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

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 'C...

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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 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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December 3, 2025 24 mins

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

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One characteristic of our industry is disappearing moats. After a brief overview of the fourteen moats we've lost from 1965 to today, we'll look at what turf we really have left to defend and what the future will look like if we get this right. It'll be very different, and you'd better get ahead of it.

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What do we do in those situations where we have to pitch? Blair simplifies some important principles from his books into a sequence of four precepts we can follow when the sales process doesn't progress like we'd hoped.

 

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"The Only New Business Indicator That Matters" 2Bobs episode

"Assume an Advantaged Player" 2Bobs...

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October 22, 2025 25 mins

If/when you sell your firm, it'll likely be the largest transaction of your life, and so it makes sense to understand it! In this episode David gives a crash course in everything earnouts.

 

LINKS

"Understanding Earnouts" by David C. Baker for punctuation.com

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October 8, 2025 32 mins

Blair recognizes growth opportunities in every area of life and business, yet sees many people chasing metrics while unknowingly resisting genuine progress for various reasons.

 

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"Chief Growth Officer" by Blair Enns for winwithoutpitching.com

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David recognizes that the fear of repeating ourselves in our client work is motivated by the right things: "am I delivering value?"

 

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"Repeating Yourself as an Expert" by David C. Baker for punctuation.com

"Questions, Not Answers" 2Bobs episode

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September 10, 2025 30 mins

Blair tells the story of recreation.gov and how its performance pay deal has been nothing but wins for every party involved, with plenty of lessons for buyers and sellers of all kinds of services.

 

LINKS

"Performance Pay Leads to a $500M Website" by Blair Enns for winwithoutpitching.com

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August 27, 2025 21 mins

David provides a framework for one of the most important conversations in a creative agency principal's life.

 

LINKS

"When A Key Employee Wants Equity" by David C. Baker for punctuation.com

"Pros + Cons of Having a Partner" by David C. Baker for punctuation.c...

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August 13, 2025 19 mins

Instead of railing against AI-generated spam, Blair decides to "get in on the action" with his brand new SpamHack AI Growth System™️ in this spoof episode.

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David recognizes more than a few parallels between his passion for motorcycle racing and the work being done in creative and marketing agencies.

 

LINKS

"What I Learned from the Race Track" by David C. Baker for punctuation.com

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July 16, 2025 33 mins

Instead of just relying on the talent of individual sales people, Blair recommends creative agencies identify and invest in six elements as a part of their organization's long-term sales system.

 

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"Critical Questions Your New Business Person Should Be Able to Answer" 2Bobs episode

"How to Ask for Referrals" 2Bobs episode

"CRM and the Mistakes to Avoid" 2Bobs episode

"Who Should Set Prices?" 2Bobs episode

"Mastering the Value ...

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July 2, 2025 24 mins

David finds the courage to address a topic he's been putting off for awhile, as he is seeing more agency principals struggling to maintain both healthy and productive work environments by leading the ongoing process of resolving tensions within their teams.

 

LINKS

"Adapting to a Modern Workforce" by David C. Baker for punctuation.com

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June 18, 2025 30 mins

Instead of beginning the relationship with a prospective client by presenting a deck on why your agency is so amazing and why you should be invited to pitch, Blair encourages us to have the "Probative Conversation" from his Four Conversations sales model.

 

LINKS

"There Is No Credentials Meeting" article by Blair Enns for WinWithoutPitching.com

"The Four Conversations: A New Model for Selling Expe...

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June 4, 2025 27 mins

When it comes to positioning, David is still seeing creative firms failing to answer three essential questions in the proper sequence: category, specialization, and then secondary differentiators (or qualifying characteristics).

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May 21, 2025 30 mins

Blair sees high price anchors everywhere—from buying a suit to ordering a burger. So what factors should creative firms keep in mind as they use anchoring in selling their service options? And when is the best time to present the anchor option within the sales conversation?

 

Links

"Anchor High" by Blair Enns for winwithoutpitching.co...

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