Everybody wants more friends, but nobody knows how to make them.
This week, we’re joined by D’Art Strickland, Senior Solutions Marketing Manager at BigID, to talk about something most of us feel but rarely admit: it’s hard to make friends as a grown-up.
After a major life shift left him sitting on the couch wondering what changed, D’Art decided to get uncomfortable. From “Dinner with Strangers” to driving Uber for human conversation, he began intentionally pursuing connection, not because it was easy, but because it mattered. His work in enablement mirrors the same philosophy: move from transactional to relational, lead with curiosity, and remember that we’re human first.
In this conversation, we explore why everyone wants more friends but no one knows how to make them, how bravery and vulnerability go hand in hand, and what it means to reclaim your “sparkle.” D’Art shares how small, intentional acts of courage, even just walking into the bar instead of driving past it can shift isolation into belonging.
What you’ll learn:
Jump into the conversation:
(00:00) Introduction
(04:16) Bingo night energy: inside jokes and setting the tone
(05:07) Sales enablement explained: from black hole to confidence builder
(09:53) ‘D’Art and the Deal’: building confidence through community
(16:22) Making friends as a remote adult: dinners with strangers & Uber
(25:13) Connected yet disconnected: the cultural tension (+ ALX break)
(28:12) Why adult friendships feel hard and the need for third places
(28:28) Building community on purpose: the Bozeman Knights experiment
(29:06) Bravery by default: choosing discomfort over comfort
(29:45) Acquaintance vs. friend: the phone number barrier
(32:15) Why asking feels awkward (for men and women)
(35:18) The dive bar story: you can’t fail by trying
(40:17) Health, fun, and finding the sparkle again
(43:39) Facilitating connection at work and the call to be human
Connect with D’Art Strickland: https://www.linkedin.com/in/dartstrickland/
Check out BigID: https://bigid.com/
Check out Arcadia: https://www.BeArcadia.com
Connect with Sam Yarborough: https://www.linkedin.com/in/sam-yarborough/
Connect with Jason Yarborough: https://www.linkedin.com/in/yarby/
Produced in partnership with Share Your Genius
