Risky Assets

About Risky 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. 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.

Publisher

Greyhawk Premier Insurance Solutions

Category

business · business

Language

en

Explicit

No

First episode

23 Aug 2022

Latest episode

26 Oct 2026

Latest episodes

40 episodes in the feed.

1. 

   26 Oct 2026

   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. TIMESTAMPS 0:00  Introduction 0:43  The question nobody wants to answer 3:37  When ambition turns into something else 6:02  The verse that will not leave him alone 9:03  What it costs at home 17:36  You do not own any of it 26:01  Nobody will remember your name 33:28  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 SHOW Instagram: @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. 

   14 Oct 2026

   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

3. 

   28 Sept 2026

   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

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

5 ratings

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Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.