Ben steps away from Tuple

April 2, 2024

After almost six years, Ben has stepped away from day-to-day work on Tuple and moved to its board. Friend of the pod Aaron Francis interviews Ben about the whole beautiful, complicated, enriching experience. As a treat, the boys dive into what's next for Aaron as well.
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Transcript

Ben Orenstein
00:00:00 – 00:00:11
You know, normally, I feel like I should introduce the guests on the show, but I think you are actually more Internet famous than I am at this point. Well, you
Aaron Francis
00:00:11 – 00:00:19
can you can you can still introduce me. That's quite that's quite alright. I would love I would love to hear your introduction for me Okay. Especially given the circumstances. What would you say, Ben?
Ben Orenstein
00:00:19 – 00:00:45
Yeah. I would say you are you are one of the rare people that is very good at making things. Like, so we you worked at Tupelo for a little while. You applied as a marketer. And you were one of the very few people that actually sent me a list of links to things that you had put on the Internet, which is, you know, really the the crux of any good application.
Ben Orenstein
00:00:46 – 00:01:11
It's like, can I click a URL that shows off why you're awesome? And you had several really good examples of that. Some of them were even Twitter threads, which I think is an underdone underdone move. But, basically, what I saw in you was this is a person who is technical and can make things that developers find interesting, which is which was the basic sketch for our marketing position. Mhmm.
Ben Orenstein
00:01:11 – 00:01:28
And so, yeah, that was I was very excited to hire you. And when I hired you, I think I even said in the announcement to the team, like, I suspect we're going to get to work with Aaron for a while until he goes and starts his own thing. Mhmm. And so I'm happy to take advantage of this narrow window. And I think I was pretty right, actually.
Aaron Francis
00:01:28 – 00:01:30
I think you were pretty right. Yep.
Ben Orenstein
00:01:30 – 00:01:31
I think we can
Aaron Francis
00:01:31 – 00:01:33
talk about that, but I think you were pretty right.
Ben Orenstein
00:01:33 – 00:01:35
We call that foreshadowing in the business.
Aaron Francis
00:01:35 – 00:01:36
Yes. Exactly.
Ben Orenstein
00:01:38 – 00:01:49
But, yes, I we have stayed so you were at Tupelo for a little while. You ended up moving over to PlanetScale, which I think was probably a better fit. Makes sense. You're, like, kind of MySQL obsessed. You're not as pair programming obsessed.
Ben Orenstein
00:01:50 – 00:02:04
So you left on good terms, and we stayed friends. And I would say that you are now one of the you're one of a small group of people that I text and that it feels like a really wonderful, valuable, like, friendship that I have as we, like, bounce ideas off each other and, like, check-in and whatnot.
Aaron Francis
00:02:05 – 00:02:12
Yeah. I was gonna, you know, do the whole podcast thing where it's like, wow, Ben. It's really good to talk to you. But, like, we actually talk a lot. It's it's delightful.
Aaron Francis
00:02:12 – 00:02:23
So this is, not super different except that we have video on. But, yeah, we text. And I think one day on, like, a Sunday afternoon, I just woken up from a nap and had a text from you. And I was like, hey. You wanna talk?
Aaron Francis
00:02:23 – 00:02:36
I was like, yeah. Let's talk. So just be bopped around the house doing stuff, talking to Ben, and, you know, it's great. I'm I'm glad that I have, a small cadre of people that I can talk to like that. It's extremely helpful.
Ben Orenstein
00:02:36 – 00:02:48
Got it. Same. Yeah. And, like, this is one of the things that makes me feel, like, super lucky and rich in a way. Like, it makes my life feel rich is, like, the caliber of people that I can text about different things
Aaron Francis
00:02:48 – 00:02:48
Mhmm.
Ben Orenstein
00:02:49 – 00:02:54
And that that I count as friends. Like, that is really kind of, like, just the currency of life to me.
Aaron Francis
00:02:54 – 00:03:06
Yeah. Yeah. Especially, especially in this space when at least I need a lot of in, a lot of insight and time to talk to people, and perhaps you do too.
Ben Orenstein
00:03:06 – 00:03:26
Yes. I would say I do. And, like, as we've kicked off this podcast, having you as, like, a adviser on it, super valuable. Like, all your video knowledge and your making of interesting marketing asset y things. Being able to text Wavin Adam Wavin, like, to have, like, someone who has high standards to look at things Yeah.
Ben Orenstein
00:03:26 – 00:03:36
And to bitch about, you know, the the challenges of running a business. Just it's just so good. It's, like, such a such a positive influence on my life. And I get to pull you in.
Aaron Francis
00:03:36 – 00:03:47
Yeah. It's good to be here. I think, I think we have at least at least one, one bombshell, one big topic, and then we could talk about me too. So where where do you wanna go from here?
Ben Orenstein
00:03:48 – 00:03:49
I wanna start with a bombshell.
Aaron Francis
00:03:49 – 00:03:51
Alright. Let's do it. Okay.
Ben Orenstein
00:03:52 – 00:03:56
I have more or less stepped away from day to day work on Tuple.
Aaron Francis
00:03:57 – 00:03:57
Okay.
Ben Orenstein
00:03:58 – 00:04:05
Yeah. After just under six years, I think the six year mark is coming up in a few weeks, which is crazy. Wow.
Aaron Francis
00:04:05 – 00:04:06
That is crazy.
Ben Orenstein
00:04:06 – 00:04:20
It's almost the longest time I spent working on anything. I was at Thoughtbot a little bit longer, but I switched projects a lot at inside Thoughtbot. So I think it's the longest I've worked on any one discrete thing. Wow. And I feel great about it.
Ben Orenstein
00:04:20 – 00:04:25
So whenever I tell people, like, yeah. I just I just stepped away from this the company I've been, like, running. And they're like, congratulations?
Aaron Francis
00:04:26 – 00:04:27
Yeah. I'm sorry.
Ben Orenstein
00:04:28 – 00:04:30
And I was like, no. No. It's good. It feels great. And I was like, okay.
Ben Orenstein
00:04:30 – 00:04:42
Great. Congrats. And I'm like, yes. So I thought you'd be a great person to talk about this with because we're friends, and I think you ask good questions. And it just felt right to have a buddy on to, like, sorta chat through this thing.
Aaron Francis
00:04:42 – 00:04:47
Yeah. I'm honored. This is exciting. So let's, let's turn the tables. Let's go back a little bit.
Aaron Francis
00:04:47 – 00:05:11
You started this, and then your roles I feel like your roles within the company even kind of changed and morphed over time a little bit in the past maybe, I don't know, maybe year or two, it's been morphing even harder. So before we get to where you're at now, give us, like, the run of started the company, ended up doing a lot of this type of work, and then we can talk about what's next. Okay.
Ben Orenstein
00:05:12 – 00:05:25
So, yeah, we start so I have two cofounders, Joel and Spencer. And, there was, like, this, like, fateful day where we're like, okay. We decided we're doing this thing. We're all quitting our jobs. And I think we're starting to talk about, like, incorporation.
Ben Orenstein
00:05:25 – 00:05:35
And I was like, okay. Who who's got what title? Mhmm. And I was like, I want the e. I I wanna be CEO.
Ben Orenstein
00:05:36 – 00:05:43
And they're like, alright. Cool. Yep. And so Spencer's CTO and Joel's COO, and great conversation to talk to you. Took it took a couple of like, a minute or two.
Ben Orenstein
00:05:43 – 00:05:55
Mhmm. And I was like, great. Awesome. So yeah. So I started off with with the e and the way that so, like, you know, what does it actually mean in a in a company of three people?
Ben Orenstein
00:05:55 – 00:06:15
Right. What the act what the actual division of responsibilities was, okay, we're all technical. Doesn't really make sense to have us all write code. And so, Joel and Spencer were off learning c plus plus and real time streaming and all this and, like, actually coding the app. And I was doing kind of all the other things, which more or less boiled down to sales, marketing, and product.
Aaron Francis
00:06:16 – 00:06:16
Mhmm.
Ben Orenstein
00:06:17 – 00:06:38
And I think, honestly, that's a pretty good description of how things went for the first good chunk of time, like like years. And Joel did more operation stuff, like, which in the early days, like, amounted to, like, cooking us lunch sometimes. Just, like, having ingredients and making lunch so we didn't have to spend so much money because we had no income. Yeah. Which actually was important.
Ben Orenstein
00:06:38 – 00:06:40
And, like, we ate well and, you know, and cheaply.
Aaron Francis
00:06:40 – 00:06:41
Yeah. I bet those are
Ben Orenstein
00:06:41 – 00:06:51
I bet those are good memories. Such good memories. Totally. And, like, there were a few meals that we he would repeat over and over, and, like, those meals still, like, feel special to me. Like, they, like, they they feel special in my heart.
Ben Orenstein
00:06:52 – 00:07:05
And, like, we've made that meal for, like, other tublers when they've joined. And, like, this is, like, the this is what we ate all the time. This is one of our go tos. It just, like, feels those were, like yeah. I mean, those honestly, and this becomes relevant, for this topic.
Ben Orenstein
00:07:05 – 00:07:28
Like, those are my those are really beautiful days. Mhmm. Like, just the the three of us against the world in Joel's second bedroom, another operations, gift of, like, you may use this space in my house, and my wife will allow it and not be too mad about it when she comes home and you guys are here still. Yes. Was was another, like, really wonderful contribution.
Ben Orenstein
00:07:28 – 00:07:41
As time went on, Joel ended up doing more operations stuff. Spencer ended up taking more of the programming burden on I pretty much stayed in, like, sales marketing product, pretty much the whole time. And so those are sort of, like, the the early years.
Aaron Francis
00:07:42 – 00:08:06
And then I feel like moving moving beyond that, y'all recently hired like, you started shedding responsibilities recently, and this is now we know as a, you know, as a move towards stepping back altogether. What was the first thing you shed? Was it sales? Like, was it proper sales, or was it something else? Because I feel like you love the product stuff and probably still do.
Aaron Francis
00:08:06 – 00:08:08
So what what did you start to let go of?
Ben Orenstein
00:08:09 – 00:08:28
I think it actually it might be worth backing up even a little bit before the shedding of responsibilities. So we hit it's something like, early COVID times. So so we we've been in the market for a year when COVID hit. So we were doing, like, nontrivial revenue. I think we had basically become raw and profitable by that point already.
Ben Orenstein
00:08:28 – 00:08:32
And so we're like, oh my god. We made it. Like, we can pay our rent. We can buy food. Mhmm.
Ben Orenstein
00:08:32 – 00:08:40
We are unstoppable. And we're still growing. And it's very exciting. COVID hit. The business, like, tripled or something in a month or two.
Aaron Francis
00:08:41 – 00:08:42
Mhmm. In a month or two.
Ben Orenstein
00:08:42 – 00:08:51
Yeah. I think one month, we added $50,000 in MRR. This is not a normal month for us now, by the way. We've never repeated
Aaron Francis
00:08:51 – 00:08:52
it. Right. Yeah. Yeah. Yeah.
Ben Orenstein
00:08:53 – 00:09:00
Or yeah. Not even close, unfortunately. But there was, like, you know, a couple months where it's just, like, it just just exploded. Wild times. Amazing times.
Ben Orenstein
00:09:01 – 00:09:12
So it's right around this time period where, we suddenly have a lot more customers. We can totally afford to hire some people. There's a lot of work to be done. And we've been at this for a while, and it's been hard. Like Mhmm.
Ben Orenstein
00:09:13 – 00:09:26
Going from being web developers to coding a native app in c plus plus with real time streaming is not easy. And Spencer bore the brunt of that. Mhmm. And so he was like, we gotta hire somebody to help me. And we're like, okay.
Ben Orenstein
00:09:26 – 00:09:32
Yeah. And we found somebody. And his name was Mikey, still with us. It's awesome. Yeah.
Ben Orenstein
00:09:33 – 00:09:39
And we're like, we gotta hire Mikey. He's like, there's not a lot of people that have, like, experience in the technologies that are relevant to us.
Aaron Francis
00:09:40 – 00:09:43
No. Y'all y'all were playing on hard mode for sure.
Ben Orenstein
00:09:43 – 00:09:46
Exactly. We can't just be like, we need a Rails developer. Oh, no problem. Like, well, that's not
Aaron Francis
00:09:46 – 00:09:50
the problem. Throw a stone. I could hit one. Yeah. Not not so much.
Ben Orenstein
00:09:50 – 00:09:54
Yeah. Not so much in our space. So we're like, okay. We found somebody. He's got a lot of macOS specific experience.
Ben Orenstein
00:09:54 – 00:10:03
He knows c plus plus really well. He's built products before. Spencer really likes him. And so we're like, we gotta hire this guy. But he works he lives in France.
Aaron Francis
00:10:03 – 00:10:05
Nice. And so
Ben Orenstein
00:10:05 – 00:10:18
I was like, okay. Are we a remote remote company? And the answer, like, wasn't totally clear actually because all the three of us, we're all in the same place. Right. And I sort of felt this thing was like, okay.
Ben Orenstein
00:10:18 – 00:10:32
It's COVID. So, like, even if you even if we weren't a remote company, we definitely are right now. Like, we were working together. We decided to, like, pot up and, like, it was it was important to us to be able to work together in person. So we took the risk of, you know, hanging out with each other and working together every day.
Ben Orenstein
00:10:33 – 00:10:40
But so it's like, okay. Even if we are gonna say we're an in person company, we can't hire somebody for who knows how long. And boy, do we need the help.
Aaron Francis
00:10:40 – 00:10:41
Right.
Ben Orenstein
00:10:41 – 00:10:44
And we are a remote collaboration tool.
Aaron Francis
00:10:45 – 00:10:45
Right.
Ben Orenstein
00:10:45 – 00:10:55
Yep. It's a bit absurd to say, come to Boston. You must come to Boston to work on our remote collaboration tool. These things are clearly yeah. This this all feels very clear and obvious.
Ben Orenstein
00:10:56 – 00:11:29
At the same time, I know in my heart that I am an in person person. Yep. And I want to work in an office with people. And I remember debating this sort of question with a bunch of people, coaches and friends and all this, and going back and forth and saying, like, I think for me, I know what I want, but I think the company probably needs something different. But if I do the thing that optimizes for the company, I feel a bit like I'm setting a timer.
Ben Orenstein
00:11:30 – 00:11:33
And eventually, that timer will go off and I will want to leave.
Aaron Francis
00:11:33 – 00:11:34
And here we are.
Ben Orenstein
00:11:34 – 00:11:43
Here we are. And so I was right, and the timer took about four to five years to go off. Mhmm.
Aaron Francis
00:11:43 – 00:11:44
Which is a long time.
Ben Orenstein
00:11:44 – 00:11:50
Which is a long time. But it's basically what happened. So we started hiring remotely. We said, okay. Yep.
Ben Orenstein
00:11:50 – 00:11:56
We're we're doing it. We're distributed. It it makes too much sense. It makes sense for the business. It makes sense for dogfooding the product every day.
Aaron Francis
00:11:56 – 00:11:57
Totally.
Ben Orenstein
00:11:57 – 00:12:06
And, you know, I still got my boys with me. I got Spencer here. I got Joel here. The headquarters is clearly here outside Boston. Mhmm.
Ben Orenstein
00:12:06 – 00:12:28
We will hire remote folks, and we'll run it from this location. At some point, not too long, maybe it's a maybe a year later, maybe 2021 or so, a property comes for sale on this island off the coast of Maine where Spencer's family has been going for something like eighty years. And it's a beautiful place. He's got a personal connection to this place as well. Mhmm.
Ben Orenstein
00:12:29 – 00:12:51
It's it's gorgeous. It's where it's it's where he wants to be. And he's, like, sort of always wanted to, like, have a spot on this island, and he decides to buy it. And I feel at the time, like, I I'm sort of sad about this, but I wouldn't Mhmm. I can't imagine stopping you or or even asking you not to do this because, like, part of the point of starting a company is to achieve your dreams.
Ben Orenstein
00:12:52 – 00:12:52
And
Aaron Francis
00:12:52 – 00:12:52
Exactly.
Ben Orenstein
00:12:53 – 00:13:16
The starting of the company helped him achieve this dream. And so why would I you know, it made no sense. But, again, what ended up happening is Spencer started spending more and more time at this house, of core because, of course, it became his more or less his primary residence. And so suddenly, our, you know, run this distributed company from a central location became, one of my cofounders is also distributed. Yep.
Ben Orenstein
00:13:16 – 00:13:32
Which definitely changes the feel of it a lot. And now we're not just like, you know, we don't decide internally and then fan out the information. It's like now we are truly, like, all things have to work in a distributed fashion, which again is probably good, actually. Like, we we it helps fix that.
Aaron Francis
00:13:32 – 00:13:33
For the company, maybe.
Ben Orenstein
00:13:33 – 00:13:43
For the company. Exactly. But but also, you know, good for the company, less good for Ben. Right. But we sort of soldier on, and I keep going.
Ben Orenstein
00:13:43 – 00:13:55
And, honestly, like, oh, I do wanna be clear that, like, most of the most of this was fantastic. Like, I'm mostly having a great time. Like Mhmm. The business worked, which is, like, really makes it a lot more fun. I
Aaron Francis
00:13:56 – 00:13:57
Sure does. As expected.
Ben Orenstein
00:13:57 – 00:13:58
So it's like Revenue
Aaron Francis
00:13:58 – 00:14:01
revenue solves a lot of problems. Yeah. Yeah.
Ben Orenstein
00:14:01 – 00:14:18
Yes. Revenue go up, like, equals happy. Because, you know, I wish it weren't so connected, but, the reality is it's still, like, it's still great. And, like, I'm having deeply fulfilling, rich, interesting experiences. And it's the most interesting professional thing I've done by an order of magnitude.
Ben Orenstein
00:14:18 – 00:14:44
And I'm feeling fortunate and blessed and appreciating my coworkers. And we get to hire great people, and I get to learn like, work with you and become friends with you and and times all of the other people on the team. And, also, I feel a bit like I'm sort of marching up the wrong mountain. Mhmm. Where it's like, do I wanna become really great at being the CEO of a remote distributed company?
Ben Orenstein
00:14:45 – 00:15:12
And the answer is like, not really. And as we get larger, the sort of management y bits become harder and more required. Yeah. And, like, I like kicking around product ideas at lunch And then having someone, like, roll their chair over to my desk and be like, what do you think of this? And then kinda like a like a slapdash y, kinda casual, sloppy product management style, I guess.
Aaron Francis
00:15:12 – 00:15:17
Yeah. A little a little bit of beebopping. You love to jam. I like to jam.
Ben Orenstein
00:15:17 – 00:15:40
Exactly. Yep. And when when it started to be more like, well, no. We really need you to, like, write out what you want in, like, pretty clear detail so you can hand it off to someone that lives in a different country and has a bit of a time zone difference from you. And then that person needs to, like, schedule time to show it to you or, like, sort of all the, you know, all the challenges of a remote thing, it sort of it sort of saps some of my joy.
Ben Orenstein
00:15:41 – 00:15:53
Mhmm. And so I just sort of have this continual tension of, wow. This is the most interesting thing I've ever done professionally, and it's mostly great. And I don't feel like this is my global maximum great.
Aaron Francis
00:15:53 – 00:15:55
Right. And so I live with
Ben Orenstein
00:15:55 – 00:16:08
that tension for years. And eventually, the timer starts, like, ticking ticking down. And it goes from, like, this is this has some drawbacks. This isn't quite globally optimal for me, but it's mostly great. To being more like, no.
Ben Orenstein
00:16:08 – 00:16:18
I really am starting to feel that feeling of, like, I shouldn't walk further up this mountain. Mhmm. And so I get kind of I start to lose my mojo.
Aaron Francis
00:16:19 – 00:16:19
Yeah.
Ben Orenstein
00:16:20 – 00:16:28
And yeah. So, like, say, like, 2022 or so, maybe early twenty three, I'm kinda just not having a great time.
Aaron Francis
00:16:29 – 00:16:54
Mhmm. At that point, you feel like you're going you're going on a track that is leading you somewhere that you don't want to be. One of your best friends has moved away, and so your little your little tripod is now, I don't know what that would be, two people. And it seems like I I'll I'll put words in your mouth. To me, that would feel like the good old days are behind us, and I miss that.
Aaron Francis
00:16:54 – 00:16:56
Is that kinda how you felt?
Ben Orenstein
00:16:57 – 00:17:06
Yeah. Yeah. More or less. And I hate to characterize it, you know, as is like because that feels just like purely negative. They're they're a part of me inside.
Ben Orenstein
00:17:06 – 00:17:07
A part of my heart hurt
Aaron Francis
00:17:07 – 00:17:08
Of course.
Ben Orenstein
00:17:08 – 00:17:39
Because, yes, the the good old days to me were us in the bedroom or at least, you know, together in person. And, you know, it's not to say that the rest that there wasn't lots of great stuff too. But, yes, it did feel a little bit like, I feel like I had this thing that was that was, like, the thing I wanted, and it sort of slipped through my fingers. And now I have a thing that is still good, but it's not quite what I want. And so I am not great at making myself do things like when I have kind of like fallen out of love with the thing.
Ben Orenstein
00:17:39 – 00:17:55
And so I would say my performance as CEO suffered during this period. It's like, I think that's just fair to say. And it's you know, that's a company controversially should probably have a leader that is excited to lead that company.
Aaron Francis
00:17:55 – 00:17:57
That's a very hot take. You're brave to say
Ben Orenstein
00:17:57 – 00:18:02
it. Yeah. Excited about the constraints of that. Like, excited about the full deal. Right?
Ben Orenstein
00:18:02 – 00:18:15
Looks at the whole package and says, this is cool. Like, I'm I'm stoked to do this. And for me, I was just sort of, like, I was struggling. Yeah. And I didn't I really I sort of didn't see a way out.
Ben Orenstein
00:18:16 – 00:18:41
I thought kind of like, I feel like I have to keep running the company or otherwise it will be negatively affected. And even if I didn't feel that way, I don't know what I wanna do next. Mhmm. And I'm really scared to leave without knowing that thing. And I think a lot of that fear came from this experience I had earlier, when I left and I did a sabbatical when I was at thought, but, and I took something like four months off.
Ben Orenstein
00:18:42 – 00:18:50
And the first week was amazing. It's like, woah. I have no responsibilities. This is incredible. And by the second week, I was like, oh my god.
Ben Orenstein
00:18:50 – 00:18:57
I haven't left the apartment in several days. Yep. No one cares where I am or what I'm doing. And, actually, that feels bad.
Aaron Francis
00:18:57 – 00:19:00
Yes. The crushing weight of nothingness.
Ben Orenstein
00:19:01 – 00:19:07
Yeah. Totally. And I was like, oh, no. I need structure. Otherwise, bad things happen.
Ben Orenstein
00:19:08 – 00:19:13
And I fortunately was able to find some structure. I ended up teaching at a friend's boot camp out in Denver.
Aaron Francis
00:19:13 – 00:19:13
Oh, cool.
Ben Orenstein
00:19:13 – 00:19:36
Which gave me exactly what I wanted, a bunch of in person interaction, a place to go every day, people expecting me to do something, feeling useful. But I really think I that that lasted a month, and then I had I took another couple more months off, and I kinda felt wander y. And I kinda felt this, like, this sadness and malaise and loneliness. And I think I over corrected based on that lesson.
Aaron Francis
00:19:36 – 00:19:37
Interesting.
Ben Orenstein
00:19:37 – 00:19:49
And I think I sort of set this thing in my head, which is like, you can't not know what's next. Because if you don't have structure, you will be very sad. And I remember expressing this to Spencer and him saying, like, well, you should fix that, dude.
Aaron Francis
00:19:49 – 00:19:53
Like, you should know what, like Good good job, Spencer. Yeah. Way to go. You should
Ben Orenstein
00:19:53 – 00:20:08
be able to, like, go live a life and, like, find some stuff that excites you. Like, if you don't feel that way, you should probably fix that, which I think is correct, actually. Yeah. But I felt stuck. Fortunately, I have two really good cofounders.
Ben Orenstein
00:20:09 – 00:20:31
And one day this summer sorry. Last summer, we did, we do quarterly, like, leadership retreats. And so Joel and Spencer and I and Steven, who was our COO, someone we've sort of hired since then, who became an important part of the leadership structure. We meet up on that island, and we check-in. How's everybody doing?
Ben Orenstein
00:20:31 – 00:20:53
And for maybe, like, the third or fourth one of these in a row, I say something like, yeah. Like, some days are, like, really good. And, like, I'm feeling, like, really stoked about Tupelo, and I'm really enjoying it. But it never seems to last that long, and I kinda keep feeling like I just go off the rails a little bit. And they more or less tell me, like, you don't have to do this anymore.
Ben Orenstein
00:20:55 – 00:21:15
And maybe you shouldn't, which was a thing that I had thought. But to have someone else say it was kind of like, oof. It's like it's not just in my head where I'm like, I'm not sure I don't think I'm doing a great job right now. Mhmm. They were kinda like, you either need to, like, get excited about this or you should stop doing it.
Ben Orenstein
00:21:15 – 00:21:24
Said with compassion and care and love as friends. Mhmm. But still, it was kinda like, oof. Okay. I'm not I'm not secretly suffering.
Aaron Francis
00:21:24 – 00:21:25
Mhmm.
Ben Orenstein
00:21:25 – 00:21:29
My performance is not quietly degrading. It's kinda like everyone's sorta like, it's not
Aaron Francis
00:21:29 – 00:21:30
that fault. Yeah.
Ben Orenstein
00:21:30 – 00:21:37
Yeah. We know. And, you know, we also think the company should have a leader that is really stoked, and you're not doing that right now.
Aaron Francis
00:21:37 – 00:21:56
Did you feel a great sense of relief when they said, dude, you don't have to do this? Because those are the people, you know, of course, all of the employees, but your cofounders are the people to whom you probably felt the most responsibility and, like, the most Yeah. Like, you owed the most to those two or, you know, three if you include Steven people. And for them to say, hey, man. You you don't have to do this.
Aaron Francis
00:21:56 – 00:21:57
Was that a relief?
Ben Orenstein
00:21:59 – 00:22:27
Not right away. It was kinda just hard in the moment, honestly. And, Spencer, like, I remember such a clear the really clear point to me happened when Spencer said, like, Spencer kind of it felt like he was kind of trying to save me a little bit, like like a diving safe for Ben, a CEO. And he's kind of like he said something like, I know you can do this. Like, I know you can be an incredible CEO for Tupelo, and I just I want to see you do this.
Ben Orenstein
00:22:27 – 00:22:50
Mhmm. And I sort of looked in myself when he said that, and I just felt like I just but the thing that came back, which is kinda like, no. I'm not gonna do it. Like, nothing stirred in me Right. Of, like like, he gave I mean, it was, like, a really great motivational kind of prompt, and I just got emptiness back from inside me.
Ben Orenstein
00:22:50 – 00:22:54
And that's when I, like, really knew. I was like, no. I can't. I'm not gonna do this. I can't do it.
Ben Orenstein
00:22:55 – 00:23:07
And so, really, fortunately, once we sort of agreed that it shouldn't be me, Spencer stepped up and, like, offered to do it.
Aaron Francis
00:23:08 – 00:23:12
Did that agreement happen that on that retreat, or did you take It did. Wow.
Ben Orenstein
00:23:12 – 00:23:33
It did. And in fact, to credit credit to Steven, Spencer talked about some I think it was some person that he had hired or, like, some sort of extraordinary effort he had gone through to sort of stay in touch with the candidate or something. Mhmm. And Steven said, it kinda sounds like CEO behavior to me. And we were all like, And we had been sort of picturing like, okay, we need to start a CEO search.
Ben Orenstein
00:23:33 – 00:23:37
And I was like, that does kinda sound like CEO behavior.
Aaron Francis
00:23:37 – 00:23:39
He was here this whole time.
Ben Orenstein
00:23:39 – 00:23:52
Spencer, do you wanna be CEO? And he was like, maybe. And so we agreed that we would like to think of, like, sleep on it for a night. And we all slept on it for a night, and I woke up and I was like, yeah. That seems good to me.
Ben Orenstein
00:23:53 – 00:23:57
And we all felt that way in the morning. And so Spencer became CEO.
Aaron Francis
00:23:58 – 00:24:12
Wow. And I don't wanna tell Spencer's story or or you to tell Spencer's story, but I feel like he, took a little bit of a step back for a while too. And now he's, like, he's stepping up big time. So of what you can say, like, what was the story there?
Ben Orenstein
00:24:13 – 00:24:34
I think at various times in the company's history, each of us has had, like, kind of a burnt out period Mhmm. To varying degrees. And I think Spencer had it maybe the strongest, which is fair because he was under, I think, the most pressure. Yeah. Like, the sales and marketing and product were all kind of in my wheelhouse Mhmm.
Ben Orenstein
00:24:34 – 00:24:52
And they were going pretty well. And this whole, like, learn this whole new area and try to build this complicated app. And by the way and, like, we sort of honestly, we should have hired someone sooner. Like, when we hired Mikey, it was it was late. Seltzer had worked, like, so hard to, like, make this thing work and keep it going and poured himself into this problem.
Ben Orenstein
00:24:52 – 00:24:55
And, learning it all
Aaron Francis
00:24:55 – 00:24:56
from scratch, by the way. Right?
Ben Orenstein
00:24:56 – 00:25:03
Learning it all from scratch. Yeah. Which is, like, a such a strength of his. Like, a willingness to just throw himself into it. Like, I have to learn all this stuff.
Ben Orenstein
00:25:03 – 00:25:07
Okay. Here's how I will do it. Here are the books. Here are the coaches. Like, that is his thing.
Ben Orenstein
00:25:07 – 00:25:24
And and the thing that he's amazing at. But I think we didn't really appreciate, like, how much we had asked of him. Yeah. And and, like, what it had taken out of him. And so I think Spencer had to sort of like, I'm kind of burned out moments more strongly a bit earlier.
Ben Orenstein
00:25:25 – 00:25:50
And so there was a period where he was looking to step back and we sort of just, like, didn't get it done. Like, we were trying to hire a CTO for a while, and I think this is, like, kind of during a time where I was not where I was, you know, I was I was still kinda struggling. And we kinda couldn't find anybody, and that idea just kinda died. And and it's kinda like, do you mind just, like, kinda keeping going? And he was like, okay.
Ben Orenstein
00:25:51 – 00:26:07
And I think he like, he took some time off in there. Like, we found some ways to, like, get him some space and some time, and I think he feels felt okay about, like, continuing to do that. And, actually, now, I think he might be at his most stoked. Danger of putting words in people's mouth. Sure.
Ben Orenstein
00:26:07 – 00:26:11
But, I think there is a I think there has been a reinvigoration.
Aaron Francis
00:26:11 – 00:26:30
That's amazing. It sounds to me like just as kind of a tangent. The three of y'all have an incredible relationship. I mean, if you went through that and Spencer went through that and who knows what Joel went through and everybody is still together and still best buds, it's like, that is something to be prized. I don't think that's very common.
Ben Orenstein
00:26:30 – 00:26:41
I super agree with that. I feel very lucky. Yeah. I think, like, I won the cofounder lottery. And I think the three of us in particular have such different strengths Mhmm.
Ben Orenstein
00:26:42 – 00:26:59
That we, like, really like, together, the triumvirate, like, really presents a pretty strong it's like a pretty, like, strong combo. And part of, I think one of our strengths is that we do, like, just deal with stuff really well. Mhmm. And there's so many things to deal with. You know, there's so many hard conversations and tricky things and possible disagreements.
Ben Orenstein
00:27:00 – 00:27:11
And I would feel like we've had given what we've been through, we have, like, so little conflict and have, like, resolved stuff so well. Yeah. So as always, shout out to my cofounders Yeah.
Aaron Francis
00:27:12 – 00:27:12
Who made this
Ben Orenstein
00:27:12 – 00:27:13
all possible.
Aaron Francis
00:27:13 – 00:27:25
Give given people you can trust and the ability to communicate, you can solve pretty much anything, and it sounds like you'll have. So that's pretty awesome. So you have this retreat. Spencer's like
Ben Orenstein
00:27:25 – 00:27:25
Mhmm.
Aaron Francis
00:27:26 – 00:27:31
I'm I'm CEO now, and Ben is now what? What happened? Like, where do you go from there?
Ben Orenstein
00:27:32 – 00:27:39
Right. So we agree that Tupelo still needs a product person. K. Like someone with, like, really good product
Aaron Francis
00:27:39 – 00:27:40
taste.
Ben Orenstein
00:27:40 – 00:27:55
And so okay. I can step out of the CEO position, but we need a product to be managed still. And so I basically I moved ahead of product. It becomes my new title. And the idea is, okay, I'm not gonna do marketing or sales or hiring or any of this, or, like, high level strategy necessarily.
Ben Orenstein
00:27:55 – 00:28:04
I'm just going to be focused on product work. Mhmm. And it's it's really hard. Mhmm. I like I go home to my parents and I cry.
Ben Orenstein
00:28:05 – 00:28:16
Like, it is it it there was some relief in, like, okay. I'm finally on this path of, like, moving away from this thing that I feel like I had to do. Mhmm. But But it still felt pretty terrible.
Aaron Francis
00:28:17 – 00:28:20
The work itself or, like, where you saw yourself heading?
Ben Orenstein
00:28:21 – 00:28:26
Sorry. Yeah. Yeah. So yeah. So he make me head a product, but, like and then I go home that day Mhmm.
Ben Orenstein
00:28:27 – 00:28:44
And am, like, pretty distraught. And that continues for a decent bit. Like, it is I was kind of shocked at the degree to which no longer being the CEO, like, kinda crashed my ego. Right. And I had, like, a lot of myself wrapped up in this identity that had been mine for a long time.
Ben Orenstein
00:28:45 – 00:28:53
And I felt like I felt a little bit of shame, whereas, like, I didn't go out on a, like, a high note. Mhmm. You know? Like, hey. We're crushing it, and I'm I'm gonna run off into the sunset.
Ben Orenstein
00:28:53 – 00:28:55
It was like, I am crushed.
Aaron Francis
00:28:55 – 00:28:55
Right.
Ben Orenstein
00:28:55 – 00:29:12
And I am very sad. And, like, I agree this is the right thing to do, and it still hurts a lot. So I won't lie to you. It was it was a tough couple weeks, I would say. And we have this now really tricky situation to negotiate where it's like, okay.
Ben Orenstein
00:29:12 – 00:29:31
I still work at the company. I've given all this control and responsibility to somebody else. I haven't really solved my problem yet. I'm not really on the path, that I feel like I still there's still constraints here. And there's this weird social thing, which is just like the leadership just changed dramatically.
Aaron Francis
00:29:31 – 00:29:32
Right.
Ben Orenstein
00:29:32 – 00:29:53
And how do we negotiate this? And, like, I want Spencer to be successful, and Spencer wants me to be successful. But like any human relationship, we are somewhat frequently mismodeling the other person. Right. And I am deferring to him in ways that he does not want me to do, and he is trying to make my work life better in ways that I don't actually appreciate or don't want.
Ben Orenstein
00:29:54 – 00:30:01
And And we are sort of just, like, trying to help Yes. Each other and meaning well and not quite nailing it and missing Yeah.
Aaron Francis
00:30:01 – 00:30:12
We call that leping. It's a it's a typo for help. It's h l e p. It's like when you really try to help, but you make it worse, dad slept a lot. You're like, dad, I actually I don't need you to help with that.
Aaron Francis
00:30:12 – 00:30:22
You that's you're actually making this worse, and I'm I'm bracing myself for that as a dad. But it's like, hey. I appreciate that effort. This actually is not helping.
Ben Orenstein
00:30:23 – 00:30:31
That's yes. Oh, man. That was such a great concept. I can't I I'm so glad you brought that up because I can't wait to deploy that. That was, like, such a great place to hang that, like, idea because that is yeah.
Ben Orenstein
00:30:31 – 00:30:37
That's totally a thing. We're real hyping each other a lot. Yep. And even if we had done it perfectly, it was still hard. Mhmm.
Ben Orenstein
00:30:38 – 00:30:45
Like, it's just tough. I mean, there's ego involved. There's complex social dynamics. Like, imagine being at Tupelo that time. Yeah.
Ben Orenstein
00:30:45 – 00:30:57
And, like, suddenly, this change is happening. You're like, oh, okay. How do I handle this? And, like, yeah, it's kinda weird. So it's a bit of a rough transition, but we do it overall, I would say, pretty well.
Ben Orenstein
00:30:57 – 00:31:12
Like, over like, considering the challenges there, it doesn't take that long. And within a couple months, actually, I think we're kind of, like, settled in. And so this is, like, fall ish, maybe, like, early winter twenty twenty three. We're, like, we're actually kinda there. Mhmm.
Ben Orenstein
00:31:12 – 00:31:20
And, like, it feels like it's starting to work. And I'm seeing Spencer be CEO, and he's doing a good job. And I'm like, okay. Nice. It's like Feels good.
Ben Orenstein
00:31:20 – 00:31:31
Goodness. And, like yeah. And that feels really great. And once again, he's doing the thing he does, which is, like, he learns the things he has to learn. He finds the coaches he has to find.
Ben Orenstein
00:31:31 – 00:31:36
He gets the support he needs, and he's taken on the a hard thing and and thrown himself into it.
Aaron Francis
00:31:36 – 00:31:52
He is so good at, finding external support, whether that's pair programming coaches for learning new languages or business. He's just like, I wish I was better. I wish I even had that thought. It's not like I think about it and then I'm like, I don't need a coach. It's like, oh, wow.
Aaron Francis
00:31:52 – 00:31:55
There are actually coaches out there for that. You know, he's good at that.
Ben Orenstein
00:31:55 – 00:32:01
Yeah. Totally. Yeah. He has the right I I think he has great impulses when he's, like, got a new challenge. Mhmm.
Ben Orenstein
00:32:01 – 00:32:12
And that was one of the things he he promised the team when we announced him taking over was he's like, I don't know how to do all of the things the CEO needs to know how to do right now, but I will learn them.
Aaron Francis
00:32:13 – 00:32:14
That's what you want.
Ben Orenstein
00:32:14 – 00:32:26
That's what you want. So around this time period, we hire a really important person. His name is Eli, and he is starts off as a product lead for us.
Aaron Francis
00:32:26 – 00:32:29
I got an email from Eli this morning, in fact. Yes.
Ben Orenstein
00:32:29 – 00:32:30
You did.
Aaron Francis
00:32:30 – 00:32:30
It was a great email.
Ben Orenstein
00:32:30 – 00:32:33
Uh-huh. Yeah. Eli knows how to write a good email.
Aaron Francis
00:32:33 – 00:32:34
He does.
Ben Orenstein
00:32:34 – 00:32:37
Which is the thing I love in a person. Yep. A good email.
Aaron Francis
00:32:37 – 00:32:37
If you
Ben Orenstein
00:32:37 – 00:32:38
can write a good email,
Aaron Francis
00:32:38 – 00:32:40
straight to Ben's heart. That's the way.
Ben Orenstein
00:32:40 – 00:32:44
Uh-huh. Uh-huh. Yep. That is the that is my love language. It's great emails.
Ben Orenstein
00:32:45 – 00:32:48
Great writing. And you wrote a great post today, by the way.
Aaron Francis
00:32:48 – 00:32:50
Oh, thank you. Straight to your heart, I hope.
Ben Orenstein
00:32:50 – 00:32:59
Yes. It did. Yeah. Absolutely. And, I'm pretty candid with Eli actually pretty early on, which is, like, I view you as my eventual replacement.
Ben Orenstein
00:33:00 – 00:33:21
So, like, I'm excited to work with you and excited to, like, teach you the things that I think I know probably. But I think you're the guy. And it turns out it seems like that was right. Eli is amazing from the start and just kind of we hire him ostensibly to run a small project within the company. Mhmm.
Ben Orenstein
00:33:21 – 00:33:34
And very quickly, he has sort of tactfully, intelligently gobbled up more of all the surrounding projects as well. And I'm very and much to my happiness. Right. This is what I want.
Aaron Francis
00:33:34 – 00:33:37
You're you're actively ceding ground to him. Yeah.
Ben Orenstein
00:33:37 – 00:33:53
Absolutely. Yes. Absolutely. And it feels great because you try to see, like, oh, this is what a really engaged product leader looks like. This is what someone who's fresh and excited does and also who has more experience working remotely than I do.
Ben Orenstein
00:33:53 – 00:34:18
And like, this is how you like has all this, like, wisdom. And so pretty fast it's like I'm starting to feel the feeling like, okay, I think actually I can hand off the last thing I'm doing. As that feeling starts to build and, right around this time, Joel's wife has a baby. And so Joel has been my work buddy Yep. Since Spencer left.
Ben Orenstein
00:34:19 – 00:34:24
Or, like, he's the other guy coming to the office. So we have a little co working space near our houses. And I
Aaron Francis
00:34:24 – 00:34:26
see where this is going.
Ben Orenstein
00:34:26 – 00:34:33
Yes. And Joel and I are not working together together, but we work next to each other. And we talk about work. And we go to and we have lunch. Yep.
Ben Orenstein
00:34:33 – 00:34:56
And we, you know, go to yoga. And we're we're, like, very, very close friends and work buddy work work acquaintances, you know, like, we sort of yeah. And when, Joel's wife is getting close to having this baby, he basically says, I think, actually, I'm just gonna step away. Mhmm. Like, Like, I'm gonna take paternity leave, but also, like, I think I should probably just, like, shed my two responsibilities.
Ben Orenstein
00:34:56 – 00:35:03
And, like, maybe I'll come back. I don't know. But let's let's not assume that, I guess. And yeah. I think I'm mostly stepping away.
Ben Orenstein
00:35:03 – 00:35:12
And I might just wanna take care of my baby for a while. Yep. And which is, you know, again, a beautiful accomplishment of dreams.
Aaron Francis
00:35:12 – 00:35:20
Exactly. What a beautiful, wonderful thing that is great for him and makes Ben sad. Like, yep. Again.
Ben Orenstein
00:35:21 – 00:35:23
Yep. Again. So happy for you.
Aaron Francis
00:35:23 – 00:35:28
So happy for you. So sad. So happy. So still a little sad for myself, though.
Ben Orenstein
00:35:28 – 00:35:45
Yep. And five or six weeks ago, it's like Joel's official, like, last day happens. And some number of weeks ago, about that long, I wake up in the middle of the night. It's, like, 3AM or something. It's been a couple days since Joel's, like, official last day.
Ben Orenstein
00:35:46 – 00:36:01
And I realize there's no office for me to go to with anybody in it. And I just kinda start sobbing in bed, just curled up crying. And I feel like I'm sort of mourning the end of an era.
Aaron Francis
00:36:01 – 00:36:02
Of course.
Ben Orenstein
00:36:02 – 00:36:08
It's like that that part is now it's just really gone now. Yeah. Like, it was, you know, it was kinda gone before, but now it really is.
Aaron Francis
00:36:08 – 00:36:15
If this is a sitcom, this is where everyone moves out of the apartment, and they look back and they think, wow. We had some good times in the apartment, didn't we?
Ben Orenstein
00:36:15 – 00:36:22
Yep. Yep. Yep. And I'm feeling that hard, and it hurts. And it doesn't last that long, though.
Ben Orenstein
00:36:23 – 00:36:42
So I, like, I'm crying, and I kinda stop. I, like, let the the grief comes out, And then I feel this, like, like, clarity kind of hit me all at once, which is like, I'm getting out of here. I'm gonna I'm gonna drop my involvement at Tupelo down to, like, a minimal level, and I'm gonna go to New York City.
Aaron Francis
00:36:43 – 00:36:45
Oh, so getting out of here and here means everything.
Ben Orenstein
00:36:46 – 00:37:06
Here means everything. Because I'm also thinking about my life in Somerville, the city I live in outside Boston. And it feels like it has also sort of shrunk. And, like, in the previous months, I sort of noticed, like, a number of my friendships have kind of drifted apart a little bit. And I'm doing fewer activities, and I'm feeling less value, like, about where I live.
Ben Orenstein
00:37:06 – 00:37:12
Mhmm. And I I met somebody, and he was like, oh, like, where do you live? And I was like, oh, Summerville. He's like, oh, wow. He's like, you could live anywhere.
Ben Orenstein
00:37:12 – 00:37:17
Right? And I'm like, yeah. Because, like, we we're remote. I could go live anywhere I want. And he's like, oh, so you must, like, really love Summerville.
Ben Orenstein
00:37:17 – 00:37:19
It must be, like, the perfect place for you because you could be anywhere.
Aaron Francis
00:37:19 – 00:37:21
And you're like, and I was like, hang on.
Ben Orenstein
00:37:22 – 00:37:25
Yeah. I guess that's
Aaron Francis
00:37:26 – 00:37:29
true. You well meaning stranger. You've just thrown me into disarray.
Ben Orenstein
00:37:30 – 00:37:44
Yeah. Yeah. I guess I agree with that. I'm having trouble justifying that position currently, but I'm sure I could. And so I'm already kinda like, is this the right place for me?
Ben Orenstein
00:37:45 – 00:37:55
And at 03:30 in the morning post cry, I'm like, no. It is not. Yep. I'm getting the hell out of here. I need to change.
Ben Orenstein
00:37:55 – 00:38:12
Mhmm. I need my life to be different. I'm, like, way too in my current rut of this place I've been for a long time. And I need I need to shake everything up, like, right now. And so very quickly, I tell the guys, like, alright.
Ben Orenstein
00:38:12 – 00:38:36
I'm gonna go down to a max of ten hours a week. And I wanna we're gonna promote Eli to head of product because he obviously is the head of product. This is just correcting the the record. And I'm going to New York and I'm gonna, like, look for adventure and interesting things to happen. And that plan has been running since then, and that has happened.
Ben Orenstein
00:38:36 – 00:38:45
You got an email from Eli, come ahead of products today. I did. That's the thing. I'm officially out. I I left the leadership channel on Slack.
Ben Orenstein
00:38:45 – 00:38:51
Wow. Mhmm. So I am not on the leadership team. Now I'm on the I'm on the owner's team. Man.
Ben Orenstein
00:38:52 – 00:39:00
I'm an adviser to Tupelo. I am a resource for Eli when he wants it. I'm happy to take a call with anyone that needs it. I record this podcast. Yep.
Ben Orenstein
00:39:01 – 00:39:06
And that is that is what I'm doing. That's my involvement with the company right now.
Aaron Francis
00:39:07 – 00:39:19
Wow. Rarely are there such symbolic discrete actions as leaving the leadership channel Mhmm. In Slack. It's like, this is the this is the point. Like, this is the head of the spear right here.
Aaron Francis
00:39:19 – 00:39:23
It is happening. Had to feel kinda weird.
Ben Orenstein
00:39:24 – 00:39:25
Honestly, it felt really good.
Aaron Francis
00:39:25 – 00:39:27
There there's the relief. Okay.
Ben Orenstein
00:39:28 – 00:39:37
It felt right. Yes. It has finally felt right. It wasn't until I got until, like, this last phase Mhmm. Of, like, actually, I wanna renegotiate my commitment to the company.
Ben Orenstein
00:39:37 – 00:39:56
Mhmm. I want to, like, set my compensation appropriately given that thing. I want to tell everyone that I'm doing this thing, and I want to be open with the fact that the reason I'm doing this is because I am now trying to find the next thing for me. Yep. And once I did those things and came to New York Mhmm.
Ben Orenstein
00:39:57 – 00:40:02
And started meeting really interesting people, it all started to feel really, really good.
Aaron Francis
00:40:02 – 00:40:25
So judging from the outside, you know, of course, I have inside info. But just judging from the outside, I feel like I am witnessing the rebirth of Ben. I feel like this is this is you kind of coming back into your zone of not only expertise, but, like, joy and happiness. I mean, you're putting out these you're putting out these videos on Twitter that are just, one, going crazy. Everybody loves them.
Aaron Francis
00:40:25 – 00:40:38
But, two, you can tell it's like, oh, Ben Ben's back. This is fun. And it seems it seems like that has happened in the past two months maybe. So Yes. Tell tell us the rebirth of Ben.
Aaron Francis
00:40:38 – 00:40:40
You moved to New York City, and what happened?
Ben Orenstein
00:40:43 – 00:40:47
What happened? So yeah. So I I'm here. So it's I've been here for twenty days.
Aaron Francis
00:40:47 – 00:40:47
K.
Ben Orenstein
00:40:47 – 00:41:02
And so I said, okay. I'm I'm initially gonna do, like, a scouting mission. I'm gonna go there for three weeks and see how it feels. And so I'm staying in a friend's apartment while he's traveling, And it's been awesome. Like, I started just having, like, lots of coffees with founders Mhmm.
Ben Orenstein
00:41:02 – 00:41:16
And being like, oh, yeah. I know some stuff. Mhmm. Like, the thing that I that first Twitter video that I recorded, which has still been the best one to date, like, hundreds of thousands of views at this point, I think. And it's still I still see it bouncing around, like, and you still get the notifications from it.
Ben Orenstein
00:41:16 – 00:41:16
Like Is
Aaron Francis
00:41:16 – 00:41:17
that the pricing one?
Ben Orenstein
00:41:18 – 00:41:27
Yeah. Like, a new company shouldn't have a pricing page, shouldn't have a on like, you should manually onboard people that that thing. Thanks. That was something I told a founder that I had coffee with. Yep.
Ben Orenstein
00:41:28 – 00:41:37
And he was like, this is really useful. And he talked to his cofounder, and he's like then he told me a couple days later. He's like, because of that conversation, we are dramatically changing our strategy. Love it. And I was like, oh.
Aaron Francis
00:41:37 – 00:41:39
God. It's gotta feel good.
Ben Orenstein
00:41:39 – 00:41:45
Yeah. I learned some things. Yeah. I know some stuff. And hopefully, that is turns out to be the right strategy for them.
Ben Orenstein
00:41:46 – 00:41:59
But I'm pretty sure I learned some stuff. And, like, people and I'm having coffee with people, and they are, like, seeming to value the feedback I'm giving them. And so I recorded that video because, like, he responded so positively to that idea. But I was like, oh, I should, like, publish this out. And I was like, I should write a blog post.
Ben Orenstein
00:42:00 – 00:42:16
That sounds annoying. Let me just record a video where I talk about it real fast. And that that blew up and did really well. And so, yes, I feel like I am sort of rediscovering things I love, which is, like, teaching the things that I have learned. I'm also being, like, aggressively in person.
Ben Orenstein
00:42:16 – 00:42:16
Yeah.
Aaron Francis
00:42:16 – 00:42:20
I was I was gonna say having coffee with founders is different than having Zoom with founders.
Ben Orenstein
00:42:21 – 00:42:31
So different. Yep. And so, like, I'm, like, declining Zooms and remote things. Like, you're you're you're one of the few people I'm talking to remotely, because I'm like, no. No.
Ben Orenstein
00:42:31 – 00:42:48
Like, come meet me here. Otherwise, I don't know how to do it, with some exceptions. But I also feel like I'm kind of coming back online Mhmm. In a way that has surprised me where I I'm like, oh, wow. I sort of didn't notice what a funk I was in until the funk started lifting.
Ben Orenstein
00:42:48 – 00:42:53
Mhmm. And I'm like, oh, right. There's my excitement. I'm actually usually really excited. Mhmm.
Ben Orenstein
00:42:53 – 00:43:13
And, like, I'm very good at getting excited about the future. And I haven't felt that for a little bit, but it's coming back now. And I actually feel like I have swung past even my old highs, and I'm now kind of, like, actually feeling really optimistic. I've sort of found my people here in New York. And so I'm I'm coming to the end of the sort of initial scouting mission.
Ben Orenstein
00:43:13 – 00:43:19
I've already booked another six weeks, in a coliving community here, which is, like, the most social A
Aaron Francis
00:43:19 – 00:43:24
coliving community. What it what it I mean, I can intuit, but tell me, what does that mean?
Ben Orenstein
00:43:25 – 00:43:30
It is a group of people that are sort of, like, loosely affiliated
Aaron Francis
00:43:30 – 00:43:30
Okay.
Ben Orenstein
00:43:30 – 00:43:33
Who live near each other and wanna do life together.
Aaron Francis
00:43:33 – 00:43:34
Amazing.
Ben Orenstein
00:43:34 – 00:43:38
So there's this, like the sort of center of this is, like, these loft apartments.
Aaron Francis
00:43:38 – 00:43:38
K.
Ben Orenstein
00:43:39 – 00:43:54
And, there's I think that at this point, the the community has rented something to, like, 12 of them. Wow. And there's, like, sort of, like, a a shared co, community space that has lots of events and people hanging out. And, it's a lot of people. There's actually a number of people in my position.
Ben Orenstein
00:43:54 – 00:43:57
There's, like, a it's, like, a lot of software engineers, a lot of whom are between things.
Aaron Francis
00:43:58 – 00:43:58
Amazing.
Ben Orenstein
00:43:58 – 00:44:13
Whether yeah. They're kinda like, oh, yeah. Like, I just left my company, and I'm not sure what I'm gonna do. So I was here because everyone here seems really cool and likes to build stuff and is optimistic about the future and our ability to shape it. And I've met some, like, really incredible people, and I'm just like, oh, yeah.
Ben Orenstein
00:44:13 – 00:44:24
This is this is what I want. This is the opposite of working remotely from home by myself. And it feels like super right. And so I'm gonna start with six weeks, starting in April.
Aaron Francis
00:44:24 – 00:44:52
This is the dream. Like, I I don't know about everybody else, but this is my dream. Maybe well, actually, definitely not in New York City, but to have all of my friends, like, in the same little block neighborhood, whatever, and we can all just kinda, like, dork around and walk over to each other's houses, and that is that is the platonic ideal. And I didn't know that, like, co living communities existed. And so it sounds like you have found that.
Ben Orenstein
00:44:52 – 00:44:56
Yes. Yeah. I really have. It's called Fractal, by the way.
Aaron Francis
00:44:56 – 00:44:56
Okay.
Ben Orenstein
00:44:56 – 00:45:02
It's fractalnyc.org or com or something. But Fractal NYC will get you the the site and you can sorta see some more about it.
Aaron Francis
00:45:02 – 00:45:04
Did you have to apply?
Ben Orenstein
00:45:06 – 00:45:22
No. Okay. I started following one of the founders on Twitter on a whim and DM ed him as part of my, like, oh, I should, like, reach out to people that live in New York that seem interesting. And within five minutes of meeting him and his wife, I was just like, oh, yeah. This is yep.
Ben Orenstein
00:45:22 – 00:45:23
These are my people. I'm in.
Aaron Francis
00:45:23 – 00:45:23
Love it.
Ben Orenstein
00:45:23 – 00:45:31
I'm going I'm I'm I'm all in on this. And the more that more people I've met in this, like, Fractal community, the more I've just been like, oh, god. Yes. I'm still yeah. This is what I want.
Aaron Francis
00:45:31 – 00:45:33
Fractal is a cool name too.
Ben Orenstein
00:45:33 – 00:45:33
Right? I think
Aaron Francis
00:45:33 – 00:45:34
it's really cool.
Ben Orenstein
00:45:35 – 00:45:47
And the the long term ambitions of Fractal are awesome and motivating to me and and great. So I'm like I'm just, like, very stoked. Yeah. So I was already really liking New York before I found this community. And I was like, oh, yeah.
Ben Orenstein
00:45:47 – 00:45:51
The energy is here. I'm enjoying like, every day, I feel a little more conviction. I'm like, okay. This feels right. This feels right.
Ben Orenstein
00:45:51 – 00:46:01
This feels right. And then last week, I just, like, stumbled onto this. And I was like, okay. It's even more right than I thought. Here is, in fact, the center of the right bull's eye.
Ben Orenstein
00:46:02 – 00:46:22
And so I'm feeling, like, really excited. I talked to my mom last night, and she's sad because she wants me to live close to her, of course. And I want that too, eventually. But she, you know, she heard me talk about this for an hour, and she said, well, it's pretty clear there's no talking you out of this.
Aaron Francis
00:46:22 – 00:46:22
Moms know.
Ben Orenstein
00:46:22 – 00:46:23
I'm not even gonna try.
Aaron Francis
00:46:23 – 00:46:25
Moms always know.
Ben Orenstein
00:46:25 – 00:46:36
She's She's like, part of me wants to, but that's it's obvious that's not gonna work. So I I think you gotta do it. I also got something I got to too. So I even got the mom somewhat reluctant stamp of approval.
Aaron Francis
00:46:36 – 00:46:44
That's when when they when mom says, well, I'm not gonna try, that's a pretty big bar because mom's left to try to get you to come home. Oh, yes. Oh,
Ben Orenstein
00:46:44 – 00:46:50
yes. And I think I can do both. I can like, Boston's not that far. I'm gonna go home a lot. I love my family a lot.
Ben Orenstein
00:46:50 – 00:47:00
I like spending a lot of time with them. I intend to do that still. But my heart is telling me, like, you gotta be in New York right now. This is all this all the signs are coming back positive.
Aaron Francis
00:47:00 – 00:47:12
So I'm seeing everyone's seeing the rebirth of Ben coming back. What so it sounds like relationally, you're in your sweet spot. You're getting to hang out with people in person. You're having fun. You're you're enjoying the living.
Aaron Francis
00:47:12 – 00:47:16
What does the working look like? What are you looking for now on the work front?
Ben Orenstein
00:47:17 – 00:47:24
I don't know, and I feel great about that. Great. Yeah. Starting things is probably the answer. Okay.
Ben Orenstein
00:47:24 – 00:47:40
Starting stuff slash helping things that I think are good work. Mhmm. I don't know what the specifics of any of those are going to be. And that feels totally good to me actually right now. Like, maybe never like, I thought the lack of structure was gonna feel terrible.
Aaron Francis
00:47:40 – 00:47:41
Mhmm.
Ben Orenstein
00:47:41 – 00:47:58
But I have that lack of structure plus what feels like a huge fields of opportunity. Yeah. And that actually feels really good where it's like, I like that my calendar is not full of things. I like that I don't quite know what's gonna happen. I'm excited to pour effort and resources into things that seem promising.
Ben Orenstein
00:47:58 – 00:48:08
Mhmm. But I I might never have quite this much freedom again, and I'm really just appreciating, like, that I don't need to rush into knowing the answer to, like, the what is next question.
Aaron Francis
00:48:08 – 00:48:26
Yeah. I love that. And that's a huge I mean, that's a huge turn from earlier in the story when you went on your sabbatical and you were totally lost. Like, this is that's amazing. And that gives you a that gives you a luxury that very few have, which is, like, finding the right next thing instead of just saying, holy crap.
Aaron Francis
00:48:26 – 00:48:27
I gotta get something right now.
Ben Orenstein
00:48:28 – 00:48:49
Absolutely. I feel zero rush on that partly because I want the next things to be, like, really great for me. Yeah. And so I'm intentionally casting a very wide net, or it's like it might look pretty weird to, like, a year ago, Ben, what I end up choosing. But I have a hunch, like, there's some really great things that are completely outside what I would have considered if I'd made a list of, like, what I might do next.
Aaron Francis
00:48:50 – 00:49:00
Yep. You are currently in the explore phase of the explore exploit. And you can go as wide as you want until you find the thing that you can drill down on, which is a nice a nice feeling.
Ben Orenstein
00:49:01 – 00:49:08
Totally. Yep. It feels it feels great. Yeah. The community is great, by the way.
Ben Orenstein
00:49:08 – 00:49:29
If, like, hearing me describe this tickles something in your brain and you're like, oh, I think I wanna be part of that. Like, you should check it out. Like, you should maybe reach out to me or at least read the website and see what see what's there because, the more the merrier of the right people in some sense Mhmm. If you're if you get the right vibe. So I would like more people to show up and join this thing, And I'll be there.
Ben Orenstein
00:49:29 – 00:49:35
We can hang out. We'll be friends. Yeah. And eventual and I don't know. We'll see.
Ben Orenstein
00:49:35 – 00:49:36
We'll see what happens for me.
Aaron Francis
00:49:37 – 00:49:50
Well, I'm excited for you. I'm I'm excited. Yeah. I'm excited to see you try, something new. I think you faithfully executed your role at Tupelo for a very long time, and you should take great pride in that.
Aaron Francis
00:49:50 – 00:49:57
And now I'm excited to see what's next. I mean, I don't know what it's gonna be, but I bet it's gonna be fun.
Ben Orenstein
00:49:58 – 00:50:07
That's actually what I'm optimizing for. Yeah. Like, someone asked me the other day, like, what's your North Star right now? And I was just like, excitement. Just like, how stoked am I about the things I'm doing?
Ben Orenstein
00:50:07 – 00:50:12
Like, when I look at my calendar, when I look at what I'm going to do, like, am I really excited or not? That's, like, I'm, like, follow that.
Aaron Francis
00:50:12 – 00:50:20
A lot worse north stars. And maybe you couldn't choose many better north stars than, like, what am I excited about? Let's let's follow that.
Ben Orenstein
00:50:20 – 00:50:32
And and that's what works for me. Like, I'm not good at working hard on something when I'm not excited about it. But when I am, I'm, like, pretty happy to throw myself into things. Yeah. It doesn't feel like work anymore because I'm excited about it.
Ben Orenstein
00:50:32 – 00:50:52
And there's a point I wanted to make. I wrote a blog post maybe ten years ago at this point on the thought bot blog. And the title is clear your mental cache. And the point was, for a long time, I thought I was a really bad dancer because at one point, someone had I'd kind of gotten the feedback from culture and society. Like, I was not that good at dancing.
Ben Orenstein
00:50:52 – 00:50:57
And so I was like, oh, I'm bad at dancing. I know the answer to this. Am I good at dancing? No. I'm bad at dancing.
Ben Orenstein
00:50:58 – 00:51:11
And then I, like, went to a couple dance classes, and I noticed I was picking it up way faster than the other people in the class. And I was like, that's weird. And someone was like, how many of these have you been to? And I'm like, this is my first one. They're like, this is your first one?
Ben Orenstein
00:51:11 – 00:51:23
And I'm like, yeah. That's weird. And I realized I had this old belief in my cash, which is just like bad at dancing. True. And I needed to clear that because it wasn't true anymore.
Ben Orenstein
00:51:23 – 00:51:42
Like, something changed. And my mental cash also definitely held lack of structure equals scary, sad, lonely, bad. Like, not not having not knowing what my job is is is that thing. And it was based on this, like, scary touch the stove experience. Like, okay.
Ben Orenstein
00:51:42 – 00:51:58
I'm not gonna touch that stove again. And, it was outdated. I needed to be invalidated. And so I am once again reminded that it's really easy to carry around these values and not recompute them because it's expensive and a little scary, but they often get stale.
Aaron Francis
00:51:58 – 00:52:21
They get stale, and, frankly, you just take it as true. You don't ever revisit it. And again, it's one of those things where it's like, it's not that I'm actively holding on to this. It's that I just haven't even thought about going back to the source and seeing if it's actually true. And I feel like that in that in itself is a skill to look at these things that you're taking as givens and being like, hang on.
Aaron Francis
00:52:21 – 00:52:28
Is that still given? Is that still true? Right. And by the way, you gotta make a Twitter video out of this. This is great.
Aaron Francis
00:52:28 – 00:52:33
Mental cash, like, just do it again. You wrote a blog post. Just make a video. This is a great video.
Ben Orenstein
00:52:33 – 00:52:34
Yeah. Yeah. Alright. Alright. I'll do it.
Ben Orenstein
00:52:34 – 00:52:40
I'll add to my list. Good. So see, this is a good this is one reason it's great to have friends.
Aaron Francis
00:52:40 – 00:52:44
Uh-huh. Like, that that hit that hit me. You gotta you gotta tell everyone. Put it on the Twitter, man.
Ben Orenstein
00:52:45 – 00:52:51
Uh-huh. Yep. Exactly. This is right. Especially friends that are used to publishing.
Ben Orenstein
00:52:51 – 00:52:57
Mhmm. And they go, oh, you should you should make this. And I I I give that feedback to someone the other night at dinner. Like, he said something really smart. I'm like, you should you should make this.
Ben Orenstein
00:52:57 – 00:53:07
Write this down. Tell more people this is true and is unique like, sort of a unique insight. You should get it out there. Speaking of friends, speaking of making things and getting them out there.
Aaron Francis
00:53:08 – 00:53:11
Return it. We are returning the turntables again.
Ben Orenstein
00:53:11 – 00:53:13
I think are are you up for it?
Aaron Francis
00:53:13 – 00:53:14
I'm ready. Yeah.
Ben Orenstein
00:53:14 – 00:53:17
Yeah. You ready? Okay. Yeah. So that's a so that's that's what's up that's new with me.
Ben Orenstein
00:53:17 – 00:53:19
What's what's new with me?
Aaron Francis
00:53:19 – 00:53:20
That's a lot. That's a
Ben Orenstein
00:53:20 – 00:53:21
quick summary of what's going
Aaron Francis
00:53:21 – 00:53:22
on with
Ben Orenstein
00:53:22 – 00:53:27
me. Only only took us an hour. Yeah. Is anything going on with you?
Aaron Francis
00:53:27 – 00:53:59
Everything is going on with me. Yeah. I mean, for for people that that don't know, I I got recently laid off from a database company called PlanetScale. It's maybe two weeks ago at this point, and they laid off according to their public blog post most of the sales and marketing teams, and I was on I was on marketing team. I was making lots of database videos and, returned well, actually got laid off right before I returned from paternity leave.
Aaron Francis
00:53:59 – 00:54:09
So then it's just like, well, what do I do now? So things that have changed. Yeah. I lost my job. I have two sets of twins at home.
Aaron Francis
00:54:10 – 00:54:26
The newest ones are four months old, and the the oldest ones are two and a half years old. So we've got four under three. So, yeah, there's there's a lot of change, and I'm trying to figure out, likewise, trying to figure out what's next. And I think I think I'm circling it.
Ben Orenstein
00:54:27 – 00:54:42
It's exciting. So I think so there's there actually does exist a real a nice summary of kind of what has happened to you to date on your podcast, mostly technical, which folks could go listen to. Mhmm. So that if if you want the the all the details, you can go get those.
Aaron Francis
00:54:42 – 00:54:47
Mhmm. There's an episode called The Layoff on mostlytechnical.com, and that'll give you
Ben Orenstein
00:54:47 – 00:54:48
Which sounds like a good that that sounds like a
Aaron Francis
00:54:48 – 00:54:49
drama I
Ben Orenstein
00:54:49 – 00:54:58
know. Title. You know, like, stuff you see on on Netflix, that'll layoff. So if you want all the nitty gritty, I think that's probably good to go listen to that. And it's a good podcast, so you can listen
Aaron Francis
00:54:58 – 00:54:59
to that.
Ben Orenstein
00:54:59 – 00:55:07
No. Thanks. So maybe we talk maybe we focus on kind of your latest answer to Mhmm. So what what do you wanna do given all of these things that just happened?
Aaron Francis
00:55:08 – 00:55:25
Yeah. So it's, it's kind of a new situation for me. Not only like, I've never been laid off before, so that, of course, that is new. But the thing that I am really considering new is publicly searching for a job. Like, publicly saying, I'm out here.
Aaron Francis
00:55:25 – 00:55:35
Who wants to hire me? That has never happened. So, like, when I left the property tax firm, I DM ed you and was like, hey. I saw your hiring. Maybe I'll come there.
Aaron Francis
00:55:35 – 00:55:42
I was like, great. Let's do it. When I left Tuple, it's because somebody reached out to me and was like, hey. Do you wanna come to play in scale? I was like, sure.
Aaron Francis
00:55:42 – 00:55:49
Let's do it. And so now, like, everything has always been kinda like, wow. I have a job. Something else has kinda just like, come out of nowhere. Right?
Aaron Francis
00:55:50 – 00:56:03
Now I'm in this spot where it's like, okay. What does the world have to offer? I've never been free to explore that. And so, you know, the day I got laid off, I put out a tweet that was it just said, like, hey. I got laid off.
Aaron Francis
00:56:03 – 00:56:41
I would love to hear, like, if you guys have any ideas. And while getting laid off, I don't recommend having a lot of people on your team. I super recommend. I think I had not, like I don't think I, speaking of cash, had updated my mental model about how many people, like, genuinely are on my team, not just like, oh, there's a guy that's, like, on Twitter, and I enjoy his content. It was people that were, like, really wanting me specifically to succeed and do well.
Aaron Francis
00:56:41 – 00:56:56
And the just kinda like the the the outpouring of people in DMs and publicly and emails just saying, hey, bud. I like whatever it takes, I got you. I was like, what is going on? It was wild.
Ben Orenstein
00:56:56 – 00:57:05
Your announcement tweet, I mean, had, I think, had 400 replies when I last looked at it. It's probably a lot more than that now. Yeah. Just been like, hey. I got laid off.
Ben Orenstein
00:57:05 – 00:57:15
This kinda sucks. Mhmm. And just, like, hundreds of people Yep. Expressing support. And I see and and also sort of pretty explicitly a lot of job offers.
Aaron Francis
00:57:15 – 00:57:15
Yes.
Ben Orenstein
00:57:16 – 00:57:16
Rightfully.
Aaron Francis
00:57:17 – 00:57:17
Very much so.
Ben Orenstein
00:57:17 – 00:57:25
Yeah. I think I feel like yes. I think you probably it's I think it's hard to update your cash on this thing in particular. Like, your own standing
Aaron Francis
00:57:25 – 00:57:26
Yes.
Ben Orenstein
00:57:26 – 00:57:49
Is sort of hard to, like, really appreciate. And I think you have been, like, authentically very kind and helpful on the Internet for a long time in a in a in a pretty massive way. And I'm actually kind of I'm actually really glad you got that experience of sort of not cashing it in, but sort of experiencing, like, feeling more viscerally
Aaron Francis
00:57:49 – 00:57:50
Mhmm.
Ben Orenstein
00:57:50 – 00:57:56
The positive things that you have done in the world coming back to you in response as, like, thanks for what you've done.
Aaron Francis
00:57:56 – 00:58:19
Yeah. That is, that's a pretty unique and moving thing, I think, that happened. It feels it feels like one of those, like, this is somewhat morbid, but it almost feels like a eulogy that I'm getting to listen to. And everybody's, like, saying these really nice things, and I'm here to, like, receive that and feel that. It's like, man
Ben Orenstein
00:58:19 – 00:58:19
Yeah.
Aaron Francis
00:58:19 – 00:58:40
I just don't know that this happens very often. What a, like, what a joy for me. So, yeah, I don't recommend getting laid off, but, honestly, like, I'm feeling pretty great. And that's just because there there's really there's so much opportunity, and there's so many people that are on my team that how could I, like, how could I not? You know?
Ben Orenstein
00:58:40 – 00:58:45
Yeah. You're gonna be fine. Thanks. More more than fine, I think.
Aaron Francis
00:58:45 – 00:59:10
So I took, you know, I took last week to just interview or talk to, everyone that I possibly could because, like I said, this is all new for me, and I wanna see what's out there. And even in these even in these calls, I'm just people are like, hey. I I know who you are. And I'm like, really? Like, this is this is new to me.
Aaron Francis
00:59:10 – 00:59:16
And so they're like, I know who you are. Your work is great. Do you wanna come work here? I'm just like, this is wild. And
Ben Orenstein
00:59:17 – 00:59:19
Right. No resume. No. No application.
Aaron Francis
00:59:20 – 00:59:20
No. Nothing.
Ben Orenstein
00:59:21 – 00:59:28
This is the beauty of putting enough work out in the world Mhmm. Is that it becomes this is how this is what job seeking looks like.
Aaron Francis
00:59:28 – 00:59:39
Yes. It becomes, like, self evident that you can do the job that this person is trying to hire you for. I don't have to try to convince them. They're saying, I've watched you do the job. Like, we don't need to talk about that.
Aaron Francis
00:59:39 – 00:59:42
I've seen you do it. Let's talk about something else.
Ben Orenstein
00:59:42 – 00:59:43
Mhmm.
Aaron Francis
00:59:43 – 01:00:17
And so I, you know, I talked to all of these companies and some really great companies with lots of kind people, who were very encouraging. But the overwhelming feeling that I kept having was, I wonder if this is my moment to to give it an honest go. Like, I've been, you know, I've been trying hard at stuff for a really long time, but in some sense, it's always been hedged because I've thought, you know, it's a side project or, like, I have a, you know, I have a real job. And so if this thing fails, like, yeah, that's alright. That's okay.
Aaron Francis
01:00:19 – 01:00:42
And now I'm thinking, like, what's it look like to to, like, not have a hedge? What's it look like to go super hard and to call this thing a a business instead of, like, a a side project, which I feel like is hedging in the first place. And so, you know, it hasn't been announced. It's weird. We're we're in the past, been speaking to the future, but when you listen, this will be in the past.
Aaron Francis
01:00:43 – 01:01:01
Tomorrow. So tomorrow, on Friday, my friend Steve and I are announcing that we're we're going out together. And so Steve is the guy who helped me at PlanetScale with all the videos. He's like a proper he's a proper, like, filmmaker, videographer. He's done the whole thing.
Aaron Francis
01:01:01 – 01:01:32
And so we're gonna go out together, and we're gonna start, we're gonna start a a video studio. And so the the the plan is we'll have, like, two prongs of of offerings. One will be in house stuff. So I'll teach some courses on, you know, Laravel and databases, and we'll build up this offering of, like, the best educational material on databases that exists in the world, and we'll just sell that straight up. And then the other prong is going to be consulting, and we'll say, listen.
Aaron Francis
01:01:32 – 01:01:58
You're spending millions of dollars on salaries for your Dev Ed, DevRel, Dev Advocacy team, and they're making videos that get 40 views on YouTube. Like, hire us. We can come in, and we can make those people 10 x as effective for very little cost considering. And then for a select few companies that wanna pay us, we'll do the whole deal. I'll be the on camera talent.
Aaron Francis
01:01:58 – 01:02:12
I'll do the course. Steve will do the production and the editing and the graphics and all that, and that's like the contact us for pricing kinda deal. Like, oh, you want us to you want me to be the face of your company for this course? I would love to have a conversation about that.
Ben Orenstein
01:02:13 – 01:02:18
Yes. I hope you name a number for that that makes you laugh out loud slightly.
Aaron Francis
01:02:19 – 01:02:31
The the the number, I won't say it here, but the number that we've named so far has made me just laugh hysterically. And Steve was like, oh, no. I think we could go higher. So I'm like, thank you, Steve. I I need you in my life.
Ben Orenstein
01:02:31 – 01:02:36
Yeah. Yes. I I would like to see this number before you send it to anybody just in case there's more room.
Aaron Francis
01:02:36 – 01:02:38
Yes. For sure.
Ben Orenstein
01:02:39 – 01:02:53
This is very exciting. I we chatted about this Mhmm. A bit, and I was encouraging you to, like, not go take a job and to sort of do some thing along these lines. And so you're I'm I'm very pleased to see you going this direction.
Aaron Francis
01:02:53 – 01:03:13
Thanks. I'm I'm very excited, and I think the the big thing that I think is, like, once we get in the game, we can we can basically figure out anything. Like, this is the this idea currently is that it's worst state possible. Yeah. And it will get better once we talk to people and they're like, actually, we need this thing.
Aaron Francis
01:03:13 – 01:03:24
Like, great. We can actually do that thing. Let's change our offering. So the thing that I want to avoid is riding my personal opportunity over the top. Right?
Aaron Francis
01:03:24 – 01:03:34
I don't wanna I don't wanna miss the window. I don't wanna ride the hype over the top. I want to say, now is the moment. I gotta get in the game, and we'll we'll just we'll freaking figure it out as we go.
Ben Orenstein
01:03:34 – 01:03:40
Yep. Yeah. I like that a lot. And, you know, there's a lot of power in, like, doing the thing for real full time. You know?
Ben Orenstein
01:03:40 – 01:03:58
No backup exactly. Just like and you've got the backup. You know, you you know you have a job waiting for you if you decide that that's the right path. So, like, all the more reason to, like, do something with a better possible return that's hopefully gonna be more fulfilling and fascinating and challenging. And, yeah, I'm I'm excited.
Ben Orenstein
01:03:58 – 01:04:05
I do still I I do still really wanna see the Aaron Francis product Mhmm. That you sell to the the Aaron Francis audience.
Aaron Francis
01:04:05 – 01:04:06
I know.
Ben Orenstein
01:04:06 – 01:04:11
I I do still think there's an interesting business in there somewhere that maybe isn't is is something other than a course.
Aaron Francis
01:04:11 – 01:04:12
Mhmm.
Ben Orenstein
01:04:12 – 01:04:21
But we we couldn't figure it out on our on our first phone call. So I I don't so I don't have the answer to that, but I think someday that's probably I see that in your future most likely.
Aaron Francis
01:04:21 – 01:04:36
Yeah. I think so too. And and something that has been continually, told to me by you and Daniel Zarek and Jordan Gall, all these people is like, dude, think bigger. Like, push push push. Think bigger think bigger.
Aaron Francis
01:04:36 – 01:05:01
And that has been incredibly helpful to me because, you know, I don't know if it's, just how I'm wired or, you know, religious background, religious foreground, I'm still religious, but just like thinking lowly of myself almost and thinking like, okay. I I shouldn't I shouldn't strive for, greatness. And it's like, no, dude. You've got the thing. Push harder.
Aaron Francis
01:05:01 – 01:05:12
I'm like, oh, that's helpful. Yes. So that's been that's been a really wonderful outcome of talking to, you know, these these friends that I can talk to, and they can say, Aaron, you gotta dream bigger, man.
Ben Orenstein
01:05:12 – 01:05:19
That is, I think, one of the hardest caches to clear. Yes. It's the how much should I expect from life?
Aaron Francis
01:05:19 – 01:05:19
Exactly.
Ben Orenstein
01:05:20 – 01:05:22
How much am I truly capable of?
Aaron Francis
01:05:22 – 01:05:25
Yep. Turns out the answer is more. More.
Ben Orenstein
01:05:26 – 01:05:39
I think the answer is more. Yeah. And I'm glad I can help be one of the one of the voices nudging you in that direction. Because from the outside, the beauty of the of the thing outside the cache is it's very easy to see. It's not a question like, oh, Code Aron, do you know more?
Ben Orenstein
01:05:39 – 01:05:42
I don't know. No. He probably should just get a job. No. That is Yeah.
Ben Orenstein
01:05:42 – 01:05:49
No. Yeah. Not a thing. There's not that many people that have the juice, and you got the juice.
Aaron Francis
01:05:49 – 01:05:57
No. Thanks. Yeah. I I think I'm starting to realize that, frankly. I think I'm starting to, like Good.
Aaron Francis
01:05:58 – 01:06:15
Believe that. I've seen individual pieces of work, that I've done do very well, but I think I'm starting to believe, like, there's something that is different or, like, something that I am good at that that is making this happen. And so I'm trying to, like, lean into that.
Ben Orenstein
01:06:16 – 01:06:24
Yes. Yeah. It's you are the function producing these things, and the function is good. It's not just like the you got lucky a couple times. Yep.
Ben Orenstein
01:06:25 – 01:06:29
Yeah. It's no. It's it's the it's the meta. It's the higher has the higher order function
Aaron Francis
01:06:29 – 01:06:29
Yeah.
Ben Orenstein
01:06:29 – 01:06:30
That's doing this.
Aaron Francis
01:06:30 – 01:06:42
Yeah. Thanks. So it'll be, you know, optimizing for excitement and fun. I'm right there with you. This is the most this is the most exciting possibility and this is the most entertaining.
Aaron Francis
01:06:42 – 01:06:49
Like, if if we're just doing it for the lost, this is definitely the most entertaining option possible. And that's exciting.
Ben Orenstein
01:06:49 – 01:06:54
That's awesome. I'm so glad to hear that. Because you know you can go optimize for safety, reliability
Aaron Francis
01:06:54 – 01:06:54
For sure.
Ben Orenstein
01:06:54 – 01:06:56
Stable paycheck. You know you can do that.
Aaron Francis
01:06:56 – 01:06:57
Mhmm.
Ben Orenstein
01:06:57 – 01:07:00
And so given that you have that fallback, your family will be okay.
Aaron Francis
01:07:00 – 01:07:01
Mhmm.
Ben Orenstein
01:07:02 – 01:07:08
Why not try to optimize for the excitement? And and the growth. Yes. Like, this will be harder too.
Aaron Francis
01:07:08 – 01:07:08
It will be.
Ben Orenstein
01:07:08 – 01:07:15
This will be more challenging. It'll probably be more variance, but I do think it makes life so much richer.
Aaron Francis
01:07:15 – 01:07:24
Yep. Yeah. I could have easily gone and phoned it in somewhere and not have been happy at in three months or six months.
Ben Orenstein
01:07:25 – 01:07:25
Exactly. Yeah.
Aaron Francis
01:07:25 – 01:07:39
And it's just the story. Man, the story is too good. I'm It's too good. I'm the I'm at no fault here. I'm the aggrieved party, and so I I did an amazing job at PlanetScale, and then my separation was 100% not my fault.
Aaron Francis
01:07:39 – 01:07:46
And so there's no, like, there's no, like, oh, I can't believe Aaron left PlanetScale high and dry. No, I didn't. That's not I didn't
Ben Orenstein
01:07:46 – 01:07:47
do that.
Aaron Francis
01:07:47 – 01:07:54
And so now it's like, okay, wow, he's laid off. What's gonna happen next? It's like, this is a great story. We gotta we gotta write it. So
Ben Orenstein
01:07:54 – 01:07:57
Yeah. Right. Exactly. Don't waste a great setup.
Aaron Francis
01:07:57 – 01:08:06
No. What a what a mistake that would be to be like, oh, I had this moment, and then I went and worked at a database company that you haven't heard of. It's like, oh, again?
Ben Orenstein
01:08:06 – 01:08:10
Yeah. You're doing that again? Yeah. I guess. I mean, you do have four kids.
Ben Orenstein
01:08:10 – 01:08:10
I suppose.
Aaron Francis
01:08:10 – 01:08:12
Yeah. Seriously. Yeah.
Ben Orenstein
01:08:12 – 01:08:17
I mean, you're gonna die someday, and you're wasting your life there. But whatever, that's fine. I suppose. Some people are cool
Aaron Francis
01:08:17 – 01:08:22
with that. But at least you can go on your one vacation a year. Like, no. I'm doing it. I'm going big.
Ben Orenstein
01:08:22 – 01:08:23
So Do the thing.
Aaron Francis
01:08:23 – 01:08:28
That's that's where I'm at. And I feel very excited about it. Terrified, of course, but but very excited.
Ben Orenstein
01:08:28 – 01:08:35
I mean, that's right, basically. That's my this is my new philosophy. It's like, yeah. Your your gut will tell you when you are doing the right things or the wrong things.
Aaron Francis
01:08:35 – 01:08:52
Man, and there was something something it was probably just a tweet or I don't know what it was, but there was something I read once that was, like, if you wanna, like, if you wanna do something really big but you're scared, do it scared. Like, don't don't let it stop you. Do it. Mhmm. Do it scared.
Aaron Francis
01:08:52 – 01:08:55
That's fine. And that's kinda how I feel. I'm like, yeah.
Ben Orenstein
01:08:55 – 01:08:56
This is awesome.
Aaron Francis
01:08:56 – 01:08:57
I'm terrified, but this is awesome.
Ben Orenstein
01:08:58 – 01:09:03
Feel the fear and do it anyway. Yep. Totally fine. In fact, probably a very positive sign.
Aaron Francis
01:09:03 – 01:09:04
Yeah. I think so.
Ben Orenstein
01:09:04 – 01:09:07
If there's no fear, you're go go bigger.
Aaron Francis
01:09:07 – 01:09:12
Yeah. Exactly. Yeah. And there would be, like, god. There's just no fear in taking a job.
Aaron Francis
01:09:12 – 01:09:34
I'm just like, whatever. I don't care. So I feel like this is the right decision. It'll be interesting to see in the next month or two or three what the discrete offerings shake out to be, because we've gotten a ton of interest even in these interview rounds, Steve and I both, of companies that are like, hey. If you go solo, we wanna be your first client.
Ben Orenstein
01:09:34 – 01:09:34
And I'm
Aaron Francis
01:09:34 – 01:09:39
like, really? Like, four, five four, five companies have said that. And so
Ben Orenstein
01:09:40 – 01:09:42
Wow. Sounds like they need to bid against each other.
Aaron Francis
01:09:42 – 01:09:55
Yeah. It sounds like it. So I'm I'm excited to see what that, like, what that forms up into and what our, you know, h one ends up saying. But we'll, you know, we'll dance around it for a little while.
Ben Orenstein
01:09:56 – 01:10:05
Right. Feels very, like, feels very clear this opportunity here. Mhmm. What the exact until, like, as you explore this and figure out what the exact offerings are. Yeah.
Ben Orenstein
01:10:05 – 01:10:07
That that's gonna be a good process, I think.
Aaron Francis
01:10:07 – 01:10:23
Yeah. Our current our current h one is going to be, we make videos that developers want to watch. And that's, like, that's good enough, but it's also vague enough that's, like, do we actually make them? Do you make them and we help? But, like, regardless, developers wanna watch these videos.
Ben Orenstein
01:10:23 – 01:10:26
Hell, yeah. Yep. That sounds good, man.
Aaron Francis
01:10:26 – 01:10:30
Yeah. Thanks. Stay tuned stay tuned for more. We'll see.
Ben Orenstein
01:10:31 – 01:10:38
Yeah. Stay tuned for both of us. It's fun that we're both in this at this, like, sort of, yeah, turning point at the same time. Uh-huh. It's nice.
Ben Orenstein
01:10:38 – 01:10:40
You were the perfect person to bring on to talk about it.
Aaron Francis
01:10:40 – 01:10:47
Well, I'm I'm glad I'm glad you reached out. It's fun to it's fun to take over your role and be the interviewer there for a while.
Ben Orenstein
01:10:48 – 01:10:50
Yeah. You're good at it. You should do this professionally.
Aaron Francis
01:10:50 – 01:10:51
Oh, thanks.
Ben Orenstein
01:10:53 – 01:10:56
Alright, man. It's lovely to talk to you as always.
Aaron Francis
01:10:56 – 01:10:58
Yeah. Thanks for having me on.
Ben Orenstein
01:10:58 – 01:11:11
Yeah. Thanks for asking good questions and being a good listener and and a sounding board and also being somebody I can text that gives great advice and is just warm and helpful and kind, and you deserve this outpouring of love that you got.
Aaron Francis
01:11:11 – 01:11:16
No. Thank you. I I am lucky to count you as a friend. So this is a joy. I appreciate it.
Ben Orenstein
01:11:16 – 01:11:20
Thanks, man. Alright. Bye bye. Bye.
Me

Thanks for reading! My name is Aaron and I write, make videos, and generally try really hard.

If you ever have any questions or want to chat, I'm always on Twitter.

You can find me on YouTube on my personal channel or the Try Hard Studios channel.

If you love podcasts, I got you covered. You can listen to me on Mostly Technical.