This episode is something fun and a little different! You get a one-on-one with Jimmy and cohost Caitlyn, to zoom in on a topic that they both know extremely well: entrepreneurship. You'll hear the honest truth about the challenges and stresses of starting your own business from scratch, plus the things that they love the most about being their own bosses. The conversation takes a look at the ugly reality of things like expected freebies, and how difficult it is to not receive much praise or feedback. We also dive into March Madness, modern dating culture, questions around trans athletes, and the evils of cancel culture brought on by social media. Finally, we finish off with a call to you, our shipmates, to send us your stories of positivity and gratitude: let's spread the love! So, to learn everything you didn't know you needed to know about entrepreneurship, join us for another dynamic episode!

Key Points From This Episode:

• Introducing our topic for the day: entrepreneurship.
• Hear about Caitlyn's business: CRW Media, who are also doing Jimmy's website.
• When Caitlyn started her entrepreneurship journey.
• How the core beliefs instilled in the Navy translate well to running a business.
• Why many people who come out of the military become entrepreneurs.
• Some tough lessons to learn when it comes to friends and family.
• Our rapid-fire section: shooting the breeze about vacations, traffic, and gambling. 
• Diving into dating culture: pick-up lines, who pays the bill, dating apps, and more.
• Some inspiring advice on resilience and the best parts of working for yourself.
• How praise really matters and is appreciated when you're doing it all on your own. 
• Discussing the Carlos Correa deal, March Madness, Coach K, and the rivalry between Duke fans and Tarheel fans. 
• Hear some of our favorite baseball stadiums and why.
• Caitlyn gets into how Coach K acted like an entrepreneur.
• Talking about the 24/7 nature of being an entrepreneur.
• Venting our frustrations about a man coming into a woman's swimming competition. 
• Where we need to draw the line when it comes to social justice issues.
• Questioning how trans athletes can compete without taking away women's rights.
• Caitlyn and Jimmy share their views on feminism and more traditional gender roles.
• Talking about cancel culture and how harsh and unnecessary it is. 

Tweetables:

“[Being in the military] gives you that leadership personality, especially the Navy.”— Caitlyn Warren [0:03:42]

“Those people that actually support us and get it? That's who we keep coming back for every single day.”— Caitlyn Warren [0:08:43]

“It is very rewarding, we do have the flexibility with our schedules. When I say you can make us much money as you want or as less as you want, to me it's true. It all depends on how hard you're going to work and how many hours you're going to put in.”— Jimmy Rogers [0:08:50]

“Everybody matters, across the board, top to bottom. Founder, co-founder, vice president, president, janitor. Everybody should get a little bit of love and appreciation.”— Jimmy Rogers [0:22:04]

“People don't understand just how [entrepreneurs] feel. We put the most into it from an emotional standpoint.”— Jimmy Rogers [0:33:38]

Links Mentioned in Today’s Episode:

Jimmy Rogers on LinkedIn

Sailor Jimmy on Instagram

Sailor Jimmy on TikTok

Sailor Jimmy on Facebook

CRW Media

Boots for Troops

Scafom North America