Fiona Killackey talks with the incredible Josh Rubin, photographer, interaction designer and co-founder of Cool Hunting,the award-winning independent publication company that tackles the most intriguing stories about design, culture and technology. In this interview, Josh shares Cool Hunting’s history, what influences him in making business decisions and what his advice is for small business owners dealing with overwhelm and stress. Topics discussed in this episode: Introducing Josh Rubin, co-founder of Cool Hunting (1:19)What is Cool Hunting? (5:08)When did it start? (6:28)When did Cool Hunting move from a simple blog into something more? (7:59)What was Josh Rubin’s upbringing like?(10:50)What is Freehands? (13:40)What is Cool Hunting’s “Why”? (16:11)What is Josh Rubin’s background and how did they get advertisers? (20:04)What is his advice for family, friends and partners who want to start a business together? (23:57)What is Cool Hunting’s internal process in collaborations and other partnerships? (27:27)How does Cool Hunting find content despite the many competitors? (29:46)What are the books, podcasts, websites, people that you would recommend for small business owners to check out? (32:02)How do you deal with areas of the business that are out of one’s expertise? (33:48)What advice would Josh give to a small business owner who's feeling overwhelmed from the business? (35:24)What does Josh think when he looks back at the accomplishments of Cool Hunting? (39:11)Conclusion (39:56)Resources mentioned in this episode: freehands (14:46)Headspace (36:36)Episode transcript:Find the full transcript of this episode of at mydailybusinesscoach.com/podcast/2Thanks for listening to the My Daily Business Coach podcast. If you want to get in touch, you can do that at mydailybusinesscoach.com or hit me up on Instagram @mydailybusinesscoach.And you can check Cool Hunting out if you don't know about it, which I would be very surprised, but it's just coolhunting.com. You can also find them on Instagram to @coolhuntingTo make sure that you don't miss out on any other interviews I do with creative, small business owners on this podcast, please make sure that you hit subscribe.If you want to get in touch, you can do that at mydailybusinesscoach.com or hit me up on Instagram @mydailybusinesscoach Special thanks to our sponsor, Vanta AI. Get $1000 off at vanta.com/mydailybusiness Want to get your #smallbusiness sorted in 2026? Check out our 1:1 business coaching packages from a one-off session to 6-months of coaching. Want to know more about AI and how to harness it for your small businesS? Join our new monthly AI chat for small business owners. You can join anytime at www.mydailybusiness.com/AIchat Try out my fave AI tool, Poppy AI here and use discount code FIONA. We also love Descript. Connect and get in touch with My Daily Business via our shop, freebies, award-winning books, Instagram and Tik Tok.

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