Wealth Expert Alan Porter: Why Founders Crush Business But LOSE in Wealth & The Hidden Playbook to Dominate Both
Are you winning in business, but quietly losing the wealth game?
If you are a founder generating strong revenue, building enterprise value, and planning for an eventual exit, this episode may be the wake-up call you did not know you needed.
Because crushing business and protecting wealth are not the same skill set.
And according to Wealth Expert Alan Porter, that disconnect is costing entrepreneurs millions.
The Trap No Founder Sees Coming
Alan Porter did not arrive at wealth strategy through theory alone. He is a former Black Hawk instructor pilot. A real estate professional who survived the 2008 crash. A father and grandfather shaped by devastating health crises inside his own family.
He has witnessed firsthand how fast financial security can unravel.
“Money magnifies whatever is unresolved,” Alan explains.
When success accelerates faster than strategy, emotional blind spots expand. Entrepreneurs pour everything into growth, scaling, hiring, and expanding. But behind the scenes, tax exposure builds. Retirement risk compounds. Long-term care planning is ignored.
The business grows.
The wealth erodes.
Porter doesn't mince words. He dives straight into the chaos that hits when life throws curveballs. "I was like 99% of the people out there that thought life insurance was a death product that you had to die to benefit from it," he admits, recounting a devastating family diagnosis that could have bankrupted everyone involved. But a hidden rider in a policy changed everything, unlocking hundreds of thousands in benefits during a crisis. This isn't just a story—it's a stark warning. Are you prepared for the unexpected health bombshell that could derail your empire overnight?
It Is Not What You Make
In the episode, Alan makes a statement that stops founders cold:
“It’s not how much money you make. It’s how much money you keep after taxes are paid.”
Simple. Brutal. True.
Too many entrepreneurs assume their accountant “has it handled.” But accountants are typically reactive. They record what happened. They file what is required. They do not proactively design advanced tax strategies unless specifically engaged to do so.
Alan and his team specialize in uncovering what founders do not know to ask.
In one case, a dentist who sold his practice for 8.3 million dollars was able to reclaim over 2 million dollars in past taxes through strategic planning.
Not gray area loopholes.
Black letter law.
Proper planning.
Second opinions.
The difference between writing a massive check to the government or reinvesting capital into your family’s future.
The Exit Tax Time Bomb
If you are planning to sell your business, here is the uncomfortable truth:
You cannot install tax strategy after the deal closes.
The planning must happen before liquidity.
Alan emphasizes that proactive structuring, entity optimization, and advanced tax positioning can often be implemented quickly. But they require awareness and early action.
Waiting until the wire hits your account is too late.
Entrepreneurs obsess over valuation multiples.
They rarely obsess over net proceeds.
That gap is where millions disappear.
The Silent Long Term Care Crisis
This part of the conversation hits hard.
Seventy percent of Americans will require long term care at some point in their lives.
Medicare does not cover it.
Medicaid requires spend down.
If you do not have proper protection in place at least five years before a qualifying event, the government can legally consume your assets before assistance applies.
Alan has watched families crumble under this weight.
He shares the reality of Alzheimer’s, dementia, and prolonged decline. Not as abstract statistics. As lived experience.
“Long term care will devastate families who are not prepared,” he says.
For founders who claim they are building legacy, this cannot be ignored.
The Retirement Risk Nobody Explains
Wall Street sells rate of return.
Alan focuses on distribution risk.
There is a difference.
If you begin retirement withdrawals during a market downturn, the sequence of returns risk can destroy your portfolio far faster than most models predict.
A four percent withdrawal rate is not safe in all conditions.
Fees compound.
Losses compound.
Taxes compound.
Retirement income is not about chasing higher returns.
It is about stabilizing distribution.
“If you lose money in the early years of retirement while taking withdrawals, you can be out of money by year five,” Alan warns.
For entrepreneurs who spent decades building liquidity, that risk is unacceptable.
Retirement? Most entrepreneurs treat it like a distant dream, but Porter calls it a potential disaster zone. "Do you realize 58% of the people out there don't even think there's a fee on the 401k, and the average fee in a 401k is 2.99%," he reveals. Add taxes of 20-55%, and you're left with scraps. He hammers home sequence of returns risk: Lose 10% early in distributions, and your million-dollar portfolio vanishes in years.
Porter's playbook? Diversify into buckets that guarantee income and shield from volatility. He hints at fixed indexed annuities turning $650,000 into lifelong $40,000 payouts—leaving $350,000 free for other moves. "If you have guaranteed income in retirement, you're gonna live a healthier, happier, longer life," he says, backed by Harvard studies. But ignore this, and market crashes like 2008 repeat, turning your nest egg into nothing. The message is clear: Conventional planning is propaganda—break free or pay the price.
Effective Interest Cost and Becoming Your Own Bank
One of the most eye-opening moments in the episode centers around effective interest cost.
Many founders celebrate low mortgage rates while unknowingly paying massive effective interest across credit structures.
Alan breaks down how 2.75 percent mortgages and high interest credit lines can quietly generate effective costs north of 40 percent when amortization and compounding are considered.
Then he introduces a controversial but powerful concept.
Becoming your own financial institution.
Using properly structured cash value life insurance policies, founders can access capital while allowing underlying assets to continue compounding.
The goal is not insurance as an “investment.”
It is insurance as a financial control system.
As Alan explains, “You can use up to ninety percent of your death benefit for long term care tax free.”
For entrepreneurs who value control, this reframes the conversation entirely.
The Long-Term Care Bomb No One Defuses
Health crises don't discriminate, and Porter's family ordeals prove it. "70% of all Americans are gonna need long-term care at some point in their life," he warns, detailing how Medicaid spend-downs confiscate assets if you're unprepared. A million-dollar portfolio? Gone to cover costs, leaving spouses destitute.
His solution teases genius: Leverage cash value life insurance for pennies on the dollar. "You can use up to 90% of that for long-term care tax free," Porter explains. It's not just protection—it's a multiplier, turning $100,000 cash value into $1 million benefits. Founders juggling family legacies can't afford to skip this. One client story hints at a 42-year-old's sudden death leaving kids unsupported—no insurance, total devastation. Act now, or watch your empire fund a crisis you never saw coming.
The Emotional Side of Wealth
Beyond tactics, this episode reveals something deeper.
Alan’s journey into wealth strategy was forged through tragedy. A daughter in law diagnosed with stage four pancreatic cancer. A son navigating disability. A daughter battling cancer and rare autoimmune conditions.
Wealth planning is not about spreadsheets.
It is about reducing stress before life changes everything.
“I never thought I would be doing this,” Alan admits.
But experience reshaped his mission.
Founders often believe optimism will carry them through.
Optimism without preparation is fragile.
The Second Opinion Advantage
Throughout the conversation, one theme repeats.
Second opinions matter.
Just as you would not schedule brain surgery without confirmation, you should not entrust generational wealth to a single viewpoint.
Alan is clear that he does not replace existing advisors.
He collaborates.
He supplements.
He challenges assumptions.
“What they do not know can cost you millions,” he states.
For high achievers who pride themselves on diligence, ignoring financial blind spots is inconsistent with how they operate in business.
Legacy Planning That Outlives You
Wealth isn't just for you—it's generational firepower. Porter slams estates like Don Shula's or Prince's, where no plans meant governments and attorneys feasted. "The government taxes you on what you own, not what you control," he emphasizes. Tease: Trusts and strategies that pass fortunes tax-free, self-completing for heirs.
He pushes education funding via insurance—beating 529 plans with no volatility, no penalties, and death benefits. "It's the best college funding vehicle available today. Bar none," Porter asserts. For businesses, preventative health programs cut costs by $1,200 per employee, boost retention 7%, and add revenue. It's holistic: Mitigate risks, educate relentlessly, and build teams of experts. Skip the solo act—collaborate or crumble.
The Bottom Line
If you are serious about exiting well.
If you care about your family’s future.
If you believe legacy means more than valuation.
You cannot afford to ignore the wealth game.
Business growth is only half the equation.
The real scoreboard is what remains.
Listen to this episode with Wealth Expert Alan Porter and challenge your assumptions. Then take action.
Because dominating business without dominating wealth is not victory.
Your future self and family demand it. Secure your edge before it's too late.
Subscribe to The Deep Wealth Podcast and make sure you never build success on unstable ground again.
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