Risky Assets

Hosted by Greyhawk Premier Insurance Solutions

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Aug 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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33 recent

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

July 20, 2026Episode 2951 min

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. Timestamps 0:00 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

July 17, 2026Episode 2818 min

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. TIMESTAMPS 0:00 The $1,000 head start 0:31 A newer style: two guys talking money 1:15 What the Trump account is, and the honest disclaimer 2:09 The seed money and the long term growth math 2:52 The restrictions and the Roth conversion at 18 3:29 How it compares to a 529 4:51 Employer contributions and the double tax benefit 6:05 The drawbacks and why it is so restrictive 7:28 Custodial IRA, UTMA, and the tax tradeoffs 8:31 Why they chose cash value life insurance for their own kids 9:58 The honest talk on life insurance and commissions 11:02 Where the Trump account fits best 11:17 Using it as an employee retention tool 12:15 Why turnover is a business killer 12:52 The complicated bonus strategies they avoid 14:20 Do you still need a 529? Doing both 15:21 Talk to a financial planner (link below) 15:54 Could this replace Social Security? 18:13 Final thoughts and how to reach out CONTACT US https://www.greyhawkinsurance.com/contact/ DISCLAIMER This 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 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 Hashtags #RiskyAssets #PersonalFinance #WealthBuilding #FinancialLiteracy #Investing #SmallBusiness #EmployeeBenefits #TaxPlanning #KidsSavings

July 13, 2026Episode 2731 min

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. TIMESTAMPS 0:00 Why a high salary can make a sales rep too comfortable 0:24 Welcome and meet Thomas Love 1:10 Ten years in the electrical lighting industry 2:37 Great people, why leaving was not easy 3:01 What made him want something different 3:56 The variability of income across market niches 6:03 Hearing about the consistency on the insurance side 6:30 How Thomas and Greyhawk got connected 7:28 The non rosy pitch: salary, then the grind 8:16 It is not just about the money in front of your face 9:39 Betting on yourself and steps back to go forward 10:40 What excited him beyond the paycheck 11:04 Growth as a person and getting uncomfortable 12:22 Always wanting to own a business 13:34 The path to buying ownership at Greyhawk 14:38 Harder than expected: the nuances nobody tells you 15:11 Why the insurance sales cycle is a year long 16:16 Doing it right versus selling it cheap 17:45 The stakes: why one mistake is a big deal 18:57 Why a sales rep should be a little hungry 19:38 The long term payoff: time, family, freedom 19:58 The freedom to sell to anyone and build real relationships 20:56 Being more than a broker: connecting people 22:09 AI as a learning and training tool 24:14 Five year goals and the road to ownership 27:00 Focus on what you know and niche down 29:41 Insurance is a real career, and it does not have to be grimy 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

July 7, 2026Episode 2645 min

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. Timestamps 0:00 The dream: a team that can thrive because of the business 0:19 Welcome and meet Andrew Maly 0:49 The path into medical device sales 3:00 Getting the job that was not a formality 4:00 Married young, paying dues, and changing perspective fast 9:00 How medical device reps actually get paid 10:20 Why it takes two to three years to get competent 13:40 Real income ranges, from intro rep to twenty year veteran 16:00 Why the money compressed: reimbursements and a race to the bottom 17:40 Five kids, a mortgage, and the math that changed everything 19:30 Talking to Dad: why start over after twelve years 20:50 From idea to launch in a matter of months 22:30 Launching Mainly Medical and specializing in upper extremity 25:00 Player coach versus building a business bigger than you 27:50 Rosy glasses versus the brutal side of entrepreneurship 29:00 Three months in with no revenue and staying the course 30:00 The 18 month rule: head down before you reevaluate 33:40 The three year problem and building a team 37:00 What a rep actually does inside the operating room 39:40 The income potential of going out on your own 40:00 What success looks like at 55 43:30 The big pro and the dirty side of med sales ABOUT THE GUEST Andrew 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 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

June 29, 2026Episode 251 hr 3 min

The 1% That Sells Your Home For 20% Higher - EP025 with Melissa Diaz

She went from nearly 20 years at Hot Dog on a Stick to building a multi-seven-figure home staging and interior design firm. In this episode of the Risky Assets Podcast, Charlie Deaver and Daniel Clarke sit down with Melissa Diaz, founder of Stunningly Staged Homes, to talk about building a real business out of a creative skill. Melissa breaks down the numbers most people never hear: staging can return 300- 500%, homes that are staged tend to sell roughly 80% faster and draw offers around 20% higher, and her listings have moved in about 29 days against a Los Angeles average closer to 55. Beyond the staging stats, this is a candid founder conversation about the slow climb, hiring your weaknesses, building a business that can run without you, pricing your worth, and the unglamorous, inventory-heavy reality behind a business that looks effortless from the outside. Chapters 00:00 The numbers behind home staging 00:22 A female founder breaking the mold 01:16 What Stunningly Staged Homes actually does 03:46 From Hot Dog on a Stick to her own firm 05:16 Three years before her first hire 06:13 Staging vs. interior design, and why they balance 08:01 Knowing when to let go and delegate 11:16 Can your business run without you for six months? 15:34 $250K to almost $5M: the slow climb 16:04 Why staging is so inventory-heavy 19:42 Why interior design is regulated in California 20:45 “I'll just ask ChatGPT”: why DIY usually fails 23:21 Being a female founder, and pricing your worth 28:13 The staging ROI: 300 to 500% 30:07 “Staging costs less than your first price reduction” 33:47 What staging a 2,000 sq ft home actually costs 37:13 Her biggest challenge, and Covid hitting 50:06 Team, ownership, and hiring for behavior 57:25 Grass isn't greener: the real cost of working for yourself ABOUT THE GUEST Melissa Diaz is the founder of Stunningly Staged Homes, a Santa Clarita based home staging and interior design firm serving Santa Clarita, Los Angeles, and the Valley. A former director of operations turned entrepreneur, she has grown the company to a team of 12, a 7,000 square foot warehouse, and hundreds of homes staged each year. 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. CONNECT: Stunningly Staged Homes: https://stunninglystagedhomes.com/ FOLLOW THE SHOW Instagram: @greyhawkinsurance