Podcast · Business

2Bobs—with David C. Baker and Blair Enns

by David C. Baker and Blair Enns · English · Business

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

New episodes: Every two weeks
Typical length: 24 min
Latest: 7 Oct 2026
Language: English

Latest episode

7 Oct 2026 · 26 min

Get Your Freak On!

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 the World a Small Town" by Tyler Cowen for The Free Press Jesse Ratner's March 27 LinkedIn Post about AI

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Earlier episodes 29 most recent

E251 · 23 Sep 2026 · 17 min
Do You Need an Advisory Board?
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
E250 · 9 Sep 2026 · 21 min
A Proposed AI Contribution Scale
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
E249 · 26 Aug 2026 · 22 min
How Sellable Are You?
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
E248 · 12 Aug 2026 · 27 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
E247 · 29 Jul 2026 · 21 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
E246 · 15 Jul 2026 · 24 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
E245 · 1 Jul 2026 · 20 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
E244 · 17 Jun 2026 · 25 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
E243 · 3 Jun 2026 · 27 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
E242 · 20 May 2026 · 20 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
E241 · 6 May 2026 · 22 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
E240 · 22 Apr 2026 · 29 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
8 Apr 2026 · 20 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
E238 · 25 Mar 2026 · 28 min
Is AI Going to Kill Labor-based Pricing?
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…
E237 · 11 Mar 2026 · 35 min
If I Were Starting a New Firm
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
E236 · 25 Feb 2026 · 21 min
Decoy or Anchor?
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
E235 · 11 Feb 2026 · 20 min
We Are All Closet Socialists
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.com
E234 · 28 Jan 2026 · 21 min
Shower Your Way to Sales Success
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
E233 · 14 Jan 2026 · 24 min
Why Entrepreneurs Are Unemployable
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
E232 · 31 Dec 2025 · 21 min
The Problem of Mechanistic Thinking
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
E231 · 17 Dec 2025 · 14 min
Oppositio Singularis: The Positioner's Folly
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.
E230 · 3 Dec 2025 · 24 min
Dealing With the Ghosting Problem
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
E229 · 19 Nov 2025 · 31 min
Defending the Castle When the Moats Are Drained
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.
E228 · 5 Nov 2025 · 28 min
The Four Priorities of Winning New Business
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. Links "The Only New Business Indicator That Matters" 2Bobs episode "Assume an Advantaged Player" 2Bobs episode "Slapping Down Your Childlike Glee" 2Bobs episode
E227 · 22 Oct 2025 · 25 min
Understanding Earnouts
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
E226 · 8 Oct 2025 · 33 min
Grow or Die?
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. LINKS "Chief Growth Officer" by Blair Enns for winwithoutpitching.com
E225 · 24 Sep 2025 · 21 min
You're Cheating Clients Unless You're Repetitive
David recognizes that the fear of repeating ourselves in our client work is motivated by the right things: "am I delivering value?" LINKS "Repeating Yourself as an Expert" by David C. Baker for punctuation.com "Questions, Not Answers" 2Bobs episode
E224 · 10 Sep 2025 · 30 min
How to Get $500M to Build a Website
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 Recreation.gov
E223 · 27 Aug 2025 · 21 min
When a Key Employee Wants Equity
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.com

About 2Bobs—with David C. Baker and Blair Enns

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

2Bobs—with David C. Baker and Blair Enns is a English business podcast from David C. Baker and Blair Enns. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: David C. Baker and Blair Enns
Language: English
Category: Business
New episodes: Every two weeks
Typical length: 24 min
Latest episode: 7 Oct 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id1219490591

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