It’s a tale as old as time. Four male investment managers try to tell a woman that a product she’s interested in doesn’t exist. How does she know they’re wrong? She literally traded them when she worked at Goldman Sachs. That’s just one moment that inspired Wallis Tsai to start her own company, AboveBoard Financial. And today she’s here to give women over 40 a no-BS education on life insurance.
Is It Too Late to Get Life Insurance in Your 40s or 50s?
Short answer: no. Wallis is in her f-ties herself and is quick to point out that in the scheme of insurance, they’re still young. Her company, AboveBoard Financial, regularly works with clients well into their sixties and beyond.
Even women with significant health histories have options. Wallis mentioned clients who survived heart attacks and are now covered at rates lower than their workplace plans. She’s also gotten women with active cancer diagnoses covered through executive benefit plans, where coverage is offered without individual health underwriting, as long as you’re currently working full time.
The key is carrier selection. AboveBoard works with about 30 carriers. Even if most of them pass, you only need one yes.
Red Flags to Watch for When Choosing an Insurance Agent
Wallis’s first test is simple: ask reasonable questions and see what happens. A reasonable question might be what company they work for and which carriers they regularly sell policies for. If the answer is vague or doesn’t quite add up, that’s a problem.
She’s also seen agents represent themselves as independent when they’re actually incentivized to push one company’s products, earning two to three times the commission for doing so. Check the bottom of their website for disclosure information, and keep asking questions until you actually understand how they operate.
The second red flag is around health classes. When you’re shown a life insurance quote, always ask what health class it’s based on and why they think you’d qualify for that tier. Some agents will show everyone the best or second-best pricing tier regardless of health history, which sets you up for a nasty surprise when the actual underwriting comes back.
If you have anything notable in your health history, ask whether the agent has pre-cleared you with the underwriting department. Getting lured into a lengthy application process only to be offered much worse pricing — for reasons that were totally knowable in advance — is a common and avoidable trap.
What Insurance Companies Can See About Your Health History
When you apply for individual coverage, you’re authorizing the insurance company to look into your health history. In practice, they’ll pull a Milliman Telescript report, which is essentially a credit report for your prescription drug history. They’re looking to see whether what you’re telling them lines up with what they can easily verify. They may or may not pull your full medical records, but they do have the right to require anything in your history.
Wallis’s advice: represent yourself in the most favorable light, truthfully possible. A good agent will know which carriers are most likely to price your specific situation well.
Case in point: one of her clients had a typo in her medical records. The diagnosis code for hoarding disorder is one keystroke away from the code for generalized anxiety disorder. One carrier refused to budge even when the client’s therapist offered to write a letter. A different carrier looked at the full picture, recognized the obvious error, and offered coverage. You only need one yes.
📌 DON’T WANT TO TAKE NOTES? WE DID IT FOR YOU.
Grab the cheat sheet that covers everything from all three episodes with Wallis.
Term vs. Permanent Life Insurance: What’s the Difference?
Term insurance is temporary. You choose a length, say 20 or 30 years, and if you die during that period your beneficiaries receive the death benefit. If you outlive the term, the policy ends and nothing is paid out. Wallis says that’s not a failure. It means you lived, which was the whole point. Think of it like homeowners or auto insurance: you buy it hoping you never have to use it.
Permanent insurance is designed to last your entire life. Whole life is one type, but it’s just one flavor. Wallis’s analogy: if permanent insurance is ice cream, whole life is mint chocolate chip. Variable life might be strawberry. Universal life might be chocolate. Different flavors exist because different goals require different structures.
Some permanent policies have a fixed death benefit. Others let you allocate a portion of your premiums to something like the S&P 500, meaning your death benefit can grow over time. Many also have cash value, money the policyholder can access while still alive, which can help fund retirement or provide other living benefits.
Permanent insurance costs significantly more than term, on average six to ten times more. If your goal is purely to replace income in the event of an early death, term is almost certainly the right answer. If you’re looking at supplemental retirement savings, estate planning, or leaving something behind, permanent starts to make sense.
You may have heard the adage “buy term and invest the difference.” Wallis says it’s worth taking seriously, but it needs to be analyzed for each person’s specific situation.
The Term to Permanent Conversion Option Nobody Tells You About
Most term policies include the right to convert some or all of your coverage to permanent insurance without having to prove you’re still healthy. Wallis says this can be hugely valuable.
Here’s why it matters. Say you took out a 20-year term policy at 40, healthy and feeling good about your odds. At 59 you’re diagnosed with something serious. Your term is about to expire. Without a conversion option you may be uninsurable. With one, you can lock in permanent coverage regardless of your current health.
The catch: conversion options have expiration dates. And not all carriers let you convert to good products. Some only offer a limited, expensive option that healthy people would never voluntarily choose. So when you’re selecting a carrier for term coverage, it’s worth asking now what your conversion options will look like later.
Why Your Workplace Life Insurance Is Probably Not Your Best Deal — And What Happens If You Lose Your Job
This is perhaps the most universally applicable thing Wallis covered: the life insurance you get through work is almost certainly not as good as you think it is.
The two most common issues: the death benefit amount is often too small, and the premiums for any additional coverage you elect are higher than what you could get on the individual market. Wallis says she has seen workplace coverage actually be a good deal literally zero percent of the time.
Workplace life insurance pricing is typically age-banded, meaning as you get older your premiums increase. It feels affordable in your thirties and starts to hurt in your forties. By your fifties it can be a serious expense, and Wallis describes it as a hockey stick.
To give you a sense of how much better the individual market can be: AboveBoard has gotten clients who survived heart attacks covered at rates lower than their workplace plans.
And then there’s the portability problem. Most workplace life insurance cannot be taken with you if you leave or lose your job. The handful of plans that are portable are typically portable only under the worst possible terms. Very expensive, very limited.
The individual market locks in your rate at the time you apply. You won’t lose your coverage because you lost your job.
The Group Discount Hack That Can Save Executive Women 20-40%
If you’re a business owner or part of a management team at a smaller, more nimble company, there’s a strategy worth knowing about.
Many carriers will run programs where if you get even two colleagues at the same company to apply at the same time as you, you can unlock group discounts of 20 to 40%. Wallis notes this is especially impactful for disability insurance, where rates start to climb for women in their forties and fifties.
Some of her executive clients have even sponsored coverage for their assistants or analysts to unlock those savings. You give someone a meaningful benefit, and the discount makes the whole thing worthwhile for everyone.
And for women with significant health histories, executive benefit plans at smaller companies can sometimes offer coverage with no individual health underwriting at all. The only question is whether you’re currently working full time.
The One Thing Everyone Should Know About Life Insurance
I asked Wallis for the single most important takeaway, and she didn’t hesitate.
Think about the people in your life who depend on you. If you were hit by that proverbial bus tomorrow, would they be okay financially? Would they be in a very different situation than they are today?
If the answer is yes, or even maybe, that’s worth acting on. And if you did that analysis when your first child was born, it’s worth revisiting. Life changes. Coverage needs change. The goal is to keep coming back to that question every few years and making sure the answer is still yes.
Mentioned in this Episode
About Wallis Tsai
Wallis Tsai is a finance insider turned industry disruptor, bringing a quantitative, no-BS approach to insurance-based wealth planning and risk management. A former Goldman Sachs investment banker and hedge fund investor, she was part of an elite team managing a multi-billion-dollar portfolio, developing expertise in capital markets, tax-efficient investing, and financial regulation. Shocked by the misinformation in the insurance industry, she founded AboveBoard to provide transparent, analytically driven insurance solutions for affluent professionals, high-net-worth families, and fiduciary advisors.
Wallis has offered expert witness testimony in a federal class-action lawsuit and is a guest lecturer at Harvard Business School, teaching Harvard MBA students how to avoid bad insurance advice. With a reputation for cutting through industry jargon, she helps clients integrate insurance into sophisticated estate, tax, and investment strategies. A sought-after speaker and podcast guest, Wallis is the go-to expert for those seeking trustworthy, mathematically sound financial protection strategies.
Full Episode Transcript
Wallis Tsai: If my husband was the person who had booked a meeting with a finance professional, it was mind-blowing to me. How many finance professionals were willing to assume that I was an easy mark. I had one experience where a group of four male investment managers tried to assert to me that there was no such thing as a publicly traded real estate index. And like I had literally traded that index when I was at Goldman. So I had a really very entertaining few minutes kinda like asking some questions.
Jackie MacDougall: Oh my gosh.
Wallis: At first I was open to giving them the benefit of the doubt, right? That maybe there was a miscommunication, or maybe they hadn’t understood what I was asking for after, you know, like the fourth follow-up, it becomes real clear that, like, if they were playing with any level of integrity, they would’ve answered my question. And I said, “Oh, it’s really funny that you guys like don’t know about publicly traded real estate indices, ’cause I remember trading,” and I rattled off a few tickers, like, you know, when I was in a multi-strategy hedge at Goldman Sachs. Have you guys ever heard of any of those as investment managers?
Jackie: And it was like a very awkward moment. And then there was like, oh, oh yeah, Bob blah. Did you know? Did you know what she was asking? Oh no. I’m not sure, Mike. I didn’t quite understand, and it was clearly BS, right?
Jackie: Oh my gosh, that’s crazy.
Wallis: Absolutely. It was just so mind-blowing to me, and I was like, “Man, like you shouldn’t need that level of professional credentialization to be able to stand up and get, you know, reasonable answers to reasonable questions.”
Jackie MacDougall VO: If you’ve ever wondered why certain women want to work with other women — that story is a perfect example. I’m not hating, I’m just pointing out facts. If you’re a woman who appreciates being respected, believed, and advocated for, this — and all episodes — are for you.
