Calendly CEO on Handling the Unexpected, Ted Lasso's Sudeikis on Digital Shifts, TripActions CEO on Travel's Return

Tope Awotona of Calendly, Jason Sudeikis of Ted Lasso, Ariel Cohen of TripActions

Bold new ideas don't often get a warm welcome. Entrepreneurs have to fight to get them off the ground, and it can take more than one attempt to truly hit it big. Well, the founders of Atlassian hit the jackpot with their first effort out of college — but the other standouts I spoke with this week told a different story, whether the backdrop was Silicon Valley or Hollywood.

Here we go:

More R&D, Less Sales: Atlassian Co-CEO Mike Cannon-Brookes on Working Lunch

In the latest Working Lunch on CNBC's Power Lunch Atlassian co-founder and co-CEO Mike Cannon-Brookes talked to me about the company's unconventional approach to software sales, and how he became an owner of the NBA's Utah Jazz:

A Date With Destiny: Calendly CEO Tope Awotona

Calendly CEO Tope Awotona's journey hasn't followed a conventional schedule; he's dealt with tragedy, big moves and failed startups. Now his startup carries a $3 billion valuation, and he's eyeing more growth:

Business Travel Returns, With A Twist: TripActions CEO Ariel Cohen

TripActions CEO Ariel Cohen has learned to pour himself into challenges he truly cares about, and to take breaks to preserve his health. We talked about the future of business travel, and why he takes a solo vacation every year:

Streaming Platforms and Digital Tools Open the Creative Market: Jason Sudeikis

Ahead of his turn hosting Saturday Night Live this weekend, I talked to Emmy winner and Ted Lasso actor/writer/producer Jason Sudeikis about how technology is changing the creative economy:

Should PayPal Buy Pinterest? On the Other Hand

Would it be a good idea for PayPal to buy Pinterest? I argued both sides in the latest edition of On the Other Hand on CNBC's Squawk Box:

Check out The Black Experience in America: The Course, an online educational resource I researched, designed and built. A free PDF download is available to bring the material to kids, and the online interactive experience is made for adults.