg: There you have a deep patient. Doesn't get any better. And what I love about the Pulp Nation, it is so easy. Go to the show notes. It's all there. It's a point and click. Well Retreat's official. Congratulations, this is a wrap. And as we love to say here at [00:47:00] Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe.

Thank you so much.

Ruchi Pinniger: Thank you.

Subscribe And Support

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.

Are you ready for it? 

The dramatic pause. I'll just wait a moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, [00:48:00] whatever you want that to look like.

And every time you subscribe and a fellow entrepreneur subscribe, it's a testament to how together, Yes, we are. We are changing the social fabric of society. One business owner at a time, one liquidity event at a time. So don't let the momentum stop here. Subscribe now on your favorite podcast channel.

You'll never miss an episode. You'll be the first to hear from the top industry leaders, the innovators, the disruptors that are really changing and shaping the business world, and maybe you're commuting, maybe you're at the gym, maybe you're taking a well deserved break that we spoke all about on this episode.

The Deep Wealth Podcast, it's your reliable source for the next big idea that could literally revolutionize your business. So once again, please hit that subscribe button, stay connected, inspired, and ahead of the curve. And again, your next big breakthrough moment, it might just be one episode away. Maybe it was even this episode.

So all that said. Thank you so much for listening. 

Final Thanks And Farewell

Jeffrey Feldberg: And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's [00:49:00] continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. 

Thank you so much. 

God bless.


Ruchi Pinniger Profile Photo

Former Hedgefund CFO on Wallstreet, International Speaker, Venture Capital Investor and Founder and CEO

What if financial clarity wasn’t about spreadsheets… but about self-worth?

Ruchi Pinniger is the Founder and CEO of Watch Her Prosper, a modern financial services firm on a mission to help women entrepreneurs build profitable, scalable businesses without burning out or second-guessing every decision.

But Ruchi didn’t start here.

Her journey began inside the world of traditional accounting, where numbers ruled the conversation and founders were often left overwhelmed, under-informed, and quietly ashamed of what they didn’t know. She saw brilliant women building impactful companies while privately struggling with cash flow, pricing, payroll, and fear.

Instead of accepting that as “normal,” she built something radically different.

Watch Her Prosper blends financial strategy, bookkeeping, CFO support, and education into a people-first experience designed to empower women to understand their money, not hide from it. Ruchi’s work sits at the intersection of profitability and power. She helps founders move from reactive to intentional. From guessing to knowing.

Her mission is bigger than balance sheets. It’s about shifting how women relate to money, leadership, and their own ambition.

And that’s where this conversation gets interesting.