Risky Assets

Greyhawk Premier Insurance Solutions
  • 5.0 (5)
  • Entrepreneurship
  • Semiweekly

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. They talk about how insurance is a means to investing in the future, and a necessary tool to be wielded by business owners. Their goal in both the podcast and their work at Greyhawk Insurance is to educate people on what proper structure is for their insurance, to think creatively about risk, and to share their experience with business owners who care about doing insurance right. 

  1. 4d ago

    When Does Building a Business Become Addiction? - EP040

    Most people who build something will tell you the hard part is the work. It is not. The hard part is knowing what enough looks like, and almost nobody says that out loud. One version of drive looks like excellence. Another looks like addiction. From the inside, the two can feel identical. Charlie Deaver and Daniel Clarke spend a full episode sitting in that question: where ambition stops being healthy, what has kept one of them working harder than he probably should, the cost they have watched other founders pay without ever choosing it, the opportunities they turned down on purpose, and what is left of legacy once you look at it honestly. TIMESTAMPS0:00  Introduction0:43  The question nobody wants to answer3:37  When ambition turns into something else6:02  The verse that will not leave him alone9:03  What it costs at home17:36  You do not own any of it26:01  Nobody will remember your name33:28  Is a 9 to 5 actually safer? ABOUT RISKY ASSETS The Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance Subscribe so you never miss an episode. New episodes weekly. #RiskyAssets #Entrepreneurship #SmallBusiness #FounderStory #Leadership #faithandwork  #santaclarita  Charlie Deaver, Daniel Clarke, Risky Assets Podcast, Greyhawk Premier Insurance Solutions, entrepreneurship addiction, workaholism, work life balance, how much is enough, ambition vs greed, stewardship, faith and business, christian entrepreneur, christian business owner, legacy, building a legacy, serial entrepreneur, multiple businesses, staying focused in business, Alex Hormozi, shiny object syndrome, business owner burnout, neglecting family for work, success and money, time is your greatest asset, parable of the talents, entrepreneur mindset, founder psychology, 9 to 5 vs business ownership, risk of employment, reinvesting profit, company culture, small business owner, Santa Clarita, Valencia California

  2. Oct 14

    What 5 Years of Building Greyhawk Actually Cost - EP039

    Five years ago Greyhawk was an idea in a car on a golf trip. Two guys from the same agency who did not know each other all that well, and who knew exactly one thing for certain: their strengths covered each other's gaps. Today it is more than twenty people, a full studio, and a building they are in the process of buying. But in between all of that, it almost ended twice. On this anniversary episode Charlie Deaver and Daniel Clarke go back through all of it. The house Charlie sold to fund it. The year everything they had built was on the line. The staff who doubled down instead of walking out. And the way the Lord kept putting the next piece in front of them in seasons when the math did not work on its own. It is an honest look at what building something actually costs, and what the two of them would tell themselves five years ago if they could. TIMESTAMPS0:00  Intro0:38  Five years, and two near misses2:40  The car ride that started it9:28  Two people who barely knew each other17:21  What they thought it would be20:00  The year it almost ended30:27  The people who would not leave43:33  What the next five look like ABOUT RISKY ASSETS The Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance Subscribe so you never miss an episode. New episodes weekly. #RiskyAssets #Entrepreneurship #SmallBusiness #FounderStory #Leadership #FaithAndWork #Anniversary #SantaClarita Charlie Deaver, Daniel Clarke, Greyhawk Premier Insurance Solutions, Risky Assets Podcast, five year anniversary, business anniversary, entrepreneurship, small business owner, starting a business, business partnership, co founder relationship, insurance agency owner, independent insurance agency, agency growth, building a company culture, business failure and recovery, near bankruptcy, business lawsuit, hard lessons in business, faith and business, christian business owner, stewardship, parable of the talents, leadership, hiring and training salespeople, employee ownership, long term thinking, founder story, origin story, business reflection, Santa Clarita, Valencia California, entrepreneur podcast

  3. Sep 28

    California Homeowners Are Not Stuck on the FAIR Plan Anymore - EP038

    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 show up in California, what the FAIR Plan was originally built for and why it was never meant to carry this much of the state, and the two coverages people skip that cost the least and protect the most. One of those comes down to a question most homeowners have never been asked. Contact Us: https://www.greyhawkinsurance.com/contact/ TIMESTAMPS0:38  Where the market broke2:15  The last resort that became the only option6:38  Why the market is moving again11:44  Why carriers left13:18  The bill that looks like a mortgage payment16:18  The coverage that protects everything else22:21  The one nobody thinks they need29:31  Why they left where they came from ABOUT RISKY ASSETSThe Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance

  4. Sep 14

    Heath Net is Leaving California. What This Means For Your Group Health Benefits - EP037

    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 opinions of the hosts and is for general discussion only. It is not legal, tax, or financial advice, and nothing in it confirms coverage under any plan. Carrier decisions, effective dates, and plan availability can change and are governed by the carrier and the plan documents as issued. Talk to a licensed professional about your specific situation. Work With Us:https://greyhawkinsurance.useindio.com/sign-up/xcxL2I6nQQRRgEFMgxWF TIMESTAMPS0:56  What just happened1:52  Why a carrier walks away3:50  The clock you did not know was running5:46  The plan that was too good to last7:51  Who is next10:12  The options nobody shows you15:22  Acting like your own insurance company20:23  The conversation your broker should be having ABOUT RISKY ASSETSThe Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance Wesley Deaver, Health Net, Health Net exit California, Health Net leaving California, Risky Assets Podcast, Greyhawk Premier Insurance Solutions, employee benefits, group health insurance, small group health insurance California, large group health insurance, health insurance renewal, open enrollment, carrier exit, Cal Choice, Anthem, Kaiser, UnitedHealthcare, HMO, PPO, PEO, professional employer organization, composite rating, age banded rating, self funded health plan, level funded health plan, captive insurance, stop loss insurance, HSA, health savings account, high deductible health plan, employee benefits broker, benefits strategy, cost containment, California employers, small business benefits, HR leaders, Santa Clarita, Valencia California

  5. Sep 7

    Prepare Your Family for the Next Emergency Before It's Too Late - EP036 with Aaron Rose

    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 moment the system stops working and the moment it comes back, and most families have never built one. Aaron Rose starts with the rule of threes: you can survive three minutes without oxygen, three days without water, and three weeks without food. From there he gets into what has to already be in your house, how you reach the people you love when the phones are down, why counting on help arriving is a plan with a hole in it, and the one thing hardly anyone in California buys until it is too late. Aaron's channel  @DontForgetYourLunch35   is linked below. https://www.youtube.com/@DontForgetYourLunch35 TIMESTAMPS0:00  Introduction1:16  The 94 quake and the road to the fire service5:37  The rule of threes11:43  Why nobody wants to think about this14:01  When three days is not enough22:07  The insurance most people skip23:55  Reaching your family when the grid is down28:57  The help that is not coming34:44  The last car out of the neighborhood ABOUT THE GUESTAaron Rose is a firefighter and paramedic in Southern California with more than ten years in the fire service, eight of them as a paramedic. He started as an EMT on a 911 ambulance at 18, served in the Navy in aircrew rescue and trained at its survival school, and now runs the YouTube channel Don't Forget Your Lunch, where he builds compact survival kits and reviews gear so families can put together their own. ABOUT RISKY ASSETSThe Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance Follow so you never miss an episode. New episodes every Monday. #RiskyAssets #DisasterPreparedness #EmergencyPreparedness #Earthquake #Wildfire #Firefighter #California #insurance

  6. Aug 31

    He Stepped Away From His Business for a Year and It Ran Without Him - EP035 with Tim Kane

    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 leaving to take care of her, and left. He worked about one month that entire first year. The business kept running and it stayed profitable. Tim and Daniel get into how you build a team that can do that, why he put employees first and profitability third, and what nearly 900 hires taught him about work ethic.  TIMESTAMPS0:43  Meet Tim Kane1:27  Seven companies, a dozen swings10:27  What actually makes a salesperson25:11  What he put ahead of profit33:02  The year he was not there38:32  The California problem53:36  What he knows now ABOUT RISKY ASSETSThe Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance #RiskyAssets #Entrepreneurship #SmallBusiness #Leadership #SalesLeadership #WorkersComp #AmazonDSP #california

  7. Aug 24

    Scale Your Business The Right Way - EP034 with Joshua Driskell

    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 outlives the founders' names, hiring to your weaknesses, and the hardest skill for any owner: learning to say no and protect your time. Joshua Driskell: https://www.lagerlof.com/teams/joshua-r-driskell/Lagerlof, LLP: https://www.lagerlof.com/ TIMESTAMPS0:00  Meet Joshua and what Lagerlof does2:11  Selling a business the right way4:45  When family and business collide9:29  From Ohio to California23:36  Going solo and one lucky lunch31:58  Merging up: build a brand, not a name43:43  Leading a firm: one voice, the right team49:19  Why the right clients beat more clients56:31  The exit, giving back, and the long game ABOUT RISKY ASSETSThe Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance Subscribe so you never miss an episode. New episodes weekly. #RiskyAssets #Entrepreneurship #LawFirm #EstatePlanning #FamilyBusiness #ExitPlanning #SmallBusiness

  8. Aug 17

    California's Dual Wage Threshold Is Changing & What Contractors Need To Know - EP033

    On September 1, 2026, California is raising the workers comp dual wage thresholds for contractors again, and this one is a big jump. In this episode of the Risky Assets Podcast, Charlie and Daniel break down what the dual wage threshold actually is, why paying an employee more can end up costing you less, and how to plan for it before your renewal and your year end audit catch you off guard. If you run a construction business in California, this is the kind of change that can quietly cost you thousands, so we walk through the real math, the ten year trend, and exactly what to do about it. RESOURCESDual Wage rate sheet (PDF): https://drive.google.com/file/d/1nOEHc-Zob4opeUO_1QjPiVmSg4KFLl7Q/view?usp=drive_linkWCIRB dual wage (official): https://www.wcirb.com/products-and-services/classification-searchTalk to Greyhawk / onboard: https://greyhawkinsurance.useindio.com/sign-up/BAu9UDjo6U9SLPaSXrur TIMESTAMPS0:00  What you need to know about Dual Wage4:00  The math: pay your people, not the insurer10:35  A decade of rising thresholds12:45  Finding your break even point17:57  How Greyhawk can help ABOUT RISKY ASSETSThe Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. Every episode is an honest conversation with entrepreneurs about building businesses, taking smart risks, and protecting what you create. FOLLOW THE SHOWInstagram: @greyhawkinsurance #RiskyAssets #Greyhawk #WorkersComp #DualWage #Contractors #Construction #California #SmallBusiness

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Ratings & Reviews

5
out of 5
5 Ratings

About

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. They talk about how insurance is a means to investing in the future, and a necessary tool to be wielded by business owners. Their goal in both the podcast and their work at Greyhawk Insurance is to educate people on what proper structure is for their insurance, to think creatively about risk, and to share their experience with business owners who care about doing insurance right. 

Information

  • Creator
    Greyhawk Premier Insurance Solutions
  • Years Active
    2022 - 2026
  • Episodes
    39
  • Rating
    Explicit
  • Copyright
    © 2026 Greyhawk Premier Insurance Solutions
  • Show Website
    Risky Assets

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