184 - Taking Risks — with Jason Fried

184 - Taking Risks — with Jason Fried

Jason Fried is the founder and CEO of Basecamp. Once a web design firm (and operating under the name 37Signals), Basecamp unintentionally pivoted into building software with their namesake product. They also created the email app HEY, a fresh take on an old idea. As you can imagine, Jason is no stranger to change. In this episode, he shares how Basecamp accidentally came to be and the struggles they’ve encountered along the way. Like working remotely, building new products, and taking calculated risks that from the outside might look crazy. Change is inevitable, but it’s rarely easy, especially for a company where people are the driving force. Shifts in direction profoundly affect company culture, and how you manage that change can make or break your business. Learn more about your ad choices. Visit podcastchoices.com/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices

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Episoder(437)

Why Chasing Metrics Ruins Your Content w/ Chris Do | Ep 417

Why Chasing Metrics Ruins Your Content w/ Chris Do | Ep 417

In this episode, Chris Do challenges the belief that content performance should be measured by likes, views, or algorithmic wins. He explains why treating social media as a scorecard disconnects creat...

31 Jan 13min

Playing the Long Game in Business and Life w/ Jodie Cook | Ep 416

Playing the Long Game in Business and Life w/ Jodie Cook | Ep 416

In this episode, Chris Do sits down with Jodie Cook for a wide-ranging conversation about playing the long game in business, relationships, and life. They unpack the difference between short-term wins...

29 Jan 1h 16min

How to Beat the Competition Without Lowering Your Prices w/ Chris Do | Ep 415

How to Beat the Competition Without Lowering Your Prices w/ Chris Do | Ep 415

In this episode, Chris Do challenges the belief that creative work is a commodity and explains why lowering prices is rarely the right solution. He reframes competition through the lens of imagination...

24 Jan 6min

Turning Life’s Hardest Moments Into Growth w/ Dr. John Demartini| Ep 414

Turning Life’s Hardest Moments Into Growth w/ Dr. John Demartini| Ep 414

In this episode, Chris Do sits down with Dr. John Demartini for a wide-ranging conversation on human perception, trauma, and the power of reframing life experiences. Dr. Demartini shares his extraordi...

22 Jan 48min

The Secret Behind Authentic Personal Branding w/ Mo Ismail| Ep 413

The Secret Behind Authentic Personal Branding w/ Mo Ismail| Ep 413

In this episode, Chris Do and Mo Ismail explore why personal branding works best when it starts with generosity rather than self-promotion. They break down how leading with genuine care lowers defense...

17 Jan 7min

Why Creatives Struggle With Feedback w/ Jule Kim | Ep 412

Why Creatives Struggle With Feedback w/ Jule Kim | Ep 412

In this episode, Chris Do and Jule Kim unpack why feedback is both essential and emotionally difficult for creatives. Drawing from decades of teaching, coaching, and public critique, they explore the ...

15 Jan 1h 29min

How to Market Your Services the Right Way w/ Chris Do | Ep 411

How to Market Your Services the Right Way w/ Chris Do | Ep 411

In this episode, Chris Do breaks down why most creatives struggle to market their services effectively—and how that changes in 2026. He explains the critical difference between designing for “anyone” ...

10 Jan 13min

The Business of Design Systems and Standards w/ Jesse Reed | Ep 410

The Business of Design Systems and Standards w/ Jesse Reed | Ep 410

In this episode, Chris Do sits down with designer, publisher, and entrepreneur Jesse Reed to explore the intersection of design systems, business, and long-term creative impact. Jesse shares his journ...

8 Jan 1h 11min

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