[EO South Florida] Designing a Life That’s Rich Beyond Money With Noah Rosenfarb

Noah Rosenfarb is the Founder of Wealthrive, a boutique advisory firm that helps high-net-worth entrepreneurs optimize tax strategies, build predictable income streams, and design lives that are rich beyond money. A third-generation CPA, Noah has sold eight companies, taken one public, and completed over 50 real estate investments valued at nearly $1 billion. He is also the author of EXIT: Healthy, Wealthy and Wise and co-hosts the Divestopedia podcast, where he shares insights on business exits and wealth transitions. Through Wealthrive, Noah leads a multidisciplinary team dedicated to empowering founders to achieve financial freedom and a lasting legacy.

Here’s a glimpse of what you’ll learn:

[3:59] Noah Rosenfarb introduces the “Lotto Ticket Method” and how it inspired the founding of Wealthrive
[7:23] Using the lotto exercise to navigate big life decisions like where to live and how to spend time
[16:35] Why entrepreneurs must own their tax strategy and not rely solely on preparers
[19:55] 23 overlooked tax strategies to unlock low-hanging savings
[25:15] Structuring a business exit to generate tax-free income and avoid estate tax using a Wealth Preservation Trust
[30:04] Preventing post-sale regret by preparing purposefully before exiting a business
[34:02] Understanding the consequences of IRS disputes and how tax opinion letters help mitigate risk
[36:17] How Noah’s real estate investing journey began with a house hack and evolved into $900 million in assets

In this episode…

What would your life look like if money were no object? It’s a question many entrepreneurs don’t pause to ask as they chase success. But what if designing your ideal life started with a simple thought experiment and a lotto ticket?

According to Noah Rosenfarb, a seasoned exit strategist and third-generation CPA, you don’t need to hit the lottery to start living intentionally; you just need clarity, courage, and a plan. He highlights a personal exercise he calls the “Lotto Ticket Method,” which helped him and his wife make bold, values-driven decisions about their lifestyle and work. By asking who they’d spend more or less time with and what they’d start or stop doing if they suddenly had financial freedom, they gained clarity on what truly mattered. This mindset ultimately shaped Noah’s approach to wealth creation, from creative tax strategies to real estate investing to structuring exits that go beyond the money.

In this episode of the Rising Entrepreneurs Podcast, Dr. Jeremy Weisz sits down with Noah Rosenfarb, Founder of Wealthrive, to talk about designing a life that’s rich beyond money. Noah breaks down his unique tax strategies, shares his lotto-inspired lifestyle planning method, and explains how to exit a business without regret. He also talks about building tax-free income and preparing emotionally for life after selling your company.

Resources mentioned in this episode:

Quotable Moments

“I realized I didn’t need to win the lottery; I needed to be more thoughtful, more courageous.”
“My goal was always to find ways to support those entrepreneurs because I thought they’re the heroes.”
“You should be generating a higher return on your time outside your business, not a lower one.”
“The way the Earth moves is through the ingenuity and creativity of us as entrepreneurs.”
“Sometimes you have to distinguish what’s fun from what’s profitable, and they’re not always the same.”

Action Steps

Use the Lotto Ticket Method annually: Reflecting on your ideal life helps clarify values and guide bold life decisions.
Build your tax strategy proactively: Taking control before major financial events can prevent regret and save significant money.
Evaluate return on time, not just investment: Measuring time ROI ensures you’re prioritizing work that maximizes your unique value.
Explore overlooked tax strategies with your CPA: Revisiting these tactics can unlock substantial savings your accountant may have missed.
Design your post-exit life before selling: Preparing emotionally and financially ensures your next chapter is fulfilling, not disorienting.

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Episode Transcript:

Intro: 00:03

Welcome to the Rising Entrepreneurs Podcast, where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

Dr. Jeremy Weisz: 00:13

Dr. Jeremy Weisz here, Founder of inspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Noah Rosenfarb. You can check him out at wealthrive.com and no, before I formally introduce you, I always like to point out other episodes of the podcast people should check out.

I had, since this is, you know, part of kind of like the EO series I had Rick Rappe on. I was in Seattle. We talked about direct mail. I love direct response marketing and direct mail. We geeked out on direct mail.

Why it still works. How to do it right. Another one, Eric Evans of EO Austin. He talked about transforming lead generation and customer engagement through AI. That was really interesting.

And Roger Einstoss of EO Argentina, and he helps people hire software engineers all over the world. So we talked about that and what he does with that. So and with the advent of AI and other things, he’s become popular among companies. So check those episodes out. You can check them out on Insider.com.

And we have a special podcast, Rising Entrepreneurs, that is really featured featuring different EO members. This episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships. We do that in two ways.

One, we’re an easy button for a company to launch and run a podcast. We do the strategy, accountability, and the full execution and production. Number two, we’re also an easy button for a company’s gifting. So we make gifting and staying top of mind for your clients, partners, and prospects easy, simple, and also affordable. So some people even send to their staff from a culture perspective.

So all you do is give us a list of people we do. Everything else we call ourselves kind of know the magic elves that run in the background to make it stress free for companies so they can build better relationships and most importantly, run their business. Right? So for me, the number one thing in my life is relationships. I’m always looking at ways on how I can give to my best relationships, and personally, I found no better way over the past decade to profile the people I admire and share with the world what they’re working on on the podcast, and also sending them sweet treats in the mail.

So go to rise25.com if you have questions or support@rise25.com and email us. I’m excited to introduce today’s guest, Noah Rosenfarb. He’s the Founder of Wealthrive, where he helps entrepreneurs generate predictable income, reduce taxes, build their legacy, and create their ideal life. He’s done many talks on this. I’ve, you know, watched many videos, Noah on this and really walking through that ideal life is it kind of starts with that.

We’ll dig into kind of the lotto ticket method, I don’t know, that should be a book that you the next the sixth book you come out with is the lotto ticket method because I love your philosophy, you and your wife’s philosophy around that. But he’s a seasoned investor and exit strategist. He sold eight companies for a combined total exceeding $750 million, taken one public, complete over 50 real estate investments valued at nearly $1 billion. As I mentioned, he authored five books and the latest one, if you haven’t checked it out, Exit Rich Beyond Money. So, Noah, thanks for joining me.

Noah Rosenfarb: 03:22

With pleasure. Glad to be here.

Dr. Jeremy Weisz: 03:24

And we’ll start. And I want a big a big thank you to to two people. John Corcoran, my business partner, who’s like, you have to have known on the podcast also Kevin Thompson, who’s also I think I was hit at all angles. So like you have to have Noah, Adi Klevit, also mentioned Noah as well. So there’s like three people in my universe that I trust and like Noah’s, Noah’s the man.

So Noah, let’s start off with the topic of your next book, which is the Lotto method. Now that we came up with on the and just talk about that concept in in what you do. Around that?

Noah Rosenfarb: 03:59

Sure. And I’ll tell a little bit of an origin story around it, because this actually is what led to the founding of wealth, right? So in 2017, I participated at EO nerve in a short talk speaking competition, which I won, and my presentation was on how I won the lottery and what my short talk essentially revolved around the stories that my wife and I have utilized this tool and strategy where we go and buy a lottery ticket and we answer four different questions. If, assuming we won, who would we spend more time with? Who would we spend less time with, and what are the things we’d start doing and what are the things we’d stop doing?

And throughout my life, when I bought these tickets and thought about winning, I’ve noticed that there were different things that I’d like to accomplish. And yet, when I reflected on what was really holding me back. I realized I didn’t need to win the lottery. I needed to be more thoughtful. I needed to be more courageous, and I needed to be truer to myself and to what I really wanted out of my own life.

And it’s led me to make uncomfortable decisions, impactful decisions, and really put me in a position where I feel really proud of the life that I’ve created.

Dr. Jeremy Weisz: 05:16

Talk about maybe some of those uncomfortable, you know, decisions you mentioned that was kind of the impetus of of Wealthrive.

Noah Rosenfarb: 05:24

Yeah. And so I to tie one to the other, maybe they’re somewhat non-sequiturs. I’ll tell you first about how it led to wealth drive, which is I started speaking after I had sold an opera, my last operating business. So I had a family office for divorced women. That was an evolution of being growing up in the forensic accounting business with my dad and helping him scale and sell his CPA firm.

But I testified in divorce court that that led me to founding this family office for divorced women, which I sold in 2014. And essentially was, you know, I don’t know a better word than retired, but I was a full time investor in businesses, in real estate, and I didn’t have a job to show up to. And so one of the things that I thought would bring me meaning and purpose in my life would be sharing my experience. And so I did that talk. I won that speaking competition that led to more talks.

Eventually I started talking about taxes because lo and behold, nobody in EO was talking about taxes in a way that was intriguing and creating value. And after I started giving those talks, people were asking me for help and I didn’t want a job. And so I wasn’t sure how to help them. But eventually I heeded their call and I built a team of accountants, lawyers and financial planners that can implement the Rich Beyond Money framework that I’ve created On behalf of these entrepreneurs. And so it was really one thing leading to another that kind of evolved into what is now Wealthrive.

Dr. Jeremy Weisz: 06:58

Yeah. And I get that. It’s like, listen, I have passive investments. Do I really want to create another company and, and build a team around it and stress and everything that comes with that. So I’ve definitely avoided things like that in the past.

And it just takes enough people to just demand and ask. How often do you and your wife tend to do this exercise? And by the lotto ticket.

Noah Rosenfarb: 07:23

You know, more recently it’s it hasn’t come up that much because I feel like we’re so in the zone where we want to be. And part of that, I think the constraints that we have now, and really the constraints that we felt for the last number of years have been around our school age children. So the things that we would want to do, they’re not money related. They’re really more the freedom and flexibility. And so thankfully, my son is graduating from high school.

He’s off to Florida State University and my daughter will be a freshman in high school, has agreed to travel around the world with my wife and me and be homeschooled and that, you know, is more aligned, I would say, with one of those things that my wife and I would really like to enjoy. Our son was adamant that that would not be fun for him. And as you know, I would say, kind, loving and generous parents. We’ve often put our kids needs and desires ahead of our own. And and so thankfully, with our daughter’s adventurous spirit, we’ll be able to move one step closer towards life.

My wife and I eventually want to live as empty nesters. We have a plan to be intentionally homeless, and our goal is to live around the world and, you know, kind of blend, blend work and pleasure and in different time and space.

Dr. Jeremy Weisz: 08:32

I want to talk, and I want to go back to the homeschooling thing and traveling around the world, because that’s really interesting. I think if I, if I pitch that to my two daughters, they would reject it. But that’s, you know, it just depends on the personality. But I do want to hear how you’re going to plan that out, because it’s interesting. It’s just a different mindset around education, which I love.

But talk about some of the decisions you made differently, because a lot of I know one of them was moving to somewhere warm like Florida. Talk about like throughout the years, what are some of the decisions you made with this lotto ticket exercise?

Noah Rosenfarb: 09:08

So I would say it’s really helped in a variety of phases in our life. So that first one that you referenced, we had a nine month old son. We were walking on the boardwalk in Hollywood, Florida, where my grandfather lived, and my in-laws had a place on the beach, and my wife and I were spending three weeks over the holidays with our newborn. And, you know, I had already left my job and I was independent, working on my family office, but working remotely back then. And we bought a lottery ticket.

And one of the things we were saying is like, well, we probably I think we live here, you know, we want to escape the winter and live in the sunshine. And we could spend our summers anywhere, you know. And what’s the trade off? And and lo and behold, again, that really wasn’t a it was a money decision in many ways, because I gave up a lot of earning potential that I had in the market that I grew up in, where my relationships were deep, where my father was known in the community and left that all for South Florida, where we knew nobody. And so there was a financial element.

But the reality was that the life that my wife and I wanted to enjoy would not be impacted by that move. And so, again, it was more of the courage to make the uncomfortable decision to leave my family, leave my wife’s family back in the home state where we were born and raised, and went to college and had our jobs and had our friends and had our social network. But certainly not a decision that I regret in any shape or form.

Dr. Jeremy Weisz: 10:36

Listen, I’m with you. When Covid hit, we worked remotely from Arizona, from Chicago, and I was like, wait, why do we live in Chicago? This makes no sense. So I it’s definitely in the in the plan to get out of the the winter and not suffer every, every winter. So yeah, I mean there’s been a lot of decisions.

I love that maybe we have a subtitle of your book, The Lotto Method How I Won the Lottery and How You can too, or something like that, because anyone could do this exercise. And I remember, you know, I was at a someone who’s, you know, a really, I guess, well-to-do family. I was having breakfast there and I was asking, oh, what do you normally have for breakfast? And they were saying, I don’t know why. It seemed extravagant to me, but like, would have a like two avocados for breakfast.

At the time I was like, that seems like a lot. I’m like, oh, well, if I was wealthy like them some day I’m like, wait, I don’t need to. I could have an avocado or two a day if I wanted to. So but it’s that same mentality. So Thanks for sharing that.

The the homeschool piece. Yeah. Talk about the the thought process behind, you know, travel around the world. How are you going to manage it with the the education side from from kids, you know. You know, a lot of people who have young kids and, you know, they that seems like an interesting concept, but it seems far fetched, like, how would I even do this?

How would I handle it? So I’d love to see how you’re approaching it.

[Continue to Page 2]

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Search Interviews:

[EO South Florida] Designing a Life That’s Rich Beyond Money With Noah Rosenfarb

Here’s a glimpse of what you’ll learn:

In this episode…

Resources mentioned in this episode:

Quotable Moments

Action Steps

Sponsor for this episode…

#1 Our Predictable Podcast ROI Program

#2 Our Comprehensive Corporate Gifting Program

Episode Transcript:

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