One of the most common questions I hear from my community has to do with friendship: How do we find the ride or dies that’ll always be in our corner? Today, I’m bringing you my best friend of over 20 years, Jenna Free, to throw open the vault and share her experiences cultivating supportive friendships as a serial entrepreneur—oh, while also spilling some of my deepest, darkest secrets while we’re at it! We unpack how to not only find the right people that uplift you, but maintain and deepen the kind of friendships that’ll bring your biggest dreams to life. We’ll explore the real challenges that come with success (including proof that it doesn’t have to be lonely at the top), the hardest lessons & the incredible blessings our seasons of friendship have taught us, as well as tangible ways you can show up in your relationships with more authenticity and vulnerability.
HIGHLIGHTS
00:00 Meet my bestie of 20 years, Jenna Free!
07:35 How to maintain and deepen your friendships (even through evolving seasons).
13:30 What have your experiences with female friendships taught you?
18:30 Ways to form authentic and vulnerable friendships with other women.
26:30 What is the greatest opportunity for connection, if we allow it?
29:50 The hardest lessons and the biggest blessings of friendships.
33:20 How do friendships shift when you experience success?
40:45 Ways to cultivate supportive networks in your industry.
46:45 The surprising things you never knew about Lindsey!
50:15 What are the biggest lessons our friendship has taught us?
54:30 Celebrating Jenna’s Powerhouse moment passing all of her licensing exams (with her Masters).
RESOURCES + LINKS
Click HERE for tickets to the 2025 Powerhouse Women Event August 15-17th in Scottsdale, Arizona!
Powerhouse Women is a COMMUNITY and YOU are part of it! Take a screenshot of this episode and tag us on Instagram so we can keep the conversation going and create more of the episodes you need!
FOLLOW
Cool Times Podcast: @cooltimespodcast
Visit the FREEZ Construction website: https://www.freezconstruction.com/
Powerhouse Women: @powerhouse_women
Lindsey: @lindseymarieofficial
Visit the Powerhouse Women website: powerhousewomen.co
Join the PW Community Facebook Group: facebook.com/groups/powerhousewomencommunity
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
The Breakfast Club
The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy And Charlamagne Tha God!
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.