Company: Online Optimism
Owners: Flynn Zaiger
Year Started: 2012
Employees: 26 – 50
Welcome to “An Agency Story,” where tales of trials, triumphs, and the raw realities of marketing agency ownership unfold. Hosted by Russel Dubree, a seasoned agency veteran, this podcast series is a treasure trove of insights and inspirations for anyone intrigued by the entrepreneurial spirit within the marketing world. The episode titled “Elevation” stands out as it showcases Flynn Zaiger, the ambitious founder of Online Optimism. Flynn’s journey encapsulates the boldness and innovative thinking required to carve a niche in the competitive digital marketing landscape.
In “Elevation,” Flynn delves into the heart of what it means to lead a creative digital agency, sharing invaluable lessons on nurturing a great team, mastering networking, and the art of adaptability in a hybrid work environment. His candid reflections on the surprises and setbacks of entrepreneurship, paired with humorous anecdotes about office life and dog-friendly policies, offer both entertainment and enlightenment.
Flynn’s dialogue brims with standout moments, including his philosophy that entrepreneurs might just be “a little crazy,” and his practical advice on leveraging personal connections and genuine helpfulness for sustainable business growth. His story is punctuated with powerful quotes, such as his advice to his younger self about the daunting yet rewarding path of entrepreneurship.
This episode not only illuminates Flynn’s professional path but also leaves listeners pondering the ongoing themes of balance, innovation, and the human side of business. As “An Agency Story” continues to explore the intricate dance of passion and pragmatism in the agency world, “Elevation” serves as a compelling chapter that will resonate deeply with current and aspiring marketers.
Tune in to “Elevation” for a dose of inspiration, laughter, and a candid look at the life behind the scenes of a digital marketing agency. Whether you’re a seasoned professional or a curious newcomer, this episode promises to enrich your understanding of what it takes to thrive in this dynamic industry.
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Show Transcript
0:02 Welcome to An Agency Story podcast where we share real stories of marketing agency owners from around the world. From the excitement of starting up the first big sale, passion, doubt, fear, freedom, and the emotional rollercoaster of growth, hear it all on An Agency Story podcast. An Agency Story podcast is hosted by Russel Dubree, successful agency owner with an eight figure exit turned business coach. Enjoy the next agency story. Welcome to An Agency Story podcast. I’m your host Russel. In this episode we have Flynn Zaiger the owner of Online Optimism, a digital marketing and design agency based out of Washington, DC. Flynn believes that one has to be just a little bit crazy to start their own business. Over the years, he has taken the challenge head on by focusing on building a great team and culture. This episode tells the story of Flynn’s entrepreneurial journey, highlighting the significance of careful consideration, the power of networking referrals, the value of a great team and the challenges of transparency and the need to adapt in a hybrid work environment. Enjoy the story.
Russel: 1:18 Welcome to the show today, everyone. I have Flynn Zaiger with Online Optimism here today. Thank you so much for being here today, Flynn.
Flynn: 1:25 Thanks for having me, Russel. Excited to talk with you.
Russel: 1:26 Well get us started with a quick overview. What does Online Optimism do and who do you do it for?
Flynn: 1:31 We’re a leading creative digital agency. We have about 16 people offices in Washington DC and New Orleans. We help businesses, small, medium sized with everything they do online. Website design, social media, SEO content, whatever new website comes out in the next six months, we’re going to help businesses advertise themselves on it a little bit better.
Russel: 1:49 You sound like you may have said that a time or two. You have that down.
Flynn: 1:52 Perfect. That was actually probably 28 seconds. You can check it, but I’m pretty sure I have that down.
Russel: 1:56 Nice. Practiced. Appreciate that. Let’s go back in time for a little bit. Do you think the younger version of yourself would be surprised at where you’re at today? Or do you think entrepreneurship was always on the horizon?
Flynn: 2:06 I think they would be surprised. I always get asked, what would you tell your younger self? The thing I’d say is, you should probably think about this at some point. Don’t just dive in. My parents are entrepreneurs. They run their own business, which I think is why I thought this was possible. I should have remembered the stress it caused them, maybe that would have been helpful at the beginning. But I think that’s one of the things about entrepreneurs is if you sit down and logically look at starting your own business, it’s an absurd concept. There’s so many better ways to make so much more money, and you’ll be much happier. But if you ignore all that, I think it’s a exciting and fun journey. I wouldn’t trade it for anything else 11 years in, but I think I’d be shocked at what you have to do if you had told 22 year old Flynn what running a business was like.
Russel: 2:50 I don’t want to read between the lines, but it sounds like maybe what you’re saying is entrepreneurs are a little crazy?
Flynn: 2:55 A little crazy. Just a tad.
Russel: 2:57 Often too, when we talk about what would we say to our younger selves, one of the common answers too is I don’t think my younger self would listen anyway, so it doesn’t matter what I’d say. Or we have to think in that whole teenager mentality. If I want them to do one thing, I have to tell them the opposite or we have to use a lot of reverse psychology in this household.
Flynn: 3:12 Teenage me would definitely have been fired by adult me at this point.
Russel: 3:16 All right. That’s what I would say is you could just take this podcast back to the younger version of yourself and that’s how we’ll get to the spot we want to get. Very fascinating. Similar to my own journey, it seemed like you didn’t have a very long career before you started your agency. What drove you into being an entrepreneur actually so quickly?
Flynn: 3:31 I didn’t love my job. It’s a pretty good way to motivate yourself to get a new job. I got work essentially doing online sales for a safety video company, which is a brilliant idea. But I was a one person team and I craved working with other people on marketing. I say now in a hybrid work environment where I’m the only person in the office but I was looking for that. After six months, I had essentially tripled the company’s online sales that I’d worked for, and basically, I don’t want to say blackmailed them, but I was like, hey, tripled your sales in six months and I’m quitting. You could either try to replace me or hire me as a consultant to do what I was doing. That was the trick to early success is making sure you have one or two clients under your belt, because you’re going to spend the first six months to a year making a lot of mistakes and it’s good to have that revenue coming in as you learn from your mistakes.
Russel: 4:20 Did they in fact hire you?
Flynn: 4:21 They stayed on for probably about a year and a half. I survived. They had a little bit of turnover, I survived three or four stakeholders. The fourth one finally just, they didn’t quite have the relationship or the connection. Sometimes you get a new stakeholder and they clean house. We even see that now 11 years in, that was when I lost it but I wish them all well.
Russel: 4:37 Even in my business partner, he was at an agency and he basically was one of the first clients when we started the agency was his former employer. I’ve talked to a number of agencies now where that was one of their first jumping off points of their client was working for contract or consulting for their previous role or employer. Very fascinating concept when you sit down and think about it. Speaking of getting clients, how did you get your clients in the early days and how does that differ from where you’re at today?
Flynn: 5:01 It’s a crazy idea, but our first couple of years, pretty much all of our leads came from meeting people in person, I say as a guy who runs a digital marketing agency. To this day, we still do a lot of that. It’s the best way to build on trust. There was, exactly what you said, where you talk to friends, family, previous jobs, and you try to work for pennies. To be frank, even in the early days, if we had a job that was small, we would ask for a referral and a testimonial instead of payment, because we knew that small amount of trust is going to be what we need to sell bigger clients. A hundred dollars could actually get me pretty far in new Orleans when I started, my rent was 375 a month, so I didn’t need much to cover rent. I still would rather have the testimonial or word of mouth. That was real nice at the start. As we grew up and got older and the website matured, we get most of our leads now through SEO inbound marketing. But we still do in person events, it’s one of the reasons we still have 4, 000 square feet in New Orleans. My team down there hosted an event last night. We brought in 40 people from all around town just to talk about marketing. Not salesy, and that’s always been my biggest recommendation if you’re looking to get leads is genuinely try to help people. Big believer in karma. You’re not going to get anything by going and networking and trying to sell. You’re going to get a lot more relationships and trust from going out and trying to help people solve their problems. If it just so happens to need your services to be paid in order to solve the problems, great. But the number one goal, we always tell our staff before they go to networking, is see how you could help someone today.
Russel: 6:30 I honestly couldn’t agree more. I’d almost ask you to repeat that. I’m a big believer in, even in the clients I work with of, focus more on being valuable, giving value and then not worrying so much about how you’re going to always turn that into dollars because that will work itself out in the end. Great lesson to folks out there, thank you for sharing that. Again, similar paths or similar passions. One of the things I enjoyed about our conversation was how important your team is to you. Did you start out with that mindset or did that evolve over time? What did that look like?
Flynn: 6:57 It’s evolved over time. I don’t want to say that it’s evolved because I didn’t care about my staff at the beginning. I think it’s more that I was bad at it. I think it’s incredibly hard to manage people. It’s probably why I started an internet marketing agency is I was good with computers. This is another thing that I would have told 22 year old Flynn is, if you’re trying to grow this business, you won’t get to talk to computers. You just manage people. It wasn’t a skillset at the beginning. We’ve made some lucky hires that were very talented that wanted to join a nimble team and I always have told people like, look, this is an opportunity. We will listen to you. We’ll give you a lot of power and opportunity. We try not to have bureaucracy, which I’m sure every bureaucrat says when they’re running a company cause it’s yeah, I’m CEO, everything I want happens quickly with no one stopping me. It’s been great. I think the real key has been that I’ve learned to trust my team a lot because they make good decisions. A lot of decisions without me and they push back on me a lot, which is super beneficial. One of the things I’ve learned as CEO is you have to reward people for pushing back because it’s gutsy to talk back to the person who covers your paycheck. We learn that from talking to clients all the time. They’re paying you to tell them when their idea is bad, but it’s still hard to tell someone that signs your checks, hey, that’s not a good idea. I have a better one. I’ve learned that sometimes you need to take a deep breath and go, you know what? I think you actually are right. That’s been incredibly valuable. There’s been a lot of times in our decade of work that I could pinpoint a time that I was wrong and a employee was right, and that’s why we’ve been able to grow to where we are today.
Russel: 8:25 I even love the clarification you made to the question of, not that you didn’t care, it’s just the lessons you had to learn to maximize it. I think that is often in, even in my own case, when I talk to other agencies, it’s not a lack of caring sometimes when mistakes are made in that arena, but that it’s all the pressures of starting a business. How do we keep the lights on? Sometimes leads you down some wrong paths, but a good clarification to the question there.
Flynn: 8:46 Yeah, I was going to ask, cause I know you’ve managed a team for a lot longer. I think one of the things we see is that you run into the same people again and, I’m sure you have that where it’s just such a small industry that you’ve got to be nice because you’re gonna talk to them in a couple years.
Russel: 8:59 I think that’s what we learned, service based business, all our costs, our whole product is our team. Too often the business’s focus is getting customers, but if that’s our whole product and service, you have to put just as much attention, effort, and care in the same way we think about customers, right? You don’t want a bad review, they tell someone, that whole thing, totally exists on the team. I think that’s a good insight you have. Tell me what the Online Optimism secret is to having a great team.
Flynn: 9:21 It’s listening, which I think is good relationship advice. I try not to bring too much relationship advice into a business, but I genuinely think that listening and enacting on what you’re hearing is super useful. Our biggest pieces of feedback is that we ask for too much feedback which is fair and we had to work on making sure that people feel that if they give us feedback that they’re hearing it and that we’re hearing it and that we’re taking action or at least letting them know we hear this and this is why we’re not taking action. It’s crucial that you’re asking for feedback pretty much as often as you could take action on it, whether that’s like quarterly reviews or surveys or just end of year check ins or NPS surveys, net promoter scores, you can’t take action unless you are getting that feedback. Especially if it’s negative. It’s so terrible to hear negative feedback, but you have to realize that they’re going to feel that way, whether they told it to you or not. It’s better to hear it so that you can fix it, because not asking doesn’t mean that they’re not going to feel that. That’s always my biggest advice is listen as much as you can.
Russel: 10:22 Gosh, Flynn, I feel like we need two hours for this podcast cause you’ve got so many great nuggets that you can share on that front. Listening, it makes me think of this story, we had a client, we didn’t end up working with them but they basically had this huge national organization around they were trying to branch out to other things, but it was basically relationship counseling, and so we had to go. I was supposed to take my wife to go test this out at one of their seminars thing. My wife couldn’t go, so I had to take a co worker and we found the whole thing laughable, a little interesting. Certain parts were like, we’re not doing this part. But it was just funny, the whole basis of, if you just take the net nutshell of that whole conversation, it was about listening as the secret to any relationship. You’re corroborated by evidence there. On the flip side, what are some of the mistakes or do you have any mistakes that you’ve made that you can share so people don’t go down the same path?
Flynn: 11:05 I don’t want to necessarily call this a mistake, but this is something we’re trying, which has been fascinating, we’ve been trying lately, offering job offers to people with transparent salaries. What we mean by that is on our job page, it says how much you’re getting compensated, you get the full benefits package. We don’t want to try to negotiate with people. We think that’s more fair for these specific positions. Then, getting to the end of a very long interview process and being wildly different understandings of what the compensation is. The reason it’s maybe it’s a mistake is that it hasn’t worked out because we’ve gotten to the end and what’s been fascinating is we have a paid internship program and I always taught our interns negotiate, negotiate, doesn’t matter if it’s your first job out of college, you should try and negotiate. Now I’m running into them and they’re negotiating against what I thought was their offer. I think that’s been fascinating to see and I think there’s a lot more conversations, particularly as generation Alphas all move into the workforce and there’s increased requests for transparency, but there’s also people who don’t want to know that. I think it’s something that everyone should try. It hasn’t worked out perfectly for us, I’ll be the 1st. That’s why when you talk about a mistake, that’s the 1st thing that came to mind. But it’s worth thinking about, at least if you’ve never seriously considered it, what that would mean for the job, what that would mean for everyone on your team who would see a compensation if no one else is aware of what everyone else makes. These are conversations that CEOs and business owners have to be aware are happening because even if you’re not posting that compensation, more and more businesses do, especially since it’s now the law in New York, and I believe Colorado and possibly California soon. There’s going to be more transparent salary compensation information in the future, whether you’re doing it or not, so it’s something you need to be thinking about.
Russel: 12:37 The advent of tools and salary.com, Glassdoor and things like that. It’s crowdsourcing the information on the backside, whether or not the company’s being forthcoming with it. Trying to be more transparent, but people were always interested in, it’s almost that ego driven where I’m different. I know there’s this thing here of transparency and standards, but I’m different. Show me how I’m different. It was one of the things we ended up having to figure out how to solve is same uniqueness, or I don’t know what the term is.
Flynn: 13:01 If you can get rid of people and egos you’d have a perfect business, but you’d be a one person shop with no clients.
Russel: 13:06 Ain’t that the truth. Solve the world’s problem with that, I guess you could say. That I don’t see happening anytime soon. One of the things you mentioned already in the podcast today is the struggle with balancing a hybrid environment. Where do you currently stand? What has and hasn’t worked for you down this path?
Flynn: 13:20 We consider ourselves completely hybrid. What that means is if we have physical offices, we allow people to work entirely remote, we will offer co working spaces. Essentially, if you’re in New Orleans or DC, we have physical offices that you could come in, sit in. We have unlimited snacks, drinks, free lunch on Fridays that we bring in from catering. We can do events in either space. If you are in one of those cities, you live a couple blocks away, you also can never come into the office, which is, people think, oh, you offer a hybrid for people, not in those cities. No, I have staff who live a mile away from the office who maybe show up once or twice a year. We’re fine with that. If that’s what helps them work good. If you’re in a different city than where we have offices, you could work entirely remote. We’re happy to pay for a coworking space, and that gives people the most freedom. That’s most helpful for recruitment. The downside obviously is that it is very costly is the, I think the technical term for it, paying for two physical offices. We also pay for any co working spaces. We also have to make sure our staff has the appropriate equipment to work from home. It is wildly expensive to do all that at the moment we’re doing it. There’s benefits to allowing us to recruit from anyone who wants to work, whatever work style there is. I stay more sane when I have a physical office to come into. There’s not any cats climbing on my head during this podcast, which is maybe a downside. Polly would have been working from home today. I think it’s been helpful in recruitment. Everything is great about that sort of philosophy. It is incredibly costly. As a business owner, you have to decide what is the price on that? I’ve decided it’s good enough at the moment, but we’re going to see how that changes over the upcoming years.
Russel: 14:45 I look forward to seeing how that experiment shakes out. I think one of the things in talking with other agencies that are similar is what maybe initially seemed as when you could drop the office or whatever, it’s oh, that’s a whole cost savings I get to not have. But what I think we’ve seen as this evolves, even if you have a remote work environment, you just have to transfer a lot of that budget into other things, right? Whether it be co working spaces in other locations or helping people set up the right environment set up or… or when some people do it to just make sure, hey, we put out enough budget to bring everybody together every now and then. That’s not a lost line item, it’s just where you apply it. What is your goal with the business long term? And what do you see your big challenge to overcome to get there?
Flynn: 15:19 One of the things that we think about at Online Optimism is our mission and vision, and, this is a good example of listening to our staff. When I first came up with a mission vision it was back probably our third or fourth year. I was told the company needs one. I came in one day and told them I wrote our mission and vision. I was like, this is it. Then I thought that was going to be an announcement and it turned into a discussion, cause I was told that I don’t know our mission and vision. We had those meetings for weekly for a year before we all agreed on it. Five years went by and our staff changed and all of a sudden everyone was like, we don’t agree with the mission and vision. And I was like, can’t do this again. But it’s been interesting. Our vision is to be a leading creative digital agency that creates exceptional work and fosters employee growth. It goes on a little more, but I’ve always thought that’s been key. It goes back to one of your first questions, which is why did I start this? Is that I didn’t love the job I had and I wanted a place I’d be happier. You spend so much time at work that why shouldn’t you be happy? Your life shouldn’t be work. Work is one of our values. This is just all a job. If we weren’t paying our staff, they wouldn’t be here. I don’t think they would talk to me, and that’s fine. This is a job, but that doesn’t mean that it can’t be a great job. You can’t have a great place for people to work. I think if your people are happy, and they’re motivated, that will lead to better performance. That’s not just me thinking, there’s obviously been studies that happy, motivated employees do better work. That’s my long term goal is genuinely be a business that has the best employees because we can hire the best people and we have the best culture. I think if we do that, everything else from revenue to profits, compensation, all of that will work itself out as long as you’re keeping your staff happy. That’s what I’m trying to do every day.
Russel: 16:46 Where do I apply? Last big question for you, Flynn, and someone that maybe… I don’t know, I’m not going to assume the answer here. Are entrepreneurs born or are they made?
Flynn: 16:55 I feel that they’re made. I think you can certainly be born like I was where you have family. I was lucky enough to see people do that and that certainly gives me a head start. it didn’t give me a business. I wasn’t handed this, I had to build. I built it from learning from them and learning from my peers and learning from everyone I met going to all those events early in my twenties, we didn’t just get new clients from networking. I got a ton of lessons and mentors. I feel that they are made from those around them.
Russel: 17:23 Did you get a lot of help from mom and dad in the early days, as far as advice or things like that, or did you intentionally not go to them for advice?
Flynn: 17:30 We run very different businesses. As a present a couple of years in, they told me to stop helping them and doing work for their business so I could focus on my own, which was very considerate. They certainly helped me a lot with motivation. They’ve always been supportive. They’ve run a store since 1980, so I can only hope to be around for at least 40 years like they have.
Russel: 17:48 That is a long time, for sure. Indeed. If people want to know more about Online Optimism, where can they go?
Flynn: 17:53 You go to onlineoptimism.com, you’ll find us. You could also search on any of our social media channels. I don’t manage those anymore, so feel free to tweet at us, it’ll go to someone else and it’ll go back to me. That’s how I learned what we’re doing on social media. You can also, of course, contact me Flynn@onlineoptimism. com, F L Y N N. Whether you’re looking for a job, or marketing, or advice, or just want to talk about weird career advice you’d give 22 year olds, happy to chat with anyone.
Russel: 18:17 Sounds like a whole podcast niche. You can create weird job advice for a 22 year old. Great to hear your story today, Flynn, so many great nuggets, especially as it relates to team. Thank you so much for sharing all that I appreciate you being on the show.
Flynn: 18:28 Thank you, Russel, been great talking.
18:33 We hope you’ve enjoyed this episode of An Agency Story podcast where we share real stories of marketing agency owners from around the world. Are you interested in being a guest on the show? Send an email to podcast@performancefaction.com. An Agency Story is brought to you by Performance Faction. Performance Faction offers services to help agency owners grow their business to 5 million dollars and more in revenue. To learn more, visit performancefaction.com.
Flynn: 19:09 Our rug budget at Online Optimism is one of our more significant office expenses. We have a dog friendly office in New Orleans, you gotta learn to create policies. We said dog friendly, and then a week later we were like, dog friendly and friendly to humans was our policy. And then within two weeks, we were like, dog friendly to humans, must be potty trained. I think a good lesson, you should always think through the consequences of some of your policies, but we have some great marketing staff and we just buy new rugs every six months nowadays.
Russel: 19:35 I assume most of the potty trained is geared towards the dogs, not the human, but you just never know. To your point, be clear.
Flynn: 19:40 We should add that to our HR policies. That’s a good, we don’t have that. I wouldn’t be able to reprimand anyone. That’s a great point.
