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May 11, 2026
02 Conor Lewis - Money, Meaning, & Making It Work
02 Conor Lewis - Money, Meaning, & Making It Work
00:00
21:10
Transcript
0:00
[gentle music] All right. Today you're gonna hear from Connor Lewis. I met Connor as I was the head of marketing, and I hired him to do a couple of jobs.
0:10
Um, he was exceptional to work with and, uh, somebody that does a really good job, uh, being authentic, I think, on LinkedIn.
0:17
So I reached out to Connor and wanted to have him be one of the first, uh, conversations that I had as a results. I hope you enjoy the talk that we had. I'm getting married in June. Are you? I know. Excited.
0:26
Dude, congratulations. Thank you very much. Now three and a half years in to building an agency, I'm pretty confident and, and proud to say, like, "Yeah, I run a business. It's called Studio Lewis.
0:40
We make ads for software companies." It's a well-oiled machine at this point, so. It took me a while to get to that pride, but, um- Mm-hmm... now I have a lot of pride behind it, so- Yeah... I feel confident.
0:49
One of the things I'm curious about is have you hit a point, you're, uh, it's three and a half years in, have you hit a point where you almost kind of yanked, yanked the cord on it and went back and looked for a full-time job?
0:59
Yeah, there was like, year one, I think I made like a total of $40,000 or something. It was, uh, ver- it was quite small. And I live in Boston. I live in the center of Boston, very metropolitan, very expensive.
1:12
And there were times where I thought I wasn't gonna make rent. Um, I pulled $10,000 out of my, like, brokerage to help me, you know, pay for stuff. I wasn't depositing any money.
1:23
I wasn't saving any money in year one, and I was like, "This is the worst. I think, um, I'm probably just gonna go back."
1:30
I was also getting bombarded with Instagram ads from self-help kind of coaches who somehow knew exactly what my business was.
1:38
Like, they'd be, "Are you a video business owner making under $10,000 a month and hate your life?" [laughs] And I was like, "Uh, well, shit, yeah. I guess I'll listen to this ad."
1:46
[laughs] And I, I even got sold on a $9,000 coaching package that didn't help me at all. So, uh, I was kind of down bad. I, I got burnt by, like- Oh, man...
1:55
I got burnt by, like, this coaching business that didn't really help. I- Okay... was not making rent. There were, like, many nights where I was just crying in bed. I looked at creative director positions.
2:06
I applied to a bunch of them, got a lot of rejects because my, like, previous role in the house was video lead, um, which is not quite the same as creative director.
2:14
And so I was just like, "Shit, well, you know, there's some roles at Zoom Info for, like, a video producer. It pays 70K a mo- or a year. Maybe I'll, I'll go try that out." And so I did apply to some.
2:27
Um, I heard back, but I decided to abandon those processes after a firm talking to by my fiancée. Love her to death. Yes. [laughs] And, um, also like you're, uh... I feel like it's a marathon, um, in retrospect.
2:42
Like, as soon as I thought I'd hit or I was in my low points, like, deals came out of the woodwork. My network kind of vouched for me.
2:49
Um, people were curious about if I was willing to do this or that, and I got bigger opportunities almost without too much work on my end. Um,
2:58
and so, like, I ended up sticking it out, and I'm really happy that I did, but, uh, yeah, there were some low lows. There were times where I was like, "What am I doing with my life? I feel like a directionless creative."
3:10
Like, I almost felt selfish 'cause I had a, I had a fiancée at that point. I had, like, future plans, and I was risking those- Mm-hmm... to bet on myself, which was really hard.
3:20
What have you learned about how you value your work, and how do you, like, how do you personally do that trade-off of here's what I...
3:28
here's the stuff I wanna work on that's meaningful, but, like, I also have these material needs that I need to meet?
3:34
That's something honestly that I think I made a conscious decision to give up only taking work that I was, like, really excited about, if I'm being honest. Mm-hmm.
3:44
Um, in like year two, um, there were kind of two paths, right? At, on year two, um, we were at a point where I was... In year one I, I made scrap money.
3:54
On year two I made like $100,000 in, in that year, and so we were doing okay. That was profit, by the way, so I think we hit like 400K in revenue. Mm. And it was, it was cooking.
4:04
And then there's, uh, but I was at capacity. I was stretched as thin as humanly possible, and, um, I was also wearing a sales hat, a marketing hat, a delivery hat, as I'm sure all first-time founders are.
4:16
Um, and there was, like, two paths in the road. The first one was, like, the path of the artist, where I could charge more and more for my work and be pickier with the projects that I choose.
4:27
Um, and that was really appealing to me because I, um, I kinda had this, like, desire in the back of my mind to help nonprofits, to help, um, I don't know, to work in, like, consumer packaged goods.
4:39
Like, imagine making an ads for shoes. Oh my God, a Nike ad one day. Like...
4:43
And then the other route was, um, the entrepreneurial route, which is make a repeatable business that I could teach to others, get back some of my time, service and niche really well, and have, like, really good subject matter expertise in that.
4:56
And while that wasn't, like, as exciting in one aspect, which is, like, the creative aspect, it was exciting in, like, a personal development, kind of can I, can I delegate?
5:07
Can I challenge myself to build a team, a process, a point of view? Uh, I eventually chose the path of the entrepreneur, um, and I don't regret it.
5:14
It's actually very gratifying to have a strong point of view in software, ads specifically, and also to raise a team. I think one of my, like, biggest weaknesses as a human being is that I don't delegate trust very well.
5:28
I try to do it all myself, and that has caused me to self-destruct more times than I can admit. Hmm.
5:34
And so part of the personal journey has been to actually delegate, to learn how to teach these, like, production processes that I know so intimately, but have never written down.
5:44
Now I'm at the point where we have a producer on board who's taking care of clients way better than I could.
5:50
Um, we have, like, a whole process for every one of the videos that we make in such a way that all the videos are still super creative in their own w- way, but they still work because we know they follow the process, and that's its own kind of gratifying.
6:03
And there's, like, its own creativity in, that gets unlocked because I've bought a little bit of my time back.
6:07
I can start to make really things that I'm passionate about for LinkedIn.Um, which is my channel of choice, and I can work on the content that I really care about, which is connecting with other creatives, teaching people how to make good videos.
6:20
Um, that's the stuff that lights me up, so. I love it. So are you actually doing, are you s- are you selling your own content to, uh, to other creators? I just recently started doing partnerships, which is new for me.
6:32
Okay. Um, but for the most part now, I'm just making content for myself. You're just doing it for... Yeah, you're just doing it for content. Okay. Yeah. I basically have, like, three things that I kind of...
6:42
Like, three content pillars. The first one is, like, ad breakdowns. Mm-hmm. Where I take an ad and break down the script and say what works. Which are so good. Yeah. I love those. Those are fun. Yeah.
6:49
Um, the hardest part is finding an ad I really like [laughs] in B2B. The second is, um, behind-the-scenes videos.
6:56
So I've actually started to hire a separate videographer, um, for each of our sets, and, like, talking about how we accomplished, like, doing a lot in one day or tackling a really tough creative.
7:07
Um, those are really fun because I never got to watch those growing up. Like, I would always gawk at Hollywood sets and be like, "I don't know." It's like a black box. Mm-hmm.
7:15
But I'm trying to open up that black box and show people, like, what goes on on set. Mm-hmm.
7:19
And then the third thing is, um, just, like, me being my goofy self in front of the camera trying to teach about some kind of video concept. Those are fun because I feel like I get to let loose. I get to be myself.
7:30
I think the heart... That was a journey, by the way, and I'm happy to talk about it. But- Mm-hmm... I finally feel like myself in front of camera. Yeah.
7:36
Which means that people who connect with me and end up being clients usually like who I am and don't try to change me, which is nice. Um, so it has all those benefits. But- Right...
7:46
the fourth thing that I've added on recently is partnerships. Okay. Um, I've said that I'll only partner with products that I, I would actually use in my current day-to-day or in a past life's day-to-day,
7:56
and so far that's only been two companies of, like, the six or seven that have reached out. Okay. That's cool. Kudos. Thank you.
8:04
So one, one of the things that I appreciated when we were, did those projects together is, like, you're su- like, you are super meticulous. You have v- like, you're able to stick to timelines.
8:14
Like, I'm just impressed by how you had a process in place and how you ran it.
8:19
I'm curious, like, what are, what are things that you've learned that, like, are keeping you, keeping you sane and, like, on the track that you wanna stay on instead of falling into chaos?
8:29
Which is where I personally feel like I [laughs] w- I am. Um, but like- My God... what, what, what does that look like for you? Yeah. Staying, creating a process is the, the first way to protect your sanity.
8:40
Um, but I'm not good at it, I'll be honest. I've found someone who is good at it, and that's my fiancée. She joined the business last year in July, which was a very big decision for us.
8:48
I actually ended up splitting the company 50/50 with her. I mean, we're gonna be married anyway, so whatever.
8:54
Uh, but it was also, like, scary because I, I don't know, this person's becoming my everything, and then they're becoming that plus my work everything. That was very frightening.
9:04
I was worried that I wasn't gonna be good to work with. Um, just a lot of things. So, uh, that happened. She joined the business.
9:13
She immediately saw that it was a disaster that I was duct-taping together in the background- [laughs]... which, uh, is true. I'm not the most organized person. I just pretend to be.
9:21
And then, um, she created these SOPs that were brilliant. What we did, and what I would recommend to anyone who personally struggles with creating process, um, was we literally went to a cabin [laughs].
9:34
Uh, in this case it could just be an off-site if it's [laughs] not your fiancée. But we went to a cabin in the woods, and I narrated my process for 16 hours straight into an AI transcription, uh, very meticulously.
9:44
Like, she would ask me, "Okay, if we have a customer story, like, how do you hire the crew? What exactly do you tell them? What does the brief contain? Where did you find them? Like, what website did you go to?
9:53
Um, if we don't have any contacts in that v- city, how do you hi-" It, it was so minute, and at the end of it I felt so drained, but, um, the, we got all of it on a transcript. We turned it into SOPs with Claude.
10:06
Um, we proofread them over the next few weeks to make sure that they were really good and that we were linking to, like, looms when it was necessary.
10:13
Uh, that whole process took about a month, and it was, um, something that I just should've done at the start of my business. Um, because, uh, it's been so easy to onboard people. It has saved so much time.
10:22
It's given clients a better experience. Um, highly, highly, highly recommend delegating SOPs to, um, to AI and making sure that you are very meticulous with your descriptions and your transcripts. Mm-hmm. Um, but yeah.
10:38
As far as, like, I just also have, like, 10, 15 years in this, so as far as, like, knowing what to do and what processes to do, I've just failed so many times that, like, I know how not to fail.
10:48
[laughs] It's, it's just a matter of repetition. Yeah. It's just a numbers game. [laughs] Exactly. Good point. Um, okay. So, like, you, you, you mentioned AI. I'm, I'm curious what you're...
11:03
I think everybody has their own weird relationship with it right now, as they're trying to figure out, like, how to use it.
11:07
Things are coming too fast to be able to, like, adequately, um, educate and respond it feels like. Like, what is your, what is your personal approach to AI, and, like, how are you keeping yourself sane with
11:20
all of the changes that come with it? I fluctuate between feeling like AI is this existential threat and AI is the savior of all the work that I don't wanna do, uh, like, daily.
11:32
[laughs] And so especially in video, right?
11:35
I'm a video creator, and so every Twitter bro is gonna tell you that, like, my job is going to be extinct in two years because AI has the capability to make amazing videos, and they've been saying that since 2021.
11:48
And so I'm still here. We're growing year over year. Um, and so more and more I'm starting to be in the camp of, like, AI is there for us to alleviate, um, a lot of the stuff that you don't like doing.
12:03
And more and more I've kind of tre- treated it like a coworker, where I will get off of a sales call, for instance, and immediately start talking to Claude about how I want the follow-up email to be shaped.
12:13
Shoot it out in a minute, shoot it out to the, the salespersonI'm of the opinion that, uh, AI disclaimers are really nice.
12:21
So like if I make a piece of content with using AI, I'll just put a disclaimer in there about how I used AI.
12:28
A lot of the things that we're testing internally is like, um, screenplays are the, the bible of every project that we do. Um, everyone looks at the screenplay. The actors use it to learn their lines.
12:39
The props designers use it to build out props and characters and sets. The editors use it for pacing. Um, the client uses it to understand like the story that we're telling.
12:48
Uh, it's just like it's the most important document, and it's really hard to write because there's a lot of details that you might miss.
12:55
So what we've been testing out is having a writer basically create an outline and then turn that outline themselves without AI into like a really short script with just like character lines, uh, you know, the creative dialogue bits.
13:09
And then we have a screenplay skill that we've set up that asks that writer a bunch of questions about like what are people wearing, uh, what kind of expression does this person have as they say this line, um, just like pokes holes in the script and a- asks a bunch of questions that the screenplay would need and turns that like really sparse Google Doc into this really detailed screenplay, um, complete with like software animation notes and all this stuff that everyone would use.
13:36
And so that's been the biggest like aha moment in the past few months where I'm like, "Holy shit, like this used to be such a headache. Um, it used to take like hours to format, and now it's taking minutes.
13:48
Where else can we do this?"
13:50
Where I'm not a fan is where people think that it can just go straight from input to output, like give me a video of a, a horse riding another horse or something and expecting it to look really realistic and ready for screen.
14:00
Don't think it's there yet, but we are using those kinds of videos for internal storyboarding. So like when we're showing- Mm...
14:06
clients frame by frame like how we think the story will progress, we'll use AI video that looks bad [laughs] but it gets the point across of like who's the character, what's the shot type, you know, what's the flow.
14:18
Um, so I think AI's there to help us. I just think we need to like stop using it to replace our own creativity and start using it as, um, almost a conduit for like this, this...
14:30
ourselves and, and getting stuff down on paper, especially if you're a dreamer like me. Yeah. I think my biggest trap as a, as a person is like I overcommit myself.
14:42
Um, and I am an anxious person at heart, so I get really stressed out and, um, my attitude changes in a very negative way.
14:51
And so I think where I've been getting stuck over the past three and a half years of owning a business is just like there's never a time where I haven't... Th- th- there's never...
15:02
It's not like you're in-house, and you just like completed the project, and you get like a break, you know, where you're like, "Oh, work's slow right now. This is nice."
15:10
When you're on your own and when you're an entrepreneur, it's never like that. You, you... There's always something that you could be doing.
15:16
Uh, and so my brain just fires all the time at night like, "Oh, I gotta make this content. Oh my God, I gotta get back, get back to this client." And my like eternal weakness is never being able to turn off.
15:27
Um, I'm just not good at it, and I'm still working on it. Um, that's part of the reason I'm in therapy is to work on that.
15:35
And so like, uh, that's my biggest trap, and that's something that I, I aspire to eventually put boundaries up and be like, "Okay, I need to take a break." Um, where I've found a lot of success is, um,
15:50
trusting other people more to do... to help me out. Um, I think, I think there's this overwhelming feeling when you're an entrepreneur that you're alone, um, that you don't have a team to rely on, that you,
16:03
yeah, that like no one understands your journey like you do, and that's like, that's toxic self-talk where you can trap yourself and make yourself feel alone by saying that.
16:15
Uh, and more recently I've been sharing my frustrations with business more openly, um, at events, at parties, at hangouts with friends, at honest conversations with my fiance at the dinner table, and the amount of help that I've been offered, not even asked for, is astounding.
16:33
And you're not alone, and it's very nice to feel that way, so. Well, what kind of stuff are you working on that you're excited about? You wanna do any show and tell? Hell yeah. Promote anything? Take it away.
16:42
Oh, what can I show, though? What can I show? [laughs] Um... You probably have secret projects that are too si- like too soon and... I do. I do. I really, really... I've...
16:52
We, we did this work with ClickUp lately that I'm like so proud of. We shot seven entirely unique concepts in two days. Um- Nice... but I can't share it because they're not released yet.
17:03
Um, I'll share this other one which I've been talking about a little bit. This is not the final color, but at least you'll get to see what I'm talking about, which is, um...
17:11
I'll play it on mute really quick while I explain what's going on. We did this like p- '90s PSA style brand video where we highlighted Bailey Zappe, um- [laughs]...
17:21
which who's like a quarterback for the Patriots and I think now is in the New York Jets, question mark? New York something. Okay. Uh, and it was my first time ever working with like a QB,
17:32
like someone professional who's like, uh, a big deal, and paid, like Zapier themselves paid a lot of money for him to be there. Um, and then it was also my first time working with an entire cast of kids.
17:44
Um, kids can be super unpredictable, especially as actors, and so I was very nervous. Um, this was my first time working with like a big brand like Zapier, at least a big brand in this space, and I thought I was...
17:54
I thought everything was just gonna go to shit. It was like six kids- [laughs]... a quarterback.
17:58
The quarterback came with their own agent, and she w- he was only allowed to be there for exactly six hours, and we normally have a 10-hour set. And so I was like, "Oh my God, this is gonna be a mess."
18:06
Uh, it turned out wonderful. We're doing more projects together because of how wonderful it was. The kids- Yeah... were amazing. Jace, who you're seeing on screen now, is a natural-born actor.
18:15
I swear to God he's gonna be famous in 10 years. He looks like it, yeah. He's just got a attitude. [laughs] Um, his character was hard, too. He had to like-...
18:22
basically shit talk the, the QB and, and like roast him for his football stats- Wow... while, uh, he was a know-it-all, uh, in this classroom where he's teaching about Zapier. So it was so funny.
18:34
Um, all the parents were on set for all these kids too, and so they were giggling in the background as their kids, like, delivered these very sarcastic lines. Um, it was just so fun.
18:44
So that's the- I, I have so much more that I could share, but this is the one that I think I look back on and I'm like, "Oh my God, if I could ever do a project like this again, I'd be really excited."
18:52
Oh, that's awesome. Cool, man. Well, this has been really fun. Yeah. So- Thanks for, thanks for doing this... you, you are, you are conversation number two out of what I'm hoping will be 100. [laughs] Oh, good. Good.
19:02
So I set the bar pretty high, but, um- 100, holy shit... for, for some reason like- I mean, if anything, this is also like a networking, like- Yeah... way to, way to n- put yourself out there and meet people. Mm-hmm. Um,
19:15
yeah. Yeah. Probably- I've got a whole...
19:17
I, I, I'll actually send it to you 'cause I would truly value your opinion, but I actually put together a page where, like, I want to put it out there so that people can just, like, once I grow the, the subscriber list a little bit, just put it out there and, like, anybody can sign up to do a session like this.
19:31
So I've got a page out there for it where you can, like, schedule it, and then pick a time slot and then, you know, get a prep email. So, like, I wanna automate it.
19:38
Um, but I'm starting with a lot of people I've been working with and, um- Oh, cool. Are you, um, turning it into a business of some kind, or is it more just like a media lever? No, it's just gonna be like...
19:49
This is what I'm... I'm just gonna do it as my newsletter. It's gonna kinda be like the anchor project of my newsletter. I started writing. I've been having a lot of fun writing, so I did...
19:58
I've done one essay a week for the past four weeks. But I wanna start doing, um, I wanna start doing- Wait... video series. How do I subscribe to your newsletter? It's honestxd.com. There you go.
20:11
I'm still kind of figuring out how to make it, like, how to present it so it makes sense. I keep changing my mind, like, every 48 hours on stuff. [laughs] Welcome to early stage- Yeah, exactly... content creator.
20:24
Um- But, um- Unsolicited advice, I might recommend- Please, yeah... doing this on Riverside. Um, you've probably used Riverside before. I think it's even free. Yeah. Or they have a good free plan. They have a free one.
20:35
Um, and you're totally right, it's one of the things I'm looking into. Cool. Um, so yeah, good word. I still, I still appreciate you recommending Wistia, 'cause I've been using that on multiple- Oh, yeah...
20:44
projects for things. Um- Wistia's so good. Um, they're one of the two companies that I partner with actually. Oh, that's awesome. I've used... I've loved their product ever since I was in-house. I was like, "Oh my God."
20:53
Nice. And I don't know if you've ever watched their marketing, but it is a breath of fresh air, to be honest. I don't think I have, actually, um- Yeah... for whatever reason. But yeah, man. So- Thanks for having me.
21:03
This was a pleasure. Uh, yeah. [outro music]
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