John Knowlton - From Success To Significance
John Knowlton is an entrepreneur, investor, and former pastor who has built his life and career around one core belief: better thinking leads to better outcomes. His bi-vocational journey spans building a wealth management firm that grew to over $1 billion in client assets—allowing him to retire at 51—while also serving as a pastor, teacher, and jail chaplain, where he saw firsthand how mindset shapes direction and destiny. Today, John works with CEOs and business owners to help them think more clearly and lead with purpose, drawing from his experience facilitating executive retreats and advising leaders. He’s also redefining legacy by involving his adult children in shared governance of family wealth through a mission-driven family board, while actively investing in value-add real estate projects in Bend, Oregon. John is the author of Thinking for Success, a newly released book that offers practical stories and insights to improve productivity, relationships, and long-term impact.
In this episode, you will be able to:
- Discover how John built, scaled, and sold a billion-dollar financial services firm, then redefined success after stepping away at age 51.
- Learn why hitting “100%” on a traditional financial plan isn’t the finish line—and how to think beyond retirement toward multi-generational impact.
- Understand why families that last for generations prioritize illiquid assets like real estate and businesses over easily spent wealth.
- Explore John’s concept of shared governance and how involving children early prepares them to steward wealth responsibly.
- Gain practical strategies for teaching kids about money, values, and decision-making through everyday conversations and real responsibility.
- Get inspired to align wealth, purpose, and faith to build a family legacy that serves as a force for good long after you’re gone.
The key moments in this episode are:
5:15 Why Real Estate Supports Long-Term Freedom
9:59 Illiquid Assets And Lasting Families
12:00 From Cold Calls To Billion-Dollar Exit
18:20 Shared Governance Beats Traditional Estate Plans
24:33 Inviting Adult Kids Into The Board
33:45 Training Younger Kids Through Daily Habits
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Full transcript here:
John Knowlton
My why, I've already said it, but I'll say it again, is to build a family that maintains its identity as a force for good for generations. In other words, the Knowltons are a people who add value to their community. And I want that to be true, not just while I'm alive, but for generations.
Mike Swenson
Welcome to the Real Freedom Show. We inspire you to pursue your passion to gain time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson. Let's get some real freedom together. Hello, everybody. Welcome to Real Freedom, Real Estate Leverage Freedom, where we talk about different ways that people can build time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson. If you want to get started on your real estate investing journey, check out our website, freedom throughrealestate.com. We have lots of great information on there, articles with the goal to inspire you guys to pursue and take action on something inside of real estate. Today's guest on our show, I'm really excited to share. We have John Nolton here, gonna get us to think a little bit bigger and a little bit more long term about your future. So John actually built a billion-dollar business, sold it, walked away at the age of 51, took a year off in COVID, traveling around in an RV, and really, you know, gained some additional perspective. And uh, so you were the author of the book Thinking for Success: 52 Stories that upgrade your thinking to boost productivity, problem solving, and relationships. And really, you're about focusing on thinking about your future and building wealth and getting your family involved, putting together mission, vision, value statements, and inspiring people to think bigger than that. And then having enough money is not necessarily the finish line, but there's so much more that you can do with it. So, John, I'm excited to have you on to be able to get us to think differently and to think bigger about our purpose and what we're doing here. So, thank you so much for being on the show.
John Knowlton
Oh, Mike, it's a real pleasure. And it's, you know, it's really my hope that this conversation will be a blessing to the listeners and viewers and that people can get a vision for something bigger than just hitting 100% complete on their financial plan. You know, for 20 some years, I worked as a financial planner and and the software that most of the industry uses, you know, uh analyzes is you is your goal complete? In other words, do you have enough money to hit your retirement goal? And that's 100%. And it never goes to 110 or 120. Like 100 is the top. Like you've you've got enough. And my challenge with that was I was always frustrated with this, frustrated with the software. And what I've realized is, you know what? My goal is to build a family that lasts as an as an entity, as a force for good for multiple generations, and hitting 100% for me and my wife's spending needs. That's not that's not my goal. My goal is a whole lot bigger than that.
Mike Swenson
So I think about that as well. I know just from talking with people that help with finances and and management. You can correct me if I'm wrong, but from what I've kind of heard, you know, the the general thought is um, you know, you you build that nest egg and then you focus on, okay, I take four percent every year until it gets smaller and smaller and smaller. And then yeah, what happens if you live longer, right? People are living longer, there's improvements to health, and so you don't want to outlive your money. And so, yeah, to your point, if somebody is like, hey, I got the 100% and then you live longer, you're kind of stuck. And for me, what I love about investing in things like real estate is you know, over time, real estate can continue to appreciate it, can continue to go up in value. And if you have your assets in something that's producing that consistent cash flow, um, your income's not gonna necessarily go down or it's less likely to go down. And then you don't have to be as worried about am I gonna outlive all that savings that I built? But yeah, to your point, there's so much more out there. And for me, it's about changing my family tree, being able to do something for my kids, however involved or not involved they want to be, but it's building something that can last beyond when my wife and I pass away. So excited to hear what you have to share on that.
John Knowlton
You know, Mike, that's really interesting. I've been studying families that that last for multiple generations. And one of the things that is true about most of these families is they own illiquid assets. In other words, they own factories and businesses and companies and uh real estate that isn't easy to liquidate, or you can't just call the the stockbroker and say, send me a hundred grand, and then it's just frittered away and dissipated. But there's there's a there's an asset or a portfolio of assets that are illiquid and have enduring value. Now, I still own plenty of stocks, don't worry, it's a you know, it's a good driver, but the real estate and the longer term type assets are in alignment if you have a goal of building a family that lasts longer than just you and your spouse. Just a couple of examples. There's a there's a family called the Grosvenor family, and their their G1, if you will, their first generation that they trace back to came to England in 1066 with William the Conqueror. That's 970 years ago or something, 60 years ago. And they were he was granted a little bit of land on the north side of the Thames River, which is now uh a big portion of that land is occupied by the city of London, which is their Wall Street, it's the financial district. So it's like owning Manhattan as your little family estate, you know. So just a really interesting that's a long family.
Mike Swenson
I'm curious to hear just to kind of start here and set the set the stage. So talk about building up your business and kind of the the sale piece, and then thinking about what you're working on today, the whys behind it and the hows, just to get people thinking a little bit differently about how they're approaching building wealth and their their goals and business.
John Knowlton
Sure. So I started out as a financial planner or financial advisor in the 90s. And I mean, it was before we had computers on the desk. I mean, it was uh it was a phone book, and a phone was like the office equipment, you know, it was smile and dial, wake interrupt people at dinner and try to get them to talk about financial planning or reducing their taxes or whatever, and turned that into a practice, not just a sales call, but a practice, got some staff, uh, transitioned the business model from transactional to advice-based, where you collect fees for advice rather than commissions for transactions. And um did a did my first deal where I bought out a retiring advisor in 2004 and realized, oh, you can you can get clients one at a time or you can buy them in chunks. And I liked the buying them in chunks piece. And so spent a decade or so figuring out how to do that, how to market to financial advisors, how to talk to them, how to get them earn their trust and and uh get them to consider selling their business to us. And and so in 2015, we were managing about 125 million dollars, small little team in an office, and we set a goal of being at a billion and so kept pursuing our MA mergers and acquisitions strategy, and we had a key merger in 2018 with another firm. So we had the mergers and acquisition expertise. The the other firm, the partner firm, had a really great client service experience and and model and tools to drive that, as well as really good investment management capabilities. And so we merged as a cashless merger so that the MA expertise now had a great platform to pop deals into. And over the next few years, uh, we 10x'd that thing. So we went from 125 million in 2015 to a billion and a quarter in 2020. That was in five years. Yeah. We 10x'd in five years. And um that's a lot of growth and it takes a lot of work. And so in 2020, we had hit my business goal of being at a billion. And uh one of my adopted kids uh was had been living in a residential treatment facility and was ready to come home. And my wife said, Hey, I'm gonna need some help reintegrating this child into the family. And so I, you know, our operating agreement contemplated the entry and exit of partners. And so I was the first one to to exercise the option to sell. And the the rest of the team bought me out and um took a year off, as you said in the introduction. And um, so any case, didn't really need to work for money. You know, my my 100% was hit, if you will, on my financial needs analysis, but uh I I can't just sit around. And so I've been cranking ever since.
Mike Swenson
You had mentioned about getting your family involved and participating because I know a lot of people, you know, they might run a business or own a business, and the goal is, hey, I'm gonna have my kids run that when I die. And uh, for a lot of people, like it's not it's not something they're interested in. And so, you know, like I had a college roommate where as soon as he graduated college, he took over the family business and he runs it. And I know for me, I've always said, you know, the idea of I'd kind of said it, my kids, it's like they can participate if they want, they don't have to, but it's gonna be something that's a choice for them if if they want to in the future. And if not, no worries, we're gonna encourage them to do what they want to do. But for you, it's so much more than that, like having your family involved and participating in their future and and putting together a mission, vision, values, and and being an entity that can accomplish so much more. I'd love to kind of dive into that side of it and talk about the the why behind that for you and kind of what drove that conversation. And then we can kind of talk about the fruit from that.
John Knowlton
Yeah, sure. That's that's a wonderful place to start. So I just want to make a quick comment. I I like to distinguish uh wages for work versus profits for ownership. And so it's possible to be an owner of a business but not work in it. It's possible to work in a business and not own it, or you could do both. And I think it's important to align compensation, your wages for work, and you can have a compensation philosophy about that. Are we a you know an entry-level employer? Are we a middle of the pack or are we above the average? You can you can set your your parameters around that. But if somebody's working in the business, even if they're your kid, uh I think they should be paid. And then if they're an owner, then there's also an element of you know, there's some rewards for owning things. So I just think that's an important distinction. I was talking to a guy in Europe uh recently who said that in the the the tradition in Europe is you work for the family business for minimum wage as a as your contribution to the family business, which what do you what do you know? People are really resentful about this. Um, you know, it shouldn't be a surprise. It wasn't to me. So, any case, but to your question about why so Simon Sinek in his book Start with Why told us to start with why. In other words, figure out why are we doing what we're doing. And so, my why, I've already said it, but I'll say it again, is to build a family that maintains its identity as a force for good for generations. In other words, the Knowltons are a people who add value to their community, and I want that to be true, not just while I'm alive, but uh for generations. So that's the why. The what, so I'll come back to the how, which is in the middle. Why is force for good for generations, the what is stewardship of our family resources, our our family wealth. And then the how is the unique piece that I'm bringin
