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Season 6 - Episode 9

Jeremiah Konger

From Circuit City to Inc. 5000: Jeremiah Konger on Building a Truly Independent Annuity Advisory Firm

Why the descent from the retirement summit is more dangerous than the climb — and how one founder built a business around solving it.

Jeremiah Konger went from mowing lawns in Tampa to building and selling 24 wireless retail stores — then founded Annuity Association after discovering how few products most annuity advisors actually offer their clients. In this conversation, he breaks down why the hardest financial problem isn't accumulating wealth, but converting it into income that lasts, and how guaranteed income changes both the math and the psychology of retirement.

Jeremiah Konger on Henry Harrison Podcast

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About This Episode

Most financial advice focuses on accumulating wealth. Jeremiah Konger built his company around the harder problem: what happens when the paycheck stops.

Konger is the founder of Annuity Association, an independent annuity advisory firm with relationships across more than 80 carriers and access to hundreds of products — a deliberate contrast to the industry norm of representing just two or three companies. His argument is simple: an advisor limited to a narrow product shelf can't genuinely act in a client's best interest.

In this episode of the Henry Harrison Podcast, Konger traces the path that got him there. It starts with a single mother teaching him the value of a dollar, runs through a $34,000 plasma TV sale at Circuit City that sparked his entrepreneurial ambition, and moves through building — and twice selling — a network of 24 wireless retail stores before a frustrating encounter with the annuity industry's status quo pushed him to start his own firm.

Along the way, Henry and Jeremiah dig into what annuities actually are, why longevity acts as a risk multiplier in retirement, and how a foundation of guaranteed income changes investor behavior — allowing retirees to stay invested through downturns instead of selling at the worst possible time.

Konger also shares the milestones that followed: an Inc. 5000 ranking at #294, over $100 million in annuity production in five years, and the launch of a direct-to-consumer annuity buying platform for DIY investors.

For founders, investors, and anyone within a decade of retirement, this is a clear-eyed look at income planning — and at building a business by refusing to accept how an industry has always worked.

Key Insights

  • Independence is a structural advantage, not a slogan. Most annuity advisors represent two or three carriers and only position those products. Annuity Association built relationships with 80+ providers and uses aggregation software to compare the full marketplace — turning fiduciary duty into an operating model.

  • Decumulation is a harder equation than accumulation. American financial culture teaches saving and investing, but nobody teaches how to draw money down. More than 80% of Everest deaths happen on the descent; retirement risk works the same way.

  • Longevity is a risk multiplier. With a 50%+ chance that one spouse in a married couple reaches 95, a longer life amplifies every other retirement risk — volatility, taxation, healthcare inflation, and geopolitical shocks.

  • Retirement runs on income, not net worth. A retiree's sense of security comes from consistent income, not account balances. Covering essential expenses with guaranteed income — pension, Social Security, or annuities — builds the foundation everything else sits on.

  • Guaranteed income enables better market behavior. When essentials are covered, retirees can leave market assets untouched through downturns. Missing just the 10 best market days per year cuts returns roughly in half — the annuity buys the discipline to stay invested.

  • Fund the foundation with as little as possible, but as much as necessary. Konger explicitly advises against putting all assets into annuities; the tool covers essentials so the rest of the portfolio can pursue growth.

  • Product conviction precedes sales success. Konger refused to "just read the brochure" to a client. Discovering his firm offered only 15 of roughly 500 available products was the light-bulb moment that led him to buy annuityassociation.com for $14 that same night.

  • Remove the salesperson to reach the DIY buyer. His new platform, NestEasy Annuities, lets self-directed investors compare rates, carriers, and financial-strength ratings and purchase directly — moving the industry from being sold to buying with confidence.

Episode Transcript

Cleaned & Rewritten Transcript

This transcript has been lightly edited for readability, with filler words removed and sentence structure polished. The original meaning and conversational tone have been preserved.

Henry Harrison: Welcome to the Henry Harrison Podcast — entrepreneurs, business, and finance. Today we're lucky to have Jeremiah Konger with us on the podcast, on Zoom, the works. His company is Annuity Association. Welcome to the show, Jeremiah.

Jeremiah Konger: Hey there, Henry. Happy to be here. Thanks for the opportunity.

Henry Harrison: Let's talk a little bit about what you're doing now. Maybe a good way to start is your company name — it's a pretty catchy, unusual name, and I know it has some significance that separates you from some of the other folks who do what you do.

Jeremiah Konger: Yeah. With Annuity Association, the name is really there to build awareness around the fact that we are a truly independent annuity advisory firm. What I mean by that key word — independent — is that we don't just represent one or two companies or a limited set of products. We have access to the entire independent annuity marketplace.

Why that matters is that the industry as a whole is pretty fragmented. The traditional model for building a business in this space means striking up relationships with maybe two or three different carriers or annuity providers. Those become the only products you're an expert in, and those are the ones you position to your prospective clients.

That was one of the first opportunities I saw in this industry very early in my career. In my opinion, it was an antiquated way of doing this business — and wholeheartedly, the wrong way. I felt that way because in order to truly act as a fiduciary in the best interest of our prospective clients, I believed we needed access to every product. Otherwise, you're biased toward the limited product shelf you happen to have access to.

So from the get-go, we set out to strike up relationships with every major annuity provider in the US — I think that's now over 80 different companies and hundreds and hundreds of products. And we use a unique software that aggregates everything in one place, allowing us as advisors, and our prospective clients, to build confidence in the decisions they're making when they invest in an annuity.

Henry Harrison: For those who don't know — I think pretty much anybody who's been in the investment world at all has heard of annuities, but they may not have a clear idea of what that means. I get that there are lots of different companies providing them, and instead of hooking up with one or two, you're screening the whole marketplace and trying to match the right annuity to the client. But what the heck is an annuity? You can probably define it better than me.

Jeremiah Konger: An annuity is a pretty broad term for a product that can generate income, but there are actually many different types of annuities that fall under that category. The two main functions of an annuity center around guaranteed income or protected growth.

If you break down the word, it comes from a Latin origin. The Roman militia was paid for their services in the form of an annua — a stream of payments. Annuities have evolved over time, and they've been around in our country for hundreds of years. Benjamin Franklin actually set up an annuity for the city of Boston, and it still pays out to this day because of the way he structured it.

The primary purposes are either to secure a guaranteed income stream — particularly for retirement — or to protect your money while still giving yourself a fair rate of return with no or limited downside risk from the markets.

Henry Harrison: Would you call this an investment? Does it fall under the category of investments?

Jeremiah Konger: That's a gray area. Some people will say an annuity is not an investment. It depends on the annuity type. If we look at an income annuity, in my opinion that's not an investment — it's more of a strategic tool you implement into a holistic plan, one that plays a significant role in how your income foundation is solidified for your retirement phase.

However, if you look at the other types of annuities designed for growth — an investment, in my opinion, is something you put money into that earns interest over time, and those growth annuities can do just that while also protecting your downside risk. So yes, an annuity can be an investment, but the primary purpose of an annuity is guaranteed income. Those income annuities are better recognized as a risk mitigation tool — specifically a longevity risk mitigation tool. If you live a longer life, you have to secure income to cover those years without depleting your nest egg.

Looked at from that perspective, it can actually be a growth optimization tool as well, because it takes the risk off the rest of your assets outside the annuity. That affords you wherewithal and time in the market — and we know more time in the market means more reward. So I like to look at it as an optimization tool and a risk mitigation tool, primarily.

Henry Harrison: And are you licensed or regulated? Explain a little about how that works.

Jeremiah Konger: To have the opportunity — the privilege, I always say — to offer these products and help put them in place for people approaching retirement or recently retired, you definitely have to have the appropriate licensure.

Annuities, particularly fixed annuities — which cover guaranteed lifetime income annuities and protected growth annuities — actually fall under the category of life insurance. So to offer those, you have to obtain a life license, or a life, health, and annuity license, depending on your state and what they call it. It falls under the insurance category of wealth, and it's governed by the individual state — so it's at the state level, not the federal level.

Henry Harrison: Okay. So put simply: people have money — cash, or stock, or some way to get cash — and they buy annuities, and those annuities provide them income. It's typically something done by people who are getting close to retirement or have retired, because they're trying to create an income stream to replace the income they were making when they were working. They've saved money all those years so they can live off that and other assets. And you help people do that in the best way for them.

Jeremiah Konger: Absolutely. I'm a retirement income specialist. My primary objective is to understand our prospective clients — their goals, their objectives — but more importantly, I really try to navigate the conversation around the emotional side of the planning. What will potentially keep them up at night? What do they have concerns about? What are their near-term and long-term objectives for this money? What does it need to do for them to know, when they get to the end of this retirement journey, that they made a good decision?

There are many different ways to create retirement income plans. But depending on the risk tolerance of the individual — and even when risk tolerance is generally high — we understand that the appropriate application of an income annuity can optimize very critical areas around the psychological aspects of retirement and continued investing.

When people approach retirement, it's a new phase many have never really thought about. They get within that five- or ten-year window and start to think about it, but they still don't understand how big an equation it is to solve. Our culture in America, as a capitalistic society, teaches us how to accumulate money. It teaches us how to get a job, start a career, contribute to a 401(k) or an IRA or a general savings account. But nobody teaches us how to decumulate that money once we've saved it. That's a bigger task and a much harder equation to solve, because there are tons of risks associated with the decumulation phase.

Think of it like going up a mountain. You're hiking to the pinnacle — the largest mountain in the world. I'm drawing a blank on the name.

Henry Harrison: You're talking about Mount Everest.

Jeremiah Konger: Mount Everest — that's what I'm thinking of. Exactly. Think about trekking up Mount Everest. The working path is going up — that's when you're figuring out your career, building your subject matter expertise, accumulating your assets, saving and compounding over time. That's your accumulation phase, maybe the first 30 or 40 years of your working career.

When you get to retirement, that's the pinnacle. Now you have to figure out how to get back down. More than 80% of all accidents or deaths on that Mount Everest trek happen on the descent — on the way down. Retirement is a very neat analogy for that, because there are far more risks involved with the decumulation of your assets. We don't have an idea of how long we're going to live — no one knows their expiration date. But we do know there's real potential to live longer than anticipated. There are studies showing that for a married couple today, there's over a 50% chance that one of them will live to age 95 or beyond. That's a significant probability.

When you think about living a longer life, longevity becomes a risk multiplier. The longer you live, the more exposure you have to the other retirement risks we face — volatility risk, taxation risk, healthcare inflation risk, general inflation risk, geopolitical risk. All of these risks become magnified when you live a longer life.

People approaching retirement may not think of it to that degree — obviously that's what I do and what I think about every day. But they do have some remnants of those thoughts, and they become almost intimidated: "What do I do? How do I navigate this?"

One of the questions I ask my prospective clients is, "When's the last time you took a withdrawal out of your 401(k)?" Many of them say, "Well, I never have." And I say, "Think about that. If you're relying solely on your market accounts to support your income, that means taking withdrawals every month out of that account — including when that account is potentially down."

Maybe we have unfavorable markets, maybe a very flat market, and now you're being forced to take income, because your lifestyle and expenses don't go away. If anything, when you retire, every day is like Saturday — your expenses increase. You're going out to dinner more, doing the things you like with your family.

When you package all of this up with the psychological aspects, it's a very daunting task to figure out. And as I said, there are many ways to generate retirement income plans, but when you look at utilizing tools, there's one that stands out from the rest in terms of sheer optimization — and I'm referring to annuities, obviously. Not just because I'm an annuity guy. I got into this because I learned all of these things leading up to starting this business, and that's when I said: this is something that needs to be magnified for the general population of retirees and pre-retirees.

So how does that optimization occur? Annuities are contracts. You're purchasing a lifetime payment that's contractually guaranteed and bound by the issuing insurance company. We're talking about companies that have been around for over 200 years — some of the biggest financial names in the world — backing up this income stream. No 401(k) can do that. No financial advisor who doesn't offer annuities can do that. No one is going to give you a signed, written contract guaranteeing your income will last forever. But an insurance company that offers annuities can. There's a lot of empowerment in that.

Think about the benefits psychologically, not just economically. The economics are the later part of the decision. I start with the psychological benefits, because when you build that foundation of guaranteed income beneath you, you're retiring to something solid — something you know will be there, that you can count on for the rest of your life, and for the rest of your spouse's life if you're married.

Think of it like building a house. What's the first thing that's laid? The foundation. In retirement, the foundation of your fiscal house is your foundation of income. And the more guarantees you can wrap into that foundation, the better. There are really only three recognized sources of guaranteed income in America today. That's pensions, if you're still blessed to have one. Social Security — some would argue it's not guaranteed and there could be changes down the road; true, but it's still recognized by many economists as guaranteed income. And the third is guaranteed income annuities.

Build that foundation to cover just your essentials. We're not saying put all your money into an annuity — that wouldn't be prudent, and it wouldn't be in your best interest. You put in as little as possible, but as much as necessary, to make that foundation concrete and solid enough to stand the test of time. I'm in Florida, so we use the term hurricane-proof. For a house to become hurricane-proof, it has to have a solid foundation. That's no different from your retirement plan.

It also gives you a different frame of mind — a different lens on how you build the rest of your retirement fiscal house. When you have that foundation under you, it becomes so much clearer to build the rest of the blueprint, because you know exactly what's underneath it and that it isn't going anywhere.

That's how I look at annuities and the proper way of applying them to a plan. From an optimization perspective, the peace of mind, the clarity, the confidence — and more importantly, the risk mitigation — is unparalleled. Then you combine that with the fact that all your other assets in the markets can be set-it-and-forget-it, just like the old Ronco infomercial with the rotisserie chicken. You don't have to think about what happens if the markets go down.

We know through studies that the time people get hurt the most in the markets is when they try to time the market — getting in and getting out. What actually matters is time in the market. The more time you're in, the more growth you can receive. The annuity allows you to stay put. It allows you to be disciplined and not have that fear or preservation mentality over the remaining assets in the market, because we know the markets always come back. It's just a question of how much time it takes to get back to even and then exceed it.

There was a study — I think it was Dalbar — that looked at this. If you miss the 10 best days in the market each year, your returns are cut in half. If you were in the pure S&P 500 and it went up 10%, missing those 10 best days means your return is now 5%. Miss the best 20 days, and your return is two and a half percent. Think about that — miss those 10 or 20 best days and your returns aren't even pacing inflation.

The annuity allows you to stay put with peace of mind and confidence, knowing you have bounce-back time. You can ride the rollercoaster, let it get back up to even, and you're golden. It optimizes your growth long-term. So if you have legacy goals, a bequest you want to leave, or you just want to build a bigger nest egg — it's proven. I've modeled it. Over a 30-year horizon, a modern retirement plan with an annuity serving your guaranteed income essentials will outpace a pure 60/40 or 50/50 equity-bond portfolio, which is the traditional method. I've modeled it over every historical period in our economic history.

Henry Harrison: Really, the fear you're talking about when people retire is that they're either working less or not working at all, they have their savings, and they don't want to run out. Obviously, if they're selling when the stock market has just dropped by half — and that's where all their money is — that's a bad time to be selling. So if they have this annuity income, they can cover their expenses and don't necessarily need to sell then. That would be one of the goals, in layman's terms. Do I have that right?

Jeremiah Konger: Absolutely. I always ask my clients and prospective clients, "When you retire, what else retires with you?" Sometimes they draw a blank or don't know where I'm going with that. Sometimes people get it right and say, "Well, my income. My income is retired."

You're hanging up the gloves, hanging up the boots — or the stethoscope; maybe you're a nurse. My mom's a nurse, so that's why I use that one. When you hang those things up, your paycheck also retires. Many people go 40 years in their career getting a paycheck every two weeks or every month, and it becomes part of them. As Americans, it's not how much we've saved that gives us our sense of security — it's how much income we're getting consistently. I always say retirement runs on income, no different from the rest of your lifestyle.

So when you retire that income stream, things start to get a little hairy. You start to worry. And then the markets and all these other uncontrollable things do what they always do. There will always be the next crisis. There will always be the next president you don't like in office. There will always be the next war or conflict. All of those things impact the markets, and you don't control them.

I always say: if you don't tell your money what to do, it's going to tell you what to do. If the money's in the market, the money is telling you what to do — you have no say in that discussion. But if you empower yourself to change that dynamic and put control on your side, at least on your bottom-line income, that's what the annuity does. It creates empowerment, and then it creates wherewithal. So you're right — hanging up the gloves means retiring your income, and that's our security. How do we get that security back? That's what annuities do, and they do it very well.

Henry Harrison: When you were growing up — your mom was a nurse — did you ever think you'd be an entrepreneur, or into annuities, or some sort of investment or guaranteed income like we've been talking about?

Jeremiah Konger: Maybe not initially, when I was very young. I was like most elementary-aged boys — I wanted to be a baseball player. That was a passion of mine. I loved baseball growing up and played my entire childhood.

But as I grew up, I learned the value of a dollar. My mother was very adamant about teaching me the value of money and how to save. I come from a lower class background — I don't even know if I'd say middle class. My mother was a single parent, so there were a lot of challenges. But growing up, I had influences from my uncles, and my grandfather was an entrepreneur, so I saw the successes they had.

I started working at a very young age — lugging around a push mower and a little two-and-a-half-gallon gas tank, knocking on doors in my neighborhood, mowing lawns for five or ten bucks a lawn. I always had an innate craving for having money. I wanted to make my own money.

I never thought about owning my own business until I was around 16. I was working at Circuit City back in the day, in the entertainment department — the big screens and the plasma TVs when they were first coming out. They were amazing, but super expensive. When I first started, the plasma TVs were $15,000 or more.

I remember I had one of the biggest ticket sales of all time in that store. A gentleman came in one night with his wife and family, and they said, "All right, pick out which one you want." They picked out the big daddy plasma — that thing was at least $15,000. And then he picked out not only that but the full surround sound, all the top-of-the-line cables, everything you could think of to make his living room the most incredible entertainment experience. The ticket was over 34 grand.

When I was ringing him up, I asked him, "Sir, if you don't mind me asking, what do you do for a living?" He was in real estate — a broker, but he specialized in investing in his own multifamily investment properties. From that moment on, my mind really started gearing up: I want to own my own business. I want to invest in real estate or something along those lines. Ever since then, that's the path I've embarked on — building my acumen and skill sets in areas that would help me be successful. That's what led me here. I'm very honored and privileged to have that opportunity.

Henry Harrison: And you've got a good team — it's not just you, right? You probably started out with just you, but you've grown it. How many people, roughly?

Jeremiah Konger: We're pretty lean. We have, I think, 15 individuals total now between advisors and client success managers. We actually just bolted on Medicare as another service within our company, so we have a Medicare specialist now. So yeah, we're around 15 people, but we're remote, so we run lean. It's definitely a privilege to have this company and make an impact on lives in a multitude of ways — whether that's the general public or within our employee base as well.

Henry Harrison: And when you started this, how did that come about? Did you just say one day, "Okay, now is the time — make the leap"? Or did something happen? Is this seven, eight years ago now?

Jeremiah Konger: We incorporated at the end of 2018, I believe, so eight years now, going on almost nine.

I didn't start out of the gate saying I wanted to be in financial services. That came later. I knew I wanted to be an entrepreneur from that moment I mentioned — meeting that gentleman at Circuit City. At the time, I actually got recruited within Circuit City. Another guy came in one evening — his name was Keith Sedlowski. I don't talk to him anymore, so if he's listening out there, hey, Keith.

He came in one night having heard from another employee who'd been recruited to Nextel — the company Keith represented; he was a store manager across the street. Keith had asked one of the guys they recruited from Circuit City, "Who's the top guy over there? I want the best of the best — the guy who lights up the leaderboard every week." And they said my name. A guy named Eric Bresser said my name.

So Keith came in one night to shop me. He acted like he was going to buy a TV, and I took him through the whole thing. My biggest passion has always been helping people — it's never been about making a sale. It's about understanding what someone is trying to accomplish and then right-fitting the solution. So I took him down that path: "What are you looking for?" The whole qualifying process. Long story short, we got to the end, we were about to ring things up, and he said, "Hey man, let's cut the you-know-what. I want you to come work for me."

I was always open to new opportunities, but I'm loyal — they treated me pretty well at Circuit City. He said, "Just come talk to me Friday evening and we'll figure it out." Long story short, I got the job. And I did both, because I didn't want to burn any bridges — I didn't want to take a leap of faith, have it not work out, and have burned that bridge. So at 17 or 18, just out of high school, I worked full time at both — 40 hours at each location. They were right across the street from each other, so I'd finish one shift and immediately go over to the other.

I fell in love with the wireless industry. It was a very fun industry to be in — it was just starting to experience a lot of innovation and growth around technology. I had the opportunity to sell the first smartphones — literally the first smartphone. I did really well and excelled there.

After about a year or two, I transferred to go to college in Tallahassee and transferred my store location there. That store was what they called a top-100 store — volume-wise, one of the busiest in the country. I excelled, did what I always did — helped people get what they want — and got promoted to management very young. Then I got recruited again within Sprint and Nextel to join the prepaid side of the brand and launch a new territory.

I became a territory manager for Boost Mobile, which was the prepaid brand back then — one of the fastest-growing wireless brands in the country at the time. My job was to find retail stores that would sell and distribute those products — mom-and-pop stores, people already selling in the same line. I'd go into malls, find the kiosks selling cellphone cases, and say, "Hey, you want to sell Boost Mobile phones?" Over time I built a very vast network of independent retailers, and my territory was one of the top in the country. I won MVP awards and so on.

At that point I struck up a relationship with a gentleman who ended up becoming the largest independent retailer for Sprint's prepaid brands. He was a younger guy — maybe 15 years older than me, but for that line of work he was pretty young. I was only 20, so he must have been in his mid-30s. This guy had a mind like I'd never experienced. I'd like to say I have a similar mind now because of that experience. He just thought differently.

He was massive on marketing — that's where he won. It wasn't just putting a sign on the exterior of the store and praying someone comes in. This guy owned his market. He was on radio, TV, flyers, mailers, sign spinners — you name it, he did it to the nth degree. He became the largest and fastest-growing retailer in that space. I was recognized for it, but the effort and hard work went to him — I can't take credit for that.

But I learned how he did things. I learned how he operated his business — marketing and operations, training his staff, who he hired and what those personalities were like, the experience his stores delivered. When you walked into them, they felt completely different from any other Boost Mobile store at the time. In fact, his stores were what Sprint Nextel emulated. They saw his stores and thought, if we make this a requirement for our retailers, maybe our sales change. They implemented it — the requirements to become a retailer meant putting real money into the build-out, whereas before, when the brand was just getting off the ground, as long as you had a business address and an EIN, you could sell the phones.

I learned all of this, and by the time I was 23, I was still in that role — expanding the market, opening up new doors, as they called stores. I was planning to move to Southeast Florida, and there was a territory that was wide open. That's when I said, "Maybe it's time. Maybe I'm going to hang up my gloves as a corporate employee." I had enough money saved. I knew the business — I was helping people succeed in it every day. So I took the leap of faith, opened my first store, and retired my paycheck from that job. I became completely reliant on that one store.

That one store quickly grew. I owned the market and became the fastest-growing retailer in that area. It ended up being 12 stores in total. Right at the end of that, we sold — and then opened up another dozen stores with T-Mobile. We essentially got promoted, as independent retailers, to the brand that was exploding, which was T-Mobile. We ended up with 12 stores there and eventually sold those too. That's when I got into this.

That's really where I learned the ability to market, to create a sound operation, and to build a client experience that's unmatched. And I always had a knack for finance. My mother taught me the value of a dollar, so I've always been good with saving and investing money and helping friends and family build their acumen in that area. That passion for finance is what led me here.

When I sold those stores and was looking for the next thing, I got recruited, in a way. Headhunters were reaching out — I had a resume out on Indeed, I think it was. I spoke to some people, and initially, you hear "insurance," "life insurance," "wealth planning" — not everybody wakes up saying they want to offer life insurance. That's kind of a hard gig to figure out. But after a while, I met a really brilliant individual who wanted me to join his team, and I took a leap of faith and tried it out. That's what eventually spawned Annuity Association. Within a short period of learning that business and seeing the opportunities that existed because of the fragmentation and antiquated methodology, I knew there was a better way — and that's what spawned the thought of annuityassociation.com. I know that was a long-winded answer, but that's how we arrived.

Henry Harrison: No, it's a nice story. So you had 12 stores, or 24? You went from one to—

Jeremiah Konger: We had an initial 12 that we sold, and then we reinvested in another 12.

Henry Harrison: And then you sold those?

Jeremiah Konger: Yes.

Henry Harrison: So you had two liquidating events. And you were probably also of a mindset — at a young age, you had some capital accumulated, and you didn't have a paycheck. The thought of "Where am I going to get my income?" becomes a little more real, because you have some money, but if you're just spending it every day...

Jeremiah Konger: That's true. That would be one of the harder parts of this journey so far. I was in that phase where I didn't know exactly where I wanted to go. I knew I wanted to start another business — I just didn't know what industry. I was looking at so many different things: more wireless opportunities, franchises in my local market at one point. I had my resume out there and was getting hit up with different financial services opportunities.

Over time, the money started to dwindle. The money we scored on the sale — I started to feel the crunch. I'm not going to lie about it. I won't say I acted out of desperation — that's never the right way — but I did feel like, hey, I might just have to do something to get some cash flow coming in, even if that meant going back to work as a W-2 employee. I was willing to do that.

But luckily, I had a great interview with a gentleman at a smaller insurance marketing organization. Their whole claim to fame was offering mortgage protection insurance, which helps younger families secure their mortgage debt in the event of the untimely or sudden death of the primary breadwinner. It was something I believed in — and I had to believe in what I was offering. It truly helps people.

There was actually something that struck close to home. My grandmother lost her husband — my grandfather — in 1990. I was only three or four years old at the time. My grandfather was the breadwinner; my grandmother was fortunate to be a stay-at-home mom, and she had eight children, my dad being one of them.

Henry Harrison: Wow.

Jeremiah Konger: He was an avid fisherman and scuba diver, and he was scuba diving in the Gulf of Mexico at about 120 feet when he had a massive heart attack underwater. He was coast-guarded out to the hospital and died on the way. My grandmother was left in a very tough spot, because he didn't have life insurance and he didn't have mortgage protection insurance.

I thought about it, and I realized: if he'd had this, my grandmother wouldn't have gone through the financial ruin she ended up going through. She lost her home. She went into a depressive state where she didn't care about anything — money included — and ended up losing the home because she defaulted. I think there was also something to do with taxes. My grandfather built that home from the foundation up.

She lost all of his assets. He had a business — he actually owned the largest garage door business in the greater Tampa area at the time — and it went bankrupt. It couldn't be sold because no proper succession planning had been done. He had a bunch of commercial buildings; she lost those too. Long story short, she became financially destitute because of this event. Luckily, my uncles and my dad were able to help her out for the rest of her life — but not everybody has that to fall back on, nor do many people want to lose dignity by relying on other people.

So I believed in the product of mortgage protection. That's what got me to give it the green light. Then I started learning financial services and what other areas of financial planning existed, because I'd found a need. I thought: what else is out there? How else can I serve people? That's when I found retirement planning and the fact that many people go into retirement without a plan — I want to say over 40% of people retire with no formal plan. That's a massive need. It's almost a crisis, because they're setting themselves up for a bad day if they don't have a plan to mitigate it.

That company offered very few annuity products. When I started to learn about retirement income planning, I got passionate about it. I went to Brad, the guy who recruited me, and said, "Hey, I've got this client who's a primary candidate for an income annuity. They just retired, they're trying to figure things out — which product should I show them? What are the products?" And he said, "I don't know, man. Just pick one of them and learn about it. Read the brochure and go tell them the story from the brochure."

To me, that was so wrong. I couldn't do that — I couldn't get behind it if I didn't believe in it myself. So I reached out to the corporate person at that company and said, "I want to know all the products. How many do we have?" The number was 15. Fifteen products — some for income, some for growth. And I said, "From my research just on Google, there are about 500 different products out there. How do we only have 15?" And he said, "I don't know, man. That's just the way it is. That's the way this business is run. You get a couple of carriers you build relationships with, and then you sell their products. The more you sell, the more commissions you make."

And I said, "This is wrong, man. This is so wrong." I'm sitting in my bed one night, Henry, thinking about this, and I had that light-bulb moment: that's it. I'm going to take this problem I've found — and this opportunity to solve it — and I'm going to do it. I'm going to take the leap of faith.

I was on GoDaddy that night, typing in URL names, trying to think of the business name — annuity this, annuity that — and everything was taken or for sale at a big asking price. Then I typed in annuityassociation.com, and it said it was available for something like $14. I thought, did I spell this wrong? Did I spell annuity wrong? Association? Long story short, it wasn't spelled wrong, thankfully. I bought it, secured it, and hit the ground running from that point on, with the mission that we would be educational first, transparency first, and trust first — and there's no first, second, third. All three of those together are the first priority.

We've struck up relationships with every major annuity provider in the country. We leverage technology to filter all the information, and we offer a very interactive process to help people make more confident decisions — to know they're not buying the wrong annuity or being sold something that isn't the best value. They get to see it with their own eyes. It's no different than when you go to a steakhouse and it ranks the steaks based on the profile you want. That's the way we treat this. It goes from being sold something to being empowered to buy something with confidence.

Henry Harrison: Just to tie up one end you mentioned — life insurance. There are annuities that pay income and also provide life insurance. Without going down that whole path — as you said, there's a vast number of choices, and you can empower and guide people based on their goals toward the best choice. But certainly life insurance is one part. I don't know if it's literally annuities — I'm getting over my head with the lingo.

Jeremiah Konger: Think of it like this: life insurance is really designed to replace the future income that you never earned. It's generally positioned for a younger professional who's just starting out, building their family, their home, and their nest egg. The real design of life insurance is to replace future income that would have been earned if the person hadn't died early. It's ideal for situations like this: you have a five-year-old daughter or son, and you pass away at 35 or 40. That child would be more challenged to afford college — but a life insurance policy fills that void.

There are many applications of life insurance, but I tend to think it's for a younger phase of life, to replace future income. An annuity is the opposite. It's there to replace the income you're retiring — for your current needs, for now, so you don't run out of money. That would be the relationship between the two. Am I addressing that?

Henry Harrison: I was thinking — you also sell life insurance to help families. But isn't there also a product for people who have an estate they're going to pass down? There are annuities, and then there's—

Jeremiah Konger: Cash value life insurance.

Henry Harrison: Cash value insurance, yes.

Jeremiah Konger: As I said, there are many applications of life insurance and how it can fit into an overall plan. With cash value life insurance — or life insurance in general — the death benefit is generally recognized as tax-free. Those vehicles can sometimes be leveraged to offset estate taxes and can be part of an estate plan. They can also be used to shield assets from creditors.

The one primarily used for estate planning is a whole life or indexed universal life structured policy that builds cash value. That cash value can be used for income in a way that's also recognized as tax-free, and there are death benefit provisions recognized as tax-free as well. It just depends on the true need. There are many ways to leverage that product.

Henry Harrison: Sure. I just wanted you to touch on that, since I knew it was part of your expertise and offerings. Well, I know you've won some awards. Maybe to wrap up, you have some achievements that might be worth sharing, and then we can call it a day.

Jeremiah Konger: Absolutely — and I definitely appreciate the opportunity to share our story. I'm not real big on bragging.

Henry Harrison: I'm pulling it out of you.

Jeremiah Konger: It's more a byproduct of doing the right thing — serving and helping people get what they need or what they want. We were recognized by Inc. 5000 last year as one of the fastest-growing private companies in America. We ranked 294th on that list. A kid from the Tampa area — growing up, I never fathomed that would be a list I'd be part of. I think it's pretty prestigious, at least where I come from, so it's nice to be recognized.

But again, it's a byproduct of doing the right thing, helping people, and really solving problems. That's where all of these accolades come from — including money. The bigger the problems you can solve for people, the more the money is just a byproduct, and these accolades are the same.

We also just qualified for a Hall of Fame recognition from one of our partnerships within the annuity distribution industry — that channel is called an IMO, an insurance marketing organization. We've only been in business with that IMO for just over five years, and to meet the qualification you have to have done over $100 million in annuity production. We were one of the fastest to achieve it — we did it within five years. We're pretty proud of that.

And last but not least — I think the most important thing here, and I appreciate everybody's time in hearing my story — is continuing to build on our mission, which is to help people make clearer retirement decisions. If an annuity is one of the products that fits into that picture, we're passionate about helping people make better annuity-buying decisions. We do that through trust and education, ultimately empowering you to know what you're getting for your hard-earned money. We have a framework we teach you for evaluating these products.

What we've done now is launch our direct-to-consumer annuity buying platform. We understand there are people out there who are very intelligent and very aware of what they want and need — I call them DIY investors. They don't need a financial planner or an investment professional. All they need is access to the solution. So we built a platform called nesteasyannuities.com — a direct-to-consumer buying platform that gives you access to all of the annuity products in one place.

Again, we get away from that fragmented, antiquated methodology. We give you everything to look at — compare rates, companies, financial stability ratings of the insurer, the whole nine. You can quote on your terms and build your annuity IQ, so that hopefully you're empowered to buy when you're ready, on your terms. There's no sales pitch, no smoke and mirrors. You like what you see, you click a button, and you buy direct. It's one of the first of its kind. We're really innovating and disrupting our space for the betterment of consumers.

Henry Harrison: Well, that's terrific. We'll get you a whole new show on that. But for today, we'll celebrate a good time together. It was really great to get to know you better. I look forward to staying in touch, and thank you for coming on.

Jeremiah Konger: The pleasure's been mine. I appreciate the time, Henry, and I look forward to possibly being on again soon.

Henry Harrison: Great.

Jeremiah Konger: Thank you.

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