The Digital Agency Growth Podcast

In this week´s episode Stewart Gandolf joins me to talk through what it actually takes to niche down, build a sustainable agency, and scale without losing your sanity or soul. Stewart’s been in the healthcare marketing game for over two decades, and his experience building Healthcare Success into one of the top firms in the space is loaded with tactical insight.We talk about the trap of project-based work, how to structure your agency around recurring revenue, and why most agencies screw up their first few sales hires.🕒 Timestamps & Topics00:00 — How Stewart got his start and why he doubled down on healthcare03:15 — Direct mail, seminars, and the early version of inbound06:40 — NLP and the psychology behind language that converts11:20 — What drove their early growth (hint: it wasn’t salespeople)13:40 — Why project work is a trap and how to transition to retainers16:00 — Right-sized clients vs. resource-sucking whales18:20 — Inbound vs. outbound: nets, spears, and the bullseye metaphor21:20 — Stewart’s playbook if he were starting from scratch today25:00 — Authority assets: reports, seminars, and content that build trust29:10 — The daisy metaphor and avoiding entrepreneurial distraction31:45 — What most agencies get wrong with their first sales hire37:10 — Traits of a great agency salesperson (and why most don’t have them)40:00 — When to stop being your own best salesperson44:15 — Strategic partnerships and the next wave of AI opportunity47:45 — Final thoughts on staying relevant when the cheese movesA few things we covered.Most agency salespeople fail, not because they’re bad, but because there’s no clear positioning to sell.Links & Resources:🔗 Links & ResourcesHealthcare Success — Stewart’s agencyRelationship Sales at Scale™

Explore the transformative groundwork needed for agency growth as we approach 2025. Learn how to transition from freelancer to enterprise-level with a focus on specialization and strategic planning. Discover why adopting a fresh perspective is key in today's market and how ethical marketing can pave the way for sustainable practices. Embrace innovative client relationship strategies and the power of personalized outreach. Finally, find out how automating lead generation through effective follow-ups can give agency owners more freedom to grow.

Most agencies never crack eight figures. Mark Orttung helped one grow to $130M—by breaking every "safe" rule.In this episode, we dive into what agency owners at the $1–5M mark can actually do to punch past the common growth ceilings.The most important shift?He stopped selling to job titles—and started selling to buyers with something to prove.⏱ Timestamps00:00 – Intro: Why agencies need a rethink00:36 – Mark’s background: Accenture, startups, bill.com, Nexient02:23 – Studying AI in the 90s: symbolic vs neural nets04:30 – Stepping into Nexient at $39M—and losing $5M first06:59 – Early differentiation struggles and customer perception08:29 – Building product-style squads inside a services business10:38 – The big leap: shifting from selling people to selling outcomes11:08 – Simplifying the pitch: “life’s too short for crappy software”13:12 – Saying no to revenue: the scary path to focus14:14 – Selling without data: enterprise outbound as testing lab16:26 – Creating their own conference as a positioning feedback loop19:34 – Cross-industry client base: healthcare to gas utilities to tech20:25 – Specializing by service vs vertical in today’s world24:52 – Growth “walls”: from founder-led to decentralized structure29:21 – Change agents: how to spot internal buyers who take risks32:40 – The next wall at 150M and why he chose to exit36:56 – Getting ghosted on a term sheet, then driving a bidding war40:17 – The Project Works origin story: from spreadsheet to SaaS42:28 – Why every services firm needs better resourcing visibility47:29 – What’s next: proposal automation, AI, and growth tooling48:49 – Where to find Mark and Project WorksKey PointsWhy scaling past the eight figures in a services firm requires breaking the founder bottleneckWhy “life’s too short for crappy software” became a high-converting missionThe opportunity of building or early adopters—not the mainstreamHow to identify and win over internal change agents in large enterprisesHow Project Works helps agencies resource smarter and prevent margin leaksUsing conferences as real-time feedback loops for positioningWhy now is the time to apply AI to services growth ops—especially proposalsLinks & Resources:🔗 Links & Resources🔗 Book a strategy call with Dan: https://salesschema.com/work-with-us/🎙 More episodes of the Digital Agency Growth Podcast: salesschema.com/podcastProject Works – https://www.projectworks.comConnect with Mark on LinkedIn – Mark Orttung

In this episode of the Digital Agency Growth podcast, I’m joined once again by agency advisor Karl Sakas. Karl breaks down the philosophy and practice behind his new book Calm the Chaos—a leadership guide for agency owners who want to scale smart, delegate more, and reclaim time. We also explore his writing process, the parallels between art collecting and running an agency, and how to think clearly when chaos hits your business.⏱️ Timestamps00:00 – Welcome back Karl Sakas + Intro to Calm the Chaos01:09 – Why leadership is the key to scaling a lifestyle agency02:22 – Karl’s writing process05:30 – Blog posts vs. books: Why books matter for positioning07:45 – AI’s role in writing and idea development08:31 – Art collecting vs. agency leadership: Taste vs. discernment13:32 – The tipping point: You can’t be the answer person forever16:13 – The bottleneck around delegation and how to fix it21:50 – What causes chaos in an agency?24:50 – Strong pipeline = better client filtering29:27 – How to delegate growth and not abdicate responsibility34:48 – Should you build demand gen internally or hire it out?37:21 – The M&A market and how to think about valuation and exit41:51 – The real drivers behind agency exits: Age, tuition, and burnout🔗 Book a strategy call with Dan: https://salesschema.com/work-with-us/🎙 More episodes of the Digital Agency Growth Podcast: salesschema.com/podcast🎁 Get a free chapter of Karl’s book: bit.ly/karl-dag

Today, I talk to Todd Gagne—tech founder, startup mentor, and the guy who accidentally dropped a viral bomb on Substack after a weekend rabbit hole about GLP-1 drugs. We talk about why these weight-loss medications might be as transformative as the air conditioner, what this means for advertising, and why the next few years could upend how we think about consumer behavior, even in B2B.⏱️ Timestamps[00:00] – Todd’s background and startup school origins[01:20] – How a Substack detour into GLP-1 changed everything[03:33] – What GLP-1 drugs do, how they work, and why they matter[05:28] – The "air conditioner moment" analogy and downstream societal effects[07:14] – Grocery, alcohol, and aviation: second-order impacts[10:04] – What fills the lifestyle gap?[11:46] – The hidden threat to advertising: fewer impulses, fewer clicks[13:52] – Are your most impulsive ad converters vanishing?[15:15] – Even B2B isn’t safe from this shift[17:22] – Safety data, supply constraints, and the future scale of adoption[19:25] – Could insurance companies lead the charge on GLP-1 coverage?[21:15] – Could 50% of ad strategies go obsolete?[22:23] – Where to follow Todd and dig deeper📢 Key Topics:GLP-1’s societal and psychological impactWhy this isn’t just about weight loss—it’s about impulse controlSecond- and third-order effects on brands, industries, and cultureHow marketing strategies may need to evolve in a post-GLP-1 worldLinks & Resources:Visit: https://salesschema.com/work-with-us/🔗 Learn more about Todd→ https://wildfirelabs.io/

Join Dan Englander and Jared Gibson, co-founder of Outworks, as they dive into the future of B2B marketing and explain why personal branding is the most powerful growth engine for CEOs and founders.Discover why cold outreach is no longer enough, how authentic LinkedIn content can drive long-term trust and authority, and how busy executives can make content creation part of their routine. Jared also shares hands-on tactics for leveraging video and interviews, working smarter with teams, and setting realistic goals for lead generation through personal brands.Timestamps00:00 – Intro & welcoming Jared 01:51 – Jared’s background & launching Outworks 06:43 – Why traditional outbound no longer works 12:46 – How content & algorithms have changed on LinkedIn 18:51 – The importance of knowing your Total Addressable Market 23:35 – Making content creation a lifestyle 29:49 – What ROI looks like on LinkedIn 33:50 – Getting clients comfortable on video 35:21 – Using client interviews for content 37:21 – Jared’s partner program and new service launchTagsLinks & Resources:Visit: https://salesschema.com🔗 Learn more about Jared→ https://www.outworks.io/

Dan dives into innovative outbound strategies tailored for boutique agency owners. He discusses the importance of building trust over chasing leads, highlighting the need for relationship-driven outreach. Key insights include crafting effective copy, the significance of understanding your audience, and how to communicate authentically. Dan emphasizes fostering real connections and the role of timely engagement. He also offers practical tips for scaling outreach while maintaining personal touch, moving away from outdated sales tactics.

In this discussion, Chris DuBois, founder of Dynamic Agency OS and the Snap Offer framework, shares his journey from infantry officer to agency coach. He emphasizes the power of simplifying agency services to enhance clarity and build authority. Chris introduces the one-problem, one-solution model and discusses the PRISM framework for identifying viable market opportunities. Listeners will learn why clarity acts as a sales multiplier, how to create compelling offers that cut through noise, and tackle the real bottleneck: attention.

Join Erik J. Olson, CEO of Proxa and author of 'Million Journey, Dollar', as he shares his innovative path from civil engineering to founding multiple digital agencies. Discover why spinning off agencies can be more beneficial than pivoting, and how to pinpoint the best clients without overcomplicating analytics. Erik discusses the importance of personal engagement in sales strategies and the growing role of AI in agency execution. Learn about the crucial shift from entrepreneur to operator to build a reliable, scalable business.

What separates the agencies that consistently get referrals from those that don’t? According to Audrey Kwan, it comes down to trust equity.In this conversation, Dan Englander talks with Audrey consultant, community builder, and founder of Agency Together about how agencies can get off the feast-or-famine sales rollercoaster by building strategic partnerships, clarifying their niche, and focusing on relationships that compound over time.Topics covered:Why “referral-ready” relationships are built on consistency, not chanceThe ROI of niching for insight, credibility, and collaborationHow small agencies can thrive without growing headcountWhat’s extending sales cycles and how trust shortens them“Growth projects” that drive visibility and long-term differentiationWhy clarity beats diversification, and how to evaluate your niche strategy with SWOT + PESTLEAudrey also shares her “Trust Equity Scorecard,” a free tool that helps agency leaders assess how well-positioned they are to grow through relationships.🔗 Get the scorecard: agencytogether.com/scorecard🎧 Subscribe to The Digital Agency Growth Podcast for more conversations like this, where we cut through gimmicks and focus on what actually drives growth in complex-service businesses.Learn more about The Digitial Agency Growth Podcast at https://www.salesschema.com/podcast/ and our Video training at http://salesschema.com/takecharge CONNECT WITH AUDREY KWAN:LinkedInAgency TogetherAudrey Joy KwanCONNECT WITH DAN ENGLANDER:LinkedInSales Schema