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E13: Jason Hennessey

Scaling Smart: The Journey from Freelance SEO to International Agency

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Podcast Overview

You start as a freelancer. Just you, a laptop, and a search ranking obsession. Fast-forward a few years: your agency is pulling in $10 million a year. Offices in LA, Vegas, the Philippines. A 100-person global team.

Sounds like a dream, right?

Jason Hennessey

Jason shares his incredible journey from early freelance SEO gigs to building Hennessey Digital, a powerhouse agency serving major U.S. law firms and generating millions in revenue.

In this episode of eCom@One with Richard Hill, Richard interviews Jason Hennessey—entrepreneur, SEO strategist, author, and speaker. They dive into how Jason scaled his business organically, starting with a Craigslist ad and eventually building a distributed team across continents.

He breaks down how to hire for creative freedom, why personal branding can open doors faster than cold emails, and how SEO is really just a form of storytelling—done with strategy.

Jason also opens up about burnout, starting over, and the mindset shifts that took him from six figures to eight. Whether you’re an agency owner, SEO nerd, or just love a good business build-up story—this one’s for you.

The episode is packed with smart, honest insights on growth, team-building, niching down, and trusting the long game.

Topics Covered

Topics Covered: 

00:00 Scaling Agencies: Insights from Jason Hennessey

03:29 Leading Law SEO Agency Insights

08:30 Scaling Business by Hiring Experts

12:22 Documenting Time and Task Management

15:04 Hiring and Business Culture Insight

17:05 “Building a Team-First Culture”

19:59 Hackathon Innovation: HD Translate

25:24 Adapting SEO with AI Innovation

26:32 “Personal Branding for Agency Success”

29:45 “Book as Unique Selling Point”

33:01 Navigating Burnout and Business Challenges

36:29 Balancing Work and Personal Life

39:43 Email Management and Availability

43:07 “My Grandfather, My Greatest Mentor”

46:26 “Balancing Growth and Risk”

Richard Hill [00:00:08]:
Welcome to episode 13 of Agency Intensive. I'm Richard Hill, your host and in this episode I sit down with Jason Hennessey. Now, Jason, I've seen Speak many times. He's an entrepreneur, author, speaker, and founder of Hennessy Digital, a leading SEO agency specializing in legal marketing. Very specialist in. In this conversation we dig into how Jason scaled his agency from freelance beginnings to a global team of over 130 without losing sight of culture, vision or performance. We also touch on his best selling book, how he uses vivid vision to lead and how Jason structures his time to focus on impact. If you're thinking about how to grow your agency, lead with intention and build a truly scalable operation, this one is packed with absolute insights.

Richard Hill [00:00:49]:
So if you can just do me one favor, hit the subscribe or follow button wherever you are listening to this show and you'll never miss another episode again. What a treat. Thanks very much. Let's get into it. Hi Jason, how you doing?

Jason Hennessey [00:01:05]:
Very well, Richard. Thanks for having me on your podcast here. I appreciate it.

Richard Hill [00:01:10]:
No problem at all. Thanks. Thanks for coming on the show. But I think before we get into the nitty gritty of running a very successful agency, I think it'd be great to introduce yourself and tell our listeners how you got into the world of running an agency.

Jason Hennessey [00:01:23]:
Yeah, so my journey began in 2001. So 24ish, maybe years ago, maybe 25 close on. And so I that's my how I entered the world of SEO. I was a small business owner that needed SEO help. So I taught myself how to do it. That journey, just kind of doing it on my own, you know, lasted a couple years. And in 2008, fast forward about seven years, I was giving a presentation at a conference. It was a lawyer marketing conference.

Jason Hennessey [00:02:03]:
I was talking about, you know, some of the results I was getting in the world of like e commerce and other affiliate marketing type stuff. And so that was kind of the genesis of what started an agency. A bunch of the lawyers said, hey, this is really awesome. Have you ever considered, you know, doing this for other people? And so I'm like, not really, but give me a business card. And so I ended up leaving that one presentation with about seven business cards and maybe like 30 grand per month in reoccurring revenue just from one 45 minute presentation. So that's how it all began. I guess that was a pretty good day then.

Richard Hill [00:02:40]:
So you went to do a presentation about SEO as a whole with no sort of preconceptions of sort of selling anything. People like what People like what you had to say and then business cards followed up, got a client or two and started off with a 30k a month revenue stream. So that wasn't a bad day, was it?

Jason Hennessey [00:02:59]:
I mean, yeah, it really wasn't. I mean, considering, you know, like, you know, when you talk to a lot of agency owners like, you know, it's very hard to kind of get your first couple clients like that. And I kind of accidentally stumbled into it and I guess it was just based on how transparent I was in this presentation. I feel the more that you educate and the less that you sell.

Richard [00:03:20]:
Right.

Jason Hennessey [00:03:20]:
You know, that's like one of the secrets of building an agency is, is give it all, you know, give it all away. You know, I think that's a, I.

Richard Hill [00:03:29]:
Think that's a great way to sort of run your agency. I think a lot, obviously a lot of agency owners are quite careful what they share. But I've seen you speak as, as I said before we hit record, I've seen you speak at a couple of big events, you know, probably a thousand people at Chiang Mai SEO, 900 people. And sharing how you'd built your agency, but obviously on the, on the flip side, sharing to lawyers and people within the law industry, you know how to do SEO. And fast forward, what, 17, 18, 19. 17, 18 years years later. Yeah, you're now very much, I think cemented yourself as, you know, one of, if not the top law SEO firms in the world.

Jason Hennessey [00:04:06]:
Yeah, yeah, no, it's, it's definitely been a, a journey for sure. You know, building it off of like one really good and making that pace cutty case study world class and then kind of growing it into the next case study, the next client and the next client. And then, you know, we make a lot of mistakes over the years, right. But we learn from the mistakes, build a world class team. And you know, now the clients that hire us today, right. Don't have to pay for the same mistakes that we made 10 years ago. You know.

Richard Hill [00:04:40]:
So let's go back a couple of things there. Obviously the niche, you know, for lawyers building team, we'll definitely get into that. But, but let's stick with the niche for a minute. So obviously right at the beginning you were giving a presentation to lawyers, obviously got X amount of clients. So you know, great, great starting point. But then, you know, I know you've created, you know, you do a lot of talks, you, you've even created a book, you know, law SEO. But how would you say, how pivotal has it been to have that special Specialization with law. And what would you say to other agencies that are sort of maybe trying to do a bit too much rather than.

Richard Hill [00:05:15]:
Or focus on too many industries rather than focus on one.

Jason Hennessey [00:05:19]:
Yeah, so I, I'd like to say that that was a strategy from the beginning. It really wasn't. You know, I accidentally kind of stumbled into that, that niche and then there was just so much opportunity in that niche that I just kind of continued to, you know, double down and double down and then just kind of market just in that vertical. You know, I think, you know, it makes a lot of sense when you start to niche down.

Richard [00:05:47]:
Right.

Jason Hennessey [00:05:47]:
Like, I don't think my agency would be where we are today if we didn't niche down just because it's very hard, you know, to kind of, you know, scale an agency to begin with. But when you're trying to scale an agency where your core competencies are spread, you know, you're doing E commerce and next thing you know, you're working with a plumber. Now you're working with a doctor. And it's like, yeah, you know, the beauty is that because we only work in one niche vertical. Like, we already have a proven model that works, right. And it's just a matter of like replicating that model, right? It's like building a McDonald's, right?

Richard [00:06:26]:
It's a.

Jason Hennessey [00:06:27]:
You know, we know that this is the way that we make a hamburger. We put two pickles on it, a little squirt of ketchup, you close the bun, right? And it's just like, boom. And so whenever we get a new client, it's like we can replicate it, right? It's like, it's like you own a McDonald's, but now somebody walks in and they want like something that's.

Richard Hill [00:06:44]:
They want a pizza. Yeah, we don't have a pizza oven.

Jason Hennessey [00:06:48]:
How do we make a pizza? All right, we can hire somebody, make a pizza, but you kind of get the point, you know?

Richard Hill [00:06:52]:
Yeah, yeah, yeah, no, I get it, I get it. So obviously started in, in law by chance more than anything, but really doubled down, doubled down, doubled down and really focused on that and obviously made a name for yourself in that area. But I would say obviously quite a, quite a wealthy industry, you know, quite a tough industry in terms of ranking, competitive. So nice, nice fee structures in that industry, which, which I would imagine is obviously, obviously key and helps you to then invest that money in, in growth operations people. So I think, you know, my notes say you're at about 130 people now. Would that be about right? Yeah, that's.

Jason Hennessey [00:07:28]:
That's about accurate. Yeah. You know, between 130, maybe 140, I'd say. Yeah.

Richard Hill [00:07:33]:
So in the space of about six minutes, we've gone from setting up, doing a presentation to 130 staff. But I think, obviously, as I'm sure we all know, it probably wasn't always a sort of a straight line up, you know, maybe. Maybe through some of the unexpected challenges that you've had across, you know, the. The years, throughout the years and what. What you've done to sort of tackle those.

Jason Hennessey [00:07:55]:
Yeah. So I think. I think the first three, maybe three and a half years, you know, the agency was like most agency owners. It was really a lifestyle business, you know, where, you know, I was trading, you know, hours for dollars. You know, I was going on vacations and being pulled from, you know, the beach up to. To my hotel room to take a sales call.

Richard [00:08:19]:
Right.

Jason Hennessey [00:08:19]:
You know, and so, like, I was kind of the constraint within the business.

Richard [00:08:24]:
Right.

Jason Hennessey [00:08:25]:
At the same time, I was making a lot of money.

Richard [00:08:27]:
Right.

Jason Hennessey [00:08:27]:
Because your margins are high when you don't have that many people.

Richard Hill [00:08:30]:
Yeah.

Jason Hennessey [00:08:30]:
And so, you know, I. At the end of that year, I had to, you know, write a large check to the government, you know, for taxes. And I'm like, why did I waste so much of my time kind of doing this when I just have to give over a lot of my profit to the government anyway? And so I'm like, you know what? I'm just gonna like, really kind of start to scale this. I'm gonna go hire people way smarter than me, and I'm just gonna kind of grow it, and I'm gonna try to replace everything that I do with people that are more competent than I am at it, so that it frees up my time to kind of focus on my zone of genius, whatever that is. And so I hired a. A good coo, who then helped me to recruit a cfo, who helped me to recruit a cto. And then, you know, next thing you know, we started doing, you know, to. To lay your, you know, layered management underneath them.

Jason Hennessey [00:09:21]:
And so that year, you know, shortly after, we kind of like doubled in revenue.

Richard [00:09:26]:
Right.

Jason Hennessey [00:09:26]:
I think we went from like 4 million in top line to like 8 million.

Richard [00:09:30]:
Right.

Jason Hennessey [00:09:30]:
So, like, it was a lot of, like, big investments, and I was taking a lot less money because I was reinvesting it into people.

Richard [00:09:37]:
Right.

Jason Hennessey [00:09:37]:
And so it was all by design. But the beauty is I was basically freeing up my time to do things like writing books and doing podcast and.

Richard [00:09:48]:
Right.

Jason Hennessey [00:09:48]:
You know, and Speaking on stage. And. And so now that I had free time to kind of do that, that really helped to accelerate the marketing and building the personal brand.

Richard Hill [00:09:58]:
Yeah.

Jason Hennessey [00:09:58]:
And now I had all of the team behind me to actually execute and help to actually scale it. And so it quickly went from a lifestyle business to more of like an enterprise agency, you know, and so I like that.

Richard Hill [00:10:12]:
So that you. So. So you're spending a lot of your time now or since then, speaking podcasts, creating content, writing, you know, and obviously filling the funnel, building the. Building the pipeline with. With those activities. But some of those first key hires I'm thinking of, there's maybe people listening now that are, you know, 2 or 3 million US or 3 or 4 GBP GBP. And they're at that stage where they're trying to hire these bigger hires, you know, these. These heads, these CEOs.

Richard Hill [00:10:45]:
What advice would you give to the people that are sort of looking for these bigger hires? Yeah.

Jason Hennessey [00:10:50]:
So it doesn't always have to be. You don't have, like, if you're only at 2 million, you know, I mean, you don't have to go look for a COO per se, you know, because with those titles, you know, there's also, you know, cost that's associated with that. So you might not be at the level that you need a C, O, O.

Richard [00:11:07]:
Right.

Jason Hennessey [00:11:07]:
Or you need a CFO yet, you know, but at least start with getting, you know, somebody that might be like a. An operations manager or somebody to kind of help whatever it is that you're not good at.

Richard [00:11:21]:
Right.

Jason Hennessey [00:11:21]:
If you're better at sales and you're not really good at operations, which is basically kind of like me. Yeah. You know, I'm going to go try to find somebody and put the best person in place that I could afford to. To take over the operations so that I could focus more on the sales side, if that's kind of what my strength is.

Richard [00:11:39]:
Right.

Jason Hennessey [00:11:39]:
Or if you're better at operations.

Richard [00:11:41]:
Right.

Jason Hennessey [00:11:41]:
Maybe you slide into that role and you hire somebody to kind of help take over sales.

Richard [00:11:45]:
Right.

Jason Hennessey [00:11:45]:
So. But just know your. Your own personal limitations.

Richard [00:11:51]:
Right.

Jason Hennessey [00:11:51]:
And figure out, like, where's the best use of your time and. And then just go try to hire the best available resource that you can afford, you know?

Richard Hill [00:12:00]:
Yeah, I think that's the thing. I think a lot of agency owners are usually pretty good at selling, but the agency is reliant on them to sell. And then the challenge comes where the delivery is. Either there's challenges or it's just pushing and creating. So Much work for the owner. It becomes very, very challenging to have a, have a lifestyle outside. Outside of the agency.

Richard [00:12:20]:
Yeah.

Jason Hennessey [00:12:21]:
Correct. Yeah.

Richard Hill [00:12:22]:
I think in one of the presentations I saw you do maybe 18 months ago, I think you talked about sort of documenting what you're doing and what you're spending your time on. And I know this is more from a personal. I'm quite interested myself. So obviously we talked about the bigger hires, but then where. I think a lot of agencies we speak to are still doing a lot of their own sort of diary management, podcast management. And I know when we liaise with your office, we liaise with your, I believe, executive assistant.

Richard [00:12:49]:
Yes.

Richard Hill [00:12:51]:
How important has that been to you? To sort of be able to spend your time on bigger tasks, tasks that you should be focused. Focusing on Getting his. Getting an executive assistant.

Jason Hennessey [00:13:01]:
Yeah, that, that was, that was very key. And it was something that I wasn't even aware of that I needed an executive assistant. It took me going out and getting an executive coach to tell me that. He's, you know, he's like, hey, by the way, do you have an executive assistant? And I'm like, no. And he goes, well, guess what? You are the executive assistant.

Richard Hill [00:13:22]:
Yeah.

Jason Hennessey [00:13:23]:
You know, and it was, it was so true. And so he told me to do an exercise, which I'll share, you know, now that I think could be very valuable to anybody listening. You know, what he told me was, is to, you know, document, you know, my time over a three week period.

Richard [00:13:41]:
Right.

Jason Hennessey [00:13:41]:
Write down every little thing that I do from checking email to doing payroll to managing somebody.

Richard [00:13:49]:
Right.

Jason Hennessey [00:13:49]:
You know, every little thing. Writing a book, you know, writing a chapter in my book.

Richard [00:13:53]:
Right.

Jason Hennessey [00:13:53]:
And, and so kind of just go through and document your whole time. And then from there you're going to basically put four columns on a spreadsheet and the columns are going to be, are you incompetent? So that would be I, Are you competent? C. Right. Is this, Are you excellent at something? So that would be E. And then you would be unique.

Richard [00:14:13]:
Right.

Jason Hennessey [00:14:14]:
And so checking email, I'm competent, right. You know, doing payroll, I'm incompetent. That's not really much, right. Being on a sales call, maybe I'm excellent at that. Right. And writing a chapter of my book, that's very unique to me.

Richard [00:14:29]:
Right.

Jason Hennessey [00:14:30]:
That's something that only I could do. And then from there then he said, then just start marking hourly rates. Like, what would you pay somebody to do these tasks?

Richard [00:14:39]:
Right.

Jason Hennessey [00:14:40]:
So checking email, Maybe you pay $20 an hour to do that. Maybe you pay you get the point. And so if you kind of go through this exercise, you'll quickly realize that you're probably spending a lot of your time doing $20 per hour. T. Right. Whereas if you can delegate that to somebody else, like an executive assistant, now, you can focus more of your time on doing the stuff that you would qualify as $2,000 per hour.

Richard Hill [00:15:04]:
Yeah. Yeah. So, yeah, it's, yeah, it's actually something that I've just done and I've just obviously, you know, you know, Mads and Yanis, obviously they have an outsource and they have a recruitment company and I've got a, a job description with them. Right now they're hiring my, my executive assistant right now, or inter. I was quite interested in your, in your, your take on that. But yeah, so obviously that's freed up a lot more time for you to focus on, on the hiring, on, on the big value tasks of speaking and so forth. Yeah. Now when I look at your website, you know, and obviously listen to you speak, culture is a big part of the way of yourself and the way that you run your business.

Richard Hill [00:15:46]:
But I'm intrigued how you are able to sort of main that maintain that culture and some of the, some, some of the day to day things that you do with you being fully remote, obviously. 130 people, fully remote. You know, it looks like a great place to work, you're doing some great work, you've got some great clients. You know, what are some of the things you do to maintain that culture as an agency?

Jason Hennessey [00:16:06]:
Yeah. So I think, you know, culture is one of those things. Like you can kind of say that you've got like a culture.

Richard [00:16:14]:
Right.

Jason Hennessey [00:16:14]:
You can, you can say that these are our core values.

Richard [00:16:17]:
Right.

Jason Hennessey [00:16:18]:
And you spit out a couple big words.

Richard [00:16:20]:
Right? Yeah.

Jason Hennessey [00:16:21]:
But if you're actually truly not living the core values, you know, like, like I think people can notice that, especially your employees.

Richard [00:16:29]:
Right.

Jason Hennessey [00:16:30]:
And so, you know, we, we truly live and die by the core values that we set forth. You know, one of them is, you know, have fun, don't be a jerk.

Richard [00:16:39]:
Right.

Jason Hennessey [00:16:39]:
You know, I fired a client because they were being a jerk to, you know, a couple of our staff members. And this was a big client and I took the initiative to jump on a call and I ended up firing the client. And that went a day for the whole team.

Richard [00:16:52]:
Right.

Jason Hennessey [00:16:52]:
Just because it took the CEO to recognize that this client wasn't living within our core values that we believe in. And so let's get that toxic, toxic, you know, area out of, out of the business.

Richard [00:17:05]:
Right.

Jason Hennessey [00:17:05]:
So when they see that it's coming from the top down, but also from the bottom up, that's kind of what builds the, the culture. Other things that we've done is we've hired, you know, senior VP of, of people's success. And so her whole mission is to, you know, to make sure that we actually make the lives of our team members better. You know, as we get more resources and more budget, what can we do to kind of, you know, to, to strengthen, you know, the, the lifestyles of our, of our team. And so I believe in the model of like, if you really take good care of your team first, that's priority number one.

Richard [00:17:44]:
Right.

Jason Hennessey [00:17:45]:
Then they will help you take care of your clients. And that's the definition of a successful company, in my opinion.

Richard Hill [00:17:52]:
Yeah, no, I, I'm with you on that. I saw the, I think I saw a post maybe a couple of months ago where you'd fired a client for being a jerk, as you put it. Yeah, yeah, yeah. And obviously your team respect that. They're obviously dealing with that client, customer firm on a day to day basis and having to deal with, you know, maybe, you know, completely unreasonable behavior, which is just obviously against your culture, against your values. Absolutely. Yeah, yeah. Obviously demonstrates to them, doesn't it? Oh, Jason actually does give a damn about these values.

Richard Hill [00:18:24]:
You know, he's fired this client based on the fact that they're a, you know, we would call it knobhead probably in the uk. But.

Richard [00:18:34]:
Yeah.

Richard Hill [00:18:35]:
Okay, so no, great, thank you for that. So let's change of direction for a minute. AI. You know, I'm really, I'm really intrigued, you know, what Hennessy Digital, what you guys are doing in terms of sort of adopting AI, sort of one for clients, you know, there's the client side, obviously search is changing or changed. I would say it's probably, you know, it's changed and where we need to be for clients and you know, and the visibility for clients that side. But then also how and what you're doing within your agency to maybe streamline operations with AI.

Jason Hennessey [00:19:10]:
Yeah, you know, I think, you know, it's, it's something where change is the only constant.

Richard [00:19:17]:
Right.

Jason Hennessey [00:19:17]:
You know, and so you either look at AI as a, as a threat or an opportunity.

Richard [00:19:23]:
Right.

Jason Hennessey [00:19:23]:
I think if you are looking at AI as kind of like a threat, you know, you're going to quickly find yourself out of business.

Richard [00:19:29]:
Right.

Jason Hennessey [00:19:30]:
And so for us, you know, we, we embrace change. You know, we're always at the forefront of, of new tools and new Technologies. And you know, and, and so, you know, we, we even had do something internally, we call it our own hackathon, where we basically give our engineering team like you know, a couple days to kind of innovate and to come up with new technologies that will make our performance either more efficient or more effective.

Richard Hill [00:19:58]:
Yeah.

Jason Hennessey [00:19:59]:
And so sometimes, you know, big ideas come alive as a result of that. You know, one of which was we built a, it's called HD Translate. And so this was basically developed during one of our hackathons where a couple of our engineers kind of came up with this concept. And, and so we were able to basically take a full website and translate it into multiple languages where it basically keeps the same internal link structure. You know, it's, it adds all of the correct schema, it adds all of the correct hreflang tags, all of that kind of stuff. And so now basically, if you've got 2,000 pages in English, it automatically will basically convert the website and actually build out a ES subfolder if it's in Spanish. And I've got 2,000 pages in Spanish. Right.

Jason Hennessey [00:20:49]:
And so that's kind of like the result of us kind of always looking to kind of be innovative. The other thing that I like to do as well is I don't pretend to be the smartest person in the room and I don't pretend to always have the smartest people in the industry that work for me. And so, you know, I have a budget to go out and, and to bring in outside people. I call this outsourcing genius.

Richard [00:21:16]:
Right.

Jason Hennessey [00:21:17]:
And so I will bring in outsiders that are world class, that's something different, and get them to come in and maybe audit our work or come up with a different way of doing things. And so, you know, you know, a lot of times people don't, they have big egos and they can't appreciate that. You know, sometimes it might take an outsider that you can't afford on the market to come in and kind of give you new ideas.

Richard [00:21:40]:
Right.

Jason Hennessey [00:21:40]:
So just being open to, to change and bringing in additional resources, you know.

Richard Hill [00:21:47]:
Bringing in maybe once a month, month, once a quarter, different expertise, that's not, not an existing team member, you know, somebody to do a project, a piece of work, to audit a piece. And look at how we're doing technical audits, or in this case, what can we do with agentic AI, for example, or what can we, can we build? We might, we've got the experts, but they may be really busy doing their, doing the day job, looking after clients and very Busy. Let's not miss this opportunity. So engage a team of experts or an expert. So you're always on the lookout for those people. Then when you're at events and listening to speakers, oh, that guy's. That, that guy's a smart guy. As hard.

Richard Hill [00:22:28]:
Let's see if we can hire him for a week or for a project and 100.

Jason Hennessey [00:22:32]:
Yeah. Anytime I see somebody that writes a really inspirational like LinkedIn post, I'm like, flag it. You know, let me reach out to this person. Let me at least get to know them a little bit and potentially how could we maybe leverage their skill set, you know, to help our clients have a better experience?

Richard Hill [00:22:51]:
So, so we're bringing experts in. We're, we're doing the, you know, the hackathon. I like that. You know, sort of almost gamifying, creating new things and experience, experimenting with different things. But in terms of, say, AI and the way that obviously people are maybe searching for a lawyer in a certain city in America, in the U.S. you know, what are you, is there anything you're doing specifically? It's probably more SEO focused. But what are you doing in terms of, have you had to sort of change your approach this last 612 months in terms of strategy for SEO? And obviously the index looks quite a lot different now with different AI overlays, overviews.

Jason Hennessey [00:23:32]:
Sure, yeah. You know, I think, you know, the. What I'm noticing early on. Right. And it's still, this is only like the first inning of, of what we're about to see. This is the worst it will ever be in terms of AI. You know, it's always going to just kind of continuously get a little bit better and a little bit better.

Richard [00:23:50]:
Right.

Jason Hennessey [00:23:50]:
But, but when I kind of peel back the layer of that onion, I. What I'm noticing is that, you know, AI is built upon best practice SEO.

Richard [00:24:01]:
Right.

Jason Hennessey [00:24:01]:
And so, yeah, whether or not we call it SEO in the future or whatever.

Richard [00:24:07]:
Right.

Jason Hennessey [00:24:07]:
That's very debatable. And it's a topic of, you know, debate now amongst the industry, but it's all predicated upon best practice SEO. And so, you know, when I, you know.

Richard [00:24:20]:
Sure.

Jason Hennessey [00:24:20]:
Are we getting a lot more efficient, you know, with our team, you know, are we able to kind of write and edit more content and publish more content for our clients now with AI? Yes, 100%. You know, are we able to automate certain things that we had to do very manually in the past? Yes, for sure. Like, and so it's a game of inches. And so, you know, I'm just allowing My team to come up with better ways within their own respective departments to leverage AI, you know, whether it's accounting or whether it's link building or whether it's operations. And we're very open and receptive to, to, you know, change, you know, and, but it's not just like, hey, let's just like change our systems and processes today. And then all of a sudden there's a new tool like next month like that you can put yourself out of business if you start innovating quickly. And so, but, but we're very open and, and very agile company. Yes.

Richard Hill [00:25:24]:
I think this is the thing is that people have been doing this a while, obviously you've been doing this a long while. It's just SEO, isn't it? It's changing, it's moving and, and the latest and greatest is AI within that. Obviously it's a massive opportunity, but it is very much, you know, no doubt, while you're still very much at the forefront of what you do, because you're adapting. No matter what is happening in the industry, if it's not AI, it'll be something else that's changing search, you're just adapting, you're investing, you've got people that are doing your hackathons, you're bringing expertise in to test, to try. Yeah, it's exciting though, isn't it? I find at the moment we're doing a similar thing where we're doing what we call the AI Games, our four departments within our business. We've given them X amount of time and we're sort of gamifying the four departments. And then in about six weeks time, we're gonna have a half a day where we get the whole company together and for sort of captains of those teams will present their ideas around what they've built with AI to help their department. So that's quite exciting as well.

Jason Hennessey [00:26:25]:
Yeah, it's very similar. It's like what we're doing. Yeah. So, yeah, that sounds like you're on the right track there for sure.

Richard [00:26:30]:
Yeah, yeah.

Richard Hill [00:26:32]:
So obviously I'm aware of yourself from speak. From your speaking engagements, you know, and from there, obviously saw you speak in Vietnam, then I saw you speak in Chiang Mai. And I think it's a good topic to cover in on an agency podcast about sort of personal branding. Agency owners, you know, I think quite a lot of agency owners are, you know, they've got their head deep in the work, you know, and they're maybe not as, you know, they know they should speak more, they should do more, but they maybe don't, you know, I'm probably one of them, to be fair. You know, I'm quite, I'm quite happy behind the scenes, but I know that I should put myself forward a little bit more. You know, how's your personal brand really contributed to the agency's success, would you say? Firstly?

Jason Hennessey [00:27:15]:
Yeah, I think that's been a big part of, of our growth.

Richard [00:27:19]:
Right.

Jason Hennessey [00:27:20]:
And it's not like, you know, every story has to have somebody that has a personal brand that's kind of leading the pack. There's a lot of successful agencies that, you know, don't have, you know, a figurehead, if you will, that's kind of like, behind it. But for me, you know, I, I enjoy this. You know, I, I, I get a lot of compliments, you know, on some of the, the talks that I do, and so that gives me more energy to do more of it. And so, you know, I just kind of just leveraged that. And, and I enjoy speaking, like, you know, to you, like, Richard. I enjoy jumping on podcasts and stuff like that. And, and you never know, like, who's listening.

Richard [00:28:03]:
Right.

Jason Hennessey [00:28:03]:
You know, yeah, there's, there's two different sides that can come from this.

Richard [00:28:07]:
Right.

Jason Hennessey [00:28:08]:
You know, somebody might be listening to this podcast right now, and they're like, in their early days of, of, you know, building an agency. And so, like, the stuff that we're talking about hopefully can inspire them to kind of get to the next level.

Richard [00:28:23]:
Right.

Jason Hennessey [00:28:23]:
You know, that's, that's option 1 1. And then the other side is like, hey, you know, maybe, you know, they reach out to you or they reach out to me and they want to work with us too. Right? That's the other side of this.

Richard [00:28:34]:
Right.

Jason Hennessey [00:28:35]:
And so, yeah, so, you know, it's just, you know, it's just been, it's been a good journey, you know, writing my book was also a big instrumental part of that, help build out a personal brand within my niche. And I wrote a second book. And so, but, yeah, personal branding for me has been a key part of the growth for sure.

Richard Hill [00:29:00]:
How long did it take you to write the books then?

Jason Hennessey [00:29:02]:
So the first book took about 18 months, start to finish, so that one was long. The second book, which was basically an abridged version of the first book, because the first book was very specific targeting, like, law firm owners. It was called Law Firm SEO.

Richard Hill [00:29:22]:
Yeah.

Jason Hennessey [00:29:22]:
The second book was called Honest SEO. And I, I figured, I wrote, I spent so much time writing this first book that a lot of this stuff is really applicable to Any small business. So let me just kind of, you know, write an abridged copy of law firm SEO and kind of make it so that if you're a E commerce agency owner, if you're a. Any type of other business, it'll be applicable to you. And so that one took a little quicker than the first one.

Richard Hill [00:29:45]:
Yeah, yeah, I think it's a, it's a real good. It's obviously a real position in piece, isn't it? A book. You go to an event or, you know, you're the author that they find via Amazon or wherever it may be, or you go to an event and you know, have you got my latest book sort of thing. It's like, not everyone's going to have a book, are they? Where obviously most industry, most industries or most agency verticals are quite crowded. No matter what you're doing, really. Obviously, if you've got the book, you've got the podcast or you're on podcast, it's differentiates you from, from a lot of other people.

Jason Hennessey [00:30:16]:
Yeah, yeah, it's that. But it also has the SEO impact too because like, as we all know, like eat signals are very strong.

Richard [00:30:23]:
Right.

Jason Hennessey [00:30:24]:
Expertise, authority and trust. And so, you know, when you have a book, then it helps you qualify more for a knowledge panel. It helps you to get on more podcasts. And those are all the signals that, you know, that we all know that Google is looking at, and not just Google, a lot of the AI overviews too. You know, like they're all looking at the same data points too.

Richard [00:30:42]:
Right.

Richard Hill [00:30:42]:
So yeah, that's where a lot of the, you know, they're looking for higher authority sites, aren't they, to build those overviews. So obviously if you're, if you're an author. And that's a great signal, isn't it?

Jason Hennessey [00:30:52]:
Yeah, yeah, that's exactly right.

Richard Hill [00:30:54]:
Okay, so what would you say? So obviously spoken I don't know how many times, but probably hundred times, hundreds of times. Written a couple of books.

Jason Hennessey [00:31:04]:
Yeah.

Richard Hill [00:31:05]:
Maybe could you share like a, a story of maybe where maybe you spoke and some amazing opportunity came from it. You know, like I always like to hear these sort of. Well, I did this talk and you know, and I thought that was it. But then about two years later, it just so happened somebody was in the audience that, you know, is, is it like you got any stories of sort of crazy stories for opportunities?

Jason Hennessey [00:31:26]:
Yeah, there's been, you know, there's been a lot of stories, you know, small and big. And I think I gave a presentation in, I want to say it was like South Carolina. It was to a group of lawyers. It seemed like a small group of lawyers. And, you know, I ended up meeting one of our biggest clients, you know, at. At that event that turned into, you know, over a hundred thousand dollars per month in recurring revenue just from, like me giving a presentation, you know, so that. That talk about the ROI of a speech. Speech, you know, that's very powerful.

Jason Hennessey [00:32:03]:
And then there's also times where, you know, you know, I've been on a plane, you know, sitting, you know, in. In. In my seat, and I look over and there's somebody reading my book. You know, like a couple rolls up.

Richard [00:32:16]:
Right.

Jason Hennessey [00:32:16]:
You know, you know, that. That's very rewarding when you kind of see the universe, you know, receptive to, you know, your. So that's.

Richard Hill [00:32:27]:
That's incredible, isn't it? Yeah. So you sat there on a plane, just minding your own business. You look across. Yeah, somebody's reading your book.

Jason Hennessey [00:32:36]:
Yeah, it was a. It was a bright red bug. And I'm like, that looks like, oh.

Richard Hill [00:32:40]:
It is my book.

Jason Hennessey [00:32:43]:
And then we ended up. I ended up going up to him when we got off the flight. I'm like, that's an amazing book. He's like, yeah, like I wrote. It took me 18 months to write that.

Richard Hill [00:32:51]:
I bet he couldn't believe it.

Jason Hennessey [00:32:53]:
It. He's like, no way. And it's like.

Richard Hill [00:32:55]:
I'm like, he's like, looking for the picture. Your picture was on the back. Was it? So it's on the back.

Jason Hennessey [00:32:59]:
Exactly.

Richard Hill [00:33:01]:
That's brilliant. So there you go, listeners, I think, obviously putting yourself out there, speaking at events, you know, we say this a lot on a lot of episodes, but speaking at events and obviously writing a book, you know, you know, it's a brilliant, brilliant way to position yourself. So obviously started, you know, that those first few clients back In, I think, 2008, you said, you know, to now, you know, 130 people. You know, business is good, good. But what I'm interested to talk about is when things get a little bit hard, things get a little bit tough, you know, and I think, you know, have you ever sort of experienced sort of burnout, a real tough time, you know, how did, you know? How did you navigate that?

Jason Hennessey [00:33:40]:
Yeah, that's, you know, that that's all par for course in terms of business, especially agency. You know, I remember. I remember one time I had a client call me up and they're very upset. I don't know, something happened with the website and, you know, and whether it was a form or something, right? Something ended up breaking on their website. And so the client called me up and he's like, blah, blah, blah, blah, blah, right? Yelling, yelling, yelling, yelling, yelling, right? And then I'm just like, I'm so sorry. Let me figure this out. Let me.

Richard [00:34:15]:
Right?

Jason Hennessey [00:34:15]:
And then basically, like, I hung up, and I'm just like, what the heck just happened?

Richard [00:34:20]:
Right?

Jason Hennessey [00:34:20]:
So then five minutes later, the client calls me back and he's like, look, I. I owe you an apology. And I'm like, why? He goes. He goes, look, I get it. I worked with so many other agencies. He goes, 99 things can go, right, right? But when that one thing goes wrong, that's when you hear from me. He goes, that's not fair. He goes, I owe you an apology.

Jason Hennessey [00:34:45]:
You know, like, you've been a great partner of ours, and I appreciate what you guys do. And I was just irritated because I woke up and I realized form was broken. But, you know, for everything else that you guys do, I appreciate if we could just kind of get that one thing fixed, that'd be great. And it's the truth, right? Because owning an agency, you could have 99 things going well, right? Everything's great. You know, like, your traffic is up, the leads are up.

Richard [00:35:08]:
Right?

Jason Hennessey [00:35:08]:
But the moment, like, a form breaks on a website or something like that, it's like. It's almost like it's a fireable offense.

Richard [00:35:15]:
Right.

Jason Hennessey [00:35:15]:
You know, and so, yeah, it's very. It's a very stressful world to live in when you own an agency, Right? Because there's so many variable, so many moving pieces.

Richard [00:35:27]:
Right?

Jason Hennessey [00:35:27]:
And so. And. And a lot of times it's outside of your personal control.

Richard [00:35:32]:
Right?

Jason Hennessey [00:35:33]:
It's. It's not your fault.

Richard [00:35:35]:
Right.

Jason Hennessey [00:35:35]:
And so we live in a world of. Of abundance here at Hennessy Digital. And, you know, we. We don't fire people for making, like, mistakes. You know, if they make a mistake, in most cases, it's a. It's a.

Richard [00:35:51]:
A.

Jason Hennessey [00:35:51]:
It's a process problem.

Richard [00:35:53]:
Right.

Jason Hennessey [00:35:53]:
It's not necessarily a people problem.

Richard Hill [00:35:55]:
Yeah.

Jason Hennessey [00:35:56]:
And if we put processes in place and a human being makes a mistake, again without following the process, then that becomes a people problem.

Richard [00:36:06]:
Right.

Jason Hennessey [00:36:06]:
Because they're not following the process.

Richard [00:36:08]:
Right.

Jason Hennessey [00:36:08]:
And so in those cases, if people continue to not follow the process, right. Eventually they end up on a pip, and they might end up, like, not working here longer.

Richard [00:36:18]:
Right.

Jason Hennessey [00:36:18]:
You know, but. But a lot of times we recognize, we appreciate and reward when people actually, you know, make some mistakes that forced us to improve our processes, you know.

Richard Hill [00:36:29]:
Yeah, yeah, I think, I think, you know, in both the talks I saw you do, you, you sort of talked about your own sort of, you know, obviously working very, very, very, very hard. You know, and maybe, you know, I've been through those times where you sort of maybe neglect yourself because you're so busy, you know, looking after your team and trying to pay the bills and so forth. What are maybe some things you do now when you're for yourself outside of Hennessy Digital Digital that sort of keep you on the straight and narrow and you know what, some of your hobbies and some of the things you do when things are a bit tough and you want to get away from the office.

Jason Hennessey [00:37:03]:
Yeah, I mean I'm a, I'm a family man and so I spend so much time, you know, with my kids and traveling. You know, just like you mentioned earlier, where you take, you're taking your son to, to Chiang Mai, right? Or you took him already?

Richard Hill [00:37:19]:
Yeah, one last year, then taking another this year.

Jason Hennessey [00:37:22]:
Yeah, yeah, that, that's the most rewarding thing I think that, that I get the greatest pleasure from is being able to kind of see the world again through my kids eyes and so getting on a plane and traveling. In fact, me and my, my son Zach are coming out to Manchester. I'm not sure if that's close to you.

Richard Hill [00:37:41]:
Yeah, Yep.

Jason Hennessey [00:37:44]:
So I'm coming out to Manchester to do a mastermind with a couple high end SEOs and so my son and I are gonna fly out there and we're gonna spend some time. My son's actually gonna do a semester abroad in London and so we're gonna go to London and tour the school and so like that's the kind of stuff. I just took my daughter to a Katy Perry concert and my son. So that was just this past weekend. So that's really where I filled the gaps in on some of my personal time. Like that.

Richard Hill [00:38:17]:
I love it. I love it. That's. Yeah, I think, you know, it's trying to get those weeks away with the family or booking some real memorable trips. Obviously I saw you, like I said it a couple of times, but obviously you're with your family in Chiang Mai about six, seven months ago. Obviously that's a beautiful part of the world. My favorite, one of my favorite parts of the world anywhere. Southeast Asia, isn't it?

Jason Hennessey [00:38:41]:
We took, we took 36 days to travel like Asia to. We ended up in Bali, we were in Chiang Mai, we went to Phuket, we went to Bangkok, we went to Japan, Tokyo. So like Singapore, right. I spoke at the agents conference. Yeah, we did all of that within like 36 days, you know, and my business was growing without me traveling.

Richard [00:39:07]:
Right.

Jason Hennessey [00:39:07]:
And so that's kind of like the goal is when you, you know, can actually take 36 days, travel the world, do something that you love.

Richard [00:39:15]:
Right.

Jason Hennessey [00:39:15]:
And the business is still growing behind the scenes.

Richard Hill [00:39:18]:
Yeah, that is the, that's the dream, isn't it? I think everybody listening to be able to have that freedom to have those, be able to sort of commit to those experiences, whether it's, you know, with your family or go and do things that you want to do. But then the business has got system process people in place to then continue to grow. When you get back here, did you. So when you, when you were away, did you do like a weekly call with your COO or how, how do you manage that?

Jason Hennessey [00:39:43]:
So, you know, there really wasn't much, like, I, I, you know, because my assistant was checking my emails, right. You know, there's nothing on my calendar for that period. And so, so if something, like, I've got a really good system with my email, right? So, like, if, if something ends up in an Immediate Attention folder, right. If something, something happens, comes in my Immediate attention, then she'll give me a call or she'll send me a text message and then I'll jump on. But for the most part, if nothing is ending up in my immediate Attention folder, you know, I'm free to kind of do what I need to do.

Richard Hill [00:40:15]:
Yeah, yeah. No, I love it. I love it. So, well, well, so, last few questions. Jason, so you spoken a bit about Vivid Vision for your company. Can you elaborate more on that concept and how it's guided the agency?

Jason Hennessey [00:40:30]:
Yeah, so that was a concept again from my, my executive coach, Cameron Herald. He wrote a book called Vivid Vision. If you're listening to this, I highly recommend you getting it on Amazon, reading it, implementing it, you know. And he kind of describes Vivid Vision as like, you know, when you're building a business, you know, if, if I were to ask you, Richard, like, you know, so where do you see your company in three years? You know, I mean, like, you'll be able to kind of tell me, like, you know, we're gonna be here, we're gonna have this many people, we're gonna have this, you know, many clients.

Richard [00:41:01]:
Right?

Jason Hennessey [00:41:02]:
But you know, that story might change if another person asks you, like, next week, right? So, like, you have to kind of like document what your Vivid Vision is, right? And so once you document it, right, Then everybody in your entire Organization can see it. You know, all your clients can see it, all your partners can see it. You know, everybody.

Richard [00:41:22]:
Right.

Jason Hennessey [00:41:22]:
And all your staff especially, because they have to help build the vision.

Richard [00:41:25]:
Right.

Jason Hennessey [00:41:26]:
And so I highly recommend, you know, going out and documenting what your, your company is going to look like in the next three years. And our vivid vision is on our website, hennessy.com you can see it. I think it just says where we're going. And so. And so even if you only accomplish 20% of the vivid Vision.

Richard [00:41:47]:
Right.

Jason Hennessey [00:41:47]:
That's still considered success.

Richard Hill [00:41:49]:
Yeah, that's great. For obviously, clients looking at your aspirations, your team, obviously they're working for and part of a company that have got this vision, this very big vision, maybe, or this type of vision that they very much might want to be part of. And you know, I guess for those that have seen the Vivid division maybe three, four years ago and to see the vision that you and the leadership have sort of put out there, and then three, four years later, it's, it's coming true and, and they're like, oh, wow. Yeah, yeah, yeah.

Jason Hennessey [00:42:19]:
Manifestation is real. Yeah, like, and this is just a form of documenting, like manifestation.

Richard [00:42:25]:
Right.

Richard Hill [00:42:26]:
So, yeah, yeah, great. No, I love that. I'm a big, big believer in sort of sharing with the wider team the vision and what we're planning and what you're planning to do with the agency. You know, obviously get, buy in, get people on board. They can sort of understand what they're maybe part of in your, in your instance, 130 people.

Richard [00:42:44]:
Yeah.

Richard Hill [00:42:45]:
In theory it could be easy, ish. To get lost in that big organization. But if you now know that this work that you're working on is part of the big vision. Yeah, it's going to be quite inspiring. Yeah, that's right. So you talked about mentors, you mentioned the chap who wrote Vivid Vision, but any other mentors that you've had over the years that have sort of really helped you?

Jason Hennessey [00:43:07]:
Yeah, I think there's many. I mean, every time I kind of open a book and I, and I read a podcast or I listen to a podcast, you know, I'm always kind of getting inspiration from people, you know, as far as, you know, mentors, I'd say, like, my, my grandfather was probably my biggest mentor in my life. I really didn't have a father figure in my life. And so my grandfather kind of filled that kind of gap. Very humble man. He was a custodian in a high school and so didn't make a lot of money, but, you know, gave me A lot of my. A lot of my. My drive, he gave, you know, he showed.

Jason Hennessey [00:43:47]:
Showed me the right way to treat others and respect and manners and ethics and all that stuff. And so, like, you know, I think you're. You're based upon, you know, your character and how you show up in the world. And I, I think he's a testament to the character that I am because of the way I was raised. And so, because I, I didn't come from a lot of money, you know, that gave me all the drive that I needed, all that hunger to go out and to prove, you know, that I can kind of build this. And so that's. That's been the mission that I've been on. And.

Jason Hennessey [00:44:24]:
And so, yeah, a lot of that is a testament to my grandfather who was pro first mentor and I didn't know it at the time.

Richard Hill [00:44:30]:
Yeah, that is lovely. Thank you, Jason, for sharing that. Thank you. So I think we'll last couple of questions and then I'll. I'll let you go. So, fellows, that. Looking to scale, you know, I think, you know, we talk about, you know, in our agency and at the agency, incentive, you know, hitting these plateaus of, you know, whether it's, you know, we've hit the million, but we're struggling to get to the, you know, one and a half, 2 million or hit the 5 that we've, you know, we've been doing half a million a month for the last three years. We just can't seem to move the needle.

Richard Hill [00:45:01]:
You know, what are maybe a couple of bits of advice that you would give to agency leaders about really sort of going past that next plateau? Through that plateau.

Jason Hennessey [00:45:12]:
Yeah. So. So for me, like, when we got to like, 5 million, you know, I, I didn't even know how the heck we ended up there. You know, truthfully, it was all kind of an accident, like, you know, that we didn't really set goals. Like, it was just like we just showed up every morning and we just kind of got to work. Yeah, but going from 5 to 10 million, like, I knew that I did not have a plan for that and I. That's the time to make a lot of mistakes. And you could probably put yourself out of business by, you know, because now it's dangerous.

Jason Hennessey [00:45:43]:
You've got a lot of money coming in, you know, and if you don't execute it correctly, you know, you can make some very critical mistakes.

Richard Hill [00:45:50]:
Yeah.

Jason Hennessey [00:45:50]:
So that was the time that I ended up bringing in the coach.

Richard [00:45:53]:
Right.

Jason Hennessey [00:45:54]:
And finding like a business coach that can kind of show you the way. So I think if you're at 5 million, you're trying to get to 10 million, or you're 1 million, trying to get to 3 million. You know, maybe go out and try to find somebody that's already done that. Yeah, right. That can give you the Cliff Notes and the shortcuts on what to do, but more importantly, what not to do.

Richard [00:46:14]:
Right.

Jason Hennessey [00:46:15]:
That's where I think you get the biggest reward with having a coach is them telling you what not to do and talking you out of things and holding you accountable. Somebody to hold you accountable.

Richard [00:46:26]:
One.

Richard Hill [00:46:26]:
Yeah. Give you a bit more of a straight line. Yeah. Rather than make a few, few too many mistakes. Maybe that, like you say, when you're at the bigger numbers, you know, you make some big mistakes, it can be, you know, quite fatal, can't it? If you potentially lose. Lose a lot of cash flow, lose some big clients, lose big team members. You're not working on the culture, you just focus completely on the revenue. Yeah.

Richard Hill [00:46:50]:
It's like a balance. Yeah, yeah. So, yeah, yeah. Lovely. So, Jason, it's been an absolute pleasure having you on the show. I like to finish every episode with a book recommendation. Do you have a book to recommend to our listeners?

Jason Hennessey [00:47:04]:
So one of my favorite books, actually, is a book called Rework. It's by Jason Freed and his partner. They, they wrote the book. It's, it's, it's very short chapters. There's a lot of visual, kind of like illustrations, but it's just short, concise, but impactful.

Richard [00:47:26]:
Right.

Jason Hennessey [00:47:27]:
So you feel a sense of accomplishment when you read like a three page kind of chapter and it's just like, no fluff. This is like, here's the bang.

Richard [00:47:35]:
Right.

Jason Hennessey [00:47:36]:
Just take it. Let's move on to the next chapter. And I just thought that was just very, like, inspiring. And so that was kind of how I modeled my book. When I wrote my book, I just wanted to kind of give more bang to the investment.

Richard Hill [00:47:51]:
Yeah, yeah, no, great. We'll. We'll hook that up in the show. Notes. Well, thanks for coming on the show, Jason. For those that want to find out more about you, more about Hennessy Digital, what's the best way to do that?

Jason Hennessey [00:48:01]:
Yeah, so I'm pretty active on LinkedIn. Be sure to follow me on LinkedIn. Also, I do a lot of video content on Instagram and, and you could check us out@hennessy.com h e n e s s e y.com well, thank you.

Richard Hill [00:48:18]:
So much and no doubt I may see you again somewhere in Southeast Asia. Over the coming. Coming year or so or maybe in Manchester in a few months time.

Jason Hennessey [00:48:26]:
Sure, Yeah. I look forward to it.

Richard [00:48:27]:
Yeah.

Jason Hennessey [00:48:28]:
Thank you for having me, Rich. I appreciate it.

Richard Hill [00:48:29]:
Nice one. Thank you. Cheers.

Richard [00:48:32]:
Cheers.

Richard Hill [00:48:35]:
If you enjoy this episode, hit the subscribe or follow button. Wherever you are listening to this podcast, you're always the first to know when a new episode is released. Have a fantastic day and I'll see you on the next one.

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