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Chris Vendilli is the Founder of Vendilli Digital Group, a Pittsburgh-based creative marketing agency that helps local businesses and organizations reach more customers online. He has a diverse background, starting in the US Air Force before transitioning to a career in law enforcement as a Pittsburgh police officer. While pursuing higher education, he discovered his passion for technology and began dabbling in online business, leading to significant success in digital marketing. Leveraging his entrepreneurial spirit, Chris shifted to his agency, providing web design, development, and online marketing services, with particular expertise as a HubSpot Platinum Partner.

tune in

Here’s a glimpse of what you’ll learn:

  • [3:12] Chris Vendilli talks about Vendilli Digital Group’s comprehensive digital marketing and branding services
  • [4:20] Chris’s unique professional transition from the Air Force to policing to owning a successful marketing agency
  • [10:20] How a knack for technology led Chris from a beat cop to a computer crime investigator
  • [15:22] The reasons for the strategic move to purchase a new office space amid the pandemic
  • [18:23] Insights into the acquisition process of buying other agencies to fuel growth
  • [25:21] The financial and strategic aspects of negotiating an agency acquisition
  • [32:55] Vendilli Digital Group’s customer success stories

In this episode…

Have you ever considered how a career in public service could translate into successful entrepreneurship? What can you learn from someone who has maneuvered his way through various public service careers before settling as an agency owner?

Experienced b2b sales and marketing technologist Chris Vendilli delves into how, as a US Air Force veteran and Pittsburgh police officer, he transitioned into an innovative agency owner, applying his diverse skill set to conquer the digital marketing space. With strategic acquisitions and a daring physical expansion of his business during the pandemic, Chris outlines how Vendilli Digital Group has evolved and established itself in the competitive marketing industry.

In this episode of Inspired Insider Podcast, Dr. Jeremy Weisz interviews Chris Vendilli, Founder of Vendilli Digital Group, about his evolution from the military to digital marketing supremacy. Chris delves into his agency operations, the acquisition process, and client success stories. He also demonstrates the power of tactical career pivots and the importance of building a strong team and culture to adapt and thrive in the rapidly evolving digital landscape.

Resources mentioned in this episode:

Special Mention(s):

Related episode(s):

Quotable moments:

  • “Learn the power of ‘no’ and say ‘no’ to the wrong customers.”
  • “I realized that I was looking ahead a bit, but with my military time, I could retire at 43… I thought, what if this was my full-time gig?”
  • “Buying those agencies, just like buying this building, I feel like is a great way of growing.”
  • “We made their digital reality more congruent with their actual reality.”
  • “What an agency is really worth is what someone’s willing to pay.”

Action Steps:

  1. Embrace your diverse experiences: Leverage skills from past roles to inform your current endeavors. This broadens perspective and can inspire unique approaches to business challenges.
  2. Prioritize culture and collaboration even in times of distancing: A shared space can reinforce team identity. A cohesive team environment promotes creativity and productivity.
  3. Be tactical in acquisitions: Consider how proposed terms align with your future control and goals. Critical evaluation of terms ensures alignment with long-term business objectives.
  4. Utilize owner financing as a strategic option for agency purchases: Can bridge valuation expectations and facilitate smoother transitions.
  5. Never be afraid to invest in your business to enhance services and stay current: Investment in technology and training ensures that a business remains competitive and relevant.

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Episode Transcript

Intro 0:01 

You are listening to Inspired Insider with your host, Dr Jeremy Weisz.

Jeremy Weisz 0:22 

Dr Jeremy Weisz here, founder of, where I talk with inspirational entrepreneurs and leaders today, is no different. I have Chris Vendilli of Chris, before I formally introduce you, I will always like to point out other episodes people should check out a couple other good ones. Jason swank actually had him on twice. Chris and I both know Jason. He talked about how he built up his agency to eight figures, sold it, and then the second episode of how he’s been buying up agencies and just different things in the business space, the valuation space, and he also has a group where he helps agency owners. That was a really — both of those are good episodes.

I had Ian Garlic on the show who runs and he talked about the importance of customer success stories. We’ll talk about some today with Chris. He talked about how just some innovative, interesting marketing ideas. His dad owned a restaurant, and they had live dolphins in the restaurant. Now that’s kind of weird and interesting, but was even stranger, it was the restaurant was in Wisconsin. Okay, so live dolphins in Wisconsin in a restaurant, but we talked about standing out, standing out from the crowd. So that was a really good one, too. That and many more. You can check out, and this episode’s brought to you by Rise25. At Rise25 we help businesses give to and connect to their dream relationships.

And how do we do that? We actually do that by helping you run your podcast. We’re an easy button for a company to launch and run a podcast. We do the strategy, the accountability and the full execution, Chris, we call ourselves kind of the magic elves that run around in the background and make it look easy for the host and the company so they can develop amazing relationships, create great content, and, most importantly, run their business. For me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships, and I’ve found no better way, over the past decade, to profile the people and companies I most admire and share with the world what they’re working on.

So if you’ve thought about podcasting, you definitely should, if you have questions, go to That’s all we do. I am excited to introduce Chris Vendilli. He went from the Air Force to the Pittsburgh police to owning an agency. The agency does web design, development, online marketing, advertising, and a lot of HubSpot training and consulting. And Chris, thanks for joining me.

Chris Vendilli 2:56 

Thanks for having me. Yeah, I know we talked about though, on an interview for a while now, and appreciate the invitation.

Jeremy Weisz 3:02 

Well, you were busy actually buying a building and moving in, which we will talk about, but just start off with Vendilli Digital Group and what you do.

Chris Vendilli 3:12 

Sure we’re a digital marketing agency, we do I know mostly some of your listeners, or a lot of your listeners are savvy, so we do some design development, or HubSpot, Platinum Partner, branding, positioning, inbound marketing, digital advertising. So you got our site up there. Another cool thing that we do is a little more off the beaten path. We’re certified to bring Google Street View inside of a business somewhat unique, but most of our clients are a little more b2b focused, either professional services manufacturers with several SaaS clients, or they have kind of a higher transaction value or lifetime value customer.

So in those scenarios, we might have, like a wealth management firm or trying to think like, basically, we’re looking for customers with, like, a high lifetime value customer, because in that case, the way we’re set built to run and what we do, the math just makes more sense. The economics work out a little bit better for sort of full service agency retainer with PPC and SEO experts and designers and developers all at your disposal.

Jeremy Weisz 4:20 

How did you stumble? We’ll go back. I want to hear if you’re allowed to share any crazy detective police stories at some point. But how’d you stumble into the agency world?

Chris Vendilli 4:20 

So like when I bridge that gap, I’ve always been kind of a technophile, sort of a gadget freak, computer guy, and I went to college right out of high school at Pitt, and I played hockey there. Suffered a little shoulder injury in a practice and my grades quickly went down the tubes when I wasn’t practicing three or four nights a week, practices in games three or four times a week on the ice hockey team. So I joined a fraternity — great. Kind of went to the gutter. Is this a no profanity on this podcast? You could swear? Oh yeah, my grades went to shit and I found myself on double secret probation. I realized, I’m just not really ready for college.

And once I rehab the shoulder, I joined the Air Force. But the consistent thing throughout was I was always like a little bit of a nerd. I came home from the Air Force. Four years later, I was active duty, stationed overseas the entire time, and I went back to Pitt. And while I was there, I started doing the eBay trading assistant as, like, a way to make some extra dough on top of my GI Bill. And I realized pretty quickly I enjoy building the auction listings and teaching myself like HTML more than I enjoy, like dealing with other people’s junk. And then I started building websites for people. I had a couple sites. While I was still going to pit full time, there were membership sites. I was selling information products. This is taking me down memory lane, but I wrote the same paper and submitted to two different classes. One was my English class. One was an intro to programming class about how to use MySpace to market your business.

And around that time, I had bought an eBook on eBay for 99 cents, and I’m very meta, but I paid the 99 cents, and the eBook came to my email, like, minutes later, and I was like, I just paid this guy, like, midnight, and I got the eBook, like, three minutes, like, three minutes, like, instantly, and that guy’s probably sleeping, and just made a book. And I looked at his reviews, and I saw he had like, 20,000 reviews. I’m like, he’s sold a lot of eBooks. So I wrote this paper thing, like, maybe I could make it an eBook. And my one professor said there’s not a lot of stuff talking about how to use MySpace bulletins and software for MySpace to promote your business, you should consider turning this into an eBook. And I was like, I’m like, a half a step ahead of you, like, I was kind of thinking about that. And I made a little mini site. I sold the eBook on eBay, and then I actually linked up with another eBay power seller.

Did a separate membership website about how to become a power seller. But long story short, I was in school full time, and I made, like, something like $80,000-$90,000 the first year on these two websites, while I was a full time college student, and like, I got the bug. And probably around that time, I think that was maybe when bad boys came on. I thought I was going to be like Will Smith. I could go continue on that military trajectory and be like a cop with secret money from my side hustle, and I use pseudonyms on my membership sites. I was Mr. Black. Nobody knew it was Chris Vendilli. And I had, like, some really prominent internet marketers buying my stuff. And I had little upsells, you buy the eBook, or you could upgrade to the membership area and pay 20 bucks a month. And I had like, 30,000 people on my list and hundreds of customers in a private forum, and I took the police gig and I did that for more years.

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