2Bobs—with David C. Baker and Blair Enns

2Bobs—with David C. Baker and Blair Enns

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

Episodes

September 9, 2026 20 mins

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]

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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

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August 12, 2026 26 mins

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.

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Positioning: The Battle for Your Mind and The 22 Immutable Laws o...

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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.

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July 15, 2026 23 mins

Blair changes his mind on productized services. Again. And AI is the reason.

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"The New Age of Consulting" by Blair Enns for winwithoutpitching.com

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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.

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"13 Signals Your Website Might Send" by David C. Baker for punctuation.com

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June 17, 2026 24 mins

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.

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"Embrace the Marketing Mess" article by Blair Enns for winwithoutpitching.com

Rory Sutherland podc...

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June 3, 2026 26 mins

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).

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May 20, 2026 20 mins

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

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May 6, 2026 21 mins

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.

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"Employment Law + Economic Flexibility" by David C. Baker for punctuation.com
...

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April 22, 2026 29 mins

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.

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"Three Patterns of Lost Opportunities" article by Blair Enns...

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April 8, 2026 19 mins

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 e...

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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.

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March 11, 2026 34 mins

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.

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"If I Started A New Fi...

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February 25, 2026 21 mins

Blair differentiates between decoy pricing and price anchoring, which are two different techniques that are often confused for each other, and can increase your average proposal value in multi-option pricing when used appropriately.

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"Decoy or Anchor?" article by Blair Enns for winwithoutpitching....

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February 11, 2026 20 mins

Despite the fact that many entrepreneurs hate people telling them what to do, they end up running their own agencies using a "central planning" model. Instead, David encourages entrepreneurial leaders to set clear standards, give staff more freedom, and institute kind accountability, for them and ourselves.

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"Countering Your 'Central Planning' Tendencies" by David C. Bak...

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January 28, 2026 20 mins

David interviews Blair about his recent article in which he gives us methods to cope with our own natural emotional and physiological responses that can be triggered when unforeseen events unfold within sales conversations.

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"Can Improv and Cold Plunges Improve Your Sales?" by Blair Enns for winwithoutpitching.com

Blair's interview on the Undisputed Authority podcast with Liam Curley

What Doesn't Kill Us by Scott Carney

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January 14, 2026 23 mins

Blair interviews David about a recent article in which he argues that the very traits that make entrepreneurs successful also make it hard for them to give up being their own boss and join someone else's company.

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"What Makes Entrepreneurs Unemployable" by David C. Baker for punctuation.com

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December 31, 2025 20 mins

David interviews Blair about his recent article in which he explores how our businesses are not simple machines that can be tuned (or killed) with specific wrenches, but they are complex adaptive organisms that we need to understand differently.

LINKS

"Your Business Is Not a Machine" by Blair Enns for winwitoutpitching.com

"Innofficiency in Your Agency" 2Bobs episode

"Grow or Die?" 2Bobs episode

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David sees too many marketing agencies trying to attract new business by staking claims of specialness on things for which nobody is claiming the opposite, instead of building their positioning on uniquely defined expertise.

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