HeyJaredRisky Assets
What do you really know about insurance? Charlie Deaver and Daniel Clarke host Risky Assets, a podcast about insurance, financial strategy, entrepreneurship, and business management.
- Indexed episodes, last 90 days
- 13
- Latest publication
- Sep 28, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 7, 2026
Latest episodes
California Homeowners Are Not Stuck on the FAIR Plan Anymore - EP038 (opens the original)
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For a few years the answer for a lot of California homeowners was the FAIR Plan or nothing. Carriers stopped writing, premiums climbed, and people who had spent decades paying off a house found out their insurer was letting them go. That market has quietly started to move again, and most homeowners have no idea what is available to them now. Edgar Corona and Ashley Macedo, who run personal lines at Greyhawk Insurance, get into what actually changed, including the two carriers nobody expected to
Heath Net is Leaving California. What This Means For Your Group Health Benefits - EP037 (opens the original)
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If your company's health plan runs through Health Net, the clock is already running. The carrier is exiting the small group and large group market in California, and the notices have gone out. Wesley Deaver, who runs employee benefits at Greyhawk, walks through what actually happens next: how much runway you have, what losing a low-cost competitor tends to do to everyone else's pricing, and the handful of creative options most employers never get shown. This conversation reflects the personal op
Prepare Your Family for the Next Emergency Before It's Too Late - EP036 with Aaron Rose (opens the original)
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Everyone manages risk every day without calling it that. We put on a seatbelt. We buy homeowners and auto and life insurance. Then we skip the part where the tap stops running for a week and the phones go dark. After the 1994 Northridge earthquake the freeways were on the ground and the local water supply was contaminated for days. In 2021 the Texas grid came within minutes of a collapse that would have taken weeks or months to reverse. Preparedness is nothing more than the bridge between the mo
He Stepped Away From His Business for a Year and It Ran Without Him - EP035 with Tim Kane (opens the original)
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Tim Kane has held ownership positions in seven businesses and been part of roughly a dozen more, from one of the internet's earliest email marketing companies to a startup Apple bought in four months. But the story Daniel Clarke digs into here is the one most owners never manage. When Tim's wife was diagnosed with cancer, he walked into his Amazon delivery business, roughly 100 trucks and more than 100 employees, told the leadership team he had spent three and a half years training that he was l
Scale Your Business The Right Way - EP034 with Joshua Driskell (opens the original)
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Joshua Driskell went from a town of 1,200 people in rural Ohio to leading Lagerlof, a Pasadena law firm of more than 120 people that guides high net worth families through tax, estate, real estate, and the sale of the businesses they spent a lifetime building. In this episode of the Risky Assets Podcast, Charlie and Joshua get into the honest work behind that climb. They dig into why fair is not always equal in a family business, how to actually prepare a company for sale, building a brand that
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