Risky Assets

Hosted by Greyhawk Premier Insurance Solutions

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Oct 2026

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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.

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38 recent

October 14, 2026Episode 3954 min

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. TIMESTAMPS 0:00 Intro 0:38 Five years, and two near misses 2:40 The car ride that started it 9:28 Two people who barely knew each other 17:21 What they thought it would be 20:00 The year it almost ended 30:27 The people who would not leave 43:33 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 SHOW Instagram: @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

September 28, 2026Episode 3835 min

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/ TIMESTAMPS 0:38 Where the market broke 2:15 The last resort that became the only option 6:38 Why the market is moving again 11:44 Why carriers left 13:18 The bill that looks like a mortgage payment 16:18 The coverage that protects everything else 22:21 The one nobody thinks they need 29:31 Why they left where they came from 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 SHOW Instagram: @greyhawkinsurance

September 14, 2026Episode 3723 min

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 TIMESTAMPS 0:56 What just happened 1:52 Why a carrier walks away 3:50 The clock you did not know was running 5:46 The plan that was too good to last 7:51 Who is next 10:12 The options nobody shows you 15:22 Acting like your own insurance company 20:23 The conversation your broker should be having 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 SHOW Instagram: @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

September 7, 2026Episode 3639 min

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 TIMESTAMPS 0:00 Introduction 1:16 The 94 quake and the road to the fire service 5:37 The rule of threes 11:43 Why nobody wants to think about this 14:01 When three days is not enough 22:07 The insurance most people skip 23:55 Reaching your family when the grid is down 28:57 The help that is not coming 34:44 The last car out of the neighborhood ABOUT THE GUEST Aaron 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 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 SHOW Instagram: @greyhawkinsurance Follow so you never miss an episode. New episodes every Monday. #RiskyAssets #DisasterPreparedness #EmergencyPreparedness #Earthquake #Wildfire #Firefighter #California #insurance

August 31, 2026Episode 351 hr 11 min

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. TIMESTAMPS 0:43 Meet Tim Kane 1:27 Seven companies, a dozen swings 10:27 What actually makes a salesperson 25:11 What he put ahead of profit 33:02 The year he was not there 38:32 The California problem 53:36 What he knows now 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 SHOW Instagram: @greyhawkinsurance #RiskyAssets #Entrepreneurship #SmallBusiness #Leadership #SalesLeadership #WorkersComp #AmazonDSP #california

August 24, 2026Episode 341 hr 17 min

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/ TIMESTAMPS 0:00 Meet Joshua and what Lagerlof does 2:11 Selling a business the right way 4:45 When family and business collide 9:29 From Ohio to California 23:36 Going solo and one lucky lunch 31:58 Merging up: build a brand, not a name 43:43 Leading a firm: one voice, the right team 49:19 Why the right clients beat more clients 56:31 The exit, giving back, and the long game 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 SHOW Instagram: @greyhawkinsurance Subscribe so you never miss an episode. New episodes weekly. #RiskyAssets #Entrepreneurship #LawFirm #EstatePlanning #FamilyBusiness #ExitPlanning #SmallBusiness

August 17, 2026Episode 3320 min

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. RESOURCES Dual Wage rate sheet (PDF): https://drive.google.com/file/d/1nOEHc-Zob4opeUO_1QjPiVmSg4KFLl7Q/view?usp=drive_link WCIRB dual wage (official): https://www.wcirb.com/products-and-services/classification-search Talk to Greyhawk / onboard: https://greyhawkinsurance.useindio.com/sign-up/BAu9UDjo6U9SLPaSXrur TIMESTAMPS 0:00 What you need to know about Dual Wage 4:00 The math: pay your people, not the insurer 10:35 A decade of rising thresholds 12:45 Finding your break even point 17:57 How Greyhawk can help 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 SHOW Instagram: @greyhawkinsurance #RiskyAssets #Greyhawk #WorkersComp #DualWage #Contractors #Construction #California #SmallBusiness

August 10, 2026Episode 321 hr 0 min

What Nobody Tells You About Owning A Law Firm - EP032 with Brett Sachs

Brett Sachs is a California personal injury attorney who built his own law firm from an apartment and 20 thousand dollars in savings, scaled it to nearly 100 employees, then made the hard call to rebuild it leaner, down to 28 people while doing more volume with AI. In this episode of the Risky Assets Podcast, Charlie and Brett open with a Hot Ones style hot sauce challenge, then get into betting on yourself, being comfortable being uncomfortable, and the mindset that carried him through the scariest stretches of ownership. They also go deep on the money behind the legal and insurance worlds, from the costs some firms quietly pass to clients to an honest, two sided look at insurance, litigation, and tort reform. MVP Accident Attorneys - Brett Sachs: https://www.brettsachs.attorney/ TIMESTAMPS 0:00 How Charlie and Brett met 1:40 Hot sauce challenge before golf 4:25 From Indiana to a California law firm 8:00 Fired for challenging his boss 16:24 Scaling to 100, then downsizing to 28 24:35 Charlie's tough love: exit or commit 28:20 Cutting his team with AI 34:27 Interest and fees he won't pass to clients 42:00 Do lawyers really drive up insurance costs? 55:50 Golf and M19 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 SHOW Instagram: @greyhawkinsurance

August 5, 2026Episode 3129 min

The Fed Held Interest Rates. Here's What It Means For You. - EP031 with Wesley Deaver

The Fed just held interest rates steady, and three members actually voted to raise them. So why does it feel like everyone is getting squeezed harder than ever? In this episode of the Risky Assets Podcast, Charlie and Wesley sit down as two self described financial nerds and everyday guys to break down what the decision means for real people, not Wall Street. TIMESTAMPS 0:00 The vote nobody expected 0:24 Two financial nerds, everyday guys 0:56 Why we're talking Fed 1:50 Why they held, who voted to raise 2:34 Locked in at 3 percent 3:10 Home prices are softening 3:36 Everyone bet on cuts. Wrong. 4:00 Oil is driving inflation 4:52 Sitting on more cash 5:24 One income, kids, California 6:25 Car prices meet high rates 7:05 Commission beats salary now 7:27 The 85k debt trap 8:08 The business owner squeeze 8:44 Healthcare costs roll downhill 11:10 The AI spending bubble 13:25 4 percent vs the 2 percent norm 14:30 The real number since 2020 15:33 So why not just cut? 16:16 Who really wants a crash 17:13 Supply is the real problem 19:46 A framer's rising costs 20:23 Wildfire and property insurance 21:46 Apartments are getting crushed 23:09 The workers comp wage shock 25:00 Blue collar wages squeezed 27:07 The case for self insurance 27:49 Control the controllable 28:11 Education is your best defense 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 SHOW Instagram: @greyhawkinsurance Subscribe so you never miss an episode. New episodes weekly. #RiskyAssets #Inflation #FederalReserve #InterestRates #Economy #PersonalFinance #SmallBusiness #California

July 27, 2026Episode 301 hr 9 min

How Businesses Fall Apart, From the Man Who Investigates Them - EP030 with Chris Hamilton

Chris Hamilton gets called when the money disappears. He is a forensic accountant, which means fires, fraud, and figuring out what a business was worth the minute before it burned. Charlie and Daniel sit down with him for the stories most accountants never get to tell, and the harder lessons from 32 years of building a firm. TIMESTAMPS 0:00 The pile of ash: what a forensic accountant walks into 0:33 Meet Chris Hamilton 2:35 Fires, fraud, and disasters: the work behind forensic accounting 6:06 The FBI case: a 1 a.m. informant and a truck full of records 13:09 Starting the firm and a partnership where everyone earns the same 18:58 What actually breaks partnerships: too much money and not enough 22:51 Ownership is who you are today, not who we hope you become 24:07 Family, ministry, and work: priorities are on a wheel 34:36 Turning down Congress, and the strength that became a weakness 45:50 Leading a business like the church, and where fraud creeps in 51:57 No bad decisions: the deal that nearly ended the firm 1:05:38 Succession, California, and working for the love of the game ABOUT THE GUEST Chris Hamilton is a CPA, certified fraud examiner, and certified valuation analyst who has spent his career in forensic accounting and complex civil litigation. He started his firm in 1994, teaches forensic accounting certification around the country, and has served as an elder at Grace Community Church for more than two decades. Connect with Chris Hamilton: https://arxisfinancial.com/about-us/chris-hamilton-cpa-cfe-cva/ 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 SHOW Instagram: @greyhawkinsurance

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