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.
Risky Assets
Claim This Podcastby Greyhawk Premier Insurance Solutions
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27 episodes
Updated Weekly
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Podcast Overview
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.
Language
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Publishing Since
8/23/2022
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Recent Episodes
July 13, 2026
Comfort Is Why Most Salespeople Fail - EP027 with Thomas Love
<p>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.</p><p>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.</p><p>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.</p><p>TIMESTAMPS<br>0:00 Why a high salary can make a sales rep too comfortable<br>0:24 Welcome and meet Thomas Love<br>1:10 Ten years in the electrical lighting industry<br>2:37 Great people, why leaving was not easy<br>3:01 What made him want something different<br>3:56 The variability of income across market niches<br>6:03 Hearing about the consistency on the insurance side<br>6:30 How Thomas and Greyhawk got connected<br>7:28 The non rosy pitch: salary, then the grind<br>8:16 It is not just about the money in front of your face<br>9:39 Betting on yourself and steps back to go forward<br>10:40 What excited him beyond the paycheck<br>11:04 Growth as a person and getting uncomfortable<br>12:22 Always wanting to own a business<br>13:34 The path to buying ownership at Greyhawk<br>14:38 Harder than expected: the nuances nobody tells you<br>15:11 Why the insurance sales cycle is a year long<br>16:16 Doing it right versus selling it cheap<br>17:45 The stakes: why one mistake is a big deal<br>18:57 Why a sales rep should be a little hungry<br>19:38 The long term payoff: time, family, freedom<br>19:58 The freedom to sell to anyone and build real relationships<br>20:56 Being more than a broker: connecting people<br>22:09 AI as a learning and training tool<br>24:14 Five year goals and the road to ownership<br>27:00 Focus on what you know and niche down<br>29:41 Insurance is a real career, and it does not have to be grimy</p><p>ABOUT RISKY ASSETS<br>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.</p><p>FOLLOW THE SHOW<br>Instagram: @greyhawkinsurance</p><p><br></p>
July 7, 2026
He Left a 12-Year Career to Bet on Himself - EP026 with Andrew Maly
<p>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.</p><p>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.</p><p>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.</p><p>This is a real conversation about betting on yourself with your eyes wide open.</p><p>Timestamps<br>0:00 The dream: a team that can thrive because of the business<br>0:19 Welcome and meet Andrew Maly<br>0:49 The path into medical device sales<br>3:00 Getting the job that was not a formality<br>4:00 Married young, paying dues, and changing perspective fast<br>9:00 How medical device reps actually get paid<br>10:20 Why it takes two to three years to get competent<br>13:40 Real income ranges, from intro rep to twenty year veteran<br>16:00 Why the money compressed: reimbursements and a race to the bottom<br>17:40 Five kids, a mortgage, and the math that changed everything<br>19:30 Talking to Dad: why start over after twelve years<br>20:50 From idea to launch in a matter of months<br>22:30 Launching Mainly Medical and specializing in upper extremity<br>25:00 Player coach versus building a business bigger than you<br>27:50 Rosy glasses versus the brutal side of entrepreneurship<br>29:00 Three months in with no revenue and staying the course<br>30:00 The 18 month rule: head down before you reevaluate<br>33:40 The three year problem and building a team<br>37:00 What a rep actually does inside the operating room<br>39:40 The income potential of going out on your own<br>40:00 What success looks like at 55<br>43:30 The big pro and the dirty side of med sales</p><p>ABOUT THE GUEST<br>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.</p><p>Visit Maly Medical: https://www.malymedical.com/</p><p>ABOUT RISKY ASSETS<br>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.</p><p>FOLLOW THE SHOW<br>Instagram: @greyhawkinsurance</p>
June 29, 2026
The 1% That Sells Your Home For 20% Higher - EP025 with Melissa Diaz
<p>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.</p><p>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.</p><p>Chapters<br>00:00 The numbers behind home staging<br>00:22 A female founder breaking the mold<br>01:16 What Stunningly Staged Homes actually does<br>03:46 From Hot Dog on a Stick to her own firm<br>05:16 Three years before her first hire<br>06:13 Staging vs. interior design, and why they balance<br>08:01 Knowing when to let go and delegate<br>11:16 Can your business run without you for six months?<br>15:34 $250K to almost $5M: the slow climb<br>16:04 Why staging is so inventory-heavy<br>19:42 Why interior design is regulated in California<br>20:45 “I'll just ask ChatGPT”: why DIY usually fails<br>23:21 Being a female founder, and pricing your worth<br>28:13 The staging ROI: 300 to 500%<br>30:07 “Staging costs less than your first price reduction”<br>33:47 What staging a 2,000 sq ft home actually costs<br>37:13 Her biggest challenge, and Covid hitting<br>50:06 Team, ownership, and hiring for behavior<br>57:25 Grass isn't greener: the real cost of working for yourself</p><p>ABOUT THE GUEST<br>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.</p><p>ABOUT RISKY ASSETS<br>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.</p><p>CONNECT:<br>Stunningly Staged Homes: https://stunninglystagedhomes.com/</p><p>FOLLOW THE SHOW<br>Instagram: @greyhawkinsurance</p>
27 total episodes available
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- What is Risky Assets?
- How often does this podcast release new episodes?
This podcast updates weekly.
- Where can I listen to this podcast?
This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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No, this podcast does not typically feature guests.
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