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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.

All Episodes

Friends with Benefits

Work Questions You'd Never Ask Out Loud with Heather Cooper and Blakely Graham

May 12, 2026 • Sam and Jason Yarborough • Season 3 • Episode 23

0:00 | 52:35

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The best leaders aren't just built in boardrooms, they're built in the moments nobody sees.

This week, we're joined by Heather Cooper, former CEO of Cloud Coach, and Blakely Graham, former CEO of TaskRay, now co-hosts of the podcast Not All Business, for a rare, unfiltered conversation about competition, connection, and what it really costs to lead. Heather and Blakely spent over a decade as rival CEOs in the Salesforce ecosystem, building competing companies, never once meeting. Until, a mutual friend changed everything. In this conversation, we explore how their unlikely friendship became the foundation for something bigger, what they both silently carried as leaders, and why the loneliness of the corner office is the topic nobody wants to admit to.

We also dig into the realities of building a people-first culture in a world obsessed with top-line numbers, what it looks like to lead with humor and humanity, and how both women redefined success after their exits. From crying in bathrooms between negotiations to bootstrapping profitable companies without a single investor dollar, Heather and Blakely don't hold back. Whether you're a founder, a leader, or someone who's ever felt like they had to have it all together, their honesty, laughter, and hard-won perspective are exactly what you need to hear.

What you’ll learn: