Every company hits a moment where the thing that worked at ten customers breaks at a hundred. What Breaks First sits down with founders, operators, and industry voices who have lived through that fracture: the hire that came a year too late, the process nobody thought to build until it was too late not to, the handoff from founder instinct to operator discipline. Hosted by Ian, joined by Matt & Ben, each episode trades the highlight reel for the honest account. No case study gloss. Just what actually broke, what it cost, and what replaced it. For founders, operators, and anyone building past the point where duct tape stops working.
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Andrew Graff has run Allen & Gerritsen, an independent creative, media & PR agency in Boston and Philadelphia, with over 100 people, for 31 of its 41 years.
After his trusted and beloved EA left for another career path, he went through half a dozen in-house Senior EAs that couldn’t keep up. When he was on the brink of giving up, he was introduced to an unconventional solution from a country he had never heard of before.
"I was skeptical. I'll be candid: could this work? But I was frustrated enough to be open-minded enough to say I could do it a different way."
So he treated it as a three-month experiment. Low risk, in his words, and buying himself time, because it was clear he couldn't keep doing it himself.
Then he met Dulara.
"Honestly, meet Dulara, I was like, within three hours, all right, this is life-changing."
His own onboarding team told him she was the quickest person ever to onboard into the company.
What it looks like now: a half-hour call every morning, then an end-of-day summary of what she closed, what's still open, and what he owes people.
"We look like the most responsive team ever, because within an hour or so she's like, here's his availability, pick a time, I'll send an invite."
And the line that best illustrates what it’s like to have a great EA:
"For somebody who's never been to New York, she can navigate me in meetings in New York better than anybody before."
Introducing episode one of What Breaks First, hosted by Ian Myers, Founder & CEO of Oceans Talent.
Andrew Graff
Meet Dulara. I was like, within three hours, I was like, all right, this is life-changing.
Andrew Graff
Hi, I'm Andrew Graff. I'm the CEO of Allen and Garrettson in Boston and Philadelphia. We're an independent creative media design and public relations agency with over a hundred employees, a combination of full-time, fractional, and Oceans Divers.
Ian Myers
So, Andrew, you have run an independent agency for decades. What broke first? What are the things that started to go wrong? What was challenging operationally? And then also from like a revenue business standpoint.
Andrew Graff
We ran into a speed bump. It's every agency's worst nightmare. One of our largest clients filed for bankruptcy on us.
Ian Myers
So things are going well. Presumably the business is growing beyond the startup phase. You've been around for almost 20 years. How many people?
Andrew Graff
Probably 160, 170.
Ian Myers
That's a big, that's a big business.
Andrew Graff
Yeah. And then we get that phone call that everybody dreads. Not that a client is letting us go, but a client was filing for bankruptcy. And it was a very big national brand.
Ian Myers
Just to give people perspective on the scale of what we're talking about here, what percentage of revenue?
Andrew Graff
Uh at the time it was probably about 30% of our revenue.
Ian Myers
That is wild.
Andrew Graff
Yeah. I had some like warning signs because like they were all of a sudden like really slow to pay, and I they still owed us quite a bit of fees, but it was dollars we owed to the media and to the production.
Ian Myers
Right, of course. Yeah. How long did you feel sorry for yourself? And then how long did it take you to just kind of kick into action?
Andrew Graff
Yeah. You can feel sorry for yourself for about a day, and then you have to spring into action. And you just you have to pivot. What you learn really quickly in those moments, you definitely have to do the hard things. You can't let it impact all your other clients. You absolutely have to keep everybody motivated because now they're sheer panic for their job. Right. And you know, we had to make cuts and make adjustments and all of that. But it was good, like it was a terrible lesson, but a great lesson to learn. We defied odds and then just got back on track within a year, which is nuts.
Ian Myers
That's wild. So you're running one of the largest independent agencies in the country. It's been 30 years. What are the challenges that you experience? What are the things you focus on? And what is how does it all come together in terms of your responsibilities?
Andrew Graff
You know, if you you think about the COVID time period, and keeping in mind that our biggest investment or our biggest expense is around talent. Our next part of our chapter is around a progressive workforce model. And when you think about that, it's small things like meeting invites, you know, and keeping track of like, all right, well, this person doesn't work on this day, this person has a different time zone, like all that. It creates a lot of chaos in how you get work done. I had the same executive assistant for a long time. She wanted an opportunity where she could be in person with other people, so she left. And then I went through the series of like various executive assistants to the point where I was like, I might as well just do this myself at this point.
Ian Myers
What could possibly cause someone like you to get to the point where they're saying, I could do this myself, I can't find the right person to do this for me. What were some of the things that were happening? I mean, was it your calendar? Was it your emails? Was it your coordination? What were the things that were slipping through the cracks?
Andrew Graff
You know, you you sort of ask the this question about like what does my day look like? And my day is like always jams, and I have to switch from topic to topic really quickly. You know, I I'll look at my my calendar, and calendar is a big part of it. It changes constantly during the day. You know, somebody needs to see me, somebody's not ready to see me, a client thing pops up, a new business opportunity pops up, and it's this constant, constant changing. And I, you know, I need somebody to keep up with me.
Ian Myers
You were struggling to get there because you were struggling with finding the right people.
Andrew Graff
The right people who can like this same old way as I'm blowing through like people who just can't keep up with me, frankly. And and then the output would be wrong. And I'd like to have to redo it. And I was like, all right, like we gotta do something different, and I am willing to do it. And somebody had introduced us, said, I've been working with uh an executive assistant for over a year in Sri Lanka. Oh no, what they said is a virtual assistant, and I'm like, okay, what's that? Um I don't need a chat bot, I need like a human. So I was skeptical. I'll be candid, like, could this work? But I was frustrated enough to be open-minded enough to say I could do it a different way. I was sort of like, all right, it's worth an experiment for three months. No question about it.
Ian Myers
Obviously, the cost factor, the three months is equivalent to one month or whatever of a of an in-person American yeah that wasn't working out for you.
Andrew Graff
So I imagine it was like a low risk because it was clear I couldn't do it myself, and be like true to who I am, which is responsive. And I was like missing meetings because I forgot to put it on my calendar. I mean, I'm not good at it. I will be really clear, honestly. Meet Dulara. within three hours, I was like, all right, this is life-changing. For somebody who's actually never been to New York, she can navigate me uh in meetings in New York uh better than anybody before. Like, it is like I it just she's like, all right, this is where you need to stay, this is where you need to be, this is how you're gonna get from point A to point B. Here's enough time to get there. She makes it seamless. It is crazy. So as a result, I've given her more and more to do. So she owns our internal company newsletter, our external newsletter.
Ian Myers
Sounds like a lot for an EA to be doing.
Andrew Graff
Yeah, she's like the publisher, she gets she gets all the content from various people, she orchestrates it. We have a once-a-month company meeting that's all in slides. She makes sure everybody's doing what they they need to do. She orchestrates it all, she keeps everybody accountable. I would never know she wasn't sitting next in the same room with me all the time.
Ian Myers
It's wild given that she is a 26-hour plane ride away. Uh, I think a lot of people, when they're making decisions about who to hire and whether to work with folks who are offshore, are really looking at what's the cost to value? What has your perception been of kind of the cost to value ratio and working with folks offshore?
Andrew Graff
Lower cost maximum output. Way more output than I was used to. There are some days, honestly, where I'm the one who's falling behind, not her. And now I feel accountable to make sure that by the time she asks me again that it was done, you know.
Ian Myers
It is interesting that a lot of uh folks have described to me the reason that they really enjoy working with an EA is the same reason they hire a personal trainer, which is they can go to the gym by themselves every day, but they don't get the results without someone being there to help them stay accountable and know what they should be doing. The accountability buddy is an undervalued part of the EA experience. Can I switch gears a little bit because we're talking about predictive, we're talking about support, and I'm just starting to think about uh you mentioned earlier AI, which is kind of the elephant in the room for a lot of any kind of service business. In this specific instance, I'm wondering why do you still need an EA? Why does your company still need operators in our current age of AI?
Andrew Graff
I mean, it's very simple. We're in the business of creativity and originality and craft. Marketing is about relationships, there's nothing artificial about it. And so our point of view on this whole thing is very much this notion of it's not an either or, it's a together. We will always be human intelligence, creatively led, but AI supported. It's an accelerant, and humans in our business remain the engine.
Ian Myers
To close it out, what would you tell an executive, a leader, a CEO who feels like they're drowning, who feels like the difficulty of scaling is taking its toll emotionally, physically, mentally. What would be your advice to them?
Andrew Graff
I'm gonna actually share the advice you guys gave me. Open up your mind. Give her the things like you just wish you could pass on to somebody else that you don't want to do. She's quick, she's good, like she's faster than me. And some of those faster than me are things that like I would put off doing. Yeah. And she does she just takes care of it, like in the overnight. Uh way better than I ever imagined I would do.
Ian Myers
Yeah.
Andrew Graff
Active listener, proactive thinker, anticipating. It's what anybody would want in any employee.
Ian Myers
Thank you, Andrew. This has been really eye opening. I cannot believe that you are in such a state of calm all the time about all the things that are going on. I've I don't think I've ever met an agency owner as optimistic and as chill as you.
