Jul 21, 2026
Episode 02: Ari Evans, Founder and CEO of Maestro
Episode 02: Ari Evans, Founder and CEO of Maestro
00:00
59:36
Transcript
0:00
We were very out of money. We had done everything we could. We'd made tons of cuts, cut salaries down, everything that we needed to do.
0:08
The company was about to be on a much different trajectory, but we weren't on it yet. We had a mega contract that was about to be signed that was basically fulfilling the original vision of the company.
0:16
It was horribly dark for the family. We could have been dead. We were equally likely to be dead. [upbeat music] Ari, welcome to the Two Arenas podcast. Thanks for having me.
0:33
Happy to be here. When we first met in 2015, we were both at very different stages in our lives. You recently started Maestro, and I had just become a venture investor.
0:47
And over the past ten years of working together, we both became dads. And the name of this show comes from Roosevelt's Men In The Arena. You're in two arenas at once. You're building Maestro,
1:02
and you just had your second kid. You're trying to be excellent at both, and the cost of trying is what we're here to talk about. We'll start with fatherhood, we'll move into the business that you're building,
1:15
and if you're ready- I have to tell you something, which is a crazy thing. There is one quote in my LinkedIn profile, only one, and that is the one. Did you know that? I did not know that. That is the quote.
1:30
Second idea is talked about a lot is the arena of business, but I think the arena of fatherhood is one that deserves conversation as well. And as you know, it's hard to separate the two. Yeah.
1:44
So I'm very excited to get into this with you. Yeah. We have the extra wrinkle of, you know, Olivia being my wife and also the head of ops at Maestro, which intertwines work and business, [chuckles] uh- [laughs]...
1:56
more so than most people would think should ever be intertwined. [laughs] We have a three-year-old and a three-month-old, so it's probably too early for them to know exactly what Daddy does.
2:10
But say you were to hypothetically explain to them what Maestro is and who is it for, how would you do it? [laughs] Uh, my three-year-old's pretty bright.
2:23
He actually, like, gets on this chair that I'm sitting on and he tries to go to work. He's been doing that since he was, like, two. When I explain to him what I'm working on, I just think it's easier to just show him.
2:34
But to people who aren't my three-year-old, what we do is we try to make video experiences interactive and engaging. So, like, what's interactive about it?
2:43
Usually a kid doesn't understand stats, but if I say, "Hey, it says how many touchdowns there have been," like, he'll understand what that means. Or, "Hey, did you see that touchdown?
2:52
If we wanna watch it again, we tap here." Right? Or like, "Hey, do you see the jersey he's wearing, that shirt? Yeah, we can buy that if we tap here." And he g- he totally gets those things.
3:04
So to understand, like, why is that a thing that Dad makes? Or like, how does Dad do that? Or e- that's, like, lost entirely. The end experience of why someone wants to do that thing, that connects with him. Yeah.
3:17
And a three-year-old gets that. Three-year-old gets that. That's incredible. Yeah. That's incredible. I mean, he'll tell you, like, every part of how a rocket works and, like, you know, the Artemis II.
3:27
He knew, like, everything that was going on with the launch and what was happening with the moon and when they were l-landing and like... Y- yeah, he's got an engineering brain.
3:35
[laughs] Well, kinda as you do, so maybe it runs in the family. It totally does. I bought a house a few years ago, so I've become the house ve- handyman, and I do a lot of repairs.
3:45
And so we bought him his own tool bag with, like, a wrench, hammer, whatever, screwdriver. And if I go do a repair, like, he brings his tool bag over to try to, like, do the repair with me, and he's learning stuff. Like,
3:59
he just has a thirst for this stuff. It's awesome. Yeah. When they get, uh, a slightly more verbal, it's just like, "Oh man, this is my best friend." [laughs] You know? Like, she's just like me. You know?
4:13
It's, it's really cool. That's amazing. Yeah. So you started Maestro in 2015 when you were young, I think dating, and no kids. Walk me through who you were as a CEO then,
4:27
what you cared about, and how you measure what a good day was. Hmm. I've always had big ambitions, right? An aspiration to build a big business and to run a big company and to make a big impact.
4:45
Those are things that matter to me. It wasn't really about the financial return. Back then, like, a lot of change was happening.
4:50
We, like, had a different startup that Maestro came out of it, and there was a lot of excitement around where can we take this thing?
4:56
And so that was, like, a lot of the drive was just proving that we could do the entrepreneurial journey. Uh, and a good day, I mean, I'm, I've always been kind of a workaholic since I was a kid.
5:04
I'm not proud of that necessarily, and that's had to change a lot. Back then, validation was getting customers to use it,
5:13
and also creating a culture and a team that I felt proud of that could deliver at the quality level that I had in my mind. And I would kind of say that that latter piece didn't happen until recently. Like, truly, right?
5:28
Any creative person, there's a gap between, like, what they see in their mind's eye and what they create.
5:34
And the more experience they get, hopefully that gap closes so that what's in your mind is much closer to what you actually produce in the world. And I feel like this year, in the past year,
5:47
that gap has actually become very small. I can make the thing and then be like, "This is what I want. Now can you turn this into the, the, uh, production grade version of it," right? So yeah.
5:59
I think it's just been humbling how hard the journey really is. Like, you know, we talk about this all the time, that we were just way too far ahead of the market when we started.
6:07
And there's sort of nothing you can really do about that. You can, you can try to accelerate it, but then all of a sudden when the market was ready, it was like, boom, wildfire.
6:15
But I just got humbled along the way, like what it really takes and what kind of tenacity and grit you have to have if you actually wanna pull through. So adding a wife to the mix [clears throat] was, um...
6:30
I mean, well, we worked together, so that was, like, less difficult. But having a kid definitely changed the calculus a lot. Uh- So would it be fair to say that validation and getting customer
6:47
was how you measure a good day? I think the wrong things were validators. You know, how much money you've raised from VCs or some other thing like that. There was a bit too much influence of that in my mind. Hmm.
7:02
It's definitely changed now. So who are you now, a decade and two kids later? What's the same about you as a CEO, and what's become different?
7:17
I think that my ability to determine signal from noise in lots of different areas of my life has changed dramatically. What actually matters for growth?
7:28
What's a good measurement of if you're doing a good job, if the company's doing well? That changed a lot. Simple narrative, simple product, simple everything. How simple can you get it so that value pops right out?
7:40
"I bought X for this reason. I got X." Right? I learned this as an entrepreneur when I was younger, you should have, like, one metric that matters and really stick to it.
7:51
But I don't know why, when you're young and dumb, you just, like, kind of ignore some of the advice that you get.
7:58
You get a lot of advice at the same time from a lot of people, and until you're older and more experienced, it's hard to know how to weight the advice that you get. Not all advice is created equal.
8:09
So, like, not only do you not understand that when you're younger, but you don't really have enough way to say whether someone's advice in the topic they're advising you on should be something that you really take to heart.
8:23
And it's not throwing anyone under the bus. I'm sure everyone had the best intentions trying to help me, but a lot-- I got a lot of bad advice that I followed.
8:30
Right now I have a much better, like, gut sense of like, "Okay, hold on a second. What's the context around this advice? What is their motivation? What experience do they have?" Right? "What's my own experience say?"
8:45
And triangulate those things better too, determining if I should follow it or not. Hmm. When you were expecting your first, did you go out and ask people what it would be like to be a dad? It's funny.
8:58
And did you listen to their advice, or did you- Yeah... end up learning on your own?
9:02
There's this weird thing I think that I, um, did that I'm trying to erase from my personality, which is that somehow asking more people for advice feels like some kind of safety net.
9:14
As if that's somehow like an insurance policy against the outcome when it's really not. These days, I still ask for advice from certain people on certain topics. It's definitely more curated when I do that.
9:28
But otherwise, I'm more confident in myself and more trusting of myself and my experiences and my decision-making framework. And did that apply to being a dad as well? Yeah.
9:38
See, dads give you advice whether you ask for it or not. [laughs] Um, I don't think any advice can really actually prepare you for the transition from so many different perspectives.
9:48
One is like, and I'm sure you experienced this, it's just a light switch on/off thing about how your priorities change immediately. Immediately, right? You have this thing you need to keep alive.
10:02
You've been provided somewhat minimal instructions, certainly from, like, the medical side, right? [laughs] Like, almost nothing. They just hand it to you and then- They just hand it to you, right? Good luck. Good luck.
10:13
And it just kinda puts a lot of things into perspective. I think before being a dad, it was like live to work and work to live, unfortunately. Uh, and then when you have a kid, it's like work to provide for family.
10:33
Like, the rules are rewritten. You're rewired, you know? And, like, people have asked, "Well," like, "don't you miss when you were, like, single and you didn't have all this stuff?" And the answer is n-no, because,
10:46
like, I'm just rewired this way. This is clearly the most important thing in my life, is, like, providing for this thing, my family.
10:54
And your family feels, like, so different from when you're just married and have a family.
10:58
But, like, when you have a kid, that notion is very, very, very different, what you actually mean and feel when you say that word.
11:04
I think a lot of it is being able to, you know, weight the advice you're getting, including your own from your own experiences, and kind of understand, like, what the biases are- Mm-hmm...
11:14
with whoever you're getting advice from, including yourself. Yeah. So when your first was born, where was Maestro as a company? Was the company doing well or was it in a more challenged period?
11:29
I know we've been through some ups and downs together, but- Yeah, we have been... place it for us where the company was when he was born. Yeah. So this is January twenty twenty-three. Um, during that point in time,
11:44
it was a challenge period for sure. Um, it wasn't the peak challenge, but it was a point in time where we sort of knew that the path we were on wasn't the right path and it was gonna be a problem.
12:02
We needed to sort of make backup plans for what we were gonna do while we figured out the right path. And, uh- Yeah. There was a much, like, tougher time that came when he was one. Much tougher.
12:19
I mean, I didn't take much paternity leave. I think like 10 days. I think that's, uh, it's kinda tough of founders to really step out. Mm. More should if they can, and, you know... And what do you remember about
12:35
either that time of birth or that period when he was about one that you alluded to, uh, about your capacity to be a father in those moments?
12:49
So during my honeymoon and some other periods of time, I read some books on Zen Buddhism and started practicing it only on trips. Not-- I should let it bleed more into my normal day-to-day.
13:06
So during that time, I learned this important thing about Zen Buddhism, which is that happiness is the absence of craving. Really simple idea. Don't crave more, you don't crave less.
13:25
And if you spend your whole life being on the wanting, craving one direction or the other direction, you're never in any kind of stable stasis point. There are no, like, problems in the world. The problems are in here,
13:42
right? You interpret events in the world as problems, but they don't actually exist. They're not like problems by definition. That's like a construct of your mind, right? So when I'm with my kid,
14:00
I can think about all the things I wish I want, I, you know, craving, or I could force myself to just not crave. The path to it for me is don't crave. Just be comfort...
14:13
You're just this ti-- you're, you're this amount of tired today. You're this amount of whatever today, everything, right? And then if you're able to just feel that, then you can actually be present.
14:26
And I find that when I did that with my newborn, I would just be crying. Crying of happiness.
14:37
Because you could actually be there and feel the gravity of where you are in your life in this special event that is occurring, and just have that be the thing that dominates your being fully.
14:52
You can't help but be overwhelmed by that.
14:56
By this, like, gift and the clarity and focus around the gift and the gratitude for the gift comes so much more easily when you're not lost and your mind cycles aren't like thinking about changing where you are or what you are or how you feel.
15:11
Mm. That is beautifully said. Definitely hard to implement, so I hope that [chuckles] we should have a separate conversation about, you know, how I can incorporate more of that in my life.
15:26
But as a father and as a CEO, do you feel guilty? Sometimes. Um, my wife and I are really good communicators, but even us, like we still needed to like go to couples therapy.
15:41
You can't just have a kid and have everything be the same it was before, plus be a dad. [chuckles] I know that sounds so dumb to say out loud, but for example, you can't work till seven and have dinner.
15:55
Little kids have a schedule, and unless you want your life to be hell, you should kinda like helpfully stick them on a schedule, right? And so that schedule requires that you like get up from your desk at this time,
16:09
and then if there is time later, then return to it. And that was like a big shift for me. And so like determining, okay, I can do that three days a week, was like the first arrangement.
16:21
And then, like, my wife would do it other days. Okay? And then it kinda became like, well, you know, if it's like, if we're just taking turns either one handing it off, then we're not like spending time as a family,
16:38
right? 'Cause she also needs a break. So it was back to this recalibration thing. Why am I working so hard? I feel that I need to, because if I don't, then somehow we don't get to where we need to go.
16:56
Where do we need to go? Big goal is financial security. That's my objective. I want financial security so that, like, my kids can be taken care of, my wife can be taken care of, I can be taken care of.
17:11
I've got a number in mind what that means. That's like our target to get there. So, you know, what determines whether I need to work this hard to attain that, like, somewhat abstract [chuckles] objective? Nothing.
17:23
Me, right? And so where does that come from? Right? Uh, and that's maybe something that's like more in individual therapy or like if you don't achieve it, then what? I'm a failure. Why?
17:38
Why does that necessarily mean that, right? You are a failure.
17:44
As a whole person, you're a failure because, like, you didn't like exit your startup by the time you're thirty-five or thirty-eight or whatever the ar- totally arbitrary timeline I put in front of it. Well,
17:57
that's like some deep-rooted crap [chuckles] that, like, needs to be addressed. I think a lot of founders probably find themselves there. So many of us do this to ourselves. The goal post is constantly moving.
18:10
There's no time to celebrate any achievement 'cause it's like the next achievement. Right And you ascribe success to s- arbitrary results, right? Like it's misaligned with your dad goal, potentially.
18:25
Of financial security and have an amazing family, they're not actually not the same thing, [chuckles] right? Right. It is a bit more challenging when you are a founder or an executive and a father, right?
18:40
I think, like, that's part of the challenge. Things kind of like compound one against the other. So, you know, you mentioned it, the sense of guilt. How did you carry it and how did you
18:53
deal with it, or how do you deal with it if it's still around? I work from home and just make sure I take, like, breaks and, I mean, how convenient.
19:00
I can just go out and, like, play with my kid for, like, 20 or 30 minutes and, like, make him laugh and smile and then, like, go back, right? Mm. Um, and try to, like, mix those things into the day.
19:10
And then also trying to make sure, especially as he got a little older, that I was, like, making time for, like, memorable quality interactions, right?
19:18
'Cause it's easy to just be around the house, and there's certainly times that you just wanna, like, hang out and play here.
19:27
Taking my kid to the beach when he stuffed a whole handful of sand in his mouth and tried to swallow it. [laughs] Like, I'll never forget that. Yeah. [laughs] Right? [laughs] Like, he, like, remembers these things.
19:36
Like, they impacted him, and they're positive memories with me. You know, my kid was, like, super into, um, trucks and construction vehicles, so, like, where can I go that I can, like, see them working, you know? Uh,
19:54
really into rocket ships. Like, cool. Like, where is there a launch? Can I ask a friend to go to a launch? Yeah. You just gotta find the creative juice to do it. Yeah.
20:06
It does sound like you're very thoughtful and creative about it and really trying to be in the moment with them. Yeah. But what's the thing about, about fatherhood that you're still bad at? I think that,
20:20
um, like the control element. You're just like when you're three, you know, your emotions are big. You're testing things. There's this, like, pushback thing. I just feel like I lose my temper sometimes too quick.
20:36
You know, I can count on one hand the number of times I've yelled, but sometimes you're just driven to this place where you're just like, "You just need to do what I say." It's also
20:47
gets worse when I'm stressed out or sleep deprived or sick or something else where, like, my ability to, like, take a deep breath and do something about it is, like, low. I mean, snaps. You know, I mean, any human snaps.
21:01
Um, so it's just hard to be empathetic. Your kids are tripping. Like, quite literally, what happens in the brain is very similar to a psychedelic trip that someone is on.
21:18
And if you've ever been on a psychedelic trip, someone trying to, like, control you or your thoughts or any- or your actions in that state is, like, pretty futile. Our brains as we evolve,
21:30
evolutionarily, we wanted shortcuts.
21:33
Well-trodden paths are enhanced and less traveled paths are, like, dampened, and your brain does this, like, dampening thing that doesn't want, like, all things to connect to all things 'cause it's not efficient.
21:43
But kids' brains are still doing that. They're making, like, random connections for things that they're experiencing, and there isn't that, like, well-trodden path thing. All paths are being walked, right?
21:55
That's like a totally different experience of the world, that all paths are being walked all the time. So, you know, it's, like, impossible to get on that level, but you gotta keep that frame of reference in mind.
22:09
So yeah, what am I bad at? I'm, I think I'm bad at losing my temper a little bit. It doesn't happen that often, but there's been a handful of times, and he remembers them. You know? And, like, you can't undo it.
22:19
And thinking of mental states and, you know, how that impacts how you behave or how you work, I think there is a
22:27
particular kind of loneliness in being a CEO, especially when you're going through a difficult time in a company's, uh, lifetime. And in your case, your wife, Olivia, has been a part of that company from the early days.
22:41
So at those moments, was having her in with you, did that alleviate that loneliness, or did it compound- Hmm... given that your entire household, you know, financial security was essentially tied to one cap table?
22:59
Great question. Um, generally speaking, it causes a amplification of positive moments and a, like, downward spiral in negative moments.
23:13
Um, so the highs are higher, and we, like, celebrate them more, and we're happy about them, and vice versa. The, the lows are, like, really amplified negatively, and it's, like, kinda hell.
23:23
Being at the top and having everything on your shoulders, just your wife can be the best support ever, and my wife is, but you just don't know what that's like unless you are in that spot.
23:37
All the financial eggs in one basket element has been a scary thing in the family, and during some of the really darkest times, we, like, decided that we should probably do something about that.
23:49
We never had to, but we started to. You know, think about it. You have to. Um, yeah. Maestro went through some of, like, really, really, really dark times on the way to where we are now.
24:06
And, you know, for better or worse, when your wife is your best friend or your partner is your best friend, you kind of, at least I, somewhat mistakenly try to have them wear, like, every hat.
24:20
Well, she's my partner, and she's like my colleague, and she's my wife, and she's these things. Can she also be my therapist? At a certain point, like, no, right?
24:32
[laughs] Your wife can be a support, I think like a sounding board, recognize and see you in the way that you feel and try to keep you positive and like, you know, cheer you on and believe in you.
24:45
But deep down it is very lonely, and unless you're in that seat, you don't really understand what it's like, especially when your goals are like off, right? Like, why are you so upset?
25:02
Because if, because if this doesn't happen, then that won't happen. But why does that matter? So you're back into that like chain of issues, right? But that's also what makes founders so great, right? They like have that
25:16
just thirst drive. Like, you know, you can't stop that train. It's gonna like blow through the brick wall. So it's hard to kind of reconcile all these things.
25:24
It has felt at times that if I try to change something about my personality, that it would like wreck me as an entrepreneur, 'cause I don't wanna lose those aspects of myself, and that has been like really difficult to like detangle things.
25:39
Mm. Has any of your wiring evolved?
25:45
Not maybe changed, 'cause I think that's, you know, too much of a, of an ask, but have you noticed that you've evolved over the past few years as you've been, you know, both experiencing more success with the company but also experiencing more success with the family?
26:02
There's been more detangling, just in kind of realigning around what matters, and yeah, as the company has experienced more success, there's like naturally less stress. There's more like stability in the house.
26:16
My wife was able to take maternity leave for a pretty long time. As far as I go, so we just had our second kid, and I took like ten days of paternity leave when my second arrived, and, you know, I blame myself.
26:34
I feel like I can't take more time. In some ways, I think it's literally true, because I haven't really created the right structure around me that I'm like, can really fully step out that way. I blame myself for that.
26:49
There is guilt associated with that. I hope now is about to be the test of did I evolve? Can I make the change? I end my day at 5:00. Period. 5:00. Right? And that makes me feel weird sometimes.
27:01
Like, am I working a nine-to-five? Like, it's not that the job is a nine-to-five. [laughs] That's clearly not what it is. It needs to be that way for the family dynamic to stay really positive and happy. Mm.
27:19
But on the other side,
27:21
get back on the computer after my kids go down, and then I can't sleep because my mind's like going a million miles an hour with all the stuff I did until 11:00, and then that's like worsening the sleep deprivation, which is worsening my ability to make good decisions, create those good memories, be creative, all these things.
27:41
I've definitely made the day-to-day element better, but I haven't evolved as much as I want to. It sounds like Olivia has been an incredibly supportive partner- The best...
27:50
both on the business side and the personal side. The best. But at the same time, ten years of building one company is a long time to ask someone to wait for the outcome, right?
28:01
I think your kids are too young to remember the hard years, but Olivia has been there all those years with you. Yep. What has Maestro cost her specifically across those ten years, and have you asked her recently?
28:16
Look, it's really easy to look back and do this thing called resulting, which is where you look at the, uh, the quality of an outcome and mistake that for the quality of the decision.
28:30
Humans in general sometimes confuse the quality of the outcome with the quality of the decision.
28:35
The quality of the decision has a lot to do with what information did you have at the time that you made the decision, and given that state of information, did you make the right call?
28:46
To answer your question, we have had this conversation. We read this book called How to Decide, and actually going through that book,
28:56
you look at decisions you made in your life and try to decide if you're deciding well, [laughs] right? Mm. And the truth is that we made good decisions along the way given what we knew at the time.
29:10
Would I have done things differently given what I know now? Of course. But did we make the right decisions then? Yes. So what it cost her, I don't know. It's easy to look at all the things you don't have, right?
29:23
Back to the craving thing. Okay, so like what, what did it give to us? Well, how about we met through work? This relationship wouldn't exist without Maestro. Mm. Maestro afforded our life. We have this house.
29:40
We have these kids that we love. All those things aside, there w- du- during some of the darkest moments, there was this like reflection on like, okay, yeah, I've been here a long time. Maybe I'm not growing anymore.
29:52
Maybe I should go somewhere where I can grow. Fair. You've put in your time. She's done a ton of different things at the company. Um, yeah, like what, you know, what do you wanna do?
30:02
Well, I wanna like see how like big organizations do things from like an operations standpoint. Yeah. Sounds, sounds good. But I always told her like the grass is always greener.
30:16
You know, just 'cause it's a bigger organization doesn't necessarily mean anything about like the quality of the organization operation. Yeah. So what would Olivia say about you as a father
30:31
that you wouldn't say about yourself? [laughs] Uh, my wife and I work really well together because I'm the dreamer and she's the operations person. It's good and bad.
30:40
Sometimes, like, I'm like, "I don't wanna think about how I'm gonna bring this thing to life. I'm just dreaming right now." And her brain goes straight to, "Okay, this is the first step. These are the 10 things."
30:50
I'm like, "I'm not there. I'm just, like- [laughs]... imagining," right? 90% of what I imagine is throwaway. It's necessary [laughs] on the way to finding the real gem.
31:02
Then let's, uh, let's try to figure that out for that one. Um, the way that that plays out with my- with our kids is I'm the creative one. I'm the one imagining, right?
31:14
Like, I'm in the world with my son, and he's making up a story, and I'm, like, adding to the story and like, "Yeah, and this...
31:21
Yeah, and here's this emergency over here, and that's why the firetruck has to come in," and, like, being in the world with him. And you can see how much it amplifies him and how much he loves it.
31:32
And for her, that doesn't come naturally, right? Like, it takes a lot of work to, like, imagine a story that's interesting, and he asks for them, like, every night before going to sleep.
31:46
So I don't think it's, like, jealousy, right? Like, she does things in our family that I c- could- couldn't do, right? [laughs] They don't come naturally to me as much.
31:57
But I think that's one element is, like, when I'm with the kids, and the other thing I do well that she's not as good at is, like, the phone does not come out- Mm...
32:07
when I'm with my kid, unless it's like a must-do this thing, not coming out. It's very hard to turn off work, and it's very hard to put work down,
32:17
and especially when it, it's something that you've been working on for a long time, and I feel like you're finally coming to the moment of a 10-year overnight success- [laughs]... that we talked about in the past, right?
32:30
Um, but as you alluded to previously, there's been multiple almost near-death experiences throughout the company's life. You know, you struggled to raise for years, hit a round and rode the back of the COVID wave.
32:48
Then you had to retrench when that model didn't work. Can you walk us through the specific moment when you came the closest to actually ending the company? Yeah. So that was in December of 2024. We were
33:05
very out of money. Um, we had done everything we could. We'd made tons of cuts, cut salaries down, um, yeah, so everything that we needed to do.
33:20
The company was about to be on a much different trajectory, but we weren't on it yet. We had a mega contract that was about to be signed that was gonna, like, basically fulfilling the original vision of the company,
33:30
right? It was about to be signed, multi-year deal with a huge Fortune 100 company, and we had investor complications. Um, and you know, [laughs] we signed, like, all the paperwork
33:50
basically on Christmas Day, which was insane, and I remember, and I continue to catch flack for it, like, "Why was Ari working during, like, the Christmas holiday?"
34:09
We were with my in-laws. My father-in-law is an electrician, right? He- head electrician at a, at a theater in Broadway, and, like, when he leaves the office, work is done.
34:21
It's, like, quite literally impossible to do your job, right? And that's, like, such a different paradigm for my world, right? Where I'm always working, essentially. Um,
34:36
and this was a pivotal time where there was no choice, and because of the delicate situation that it was in, it required, like, a lot of phone calls.
34:48
I had to build support, almost like with voters, by calling one investor at a time. We have a lot of people on the cap table. You know, you gotta provide a lot of context. You gotta answer people's questions, right?
35:00
Like, we're talking, like, 30 minutes to an hour each phone call. Luckily, we navigated through it, um, but it was horribly dark for the family. Mm.
35:11
Just feeling like we need to give up on this thing when we're so close to the glory, um, and, like, the, the conversations and the activities were so, like, definition of threading the needle.
35:29
We could've been dead. We were equally likely to be dead. That's, that's the kind of grit that I'm made of, but for her it's like, "Well, how many times can Ari pull a rabbit out of his hat?
35:41
But how many times can you actually do that? Like, the, a rabbit's gotta be ending sometime," right? [laughs] Can't do this forever, right? [laughs] There's a never-ending clown car of rabbits- Yeah. [laughs]...
35:51
coming out of your hats. The rabbits keep coming. Yeah. But, like, deep down, I do believe that. I'm always gonna find a way. I believe that at my core. And I've seen it, so I can second that. Thank you.
36:07
But for everyone else around you, you're like a tornado, and they're like, "Don't you see this thing coming? Like, you're not gonna survive that." And I'm like, "I'm pretty sure if I just hang on right here- [laughs]...
36:17
and do these things that I'm gonna survive this, and it's gonna be great." And do you recall how you were able to navigate and get those votes over the line? Because a fraction of a percentage
36:30
Could have tipped the company in a completely different direction I just tried to keep it really factual. This contract that was already signed,
36:43
like when we started having the conversations, the, the contract wasn't signed.
36:46
But once it was signed, it's like, okay, we know for certain we're gonna be cash flow positive as of this date that is not too far away from now, right? And then profitable as of this date, not too far from now
36:58
with like 100% guarantee. The reason you invested was because of this vision. I don't think there could be bigger validation than who this customer is. Luckily, I have pretty good relationship with all my investors.
37:12
I wasn't coming to them cold.
37:15
I still can't imagine the economy that must have been going on in your brain because one side you have the contract that's gonna validate the entire existence and premise of the company that you've been working on for the past almost decade, and on the other hand, you're negotiating whether you can have enough
37:34
survival wiggle room to make it happen. Like, I can't- Yeah... imagine how that must have been like in your brain. Yeah. Mentally very, very challenging.
37:44
Uh, easily the most challenging professional experience I ever went through was that experience. There were moments along the way where for the first time in all those years, I'm like, "Should I abandon ship?"
37:55
Those, those thoughts had never come in before. You know, there was just a period of time where for the first time in my professional or entrepreneurial career where there was like some doubt.
38:06
It's always good to have, it's healthy to have doubt, but like that level of doubt was like, was I just totally wrong about the thesis? It's been enough time,
38:20
you know, and you've seen all the different like permutations and variations and ways to, "Oh, we're gonna reinvent ourselves or reposition and go after this market or go after that market."
38:29
I've tried so many things in that period of time. Maybe I'm done. Maybe there is no gold anywhere around here, you know, or that like nagging thought that like, I know there's gold, it's right around us.
38:42
We're just not digging in the right place. It's, but it's right somewhere here. [laughs] There was that time, uh, between 2023 and 2024, somewhere in there, like, like deep depression, right?
38:54
Like, honestly, like hard to, to deal with, of just I wasted my life. I wasted my time.
39:04
You know, I will never get back the chance to have been like, you know, a young founder with some like crazy escape velocity thing. Which again, like why is that the thing that it need to be? I don't...
39:14
It's just like a thing that I made up. But yeah, you know, there, there are definitely moments where it just, it, it all felt like a waste.
39:24
And here we are now, where you're quietly becoming the interactive layer for some of the biggest names in sports media and gaming, um, in the world, right?
39:36
Like you're out there in a way that I don't think a lot of people appreciate that you have this scale. So now that you've been able to replicate this and you have this scale, what does that unlock for the future
39:50
of what- Yeah... you're looking to build? You know, for years, so many investors and friends, colleagues said like, "You just need that like one deal that like changes it all."
40:01
And there were so many times along the way that I'm like, "This is the one. This is it," and it never really was. It's like what's happening to us right now is kind of like when a tier one VC leads you around.
40:12
There is some element of that that happens in the space, whether we wanna admit it or not.
40:17
The equivalent to that for us is, you know, in other cases where maybe a t- tier one broadcaster would say like, "Oh yeah, you know, let's like crawl, walk, run. Let's like, you know, do a POC and then step it up."
40:27
Now it's like, well, you know, I can just go watch Monday Night Football and I see it and it's freaking awesome, and so like we need to catch up to that.
40:36
What's happened is it just switched from being a nice-to-have to being table stakes very quickly. And what's strange is that for a lot of my company's lifetime,
40:49
I felt that YouTube or Twitch getting better was like worse for our business. Now it's better. Can you explain?
40:58
If you're a tier one broadcaster and you don't wanna just sell your rights exclusively to YouTube and Amazon, like you wanna have a D2C offering,
41:09
but you're competing with like YouTube TV's experience and like 1,000 engineers or whatever it is working on YouTube TV, you need a solution that's like as good as that. But you're not a tech company, and that's us.
41:24
We will help you compete with and exceed what they are doing yourself.
41:28
And the model switched from just SaaS to SaaS plus forward deployed engineers that are like in your team that are customizing our software for your needs
41:38
and accelerating your time to market dramatically, but it's still white label to you, and that was like the exact winning combination.
41:45
Part of why that's working so well is 'cause of this model of having forward deployed engineers, and we're in the sprints and we're in the conversations, we hear about problems and we hear about what they wanna solve next.
41:57
There's this very unique thing going on right now where multi-view became a very important feature for apps. YouTube put a lot of energy into it.
42:07
So like that became like this immediate thing that we just became aware of like really quickly and we're like, "Hey, here's like a solution to that problem." Mm. And so what's a metric inside the company right now
42:19
that you're more proud of than any of the named customers? It's just back to the watch time thing. After being in market with ESPN, I can't speak to the specific numbers, but after reviewing the results it was like,
42:35
there's probably a bug with Adobe Analytics I give ESPN a ton of credit.
42:39
They launched with a pretty varied set of experiences that are catering to different fan cohorts, and so they're getting a lift from those fan cohorts.
42:48
I'm proud that even with huge customers, the same result holds true, and separate from the results we're getting for our customers, the company itself is, like, a much more well-oiled machine.
43:01
What you're building now has been up for grabs for, for a few years by a few different companies. Yeah. And you've outlasted a wave of much better-funded competitors along the way.
43:14
You know, founders are coming up now facing kind of similar, like, capital wars with how much king-making there is going on these days. Totally. There's hype cycle, there's AI. What advice would you have for founders
43:27
that are facing some of those pressures from the outside world- Man... in what they're trying to build? I just feel like the game for entrepreneurs now is just so different from when I was coming up.
43:41
I know it might sound, like, antithetical or contrarian, but don't do what you're passionate about. Find something that can make money that you can be passionate about. Stakes are so much higher.
43:58
If you're not generating real ARR, good luck getting, like, your seed round or your series A. The bar is just so much higher. I used to
44:08
fight so hard against, like, "I don't wanna be put in the box that the VCs are looking for," and like, "I'm not gonna fit that. I'm gonna, like, do my own way. I'm gonna break the mold."
44:17
Please don't try to break the mold. It's not worth it. It's gonna be, like, the biggest rollercoaster of your life. You want to choose a thing that has higher likelihood of success.
44:28
The higher likelihood of success comes down to a very, very, very simple formula. Who is the customer? Where is the customer? What is the customer hiring your product to do for them?
44:45
And will they pay you to do that job for them? And then how do you, once you have the thing, reliably get in front of the customer who has your problem with your solution?
45:00
Everything else is just noise, so much noise. Will they pay you to do the thing you want to do for them? If not, don't do the thing. Stop, right? Like, I'm so guilty of this. It feels really good to build.
45:15
If you're a builder, you wanna build. You should not build. [laughs] Hold back from building, right? Especially in the age of AI, you can build anything. There's, like, literally no walls. There's no restrictions.
45:28
There's nothing. It's all the more so more important than ever to build the right thing. [laughs] Totally. [laughs] Yeah.
45:37
May- well, maybe that's a good question to ask because during COVID, all of your competitors raised way more money than you, hired way more people, had that initial revenue on the back of COVID.
45:51
But most of them are, are gone, and you're still standing. But at that time when there was all that noise in the market, and they were getting all the headlines and the capital,
46:03
what did you do with that noise, and what did you do with that envy that I'm sure must have come along of just getting hit- Yeah... with the news and headlines over and over again? It's hard to deal with. Um,
46:22
I'm not the best at dealing with it. So many things happened throughout the years, but a very large company that we had done a big project for that was successful
46:33
acquired a much smaller company in our space instead of us, and that was, like, really hard to take, and there have been, like, lots of examples like that where companies raise more money.
46:47
It's hard not to take it out on yourself. "Why am I not good enough? Why am I failing? What am I doing wrong?" And money being raised has nothing actually to do with a- any measure of success. It's correlated, maybe.
47:02
Maybe not. [laughs] Actually, if I take all the examples of all the shit that's gotten funded and died around us, it's not. [laughs] But yeah, in that moment, it's really hard. This is back to the thing in 2024.
47:14
The way that you deal with it is you're just like, "I, I have conviction. I have grit. I believe very strongly about the path we're on and where we can get to, and I can see it in my mind's eye. I can see it clearly.
47:26
I'm gonna go seek that." Um, but there's times when that whole line of thinking is overwhelmed by the other side, and as strong as you are mentally, even the strongest fall in those situations.
47:43
And how did you keep it from leaking into how you showed up at home and as a dad at those moments? Ooh. Yeah, I'm not very good at that. Um, well, that's not fair. I am good at it.
48:02
When I'm with my kids, it's like, like, my parents and, and, uh, my in-laws have, like, commented on it. It's like everything is great. You know? Like, "Oh, that's so awesome that you did that."
48:14
Like, oh, like, you know, be there with them and their excitement for their achievement, and, like, in the mundane, the mundane is amazing. You know, they're tripping, [laughs] right? You gotta remember that.
48:24
Like, the mundane is amazing. I don't know. Maybe it's, maybe I've become really good at compartmentalizing, but just trying to remember where they are and, like, keeping that, like, first and foremost. But how did you-
48:39
Keep the energy yourself, right? Because that takes- when things are not going well, all your net worth is tied to one company and household. Yeah. And then you still gotta put on
48:49
that face and be amazed by everything they're looking at. How did you, how did you carry all of that? Ooh. There's a really good book called Thinking Fast and Slow that I recommend to every human on Earth.
49:03
If you hear information, and while you hear it, you smile, you reflect more positively on the message.
49:13
Just by, like, forcing that action in yourself changes your own reflection and interpretation of the message. Sounds very simple, but, like, pretend.
49:29
Pretend to be in the state you want to be, and you will be closer to it. That's it. And is that what you did? Yeah. There's so much shit bothering me, but I'm pretending that, like, I'm tripping with you.
49:44
You're actually looking at that flower and paying a lot more attention to it than you ever have been. Oh, look at this bee. What is the bee doing? It's kind of amazing what's happening here in nature.
49:56
If you pretend like you're interested in knowing what that is and just, you can't help but, like, kind of get sucked closer to that state of, of reality, that state of being.
50:06
I feel like the experience of picturing it, uh, is so impactful to becoming it. The act of imagining something in great detail is a huge tool, huge life tool.
50:19
And whether or not it comes naturally to you, I think it can be trained to a certain extent.
50:24
It's a, it's a major life unlock for being a dad, for being a founder, for having vision, for being a leader, for being-- for just charting a course for who you wanna be. Can you take that
50:37
premise and give us an example of maybe, like, a critical decision that you had to make? There's this great quote that I love, that is, "Luck is preparedness meets opportunity." Okay?
50:53
We already had the vision and the foresight of the future that we wanted to be true, and then when the right RFP came along that we see the future the same way, it was like, boom.
51:05
That was the-- actually, the critical thing that led the company to its current trajectory was, like, that. It's hard to pin it down to one moment. We had, like, Shopify for video.
51:15
We had that product, and we were, like, ramping that up. Um, but through that process, one of the directions was going after the creator economy. We spoke to a lot of creators.
51:25
A lot of feedback that came back was, "We want apps, native apps for mobile and for TV."
51:33
So we're gonna, like, learn how to build that, and started to build, like, a cross-platform app builder, which is a part of the value prop today.
51:40
And then when this big RFP came along, it was like, "We want all your interactive stuff with your cross-platform builder tools." And it was just like, "Okay, that's, like, everything we've ever done"
51:52
for one of the biggest broadcasters, and it was like, [snaps fingers] boom. Like, the moment arrived. Did I, like, do something different to arrive there? N-no.
52:01
Believing it so much, it's both the thing that almost killed us multiple times, but also the thing that turned us into the success we are today.
52:07
So I'm not really answering your question, 'cause it's, it's a perpetual mindset. It's not a, like, moment in time, right? Mm-hmm.
52:15
This is kind of an aside, but related to, like, being a dad or to being an American or anything, right? What does it mean to be an American?
52:25
Does anyone have, like, a picture in their mind anymore of, like, what actually, like, it is we're trying to be? How are we possibly gonna, uh, become something we can't even picture the destination?
52:40
It's like with being a dad, right? If you don't have a picture of, like, the dad you wanna become, how can you be that dad? You will fail. It's impossible not to fail.
52:53
But especially with being a dad, it's like, "What kind of dad do you wanna be?" So what kind of dad does Ari want to be? Give us an image. I want my kids to exceed me.
53:04
I wanna be present with them and a big part of their life, like their best friend, but also have them respect me, which is very difficult to find that line. [laughs] I'm sure it's only getting harder over time.
53:15
Um, and commit that family has to come first. It just has to come first. It should be very rare exceptions that it's not. I'm gonna be at the soccer games. I'm gonna be at the recitals. I'm not gonna miss that, period.
53:29
That's the identity that's critical. These other things we talked-- I wanna be less short-tempered. That one's a bit harder for me. But yeah, that's the kind of dad I wanna be. I wanna be intentional.
53:43
Having intention means you have to actually think about it and chart a course. Remembering here and there to be a better dad isn't gonna get you where you need to go. Gotta picture it.
53:56
When your kids are adults and they describe their childhood, what are you afraid they will say? I don't know. I'm not really afraid of it, 'cause the chance of it's so low. But, like, you know, "We never did anything.
54:11
We never had fun. My parents never took me anywhere." I think back to my childhood, and it was just, like, such a happy place. Yeah, my parents did a great job with that. Never had need for want.
54:27
They were at all the soccer games. I got a couple of questions, uh, and then we're gonna wrap it up. So of everything that you've built at Maisha so far, and for it to be where it is now-
54:42
What's the part of you that's had to die for the company to work? [laughs] My God, man. Um, uh, definitely certain dreams. Certain dreams had to die.
55:01
Um, they're still dying. Look, any founder that's been doing anything for this long is just like, "Could I have done this faster, better, more effectively, with a better outcome, with a better result, better...
55:16
" You always believe the answer is yes. Of course, in hindsight, you could've. It's not fair to yourself to do that, [laughs] right? But yeah, that died,
55:31
and then, you know, just given where I am now, this isn't necessarily true, but it's the feeling like I've built a lot of network value and just general value of being a participant in this ecosystem.
55:44
What if I didn't wanna be in that anymore? Feels like I can't not do that 'cause, like, there's so much, um, compounding of value that's occurring. Mm. You understand compounding.
55:58
You need it to, like, go as long as possible 'cause at the end is when you're getting all the benefit, right? The max benefit. So yeah, I don't know. But also just sacrifice on, like, enjoying life more.
56:11
I have a st- I have a story and an experience from my life that really resonates for this one, which is, like, all throughout college, I took like five classes per semester 'cause I had, like, a double major and, and a minor, and I didn't have, like, a ton of AP credit coming in, and I changed majors, so it was, like, a lot.
56:27
And the last semester of school, I only took three classes, and, uh, I was like, "Oh, this is, like, what the college experience is for, like, most people, and, like, I did college wrong."
56:38
It was this, like, feeling like I did it wrong. I didn't live enough. I didn't, like, enjoy it enough, right? And I have, like, such a deep-rooted fear of that happening again to me,
56:50
like, looking back on the thing and being like, "I did it wrong." But again, it's like you gotta appreciate this is your journey, you know?
56:57
Ev- everyone has their path and, like, the path took you here, and you're pretty great. [laughs] You know, wherever you are, whatever you're doing, you're pretty freaking great, you know?
57:08
So, like, love yourself a little bit more. Yeah. Well, thank you for sharing that. Yeah. So to bring it home, what's the moment that you've been proudest of as a father? Man, I get, I get these, like, all the time.
57:24
I'm sure you'll, you'll experience this more soon because at around one a lot, this starts happening a lot more. They have to just learn the thing. So, like, my kid, um, we bought him Magna-Tiles, okay?
57:37
Which I recommend to [laughs] like any dad. [laughs] Awesome toy.
57:41
And you know, just, like, struggling to f- like, not really playing with this toy, like, struggling to understand this toy, and then, like, you know, I showed him how to, like, make a corner,
57:51
and it was like, [snaps finger] "I know how to build." And right after that day, it was just, like, building, building, building, building, build-- like, you know, the coolest things all on his own.
58:00
So proud watching him be proud. You know, um, it's been so rewarding.
58:06
And the other thing, like, you just see these genetic things, like good and bad things, but on the good side, like, I wa- I was always a sprinter when I was younger, and my son is so fast.
58:16
And you know, like, teaching my three-year-old how to, like, do a, a fast start, like, from the ground and, like, on your mark, get set, go. Like, we sprint around the neighborhood, and it's, like, the most...
58:24
It's the most incredible thing. It's just the best. You know? Oh. Yeah. That's incredible. Yeah. Sharing what you love with your kids is really fun, especially when they, like, like that thing too. You know? Yeah.
58:39
Well, this has been an incredible conversation. Thank you, Ari. Really appreciate you. Thank you. Yeah. I hope it helps other dads out there, and you know, um, feel free to send me a message if you wanna [laughs] talk.
58:54
It's, it is very lonely, uh, especially... It's double lonely. Like, the dad plus founder journey is, like, really, really hard. So, uh, you know,
59:05
be kind to yourself, and if you need to talk it out, you know, build that community 'cause it really helps. Right on. Thank you. Thank you, Matt. Talk soon. Bye.
59:21
[outro music]
Listen on
Apple Podcasts
Apple Podcasts
Spotify
Spotify
Pocket Casts
Pocket Casts
Recent episodes
Episode 01: Daniel Meth, Co-founder and CEO of Ingest AI
Jun 18, 2026
The Two Arenas Trailer
Jun 15, 2026
