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

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

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

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 misrepresentation: the quiet, common way a “cheaper” policy gets your claim denied when you need it most.
Through real cases, a custom-fabrication shop insured under the wrong coverage, a 120-property portfolio missing habitability coverage, and an industrial park misclassified as retail, the team shows how cheaper quotes are often cheaper because a broker misrepresented what you actually do. When that happens, the carrier can deny the claim or void the contract entirely, and suing the broker rarely makes you whole. Along the way you'll get plain-English breakdowns of co-insurance penalties, surplus lines, and why your policy is a legal contract you should actually read before you sign.

00:25 Do it right vs. do it wrong
01:41 A custom-fab client and a cheap policy that wasn't
03:13 What “material misrepresentation” really means
04:25 Why suing your broker won't save you
05:49 The apartment quote that was too good to be true
07:52 Lie about something small, you'll lie about something big
08:55 Co-insurance: the penalty for under-insuring
11:23 Brian Hauser: the 120-property habitability case
16:44 “I can't knowingly walk you into the lion's den”
19:38 Roger Romero: an industrial park misclassified as retail
22:30 Your insurance policy is a legal contract
25:24 When doing it right pays off (the fire claim)
26:11 Eddie: the lie that scares him for the industry
28:45 Nobody reads what they sign
32:30 A hard market reveals who's swimming naked
38:44 Jesse: the bus account and hidden operations
43:15 The panel problem, and a workaround that saves clients money
48:04 Want Greyhawk to review your policy?

FOLLOW THE SHOW
Instagram: @risky.assets
Greyhawk Instagram: @greyhawkinsurance

#RiskyAssets #Greyhawk #Insurance #CommercialInsurance #SmallBusiness #RiskManagement #Entrepreneurship

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 captive agency owners scrambling to cover themselves and their teams. In this episode of the Risky Assets Podcast, Greyhawk founders Charlie Deaver and Daniel Clarke, a former captive agency owner, break down exactly what changed and what agents can actually do about it.

Greyhawk is launching an exclusive nationwide benefits program through BBSI, a professional employer organization (PEO), that lets affected agents jump back into large group rates, keep strong benefits for their teams, and add 401k, workers comp, and HR support along the way. Charlie and Daniel walk through the real questions agents have been asking: the W-2 and contract concerns, group size rules, the October 1 onboarding window, the 15 month rate lock, and who this does and does not fit. Their commitment throughout is simple: help agents, honor their relationships, and never poach their business.

GET CONNECTED
Affected by the changes? Start here and our team will collect your details to build your quote:
https://greyhawkinsurance.useindio.com/sign-up/3m7V3j5kJzqp_rWcLfeR

Daniel is handling these conversations personally, and we will be running webinars over the coming weeks to answer more questions.

CHAPTERS
00:00 The contract change that shook captive agents
00:39 Why this episode is powered by Greyhawk
01:23 The big one: benefits cut from the corporate plan
01:44 Greyhawk's promise: help agents, never poach
02:23 The exclusive BBSI benefits program
03:13 Large group vs small group (why your rates jump)
04:16 Why BBSI, and the nationwide exclusive
05:09 The W-2 and contract questions, answered
07:49 Group size rules and workers comp
08:49 What is included: 401k, life, dental, vision
10:08 Nationwide support and the Aetna and Kaiser network
10:52 October 1 onboarding and the 15 month rate lock
12:15 How strong benefits help you hire and retain
13:18 Who this is, and is not, for
13:50 Timeline, deadlines, and no gap in coverage
16:15 "Don't be scared of it": the market has changed
17:31 Greyhawk's commitment and how to get connected

FOLLOW THE SHOW
Instagram: @greyhawkinsurance

Music from #Uppbeat (free for Creators!):
https://uppbeat.io/t/pryces/got-it
License code: F2GNGAOFQSYFTKPQ

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: cause-of-loss investigations, telling the difference between real damage and fraud, and helping people get answers in their hardest moments.

But this conversation is as much about building a business as it is about engineering. Michael shares his unlikely path from pastor to entrepreneur, the case that hooked him on forensics, the licensing mistake that nearly sank the company, and how he grew Vision from a spare-bedroom office to a firm of more than 80 people covering all 50 states in about five years. Along the way: betting on yourself, leading with faith, taking care of your people, and why real entrepreneurs are builders, not get-rich-quick day traders.

CHAPTERS
00:00 A different kind of insurance episode
00:35 What forensic engineering actually is
01:42 Real damage vs fraud: the ball-peen hammer tell
03:09 When adjusters get it wrong
05:56 Meeting people in their hardest moments
06:48 From pastor to forensic engineering
08:11 The case that hooked him
10:25 Starting his own firm, and the licensing mistake
15:38 From 8 states to all 50
17:26 Hitting $1M in three and a half years
19:21 Betting on yourself, and faith through the fear
22:02 "$90K in debt... rookie numbers"
24:16 Taking care of your people, thinking generationally
31:21 Lawsuits, intimidation, and the 3% who don't quit

ABOUT THE GUEST
Michael Ross is the founder of Vision Forensic Engineering, a national firm providing cause-of-loss investigations and building consulting for insurance companies and private parties. A former pastor turned entrepreneur, he built the company from eight states to all fifty, and from a spare bedroom to more than 80 people, in roughly five years.

FOLLOW THE SHOW
Instagram: @greyhawkinsurance

Music from #Uppbeat (free for Creators!):
https://uppbeat.io/t/pryces/got-it
License code: IJFRDULSIGSMATU5

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 Deaver sits down with John Young: former UCLA football player, longtime liquor industry veteran, and now a producer at Greyhawk Premier Insurance Solutions.

John breaks down the generational shift that is quietly reshaping the alcohol business, including the stat that stopped Charlie cold: 80 percent of alcohol is consumed by just 20 percent of drinkers, and those drinkers are aging out. He talks about why he walked away from a successful sales career, what made him choose a smaller, family oriented shop over a big corporate agency, and what his first two months inside Greyhawk have actually been like.

It is an honest conversation about career change, betting on yourself, and what it looks like to do right by the people you serve.

CHAPTERS
00:38 Meet John Young
01:36 LA roots: Loyola and UCLA football
03:04 "Man for others": the Loyola network
04:39 Injuries and walking away from football
06:20 Family
06:56 From Aldi to a decade in liquor
08:05 How the pandemic gutted hospitality
10:27 Why nobody is drinking anymore
11:56 The pivot into commercial insurance
13:23 Why he chose the small shop over corporate
16:29 Two months in: learning inside the bullpen
19:30 What insurance really means, and the Greyhawk difference
22:03 Closing thoughts

For more info on careers at Greyhawk: careers@greyhawkinsurance.com

Edgar Corona is our VP of Personal Lines at Greyhawk. We discuss:

- Shifting from big-name employers (In-N-Out and State Farm), to Greyhawk
- Trusting your gut
- The importance of life insurance (at any age)
- State Farm pulling out of California
- Pros and cons of the brokerage side of the insurance industry
- California Fair Plan = "nothing fair about it"
- Why it always pays to be honest
- Becoming the largest insurance brokerage in Santa Clarita, CA
- Plans for future growth

From Eddie: With over a decade of experience in the insurance industry. I specialize in providing tailored risk management solutions that protect business and individuals. At Greyhawk Insurance, I focus on delivering personalized service, ensuring clients understand their coverage while securing the best policies for their needs. My expertise spans in property & casualty and Life & Health. I'm passionate about building lasting relationships and staying ahead of the industry trends to offer protective solutions.

For more info on personal insurance contact Eddie at: ecorona@greyhawkinsurance.com For more info on careers at Greyhawk: careers@greyhawkinsurance.com