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
Be sure to visit the podcast's website and support the creator: 2bobs.com
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Episodes
Demand Is the New Supply 04.11.2026 23:54
Blair recognizes that AI has triggered a knowledge product oversupply and now we have a signal-to-noise ratio problem. He sees reputation and reach reshaping the knowledge economy, consolidating a lot of power and wealth among a smaller number of experts who demonstrate their trustworthiness and rise above the noise. Links "Demand Is the New Supply" by Blair Enns for winwithoutpitching.com: http...
Inside the Head of a CMO 21.10.2026 25:53
Given the data from recent research about Chief Marketing Officers, David has four things creative agencies should keep in mind during sales and work interactions with them. LINKS "Inside the Head of a CMO" by David C. Baker for punctuation.com The Boathouse Fifth Annual CEO Study Confessions of a CMO: A Field Guide to How CMOs Are Evolving to Thrive Under Corporate Pressure
Get Your Freak On! 07.10.2026 25:41
Blair has been thinking about how, as AI continues to streamline more administrative tasks over time, we will be left to focus on the things we humans are good at – interacting with other humans. Because of this, the interesting people will win in selling their services and expertise. Links "The Interesting People Will Win" by Blair Enns for winwithoutpitching.com "The Fertility Crash Will Make...
Do You Need an Advisory Board? 23.09.2026 16:50
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 09.09.2026 20:34
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...
How Sellable Are You? 26.08.2026 22:14
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 12.08.2026 26:40
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...
Employee Retreats for Remote-First Teams 29.07.2026 20:36
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) 15.07.2026 23:30
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 01.07.2026 20:28
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 17.06.2026 24:45
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 03.06.2026 26:43
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 20.05.2026 20:18
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 06.05.2026 21:41
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...
Three Patterns of Lost Opportunities 22.04.2026 29:24
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 epis...
Why Clients Come, Stay, and Leave 08.04.2026 19:43
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 W...
Is AI Going to Kill Labor-based Pricing? 25.03.2026 27:45
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 Subscri...
If I Were Starting a New Firm 11.03.2026 34:46
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
Decoy or Anchor? 25.02.2026 21:19
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. Links "Decoy or Anchor?" article by Blair Enns for winwithoutpitching.com "The Perils of 'Good/Better/Best' Pricing" 2Bobs episode
We Are All Closet Socialists 11.02.2026 20:03
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. Links "Countering Your 'Central Planning' Tendencies" by David C. Baker for punctuation.c...
Shower Your Way to Sales Success 28.01.2026 20:47
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. LINKS "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 D...
Why Entrepreneurs Are Unemployable 14.01.2026 23:53
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. LINKS "What Makes Entrepreneurs Unemployable" by David C. Baker for punctuation.com
The Problem of Mechanistic Thinking 31.12.2025 20:48
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
Oppositio Singularis: The Positioner's Folly 17.12.2025 13:44
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.
Dealing With the Ghosting Problem 03.12.2025 24:19
Are prospects not responding to your follow-up after you submit a proposal? Blair goes through what might be causing their lack of response and then provides three tools to address the ghosting problem. Links "Ghosted. Now What?" by Blair Enns for winwithoutpitching.com "The Power of a Metaphor" 2Bobs episode Blair's annual 100 Day Sprint post on LinkedIn
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