Working (and Not Working) From Spain and the Maldives
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We're back for episode six! Hosted by best friends, seasoned entrepreneurs, and investment coaches Ashley and Scottie, this episode picks up the raw, unscripted conversation about what it actually takes to build a life and business on your own terms.
This week, Ashley and Scottie get into the planning behind their upcoming Spain and Maldives trip — from manifesting it into existence to preparing the business (and themselves) to actually disconnect. Expect candid, living-room-style conversation covering:
From Vision Board to Reality: The Spain and Maldives Trip: Ashley and Scottie share how a manifested Maldives trip came together through a friend's content-for-stay partnership — and the reminder that you have to actually ask for what you want to get it.
Traveling Together, Working Apart: Why aligning on which days are work days and which are play days before the trip even starts eliminates guilt and misaligned expectations between travel partners.
Working Backward From the Trip: How planning the getaway forced Ashley and Scottie to think differently about their business — hiring two new people, building out SOPs, and handing more off to their team well before takeoff.
Right-Sizing the Ship: Scottie opens up about a brutal stretch in late 2024 when ad spend outpaced revenue — and how having recovered from it before gives him the calm certainty that he can handle whatever the business throws at him.
Building a Routine That Travels With You: Why isolating specific working hours (instead of leaving work open-ended) keeps a trip from feeling like a second job, plus the story of a friend who stays grounded anywhere by keeping the same morning routine.
Don't Come Back Needing a Vacation From Your Vacation: Ashley explains why she keeps up workouts and step counts on trips instead of abandoning her routine entirely — so indulging in the fun stuff doesn't leave her feeling worse when she's back.
Ashley and Scottie aren't here to give you textbook theories or gatekeep their strategies. Whether you're an advisor trying to scale, an entrepreneur navigating the messy middle, or someone looking for honest advice from two friends who have actually been in the trenches, you're in the right place. Grab your favorite drink (or a glass of whole milk coffee), pull up a chair, and join the conversation.