Home Podcasts The Pro Serv Podcast: Grow, Scale, and Exit a Boutique Professional Services Firm
The Pro Serv Podcast: Grow, Scale, and Exit a Boutique Professional Services Firm

The Pro Serv Podcast: Grow, Scale, and Exit a Boutique Professional Services Firm

Collective 54 263 Episodes Oct 8, 2026

This podcast is aimed at owners of boutique professional services firms who want to grow, scale, and eventually exit their businesses. It offers advice and insights on strategic growth, operational scaling, and preparing for a successful sale or transition. Hosted by Collective 54, a community for professional services leaders, the show draws on real-world experience and expert interviews. Listeners can expect practical guidance for building a more valuable and sustainable firm.

Episodes

Erase the Whiteboard: Why New Tools on an Old Process Change Nothing with Miles Kailburn and Jordan Jackson | Episode 276
Erase the Whiteboard: Why New Tools on an Old Process Change Nothing with Miles Kailburn and Jordan Jackson | Episode 276 Oct 8, 2026 1311 Firm Type: Professional services firm | Boutique Professional Services In this episode, Greg Alexander speaks with Miles Kailburn, co-founder and CEO of OTM, about how a professional services firm solved the problem of AI tools producing micro-assistance instead of real transformation. This episode is useful for founders of boutique professional service firms who are working on process redesign, A
Scaling Is Subtraction: What the Founder Has to Stop Doing with Todd Rapp | Episode 275
Scaling Is Subtraction: What the Founder Has to Stop Doing with Todd Rapp | Episode 275 Oct 1, 2026 1342 Firm Type: Professional services firm | Boutique Professional Services In this episode, Jeff Klaumann speaks with Todd Rapp, CEO of Rapp Strategies about how a professional services firm solved the challenge of scaling past the founder. This episode is useful for founders of boutique professional service firms who are working on removing themselves from day-to-day delivery, building a leadership l
Sounding Like Everyone Else: The 4X Marketing Penalty with Lori Turner-Wilson | Episode 274
Sounding Like Everyone Else: The 4X Marketing Penalty with Lori Turner-Wilson | Episode 274 Sep 24, 2026 1282 Firm Type: Professional services firm | Boutique Professional Services In this episode, Jeff Klaumann speaks with Lori Turner-Wilson, founder and CEO of RedRover Marketing about how a professional services firm solved the cost of sounding like everyone else. This episode is useful for founders of boutique professional service firms who are working on differentiating their firm, reducing customer a
Speed Without Clarity Just Breaks Things Faster with Rohan Paul and Derek Lokey | Episode 273
Speed Without Clarity Just Breaks Things Faster with Rohan Paul and Derek Lokey | Episode 273 Sep 17, 2026 1359 Firm Type: Professional services firm | Boutique Professional Services In this episode, Jeff Klaumann speaks with Rohan Paul, President of Teamalytics about how a professional services firm solved the challenge of speed without clarity. This episode is useful for founders of boutique professional service firms who are working on integrating AI into their delivery, protecting their firm's proprieta
Process 101: What a Real SOP Actually Looks Like with Matt Jenkins | Episode 272
Process 101: What a Real SOP Actually Looks Like with Matt Jenkins | Episode 272 Sep 15, 2026 1491 Firm Type: Professional services firm | Boutique Professional Services In this episode, Jeff Klaumann speaks with Matt Jenkins, Founding Partner at Other. about how a professional services firm solved what a real SOP actually looks like. This episode is useful for founders of boutique professional service firms who are working on systematizing delivery, scaling past the founder, and building a fir
Getting Paid for the Outcome: Fixed Fee Plus Success Fee with Charlton Evans | Episode 271
Getting Paid for the Outcome: Fixed Fee Plus Success Fee with Charlton Evans | Episode 271 Sep 8, 2026 1244 Boutique Professional Services | Pro Serv Podcast Pricing is the most-asked-about topic in the membership right now, and most of the conversation stays theoretical. Charlton Evans, CEO of End State Solutions, actually changed his model — and made it work. He moved from a traditional pricing structure to a fixed fee plus success fee, and he did it with real clients, real contracts, and real result
Faster Isn’t a Strategy: Building Something the Client Can Hold with Leo Falkenstein | Episode 270
Faster Isn’t a Strategy: Building Something the Client Can Hold with Leo Falkenstein | Episode 270 Aug 27, 2026 1140 Boutique Professional Services | Pro Serv Podcast Speed has never been cheaper. AI can draft the memo, the deck, the model — in minutes. But fast and useful are not the same thing, and a lot of boutique founders are learning that the hard way. Clients aren't asking for faster anymore. They're asking for something they can hold — a framework they can use, a system they can run, a strategy they can
Building Authority in an AI World with Adam Witty | Episode 269
Building Authority in an AI World with Adam Witty | Episode 269 Aug 19, 2026 1487 In this episode, Jeff Klaumann speaks with Adam Witty, Founder and CEO of Advantage|ForbesBooks, about how boutique professional services firm founders can build authority in an AI world. This episode is useful for founders of boutique professional service firms who are working on differentiating from AI-driven competitors, establishing thought leadership, and using authority marketing to attract
From Margin Crisis to Profitability: The Rebuild with Ravit Gutman | Episode 268
From Margin Crisis to Profitability: The Rebuild with Ravit Gutman | Episode 268 Aug 14, 2026 1942 Finance Transformation Firm | Boutique Professional Services Podcast Most founders discover margin erosion long after it starts, because it never arrives as a single bad decision. It shows up as a discount to win the logo, a hire made ahead of demand, scope that quietly expands. Ravit Gutman of Extropy Advisors watched margin compress across her firm and then did the harder thing: she found where
Hire the Lawyer First: Building the Team That Gets Your Exit Done with Tim Belden| Episode 267
Hire the Lawyer First: Building the Team That Gets Your Exit Done with Tim Belden| Episode 267 Aug 5, 2026 1292 In this episode, Greg Alexander speaks with Tim Belden, a Collective 54 member, about why most boutique founders make a costly sequencing mistake when building their exit team — and what one founder did differently by hiring the transaction attorney before the investment bank. This episode is useful for founders of boutique professional service firms who are preparing for an exit, assembling an ad
Profitable Isn’t the Same as Sellable with Frank Williamson| Episode 266
Profitable Isn’t the Same as Sellable with Frank Williamson| Episode 266 Jul 30, 2026 1426 In this episode, Jeff Klaumann speaks with Frank Williamson, Founder of Oaklyn Consulting, about why a profitable boutique professional services firm is not automatically a sellable one — and what founders must do to close the gap between strong financials and genuine buyer appeal. This episode is useful for founders of boutique professional service firms who are working on preparing for an exit,
Rethinking Service Delivery in the AI Era with Noah Berk| Episode 265
Rethinking Service Delivery in the AI Era with Noah Berk| Episode 265 Jul 23, 2026 1324 In this episode, Greg Alexander speaks with Noah Berk, Co-Founder of Aptitude 8 about how AI is reshaping service delivery and pricing in professional services. This episode is useful for founders of boutique professional service firms who are working on reducing delivery costs with AI, right-sizing their SaaS stack, and navigating the shift from traditional implementation models. Topics covered a

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