Should Entrepreneurs Scale Their Business Forever? | Michael Keenan

2 Jun 2026 · 45 min
Episode

2 Jun 2026 · 45 min

0:00

In this episode of The Profitable Creative, host Christian Brim interviews Michael Keenan, founder of Peak Content, a content agency that serves software companies. Keenan recounts his unconventional path from early work‑the‑field jobs and freelance writing on Upwork to building a 50‑freelancer operation that delivers high‑quality, brand‑aligned editorial content at scale. He explains Peak Content’s core value proposition: producing large volumes of content (100‑200 pieces per month) that reads like human‑crafted copy while meeting AI‑driven SEO and brand guidelines, achieved by investing heavily in skilled writers rather than cheap labor. The conversation delves into his philosophy of intentional, limited growth—rejecting endless scaling in favor of a lifestyle‑compatible business, a "wet stone" mindset for handling chaos, and the importance of bringing trusted people along. Keenan shares financial lessons from past ventures, including a failed community platform (Peak Freelance), angel‑investing experiences, and managing an investment and real‑estate portfolio, emphasizing focus on what generates value and cutting distractions. He discusses client acquisition through referrals and low public visibility, the ideal client profile (large, established software firms with internal marketing teams needing scalable content), and pricing via tiered per‑piece models. Throughout, he stresses designing a business that serves personal goals, using meditation and end‑state visualization, and warns against letting a business become the "tail that wags the dog." The episode ends with a brief sponsor spot and calls to action for listeners.

Chapters

More from Christian

48:50
Podcast

Chip Scholz

3mo ago
PodcastLeadership & The Courage to Fail: Kurt Bush
Podcast

Leadership & The Courage to Fail: Kurt Bush

4mo ago
PodcastHow Do You Build a Profitable Marketing Agency? | Lorraine Ball
Podcast

How Do You Build a Profitable Marketing Agency? | Lorraine Ball

4mo ago
PodcastHow Do You Actually Make Money From a Podcast? | Don Vito
Podcast

How Do You Actually Make Money From a Podcast? | Don Vito

4mo ago
PodcastWhy Most Marketing Fails for Service Businesses | Ryan Chute
Podcast

Why Most Marketing Fails for Service Businesses | Ryan Chute

4mo ago
PodcastCreators Gone CAB
Podcast

Creators Gone CAB

4mo ago
PodcastCan You Make Money Doing What You Love? | Kim Slade
Podcast

Can You Make Money Doing What You Love? | Kim Slade

4mo ago
PodcastDoes Direct Mail Marketing Still Work? | Jeff Kruszyna
Podcast

Does Direct Mail Marketing Still Work? | Jeff Kruszyna

4mo ago
PodcastWhy Creators Need to Own Their Audience | Jim Fuhs
Podcast

Why Creators Need to Own Their Audience | Jim Fuhs

4mo ago
PodcastHow Do You Stand Out in a Crowded Market? | Christopher Lochhead
Podcast

How Do You Stand Out in a Crowded Market? | Christopher Lochhead

4mo ago
PodcastHow Do You Turn Podcast Listeners Into Leads? | Nathalie Doremieux
Podcast

How Do You Turn Podcast Listeners Into Leads? | Nathalie Doremieux

4mo ago
See all content