Newborns, standup comedy and a new definition of fatherhood | Will Rocklin (new father of 1, Google, Square, Safara)

Will: These role models, like an evolved man, someone who can be angry but not vicious or cry, but not embarrassed, right? There's all these like things that we don't really get a lot demonstrations of, and we have actually so many anti examples.

 It can be confusing and everyone can feel lost. So I spent a lot of time thinking about how to create this for myself, how to demonstrate this for my son, and how to learn.

Adam-IntroOutro: Welcome to Startup Dad, the podcast where we dive deep into the lives of dads who are also leaders in the world of startups and business. I'm your host, Adam Fishman. And in this episode, I sat down with product leader and a budding stand up comic, Will Rocklin. Will is a former Google and Square product manager and was the head of product at Sephora, a Sequoia backed seed stage travel startup. He is currently a fractional PM focused on helping climate tech startups go from zero to one. Most of the time, Will is spending his days as a new father and a loving husband.

In his spare time, Will is a comedian who's performed all over New York and Los Angeles. He wants you to know that with his young son and wife, he is currently gentrifying Los Angeles. In this episode, Will talks about his process of IVF with his wife Amy and what it's like having a newborn. We discuss how marriage is a growth driver for self actualization and why it's time for men to cast aside their father's model of parenting and embrace a new definition of what it means to be a husband and father.

He acknowledges the time consuming nature of parenting and how it has made him re-evaluate his priorities and time management. Will's reflections offer a candid, nuanced view of the joys, anxieties, and adjustments that come with modern fatherhood. I hope you enjoy it as much as I did recording it.

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Adam: Welcome Will Rocklin to the Startup Dad podcast. Will, how are you? And thank you for being here.

Will: I am doing great. Thank you so much for having me, Adam.

Adam: Awesome. I am super excited to record this show. And I wanted to start by just asking you a bit more about your background. So tell us a little bit about your professional background, first and foremost, and then we'll get into the other more interesting aspects of your background.

Will: Sure. So I've been a product manager for about 10 years now, which is what happened. I started this journey at YouTube working on some of the monetization features. Happy to say the ads that you can skip on YouTube, and then went over to Square, worked on the point of sale application, which at the time was called Register and was at Square for about four years.

So I did everything except for that tip screen that you may be kind of tired of that. That was already there by the time I got there. So sorry about that tip screen. That's everywhere now. And then the last six years I've been doing a lot of startup stuff, a lot of zero to one, sometimes full-time, sometimes fractionally for generally non-technical founders and a pre-seed or seed stage.

And doing that across verticals, across B two b B two C enterprise. And that's been a real fun journey. So a mix of everything.

Adam: Awesome, I am glad that we don't have to bring out the torches and pitchforks about the square tipping screen because that has been all over Twitter lately. People saying things like, “it starts at 25%. Now, who's giving a 40% tip?” Like, I have definitely observed that and, yeah, I don't know.

I guess inflation who knows,

Will: I will add that the vendor can set those percentages. That's not a square dictated

Adam: got it. As a product manager, always good to blame the customer. Always a good thing. Okay, so that's your professional background. You've been doing that stuff for about 10 years. You've worked at some very cool companies. So tell me a little bit about you, not professional Will.

What was life like growing up? Where are you from originally? What was your family like?

Will: Yeah, I'm from Connecticut. I'm from a small suburb near New Haven. Most people think of Connecticut as a country club state, and that's not really the experience that I had. I'm kind of from a, like a less refined part of the state. But I had a really wonderful childhood. I had a really wonderful family and still thankfully have a whole of 'em.

It's two older brothers and my parents, they're all still back in Connecticut. I'm the official black sheep of the family living in Los Angeles doing other things. But I will add that I also know how to play tennis and sail, because that's part of the part of it. Yeah. They don't let you leave unless you know how to do that.

So, had a great time. Enjoyed being in a kind of a boring place, but was very ready to leave and have a lot of wanderlust and so a big journey since then.

Adam: Okay. What did your parents do for a living when you were growing up?

Will: My mom was, for most of my childhood, a stay at home mom, and my father was a cardiologist and he still teaches at Yale cardiology. So, yeah,

Adam: Cool. That sounds like a pretty classically Connecticut, you know, upbringing. Now you have some other interesting things about your background. You got into doing standup comedy not that long ago. How did that come about? What do your parents think about you being a standup comic? And more importantly, and we'll get to this in a little bit, what does your partner think about this?

Will: So there was a point where I… I failed building a startup, and I kind of decided to have a midlife crisis a little early maybe. And instead of getting the classic Corvette, I decided to go try standup, which always been a huge passion of mine. Always something that I love, that my family loved just comedy in general.

So there was always something about it that I was drawn to, and I think part of it is, That when you see a really great comic, there's a sense of like, truth, maybe not empirically like universally, but at least their corner of it flowing through them in a way that I found to be something to go chase, something to go try to do and be able to do.

Of course I have a ton of respect for the techniques and the grit and the grind that it takes to get there. And there was a point where I just said, you know, what am I doing? Like what? Like why not? I've got all these advantages that have been given to me and thank goodness for all of them.

I'm super grateful for all of it, but let me at least try to put some chips into the middle of the table and see what can happen here. So yeah, about it's 2023, so about four years ago I decided to just give it a go and it's been a very beautiful experience because it's very hard to lie to yourself and lie to others.

While trying to be funny, people can smell fraud, fraudulent behavior, you know, nonsense before you walk in the door. So, it's been like actually in some ways a spiritual practice that may sound a little bit like a reach, but that's how I've been thinking about it. And it's been a really like wonderful way to get in touch with what's actually true for me and what do I want to say?

What do I stand for? Who am I, how do I seem to others? And standup's just a very efficient, if humbling way, to go through that. I've also been able to, in that process, like perform at a lot of comedy clubs, make a lot of friends doing comedy. I've made some videos and done screenwriting as well.

So it's been it's been a wonderful, beautiful challenge. My wife is actually largely a catalyst for this. So a lot of this really is her fault. Frankly. I think that she's an executive coach, and so I think everyone's partner is in a sense a coach kind of implicitly, but for her also explicitly.

And so she saw me and she's like, “hey I think you have this in you and you want to go see what's here, why not?” And there are legitimate reasons for why not by the way, but I said, yes, let's plow through, let's go through this. And it's been really gratifying. I don't know what's gonna happen with it.

And I just had a kid, you know, we'll get into that. He's six weeks old. Kids - slightly time consuming. Maybe you know this…

Adam: I've heard. Yeah.

Will: So having a pm responsibility and these other components, we'll see. We'll see what, how this all shakes out. But yeah, so far it's been great.

Adam: Yeah. It turns out also, most standup happens at night when kids are waking up and terrorizing the other parents. So, probably good for you to be around for a bit. I would imagine

Will: I think that's probably true. Yeah.

Adam: Well, I've seen your standup. It is really funny you sent me some of the clips. It's on YouTube, I think people can search Will Rocklin Standup and it's there and there were some families, there's some parenting stuff in there.

It was great. I loved it, so kudos to you for taking that leap. It's funny because there's a bunch of, I feel like a bunch of former tech people, and now you're a current tech person, but some former tech people who have made the pivot into doing comedy. Either the pandemic was a catalyst for that or you know, just something else, wanderlust like you mentioned.

But you're in good company, right, with folks like Sarah Cooper and and people like that. So, what do your parents think about you as a standup comic? Are they excited or are they sort of like, don't quit your day job?

Will: Excited would be an odd choice to describe their behavior. Uh, Initially, very anti, I would say, somewhere between very and extremely anti. And over time, they would slip up though in this sort of response to me. I remember my mom saying like, I always wondered when you would do something like this.

And I was just blown away by this response that kind of seeped in like this piece of truth. And then over time they saw me doing it and they saw that it mattered to me and that it was a way of being expressive, which I think is a feeling that a lot of people share. Or it doesn't have to be in standup.

It doesn't have to be in screenwriting. You wanna like get what is in you out. And not just in necessarily in a business sense, but in an artistic or creative capacity business. It can be that outlet, but not just that outlet. They saw that I had that and that it was genuine, it was valuable and making me happy.

And as I said to them, I'm not really hurting anybody, so I'm not really sure what the, the problem is here. And over time they, they started to warm up to it. They have been rooting for me. I'm trying to kind of make my mom be my tour manager. She has not really signed up for that. She hasn't really jumped at that bit there, although I do know and have comic friends whose moms have been their first tour manager to good effect.

So, yeah, no, there's a lot of us in tech current and past who, you know, the skill sets of having real job, a demanding job, actually are very helpful when you step into the entertainment realm because you're competing against a lot of people who don't possess those things, who don't understand that stuff.

And there's a point where you get funny enough, and then after that it's like, can you draw people into your content? Can you draw 'em into your world? So now we're kind of talking about. Acquisition, growth strategy. Also just plain being reliable, being polite, professional. Those kinds of things are not given when you leave the tech world.

Adam: Wow. Have you found that being in standup and doing that has helped you with PM skills like storytelling and, I don't know, presenting or just sort of being able to deliver your message more concisely? I mean, I don't know how often you've had to get up and give a tight five in a product review, but I saw your type five on YouTube, so, yeah.

Just curious if that's been a thing that you found helping you.

Will: Yeah. You know the thing that is interesting about writing a screenplay in particular is that your characters could go in any direction that could take this turn or that turn or go upside down and leave the universe. Really, anything is available to you, which means when you go to write a P R D and it's a password recovery flow, it actually feels extremely simple because there's only so many options your character is going to take.

So, it actually gave me a lot of context there on just decisioning and how to make a choice. It brought me a lot more empathy for users and sort of understanding what may be compelling them or motivating them, but also the demands on their time. Like we are in such a wild place where we're not just competing against, from a tech point of view, like other products, but just anything else people can do with their time.

So if you are going to say something and try to get your message out there, if you're a startup founder, well you're, sort of also competing with James Cameron, you're also kind of competing with Steven Spielberg. So let's be more honest with the scope that's here. The other piece I would add is in terms of just presenting and it's easy to get nervous no matter what stage you step on.

And I would be lying to you if I didn't tell you that. I still get nervous. I was a little nervous before this podcast. And Adam, you're great. This, I'm home. This is very chill.

Adam: That's the vibe we're going for here. Chill vibes on the dad pod.

Will: Yeah, and it's still there. It's still real, but when you do stand up you're in the lion's dead, right? You're trying to elicit a very specific response and own the room and try to make that happen.

So that's the bleeding edge. So when you back away from that and you're in a boardroom kind of setting, it gets easier for sure.

Adam: I feel like I could ask you about a hundred more questions about standup, but maybe someday I'll interview you for my newsletter on the parallels between experimenting as a product manager and experimenting as a comic, which I understand is a big part of the job. Writing jokes, testing jokes, things like that.

But we're here to talk about being a dad. So that's what I want to talk about now. You have a partner, clearly, because there is a six week old baby, and you mentioned her earlier on the, program as an executive coach. So you have one kid, six weeks old, and a partner who's an executive coach.

How did the two of you meet? How did you meet your partner?

Will: I met my wife Amy in the Italian Alps. We were both on vacation and I had just decided to leave San Francisco and quit my job and move outta my apartment. And I went to Burning Man. I don't like to paint myself as a burner, but I went to Burning Man, not for the first time or the last, and then went to Europe for a while, wanted to be alone.

I really wanted to go to the Dolomites. And my wife happened to be there. I was basically moving back to New York. I was on my way back and with the express goal of meeting a wife, that was the purpose I could feel. She wasn't in San Francisco. And we met in the hotel's spa. This is a small bed and breakfast in a sound of music kind of looking town.

Adam: Wow.

Will: And it's kind of a ski town, but this is the summer. And so they all have these big spas in the base of these facilities. And I met her wearing a towel. And I had just seen middle-aged German couples for the last several days. And, She was the first single woman I had seen. I wasn't sure if she was married, if her husband was somewhere else or whatever.

And I did, my wife's Chinese, I did not know if she spoke English. So there was a lot of what's going on here. I also was very worried about being creepy and not coming across as that… so handled with care… but it was pretty wild. We got to talking and turns out we knew a couple people in common.

We had lived very close to each other in a couple different cities. We were pretty sure maybe we'd even been to the same party and just not met. She almost went on a date with one of my very close friends. So we had both worked at Google. There was a lot of commonalities and then I asked her out for a date night that night.

And the rest is history.

Adam: Awesome. That is an amazing story. I was not expecting that story when I asked you. I was expecting something much more vanilla, but I love that also what could possibly be creepier than a guy in a towel, sort of like sidling up to you to get to know you in a spa - that full on creeping mode.

So I, I get it. I know how delicate of a balance that must have been for you.

Will: You've got a mustache. You understand what I'm talking about.

Adam: I do!

Will: So

Adam: I do!

Will: you've gotta be careful.

Adam: You really do, you have to watch yourself in all these situations. And so your son is six weeks old. One of the first things that I'm curious about is the process that you went through to pick his name.

So, as I recall, his name is Orion, like the constellation. Was that hard? How did that all go down and who had the final say in the name picking battle?

Will: Yes. This was hard. My wife and I wanted something different, but not like, “oh my God, this is ridiculous. Who are these people?” I was trying to stay… I don't want to like, you know, be judgmental. I was trying to stay away from the eye-rolling.

Adam: Sure. You weren't gonna name your kid “Seven,” for example, or anything.

Will: Yes. Shout out to the Seinfeld fans who may know that one.

Yeah. So it had to be a real word. Had to be a real name. And one thing that we knew was, so we're coming at, that we’re making this child from two totally different places on earth, like my lineage and hers. And so we didn't really want a name that was located in either place. And so when you look up at the stars, that was something that both cultures, both peoples could see.

In fact, that constellation has tons of names all over the world from different places. The Greek one is the one that we use and know. But there is a version of that in Chinese and many other cultures. And it was down to the wire. We had to leave the hospital the next day.

We still didn't have it picked out, which cannot recommend people to follow that path. But his eyes were very, he opened his eyes while we were having this, like we got, this is it, this is the last chance that we have to figure this out. And he opened his eyes really for the first time and was present with us.

It was, it sounds a little hippie dippy, but this was what was happening…

Adam: Well, you've been to Burning Man, so I figured we would get there.

Will: Yeah. Thank you. Thanks Adam. And his eyes were both the darkest and the brightest thing that I'd ever seen. And I was like, wow, this is like looking into a night sky. And he has like a little hair colic right in the middle.

It's shaped like a “o” And I was like, you know, that was one of the names on the list. And I was like, I, and he's masculine. He had this big, very like strong energy. So we had some more androgynous names that we loved that were sort of unisex, but those didn't really feel right for him. So wanted to look at him and make sure we had the right one.

And that's how it came to be. I don't know who had the final say. We were just like, are we cool with this? Are you cool? Like, how much is my mom gonna hate this? Like a lot? Because probably that's the right way to take it. So that's kind of how it happened.

Adam: Whose mom were you more worried about hating the name, your wife's or yours?

Will: Mine by a lot

Adam: Oh, okay. Your mom's got some strong opinions on names apparently

Will: My mom's got strong opinions.

Adam: Period. Full stop. Don't need to qualify. All right. Well , I'm sure your mom may listen to this at some point. I've had other dads tell me that their moms have listened to the program, so I won't go into too much detail on the mom topic.

So, one of the things that you talked about in your standup, which I found I don't know just very transparent of you and kind of very forward, was you talked a little bit about I V F in your journey getting pregnant. Now you made light of it and stand up. 'Cause no one comes to stand up , to cry.

They wanna laugh, they wanna hear funny stories. But tell me a little bit about your journey as a couple to getting pregnant. Sounds like it wasn't as easy as everyone thinks it is.

Will: You know, I'm 40. We're kind of at this place my wife's age is, you know, in the, in, in the later stages of being able to be pregnant as per medical literature. I think the reality is still, frankly, TBD they’re rewriting it now a bit.

But yeah, we tried for years to get pregnant and my wife had frozen her eggs previously when she was 31. So huge shout out to her. Thank goodness for that choice. and huge shout out to Google for paying for that for changing the culture beginning. I think they're at the tip of the spear on that.

And that should just be a thing in my opinion, that anybody who wants to have a kid should be able to have a kid. And so we found a wonderful facility in Los Angeles that I'll. Rep right now if people are interested, they're called RMA They have offices all over the US but we found a wonderful doctor there in Santa Monica.

And we got very lucky, like statistically through that whole process, like you go from the top of the funnel to the bottom and you like reduce the number of basically chances you get to be pregnant even before you begin the first embryo transfer. And so we were very lucky, very fortunate to have the first one land for us.

And yeah, so then we got pregnant. And I know a lot of people have difficult experiences. I want to just add that if you are hearing those and you are thinking about going through I V F. That there may be a reluctance for people like me to share the positive stories, the ones that go well, because if someone's at a dinner party telling you what didn't go well that's so unfortunate.

That's so sad. And it would be very hard for someone like me to follow that story up with, well, it was easy for us.

Adam: Right.

Will: I just want to say that people tend to advertise the difficult things, and I just want to say that this was very smooth for us and I wish anybody who goes through this process, wherever they are in it, all of the best, all of the best, of luck to them.

Adam: That's a great story and very hopeful for folks. There's been a ton of chatter on the Twitter's, excuse me, X the X and other places out on the internet about people asking, Hey, it seems like parenthood is really hard. And this idea of like, I'm getting older and I don't know if I can have a kid.

And it's really nice to hear that you had such a positive story with it. And you've got a, you know, beautiful, very masculine, Orion, six week old kid. So yeah, that's great. I'm happy for you and your wife. So one of the things I wanted to come back to is in our prep, which I know it's hard to believe that we prepare for these because they're just so smooth and off the cuff and whatever, but we did a little bit of prep.

One of the topics that you mentioned was marriage as a growth driver for self actualization, and I'm curious, what did you mean by that and how has that been true for you?

Will: Yeah, so let me just kick this response off with a quote that I love. It's by a writer and speaker named Harville Hendricks, his quote is, “the unconscious purpose of marriage is to finish childhood.”

Adam: Wow.

Will: Which is a pretty heavy idea when you think about it, right?

So I think for me, what that has meant is I'm someone who's looking for the truth. Like I am trying to understand who I am. That is on the written, in the, dome of the Acropolis, which is the most like important place of worship for the Greeks, which is to know thyself. That's where that famous quote is written among many other places.

So to me, that is something I take really seriously. There's a connotation that getting married, there's a loss. You can't be who you are. You give up stuff. You're compromised beyond who you could be. And I would like to propose that that is completely backwards. That you couldn't be who you can become unless you meet somebody who can inspire you, compel you, who can help you want to grow into the person that you really could be, and the way that's possible is only through relation, only through deep intimacy and going through all the barriers, the patterns that would prevent one, from being able to be deeply intimate to being deeply honest with oneself and someone else, and to foster that for someone else as well.

Adam: Wow. Well, that's what you meant by it. I was not sure. And now I know. I think I agree with you. I mean, I've been married now almost 15 years. I'm a very different person. Maybe not the best sometimes, but certainly a lot better than I think I would've been had I never met my wife. So I can relate. I hear you on that.

Will: I think people sense this a little bit. You hear someone say like, yeah, this is my better half. That's what the men say, right? I think that's kind of a keyhole into the concept here.

Adam: That makes sense. That puts that all in context now. So, speaking of your partner, you mentioned that she's an executive coach. And you mentioned that you tried for a long time to start a family. What was the decision like to even get started? Where were you both in your lives where you said, you know what, now's a good time to try and have a kid?

Will: Well, there were some external factors that we needed kind of put in place for us to feel like we could be doing this responsibly and make the space for it. The first was to have Trump outta office. Woo. Just needed that out of the way.

Before I felt, okay, obviously the world's in a shaky place, but, when that changed, I felt, okay this is a moment where this can happen.

We had been nomadic for a while moving from New York to Los Angeles. So we needed a place to be and wanted an address and a doctor and health insurance. All those things lined up - some of the basic life admin pieces. And I think we also needed to just, frankly, to each look in the mirror, hard - to say like, yeah, I've done all the things I individualistically needed to do, and now I'm ready to move on, to go through something else, through something bigger and different. And that took a minute. I'm, a lot of ways, not as mature as I wanna be, and so that was that precipice that I had to look at it and be like, yeah, I'm really ready.

This feels not only like something I want to do, but something that I would be foolish not to do.

Adam: Yeah, that's a really interesting point. This idea that you have to get ready by sort of finishing some of the things that you wanted to do earlier in life or getting some of that stuff accomplished and then saying, okay, I've done the selfish things, now I can do something that's more selfless and be able to take care of this other person.

So really profound. You know, a lot of people, I ask, what's the earliest memory you have of becoming a father? But you just became a father, so you've only got six weeks of memories. So what are some of your memories? What was it like, you know, having a kid becoming a dad? What was that like for you?

Will: Amazing. Absolutely amazing. It was a, it was like a comet coming at me that I had a baseball glove out to catch. You know, it was like this wild, huge thing. And I'm naive, but super excited. They hand me my child for the first time and I receive him, I got to hold him for the first hour of his life. While my wife was being attended to medically, and it was just me and him in the room together by ourselves, and I had him leaning up against my chest and I was just holding his back and I could feel his whole being breathe into my hand and thinking like whoa.

This is another level. Like I've, I don't know what I'm doing , but I feel like I have a lot of responsibility and that I can handle this even though I have no clue what's happening.

Adam: You know, it always struck me when I look at my kids now and then I look at their baby photos and you'll probably have an appreciation for this eventually, just how small they are at that moment in time, how tiny, they're like a, the size of a marble compared to how big they are now. So, that's pretty amazing. What a story, what a feeling. Tell me about the prep for delivery. Did you do a parenting class? You know, what did you do to get yourselves ready?

Will: Yeah, so I, full disclosure, I'm like an A minus student, like, put me in the advanced class, I'm gonna get an A minus 'cause why would I get an A plus? That's really point, that's like exceeding expectations in a job situation. Like probably in a lot of cases, that's not what you should do. Controversial statement.

Happy to explain on that later if we want, but my wife is not, she's a front row student. She wants the classes.

She's got the pen out notes ready to take. So we did a lot of classes. We did the birthing classes, we did breathing classes. We did actually a hypnobirthing class. Where the notion is you don't need to have an epidural.

You don't need to take these things. You can sort of mentally prepare with relaxation techniques to get you to delivery. Learned a lot about the process of delivery in that experience. It was taught by nurses and was really actually pretty great. And yeah, we took all the stuff, man I don't even know if we needed to, but we came in there, with the attempt to be educated medical consumers so that we could ask questions and understand the process and be present and not just sort of receive what we were being told as fact but could have a dialogue.

Adam: Yeah, I think that's really great. We supplanted that, we also took the parenting classes and the delivery class and stuff, but supplanted it also by having a doula who's you know, your partner and your sort of Sherpa on the journey. Which I also recommend, but it sounds like you all did all the things.

And then, I dunno, for you personally, when you got into the situation, did everything just like, go out the window or, you know, panic mode set in or what?

Will: No, not really. We had a doula too, so of course, you know, extra prepared and yeah it actually was like a hurry up and wait situation for us. And it took a long time and I kind of wanted to like, open up the computer and like do some other things, but that was like not a good idea. So I didn't, but yeah, it was, there were waves of it.

It was really different than the movies make it seem for us anyway.

Adam: Yeah. That would've sure been something. You're sitting in the delivery room and you're like I just gotta pop into the standup real quick, my engineers need me for something. Yeah, that would've been, that would've been pretty epic. So you're six weeks into the job of being a dad. What are some of the most surprising things that you've observed or discovered so far?

Will: Let's see. I think it's been really surprising to know how much of this is just built in. Like, they say this isn't something that I'm relaying that's novel, but when he's crying and I really don't know what the problem is, I can read him a little bit, I can understand what's happening. I could hear this cry is different than that cry.

I could know what just transpired. Therefore, it's probably not that thing again. Like if he's just been napping, maybe he doesn't need more napping, right? So the amount of stuff that's innate, that's not coming from here is really wonderful and joyous to experience. So that's been surprising.

It's been surprising watching family show up and wanting to reconnect and strengthen every connection that we've got with our families and to watch them show up and show up in new ways that I think surprised even them and how wonderfully that's happening. So that's been really beautiful too.

Adam: Awesome. And you also mentioned, I think baby wearing is amazing that you have this new accessory can just wander around town with are you maximizing that? Yeah.

Will: I put him in it today. So it's basically, we have I'll actually rep this brand 'cause I could recommend this product. It's called the Lalabu and it is a t-shirt that you can wear. Guys or gals can buy one and you can pop your baby in. It's sort of like a kangaroo pouch and they're just sort of sandwiched in there. And then you can like do things. You can make a cup of coffee, you can take a walk. And pretty much what happens if you start moving is they fall asleep 'cause they feel you. And being skin to skin or as close as possible to them is really regulating for their system and for yours. Like if you're feeling a little frantic, if they get in there, if you're like, oh, this is cozy, this is wonderful.

Our son is also extremely hot. So if it's a little chilly out, we just pop 'em in there and then we're good.

Adam: Is a wearable blanket.

Will: yeah, it's really adorable.

Adam: Isn't it amazing just how. Kind of smushed little kids can get, and they're just happy as a clam. Like, I guess it's because that's how they're, they grow for 10 months, you know? But isn't that amazing? You can just like, go around your day and this kid is just sandwiched on you and, totally fine.

Will: Yeah, it's like the worst coach flight experience I can imagine. They're all about it. They're into it.

Adam: Yeah. That's a great way of thinking about it. And now I'm terrified of flying coach again. Okay. So some real talk here. We, talked about the little guy. You also talked to me about this idea that men need to evolve what the definition of husband and father is. Tell me more about that. What did you mean by that?

Will: Yeah, so, so my parents, as I told you, they have a pretty standard setup. One parent went to work, the other one did not, and they followed the gender norm rules. And my dad came home, he had more work to do and my mom would make dinner. And that's incredible. That's an incredible sacrifice that they both made for us.

I'm extremely grateful for it. But just by the notion of my wife also working, that setup doesn't work. I can't just replicate what my dad did and all of the behaviors, all of the day-to-day life patterns that underpin that - can't come off of work at 6:00 PM expecting my wife to have dinner ready 'cause she just got off work too, right? So, so what does that mean? That means I have to be a full co-parent. That means I have to be a full like household member with her. So the “women's work,” that forever has been ignored and neglected and uncounted in terms of value and G D P and taxes like this. Just an enormous amount that's been written about all that and how that's not considered factual.

It's not real. It's like this is imagined thing that children are raised by themselves. You have to participate in that in a ongoing, consistent way. And that changes so much of the dynamic. So from my perspective, it's like I can't just copy what my dad did because then I'm gonna get divorced, you know, so real simple situation.

Adam: Yeah. Yep. That's how that works.

Will: And my wife doesn't wanna copy what she grew up with either. And so we have to go make it up.

Adam: Yeah.

Will: We have to go make it up. Now that's actually a pretty complicated, difficult thing to do. And every time I see a couple, whether they're younger or older, and they're doing it in a way that looks interesting and valuable, I try to learn and soak up as much as I can from them, because I think that we're all trying to figure this out in real time together.

And it's a challenge. It's a challenge. And these role models, like an evolved man, someone who can be angry but not vicious or cry, but not embarrassed, right? There's all these like things that we don't really get a lot of demonstrations of. It's not in the news, it's not in the media, and we have actually so many anti examples.

 It can be confusing and everyone can feel lost. So I spent a lot of time thinking about how to create this for myself, how to demonstrate this for my son, and how to learn and also give away as much of this as that I've learned as well.

Adam: Wow. That's really great. And I think a lot of people will appreciate hearing that on this show. So, you're currently in a interim or fractional role, or you're not in a full-time, you know, W-2 employee situation, right?

Will: Correct.

Adam: What have you decided to do, or how have you and your wife decided to handle parental leave?

What does that look like? When you're working for yourself and when you're not working, you're not really collecting a paycheck.

Will: Yeah, this is a good question. My wife took maternity leave - and the state of California is actually pretty generous. They will pay, I forget the exact percents, but I wanna say like 80% of the best month that, or the best quarter that she's done in the last year or two, like the state is really way ahead of the nation.

Adam: Oh, that, and that's as an independent self-employed worker that they’ll pay that?

Will: Correct.

Adam: Great. Great to know. I did not know that.

Will: Yeah, I didn't either until recently. Why would I know that? So, yeah, so, so kudos to California and if you're living in another state please do something. Tell somebody. I feel like Congress has no clue how many people are freelance and there's very little protections. It's a huge number. It's like 30% of the workforce is in someway, freelance. It's, I don't understand why there's so little done for us. So that was a decision she made, and that's where that's coming from. By being fractional I have a lot of control over my schedule and how many clients I have. Thankfully, I have the ability to have choice with the clients that I have.

So I have some work turned on, some work turned off, so I've got enough time to be present to be a parent despite this being a very incubatory time for our child, and for us as a family.

Adam: I know that you're only six weeks into the job, but I'm wondering maybe through reading or through already trial and error, have you developed any kind of frameworks or guardrails for parenting? One of the things you mentioned to me was this idea of having a kid means simplifying your life.

So I'd love to hear more about that. And then if there's any other best practices to use the PM parlance that you may have developed in your short time as a dad.

Will: I feel like before I was a dad, I had this huge to-do list that there's like work streams everywhere privately, like personally and professionally. You know, how do I achieve more and stuff and get ahead. How many years until I can have a huge boat? I don't know, I don't know where this was going, but that was the unspoken components of it.

And then you have a kid, and then things get simple. Things get really simple. You can't begin to be even contemplating some of that stuff. And then what really matters starts to reveal itself in clearer ways. So I'd say that just shows up. That's great. The other frameworks I have to the extent that I have any, one that I like is that you just can't spoil your newborn. The term is that this is their fourth trimester. That they're so helpless that they need to just establish basic trust with their caregivers. And so you do that by showering them with love and if they cry to show up and to hold 'em and to console 'em and to not feel that notion of like, you know, walk it off.

It's so, you know, what are you crying about?

Adam: Toughen up kid. Six week old kid.

Will: There's probably a time for that if that's the route you want to go. I'm not here to judge or prescribe any, what do I know? I've been doing it for six weeks. So yeah, if you wanna do the tough love thing later on, I guess that's cool. But right now I'm, you know, everything that I'm seeing and reading is suggesting that's actually a misnomer.

There's no such thing as spoiling your newborn and that feels really good. 'Cause that's kind of, feels like what's germane to me and what I would like to do. And then the last framework I have is just to drink a pot of coffee a day.

Adam: That's amazing. How are you doing on that goal, by the way?

Will: Excellent.

Adam: Yeah.

Will: It feels good to just let loose on one thing, like the safe drug and just hit it hard.

Adam: One of the few legalized drugs out there. Coffee. That's awesome. I could probably benefit from not drinking a pot of coffee a day. Maybe you could tell from my energy level on this show. So I wanted to ask you about parenting books, right? Because, we'll talk about that maybe a little bit later.

But have you been reading a lot of parenting books? Is there anything in particular where you're like, Ooh, that one I highly recommend?

Will: My wife has been taking the charge on this one. She's reading the Montessori book Montessori ground here. So obviously that's worked out really well and all. She's reading, like how to… this one… how to like raise a baby like a French, how to raise a French child. Which I also think she's digging and seems cool, but I've read none of these.

There's, oh, we also have like, what to expect in your first year and week by week. Something like week by week. So things that people have told us to get, we've got and they're helpful. The internet is not, in my opinion, very helpful because you'll google anything and it's, here's the range of answers from like, you're fine to go to the ER about everything.

So it's just, it's like kind of comical and so don't trust Google. Is the short story here.

Adam: Have you attempted to go to chat G P T and ask it parenting questions? I don't know if anyone actually does that and expects to get a good answer, but have you even tried it?

Will: I have not tried.

Adam: Maybe this is homework for after the show. We'll see.

Will: I'm open to it. I'd be curious to see what it had to say, but it's not gonna be worse than Google. Like I know that.

Adam: This is true. This is true.

It's certainly gonna sound more authoritative than Google when it gives you an answer, right or wrong. So I've found and you will likely find this too, that partnership is really important when you have kids, but it's also one of those things where you're not gonna agree with your partner, your wife, a hundred percent of the time.

Have you already identified some of the areas where you and your wife don't agree when it comes to parenting or baby stuff?

Will: Yeah, a little bit. Um, developing story. I can get back to you on this with more research.

Adam: Hot off the presses.

Will: Yeah, I'll follow up with you in a few months on this one, Adam. The short story is that I think that she's a little bit more careful. Maybe you could argue caring. I'm not sure if I would go that far. But the other path that I've sort of been slotting myself into is I think it's okay to take a little bit of a risk.

Adam: Yeah.

Will: Risk is a tricky topic, and describes in some sense, like kind of whatever happened during Covid and all of the factions and sides that tug of war got played out on. At the end of the day, it was a conversation about risk. What is okay and why? So, it's a tricky, it's a tricky debate. We have it poorly around us all the time, so me and my wife are also not doing a great job of it. But the…

Adam: Well, you're sleep deprived. It's allowed. It's allowed.

Will: I appreciate that. to get specific, 'cause maybe your listeners and viewers are like, well, stop being so euphemistic. Well, they say that when you get home from wherever you were with your kid, take them immediately out of the car seat. Now we have a doona car seat.

There's a car seat in a stroller in one. You can fold it in and put it into a car. You can take it out, unfold it, and off you go. So we take him out of the car, we bring him in the house, and he is chilling in his car seat/stroller for some amount of time. My wife immediately wants me to take him out.

She's still recovering, so it's not easy for her to personally do this. And he's strapped in. He's either asleep or awake, and I don't see what could happen to him. This is probably as safe as a place as he could be for a short period of time. And by short, I mean, you know, like a day. No, I'm just kidding.

I mean like a few, like a few minutes.

Adam: Yeah. Yeah. 10 minutes.

Will: Three minutes, five minutes.

Adam: Put away the groceries, you know, whatever.

Will: Bathroom break, wash the hands, whatever, something quick. Some of the advice is like this can add up and turn into, you know, a half hour show. Before you know it, you're season three into “Friends.” So I get the concern that you shouldn't leave your child in the car seat for a long period of time.

 So yeah, we've not agreed on that and jury's out so far. I'm just folding on this one.

Adam: Smart man.

Will: Well, there's that adage like, happy wife, happy life, which I don't know if that's true, but I do know that the inverse is definitely true. If your wife is unhappy, your life is less good.

Adam: Yeah. You know, I haven't heard the, take them immediately out of the car seat, but I also have older kids now and not a newborn, and possibly I just missed that reading, that required reading when I was. When I was young, but my kids would fall asleep in the car seat and taking them out was like a mortal sin because they're gonna stay asleep as long as we, sometimes we wouldn't even turn off the car, just pull up and sit there anxiously looking behind us to make sure they were still asleep because as soon as that engine went off, oh, they're waking up.

So I hear you on that. You may never agree on that with your wife, by the way, by the time you come to agreement, your kid will be out of a car seat, so yeah. Or you won't have the portable one anymore.

Will: I am gonna put you in touch with her and maybe you guys can reach your own accord.

Adam: I am in so much trouble now. I'm gonna get an angry email. What is something that you've already realized that you have to give up becoming a father?

Will: Well, so far I've had the pause stand up and it's a good trade off to make that pause because I can't, that would be a disaster for me, my family, my marriage.

To be like I got a couple mics to do and a show tomorrow. That would be a horrible idea. So that's a just a hard no. And I don't there's no hard feelings about it. it's a surrendering feeling and it's, it feels right. This is also a great time to write material.

It's a lot happening and a lot happening really quickly. And so a lot of funny stuff happening. So, we were trying to get pregnant for a while. We missed a Burning Man. We were trying to go, we had to miss another one, you know, 'cause then we got pregnant. The other thing that I've had to really let go of is like, sense of scheduling and looking at the clock.

Like, let's see if we could leave at 3:00. And then he immediately like, throws up or we have to change his diaper or he gets hungry. Suddenly 3:00 is 5:30 and now we're doing the thing that we said we were gonna do. It's like, okay. Cool. The clock is not part of being a child, you know, not being an infant.

So it's like, I gotta let that go. That's a tricky one. And the kind of, the feeling is a little bit like everything in my old life is now behind a paywall.

Adam: What does that mean exactly?

Will: like, I used to get the times for free. I could just click on any article I could take as long as I wanted with all of 'em and just read them, you know, leisurely from any place.

And now if I get like one headline in before the interruption starts I get to have a jog. I get to like do a thing like run an errand that feels like I'm now behind that paywall for like a hot second, and then it's gonna be back on the other side before long.

Adam: Yeah, that's a really interesting way of, describing that. I once had a neighbor who was a dad a few years older than me. His kids were a little bit older, and I said, what do you want more than anything else right now in your life? And he said, you know, I just want to sit down and read a newspaper for 45 minutes with a cup of coffee. And I said that? You could have anything. That's what you want. And he said, yep, that's what I want. And now I appreciate that sentiment. You probably do too. That one New York Times headline, it better be a good one. It rarely is, but it better be.

Will: I think the piece about that, if I had heard that before I had kids, I would've said, this sounds miserable. Like I don't want kids, I'm, this isn't for me. But then when you have a kid and then you get that 45 minutes or even 5, it actually feels so good. It feels so, so good. It's like all of a sudden you quit smoking, you could taste food - really, and it's so pure and pleasant.

It actually like that contributes to that goodness, that purity of that feeling. So it's actually a totally cool trade off. At least six weeks in.

Adam: I think you start to appreciate some of the things that you didn't have an appreciation for before. Something simple like reading the newspaper or you know, having a little bit of quiet time reading a book, something like that. It's now really special. And it, you make the most of it. So.

Six weeks in, what is a mistake that you find yourself making as a dad or, and maybe it's hard to know. Maybe your wife tells you if you've made a mistake, or the internet. God, I hope not, but yeah. What's something that you feel like you're messing up?

Will: I hope no one's looking at the internet to decide if they've made a mistake in life. That's just really the wrong yardstick for a whole lot of reasons. I think the mistake I've made is, but just like a little overconfident in life, and so that kind of filters into being a dad. Like this is probably fine, right?

That's cool, right? Like, whatever. Let's just do it. Let's be risk averse a little bit. Let it ride. I'm not sure that's always the best plan. He is a small being. He needs to be treated carefully and my wife is wise and she needs to be heard, and so there's a balance that has to be struck.

Adam: Yeah. It sounds like you'll have a positive take on this, but how do you feel about the idea of the startup hustle culture and how that might fit in with your, the growing importance for you of being a dad and being there for your kid?

Will: I personally was never a fan of this. I think that there are reasons for going faster than you can for some amount of time. But as you know, if I was speaking from the ownership class, like I might have a tycoon-ish opinion on the subject, I’d say yes. You know, like they need to work 70 hours a week minimum to, you know, make my company flourish.

Yeah, I see that point of view, but I'm not in that position, so I can't take that. And I'm not sure I would espouse it either. 'Cause I think if you have a great idea and you execute on it well, and you create a good culture, you don't really have to worry about it.

And I think a lot of the death marching, the late nights, the oil burning again and again is not sustainable - lowers morale, creates negativity and resentment. People don't like it. And now people have, if even after this quote, “talent tsunamis,” I've heard the VC class refer. This wave as it's starting to change and the employee, the potential employees, they're starting to gain a little bit more options, some control, some choice, and that is going to continue to reward the companies that have a great work life balance, that have a sense of maturity about what they're doing, where they fit, what their mission is.

And so I think I can't say that I ever subscribed to it. And when I saw people, with families who were in those positions, I saw them leave and have really great boundaries, and no one really questioned them. They got their stuff done on time, and they left. And no one really could question them.

And the rest of us who didn't have that other like bookend in their life would be the ones who would kind of let it bleed, boundaryless, whatever that word is, into the rest of their lives. And I think to a detriment to self, to team and to company.

Adam: Yeah. Yeah. As you know, sometimes they say people that are married to work, right? Well, you have someone else that you're married to and now you have someone else that depends on you you know, even more than your team does. So.

Will: That sounds like a terrible marriage.

Adam: it, it does. I agree. I agree. Well, thanks so much, Will that was my last scheduled question.

Now I would love to get into, The rapid fire round. So the way the Rapid fire works is I will rip off a bunch of questions here, just run through 'em, and you say the first thing that comes to your mind, and if you've got a funny story about it, please feel free to share. So are you ready, sir?

Will: Fire away.

 Adam: First question. Most indispensable parenting product you've ever purchased?

Will: The Fellow Tea Kettle. I say this because it's not on any of the parenting lists and it's not even a parent item. This is a tea kettle. And by the way, anyone that like this would work to, you can set a specific temperature for the baby formula. By the way, we are slightly baby formula people. Don't shame me.Thank you. 

Adam: No judgement.

Will: And uh, we do both, but it will bring it right up to temp. You don't need a bottle warmer and then you can just make your formula, off you go.

Adam: Oh, I love that. Love that. We're gonna put that one in the show notes. On the other side of the coin. What is the most useless parenting product you've ever purchased?

Will: The Hatch Rest 2. I dislike this product immensely. It gets rave reviews on the internet. I think people are legitimately excited about it for good reasons, but for us, it's a really expensive nightlight that also is a noise machine. And you, by the way, you could use Spotify and a sono speaker or YouTube and an iPad.

You don't need to go buy anything for a noise machine. You can turn on a radio in between stations and get what you need. So, and if you need a nightlight, well that's not $80. So I don't know why this thing exists.

Adam: Did that somebody get you that on your baby registry or did you, was that something you registered for?

Will: I think we saw, we got just, you know, compelled 'cause others were doing it and we were like, I guess we need this thing.

Adam: Yeah. Turns out you don't. Okay. Good to know. They will not be sponsoring the show, but that's okay. What is your go-to new dad wardrobe?

Will: I would say it's a pair of Asics, it's white socks pulled up mid-calf to let everybody know I am not cool - at a distance. Don't even bother. And I like to wear short shorts, show off a little bit thigh. I personally think I have nice legs. This is that overconfidence piece I was talking about earlier. And then a t-shirt or that Lalabu where I can kangaroo him in there.

People think I look grossly outta shape from a distance, which is amazing. And then they get close and they're like, oh, I'm sorry. I've been judging you silently a block away. You are a dad. That's amazing. So the watching their face change is delightful.

Adam: That’s the best - grossly outta shape only to find that you are wearing another human. All right. Love that outfit. That sounds like just a, just an A+ outfit. Excuse me, an A- outfit if I remember what we talked about. How many parenting books do you have in your house?

Will: Five

Adam: And how many of those have you personally read cover to cover?

Will: bagel. Zero.

Adam: Bagel. Okay. Alright. Minivans, are you pro minivan? And has that changed since you had a kid?

Will: I am and have been pro minivan. I'm also pro station wagon

Adam: Ooh.

Will: And I think anything - you, if you zig while everyone else is zagging, I think that's, I think that's a win. And that's really cool. So that’s where I’m at on that one.

Adam: Okay. You are definitely zigging while everyone else who I've asked this question is zagging. So good. Kudos to you. Okay. Will your standup, when you get back to it now, include dad jokes?

Will: No.

Adam: The audience is not going for those.

Will: Nah, I'm not, that's not why people come out. You're certainly not gonna build a fan base doing that. From my perspective, it's all about being as honest as possible and real. And Dad jokes have their place. Puns have their place, but that's, it's not where I roll.

Adam: Okay. Where is the most difficult place that you've changed a diaper so far?

Will: Yesterday we did this at the beach and for obvious reasons, that is difficult. Thankfully it was a low wind day at the beach, and I think we, we got out of there mostly okay.

Adam: Yeah. Let me tell you harder, if you have a girl, changing them at the beach, and I will say nothing more than that, we're just gonna leave it at that. On a scale of 1 to 10, how difficult is it to bathe a newborn?

Will: Two?

Adam: Oh, so not very hard for you, ok.

Will: I was surprised by this question ‘cause like, what are people, are they going in the bath with their baby? Are they wearing rubber gloves while doing this? Are they, you know, they greasing themselves up prior? I don't know why this would be so hard. We've been we've been handling it.

Adam: You, do you do it in like the kitchen sink or something like that, or with a little bathtub or…?

Will: You know, we have one of those kitchen sinks that's subdivided into because the person who invented that's never washed a dish in their life. And if I could find that person, I would slap them in the face. They owe all of us a huge apology. Do not like that person. And our bathroom sinks are very shallow, so we had to buy a very annoyingly, a piece of plastic to put this child in.

And that thing has like a little like seat also he can chill out in while he is a little guy. So he kicks it in there and he's pretty, he's pretty happy.

Adam: Cool. This is better than hosing him off in the yard for sure. Is there a Disney or Pixar movie that you are secretly a fan of?

Will: One of my - it sometimes has been my top movie period is “Wall-E”

Adam: Love that movie.

Will: It's permanently in my top five. Phenomenal film. Love it.

Adam: It is a great film. What was your worst experience assembling something for your newborn?

Will: We bought a crib that was advertised as Green Guard Safe. So it's a low volatile organic compound paint, which basically means it's not very smelly. And then I opened it up and it was like…

Adam: Oof.

Will: It was like, I was like fumigating my house. It was like horrible. So did that, built it like 50% had the doors open and fans blowing and three days later, still super bad. And we were like, this thing needs to go. So.

Adam: yeah. Oh, that sounds terrible. Not only is it really frigging hard to put together a crib, but you have to do it while fumigating yourself basically. That's terrible. How many hours of sleep do you actually get with your newborn?

Will: You know, this is not too bad. I want to demystify some of this. Like it's very newborn dependent. We have a very good child on this sleep front, and my wife and I are routinely getting about five to seven hours of sleep. It will not be continuous. It's like more of the Da Vinci style approach to sleeping.

So it's like three here, four there, two there. Maybe a nap in the afternoon while he's sleeping. You know, you, do what you can, but it's actually going alright.

Adam: Awesome. I feel like there was also a Seinfeld episode where Kramer decided to sleep in short increments or something like that. So this is a second Seinfeld reference on the show. Most absurd thing that you've done to make your child stop crying.

Will: I am not a Latin dance professional, and I, yesterday for no really good reason, thought that what he needed was some Salsa in his life. So I started to make up, maybe it was the Merengue, I don't even know what I'm doing, and he was super unimpressed and just eyes glazed over and just turned to his mom and just cried louder.

Adam: And then she had you, your wife, Amy, you said her name was right? Has you dancing Salsa, and your son crying and is just looking at the two of you, like, when did I get a second child in my life? Amazing. Well, with that Will, we are done. Thank you for participating in our rapid fire round.

This has been super fun having you. I love all of the topics that we discussed and it's been a real pleasure. Thank you for taking the time, too, with a six week old to come on the show.

Will: Yeah. Adam, thank you so much. It's a pleasure to be here and yeah, thanks for listening.

Adam-IntroOutro: Thank you for listening to today's conversation with Will Rocklin. If you enjoyed today's show, please subscribe, share, and leave me a review. It'll help other people find this podcast. Startup Dad is a Fishman AF production with editing support from Tommy Heron. You can also stay up to date on my thoughts on growth, product, and parenting by subscribing to the Fishman AF newsletter at www.fishmanafnewsletter.com. Thanks for listening.

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