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