
Plain-English legal triage for families.
The gist
Olsen on Law Radio Show is a practical legal call-in program built around real estate, probate, estate planning, and family property problems. Attorney Tom Olson answers everyday questions in direct language, often steering callers toward simple paperwork, beneficiary designations, and clearer next steps.
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About Olsen on Law Radio Show
Olsen on Law Radio Show is a caller-driven legal program centered on everyday legal problems. Its strongest rhythm is practical triage. Attorney Tom Olson listens to a situation, separates the legal issue from the surrounding frustration, and explains what probably matters next. The recurring center of gravity is estate planning. Probate avoidance comes up again and again, especially through payable-on-death accounts, deeds, wills, trusts, beneficiary designations, and car-title questions after a parent dies. The show favors simple tools when they are enough. It also explains when a revocable living trust may be the better fit, such as for young children, out-of-state property, grandchildren, or beneficiaries who should not receive money outright. Real estate is the other major lane. Callers bring questions about closings, contracts, title problems, timeshares, leases, deposits, tenants, and property ownership language that changes what happens after death. The program also makes room for workers' compensation, umbrella insurance, Medicaid beds, free in-home care programs, nursing home costs, and disputes between neighbors or family members. The style is fast and plain. Legal vocabulary appears, but it is quickly translated into ordinary consequences: who signs, who gets paid, who needs a death certificate, who may have to open probate, and where a form must be filed. The show is not a courtroom drama. It is closer to a Saturday-morning legal help desk, with enough repetition to make key ideas stick. Tom Olson regularly reminds listeners that brief answers are not a substitute for full legal advice. That caution is part of the product. The episodes are best for people who need orientation before paying for deeper help, especially families dealing with aging parents, property transfers, or planning for incapacity. It also suits homeowners, landlords, tenants, and adult children trying to avoid preventable paperwork fights. The differentiating value is specificity without theatricality. The show turns intimidating legal categories into concrete household decisions.
Made for: This show is for people sorting through estate planning, probate, property, landlord-tenant, or elder-care questions. It especially fits families who want practical orientation before a formal legal consultation.
What sets it apart: The program stands out by turning live caller problems into concrete next steps, with repeated emphasis on forms, deeds, account designations, and probate consequences. Its advice stays practical and cautious rather than theoretical.
In their own words
Legal answers and advice regarding real estate, estate planning and family law. Reach Attorney Tom Olsen at the Olsen Law Group in Orlando at 407-423-5561 or [email protected].
As heard by us
Based on 6 episodes we listened to · September 2026
Tom Olson makes estate planning, property disputes and elder-care decisions easier to follow by working from callers' concrete legal problems.
Olsen on Law Radio Show turns live legal questions into practical decisions about property, inheritance and care. Tom Olson works through callers' immediate problems, from landlord-tenant disputes and troubled closings to powers of attorney and support for aging parents.
Why you'd press play
Tom Olson turns Saturday-morning legal calls into the paperwork checklist you wish families inherited.
Press play if you want
- plain-English answers before probate, powers of attorney, or beneficiary forms become family group-chat chaos
- real callers' landlord, workers' compensation, and estate questions instead of tidy law-school hypotheticals
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Episodes
- 1
Burger King class action, workers' compensation
Attorney Tom Olson introduces his live radio show offering free legal advice on various topics including a Burger King class action and workers' compensation.
Apr 13, 2026·39m·2 clips - 2
Live from Spring Fiesta in Orlando
Hidden gemTom Olson and Chris Merrill broadcast Olson on Law live from the Spring Fiesta at Lake Eola in downtown Orlando, with WDBO tent noise and people walking past.
Apr 13, 2026·35m·2 clips - 3
Dynasty trusts, death taxes amounts,
Attorney Tom Olson introduces his radio show offering free legal advice on estate planning, real estate, and senior care issues.
Apr 13, 2026·36m·2 clips - 4
POA surrogate vs agent, neighbor's yard full of junk, history of Olsen on Law Radio Show
Hidden gemTom Olson opens Olson on Law on WDBO with live legal advice, the show's 40th anniversary in 2026, and the 844-580-9326 call-in line.
Mar 29, 2026·37m·2 clips - 5
Umbrella insurance, timeshare deed, types of probate, evicting unknown tenants
Hidden gemAttorney Tom Olson introduces his live radio show offering free legal advice on various topics including umbrella insurance, timeshare deeds, probate, and evicting unknown tenants.
Mar 29, 2026·35m·2 clips - 6
When to use a revocable living trust, is a trust the best way to avoid probate
Attorney Tom Olson introduces his radio show offering free legal advice on estate planning topics including revocable living trusts and avoiding probate.
Mar 16, 2026·38m - 7
Avoid probate, when to use a living trust, the importance of a financial power of attorney
Hidden gemTom Olson and Chris Merrill use WDBO's Olson on Law to explain that a last will and testament does not avoid probate, even when it names children as beneficiaries.
Mar 9, 2026·38m·2 clips - 8
Avoid probate, free in-home care for seniors
Hidden gemTom Olson and Chris Merrill use caller questions to explain Florida Medicaid options for seniors, including “30 hours a week” of in-home care and nursing-home coverage.
Mar 9, 2026·35m·2 clips - 9
Olsen on Law Radio Show
Hidden gemTom Olson and Chris Merrill spend much of WDBO's "Olson on Law" taking live calls on real estate, probate, nursing homes, and powers of attorney.
Mar 9, 2026·36m·2 clips - 10
Trusts for children with alcohol or addiction issues
Attorney Tom Olson introduces his radio show and invites listeners to call in for free legal advice on various topics, including trusts for children with addiction issues.
Jan 26, 2026·36m - 11
Home inspections, dissolving a trust, funding a trust, timeshare probate
Jan 26, 2026·36m - 12
The law regarding trimming the roots and branches of your neighbor's tree. DNR vs Living Will
Jan 12, 2026·36m - 13
Living trusts, VA aid & attendance, adding child to deed, in-home care for seniors
Aug 25, 2025·37m - 14
Beware i-buyer contracts, all about living trusts, free in-home health care for seniors
Aug 11, 2025·40m - 15
Using "step-up" to avoid capital gains taxes, avoiding probate on real estate, getting rid of a timeshare, summary probate adminstation
Aug 4, 2025·40m - 16
Attorney Tom Olsen answers call-in legal questions
Jul 28, 2025·38m - 17
Attorney Tom Olsen answers call-in legal questions
Jul 28, 2025·40m - 18
Attorney Tom Olsen answers call-in legal questions
Jul 28, 2025·40m - 19
The moment Tom decided to be a lawyer, using a trust for spendthrift children or children with alcohol or addiction issues, free in-home care for seniors
Jul 28, 2025·38m - 20
10.5.24 - WDBO Topics On: suffering from litigation case, identity theft, landlord tenant, evictions, estate planning.
Oct 23, 2024·40m - 21
9.21.24 WDBO Topics On: neighbor's fence on your property, estate planning, driving a neighbor's car with their permission, transferring title, purchasing organs, out of state guardianship to sell property.
Oct 23, 2024·37m - 22
9.14.24 - WDBO Topics On: estate planning, purchased used boat and trailer, and probate.
Oct 23, 2024·37m - 23
9.7.24 - WDBO Topics On: construction liens, medicaid assistance, and probate.
Oct 23, 2024·37m - 24
9.7.24 - WFLA Topics On: estate planning, public works issue, and assisted living and medicaid.
Sep 14, 2024·38m - 25
8.24.24 - WFLA Topics On: Easements, medicaid asset protection, and real estate commission change
Sep 3, 2024·39m - 26
8.3.24 - WFLA Topics On: landlord tenant law, probate, estate planning, and enhanced life estate deed.
Aug 9, 2024·39m - 27
8.3.24 - WDBO Topics On: civil litigation, landlord tenant law, and evictions.
Aug 9, 2024·36m - 28
7.27.24 WFLA Topics On: estate planning, and homestead exemptions.
Aug 2, 2024·39m - 29
7.27.24 WDBO Topics On: homestead, estate planning, new roof and notice of commencement, trusts, real estate commissions, and laws on gifts.
Aug 2, 2024·37m - 30
7.13.24 - WDBO Topics On: probate, bankruptcy, contracts, new construction loans, suits for partitian, and estate planning.
Jul 17, 2024·37m - 31
6/22/24 - WFLA Topics On: trees across property lines, leases, title theft, medicaid and nursing homes.
Jun 26, 2024·39m - 32
5.11.24 - WFLA Topics On: estate planning, dissolving a corporation, landlord tenant, and suit for partition.
May 17, 2024·39m - 33
5.11.24 - WDBO Topics On: landlord tenant, trusts, and LLCs.
May 17, 2024·48m - 34
5.4.24 - WDBO Topics On: automobile insurance, accident when you're at fault, forced into assisted living home, estate planning, and not showing up for jury duty.
May 10, 2024·37m - 35
5.4.24 - WFLA Topics On: estate planning, medicaid and nursing homes.
May 8, 2024·40m - 36
4.27.24 WFLA Topics On: estate planning, homeowners associations, enhanced life estate deeds, and probate.
May 3, 2024·39m - 37
4.27.24 WDBO Topics On: employment law, sexual harassment, non compete agreements, mediators, and pregnancy accomodations.
May 3, 2024·37m - 38
4.6.24 WFLA - Topics On: Estate planning, landlord tenant law
Apr 10, 2024·32m - 39
3.23.24 - WFLA Topics On: medicaid and nursing homes, estate planning, and in home care for seniors.
Mar 27, 2024·39m - 40
3.23.24 - WDBO Topics On: IRA being a protected asset, probate and estate planning, medicaid and nursing homes, and squatters.
Mar 27, 2024·39m - 41
3.9.24 - WFLA Topics On: medicaid planning, personal injury, and pet disputes.
Mar 13, 2024·39m - 42
3.2.24 - WFLA Topics On: dashcams, car titles, and landlord tenant law.
Mar 5, 2024·39m - 43
3.2.24 - WDBO Topics On: landlord tenant law, property heirs act, rental agreements, selling a property with a lien, and title theft.
Attorney Tom Olson introduces his radio show and guest attorney Caleb Maggio, offering free legal advice on various topics including landlord tenant law, property heirs act, rental agreements, selling property with a lien, and title theft.
Mar 5, 2024·37m - 44
2.24.24 - WFLA Topics On: probate, trusts, estate planning, and ladybird deed and transfer on death deeds.
Feb 29, 2024·39m - 45
2.24.24 - WDBO Topics On: buyer says they don't need an inspection, buying a house with defects, accidents and personal injury, and mortgage escrow and probate.
Attorney Tom Olson introduces his live radio show offering free legal advice on real estate, personal injury, and probate topics.
Feb 29, 2024·39m - 46
2.17.24 - WFLA Topics On: estate planning, probate, and roof issues after having roof replaced.
Feb 22, 2024·29m - 47
2.17.24 - WDBO Topics On: estate planning, why do you need a living will, trusts, and probate.
Feb 22, 2024·38m - 48
2.3.24 - WDBO Topics On: probate, non-compete clause, estate planning, and foreclosures.
Feb 7, 2024·36m - 49
1.27.24 - WFLA Topics On: life estate deed vs enhanced life estate deed, contracts skewing towards company and not homeowner, three day right to cancel in contracts, and trusts and joining trusts together.
Attorney Tom Olson introduces a live legal advice radio show covering topics like life estate deeds, contract skews, and trusts.
Feb 1, 2024·39m - 50
1.27.24 - WDBO Topics On: estate planning, potential negligence of contractors, and probate.
Feb 1, 2024·37m