One of the hardest calls for an agency leader comes when the business grows and hits a true inflection point. Client expectations rise, operations get more complex, and the team needs stronger, more adaptive leadership. Despite coaching, consultants, and other support, a long-tenured team lead may simply stop growing. They reach a ceiling or show little interest in evolving with the agency’s new demands.

This creates a real dilemma: balancing loyalty to the past with responsibility for the future.

Loyalty offers comfort. It signals that the agency takes care of its people, values continuity, and honors institutional knowledge. I’ve chosen loyalty many times, keeping people in key roles even when I knew they had stalled or were holding us back in certain areas. It felt safe, familiar, and fair.

But the agency leader’s obligation is to the future. And that often means making the difficult personnel decisions. Choosing responsibility does not require being cutthroat. You can transition someone out with respect, gratitude, and care. But you still owe your team and your clients a leadership bench capable of meeting the next level of complexity.

The irony is that delaying the hard call usually makes the eventual decision far worse. When a team lead plateaus and continues to underperform, the business suffers, your frustration grows, and a painful firing becomes inevitable. Had you acted earlier, with intention and respect, you would have spared both the agency and the individual from a harsher outcome.

The lesson is simple but difficult to practice: leaders must confront these dilemmas early, not after the damage has been done.

About Agency Journey: This is a monthly series detailing the happenings at Barrel Holdings, a portfolio of agency businesses. You can find previous episodes here.

Highlights

Looking into Raising for a Deal

We signed an LOI in November that is very promising. We’re in due diligence and also lining up financing. We’re also exploring a potential fundraise to bring some investors on board. While we can fully fund this deal on our own, we think it’s a good opportunity to start building a track record of taking on investment and posting results.

I’ve been looking into what’s involved for a fundraise. We have a deck that’s in the works. We’ve also been talking about whether or not this will be done as a Reg D 506(b) or 506(c) fundraise.

506(b) forbids us from publicly marketing the fundraise, so that means we can’t post about it on social media or any newsletters. It must be 1-to-1 with people we know. It does allow for up to 35 non-accredited investors. This is the common approach taken by many raising family and friends rounds. So no public solicitation with this path.

506(c) allows for public marketing but the SEC requires verification that the investors are accredited (income greater than $200k or net worth great than $1 million, not counting primary residence). This must be done with real documentation or with a 3rd party service. With 506(c), we can more freely discuss the deal terms and that we’re taking investment. It requires more overhead and also rules out any non-accredited investors.

We’re leaning towards the latter especially as we build a network of people who want to follow along our journey and participate in opportunities we bring to the table. If we can post strong results with this first deal, we believe it may allow us to raise larger amounts for future deals and even cultivate an engaged pool of repeat investors who come along with us on multiple deals.

I’m sure there are plenty of headaches and learnings in store for us, but it’s one that we believe is worth exploring to unlock new approaches to funding our deals.

Note: This section is for educational purposes only and is not an offer to sell or solicit investment.

AgencyHabits Knowledge Share Session

We held our first ever “Knowledge Share” session for AgencyHabits. Ivona organized a virtual meetup through our newsletter.

Screenshot of some of the attendees at our AgencyHabits Knowledge Share meetup.

Because of the way we set it up, we actually had no idea who would be attending (something we’ll fix for next time), so I had no idea whether it would be a couple of people or more.

To our surprise, 27 agency leaders joined the call from all over the world.

I presented on “how founders should think about time” to kick off the knowledge share session.

I presented on a topic, “How Founders Should Think About Time” and we then had a roundtable discussion around prioritizing and bottlenecks in running the business (check out the presentation here).

We were encouraged by the initial turnout and have been brainstorming ways to provide more such experiences in 2026.

I still remember having our one and only AgencyDocs sponsored meetup at a brewery in Gowanus, Brooklyn some years ago. I do think a combination of in-person and virtual events for our growing community is something that could be valuable to offer along with our podcast and written content.

Getting Some Ops Help for Sei-Wook

My co-founder Sei-Wook is a high capacity individual who gets a lot done and complains very little. However, I could tell that in recent months, he’d been feeling the strain. Between shutting down an agency, exiting three agency entities, finalizing taxes, closing the books, being pinged on form various legal and HR matters across the portfolio, and also doing M&A, the list of to do’s have been never ending for him.

While I’ve been able to make do without Sei-Wook on the deal sourcing and qualification front, leaning more on our friend Brandon Pae who has stepped in to support many of our M&A activities, he’s absolutely necessary for due diligence and financing. So Sei-Wook and I talked at length about getting him some help across our portfolio operations, especially the day-to-day admin-related asks that’s bogged him down.

Luckily for us, a friend from my high school years, Annabel, was available and had relevant experience. She’s had been a controller for a restaurant group and was also a do-it-all generalist operations leader with experience in HR and compliance matters. While it’ll take a few weeks to fully ramp her up, we’re hoping she provides much relief to Sei-Wook so he can spend more of his time on the M&A side.

We don’t want a bloated support service structure at the holdco level in the long run, but I think we’re at a scale where having a helping hand on the ops side is warranted. Having consistent solutions for finance reporting, robust employee handbooks, thorough MSAs, up-to-date insurance, prompt responses to client and government compliance requests, and any other ops details can take a load off of our already busy agency leaders.

Top of Mind

The Barrel Holdings Story Beyond the Strategy

For much of the past year, Sei-Wook and I have spent time defining and refining our strategy for Barrel Holdings: setting 1, 3, and 10 year goals, how we plan to grow, and the set of activities we’re focusing on. On this front, I think we’re in a good spot, we just need to execute (see last month’s “Top of Mind” for more on this).

However, one thing we found lacking was the overarching narrative. Why were we doing this? What was the point? Did we have a point of view on the future of our industry/category and the role we want Barrel Holdings to play in it?

I’ve been crafting up some decks to help me figure this out and getting feedback from Sei-Wook. It’s a work in progress, but it’s been a helpful exercise.

A few slides from a deck I’ve been working on to develop the Barrel Holdings narrative on why we exist and our “operating ecosystem” model.

Where we’ve landed as of now is somewhere along these lines:

• There’s ever-increasing amounts of complexity and fragmentation happening across the marketing, commerce, and digital services landscape. It’s not an easy world for companies to navigate.
• These companies need expert firms more than ever, especially those that specialize in deep and specific ways. We believe that the next decade belongs to boutique specialized agencies with depth, focus, and speed.
• But boutique specialized agencies have a challenge. They’re often weighed down by aspects of the agency business that don’t necessarily have to do with their expertise: finance ops, hiring, sales and marketing, etc. These often suck up a lot of time, especially for the agency founder, and make it hard for the agency to invest in innovation and growth.
• This is where the Barrel Holdings model provides a solution. We become a partner that provides an “operating ecosystem” that helps lessen these burdens on specialized agencies while helping them preserve their identity and autonomy.
• This is why we’re deliberate about the agencies we acquire (specialized, small, with strong growth potential) – we see tremendous opportunity for these agencies to flourish within our ecosystem.

There are aspects of this narrative I still need to finesse and make more cohesive, but it’s a start. It’s resonated with us because we really do believe in it. The agencies in our portfolio today do enjoy support and certain advantages that the ecosystem provides, and it’s only getting more robust.

Shared Quotes

“The people with the best self-control are typically the ones who need to use it the least. It’s easier to practice self-restraint when you don’t have to use it very often. So, yes, perseverance, grit, and willpower are essential to success, but the way to improve these qualities is not by wishing you were a more disciplined person, but by creating a more disciplined environment.” (James Clear, Atomic Habits)

The lessons from this book never get old. This particular one about creating a more disciplined environment still resonates 10 years after I first read it. For me personally, I can still be much better about cleaning up my content consumption habits (limit access to X and LinkedIn) while also making it more appealing to sit down and read more books.

“People on the success curve live a life of responsibility. They take full responsibility for who they are, where they are, and everything that happens to them. Taking responsibility liberates you; in fact, it is perhaps the single most liberating thing there is. Even when it hurts, even when it doesn’t seem fair. When you don’t take responsibility, when you blame others, circumstances, fate, or chance, you give away your power. When you take and retain full responsibility even when others are wrong or the situation is genuinely unfair you keep your life’s reins in your own hands.” (Jeff Olson, The Slight Edge)

This is essentially about living a high agency life. Instead of lamenting external factors like the economy, clients, AI, etc. or blaming the shortcomings of employees and partners, it’s a more empowering stance to focus on what you can do and really own it. Sometimes that means taking responsibility for things that weren’t your direct mistakes, but good leaders aren’t afraid to accept that the buck stops with them.

One more disclaimer: This is not an offer to sell or solicit an offer to buy securities. Any investment opportunity discussed would be offered only under SEC Rule 506(c) to verified accredited investors through formal offering documents.