2Bobs—with David C. Baker and Blair Enns

Hosted by David C. Baker and Blair Enns

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Episodes

248

Latest episode

Aug 2026

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About the show

Conversations on the art of creative entrepreneurship with David C. Baker and Blair Enns

Listen to episodes

60 recent

August 12, 2026Episode 24826 min

Positioning, 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. Links Positioning: 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

July 29, 2026Episode 24720 min

Employee 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

July 15, 2026Episode 24623 min

Productization (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

July 1, 2026Episode 24520 min

Thirteen 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

June 17, 2026Episode 24424 min

Embrace 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

June 3, 2026Episode 24326 min

Firms 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). Links "Most At-Risk Shops" by David C. Baker for punctuation.com

May 20, 2026Episode 24220 min

Pricing 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

May 6, 2026Episode 24121 min

People 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. Learn more and apply at 2Bobs.com/events

April 22, 2026Episode 24029 min

Three 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 Brigadoon.live "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

April 8, 202619 min

Why 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 "The Waterfall of Differentiation" 2Bobs episode