Building a Lasting Agency in a Digital World with Andrew Eklund

Andrew Eklund is the Founder of Ciceron, a digital agency established in 1995 that has been at the forefront of the online marketing industry, helping brands navigate the complexities of the digital landscape. Ciceron is celebrated for its innovation and recognized as one of the fastest-growing digital agencies by AdWeek, Inc. 5000, and the Business Journal’s Fast 50, highlighting significant contributions to the field.

Currently, Andrew is steering Ciceron through another evolutionary leap by integrating AI technology to enhance marketing strategies and customer engagement. A seasoned speaker, Andrew has shared his expertise at industry-leading events such as Digiday, MediaPost Summits, and the Governor’s Conference on Tourism in Las Vegas, among others.

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Here’s a Glimpse of What You’ll Hear:

  • [2:26] Andrew Eklund on how his childhood influenced his entrepreneurial traits
  • [4:13] How lessons from his father shaped Andrew’s leadership skills
  • [6:41] The breakthrough recognition of the web’s potential and the founding of Ciceron
  • [8:06] Insights into early digital agency challenges
  • [10:32] Andrew shares personal observations on AI’s impact on advertising
  • [14:43] How adapting to new technologies like digital marketing post-2000 shaped agency growth
  • [19:33] Regrets and reflections on missed tech opportunities
  • [24:36] Navigating economic crises with resilience and strategy
  • [29:24] AI’s potential to automate mundane tasks, freeing time for creativity
  • [34:42] Embracing artificial intelligence in marketing and the transformative impact on client results

In this episode…

In today’s fast-paced digital landscape, agencies and entrepreneurs often struggle to adapt to rapid technological changes and market shifts. These challenges can lead to missed opportunities and potential business downturns, especially when economic crises hit. The ability to pivot and innovate while maintaining resilience is crucial for survival and success in this volatile environment. But how did these elements combine to ensure the agency’s success over the years?

Andrew Eklund’s story begins with his early exposure to entrepreneurship, influenced by his father’s leadership roles and his youthful ventures. His agency, Ciceron, established at the dawn of the internet era, has navigated through the dot-com bubble, the 2008 financial crisis, and the recent COVID-19 pandemic by continuously reinventing itself and embracing new technologies, notably AI. Andrew’s leadership and forward-thinking approach have allowed Ciceron to remain at the forefront of the digital marketing industry, adapting to changes and seizing opportunities to grow. A significant part of their evolution involved making tough decisions during economic downturns while understanding the importance of empathy towards employees and clients alike.

Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Andrew Eklund, Founder of Ciceron, about building an agency that will last for decades. Andrew reflects on how hustling from childhood shaped his entrepreneurial spirit and discusses the transformative shifts in the digital pre-press industry. He also delves into the significant impacts of economic downturns on digital marketing strategies, and leveraging AI in digital marketing and entrepreneurship.

Resources Mentioned In This Episode

Related episode(s):

Quotable Moments:

  • “A job is that you just go and you are a leader.”
  • “This is now our turn. We’ve been displacing people for 25 years… Now it’s happening to us.”
  • “Nothing like running an agency… we’re the first to go when times are bad and the last to come back when things are getting good.”
  • “We’re going to fill in with technology and these people that are amazing already are just going to be more amazing here.”

Action Steps:

  1. Cultivate a culture of innovation within your organization to adapt to emerging technologies like AI.
  2. Surround yourself with a solid peer network of industry professionals to navigate both triumphs and challenges.
  3. Maintain a learner’s mindset and be willing to pivot your business model in response to technological advancements.
  4. Incorporate empathy, humility, and kindness into your leadership approach, as shown by Andrew Eklund’s father.
  5. Use AI and automation to eliminate repetitive tasks, allowing your team to focus on high-value, strategic work.

Sponsor: Rise25

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We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Google Podcasts. We’ll also create a copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPO, EO, Lending Tree, Freshdesk,  and many more.  

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

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Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

Episode Transcript

John Corcoran 0:00

All right, today we’re talking about how to build an agency that will last for decades, literally decades and how you need to reinvent yourself along the way. My guest today is Andrew Eklund. I’ll tell you more about him in a second. So stay tuned.

Chad Franzen 0:16

Welcome to the Smart Business Revolution Podcast where we feature top entrepreneurs, business leaders and thought leaders and ask them how they built the relationships to get where they are today. Now, let’s get started with the show.

John Corcoran 0:33

All right, John Corcoran here. I’m the host of the show. You know, every week I get to talk to smart CEOs, founders and entrepreneurs from all kinds of companies. We’ve had Netflix and Kinkos YPO, EO activation, Blizzard, redfin GrubHub, lots of more in the archive. So go check out those archives. We’ve also had many agency leaders, thought leaders and founders on this show, Carl Smith at Bureau digital David C. Baker, Roger Hurney off Madison Ave. Go check out those archives. Lots of great episodes, search for the term agency on my website smart business And you can find it there. Of course, this episode brought to you by Rise25, where we help b2b businesses get clients referrals and strategic partnerships we’ve done for you podcasts, and content marketing, and you can check out our new platform, podcast copilot, go to, or email us at support at And a quick shout out to Peter Garretson of tan worldwide past guest on my show, who recommended today’s guest some of our best guests come from recommendations from other guests. 

Andrew Eklund is the Founder of Ciceron it is a digital agency established in get this 1995, one of the first web agencies in the United States, I want to know how you remain motivated continuing to run the company for all this time, we’re going to definitely ask him about that it’s been recognized. The agency has been recognized as one of the fastest growing agencies by Adweek and other publications. And it also now is really embracing AI. So that’s really fascinating is being at the forefront of the development of the web. Now the development of AI so we’re gonna talk about that as well. But Andrew, I always love to start people back in their childhood, and you had a father who was a leader for you and your brother, and you turn out to be entrepreneurs. And that was a bit of an inspiration for you and you went out on paper routes. And so Cutco knives tell us about those origins.

Andrew Eklund 2:26

Yeah, I think the hustle was always just sort of a part of things. But my dad was much more of an academic hustler. And my brother and I became sort of the more, shall we say, commercial hustlers. But my dad, my dad was a political science professor at a small liberal arts college here in Minnesota, and he became chair of that department when he was very young. Then he became the mayor of the city that that college was in.

John Corcoran 2:52

And then he was political science if he worked his way into becoming mayor.

Andrew Eklund 2:57

Yeah, but he was married when he was like, 29 years old, you know, and from that, and then he got, and then he got plucked by the governor of the state of Minnesota and was there and then became a CEO through a relatively quick thing. And he’s out he was always involved in older or older adult care, and so forth. And my brother and I just, I guess, grew up just thinking that’s what a job is, right? Like a job is that you just go and you are a leader. And you, we are just those things that were around us all the time. But I think that there’s so that’s the upside. The downside is I think, you know, I learned fairly early on that I’m very independent. And I think I was put on probation, twice for insubordination in some of my earliest jobs. So I learned at a very young age that maybe I should try something about being an entrepreneur. And so I started Ciceron when I was 26. And, you know, I’ve got, I’ve got a son, who’s 26 right now. So what’s spective?

John Corcoran 4:01

Can you point to something specific with your father that you either observed in him or an example that he provided a story or something like that? How did you learn leadership from your father?

Andrew Eklund 4:13

You know, that’s such a great question. And, you know, I still get a chance to spend a lot of time with my dad, my dad has Parkinson’s and, you know, while he’s a slower person, now, his mind is just as sharp and we’ve been able to really ask him a lot of those questions, even then, in the last couple of years, because we have our memories. But it’s amazing to ask him stories like that now, they just come forth. And I’ll just tell you that I’ve had a really amazing opportunity to hear many independent people throughout my entire career. Talk to me about the impact that my dad had on them. 

And it was always that he was extremely kind and empathetic and he was a great listener, and he always just would open up his time. I am for anybody. And he didn’t have any interest in the trappings of being a CEO or anything like that I lived a very humble life growing up in a humble house, when I remember when my dad got a free company car, and he got a Honda Accord, and my brother and I were pissed, like, come on and go get a fancy car, so we can go drive it around when we’re in high school, right. And he had None None of the trappings of any of that. And so humility, kindness, empathy, these are all things that I just have always tried to be inspired by and have tried to take with me in my career as a great lesson.

John Corcoran 5:36

So how did you end up starting an agency in 1995? And to put things in context, I think I got my first email address in 1994. And, you know, when I first logged on to the web around 1994, it was before even Netscape Navigator it was, you know, dialog. Hey, well, yeah, I don’t even know. I mean, I remember in my college dorm bouncing around in a text base system. I remember going on Yahoo before going on the internet, Netscape Navigator and having to tab from different search terms, like education and stuff like that. And somehow I remember navigating around it like it was organized by country or something. And then I got to Australia, and then I got to the weather, and I got the weather in Australia. And so for me, that realization was like, Oh, my gosh, this is going to be incredible. You know, that one thing, even though it was totally rudimentary and slow. But so you must have seen some potential here. 

Andrew Eklund 6:41

Yeah, You know, I was really lucky that in my one job, I wasn’t called insubordinate. It was a great job. And it gave me an opportunity in the early 90s, like 92 to 95 to be in the bay area a lot. And I was involved in an industry that was very, very Apple based. So I would go to the Macworld conferences and Seybold and these publishing conferences. It was in the business of print. And so the magazines and the news and journalism and all that was built into it. 

And there was a technology layer to that. And I was sort of embedded in that technology layer. And so I got to spend a lot of time out in the San Francisco area in the early 90s. And so I was also becoming, we didn’t know what that was back then. But I was becoming an online community manager. No, I started an online forum in 1993. on AOL. Wow. It was like two days or two minutes, or AOL was really cool. And we were there for that.

John Corcoran 7:42

Right. Yeah. A little bit longer than that. Right, right. Exactly. Eight or something like that. Yeah. Right.

Andrew Eklund 7:48

And so we, you know, I became a community, I started this forum. And then we became a community, an international community of people that would exchange information. And we’d have chats, we’d have documents sharing, you know, you could upload.

John Corcoran 8:01

Who isn’t related to publishing, what was it around was all related to our.

Andrew Eklund 8:06

Industry, you know, and it was in the digital pre press industry. So I’ll fast forward to 1994, I was at a party, a launch party that Adobe threw for Photoshop three points out. And, and it was, it was at the Embarcadero. It’s a really cool party. And they were showing the new features of Photoshop 3.0. And there was this one, or I don’t remember what menu you would drag up to, but it was the controls or something. And it was, there was a drag down to something and said color separation. So color separation is the pre press industry. So I watched before my eyes, that industry got evaporated by a piece of technology that just appeared out of nowhere as an option for a user, for our customers to just do our work by dragging down a draft.

John Corcoran 8:58

Of the work of the company that you are working for. So you saw the writing on the wall, you felt like the company you were working for at the time was going to lose its business. 

Andrew Eklund 9:06

So that was the first time I ever experienced that. Okay, actually, it’s the second time but we won’t, we won’t go into that. I saw it also happened with desktop publishing. And I saw it again at this moment. And then I saw the web. And all this came together in 95. And I decided I wanted to start an agency. This is what I wanted to do. And I was very, deeply intrigued by the efficiency of all of it, that you didn’t have to be able to get between communicator and the listener or the reader. There was now a direct line, there were no more costs associated to do that. Now anybody could communicate with anybody else, and publish and become a publisher essentially. That was deeply empowering to me. And I just felt I had already been in Mark calm and then I was in technology. So this was just the next thing I needed to do. And so that’s when we started the agents In 1995.

John Corcoran 10:02

Who was the vision of who you would serve? What types of clients and what types of clients? Did you end up getting in the very early buddy that had money? As most companies do.

Andrew Eklund 10:11

I mean, and quite honest, because you were just starting up. The fact of the matter is, what was I selling? I was selling first generation websites. I was convincing companies, they needed to have this thing called a website. 

John Corcoran 10:23

Which not everyone was convinced in the beginning, right. So a lot of education you had to do. Yeah. Why do we need a website?

Andrew Eklund 10:32

 I’ve got a fax. Cicerone was like four people for four years. Right. That’s how much demand there was for the work that we did. Not a lot. That’s and it’s like, right now, like, there’s, there’s like a little bit of demand for AI. But there’s not like, I’m not like hockey sticking right now with AI. Yes, too much. It’s too much bombarding us all these days. And so I bring that up about like, dragging down the menu watching an entire industry evaporate. Because when we think about AI, right now, we think about where things are headed. I’m just waiting for Google or the Trade Desk, or Meta or anybody else, just to add a button any one of these days to any one of our dashboards that says, media plan.