Tax Strategies & Wealth Protection for High Earners | Dan Pascone with Ashleigh White | Podcast #01

High earners and successful business owners usually don’t have a tax problem they have a tax-planning problem. In this episode, Dan talks with Ashleigh White, VP of Sales & Marketing at Fortress Brokerage Solutions, about how her firm uses advanced insurance and risk-management strategies to reduce estate and income tax exposure, create powerful “golden handcuff” packages for key employees, and help executives save far more than traditional retirement plans allow. They dive into estate tax mitigation using life insurance, non-qualified deferred compensation for top earners, executive benefit design for law and medical practices, how AI is transforming life insurance underwriting, and why education and the right partners (CPAs, estate attorneys, advisors) are crucial for getting these complex strategies right.

• Who Ashleigh & Fortress serve: Fortress Brokerage Solutions is a brokerage firm focused on insurance and risk-management strategies for:

  • High-earning, high-net-worth individuals facing current or future estate tax issues (federal and/or state-level)
  • Business owners & professional firms (law, medical, etc.) that want to recruit and retain key talent
  • Executives who are “maxed out” in qualified plans but still need to save substantially more for retirement


• Estate tax as a real-world problem: Many states have their own estate or inheritance tax, sometimes kicking in around $1–2M in net worth. Families can be hit with large tax bills even if they’re far from “ultra-wealthy,” unless proactive planning is done.


• Using life insurance to solve estate tax issues: Fortress helps clients design risk-management (life insurance) structures that:

  • Create liquidity to pay estate taxes when due
  • Allow children or heirs to be “made whole” instead of forced to sell assets fast
  • Integrate with estate planning tools (like ILITs) built by attorneys


• Executive retention & “golden handcuffs”: On the business side, Fortress helps companies:

  • Design custom executive benefit plans to keep C-suite and rainmakers from going “down the street” for a bit more salary
  • Offer life insurance, tax-free retirement income, and potential long-term care benefits as part of a long-term package
  • Align benefits with the employer’s retention and recruiting goals


• Non-qualified deferred compensation (NQDC): For high earners hitting 401(k) and qualified-plan contribution caps, Fortress structures NQDC plans so executives can:

  • Defer more income on a customized basis
  • Match savings to their higher lifestyle and retirement goals
  • Potentially access tax-advantaged income later in life


• Everything is truly tailored: Fortress doesn’t push one product. They start by asking:

  • “What’s your real goal: tax reduction, retention, income, legacy, or some mix?”
  • “What’s your budget and time horizon?”

  From there, they build a case-specific design instead of a cookie-cutter package.



• Key partners & referral sources: Fortress rarely works in a vacuum. Their best relationships are with:

  • CPAs who know which clients have acute tax problems or big pending liquidity events
  • Estate planning attorneys who need insurance integrated into trusts and legacy plans
  • Attorney firms & medical groups with highly compensated partners they want to keep
  • Financial and insurance advisors who lean on Fortress for advanced case design


• How they collaborate: Ashleigh spends a lot of time:

  • Joining joint calls with CPAs, attorneys, clients, and advisors
  • Recording videos and educational materials for partners to send to clients
  • Helping M&A pros and SBA loan advisors structure needed coverage around deals


• AI is changing the insurance world: Carriers are increasingly using AI and automated underwriting to:

  • Review medical records far faster
  • Offer instant approvals in as little as 15 minutes, sometimes even on holidays
  • Autobind up to very high death benefits (e.g. $170M) with minimal hassle in the right cases

  This is turning a once slow, paper-heavy process into something much smoother for high-end clients.



• Ashleigh’s role: As VP of Sales & Marketing, she:

  • Leads outbound messaging to both end clients and professionals
  • Acts as the “I’ve got a guy and don’t know what to do” resource for advisors
  • Does the actual case design herself in-house, tailoring solutions client by client


• Biggest challenge: awareness & education. Most people don’t know:

  • That they have a looming tax or liquidity problem; or
  • That advanced insurance planning could solve it.

  That’s why Ashleigh is all-in on education via YouTube, joint webinars, and deep-dive conversations with clients and their advisors.



• Lightning round themes: In the rapid-fire segment, we learn that:

  • Ashleigh is a tea person and a dog person
  • Her must-have tech is a heart rate monitor at the gym
  • Her favorite finance book is Rich Dad Poor Dad
  • A key money lesson: don’t borrow from your 401(k) lightly
  • Her big financial goal: becoming a millionaire
  • Advice to her younger self: start saving earlier


• How to connect: Ashleigh invites listeners (and their advisors) to reach out via Fortress Brokerage Solutions by phone or email; Dan notes that her full contact details are in the show notes.

• 00:02 – Sponsor & show intro. The episode is brought to you by Tailored Wealth; the show’s mission is to cut through financial noise for business leaders.
• 00:32 – Dan sets the stage. Dan welcomes listeners and explains the podcast’s purpose, help people take control of finances, minimize uncertainty, and maximize wealth potential.
• 01:00 – Meet Ashleigh. Dan introduces Ashleigh White, VP of Sales & Marketing at Fortress Brokerage Solutions, noting her work with business owners and executives on tax optimization.
• 01:20 – Ashleigh’s background & family legacy. She shares that she’s third generation in the financial services industry: her grandfather was a major John Hancock advisor; now she, her father, and grandfather have all been in the business.
• 02:08 – What Fortress Brokerage Solutions does. Ashleigh explains that Fortress is a brokerage firm for insurance and risk-management products used to:

  • Transfer risk off the client’s balance sheet
  • Create meaningful tax deductions for individuals and corporations
  • Address large estate and corporate tax liabilities now and in future years


• 03:24 – Ideal clients & estate tax focus. She describes ideal clients as:

  • High earners and high-net-worth clients with estate tax problems
  • Those living in states with state or inheritance taxes (not just federal)

  Fortress uses life insurance to ensure heirs can pay taxes and be made whole.



• 04:20 – Business-side solutions. Ashleigh explains how Fortress designs:

  • Special executive benefit packages for key employees and C-suite leaders
  • Programs that provide life insurance, tax-free pension-style income, and LTC benefits
  • Structures to keep top talent through retirement and beyond (“golden handcuffs”)


• 05:23 – Non-qualified deferred compensation. For executives maxing out 401(k)s, Fortress carves out the executive group and sets up NQDC so they can save at levels aligned with their income and lifestyle.


• 06:31 – What makes Fortress different. Ashleigh emphasizes the tailored, goals-first approach:

  • No one-size-fits-all schemes
  • Everything starts with: “What’s your goal and what problem are we solving?”
  • They integrate CPAs, estate attorneys, and financial planners as needed


• 08:12 – Key referral partners. Dan asks how clients find Fortress; Ashleigh highlights:

  • CPAs as a major source (they see the tax pain first)
  • Attorney firms & medical practices who need to retain lucrative producers
  • Estate planning attorneys who require life insurance in trust-based strategies
  • Financial/insurance advisors who need advanced case design


• 11:47 – How Fortress collaborates. She describes:

  • Three-way calls and joint meetings with other advisors
  • Co-branded videos and flyers explaining Fortress’s role
  • Helping M&A and SBA loan professionals add proper insurance around deals


• 12:57 – The rise of AI in underwriting. Ashleigh talks about:

  • AI reviewing medical records faster than humans
  • Instant approvals even on Christmas Day in under 15 minutes
  • Carriers autobinding up to $170M of death benefit with minimal underwriting in some cases


• 14:23 – Smoother client experience. These innovations mean less hassle and delay for savvy clients who once had to endure long, paper-heavy underwriting processes.


• 15:04 – Ashleigh’s day-to-day. As VP of Sales & Marketing, she:

  • Leads outbound marketing
  • Fields complex cases from financial professionals
  • Personally builds the tailored case designs for Fortress clients


• 16:34 – Biggest business challenge: getting the word out. Ashleigh explains that:

  • Most people don’t know they have a problem until a professional points it out
  • Education via YouTube and nuanced outreach is crucial
  • Success starts with professionals initiating honest conversations about tax, risk, and legacy


• 18:39 – Dan on education & tailored solutions. Dan echoes that personal finance is deeply personal, and that tailored strategies—not one-size products—are essential for serious clients.


• 19:57 – Lightning round. Dan hits Ashleigh with quick questions about coffee vs. tea, cats vs. dogs, must-have tech, favorite quote, favorite book, personal finance hacks, bucket list items, big money goals, money mistakes, and advice to her younger self.


• 23:43 – How to contact Ashleigh. She shares her phone, email, YouTube, and website. Dan promises everything will be in the show notes.


• 24:08 – Close & sign-off. Dan thanks Ashleigh, encourages listeners to connect if they need advanced tax and insurance strategies, and invites everyone back for more episodes of Making Sense of Your Money.

In this inaugural episode of the series, Dan sits down with Ashleigh White, VP of Sales & Marketing at Fortress Brokerage Solutions, to unpack how sophisticated insurance-based planning can help high earners and business owners reduce taxes, retain key people, and build more secure, tax-efficient wealth.

Ashleigh comes from a three-generation financial services family. Her grandfather was one of the biggest John Hancock advisors in his region; her father followed; and now she’s carrying the torch at Fortress. The firm acts as a brokerage and design shop for advanced insurance and risk management strategies not just term policies, but complex structures that integrate with tax and estate planning.

On the individual side, the conversation quickly moves into estate tax. Many people assume estate tax is only a federal concern, and only for the ultra-wealthy. Ashleigh points out that several states have their own estate or inheritance taxes at much lower thresholds, sometimes around $1–2 million. That means a “comfortable but not ultra-rich” family can still face a tax bill that forces them to sell assets at the worst possible time.

Fortress uses life insurance as a liquidity and tax-planning tool, not just a death benefit. Properly structured policies often within trust-based estate plans can provide the cash needed to pay estate taxes, allowing children or heirs to keep businesses, real estate, and other legacy assets intact. The goal: “make the children whole” instead of leaving them scrambling.

On the business side, Ashleigh talks about the challenge of recruiting and retaining key talent. Law firms, medical practices, and other professional organizations often have a small group of rainmakers who are essential to the firm’s value. Losing them to a competitor “down the street” for a slightly higher salary is a real risk.

To address this, Fortress designs custom executive benefit packages that go beyond salary and bonuses. These can include:

• Life insurance as part of their compensation
• Structured plans that create tax-free retirement income
• Long-term care benefits or other protection for later life

Put together well, these packages become powerful “golden handcuffs” benefits that are too valuable to walk away from, especially when tied to tenure or performance milestones. They also give owners a more predictable way to reward and retain their leaders over the long term.

Another theme is the limitation of traditional retirement vehicles. Highly compensated executives often max out their 401(k)s and other qualified plans but still can’t save at a level that matches their lifestyle and retirement goals. That’s where non-qualified deferred compensation (NQDC) comes in. Ashleigh explains that Fortress frequently carves out an executive group and builds a custom NQDC plan to let them defer more income and build meaningful future benefits in a tax-efficient manner.

Throughout, Ashleigh stresses that Fortress is not a product pusher. Everything starts with questions like:

• What is your biggest problem taxes, retention, liquidity, or something else?
• What outcome are you really aiming for?
• What’s your budget and timeframe?

From there, she and her team construct customized strategies that might tie together life insurance, NQDC, buy-sell funding, key person coverage, or other tools. They’re also comfortable stepping into a “middle of the table” role, working collaboratively with CPAs, estate planning attorneys, financial planners, and M&A professionals to get the structure right.

The discussion then pivots to technology and AI. Insurance underwriting has historically been slow and painful, especially for large cases. Ashleigh describes how AI is now used to analyze medical records quickly, enabling some carriers to issue instant approvals even on holidays within about 15 minutes. In certain scenarios, carriers can autobind up to $170 million in death benefit with minimal underwriting if recent medicals are available. For high-net-worth clients, this is a dramatic change: long, drawn-out underwriting is being replaced by a much smoother process.

When Dan asks about her biggest challenge, Ashleigh is clear: it’s awareness. Most people don’t realize they have a looming tax, liquidity, or retention problem until someone sits them down and walks through the numbers. Because money is so personal, many people also hesitate to proactively seek help. That’s why she leans heavily into education, including YouTube content explaining things like buy-sell agreements vs. “key man” insurance and other nuanced topics.

The episode closes on a more personal note with the lightning round. We find out Ashleigh prefers tea over coffee, dogs over cats, relies on a heart rate monitor at the gym, loves Rich Dad Poor Dad, wants to become a millionaire, and warns against borrowing from a 401(k) without fully understanding the consequences. Her advice to her younger self is simple but powerful: start saving younger.

Dan wraps by encouraging listeners who face significant tax exposure, complex estate issues, or executive retention challenges to connect with Ashleigh and Fortress Brokerage Solutions and to keep following Making Sense of Your Money for more conversations that blend tax, planning, and real-world business strategy.

Announcer: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Announcer: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.

Dan: All right, good afternoon, morning, evening, wherever you are, and welcome to another episode of the Making Sense of Your Money podcast.

Dan: I am your host, Dan Pasone, and uh we here help you to take control of your finances, minimize uncertainty, and maximize your wealth potential here at uh Making Sense of Your Money and our podcast as well as our content.

Dan: Brad, super excited for today's episode. We uh have a special guest with us today. We've got Ashley White who is the VP of sales and marketing for the Fortress Brokerage Solution.

Dan: And Ashley and her team do some amazing work with business owners and executive leaders to help them in uh in the tax space and help them to optimize their tax situation, which is a concept that I am super, super passionate about, very uh very near and dear to my heart.

Dan: So Ashley, thanks so much for joining us on the Making Sense of Your Money podcast. Happy to have you today.

Ashleigh: Thank you for having me. Appreciate you having me here.

Dan: Yeah, you bet. You bet. We're going to have some fun. So, we got a lot to cover and uh you know, we've got a great audience that I know would love to get to know you as well as your expert on some uh on some topics. So, if it's okay with you, we're going to hop right in.

Ashleigh: Sounds good. Looking forward.

Dan: Let's do it. All right. So, first and foremost, why don't you just do a uh quick 90-second overview of what your business does and then tell us a little bit about how you got into the business as well.

Ashleigh: Absolutely. So, Fortress Brokerage Solutions is a brokerage firm for insurance products, risk management products that we use to help people leverage risk that they maintain on their side and also provide the ability to get some crucial tax deductions for individuals and corporations, especially if they're coming up against some large tax bills, whether it's an estate tax bill or the corporate tax, and what they can do for now and maybe some years into the future to reduce that liability in order to retain important individuals in their company and also recruit them.

Ashleigh: So there's a number of things that we do both for individuals and corporations.

Ashleigh: I myself found myself in this industry, in the financial services industry, about 10 years ago. I got my license but it's because I am actually third generation in this industry. My grandfather was probably the largest John Hancock adviser in the mid east in Midwest.

Ashleigh: So, it really trickled down from there and it's myself, my grandpa, my father. We're all in this business together. So, I've been around it my entire life.

Dan: All right. A family of financial service leaders. I love that. I love that. Very, very cool. Very cool. All right. That's amazing. Thanks for sharing that.

Dan: Tell us a little bit about your ideal client and what Fortress ultimately helps them to do. Like walk us through like the client experience and what they get from working with your firm.

Ashleigh: Sure. So we have probably several niches of ideal clients. The first one would be high earning and high net worth individuals that have an estate tax problem.

Ashleigh: Estate tax problem is generally thought of as a federal tax bill. However, I I believe there's about 15 to 18 states that have a state or even an inheritance tax.

Ashleigh: So, for those individuals those can be low figures, anywhere between 1 million, 2 million if you have a net worth above that, your your family is going to get hit with an estate tax bill at the state or even federal level. We help people to mitigate that tax, that estate tax, so that their children can be made whole. We do that using risk management products, namely life insurance.

Ashleigh: So that's from the individual perspective.

Ashleigh: From the from the business perspective, we do a number of things. We can help the business build a special package for their employees which can help them recruit employees and retain extremely important people, especially the C-corp, uh the the the C-suite level of individuals, uh the people that you don't want to lose to someone down the street, right?

Ashleigh: And that will help them make sure that their employees have a good path through to retirement, that they're staying with them till then, and then when they retire leave with some kind of special program that's going to give them life insurance, that's going to give them tax-free pension income, that's going to give them maybe a long-term care benefit and really take care of them for the long haul.

Ashleigh: So, it's it's a special program that we do.

Ashleigh: We also can provide a way for high earners in a company that aren't being able to save as much as their lifestyle would require them to when they want to retire, because they have maximums and they're already maxing them out and it's not enough, right?

Ashleigh: That will allow us to carve out the executive group and put them into a special non-qualified deferred compensation program so they can also save more for themselves and their retirement and their families.

Dan: Yeah, that's a that's a that's a great topic and one that we talk to our clients about oftentimes.

Dan: You know, you've got high earners that, to your point, can't save enough, especially folks that are in from a lifestyle perspective. I talk to folks a lot about this concept of hybrid or phase retirement. We have a lot of sort of high earning hardworking executives that want to get to an earlier phase retirement where they're doing more purposeful work, more flexible work, but they're out of sort of the day to day grind that they've been used to.

Dan: The inability to save enough in a given year in those retirement programs is a real, real challenge. So, it's good to hear that your your company helps with that.

Dan: Okay. Tell us a little bit about this. This seems very, very unique because I don't I don't hear a lot of firms talking about this stuff, but tell us a little bit about what makes you and your firm unique in the way that you help your clients to achieve these outcomes.

Ashleigh: Absolutely. Everything we do is a tailored approach. There is no one size fits all program, right? We are taking a look at whether it's an individual or the company. What is your ultimate goal? Is your ultimate goal to save on tax? Is your ultimate goal to provide a golden handcuffs style program for your employees?

Ashleigh: We're always going to focus in on that goal and then provide a solution to meet the problem that they're coming up against.

Ashleigh: I truly believe every person and every company has a problem, but it's up to that financial advisor to identif what the solution is for them to get them over that hump, if you will, and provide a meaningful solution that will benefit them in multiple ways.

Ashleigh: Our company, we've been around since 2007, and we are an insurance-based company.

Ashleigh: We deal with financial advisers that come to us. We deal with financial planners that come to us. We will we will work, if necessary, with the end consumer's CPA and estate planning attorney if that's what it takes.

Ashleigh: So we will get on the phone with everybody and make sure we figure out what the problems are, identify a solution, work that solution down to get it in their budget because everyone's got a budget and um make sure it works. You know, we will treat our clients as our family.

Dan: Love that. Love that. And our viewers know that uh my firm is called Tailored Wealth. So, I I promise I didn't put Ashley up to it, but I love the word tailored and and being customized to the unique situation, outcomes, and challenges that each client faces is uh is in in my opinion the best way to do this. So, I love that you said that.

Dan: All right. So, you mentioned a little bit about sort of like partners that you work with. Why don't you tell us a little bit about a how clients find you in the first place and then b if they come to you through some form of partner, what does that typically look like? What are the best types of uh referral partnerships for you?

Ashleigh: Absolutely. CPAs are fabulous referral partners for us because they know which clients have tax problems or which business clients of theirs are going to need some help on their end.

Ashleigh: So, I think CPAs are huge.

Ashleigh: Attorney firms attorney firms have and employ extremely lucrative employees. They do not want to lose those type of that type of worker to the small firm down the street with that's offering them maybe 50 grand more or 100 grand more in salary.

Ashleigh: So, there's a special program that we can put in place for an attorney's firm. Same thing for for medical medical firms. You know, there's a big um there's a big orthopedic company down here in Atlanta. that's where we're based out of. And that type of company would want to make sure that their orthopedists don't go somewhere else.

Ashleigh: How do you do that? How do you how do you keep them around through retirement and make sure that they stay with you and that they're happy and that they feel like they're being made whole? It's not all about what you can pay them, right? There's there's a lot more to it.

Ashleigh: So I would say CPAs, attorney firms, medical firms, estate planning attorneys are very important for us.

Ashleigh: You know, um estate planning attorneys have to have the life insurance embedded in their eyelets in order to make everything work. So those would be probably the the majority of the best partners as well as insurance advisors. I mean, we are a brokerage firm. We help financial and insurance advisors get the products that they're looking for, the case designs that they need and help them along the way in terms of the tax structure and how it will work with their clients.

Ashleigh: A lot of times these these insurance agents do need some help in that regard.

Dan: Yeah. Yeah. I I I've seen that and we've used others as well. So, you know, these these cases for for our audience from a client perspective can be fairly complex and having an expert that can help you to structure insurance solutions.

Dan: A lot of times when people hear insurance, they just think run-of-the-mill term life insurance, right? And, you know, that serves its purpose for for some folks, but it definitely sounds like your firm is playing in the space where it's higher ticket type clients that need shelter from an assets perspective and really need help on the tax side.

Dan: And that's where a higher level expertise like what your firm provides can be super, super valuable.

Ashleigh: Absolutely. Yeah. If you're looking for 25 to 50 million of life insurance coverage, you don't want to go to someone that doesn't know what they're talking about, right?

Ashleigh: You you wanting to go to someone that's going to understand the tax structure so that it can they can be structured appropriately to provide for when that estate eventually does get passed to the next beneficiary, it can work appropriately.

Dan: Got it. Got it. Okay, that's great.

Dan: So, you identified the key sort of partners that you work with. How do you typically collaborate with um with the partnerships that you have in your business, whether it be referral partners or just teams that you utilize to help you offer what you offer to your clientele?

Ashleigh: You know, everything has been meeting people directly or meeting people over the phone, doing three ways.

Ashleigh: We've we've done some type of I'll say collaborative referral programs where you know I have a mergers and acquisitions guy and he has a need for our services for his clients. When he's going through that process whether they're you know acquiring a new company or if they're going through an SBA loan they're going to need someone on this side to provide the insurance to make sure that these people are taken care of and have the necessary necessary protections in place.

Ashleigh: So I would say in that regard, we've done videos with with flyers out to them that that mergers is an acquisition or that estate planning attorney can send out to the client say, "Hey, this is what these people do and I'm referring them to you because they are articulate in it and can really help you." And that's been one way in which we've been able to make that connection.

Dan: Very cool. Very cool. Good to know. Good to know.

Dan: All right. Um, where do you see your industry going in the next 5 to 10 years? And uh how are you and your firm sort of staying on top of that?

Ashleigh: I like that question. So the industry and I think this is among many industries are trending towards this AI model.

Dan: AI never heard of it.

Ashleigh: Well, um same thing with insurance industry. They are able to review medical records faster, right? Instead of sitting there and physically reading a medical

Ashleigh: Excuse me just a second.

Dan: No worries. No worries.

Ashleigh: Instead of just sitting there.

Dan: Your phone's ringing. That's a good thing.

Ashleigh: Well, it's going on do not disturb. Okay.

Dan: All right. There you go.

Ashleigh: So, so in uh medical records can be reviewed a lot quicker than they were even a couple years ago with AI. We have insurance products that have instant approval. I mean, and when I say that, people have applied uh and been approved and got their policy in force on Christmas Day all in 15 minutes. Imagine that.

Ashleigh: Those those those old school like insurance veterans, imagine them hearing that now because uh that used to be a very lengthy process. I can speak from experience on that.

Dan: Yeah. I And just to give you an idea, I was on a a telephone call today with an insurance company that will autobind, meaning they can write it on their own own insurance paper.

Dan: They don't have to go out to reinsurance. Up to $170 million of death benefit on a life insurance policy. And all we have to have is if the if the client has seen a doctor in the last 12 months, the records and we don't even maybe need a medical exam.

Ashleigh: So there's a lot of things that the industry is doing to become quicker in their underwriting. There's a lot of things that the industry is doing to to make the process less honorous on the end consumer. And I think that's where we're going. I think you're going to see a lot more carriers do these instant approval style products. I think you're going to see as AI continues to evolve, things just getting snappier and snappier and snappier.

Dan: Yeah. I mean, that is so big for the insurance industry because that's an industry that's typically been very, very slow, right? So being able to apply and use machine learning and AI to add speed to the process. I mean I know we've seen it on our side how beneficial that is and I'm sure it's been super helpful for you and and there's more to come on that. Um hey that sounds great.

Dan: So let's uh let's shift gears a little bit and talk about Ashley. Tell us a little bit about your role and sort of your day-to-day responsibilities at the firm.

Ashleigh: Absolutely. As vice pres president of sales and marketing at Fortress Brokerage Solutions, I am doing the outbound marketing messages to clients on the end side as well as financial professionals.

Ashleigh: I'm kind of like the go-to person for financial professionals to say, "Hey, Ashley, I got a guy and I don't know what to do. You know, this is the circumstance. What would you recommend?"

Ashleigh: So, in that instance, you know, I'm the person that's talking product. I'm the person that's talking are they a business owner? are they not a business owner? What type of tax deductibility can we get here? I'm doing the case design on a day to day basis.

Ashleigh: So, if someone comes to me, they're going to be working with me directly. I do the case design in-house. It's it's me looking at it, making that tailored approach for that client, meeting whatever that goal in their problem is.

Dan: Very cool. Very cool. Sounds like a a fun job and one that's super important. It sounds like uh you know, a lot of uh a lot of day-to-day conversations with the right people. So, uh, as a as a former sales leader myself, I have a ton of appreciation, uh, for what you do.

Dan: Um, all right. So, what is the biggest challenge that you faced to this point in your life? And how do you think it's shaped the way that you do business?

Ashleigh: Yeah, you know, I think the biggest challenge is just getting the word out to people.

Ashleigh: We are doing that in a number of ways but we are having to do it in nuanced methods just like you and I are having this conversation here today. This would be in my mind a nuanced method. YouTube channel and in marketing in that manner is a method that we are using in house.

Ashleigh: So you know the the big issue with financial services is people don't know what they don't know. And if you don't know to reach out to somebody or you don't know that you have a problem at hand, how do you know do you know to articulate that to somebody?

Ashleigh: It really starts with a financial professional coming to that person and saying, "Hey, we need to sit down and we need to have a conversation until it's brought to their attention. They don't know they have an issue and they certainly don't know how to solve it."

Ashleigh: So from that perspective, I think education, education, education. The more we can educate the end consumer on what's going on in tax law, the more we can educate the consumer on what methods they have to be able to build their business better or protect their family or provide a larger legacy, the better we can do in the financial services industry.

Ashleigh: It's it's got to start from the professional down. We've got to educate the consumer. The consumer has to be willing to listen.

Ashleigh: You know, I do a lot of YouTube videos myself just to be able to put information out there on things like buyell agreements and keyman insurance. I get a lot of clients that call me up and they'll say, "My attorney says I need a key man policy, but really what they need is a buy sell agreement and a buy sell insurance program."

Ashleigh: So, it just depends. I think that the terminology is different for everybody, but if people can understand there are different ways to structure these programs, you just have to look to see what is my issue and how do I solve my issue? And if a financial professional can be the first person at the line to say, "Hey, I have a solution."

Ashleigh: That's the best way forward.

Dan: Yeah. Uh that's that's that's a lot of great stuff there. So, first off, I've been on YouTube for a few months now, so I can relate to that. And what we'll do is we'll get Ashley's YouTube channel and we'll put it in the show notes afterwards so everybody has access to that cuz I'm sure there's some some really good content there and probably some stuff that's hyper specific to the right individuals.

Dan: And I couldn't agree more with you around education. Um we've really used education and are using education as the foundation for our business. And you know what I find is to your point people don't know that they have an issue or a challenge until they talk to someone about that.

Dan: And by nature, personal finances, money, wealth is a super personal issue. So the types of services that your firm and my firm offers is hyperpersonal and uh in most cases, people aren't necessarily running out and searching openly for help in this regard most of the time.

Dan: So that's why I do believe that education is is so important. We're not selling a widget here, right? It's not just a simp I'm looking for this.

Dan: A lot of times it's I have this challenge and now I've got to find I'll use that word again that tailored solution that fits for myself, my business, my family, my needs, my goals, my life. And that's what uh what I think the right professionals in this space really help to do. And it sounds like your your firm is at the forefront of that. So uh so that's good.

Dan: Really, really good stuff.

Dan: All right, so now we're going to get to the fun part. Uh we're going to shift gears a little bit. We talked a bunch about business. We talked a bunch about your firm and what you do day-to-day.

Dan: We're getting into the lightning round, which uh I always enjoy this part of the conversation and everybody knows this that's listened to uh to our sessions in the past. We don't prep our guests on this. We don't give the questions ahead of time. So, this is going to be really really raw and organic.

Dan: So, Ashley, we're going to get into it.

Dan: It's very very simple. I'm going to ask you a question or give you a couple of options. You just blurt out the first thing that comes to your mind.

Dan: Okay? And feel free to give some explanation if you if you want. If not, you can keep it simple as well. We've got we got 10 questions here that we're going to work you through. So, let's get started.

Ashleigh: All right, let's do it.

Dan: Coffee or tea?

Ashleigh: Tea.

Dan: Okay. I'm a tea person myself. I got my tea right now. So, uh got my my

Ashleigh: Peppermint.

Dan: Okay. Peppermint tea. I like that. I like that.

Dan: Cats or dogs?

Ashleigh: Dog.

Dan: Okay. I'm a dog man as well.

Dan: What's one tool or piece of technology other than your computer or your phone that you can't live without?

Ashleigh: Ooh, think about that for a second. I would probably say my heart rate monitor at the gym.

Dan: Oh, love that. Love that. Okay, very cool. So, uh, we got a heart rate monitor at the gym. Very good.

Dan: Favorite quote or phrase about money or success.

Ashleigh: Ooh, I really like the quote that is, and I don't remember who said it. Oh, I think it was like Einstein or someone. Your money will make money which will make more money.

Dan: Yes. I love that. Yeah. I mean, Einstein is famous for the compounding effect, the eighth wonder of the world, right? Yep. So, that's right in that vein. I love it. I love it.

Dan: Favorite book on either finance or business.

Ashleigh: Rich Dad Poor Dad.

Dan: Oh, yeah. Classic. Classic. Love it.

Dan: Um, favorite personal finance hack.

Ashleigh: Oh, what is her name? I can see her face. I got to think about it for a second. She used to be on business. Fox Business. Ashley. I can't remember her name. So cute.

Dan: All right. Hack any hacks that you would re that that you use on the personal finance side that you would recommend to our audience.

Ashleigh: Hacks you mean like what do you mean by that?

Dan: Best practices, more efficient ways to do things, you know, just just just things that you can that you can as a financial professional that you would recommend to uh to our audience.

Ashleigh: I would say always start with a brokerage-based agent whether it's for car insurance, whether it's for life insurance. You don't want to go to a company that sells one product. You want to go to a company that says it spells a multitude of products so you can get the best deal.

Dan: You can apply that to a lot of different lines. So, I I love that one. That's a really good one.

Dan: What's one bucket list item you've already accomplished?

Ashleigh: Went to Hawaii.

Dan: All right. When did you do that?

Ashleigh: I did that for my honeymoon about six, seven years ago.

Dan: Very cool. Congratulations on that. That's great.

Dan: Uh, what's one financial milestone that you're still working towards?

Ashleigh: Becoming a millionaire.

Dan: Love it.

Dan: What's one financial mistake that you've seen turn into a valuable lesson either through yourself or or through others?

Ashleigh: I saw someone take a a loan against their 401k and it was a very big detriment to them.

Dan: Got it. Yep. You got to know your way around that for sure.

Ashleigh: Yeah.

Dan: Last one. If you could give one piece of money advice to your younger self, what would it be?

Ashleigh: H, if I could give one piece of money advice to my younger self, it would have been start saving younger.

Dan: Always a classic one. For those young people out there, listen to that one for sure.

Ashleigh: Those might be a lot. We've got to save something.

Dan: There you go. Sounds good. I love it. We're We're big fans of savers, that's for sure.

Dan: Um, all right. And finally, Ashley, uh, for our listeners that want to connect with you or to Fortress, collaborate, work with you, get in touch with you, what's the best way to reach you? Are there any specific platforms that you recommend folks check you out on? And again, we'll put the stuff in the show notes, but feel free to share share as well.

Ashleigh: Absolutely. So, you can reach me either email or telephone. My telephone is 678-322-3045. Email address is ashley.white@fortressbrokerage.com. Ashley is a s l e i g h.

Ashleigh: Um, we'll give you our YouTube channel, Fortressbrokerage Solutions, and then our fortress brokerage.com.

Dan: Very cool. Very cool. And again, we'll put put all that in the show notes for folks that want to connect with Ashley and her team. But Ashley, thanks so much for sharing your time and insights with us today. This was a lot of fun. I'm sure our audience will take a lot away from this and uh you've certainly got a specific need that you help customers to solve for.

Dan: So, I enjoy learning about you and we appreciate you coming on to uh the Making Sense of Your Money podcast.

Ashleigh: Thanks, Dan. Appreciate it.

Dan: You bet. You bet. Everybody, uh thanks for joining us as always and uh come back for more on the Making Sense of Your Money podcast. Check us out on YouTube. Check us out on LinkedIn and uh have a great rest of your day.

• Fortress Brokerage Solutions: Ashleigh’s firm, specializing in advanced insurance and risk-management strategies for tax, estate, and executive-benefit planning.
• Life insurance & estate planning: Often used within trusts or other structures to provide liquidity for estate tax and legacy goals; typically coordinated with estate attorneys and tax professionals.
• Non-qualified deferred compensation: Custom plans that allow executives to defer income and build supplemental retirement benefits beyond 401(k) limits.
• AI in underwriting: Many carriers now use automated systems to analyze medical data and speed up life insurance approvals, especially for higher face amounts.
• Tailored Wealth: Dan’s firm, which focuses on integrating tax, investment, and planning strategies for business owners and high-earning professionals.

• Tailored Wealth – Work with Dan and the team
• Making Sense of Your Money – Podcast Archive
• Resources for Business Owners & Professionals
• Contact Tailored Wealth

If you’re a high earner, business owner, or executive and this episode resonated, consider:

• Audit your risks & tax exposure: With your advisor and CPA, list:

  • Potential estate taxes (federal and state)
  • Key people whose departure would seriously damage the business
  • Gaps between your current savings and the lifestyle you want in retirement


• Evaluate existing insurance: Review:

  • Current life and disability policies
  • Any buy-sell or “key man” coverage
  • How (or if) these are integrated with your estate and tax plan


• Talk about executive benefits: If you own or help run a firm, ask:

  • “Do we have a real retention strategy for our top people?”
  • “Are we doing enough for their long-term security?”


• Bring in specialists: Coordinate a meeting between:

  • Your financial advisor
  • Your CPA and estate attorney
  • An advanced insurance design firm like Fortress Brokerage Solutions

  to explore whether estate liquidity solutions, NQDC, or executive benefits make sense.



• Stay educated: Subscribe to:

  • Ashleigh’s Fortress Brokerage Solutions YouTube channel for advanced tax/insurance topics
  • Making Sense of Your Money for ongoing conversations at the intersection of tax, planning, and business ownership

Thoughtful planning today can turn potential tax and risk landmines into powerful tools for building, protecting, and transferring your wealth.