Friends with Benefits
Welcome to Friends with Benefits, the business podcast about revenue-generating partnerships.
Not "business time" with friends.
This podcast is for those looking to build professional relationships that last and add tremendous value to your company and maybe even, you personally.
Join hosts Jason and Sam Yarborough, who happen to be married, as they talk with some of the best in the industry.
We will be tackling topics like what good partnerships looks like, how relationships can build immense value for your business, and why even though strategy, pipeline, and growth are the goals, it all comes down to relationships. Let’s face it, business is done person-to-person.
Discover how personal connections transcend the boundaries of business time. Come hang out with us for inspiring stories, actionable strategies, and valuable insights that will empower you to forge meaningful partnerships in today’s competitive landscape.
Because we all know, business time is personal.
Friends with Benefits
Choosing Discomfort to Find Connection with D’Art Strickland
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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:
- Why making friends as an adult feels so hard and what to do about it
- The difference between transactional and relational living at work and in life
- How curiosity fuels confidence, storytelling, and deeper human connection
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
https://www.shareyourgenius.com