2Bobs—with David C. Baker and Blair Enns
Conversations on the art of creative entrepreneurship with David C. Baker and Blair Enns. The podcast covers topics related to running a creative business, including strategy, pricing, and client relationships.
Episodes
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
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
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'" b
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
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
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
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
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
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
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
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
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
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 epis
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 W
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 Subscri
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
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
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.c
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 D
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
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
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.
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
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.
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
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
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
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
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
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
SpamHack Your Way to Growth!
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.
What I Learned From Teaching Motorcycle Racing
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
A DIY New Business System
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. LINKS "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?"
Dealing With Today's Employee
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
There Is No Credential Meeting
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
The Waterfall of Differentiation
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).
Always Be Anchoring
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.com
What to Ask, Sign, and Share With a Potential Buyer
Following up on the recent episode on whether you should be considering that offer to sell your firm, David provides four questions to get answered, two documents to sign, and a short list of materials that can help you take the lead in early conversations with a buyer. LINKS "Should You Entertain That Acquisition Offer?"
The Power of a Metaphor
The more unexpected the metaphor, the more information it carries. Blair has four less-obvious metaphors to give you access to entire playbooks in just four words when selling your expertise. LINKS "The Power of a Metaphor" written by Blair Enns for winwithoutpitching.com
Should You Entertain That Acquisition Offer?
Ignoring any unexpected offers to buy your business that might come your way is not in your best interest. But neither is dating all opportunities in desperation. David has four things principals should consider, whether or not you are actively looking to sell your firm. Links "Should You Entertain That Offer?" by David C. Baker for punctuation.com 2Bobs London Meet-up on Thursday 8 May, 2025 at
When Your Clients Talk to Each Other
Your clients are far more likely to talk to each other when you have vertical positioning. Blair has observed both good and bad things arising from this. Links "How to Ask for Referrals" 2Bobs episode
Facing an Existential Crisis?
As we are hearing about more firms that are closing during these challenging times, David offers some guidance to help cut through the confusion when our worst fears in our business become reality. Links "Facing an Existential Crisis" article by David for punctuation.com Rory Sutherland's LinkedIn post David's LinkedIn post
Who Should Set Prices?
As Blair continues to encourage expert practice owners to price the client and not the service, he and David discuss the pros and cons of four levels of pricing authority they should be thinking about within their firm, instead of just assuming pricing responsibility automatically defaults to a specific role or job title. Links "Who Should Set Prices In Your Firm?" written by Blair Enns for WinWi
10 Reasons a Buyer Might Want Your Firm
David thinks principals should build their firms as if they were going to sell it while Blair's advice is to run it as if you'll never sell it. Being aware of options as your firm matures can give you the leverage you might need in negotiations. Links "Ten Reasons Firms Are Bought" by David C. Baker for punctuation.com
To Standardize or Customize
Through the process of writing his latest book, Blair's thinking has evolved on whether or not firms should resist the urge to productize their services as they work to creatively meet the unique needs of each client.
Don't Bother Eating Your Veggies
In Blair's experience, the most common reason a lead generation plan doesn't get executed is it doesn't recognize and leverage the strengths or motivations of the individuals executing. LINKS "The Best Lead Generation Plan" article by Blair Enns for WinWithoutPitching.com "The Rungs You Can Reach on the Ladder of Lead Generation" 2Bobs episode
Adapting Hiring Strategies Over Time
David describes the differences in what kind of people principals should hire during the early stage of their creative firm's development when it's all about "what we can afford," the middle stage when it's about "what we need," and then the later days of an agency when it's about "what we can learn." LINKS "How Your Hiring Strategies Change" by David C. Baker for punctuation.com "The Problem of
The Barbell of Pricing Risk
Blair borrows a concept from finance and fitness to help creative agencies find the balance between low risk and high risk pricing strategies.
Selling Your Professional Services Firm
Blair interviews David about his new book, Selling Your Professional Services Firm: A Primer. LINKS Buy a copy of David's new book from him directly. Buy David's new book and audiobook on Amazon.
Questions, Not Answers
Blair interviews David on his recent article about the idea that expertise does involve supplying answers, eventually, but mainly expertise is about asking the right questions, first, and then offering a few answers after the truth surfaces. Links "Expertise Is Mainly About Asking Great Questions" by David C. Baker on Punctuation.com
Assume an Advantaged Player
Blair shares how to determine whether or not we are the advantaged player the "polite battle for control" within the game of sales, and how we can get the odds of winning the sale to be more in our favor. Links "Assume an Advantaged Player" article by Blair Enns on WinWithoutPitching.com
The Four Conversations: A New Model for Selling Expertise
David interviews Blair about his new book, which lays out his proven framework B2B service providers can use to increase closing ratios and average proposal values. Links Order The Four Conversations: A New Model for Selling Expertise by Blair Enns
200th Episode Special
Blair and David reminisce about their podcasting journey since Blair first pitched the 2Bobs idea to David back in 2016, sharing what they've learned along the way, and what they might like to try with the podcast in the future.
How Account Managers Deliver Strategy
David unpacks six principles that can help creative firms benefit from delivering strategic guidance through their account managers. LINKS "Account Managers and Strategy" by David C. Baker at punctuation.com
How to Avoid Commodifying Your Offering
Blair sees four common behaviors when business owners are looking to get deals moving in times of economic decline, stagnation, or uncertainty that end up doing long term harm to their positioning and pricing. LINKS "Four Ways to Commodify Your Offering" by Blair Enns on WinWithoutPitching.com "Phase Your Client Engagements" 2Bobs episode
Are Email Newsletter Even Viable Anymore?
Every few years we're told that we need to move on from using email newsletters as a part of our marketing platform. And David says that advice has always been wrong. Links David's article on Punctuation.com (subscribe to his newsletter at the bottom of the page) "Email is the Most Consistent, Reliable Marketing Channel on the Web and I Can Prove It" by Rand Fishkin
How to Make Horizontal Positioning Work
David provides some clear examples of what is required for a firm to be successful at offering one service for many different verticals. Links "Strengthening a Weak Horizontal Positioning" by David C. Baker on punctuation.com
Are You Fishing in the Right Pond?
Given these uncertain economic times we are in right now, Blair is asking if some creative firms might need to rethink the market they serve, looking at whether their positioning might be too broad, too narrow, or just wrong. LINKS "The Target Is Not the Market" by Blair Enns on winwithoutpitching.com
Leading in a Chaotic World
David shares his decision-making framework that will help agency principals make better decisions during chaotic times like these. LINKS "Leading in a Chaotic World" article by David C. Baker on Punctuation.com
Creating a Premium Pricing Culture
Pricing is a prison cell of our own making. And it's cultural. Blair has come up with a series of prompts as a creative exercise to help us all move into a realm of higher pricing. Links "Creating a Culture of Premium Pricing" by Blair Enns at WinWithoutPitching.com "Have we Hit Peak Strategy?" "Be the Client You Want to See in the World"
Building a Scalable Sales Strategy
David wants agency principals to develop new business plans which delivers more new leads with less labor so their organizations can have more controllable growth, as well as increasing their likelihood for a successful exit when that time comes. Links 2Bobs episode: "The Rungs You Can Reach on the Ladder of Lead Generation" NY Times article: "How a Self-Published Book Broke 'All the Rules' and
Have We Hit Peak Strategy?
Blair thinks too many design firms and other service providers are trying too hard to raise prices by presenting themselves as more "strategic." Both he and David see these agencies losing more and more work to competitors moving to off-shore teams and AI centered services. Links Blair's "What Is Strategy?" episode of the Ditching Hourly podcast with Jonathan Stark
What Tech Bros Get Right...and Wrong
David definitely doesn't want anyone to be like tech bros, but he has recognized a few things creative agencies might be able to learn from them.
Turning Your Delivery Team Into a Sales Team
Blair has five steps creative agency leaders can take to turn their account managers, project managers, developers, engineers, and advisors into a source of instant scale to their sales efforts. LINKS "Turning Your Delivery Team Into a Sales Team" article by Blair on WinWithoutPitching.com
Advising Clients Ethically
Whether you call yourself an advisor or consultant (or not), David has seven core ethical principles that should govern advisory work. LINKS "Advising Clients Ethically" article on Punctuation.com
Just Stop Talking
The fact that sales people tend to talk too much is nothing new, but Blair has observed in recent client work just how profound of an effect this pervasive problem has on sales outcomes. Links "How and When to Talk About Your Firm" "Replacing Presentations With Conversations"
Working With a Maverick
When it comes to qualifications for ideal clients, David doesn't hear anyone talking about how agencies can benefit when the person across the table is someone who presses boundaries and ethically skirts the rules within their own organization.
The Dichotomy of the Expert Salesperson
As Blair is finishing his new book that drops later this year, he comes to the realization that pretty much everything he does comes down to the fundamental issue that experts think they need to show up as a different person during the sale: pitching, persuading, and convincing instead of as the leader their prospective clients need them to be. LINKS "The Dichotomy of the Expert Salesperson" art
Maximizing Pro Bono Opportunities
While discussing eight ways creative firms can do pro bono work better based on an article David wrote recently, both he and Blair discover a couple new profound insights together. LINKS "Maximizing Your Pro-Bono Contributions" by David C. Baker at Punctuation.com Left-handed Mango Chutney
Attending the Way
Blair recognizes how a Confucius quote is really bad business advice, but is still moved by how a highly principled creative firm in New Zealand continues to thrive by prioritizing their creative practices and client fit over new business strategy. LINKS "Attending the Way" article by Blair on WinWithoutPitching.com AltGroup.net
A 7-part Theory of Principal Compensation
David frequently gets hired to help resolve issues at firms between multiple principles when it comes to who does what and how much each should get paid, so he's come up with a 7-point framework he can use in each unique scenario.
The Time Value of Knowledge
David interviews Blair about his recent article in which he takes a lesson from investing with compound interest to understand the increasing returns we can receive from our relentless pursuit of knowledge over time. Links "The Time Value of Knowledge" article on WinWithoutPitching.com
Revisiting Remote Work
David looks at the current data and weighs all the pros and cons of continuing to have staff who work from home in our post-pandemic economy, which makes Blair wonder if he would even survive if he was starting out in his profession today. Links "The Pros/Cons of Remote Work"
Ditch the (Sales) Script
Blair sees too many creative firms talking at prospective clients using sales scripts instead of having a series of wide ranging conversations on their unique issues and objectives that set the tone for the potential long-term engagement. Links "Ten Set Pieces" "Mastering the Value Conversation"
Constrained by Artificial Boundaries
Blair's latest obsession is bounded rationality, in which he sees too many creative firms failing to make "rational" decisions because they choose to bind their businesses with outdated and overly-constraining ideals like the 80/20 principle. Links "The Great Convergence is Upon Us" by Blair Enns for Win Without Pitching Award-winning "Unapologetically Human" ad campaign by Kruger and BHLA Produ
A Theory of Leisure
David shares his thoughts on some bad advice he hears involving the focus on pursuing personal passions in business.
The Death Throes of the Pitch
Blair weighs in on this year's Forrester report, which shows the ridiculous amount of money agencies have been wasting on pitches. LINKS "Are These the Last Days of the Pitch?" by Blair Enns for Win Without Pitching "A New Forrester Report Urges Brands and Agencies to 'Ditch the Pitch'" by Olivia Morley for AdWeek published on 4 A's
How Much Should You Spend on Your Own Marketing?
David addresses another frequently asked question, looking at what creative firms should budget in terms of both money and time for their website, SaaS/automation, PR, content creation, and social media.
The Conflicting Ethics of Selling and Negotiating
Blair identifies the differences between the ethics of selling expertise and the three schools of bargaining ethics, and what happens when we don't adapt our bargaining approach to match our opponents in the game of negotiation. Links "The Conflicting Ethics of Selling & Negotiating" article by Blair Enns on WinWithoutPitching.com
Doing Employee Orientation Right
In an era of rapid turnover and remote working arrangements, developing a structured onboarding process for new staff is more important than ever. David has a checklist to help agencies get their new employees up to speed as quickly as possible.
