COMMISSION PLANNING
By CalBroker in conversation with Daniel Wexler
Article Experience Options: Click here to Listen or Click here to Watch the full interview
Daniel Wexler has spent more than three decades as an estate planning attorney and wealth strategist, helping business owners keep more of what they earn and pass it efficiently to their families. For over 35 years, he has channeled that approach into minimizing what goes to “the IRS and to courts and legal fees,” while co-authoring “Love, Money, Control” to guide owners through legal, tax, and succession planning tailored to their goals.
In a recent conversation, Wexler joined California Broker Magazine to unpack how health insurance brokers can structure commission exits, manage retirement income streams, and deploy estate and tax tools to safeguard their books of business.
Time Shapes Your Options
For health brokers eyeing an exit, Wexler boils it down to one key factor: time. “Time is something that we have only a finite amount of,” he notes. “The more time you have, the better off you are for planning purposes,” while rushing leaves you with “fewer options.”
He breaks retirement into three main “buckets”: social security, qualified plans like IRAs and 401(k)s, and sale proceeds. “Social security is one bucket…401 IRA qualified money is another bucket…proceeds from the sale of a business…is another bucket,” each with rules that demand coordination.
Qualified funds carry strict timing: you “can’t take it out before you’re 59 and a half without having a 10% penalty,” and by “72, you must begin your mandatory minimum distributions.” Sale proceeds must bridge those gaps smartly.
Cash Up Front or Stretched Out
Your residual “mailbox money” forms the core value of any health book. CalBroker Magazine’s Phil Calhoun outlines buyer options: lump sum, a couple payments, or multi-year revenue splits—each with tax ripple effects best addressed upfront.
A lump sum triggers “a taxable event in one year and all of the taxes are going to be due April 15 after the close of the sale,” potentially as ordinary income or capital gains based on structure. It slams you into one tax year with limited offsets.
Stretch it out while keeping your corporation alive, and Wexler sees real leverage: “If you’re going to continue to have income and you can continue to have expenses, you’ll lower the taxable income.” You keep deducting as before, easing the shift to retirement.
Entity and Pro Tax Help
S-corp or LLC users should maintain the entity through payouts to expense items during “this transitionary period while you’re receiving income from the sale.”
Wexler pulls no punches on DIY tax prep: “No offense to TurboTax or H&R Block,” but owners need “a tax professional who can help you identify the planning opportunities that can reduce your taxable income while increasing the benefits you receive from the money that is coming into the business.” Longtime brokers can keep this “unabated” post-sale.
Calhoun’s team kicks off with 15-minute calls to gauge your book, timeline, and aims, then connects you to Wexler or specialists as needed.
Time is your friend when you have it, and your enemy when you don’t
Trusts Block Probate Risk
“Anyone in this industry should have a trust,” Wexler asserts. Self-employed brokers with assets otherwise face “intestate succession” or “a probate proceeding.” A trust brings in “a successor trustee to take care of your loved ones” without court, where “court equals time and money.”
It’s “a process, not an event.” Outdated trusts from the “minor children” era don’t fit today’s “minor grandchildren” reality or succession needs. Mid-payout death? Payments flow smoothly: “It should be done through a trust,” typically with no tax hit.
Add durable powers of attorney and health directives to direct assets “to the people you want the way you want.”
LIRPs and Deferred Income
Wexler doesn’t sell insurance but drives its use: “I don’t sell life insurance, but I have caused a lot of life insurance to be purchased.” Profit sharing, 401(k)s, deferred comp, and LIRPs convert mailbox cash into tax-smart buckets.
LIRPs act like Roth IRAs without caps: after-tax dollars build “a tax free retirement investment account,” as “life insurance works exact same way” with “no limitations on your earnings or the amount of money you’re allowed to put into it.”
Sudden retirement? “Time is not your friend.” Plan over “a runway of five, seven, ten years,” and you unlock “proactive planning… that will really impact the quality of your retired life just from an income standpoint.”
Get Started with Wexler
Brokers tap Calhoun’s team for a quick 15-minute call with Phil or David, then get routed to Wexler or peers “that are appropriate for you.”
He offers referrals “up to two hours of free consultation” on estate plans: “I will consult with your referrals… and not charge them for my time,” quoting fees only if you proceed. Reach Phil Calhoun at California Broker to launch your commission protection and exit plan.
Daniel J. “Danny” Wexler is an accomplished attorney and counselor at law admitted to the California State Bar, with admissions before the California Supreme Court and the U.S. District Court for the Southern District of California. A graduate of USC Gould School of Law, he has built a distinguished career spanning law, wealth strategy, and financial advisory roles, specializing in estate planning, succession planning, asset protection, and tax strategy. He is the co-author of Love, Money, Control: Reinventing Estate Planning and For California Doctors: A Guide to Asset Protection, Tax and Estate Planning, and is a sought-after educator for financial professionals nationwide of California Broker Magazine.
Phil Calhoun also is a leader in coaching health insurance professionals. He is an active member of several insurance associations including the California Association of Health Insurance Professionals (CAHIP) and local chapters in Orange County, Los Angeles, San Diego, and Inland Empire Health Insurance Professionals.
