Episode 85: Scaling a Bespoke Agency & Transitioning Into Products, With Brennan Dunn

By Zach Swinehart

Today, Zach’s talking to Brennan Dunn about his various freelance and agency transitions.

If you somehow don’t know who Brennan Dunn is, he’s the dude who started this whole DYF thing. 😅

He started as an employed developer…

Then side hustled as a freelancer…

Until it was doing enough revenue that he quit to go full-time freelance…

And then, through many twists and turns, went on to scale a bespoke-work agency to $2,000,000/yr in revenue with 11 staff…

And later sold his stake in the business to his business partner and successfully made the transition into products, while still taking on occasional high-ticket consulting gigs.

…But you already probably know all this.

After all, he’s Brennan freakin’ Dunn!

In this interview, Zach picks Brennan’s brain about a “day in the life” of running a scaled bespoke agency, and did some comparisons about the different lifestyle consequences of his 4 different paths of experience:

  • Running a 7-figure bespoke agency
  • Running a SaaS business (aka Rightmessage, Palladio)
  • Running an education product business (aka DYF, Create & Sell)
  • Running a highly-leveraged solo consultancy (i.e. his email personalization + funnel consulting engagements for SPI et al)

AI-Generated Summary:

  • 0:00 – 2:00 — Zach introduces Brennan to discuss transitioning from running an agency to software products. Zach questions managing many ventures at once.
  • 2:00 – 4:00 — Brennan provides a background about himself, speaks about past podcasts, and introduces Zach’s involvement. Discusses trying to juggle many projects and finding a successor in Zach.
  • 4:00 – 6:00 — Zach sets the stage for the interview, focusing on business choices based on values and goals. Brennan begins discussing the foundation of his agency, “We Are Titans.”
  • 6:00 – 8:00 — Brennan details the growth of his company, transitioning from freelance to a brick-and-mortar setup, and the challenges of intentional client acquisition.
  • 8:00 – 10:00 — Brennan’s shift towards online courses and desire for passive income sources. He narrates handing over his agency and establishing another company, Plan Scope. Brennan concludes by tracing back to his current endeavors.
  • 10:00 – 12:00 — Zach expresses his interest in Brennan’s product businesses and seeks to focus on bespoke agency benefits compared to product-based businesses. Brennan clarifies a past association with Pat Flynn.
  • 12:00 – 14:00 — Brennan recounts the inception of his book “Double Your Freelancing Rate” and touches on early attempts at email marketing. He highlights experiences working with various software companies.
  • 14:00 – 16:00 — Zach outlines the flow of the interview and emphasizes the core aspect of helping listeners decide on the right business structure. He probes Brennan on what makes a business suitable for certain individuals.
  • 16:00 – 18:00 — Brennan touches on tailoring his introduction at networking events based on the audience and describes how he positioned “We Are Titans” in different settings.
  • 18:00 – 20:00 — Brennan further describes the value proposition of “We Are Titans” for local businesses, emphasizing custom software solutions tailored to specific workflows.
  • 20:00 – 22:00 — Brennan discusses their fondness for innovative projects like social networks. Zach and Brennan delve into the evolution of business tools, emphasizing the shift from custom software to no-code solutions.
  • 22:00 – 24:00 — Zach highlights the value Brennan brought to businesses, making processes more efficient. Brennan shares his networking strategies, like local events and building a mailing list.
  • 24:00 – 26:00 — Brennan elaborates on their local marketing initiatives and how they used events to build relationships. He also mentions how networking led to global client opportunities.
  • 26:00 – 28:00 — Brennan highlights the value of building an army of referral partners. Zach asks for modern equivalents of Brennan’s networking tactics. Brennan points to community-building in current online spaces.
  • 28:00 – 30:00 — Brennan speaks on establishing authority in personalized marketing. He emphasizes the importance of curating and reshaping information for a specific audience and points out effective methods used by modern online creators.
  • 30:00 – 32:00 — Brennan details how public data insights bolstered Chanel’s reputation in the community, making her a known expert. He also references Sam Hewitt’s critiques of user onboarding processes, adding value by publicly sharing expertise.
  • 32:00 – 34:00 — Brennan emphasizes the importance of networking and hands-on experience in understanding and communicating with clients. Zach ties the discussion to the current year, pointing out that the principles remain relevant in 2023.
  • 34:00 – 36:00 — Zach ponders the challenge of initiating Trojan horse conversations without an existing audience and praises the method of analyzing and sharing industry best practices.
  • 36:00 – 38:00 — Brennan recalls the transition from hourly billing to a team-based package approach at his agency, providing clients with a mix of developers, designers, and project management for a set weekly fee.
  • 38:00 – 40:00 — The agency utilized Pivotal Tracker to manage task priorities and determine project timelines based on weekly output. Brennan emphasizes the shift from hourly specifics to delivering value within weekly iterations.
  • 40:00 – 42:00 — Zach references Brennan’s insight on pricing strategy; Brennan explains the structure of his agency’s team and highlights that payroll was their most significant expense.
  • 42:00 – 44:00 — Brennan dives into the agency’s revenue and expenses, including project costs like flying to Tokyo. Zach focuses on the profits Brennan managed to secure.
  • 44:00 – 46:00 — The conversation steers towards the source of the agency’s clients, emphasizing the importance of referrals from an intentionally built network.
  • 46:00 – 48:00 — Zach begins to shift the discussion towards the phases of Brennan’s entrepreneurial journey, setting up a transition to a visual aid.
  • 48:00 – 50:00 — Zach elaborates on the flowchart, outlining the typical progression of someone from employee to freelancer to agency or product business owner.
  • 50:00 – 52:00 — Zach discusses business growth, and Brennan explains his early roles and introduction to Ruby on Rails.
  • 52:00 – 54:00 — Brennan talks about a startup he began for mortgage lead generation and its collapse due to the 2008 financial crisis.
  • 54:00 – 56:00 — Brennan describes transitioning from freelance to establishing an agency, emphasizing the differences in costs and commitments.
  • 56:00 – 58:00 — Brennan underlines the importance of having a consistent work pipeline and networking in mastermind communities for business growth.
  • 58:00 – 60:00 — Zach points out the common mistake of prematurely jumping into agency models without steady lead flow, emphasizing the importance of establishing consistent leads before scaling.
  • 1:00:00 – 1:02:00 — Zach questions Brennan’s motivations behind decisions, with Brennan revealing mistakes and his lack of recurring revenue in the agency; Brennan also touches on the inception of “Planscope”.
  • 1:02:00 – 1:04:00 — Discussion about transitioning from agencies to software and info products; Zach references a conversation with Jesse, and Brennan elaborates on the challenges of creating software tools.
  • 1:04:00 – 1:06:00 — Zach highlights Brennan’s varied experiences and the value they bring when hiring for a SaaS company; Brennan concurs, emphasizing the importance of diverse business experiences.
  • 1:06:00 – 1:08:00 — The conversation delves into the sequential transitions of Brennan’s businesses, from “Planscope” to “Double Your Freelancing” to “RightMessage”.
  • 1:08:00 – 1:10:00 — Brennan explains the inspiration behind “Create and Sell” as a response to a perceived stagnation in “RightMessage” and how it unintentionally aligned with his book deal.
  • 1:10:00 – 1:12:00 — Brennan shares the origin story of “Right Message,” revealing it came from a CEO’s suggestion and a funding opportunity; he touches on initial challenges and the differences in content marketing between “Right Message” and “Double Your Freelancing.”
  • 1:12:00 – 1:14:00 — Brennan discusses merging “Right Message” with “Create and Sell,” suggesting that the latter prepares people for the former; Zach shares a similar business model from a client.
  • 1:14:00 – 1:16:00 — Zach praises Brennan’s problem-solving approach; Brennan recalls custom JavaScript tweaks which led to new solutions and emphasizes his continuous learning from past experiences.
  • 1:16:00 – 1:18:00 — Brennan reveals his vision of an ideal business: one with minimal meetings, lots of deep work, and active feedback from customers; he fondly recalls his agency days with big client deals.
  • 1:18:00 – 1:20:00 — Brennan expresses his appreciation for the predictable revenue from numerous small customers, highlighting the freedom and lack of dependency it offers; he also emphasizes the fulfillment derived from positively impacting others.
  • 1:20:00 – 1:22:00 — Brennan discusses the importance of feeling he’s making a positive impact with his work and admits he couldn’t thrive just chasing profit without positive feedback; Zach shares his struggle in feeling a direct impact with his clients.
  • 1:22:00 – 1:24:00 — Brennan acknowledges the contrasting feedback he gets: while positive emails uplift him, there’s a vocal minority that can be demotivating; he also differentiates the responses he gets as a newsletter writer versus a tool vendor.
  • 1:24:00 – 1:26:00 — Zach and Brennan discuss the concept of business as a video game, and Zach points out the differences in fulfillment between solo and product-based businesses.
  • 1:26:00 – 1:28:00 — Brennan reflects on his previous aspirations of being a business traveler, comparing his past and present motivations; he once romanticized international business but now prioritizes impactful work with minimal involvement.
  • 1:28:00 – 1:30:00 — Brennan expresses his appreciation for having established systems that generate income from past work, moving away from a transactional model; he also mentions his friend Nick’s unique business model.
  • 1:30:00 – 1:32:00 — Brennan describes Nick’s innovative approach to productizing services, emphasizing the importance of selling time as a product, and how this equips freelancers with the skills necessary to create successful products.
  • 1:32:00 – 1:34:00 — Zach considers the advantages of productized services in building business skills, while Brennan reflects on the challenges he faced with a bespoke agency and the allure of passive income.
  • 1:34:00 – 1:36:00 — Brennan shares his new venture of establishing an agency and differentiates it from his previous experiences by eliminating his role as a dependency in its operation.
  • 1:36:00 – 1:38:00 — Discussing successful agency models, Brennan cites the example of Nathan Berry venturing into an email newsletter agency despite already running a major email marketing platform.
  • 1:38:00 – 1:40:00 — Brennan elaborates on the potential lucrative nature of agencies with good systems, contrasts sweatshop-like operations with systematic approaches, and shares his experiences in road mapping to ensure project clarity and success.
  • 1:40:00 – 1:42:00 — Brennan highlights the value of understanding business problems beyond just delivering code, while Zach emphasizes the advantages of hands-on services and feedback when launching a product.
  • 1:42:00 – 1:44:00 — Brennan shares the benefits of an immediate cash flow in bespoke agencies and the ease of reaching financial targets with fewer clients as opposed to multiple subscribers in SaaS.
  • 1:44:00 – 1:46:00 — Emphasis on direct one-on-one sales interactions and the skills and insights derived from pushback and direct conversations with clients.
  • 1:46:00 – 1:48:00 — Zach and Brennan discuss the pros and cons of direct client interactions versus automated processes. They touch upon the missed opportunities when skipping direct feedback and sales rejections.
  • 1:48:00 – 1:50:00 — Brennan elaborates on his journey from consulting to workshops and finally to creating courses, emphasizing the importance of live interactions and understanding problems deeply before building solutions.
  • 1:50:00 – 1:52:00 — Brennan discusses the initial challenges with onboarding users to Churn Muster and how observing users helped improve the process. Zach introduces the concept of scaffolding and its premature implementation.
  • 1:52:00 – 1:54:00 — Brennan shares an example of manual service mimicking software. They then discuss the benefits of having a recurring revenue model and the challenge of transitioning from project-based work to a retainer model.
  • 1:54:00 – 1:56:00 — Brennan highlights the changing nature of technical requirements, mentioning the rise of no-code solutions. Zach inquires about the importance of owning the lead flow and Brennan mentions his course.
  • 1:56:00 – 1:58:00 — Brennan emphasizes that professional roles and strategies can evolve over time and that there’s no permanent designation. He also acknowledges personal challenges with direct sales for Right Message.
  • 1:58:00 – 2:02:00 — Brennan clarifies that his current challenge is with outreach, not sales calls. Zach recommends documented outreach strategies and Brennan details his plan for targeted outreach using prospecting tools.