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 advisory team for the first time, and looking to protect both the outcome and the economics of the largest financial transaction of their lives. Topics covered are why bringing in the deal attorney first — before the banker — gives founders more control over the exit process, how to evaluate M&A counsel on judgment rather than brand name, and why staying the general contractor throughout the transaction keeps fees in check and protects founder interests from letter of intent to close. Learn more about Collective 54, the community for founders of boutique professional service firms.
Aug 5
21 min
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, understanding what acquirers evaluate beyond revenue and margins, and identifying the operational and structural changes that make a firm attractive to the right buyer. Topics covered are why profitability and sellability are distinct conditions that require different actions to achieve, what sophisticated buyers actually look for when assessing a boutique professional services firm, and the most common sellability gaps founders discover — and how to close them before going to market. Learn more about Collective 54, the community for founders of boutique professional service firms.
Jul 30
23 min
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 are how AI can cut HubSpot implementation costs from over $100K to as little as $10K, the AI sprawl challenge and why governance matters, and whether the SaaSocalypse is real or media hype. Learn more about Collective 54, the community for founders of boutique professional service firms.
Jul 23
22 min
In this episode, Greg Alexander speaks with Ben Edwards, VP of Consulting at CMap about where professional-services software is heading and how AI is changing the way boutique firms access and use their operational data. This episode is useful for founders of boutique professional service firms who are working on modernizing their tech stack, understanding how headless SaaS and MCP access work in practice, and determining which tools are worth keeping as systems of record. Topics covered are what headless SaaS and MCP access mean for a boutique firm, why your PSA and CRM data is an underused asset, and how to evaluate your tech stack when every tool now claims to have AI. Learn more about Collective 54, the community for founders of boutique professional service firms.
Jul 20
30 min
In this episode, Greg Alexander speaks with Peter Kang, Co-Founder of Barrel Holdings about how a boutique agency founder transitioned from owner-operator to pure owner by building a portfolio of specialized agencies. This episode is useful for founders of boutique professional service firms who are working on reducing owner dependence, exploring acquisition as a growth strategy, and building a business that generates durable cash flows without requiring the founder's daily involvement. Topics covered are how to structure a holding company, how to acquire agencies with little to no cash, and what it means to find operators before deals. Learn more about Collective 54, the community for founders of boutique professional service firms.
Jul 6
33 min
In this episode, Greg Alexander speaks with Chris Prinos, founder of Indigo Trigger about how a professional services firm solved building AI leverage without a technical hire. This episode is useful for founders of boutique professional service firms who are working on building AI tools without technical staff, scaling operations without adding headcount, and creating repeatable systems for AI adoption. Topics covered are a repeatable method for building your own AI tools, why clear instructions beat technical skill, and what to hand off to AI and what to keep. Learn more about Collective 54, the community for founders of boutique professional service firms.
Jun 18
17 min
Firm Type: Professional services firm | Boutique Professional Services
In this episode, Greg Alexander speaks with Scott Gardner and Dennis Hahn, co-founders of Liquid Agency about how a professional services firm solved we hired a credentialed m&a advisor. it still went sideways. This episode is useful for founders of boutique professional service firms who are working on preparing for a profitable exit, maximizing enterprise value, and navigating an M&A process. Topics covered are Dennis wish they'd asked before signing, Why a specialist's rolodex can quietly limit your buyer universe, and What 'running a real process' looks like vs. fielding inbound. Learn more about Collective 54, the community for founders of boutique professional service firms.
Jun 4
29 min
Firm Type: Professional services firm | Boutique Professional Services
In this episode, Greg Alexander speaks with Kyle Walbrun, founder of EfficientAide about how a professional services firm solved the january cutoff: rebuilding a services firm around human + ai. This episode is useful for founders of boutique professional service firms who are working on integrating AI into service delivery, building AI-native operations, and transforming pricing and delivery models. Topics covered are Why adding AI to the old delivery model fails, and what a rebuilt human + AI pair actually looks like, How to execute a hard cutoff on new business while transitioning legacy clients without losing the firm, and What changes in recruiting and compensation when AI proficiency becomes the hiring criterion, not EA experience. Learn more about Collective 54, the community for founders of boutique professional service firms.
May 21
23 min
Firm Type: Professional services firm | Boutique Professional Services
In this episode, Greg Alexander speaks with Bart Bartlett, founder of DemandZen about how a professional services firm solved doubling margins in 12 months. This episode is useful for founders of boutique professional service firms who are working on improving firm margins, pricing for profitability, and moving away from cost-plus pricing. Topics covered are How to consolidate spend under a single approval and virtual-card system so every dollar is tracked, categorized, and controllable, The cadence and tooling, and Bart uses to get to a one-day month-end close. Learn more about Collective 54, the community for founders of boutique professional service firms.
May 19
22 min
Firm Type: Professional services firm | Boutique Professional Services
In this episode, Greg Alexander speaks with John Roberson, founder of Advent about how a professional services firm solved the anti-commodity move: winning on experience when ai flattens the work. This episode is useful for founders of boutique professional service firms who are working on integrating AI into service delivery, building AI-native operations, and transforming pricing and delivery models. Topics covered are Why the intangibles, not the deliverable, decide most close-vs-lose proposals, How to replace ''engagement manager plus three'' with named humans, and why that wins deals, and How to package experience as a distinct, premium offering in your proposal, not a throw-in. Learn more about Collective 54, the community for founders of boutique professional service firms.
Apr 24
25 min
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