Risky Assets

Greyhawk Premier Insurance Solutions
  • 5.0 (5)
  • Entrepreneurship
  • Updated 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. 2d ago

    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

  2. Aug 10

    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/ TIMESTAMPS0:00 How Charlie and Brett met1:40 Hot sauce challenge before golf4:25 From Indiana to a California law firm8:00 Fired for challenging his boss16:24 Scaling to 100, then downsizing to 2824:35 Charlie's tough love: exit or commit28:20 Cutting his team with AI34:27 Interest and fees he won't pass to clients42:00 Do lawyers really drive up insurance costs?55:50 Golf and M19 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

  3. Aug 5

    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. TIMESTAMPS0:00  The vote nobody expected0:24  Two financial nerds, everyday guys0:56  Why we're talking Fed1:50  Why they held, who voted to raise2:34  Locked in at 3 percent3:10  Home prices are softening3:36  Everyone bet on cuts. Wrong.4:00  Oil is driving inflation4:52  Sitting on more cash5:24  One income, kids, California6:25  Car prices meet high rates7:05  Commission beats salary now7:27  The 85k debt trap8:08  The business owner squeeze8:44  Healthcare costs roll downhill11:10  The AI spending bubble13:25  4 percent vs the 2 percent norm14:30  The real number since 202015:33  So why not just cut?16:16  Who really wants a crash17:13  Supply is the real problem19:46  A framer's rising costs20:23  Wildfire and property insurance21:46  Apartments are getting crushed23:09  The workers comp wage shock25:00  Blue collar wages squeezed27:07  The case for self insurance27:49  Control the controllable28:11  Education is your best defense 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 #Inflation #FederalReserve #InterestRates #Economy #PersonalFinance #SmallBusiness #California

  4. Jul 27

    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. TIMESTAMPS0:00   The pile of ash: what a forensic accountant walks into0:33   Meet Chris Hamilton2:35   Fires, fraud, and disasters: the work behind forensic accounting6:06   The FBI case: a 1 a.m. informant and a truck full of records13:09   Starting the firm and a partnership where everyone earns the same18:58   What actually breaks partnerships: too much money and not enough22:51   Ownership is who you are today, not who we hope you become24:07   Family, ministry, and work: priorities are on a wheel34:36   Turning down Congress, and the strength that became a weakness45:50   Leading a business like the church, and where fraud creeps in51:57   No bad decisions: the deal that nearly ended the firm1:05:38   Succession, California, and working for the love of the game ABOUT THE GUESTChris 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 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

  5. Jul 20

    How The Right CPA Helps You Grow - EP029 with Joel Peluffo

    Joel Peluffo came to Santa Clarita from Argentina at 16 chasing soccer, and ended up a partner at Hedman Partners, one of the most respected CPA firms in the valley. In this episode Charlie sits down with him for an honest talk about using the right CPA to actually grow a business, not just file taxes. They get into why a great firm says no to clients, why value beats volume, and why chasing a tax write off often costs you more than it saves. Whether you are an owner who wants better numbers or someone weighing a career, this one is worth your time. Timestamps0:00   Meet Joel Peluffo: from Argentina to Santa Clarita 2:52   Soccer, a full ride, and stumbling into accounting 5:55   Getting hurt, marrying young, and betting on a career 9:05   Thirteen years at Hedman and the road to partner 13:08   Why Hedman says no: choosing clients by value, not revenue 20:27   Culture, community, and beating burnout 22:50   Competing with the Big Four and the private equity rollup opportunity 35:25   The truck write off trap and smarter tax strategy 41:09   High W2 earners, shiny loopholes, and the IRS 45:00   Advice for the next CPA: purpose over a paycheck Contact Hedman Partners LLC Website: https://www.hedmanpartners.com/ Phone: (661) 287-6333 Toll Free: (888) 866-4195 Email: info@hpllp.com About Risky Assets The Risky Assets Podcast is produced by Greyhawk Premier Insurance Solutions. We sit down with founders, operators, and experts for honest conversations about building a career, taking smart risks, and the real work behind the wins. Subscribe so you never miss an episode. New episodes weekly. Disclaimer This episode and description are for general educational purposes only and are not tax, legal, or financial advice. Tax rules and treatment change and depend on your situation. Please consult a qualified CPA or attorney before making decisions. Hashtags #RiskyAssets #Entrepreneurship #CPA #Tax #SmallBusiness #Accounting #BusinessOwner #SantaClarita #Leadership

  6. Jul 17

    Trump Accounts Explained: A New Way to Build Wealth for Your Kids - EP028

    There is a new financial tool on the table, and it could change how parents build wealth for their kids and how employers reward their people. In this episode of the Risky Assets Podcast, Charlie and Wesley walk through what the accounts are, the seed money for newborns, and how the accounts compare to the options families already use, including 529 plans, custodial IRAs, UTMA accounts, and cash value life insurance. They get into the part that interests them most as business owners: employer contributions that can be tax deductible and a genuine retention tool, plus the restrictions that keep the money locked away for the kid. This is an honest, opinionated conversation, and both of them are quick to say it: they are insurance guys, not financial advisors. Nothing here is financial or tax advice. Think of it as a starting point, then talk to a professional about your own situation. They will connect you with theirs if you want to dig in. If you are a parent trying to give your kids a head start, or a business owner looking for a simple, meaningful benefit, this one is worth your time. TIMESTAMPS0:00  The $1,000 head start0:31  A newer style: two guys talking money1:15  What the Trump account is, and the honest disclaimer2:09  The seed money and the long term growth math2:52  The restrictions and the Roth conversion at 183:29  How it compares to a 5294:51  Employer contributions and the double tax benefit6:05  The drawbacks and why it is so restrictive7:28  Custodial IRA, UTMA, and the tax tradeoffs8:31  Why they chose cash value life insurance for their own kids9:58  The honest talk on life insurance and commissions11:02  Where the Trump account fits best11:17  Using it as an employee retention tool12:15  Why turnover is a business killer12:52  The complicated bonus strategies they avoid14:20  Do you still need a 529? Doing both15:21  Talk to a financial planner (link below)15:54  Could this replace Social Security?18:13  Final thoughts and how to reach out CONTACT UShttps://www.greyhawkinsurance.com/contact/ DISCLAIMERThis episode and description are for general educational purposes only and are not financial, tax, or legal advice. Account rules, contribution limits, and tax treatment change and depend on your situation. Please consult a qualified financial or tax professional before making decisions. 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 Hashtags#RiskyAssets #PersonalFinance #WealthBuilding #FinancialLiteracy #Investing #SmallBusiness #EmployeeBenefits #TaxPlanning #KidsSavings

  7. Jul 13

    Comfort Is Why Most Salespeople Fail - EP027 with Thomas Love

    Thomas Love spent ten years building a career in the electrical lighting industry, working his way from the field into outside sales. Then, with a fourth kid on the way, he walked away from a stable job and good people to bet on himself in a career most people never even consider: insurance. In this episode of the Risky Assets Podcast, Charlie and Thomas have an honest conversation about what that leap actually looks like. The pay cut up front, the teeth kicked in during year two, and why Charlie refuses to paint a rosy picture for anyone thinking about making the jump. They get into why a comfortable salary can quietly kill a salesperson, why doing the work right matters more than selling it cheap, and the path to real ownership for producers who put in the work. If you have ever wondered whether insurance is a viable career, or you are staring down a career change of your own, this one lays out the honest tradeoffs, the fear, and the upside from someone who is living it right now. TIMESTAMPS0:00  Why a high salary can make a sales rep too comfortable0:24  Welcome and meet Thomas Love1:10  Ten years in the electrical lighting industry2:37  Great people, why leaving was not easy3:01  What made him want something different3:56  The variability of income across market niches6:03  Hearing about the consistency on the insurance side6:30  How Thomas and Greyhawk got connected7:28  The non rosy pitch: salary, then the grind8:16  It is not just about the money in front of your face9:39  Betting on yourself and steps back to go forward10:40  What excited him beyond the paycheck11:04  Growth as a person and getting uncomfortable12:22  Always wanting to own a business13:34  The path to buying ownership at Greyhawk14:38  Harder than expected: the nuances nobody tells you15:11  Why the insurance sales cycle is a year long16:16  Doing it right versus selling it cheap17:45  The stakes: why one mistake is a big deal18:57  Why a sales rep should be a little hungry19:38  The long term payoff: time, family, freedom19:58  The freedom to sell to anyone and build real relationships20:56  Being more than a broker: connecting people22:09  AI as a learning and training tool24:14  Five year goals and the road to ownership27:00  Focus on what you know and niche down29:41  Insurance is a real career, and it does not have to be grimy 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

  8. Jul 7

    He Left a 12-Year Career to Bet on Himself - EP026 with Andrew Maly

    Andrew Maly spent twelve years building a career in orthopedic medical device sales, one of the most talked about paths for anyone leaving college and eyeing big money. Five kids and a mortgage later, he walked away from the stability of a W2 to start his own distributorship from zero. In this episode of the Risky Assets Podcast, Andrew sits down with Charlie to pull back the curtain on an industry most people never get to see. What medical device reps actually do inside the operating room, why it takes two to three years to become competent, how the money really works, and what pushed him to trade a proven paycheck for the risk and freedom of owning his own thing. If you have ever wondered whether to leave a good job to build something of your own, this one is full of the honest tradeoffs nobody posts about. The rosy glasses, the brutal downside, and the advice that kept Andrew from panicking three months in with no revenue on the board. This is a real conversation about betting on yourself with your eyes wide open. Timestamps0:00  The dream: a team that can thrive because of the business0:19  Welcome and meet Andrew Maly0:49  The path into medical device sales3:00  Getting the job that was not a formality4:00  Married young, paying dues, and changing perspective fast9:00  How medical device reps actually get paid10:20  Why it takes two to three years to get competent13:40  Real income ranges, from intro rep to twenty year veteran16:00  Why the money compressed: reimbursements and a race to the bottom17:40  Five kids, a mortgage, and the math that changed everything19:30  Talking to Dad: why start over after twelve years20:50  From idea to launch in a matter of months22:30  Launching Mainly Medical and specializing in upper extremity25:00  Player coach versus building a business bigger than you27:50  Rosy glasses versus the brutal side of entrepreneurship29:00  Three months in with no revenue and staying the course30:00  The 18 month rule: head down before you reevaluate33:40  The three year problem and building a team37:00  What a rep actually does inside the operating room39:40  The income potential of going out on your own40:00  What success looks like at 5543:30  The big pro and the dirty side of med sales ABOUT THE GUESTAndrew Maly is the founder of Maly Medical, an independent medical device distributorship serving surgeons across Los Angeles, Kern, Ventura, and Santa Barbara Counties. After twelve years in the industry, he launched his own company to build something bigger than himself and create opportunity for a future team. Visit Maly Medical: https://www.malymedical.com/ 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

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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
    32
  • Rating
    Explicit
  • Copyright
    © 2026 Greyhawk Premier Insurance Solutions
  • Show Website
    Risky Assets

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