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

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Do You Need an Advisory Board?

September 23, 2026 16:50 2.85 MB ( 13.29 MB less) Downloads: 0

We all know how valuable external input from trusted advisors can be for our business. But what does that look like for independent agencies who don't have investors to answer to?   LINKS "Do Independent Firms Need A Board?" by David C. Baker for punctuation.com

A Proposed AI Contribution Scale

September 09, 2026 20:34 20.02 MB Downloads: 0

Categorizing AI-generated copy as "human vs AI" is not as binary as with AI-generated images or video. So Blair has developed an AI Contribution Scale to help us all be more transparent when using LLMs in the creation of written communication intended for prospects, clients, and peers. [This episode's notes are AI-0] ‍ ‍ Links AI Contribution Scale "The Coming Collapse of 'Thought Leadership'" by Blair Enns for winwithoutpitching.com Curt Jaimungal's 5-minute YouTube video on why you shouldn't let AI write for you

How Sellable Are You?

August 26, 2026 22:14 21.61 MB Downloads: 0

In a recent article, David discloses the questions all creative agency principals need to answer whenever they are ready to find the right buyer and successfully navigate the merger and acquisition (M&A) process to complete the sale.   LINKS "How Sellable Is Your Firm?" by David C. Baker for Punctuation.com

Positioning, Strategy, and AI

August 12, 2026 26:40 25.88 MB Downloads: 0

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

Employee Retreats for Remote-First Teams

July 29, 2026 20:36 20.05 MB Downloads: 0

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

Productization (Again)

July 15, 2026 23:30 22.84 MB Downloads: 0

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

Thirteen Signals Your Website Should Send

July 01, 2026 20:28 19.93 MB Downloads: 0

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

Embrace the Marketing Mess

June 17, 2026 24:45 24.02 MB Downloads: 0

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

Firms Most at Risk

June 03, 2026 26:43 25.92 MB Downloads: 0

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

Pricing Resentment

May 20, 2026 20:18 19.76 MB Downloads: 0

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

People vs. Profits

May 06, 2026 21:41 21.09 MB Downloads: 0

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

Three Patterns of Lost Opportunities

April 22, 2026 29:24 28.5 MB Downloads: 0

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

Why Clients Come, Stay, and Leave

April 08, 2026 19:43 19.2 MB Downloads: 0

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

Is AI Going to Kill Labor-based Pricing?

March 25, 2026 27:45 26.91 MB Downloads: 0

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

If I Were Starting a New Firm

March 11, 2026 34:46 33.36 MB Downloads: 0

Blair interviews David about a recent article he's been receiving a lot of feedback on, in which he lists all of the things he would try to incorporate into a brand new creative agency, based on what he's seen and learned from working with thousands of firms over the years.   Links "If I Started A New Firm, Now" by David C. Baker for punctuation.com