TMRW Insider https://www.tmrwbenefits.com Plain-English health insurance, broker economics, and the marketplace alternative — by Jesse Yoskowitz en-us © 2026 TMRW Benefits Mon, 31 Aug 2026 08:34:13 +0000 Jesse Yoskowitz Plain-English health insurance, broker economics, and the marketplace alternative — by Jesse Yoskowitz Jesse Yoskowitz jesse@tmrwbenefits.com false episodic The Free Care You're Probably Skipping (Preventive Benefits, Explained) The rare part of health insurance that's just good news — and the part most people leave sitting on the table. Jesse Yoskowitz and a benefits advisor explain the preventive care ACA-compliant plans cover at no cost-share when you're in-network: annual visits, screenings, vaccines, well-woman and well-child care, even before you've met your deductible. Plus the honest gotcha — how a "free" physical can quietly turn into a billed visit, and how to avoid it. Educational, not medical advice.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Mon, 31 Aug 2026 08:34:13 +0000 https://www.tmrwbenefits.com/podcast/preventive-care https://www.tmrwbenefits.com/podcast Jesse Yoskowitz The free care most people leave on the table. Jesse Yoskowitz and a benefits advisor on the preventive services ACA plans cover at no cost-share when in-network — annual visits, screenings, vaccines, well-woman and well-child care — plus the "free physical that turned into a bill" gotcha and how to avoid it. Educational, not medical advice. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:04:46 false full The rare part of health insurance that's just good news — and the part most people leave sitting on the table. Jesse Yoskowitz and a benefits advisor explain the preventive care ACA-compliant plans cover at no cost-share when you're in-network: annual visits, screenings, vaccines, well-woman and well-child care, even before you've met your deductible. Plus the honest gotcha — how a "free" physical can quietly turn into a billed visit, and how to avoid it. Educational, not medical advice.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Why Your Prescription Costs What It Costs (The Formulary, Explained) Why does the exact same pill cost one person five dollars and another two hundred? Jesse Yoskowitz and a benefits advisor pull the formulary — your plan's list of covered drugs — into the light. Plain-English on drug tiers (generics on the bottom, specialty on top where you pay a percentage, not a copay), prior authorization and step therapy, and the levers that can lower cost. Above all: check the formulary for your exact medications before you pick a plan. Educational, not medical advice.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Tue, 25 Aug 2026 05:16:00 +0000 https://www.tmrwbenefits.com/podcast/prescription-costs https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Why the same drug costs wildly different amounts across plans. Jesse Yoskowitz and a benefits advisor explain the formulary and its drug tiers, prior authorization and step therapy, and the levers that can lower cost — plus why you should check the formulary for your exact medications before picking a plan. Educational, not medical advice. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:05:12 false full Why does the exact same pill cost one person five dollars and another two hundred? Jesse Yoskowitz and a benefits advisor pull the formulary — your plan's list of covered drugs — into the light. Plain-English on drug tiers (generics on the bottom, specialty on top where you pay a percentage, not a copay), prior authorization and step therapy, and the levers that can lower cost. Above all: check the formulary for your exact medications before you pick a plan. Educational, not medical advice.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Open Enrollment vs Special Enrollment: The Deadlines That Lock You In (or Out) There are deadlines in health insurance that can quietly lock you out for a whole year — and almost nobody understands them until they're on the wrong side of one. Jesse Yoskowitz and a benefits advisor explain the two windows in plain English: open enrollment (the once-a-year door, roughly November to mid-January) and the Special Enrollment Period (the ~60-day key unlocked by a life event like losing coverage, moving, marriage, or a new baby). Plus what to do if you think you missed your window — you may have a key you didn't know about.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Tue, 28 Jul 2026 08:50:17 +0000 https://www.tmrwbenefits.com/podcast/open-enrollment-explained https://www.tmrwbenefits.com/podcast Jesse Yoskowitz The timing words. Jesse Yoskowitz and a benefits advisor explain the two windows that decide when you can buy coverage: open enrollment (roughly Nov to mid-Jan) and the Special Enrollment Period (about 60 days, unlocked by a life event). Plus what to do if you think you missed your window. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:05:22 false full There are deadlines in health insurance that can quietly lock you out for a whole year — and almost nobody understands them until they're on the wrong side of one. Jesse Yoskowitz and a benefits advisor explain the two windows in plain English: open enrollment (the once-a-year door, roughly November to mid-January) and the Special Enrollment Period (the ~60-day key unlocked by a life event like losing coverage, moving, marriage, or a new baby). Plus what to do if you think you missed your window — you may have a key you didn't know about.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> PPO, HMO, EPO: The Words That Decide Which Doctors You Can See The sequel to our plan decoder. Last time it was the money words — this time it's the network words, and they decide something money can't: which doctors you're actually allowed to see. Jesse Yoskowitz and a benefits advisor explain what a network really is, then HMO, PPO, EPO and POS in plain English — including why "PPO" isn't better, just more flexible, and why you should start from your doctors instead of the acronym.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Tue, 21 Jul 2026 12:32:32 +0000 https://www.tmrwbenefits.com/podcast/ppo-hmo-epo https://www.tmrwbenefits.com/podcast Jesse Yoskowitz The network words that decide which doctors you can see. Jesse Yoskowitz and a benefits advisor explain what a network really is, then HMO, PPO, EPO and POS in plain English — including why "PPO" isn't better, just more flexible, and why you should start from your doctors instead of the acronym. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:06:16 false full The sequel to our plan decoder. Last time it was the money words — this time it's the network words, and they decide something money can't: which doctors you're actually allowed to see. Jesse Yoskowitz and a benefits advisor explain what a network really is, then HMO, PPO, EPO and POS in plain English — including why "PPO" isn't better, just more flexible, and why you should start from your doctors instead of the acronym.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> How to Actually Read a Health Plan Health plans are written in a language nobody teaches you — but five words decide what you actually pay. Jesse Yoskowitz and a benefits advisor translate all five in plain English: premium, deductible, copay, coinsurance, and the one almost nobody checks, the out-of-pocket maximum. Learn these and you can read any plan in the country.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Tue, 14 Jul 2026 15:44:55 +0000 https://www.tmrwbenefits.com/podcast/how-to-read-a-health-plan https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Health plans are written in a language nobody teaches you — but five words decide what you pay. Jesse Yoskowitz and a benefits advisor translate all five in plain English: premium, deductible, copay, coinsurance, and the one almost nobody checks — the out-of-pocket maximum. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:05:59 false full Health plans are written in a language nobody teaches you — but five words decide what you actually pay. Jesse Yoskowitz and a benefits advisor translate all five in plain English: premium, deductible, copay, coinsurance, and the one almost nobody checks, the out-of-pocket maximum. Learn these and you can read any plan in the country.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Your Coverage Independence Day Happy Fourth of July. Since independence is literally what TMRW does, Jesse Yoskowitz and a benefits advisor riff on what it means to declare independence from a health plan that doesn't fit — the three freedoms most people never claim: the freedom to choose from the whole market, freedom from the autopilot renewal, and freedom from a one-size-fits-all plan. Honest note: independent doesn't mean cheaper, it means the right fit, on purpose.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Sat, 04 Jul 2026 09:00:00 +0000 https://www.tmrwbenefits.com/podcast/coverage-independence-day https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Happy Fourth of July. Jesse Yoskowitz and a benefits advisor on declaring independence from a health plan that doesn't fit — the three freedoms most people never claim: the freedom to choose the whole market, freedom from the autopilot renewal, and freedom from a one-size-fits-all plan. Independent doesn't mean cheaper; it means the right fit, on purpose. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:04:43 false full Happy Fourth of July. Since independence is literally what TMRW does, Jesse Yoskowitz and a benefits advisor riff on what it means to declare independence from a health plan that doesn't fit — the three freedoms most people never claim: the freedom to choose from the whole market, freedom from the autopilot renewal, and freedom from a one-size-fits-all plan. Honest note: independent doesn't mean cheaper, it means the right fit, on purpose.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Why Top Agents Are Leaving the Marketplace A different kind of episode — this one's for the agents and brokers. Jesse Yoskowitz talks with a broker who left the Healthcare.gov grind: why the marketplace keeps agents on a treadmill (little to no commission per enrollment, churn, starting from zero every January), and what the independent, off-exchange model looks like instead — recurring commission and a book of business you actually own. Honest about the trade-offs, no income promises.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Mon, 29 Jun 2026 05:36:01 +0000 https://www.tmrwbenefits.com/podcast/leaving-the-marketplace https://www.tmrwbenefits.com/podcast Jesse Yoskowitz For the agents and brokers. Jesse Yoskowitz talks with a broker who left the Healthcare.gov grind about why the marketplace keeps agents on a treadmill, and what the independent off-exchange model looks like instead: recurring commission and a book of business you own. Honest about the trade-offs, no income promises. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:05:05 false full A different kind of episode — this one's for the agents and brokers. Jesse Yoskowitz talks with a broker who left the Healthcare.gov grind: why the marketplace keeps agents on a treadmill (little to no commission per enrollment, churn, starting from zero every January), and what the independent, off-exchange model looks like instead — recurring commission and a book of business you actually own. Honest about the trade-offs, no income promises.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Your HSA Is Secretly a Retirement Account The most powerful account in health insurance that almost nobody uses right. Jesse Yoskowitz and a financial planner break down the HSA — the only account with a triple tax advantage, why it's secretly a retirement account, and the high-deductible catch that makes it brilliant for some people and a trap for others. (Plus a heated, unresolved debate about whether a hot dog is a sandwich.)

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Fri, 26 Jun 2026 15:14:05 +0000 https://www.tmrwbenefits.com/podcast/hsa-secret-retirement-account https://www.tmrwbenefits.com/podcast Jesse Yoskowitz The most powerful account in health insurance that almost nobody uses right. Jesse Yoskowitz and a financial planner break down the HSA — the triple tax advantage, why it's secretly a retirement account, and the high-deductible catch that makes it brilliant for some and a trap for others. Plus a heated, unresolved debate about whether a hot dog is a sandwich. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:06:38 false full The most powerful account in health insurance that almost nobody uses right. Jesse Yoskowitz and a financial planner break down the HSA — the only account with a triple tax advantage, why it's secretly a retirement account, and the high-deductible catch that makes it brilliant for some people and a trap for others. (Plus a heated, unresolved debate about whether a hot dog is a sandwich.)

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Losing Your Coverage? COBRA vs. the Marketplace You just lost your job, and a COBRA letter shows up with a price tag that makes your stomach drop. Now what? Jesse Yoskowitz and a benefits advisor break down COBRA versus the marketplace — when COBRA's continuity is worth keeping, how losing coverage can open a subsidy you didn't qualify for before, and the 60-day clock you can't afford to miss.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Sun, 14 Jun 2026 07:50:00 +0000 https://www.tmrwbenefits.com/podcast/cobra-vs-marketplace https://www.tmrwbenefits.com/podcast Jesse Yoskowitz You just lost your job, and a COBRA letter shows up with a number that makes your stomach drop. Jesse Yoskowitz and a benefits advisor break down COBRA versus the marketplace — when COBRA's continuity is worth keeping, how losing coverage can open a subsidy you didn't qualify for before, and the 60-day clock you can't miss. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:06:29 false full You just lost your job, and a COBRA letter shows up with a price tag that makes your stomach drop. Now what? Jesse Yoskowitz and a benefits advisor break down COBRA versus the marketplace — when COBRA's continuity is worth keeping, how losing coverage can open a subsidy you didn't qualify for before, and the 60-day clock you can't afford to miss.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> ICHRA Explained: Funding Coverage Without a Group Plan Four letters more business owners are hearing and almost nobody can define: ICHRA. Jesse Yoskowitz sits down with a benefits consultant to explain it in plain English — how an employer can give employees tax-free money to buy their own individual coverage, who it actually fits, and the trade-offs (including the subsidy catch) to run before you switch.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Thu, 04 Jun 2026 18:24:33 +0000 https://www.tmrwbenefits.com/podcast/ichra-explained https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Four letters more business owners are hearing and almost nobody can define: ICHRA. Jesse Yoskowitz and a benefits consultant explain it in plain English — how an employer can give employees tax-free money to buy their own individual coverage, who it fits, and the trade-offs to run before you switch. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:06:57 false full Four letters more business owners are hearing and almost nobody can define: ICHRA. Jesse Yoskowitz sits down with a benefits consultant to explain it in plain English — how an employer can give employees tax-free money to buy their own individual coverage, who it actually fits, and the trade-offs (including the subsidy catch) to run before you switch.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Why Your Benefits Broker Might Not Be On Your Side Jesse Yoskowitz sits down with a fellow benefits broker to pull back the curtain on how brokers actually get paid — commissions, the bonuses you can't see, and the 2021 federal rule that puts the full picture in writing. Plus the four questions to ask before your next renewal.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Mon, 01 Jun 2026 15:05:44 +0000 https://www.tmrwbenefits.com/podcast/broker-on-your-side https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Jesse Yoskowitz sits down with a fellow benefits broker on how brokers actually get paid — commissions, hidden bonuses, the 2021 disclosure rule, and the four questions to ask before your next renewal. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:05:03 false full Jesse Yoskowitz sits down with a fellow benefits broker to pull back the curtain on how brokers actually get paid — commissions, the bonuses you can't see, and the 2021 federal rule that puts the full picture in writing. Plus the four questions to ask before your next renewal.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Why "Free" Isn't Always Cheaper: Marketplace vs. Independent Insurance Is the government marketplace really the cheapest place to buy health insurance? Jesse Yoskowitz sits down with a financial advisor to bust the myth — when Healthcare.gov wins, when it doesn't, and why an independent broker who shops the whole market (on the exchange and off) can surface options the marketplace never shows you.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Wed, 13 May 2026 13:00:00 +0000 https://www.tmrwbenefits.com/podcast/marketplace-vs-independent https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Is the marketplace really the cheapest place to buy health insurance? Jesse Yoskowitz and a financial advisor bust the myth — when Healthcare.gov wins, when it doesn't, and why an independent broker who shops the whole market can surface options the marketplace never shows. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:08:54 false full Is the government marketplace really the cheapest place to buy health insurance? Jesse Yoskowitz sits down with a financial advisor to bust the myth — when Healthcare.gov wins, when it doesn't, and why an independent broker who shops the whole market (on the exchange and off) can surface options the marketplace never shows you.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> The Coverage Mistakes That Cost Businesses Getting your company's health coverage wrong costs more than money — it costs people, trust, and time. Jesse Yoskowitz talks with an HR leader about the boring, fixable mistakes that quietly hurt businesses, and how an independent, hands-on approach catches them before they do damage.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

]]> Wed, 15 Apr 2026 13:00:00 +0000 https://www.tmrwbenefits.com/podcast/coverage-mistakes-cost-businesses https://www.tmrwbenefits.com/podcast Jesse Yoskowitz Getting your company's health coverage wrong costs more than money — it costs people, trust, and time. Jesse Yoskowitz and an HR leader on the boring, fixable mistakes that quietly hurt businesses, and how an independent, hands-on approach catches them early. Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits. 00:07:38 false full Getting your company's health coverage wrong costs more than money — it costs people, trust, and time. Jesse Yoskowitz talks with an HR leader about the boring, fixable mistakes that quietly hurt businesses, and how an independent, hands-on approach catches them before they do damage.

Hosted by Jesse Yoskowitz, Founder and Principal Broker at TMRW Benefits.

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