In this episode of Burning the Ships, I sit down with Kyle Doriety, a South Carolina investor who just did what most people only dream about: quit his job after 11 years to go all-in on entrepreneurship.
Kyle’s journey started on a family farm, where he learned the value of hard work from his parents and grandparents. He spent more than a decade in a secure, well-paying corporate job before deciding that comfort wasn’t the same as calling. What started as a single rental property turned into a growing real estate portfolio, multiple business ventures, including ice vending machines and ice delivery services and, most importantly, the freedom to work for himself.
We talk about what it really takes to walk away from the W-2 world, how faith and persistence played a role in his journey, and the power of having a supportive spouse who believes in your vision even before the results show up.
If you’ve ever thought about burning the ships yourself, this episode is a playbook in courage, resourcefulness, and grit.
Key Talking Points of the Episode
00:00 Introduction
03:10 Leaving the corporate world: Kyle’s last day at his job and how it really felt
05:10 Growing up on a South Carolina farm and learning the value of hard work
08:04 How early independence and a “contrarian” spirit led to entrepreneurship
10:01 The moment he realized a 9-to-5 wasn’t his path
13:35 Hitting career milestones but feeling unfulfilled and recognizing when “success” isn’t enough
17:23 The turning point: deciding to take control of his future through real estate
18:50 The power of a supportive spouse and why belief matters more than money
23:10 Building confidence through evidence
24:37 $15K saved, $5K in renovations: lessons learned from the first deal
27:22 Leveraging a 401(k) withdrawal to invest in passive income assets
28:02 The ice vending business: turning a simple idea into steady cash flow
30:12 Scaling through innovation: adding credit card readers and ice delivery
33:11 Finding a niche in construction and industrial ice delivery
36:11 Balancing marriage, a full-time job, and side hustles without burning out
41:35 Fix-and-flip vs. buy-and-hold strategy: how Kyle structures his business today
44:20 Understanding buy boxes, market focus, and why he’s targeting small multifamily
46:44 Long-term vision: freedom, travel, and the dream of owning a Cirrus SR22 airplane
51:13 How family values and hard work shaped Kyle’s resilience
56:53 The mindset of constant improvement and never “arriving”
59:01 Mentorship and masterminds: how surrounding yourself with the right people changes everything
Quotables
“You just got to be persistent. You got to keep going. You got to have faith. I don’t know how people do it without faith.”
“My wife’s got more confidence in me than I do. She told me for years, ‘Kyle, quit your job. I don’t care. I know you’ll figure it out.’”
“Grit built my business, but faith sustains it.”
Links
608B Capital
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