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2Bobs in Tuscany

Tuesday, 15 September to Saturday, 20 September 2026

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Blair Enns

Blair Enns is on a mission to change the way creative services are bought and sold the world over. He is the CEO of Win Without Pitching, the sales training and coaching program for creative professionals, and a 25-year veteran of the business side of the advertising and design professions.

He is the author of The Four Conversations: A New Model for Selling Expertise, Pricing Creativity: A Guide to Profit Beyond the Billable Hour, and The Win Without Pitching Manifesto.

David C. Baker

David C. Baker is an author, speaker, and advisor, helping entrepreneurial experts make better business decisions. He’s worked with 1,000+ firms.

His work has been discussed in the Wall Street Journal, USA Today, Fast Company. Inc. Magazine, Forbes, MarketingProfs, and BusinessWeek.

He is the author of Selling Your Professional Service Firm, Secret Tradecraft of Elite Advisors, The Business of Expertise, Managing (Right) for the First Time, and Financial Management of a Marketing Firm.

He was referred to as “The Expert’s Expert” in the NY Times.

Anyone who’s seen the Office Space movie will immediately get the reference for “2 Bobs.” Each of us has been cast as “one of the Bobs” in our work with marketing firms and creatives of all types, so it seemed appropriate to just embrace the connection and extend the inside joke. Milton, the red stapler, TPS reports, and coming to work on Saturday seem wickedly familiar. In each episode, we take turns interviewing each other on a particular theme, for 20-35 minutes. We wander when appropriate, and it’s a bit authentically raw at times, but we want to capture conversations with minimal editing. Both of us love working with entrepreneurial creatives and you’ll see our admiration bleed all over the conversation. You’ll also experience candor, disagreement, and admonition when appropriate.

Website and audio by Marcus dePaula.