Oct 26, 202637 min
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...
About this Podcast:
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.
Pitch Analysis
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Contact path
Verified email
Booking probability
30%
Guest openness
Selective
80/100
Required Score
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Signup to Generate a PitchQuestions about Risky Assets
What is Risky Assets 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.
What has Risky Assets covered recently?
Recent episodes include "When Does Building a Business Become Addiction? - EP040" (26 October 2026, 37 minutes), "What 5 Years of Building Greyhawk Actually Cost - EP039" (14 October 2026, 54 minutes), and "California Homeowners Are Not Stuck on the FAIR Plan Anymore - EP038" (28 September 2026, 35 minutes).
How often does Risky Assets publish?
Risky Assets publishes roughly weekly, with episodes averaging 43 minutes.
How hard is it to get booked on Risky Assets?
Booking probability for Risky Assets is 30%, and the host is rated Selective on guests. Risky Assets requires a Pod Score of 80 or higher. Risky Assets's contact route on record: verified email.
Who should pitch Risky Assets?
The strongest fits for Risky Assets are Insurance Agencies & Brokers. Risky Assets has a business audience.
About the host
Risky Assets is a business podcast.
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Recent episodes
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
- Oct 14, 202654 min
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...
- Sep 28, 202635 min
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...
- Sep 14, 202623 min
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...
- Sep 7, 202640 min
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...
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Episode #35
He Stepped Away From His Business for a Year and It Ran Without Him - EP035 with Tim Kane
Aug 31, 20261h 11mTim 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...
- Aug 24, 20261h 17m
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...
- Aug 17, 202621 min
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...
- Aug 10, 20261h 1m
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...
- Aug 5, 202629 min
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...
Episode #30
How Businesses Fall Apart, From the Man Who Investigates Them - EP030 with Chris Hamilton
Jul 27, 20261h 9mChris 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...
- Jul 20, 202652 min
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...
- Jul 17, 202619 min
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...
- Jul 7, 202646 min
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...
- Jun 29, 20261h 3m
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...
- Jun 22, 202649 min
You might be paying for insurance that will never actually pay you back. In this episode of the Risky Assets Podcast, Greyhawk founders Charlie Deaver and Daniel Clarke, joined by the Greyhawk team, break down material...
- Jun 22, 202619 min
Your carrier just changed the contracts, and one of the biggest changes hit where it hurts: benefits. Group health, 401k, life, dental, and more are no longer offered through the corporate plan, which leaves a lot of...
- Jun 15, 202635 min
Greyhawk founder Charlie Deaver sits down with Michael Ross, founder of Vision Forensic Engineering, a national firm that figures out why buildings fail and what really caused an insurance loss. Think CSI for claims...
- Jun 15, 202623 min
He spent nearly a decade selling alcohol across Los Angeles. Then he watched the industry change for good and made the jump into commercial insurance. In this comeback episode of the Risky Assets Podcast, host Charlie...
- Sep 18, 202546 minS0
<p>Edgar Corona is our VP of Personal Lines at Greyhawk. We discuss:</p><p><br>- Shifting from big-name employers (In-N-Out and State Farm), to Greyhawk<br>- Trusting your gut<br>- The importance of life insurance (at...
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