How to Build the Best Agency Culture by Attacking Ideas, Not People

By Jason Swenk on September 12, 2021

Chris Leone was playing drums in Japan trying to figure out his next step in life when a keynote by Gary Vaynerchuk inspired him to enter the agency world. He ended up working an entry-level position in a small agency and worked his way up to being president and CEO of WebStrategies Inc, a multi-million dollar agency that focuses on mid-low funnel, lead generation, SEO, PPC, social advertising, and inbound marketing. Chris sat down with Jason to discuss how he worked his way up from the bottom of the totem pole. He also shares his experience with an agency acquisition just as he was named CEO and how he built a culture of learning. Chris’s team is encouraged to speak up and take ownership of their ideas, which goes a long way.

3 Golden Nuggets

  1. The power in saying someone’s name. Our guest is not afraid of a challenge. His first day as CEO came right after an acquisition and he was asked to handle the first meeting between both teams. This is an important moment, as the first impression on a new team is critical and may determine whether or not the acquisition is a success. He decided to spend time before the meeting making sure that his team knew everyone by name before they arrived. That way, they would feel welcome and less hesitant to give the new company a chance.
  2. Attack ideas, not people. Chris has worked hard to create a work environment where employees feel safe to speak their minds and be themselves. “It’s not a performative culture” he says “It’s a learning culture”. He builds on the belief that leaders who are open to test an idea, observe and then implement from there greatly outperform the ones who are much more rigid in their thinking.
  3. Adapting to the online office. The past two years have brought many changes and, right now, many are still not ready to go back to the office. Regarding his agency’s decision to go virtual, Chris says he continues to learn and adjust to the situation. But does not consider this will be a permanent change, nor one that will work for everyone. In his case, it made sense to go virtual if his team did not feel comfortable going to the office yet. For the future, he does not dismiss the idea of going back to an office.

Gusto: Today’s episode is sponsored by Gusto, an all-in-one people platform for payroll, benefits, HR where you can unify your data. Gusto automatically applies your payroll taxes and directly deposits your team’s paychecks, freeing you up to work on your business. Head over to to enjoy an exclusive offer for podcast listeners.


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Rise to the Top of the Totem Pole By Building a Learning Culture for Your Team

Jason: [00:00:00] What’s up, agency owners? Jason Swenk here and I have another amazing show where we’re going to talk with an agency CEO and also owner who started out at the ground level couple of years ago as an entry-level employee. Worked all the way up to a CEO. And we’re going to talk about what they did. How did they become a multi-million dollar agency? Lots of amazing things.

And also talking about how they went virtual in the past year. So it’s packed, it’s packed and let’s go ahead and get into it.

Hey, Chris. Welcome to the show.

Chris: [00:00:38] Hey, Jason. Thanks for having me.

Jason: [00:00:40] Yeah, I’m excited to have you on. So tell us who you are and what you do?

Chris: [00:00:44] Yeah. So my name is Chris Leoni. I’m CEO of WebStrategies. We are a digital marketing agency based out of Richmond, Virginia. We focus on kind of mid-low funnel, lead generation stuff, SEO, PPC, social advertising, inbound marketing, that sort of thing.

I got about, 30 employees that are located, uh, both in central Virginia and, uh, increasingly scattered throughout the world as we start to shift towards more of a full remote model over here at WebStrategies.

Jason: [00:01:15] Awesome. So let’s kind of back up to where, when you started with the agency. You know, as probably the low guy on the totem pole, it sounded like, and walk us through how you went from that to CEO. Cause it’s fascinating.

Chris: [00:01:29] Yeah, it’s been quite a, quite a long journey. So that was, we’re going back 13 years here, so 2008. I was actually a year out of school. I was playing drums in Japan in a marching band, as kind of crazy as that sounds, trying to figure out what I wanted to do next. And I stumbled across a keynote that Gary Vaynerchuk was giving.

This is 2008. This is like Wine Library days for anybody who follows Gary V. And I was like, yeah, that’s what I want to do.

Jason: [00:01:55] I remember that. I remember going to see stuff that he did.

Chris: [00:01:58] Yeah, I was at, I was at web 2.0 in, in like late 08 when he kind of made his big break onto the scene. But I found him on when that was like the place to go to find interesting things on the internet.

And I immediately clicked. I’m like internet marketing is place I want to be. And so I started kind of figuring out what I was going to do and I was interviewing, uh, I set up interviews at like Ogilvy in New York city and a couple other agencies up there. I thought I wanted to be up in New York, do all that kind of thing.

But then one of my former neighbors living down the street from me in Central Virginia, come to find out that he started internet marketing company. And so I reached out to him with the plan of talking to him and just as a learning experience and maybe even use it as like practice to go and interview at the big places.

But after talking to him, he was like, hey, I want to offer you a job. And he explained it and I’m like this actually sounds really interesting. So I kind of abandoned my original vision of going to New York City and I stayed in Central Virginia, which is not what I had planned to do.

And I was like bottom guy on the totem pole. I was really only full-time marketing person at the agency. We were primarily web development back then. And we kind of realized that the recurring revenue model was a really nice one and we wanted to get more into the lead generation side of the equation. So I was the first one coming on, doing that, making like, you know, nothing a year, but it gave me some ownership over the position and what we were doing. And I really had a passion for this kind of work.

So as we shifted more towards, uh, digital marketing and, and, you know, retainers with clients, I was always kind of the person there at the top. And the team kind of came out from under, uh, built out from underneath me, I should say. Went up, uh, director of digital marketing and then CMO, COO, president. And eventually CEO with a, with an acquisition kind of sandwiched in there as well.

Jason: [00:03:49] That’s fascinating. Let’s kind of skip ahead to the acquisition, right? Because you were telling me when, when the acquisition happened that’s when the owner was like, all right, you’re now the CEO of both entities. So we’ll just do that.

Chris: [00:04:04] Yeah. And, uh, the founder and CEO at the time, he’s been a mentor to me and he’s never been afraid to throw me into the fire.

And I’m the kind of person who thrives in that kind of situation. He very much did that on my first day as kind of being president CEO and it was the day that our two teams met for the first time. So our existing team, and then the team of this company that we had acquired. And as anybody who’s been through an acquisition before knows, that first impression that you make on the new team is so critical, right?

Cause they’re coming. I mean, put yourself in their shoes. You know, a lot of these acquisitions don’t work out for several different reasons, right? And one of which is the team, the new team comes in, they look around and they’re like, yeah, I don’t like this. I’m out. This is, I was maybe already on the fence or I was considering going somewhere else.

And they just kind of need that exposure to a new culture, new people to be like, yeah, it’s time for a change. So, yeah, those teams coming together in the same room for our quarterly retreat, which is like a full two day immersion thing. Which is already kind of tough enough to manage, especially for an introvert, like me was exceptionally difficult with the teams coming together.

But I just kind of kept my mind on the most critical thing at the time, which was, I need to make sure everybody believes that this is the right place to be going forward.

Jason: [00:05:23] And so how did you do that? Right? Because I feel that agency owners need to do that on a consistent basis, honestly, right? If you think about it, like, and I’m glad that you had that vision going in, of going, like, this is the main goal, right?

This is all that matters. So what were some of the things that you did in order to make sure you kept the right people in the right, you know, on the bus, really?

Chris: [00:05:44] Yeah. Yeah. And we were just talking about this before we went live, as well as you know. In an agency, hopefully, you have processes, hopefully you have these things in place so that you’re not dependent on any single individual for any of the services that you sell.

But nevertheless, I mean, you still need people to do all this work and good people are hard to find. So it’s not like we have machines running and we can swap people in and out and the machines keep running. Like you need people to do this stuff that they’re critical, right? So to answer your question directly, you know, the first thing that I did was actually kind of a small thing, which is we literally spent like 20 minutes of putting faces up on the screen and having everybody memorize the name of everybody in the company coming in.

Because I wanted every person in my company to be referring to people on a first-name basis immediately. And there’s so much power in just saying somebody’s first name. So, that was like something I thought of at the last minute. Is like, everybody’s got to know everyone’s name here.

And so when they walked in the door immediately shaking hands saying names. And then all of our retreats since are very much built on this. But especially in that particular retreat. It’s not necessarily a company strategy stuff or whatever. It’s, I want to spend a lot of time. Building trust, having vulnerability with each other.

There’s so many studies out there that say that teams that are willing to be vulnerable with each other are closer and tend to perform better. And so there was a lot of awareness building, a lot of trust-building in those first meetings so that people could immediately see, hey, this is not a performance culture where we’re stepping on each other’s throats.

This is a learning culture. This is a place that’s psychologically safe to express your thoughts and opinions. And we attack ideas. We don’t attack people. And we just really exemplified that in the first two days. So people could see, this is a place where I could be myself. I can be open and I can be honest, and I’m not going to be penalized for that.

So I think that set the tone right away and maybe created a sense of relief for some people who are looking for something a little bit different. And, you know, we’ve just been building on it since then.

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I like what you said. We attack ideas, not people. And I like that, you know, the vulnerable. When I’m interviewing agency owners for the mastermind, one of the biggest things that I’m looking for is are they vulnerable? And are they transparent. If they can’t be transparent with me? Like, I don’t want someone coming in thinking they know everything, right?

And same thing with employees. I want someone to say, look, I want to learn every day, I want to help people, right? I want to be surrounded by amazing people that inspire me. And especially if all of us have a similar belief, right? Like when I was hiring people, you know, in the agency, I’d be like, here’s where the ship is going and here’s why we’re doing it.

And then people believed in that and so they would stick around. And then especially if they could show their vulnerability to the team… I see this with the mastermind members, as soon as they’re like to, man, man, I just want to quit. Things are down. I really don’t know what to do.

And then they’re able to get help, then other people can open up and they’ll be like, yeah, you know, I actually have that too. Then they can work together on it. And it’s almost kind of like, I’ve never been in, in war. I’ve never been in the military, but I love watching those things. Like, you’ll see the comradely of people when they’re in intense situations. And the bond that they create.

And I even remember that too, when we’re working on really extreme projects, like with tight deadlines when we’re in the office, like we still remember that stuff.

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Chris: [00:10:23] Right. Well, and, and I wonder too, what the last 14 months have done for teams that really had a buckle down together.

When everybody was feeling the pressure of their job. There was an existential threat outside. There was the kids being at home. And there was, we were all kind of going through something pretty heavy together. And I sense that that has created stronger bonds within our teams. I would imagine it’s happened in several other places.

But just to just go back on that 1.1 more time, I had, so I just finished reading this great book “Think Again” by Adam Grant and I really liked how he framed this, which is there’s like two ways of having a discussion. One is you have somebody who immediately becomes a preacher, a prosecutor, or somebody who’s politicking for a certain idea. So preaching, prosecuting or politicking, right? That’s really trying to impose your idea and your mindset onto somebody else versus more scientific thinking.

And the studies that he cites in that book show that leaders who think more as scientists. Here’s a theory. Here’s our hypothesis. Let’s test it. Let’s observe and then implement from there, way outperform people who are much more rigid in their thing, right? So going back to attacking the idea, not the person when we attack the person, obviously that starts to become pretty personal.

We’re really clinging the ego. We’re clinging to our set beliefs on something. But when we’re looking at the idea and we separate ourselves from that, now we can just say, hey, let’s test this. Let’s run it. Let’s look back what happened. And as long as nobody feels like I’m going to be looked down upon, because my idea didn’t pan out.

If they don’t feel that way, then everybody’s continuing to contribute to the next stage in the process. But if somebody feels like they’re going down with that ship, that’s going to do a lot psychologically to them, morale, everything like that. And you see that in performance cultures especially because everybody is looking for an opportunity to stump on somebody else.

And as soon as that campaign didn’t work and that idea didn’t work, they stump on them. That’s a really toxic culture. And so we really, we want to avoid that and be more in a learning culture where we look at ideas where we test ideas, where we give people ownership over ideas. That’s another thing that our team really likes.

And we see this in the surveys that we run. When somebody comes to me and they say, hey, Chris, I have this idea for this new thing, or there’s this new service, or we want to test this thing. I say, go for it. Let’s test it. And look at what happens. They get a sense of ownership over that. And they’re not afraid if the idea is not going to work out.

They like it. Having that sense of ownership and then be able to see if it actually contributes to something in the long run. So yeah, the book is Think Again by Adam Grant and it talks about how we eliminate biases in our own thinking and the openness and the scientific method that could be applied to basically anything.

And ultimately how that affects long-term performance.

Jason: [00:13:17] Yeah. Well, and too, when you attack the idea, not the person you’re taking out emotion out of it. And that really just screws us all up as human beings, if you think about it. Like I tried my damnedest to not make a decision based on emotion, but it’s easier said than done.

Chris: [00:13:37] Oh, sure. Yeah.

Jason: [00:13:38] I probably fail at that 99% of the time.

Chris: [00:13:42] But, hey. At least that 0.1% is maybe the awareness that you shouldn’t, right?  One of the other books that I’ve been really into lately, cause I’m, don’t always read business books is so Eckhart Tolle has a great book, A New Earth that was pretty hot in the last maybe 10 years or so.

He talks a lot about identification with form and he explores it from a lot of different angles. But we have too much personal identity attached to our ideas and our opinions on things. And we’ve seen that no more than in the last 12 months with everything going on, right? So any attack on the idea automatically becomes a personal attack, right?

And that’s going to bring us all down and it’s going to make us a lot more combative and it’s going to make us a lot more miserable. So we have to find a way to separate ourselves from our opinions and our ideas. Um, and I think we’re going to be a lot happier if we do.

Jason: [00:14:30] Yeah. Let’s switch a little bit of focus and let’s talk about how you guys have gone remote. And how do you keep your team inspired? I won’t say motivate because I always tell people if you have to motivate your team, you have the wrong team. Like you should be worrying about de-motivating them. So like, how do you keep people in this going in the same direction?

Because you had a physical office, you’ve gone virtual, and lots of people are doing that. So, you know, how are you going to kind of replace some of that in office culture, going to lunch that kind of?

Chris: [00:15:06] Yeah, this is the question of 2021 right now. And we’re seeing a lot of opinions on it, but they’re just opinions.

And, you know, to be honest, if this was a podcast where we were advocating, or you guys were like advocating fully remote. I would be bringing up the ideas of why you might want to consider an office. So I’m not overly committed to any setup here. I’m committed to kind of learning from what we have in the last 12 months and figure out where do we go from here and what’s the best thing to do for our team.

Jason: [00:15:35] Yeah. Well, what was the decision that made you guys go virtual?

Chris: [00:15:39] Okay, so some of it was just timing. We had an office and the lease was expiring in end of April, 2021. And I closed our office in March of 2020. So people were not coming in. And then at some point in the summer, I said, if you want to go and you can just communicate so we don’t have too many people in there at once.

But people really were not going into it. So I was thinking, all right, why rea… I didn’t want to stay in that space anyway, so I knew that we were going to let it go. But why sign onto something in March of 2021 when people still can’t go into the office or still don’t want to go into the office.

So part of it was timing to say, hey, let’s let it go. Let’s reinvest what we’re saving from that into the team with benefits and people and the like, and I could talk about that if you’d like. Then wait to see what happens and how does the team adapt to being fully remote. And by the way, this is something that they overwhelmingly said they wanted to do.

And two, you know, what happens to the commercial real estate market? Because I think anyone can piece together it’s, you know, rent is going to become a lot more affordable. So if we feel the need to go back, that’s something that we’re going to have to learn over several months. Then let’s kind of take advantage of the market situation at that time and get something that could be even better for us than I could find right now that would be a lot more expensive.

So that was the original impetus to going fully remote, at least at this point in time.

Jason: [00:17:07] And so how has it been going? Like, is there anything that you would change?

Chris: [00:17:12] I mean, there’s certainly going to be things that I change based off of what we learn as we go, right?

At this point, I can’t say that there’s like, oh, I wish I could have that back. I mean, we gave away our office furniture. Like we raffled it off just out of a hat, gave it to people, you know, we gave them a thousand dollar home office allowance, which at this point, like is the equivalent of like three years of rent.

So it’s to anybody saying this is like a cost-saving move, it ain’t. Trust me. It’s not. So, no, I wouldn’t take anything back. It’s just kind of learn and adjust and get better. The next decision you have to make.

Jason: [00:17:50] Very cool. Awesome. Well, this has been amazing, Chris. Is there anything I didn’t ask you that you think would benefit the audience?

Chris: [00:17:58] You know, the one thing I say, Jason, at this point is we all have to be in learning mode right now. Because I’m sure there’s a lot of people out there looking at how all 2020 went and how 2021 has gone so far and probably believe this is what’s best and this is what we should do from here. But all the remote work that we experienced in 2020 and into 2021 was not happening in a normal setup for anyone, right?

There was a lot of pressures, external pressures and lack of social interaction that we had just with our friends and family. So I don’t know that we can look at everything proceeding, everything, opening back up and say, hey, we were better that way. Or we were not better that way. We just have to be in learning mode and accept that the rest of 2021 and going into 2022 is going to be maybe the real test of how well remote work can really perform for your team.

There’s no right answer for everybody here. Talk to your team, communicate, observe, do all the things a good leader has to do to make sure that the people are coming first. But you’re also taking care of the company so that you can continue to employ your people.

And then, you know, make the right decisions from there forward.

Jason: [00:19:08] Yeah. I love it. And what’s the website. People can go and check out the agency?

Chris: [00:19:13] Yeah. Yeah. We’re WebStrategies Inc, I N C,

Jason: [00:19:18] Awesome. Well, thanks so much, Chris, for coming on the show and make sure you guys all go check out their agency website. And if you guys enjoyed this episode, and you want to be around people that are transparent, sharing, growing open to new ideas, having a lot of fun. I want to invite all of you to go to and see if you qualify for this exclusive mastermind.

And if you do, we’ll actually have a conversation. And, uh, talk a little bit more and make sure you’re the right fit for it. But, uh, it’s an amazing group of individuals that run agencies and, uh, we’d love to invite all of you to go check it out, go to

And until next time have a Swenk day.

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