- 26 minutes 40 secondsPositioning, Strategy, and AI
Blair and David are hearing all kinds of people talking about how their positioning needs adjustment because of AI. Blair does see an issue developing for many creative firms, but more with business strategy instead of positioning.
LinksPositioning: The Battle for Your Mind and The 22 Immutable Laws of Marketing by Al Ries and Jack Trout
Good Strategy / Bad Strategy by Richard Rumelt
Playing to Win by Roger L. Martin
The Lords of Strategy by Walter Kiechel, III
12 August 2026, 11:00 am - 20 minutes 36 secondsEmployee Retreats for Remote-First Teams
David recommends regular in-person company-wide gatherings for remote workers as an opportunity for creative agencies to help build their organization's culture in our post-pandemic economy where online video meetings continue to fill our calendars and working from home is the new norm.
LINKS
"Investing in Ee Retreats at Remote Firms" by David C. Baker for punctuation.com
29 July 2026, 11:00 am - 23 minutes 30 secondsProductization (Again)
Blair changes his mind on productized services. Again. And AI is the reason.
LINKS
"The New Age of Consulting" by Blair Enns for winwithoutpitching.com
15 July 2026, 12:03 pm - 20 minutes 28 secondsThirteen Signals Your Website Should Send
David shares a quick list of website elements he sees is missing from a lot of creative firms' websites which could help them attract more new business.
Links"13 Signals Your Website Might Send" by David C. Baker for punctuation.com
1 July 2026, 11:44 am - 24 minutes 45 secondsEmbrace the Marketing Mess
Blair shares what stuck in his mind about marketing success from listening to a recent podcast interview with Rory Sutherland on Liam Curley's Undisputed Authority.
Links"Embrace the Marketing Mess" article by Blair Enns for winwithoutpitching.com
Rory Sutherland podcast interview on Liam Curley's Undisputed Authority
17 June 2026, 12:07 pm - 26 minutes 43 secondsFirms Most at Risk
Which segments of our field will thrive in the near future and which ones will slowly lose relevance, and why? David wants creative entrepreneurs to continue being resilient and reinventing themselves every two years while keeping a watchful eye on constantly evolving industry practices and technologies (including AI).
Links3 June 2026, 12:13 pm - 20 minutes 18 secondsPricing Resentment
Blair sees creative entrepreneurs opening themselves up to pricing resentment from their clients when the value of their contributions diminishes over time, especially when they've created significant economic value at the beginning of a long-term engagement.
LINKS
"Is Your Pricing Creating Resentment?" by Blair Enns for winwithoutpitching.com
20 May 2026, 11:00 am - 21 minutes 41 secondsPeople vs. Profits
Prompted by a recent trip to Europe, David considers how the differences between worker protection laws in Europe compared to North America affect starting and running an agency in this fast-changing global economy.
Links"Employment Law + Economic Flexibility" by David C. Baker for punctuation.com
2Bobs in Tuscany
Join David, Blair, six other business owners and their spouses for four days and nights of creative business exploration in an intimate countryside villa designed for long meals, deep conversations, and unhurried thinking.
6 May 2026, 10:00 am - 29 minutes 24 secondsThree Patterns of Lost Opportunities
Blair identifies three recurring categories of lost sales in creative firms and offers solutions to each. Fixing two of these patterns can reap the dividends immediately, and adjusting your sales approach for all three will pay off for years.
LINKS
"Three Patterns of Lost Opportunities" article by Blair Enns for winwithoutpitching.com
"Slapping Down Your Childlike Glee" 2Bobs episode
"Debriefing After a New Business Call" 2Bobs episode
"Assume an Advantaged Player" 2Bobs episode
"The Rungs You Can Reach on the Ladder of Lead Generation" 2Bobs episode
22 April 2026, 1:55 pm - 19 minutes 43 secondsWhy Clients Come, Stay, and Leave
David sees a lot of creative agencies making bad assumptions about their client relationships by not making the distinction between the reasons why clients come to them in the first place, why they choose to continue working with them as time passes, and then why they ultimately move on.
LINKS
"Distinguishing Between Why Clients Come, Stay, and Leave" by David C. Baker for punctuation.com
8 April 2026, 11:00 am - 27 minutes 45 secondsIs AI Going to Kill Labor-based Pricing?
Blair is stunned that he still encounters so many advisory businesses like ad agencies, consulting firms, legal and accounting practices — large and small — that are still selling time. So he and David discuss what new revenue models should look like as we all adapt to how AI is changing our businesses.
Links"Time's Up, Babycakes" by Blair Enns for winwithoutpitching.com
Time's Up!: The Subscription Business Model for Professional Firms by Paul Dunn and Ronald J. Baker
The Automatic Customer: Creating a Subscription Business in Any Industry by John Warrillow
The Forever Transaction by Robbie Kellman Baxter
Subscribed: Why the Subscription Model Will Be Your Company's Future – and What to Do About It by Tien Tzuo and Gabe Weisert
25 March 2026, 11:00 am - More Episodes? Get the App