Agency Journey - Behind the Scenes of an Agency Business

Agency Journey is a monthly series that details the happenings at my agency Barrel, founded in 2006. I also share what’s happening at our other agency businesses under the Barrel Holdings umbrella.

Below are past episodes along with the topics covered in each.

Agency Journey Episode 57 (Y18M12), May 2025

Unlocking the Value of an Old Inbox
A Variety of Deal Flow & How We Categorize
Mid-Quarter Check-ins
BX Studio on a Roll, Doubling Down on Sales
Portfolio Management: Thinking About Underperformance, Opportunity Cost, & Capital Allocation

Agency Journey Episode 56 (Y18M11), April 2025

AI Tools Replacing Agencies
HoldCo Conference
Quarterly Leadership Summit
Deal Under LOI
“Compensation is Our Way of Speaking to Employees”

Agency Journey Episode 55 (Y18M10), March 2025

Barrel Holdings Rebrand Coming Soon
Navigating Margins vs. Client Satisfaction at Bolster
Deal Flow Via LinkedIn
Finally Driving Some Revenue with AgencyHabits
Learnings & Realizations Via M&A Convos

Agency Journey Episode 54 (Y18M9), February 2025

Barrel CPG Positioning & Expo West
SuperFriendly Launch
Catalog Bounces Back
We Haven’t Cracked the Lead Gen Problem

Agency Journey Episode 53 (Y18M8), January 2025

Feels Like the Early Days Again / Exploring Possibilities
Q1 2025 Barrel Holdings Quarterly Meeting
A Few Different Investments: Coaching/Consulting/AI
Margin of Safety and Agency Venture Studio

Agency Journey Episode 52 (Y18M7), December 2024

A Year of Big Changes
Strong Signs for Barrel Heading into 2025
Prima Mode’s Slow Start & Refined Positioning
Catalog’s Struggles & Experiments
Further Refining the Barrel Holdings Vision

Agency Journey Episode 51 (Y18M6), November 2024

A Note of Gratitude for This Year’s Developments
Recruiting a PM Lead for BX Studio
Net Revenue Retention and Agency Growth
Exploring Marketing Investments for Next Year
Evolving Thoughts on Acquisition Targets

Agency Journey Episode 50 (Y18M5), October 2024

AgencyHabits: Launch and Why We’re Doing It
Attending BubbleCon
Q4 2024 Barrel Holdings Quarterly Meeting
Agency Sales and Marketing: How Much to Invest

Agency Journey Episode 49 (Y18M4), September 2024

Presenting to Private Equity Portfolio Companies
BX Studio Momentum & Growing Pains
Catalog’s Churn Challenge
Bolster’s Breakout Quarter
Cost Discipline and Cost Advantage

Agency Journey Episode 48 (Y18M3), August 2024

Still Taking Some New Biz Calls
Catalog Gets a New CEO
Launching Prima Mode, Our Amazon Agency
Outlook for Barrel Improves
Getting Clear on the Barrel Holdings Growth Strategy

Agency Journey Episode 47 (Y18M2), July 2024

Our First Acquisition
Last Barrel Leadership Book Club
Q3 Barrel Holdings Quarterly Meeting
Webflow Partner Summit in Toronto
Hiring a New CEO

Agency Journey Episode 46 (Y18M1), June 2024

The Barrel CEO transition & What I’ll Be Writing About Moving Forward
Early Progress in Barrel’s New Approach to Selling Services
Our Partnership with Contra
80 Omakase Engagements Later, What It Means for Bolster
Growing the Portfolio of Agencies

Agency Journey Episode 45 (Y17M12), May 2024

Enjoying R&R
Revenue Booking Struggles Continue
Shifting Away from Selling Hours
The Road to Avoiding Commoditization

Agency Journey Episode 44 (Y17M11), April 2024

Moving Out of 197 Grand, Barrel’s Office For Nearly 13 Years
Slow Start to the Quarter
Our Continued Search for a Sales Lead
Partners Book Club
Barrel Holdings Q1 2024 Updates
The Need to Meet in Person

Agency Journey Episode 43 (Y17M10), March 2024

Posting on LinkedIn Update
New Business Wins to Close Out Q1
Getting Organized With a 1-Page Report
Bolster: Going All In On the Offer
Looking for a Sales Lead

Agency Journey Episode 42 (Y17M9), February 2024

Taking Inspiration from Walt Disney
Positioning and Marketing Around CPG Food & Bev
Potential Acquisitions for Barrel
Simplifying Our Ongoing Offering Across the HoldCo
Talent, Talent, Talent

Agency Journey Episode 41 (Y17M8), January 2024

The Swings Between Sales & Marketing and Recruiting
Riding the Pipeline Rollercoaster
New Barrel Website Launch
HoldCo Momentum
Sales and Marketing Approach This Year

Agency Journey Episode 40 (Y17M7), December 2023

Lessons That Helped Us Stay Focused This Year
Some Wins Heading Into New Year
Org Structure Changes: PMs to Software Team
Activity at Bolster, BX, and Vaulted Oak
Goal Setting for Next Year

Agency Journey Episode 39 (Y17M6), November 2023

Life is Fleeting, Being Grateful (a Thanksgiving note)
Account Planning for 2024
A Sizable Client Going Away
Some Wins, Some Losses, and a Couple of Launches
Present Needs vs. Building For The Future

Agency Journey Episode 38 (Y17M5), October 2023

Partner Book Club & Barrel Holdings Meeting
Attending Conferences: Shopify Partner Summit, Webflow Conference, and ChargeUp
Barrel Retreat 2023
Lots of New Biz Activity But Long Sales Cycles
Overcoming the Fear of Rejection & What That Enables

Agency Journey Episode 37 (Y17M4), September 2023

Business Thoughts During Parental Leave
Falling Short on Revenue Goals, Rounding Out 2023
Leads Analysis Takeaways
Examining Our Business Model

Agency Journey Episode 36 (Y17M3), August 2023

Moving Upstate & Out of Brooklyn
Small Deals, But Wins Nonetheless
Building Momentum with Bolster
Drilling Down Deeper Into the Business

Agency Journey Episode 35 (Y17M2), July 2023

Spain Vacation & Working in Europe Time Zone
Celebrating Lucas’s 10 Years at Barrel
A Couple of Client Website Launches, Opportunity to Improve Content Experience for Clients
Barrel Holdings: BX Studio and Vaulted Oak Continue Their Growth
Rethinking Agency Marketing

Agency Journey Episode 34 (Y17M1), June 2023

Briefly Celebrating 17 Years
Outbound Lead Generation Update
New Business Wins & A Major Launch
Ecommerce Agency Summit in Toronto
Ongoing Commitment to Continuous Improvement

Agency Journey Episode 33 (Y16M12), May 2023

New Business Wins (Finally)
Getting Results Through Networking
Attending a Couple of Conferences
Solidifying Bolster’s Offering
“Culture is an Output, Not an Input”

Agency Journey Episode 32 (Y16M11), April 2023

The Nice Thing About Having Agency Friends
Slow Month of New Biz Wins
Trying Another Outbound Firm
Vaulted Oak and BX Studio Showing Strong Results
A New Site Launch and the Importance of Returning Clients

Agency Journey Episode 31 (Y16M10), March 2023

Our Roam Trial & Too Much Software
Business Development Reset
Attrition and Hiring
Wins & Losses and a Couple of Launches
ChatGPT Plus for Employees, Some Thoughts on AI
Zooming Out and Acknowledging Progress

Agency Journey Episode 30 (Y16M9), February 2023

The Tension Between Gratitude and Growth
Some New Business Wins But Behind Pace
Continuing to Strengthen Partnerships
DTC Patterns Podcast
Taking Off the Blinders Necessitates Bold Moves

Agency Journey Episode 29 (Y16M8), January 2023

Confidence in Our Systems and Structures
Navigating Setbacks to Start the Year
Doing New and Different Things to Generate Business Momentum
Taking an Inner Stance of Fearlessness

Agency Journey Episode 28 (Y16M7), December 2022

Trouble “Turning Off” During the Holidays
Mixed Results in Finishing the Year
Wrapping Up Strong First Full Year for Both Vaulted Oak and BX Studio
Reflecting on a Negative Glassdoor Review
Lessons to Take into 2023

Agency Journey Episode 27 (Y16M6), November 2022

Black+Decker Website Launch
Delays on the New Business Front & Learning From Lost Deals
New Barrel Holdings Website
Takeaways from Breaking Down Our Finances
Leveling Up Performance & Making Fearless Decisions

Agency Journey Episode 26 (Y16M5), October 2022

Q4 Barrel Partners All-Day and Barrel Holdings Meeting + Dinner
Barrel Retreat in NYC is a Success
Shopify Unite and SoDA GMM
New Business Wins and a Critical Launch
Tightening the Screws on Our Processes

Agency Journey Episode 25 (Y16M4), September 2022

Getting into Rhythm as an Agency
DTC Patterns, 1 Year Later
Progress in Marketing the Agency
Analyzing New Business Wins
Finishing the Year Strong

Agency Journey Episode 24 (Y16M3), August 2022

Gearing Up for Team-wide Retreat in October
Vaulted Oak Celebrates 1 Year of Being in Business
Continued Momentum with New Client Wins & Sales Efficiency
New Client Website Launches
Going on the Offensive with Talent
Focusing on the Basics: Revisiting and Reframing Our 2022 Theme

Agency Journey Episode 23 (Y16M2), July 2022

A Key Structural Change That’s Had Big Impact
Launching Projects & Winning New Work Boosts Morale
Quarterly Meetings with Team Leads, Partners, and Barrel Holdings Portfolio Companies
Responding to a Client Project Crisis and Doing Some Hands-on Work

Agency Journey Episode 22 (Y16M1), June 2022

Leveraging Audits as a New Business Tool
Testing Out Discipline Team Retreats
The System of Accountability
Twelve Months from Now

Agency Journey Episode 21 (Y15M12), May 2022

Re-onboarding 1-on-1s with the Team
Town Hall and a Tough Question About Layoffs
Patience and Enabling Execution

Agency Journey Episode 20 (Y15M11), April 2022

A Professional Liability Case
Our First Ever Barrel Holdings Quarterly Review Meeting
A Longtime Client Gives Notice
Shifting C-Suite Responsibilities
Performance and Standards in Managing Employees

Agency Journey Episode 19 (Y15M10), March 2022

A Couple of Launches
Boomerang Hire, Our New Director of Software Engineering
Staying Tight on Costs

Agency Journey Episode 18 (Y15M9), February 2022

Hard Realities and Tough Decisions
Heads Down Execution

Agency Journey Episode 17 (Y15M8), January 2022

New Business Wins & Outbound Action
Team Attrition Setbacks & Q12 Worries
Annual Planning Meetings
Simplifying the Business with Key Metrics
We Launched a New Portfolio Company

Agency Journey Episode 16 (Y15M7), December 2021

Working in New Team Members
New Launches & New Wins
Keeping It Simple in 2022

Agency Journey Episode 15 (Y15M6), November 2021

Containing and Putting Out Fires
New Launches & New Wins
Achieving Hiring Goals
Sharpening My Focus in Key Areas

Agency Journey Episode 14 (Y15M5), October 2021

Missing the office vibe
Quarterly Partner Meeting in person
Choppy Waters: Business Struggles & Team Turnover
Sports Analogy: Taking Our Eyes Off the Games

Agency Journey Episode 13 (Y15M4), September 2021

The unstoppable force of human adaptation
DTC Patterns
Barrel Manager Growth Framework
The need to refocus on client outcomes

Agency Journey Episode 12 (Y15M3), August 2021

Building a Talent Acquisition Discipline
Modernizing Our Financial Systems
Launching Vaulted Oak, a New Agency Business
Staying Disciplined on the New Business Front

Agency Journey Episode 11 (Y15M2), July 2021

In-Person Partner Planning Meeting
Mid-Year Reflections
Barrel Maxims
All Feedback is Information (How we responded to negative Glassdoor review)

Agency Journey Episode 10 (Y15M1), June 2021

Celebrating 15 Years
New Talent Acquisition Manager
No More Fighting Fires
Agency Business Model

Agency Journey Episode 9 (Y14M12), May 2021

Launches & New Business Wins
Immunity to Change Map
New Org Structure
Prioritizing Talent Acquisition

Agency Journey Episode 8 (Y14M11), April 2021

Wes Celebrates 10 Years at Barrel
Quarterly Town Hall
Initiatives Across the Board (Impact of coaching)
Leadership (Making hard decisions)
The Downstream Impact of Business Development

Agency Journey Episode 7 (Y14M10), March 2021

Leveling Up on HubSpot
Agency One-Pager
Novus Global Training
Busting Through the Intuitive Fence
Systematizing Lead Generation

Agency Journey Episode 6 (Y14M9), February 2021

Making Meetings Effective
Sei-Wook Becomes a Dad
Tightening Up Our Services Offering
Reimagining the Way We Work (Moving to Asana)

Agency Journey Episode 5 (Y14M8), January 2021

A Week of Looking Ahead (Annual planning meetings recap)
Our Director of Client Services Starts
Profit Share Goes Out
A Few of Sizable Investments (Professional services membership org and coaching)
Project Delays and Their Impact
Team Structure, Utilization, and Leverage