#3: Jake Stein, Common Paper

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 3, and I'm so excited to have Jake Stein on the podcast today. Jake is the co-founder and CEO of Common Paper and the former CEO and co-founder of Stitch, sold to Talend in 2018. Jake was also a client of mine and a joy to work with, I might add. And that's how I know that he was the 44th ranked table tennis player under 21 in the state of New Jersey back in the day. Jake and I had a wide-ranging discussion about the pros and cons of distributed teams, the questions that Jake and his co-founder asked each other before they started their company, the specific practices Jake uses to manage his own psychology, and what challenges Jake encountered once his company Stitch got acquired. Jake talks about his biggest professional mistake and the rituals he instituted around feedback parties and Whale Wednesdays. Please enjoy this conversation with Jake Stein. Jake, welcome to the show.

I'm delighted to be here.

The first question is, tell us about table tennis. Is that still a hobby you, you pursue?

It is. And, uh, the, the pandemic shut it down a little bit, but I just played for the first time, uh, in my friend's basement and it was glorious.

Oh, amazing. Amazing. Everything's coming back, including ping pong.

That's so beautiful. That's right. That's the most important thing.

That's right. That's right. Jake, I wanna start by asking you about your background. Where did you grow up? And what were the early signs, if any, that you'd end up being an entrepreneur?

Sure. I, uh, I grew up in New Jersey, uh, in a small town called Montville. It's like a suburb of New York. Uh, and I think if I had to pick one thing, the earliest thing that was an indication that entrepreneurship might be in my future, it was probably that landscaping business, uh, where, uh, you know, I around the house. My dad had me do a bunch of, you know, odd jobs, you know, mulching, pulling out weeds and things like that. And I remember sitting there one day and just thinking, this is kind of nice. I wonder if someone else would pay me for this. And then so for a couple summers, I got a few of my friends together and we just did a bunch of lawns, did a bunch of work for people in our town. And at the time, I didn't think of it as like, oh, wow, this is a startup we're starting. It certainly wasn't, but it was probably the first step down that journey.

So you, you both enjoyed it and you also thought, oh, this is like an economic, an economically viable business I could do.

Yeah. I figured that, you know, I saw all the commercial landscapers around town and I knew that they were getting paid to do this stuff and I was not getting paid to do this stuff, but I felt like if I did the same thing in someone else's yard, that someone might pay me. And so, uh, yeah, we designed flyers. Uh, they were very goofy. It was like, you know, the tagline was keeping kids off the street and in your yard. Uh, and, uh, and, uh, yeah, we, uh, me and my friend Joey, he drove the car and I leaned out the side and stuffed those flyers into mailboxes and, uh, ended up getting a, like a nasty call from the local postmaster telling me that that was against the law. But by that point we had already generated our leads and, uh, yeah, it was great.

That's amazing.

Wow.

Well, from there, those, uh, those auspicious beginnings to your, your journey as a, as an entrepreneur, I want to focus a bit on Stitch because that's really how you and I met originally through your, your journey with Stitch. And so I'm sure that there are many ways you grew as a leader and as a CEO, and also probably as a person. Can you share a few of them with us? If you think about your journey, actually in all of your, in all of your kind of entrepreneurial journey, but specifically within Stitch?

Sure. Yeah. And, and I mean, in starting out, it's really remarkable to me how little, uh, I knew, uh, I mean, just, I, it wasn't, it wasn't on my radar that like management is a thing that you could be good at or should be good at. It wasn't just like a topic that I was thinking about. And so there's so many things that in the early days I look back on and just like hit myself in the head. Like it took me years to set up one-on-ones. I just didn't know that that was a thing that you were supposed to do. And some of our early people were like, you know, I really wish I got more feedback. And I was like, yeah, that's a good point. That would be nice if you got more feedback.

So you like invented one-on-ones.

Yeah, I— and very slowly and circuitously, where me and my co-founder would meet with people first like once a year, and then once every two quarters, and then once a quarter. And then eventually I think I read, uh, some blog post about like one-on-ones. I was like, oh, that's just like a much better version of what we're doing. Uh, and, uh, yeah, so I think just some of it is just the, the nuts and bolts of like how to be a good manager. Uh, and then, you know, moving on, some, some of the things that took me a while longer to figure out, uh, and to grow on that journey are around like making sure the team is aligned, making sure the, the business model is aligned with the product. Those are things that took me a lot longer, um, and I think are like much more a part of, you know, the early stages of how I'm thinking about the company today and just weren't on my radar at the beginning of of this journey and kind of have been incremental steps along the way.

So let's double-click on that a little bit. When you said, you know, learning how to keep the team aligned and understanding, making sure the business model was aligned, like what did you actually— I guess I would like to know if you can think, if you can remember this, what was missing that made you think, wait a minute, I have to make sure the team's aligned here. And then what specifically did you do to make that happen?

Sure. And some of this was like, we had a great independent board member, a guy named Chuck Dietrich., at Stitch, and he used to talk to me about alignment and saying how important it was. And like, I understood all the words he was saying, but it didn't— it took me like years for it to like actually click, uh, for me. Um, and also just sometimes, you know, individual conversations with members of the team where they would ask, you know, why— like, they're on the sales team, they're asking why the engineering team is working on this feature rather than that feature. Or like, you know, I'm someone on customer success saying, hey, this customer is annoyed that they encountered this bug or that they don't have this thing. Why don't we, why don't we do this? So just thinking of like lining up the different teams and the different people on those teams so they all know where we're headed. And just the— there were lots of examples of those little frictions, uh, along the way. Uh, and then the other, like when I zoom out and think about like the business model aligned with the product, aligned with the go-to-market, um, One of the things which we didn't do as good of a job in RJ Metrics that we had a much better alignment at Stitch was thinking about, okay, who is our target user? Uh, what is the way they want to, uh, find out about, evaluate, and use a product? And then making sure that they could come to our website and use it that way, and that, uh, they could buy, uh, the way that they want, and that we could upsell them the way that we want. And so that, like, our pricing model had to line up with something where we were, you know, targeting developers. Those developers did not love big upfront sales processes. Like at RJ Metrics before that, we had, you know, a gated thing where you had to talk to a rep and then you had to go through an implementation where with Stitch, there was like a design consideration where we wanted you to be able to sign up at 2 in the morning, beginning value at 2:15, and we would just find out about it later in the day when we came in. So just thinking about all those steps around who the people we're working with are, how we design the product, how we charge for the product, how we support. All those things need to be like lined up, otherwise they're gonna bump into each other over and over.

Yeah, so true. And so how did you line those things up? I mean, I'm sure there was some deep thinking, but then also how did you like then talk to people about it? And then I'm sure you had to re-talk to them about it, right? Because people forget.

This is a great point. Yeah, so I think part of it is just talking about it explicitly, writing it down, and like making an affirmative decision rather than having, uh, things just happen. So that's step one. The other thing which, uh, came very, very unnaturally for me, and it's still a challenge, but I think is— I'm better than I used to be— is just repeating stuff over and over again. And, uh, to the point that it seems like awkward to me, uh, where like I, for a long time, uh, it, it blew my mind that I would talk to people and they weren't clear on the vision or they weren't clear on the mission, uh, and then so I started of just like in every all-hands meeting, I had a slide about, you know, our mission and what we were doing and the vision and who we were serving. And I would like pick one. And I actually went through a couple different iterations on how to incorporate it because at first I talked about everything, every all-hands meeting, and that felt kind of repetitive. Uh, and then what I did was like, I just picked at least one or two things from that slide. So we started every meeting with the same slide and I said, today We're going to talk about an example of transparency and how it worked and what it cost us, but what it got us. And so just like over and over again, talking about how all these things fit together and how it actually relates to what is going on in our business on a regular basis. And one other thing that was really helpful is picking things that kind of stick in your head. Like, and it reminds me of like that Seinfeld episode where like, Costanza, you're Uh, but like we had, uh, one of our values was, uh, DTRT, uh, which is an acronym for Do the Right Thing. We have a whole, uh, couple sentences around like what it means and how to implement it. Um, but I think a big part of why it worked is that it kind of was like a fun thing to say. And so it like was easy for people to keep in their head. It was easy for them to bring up in conversation. And it was just like this shorthand for everybody had read the the expanded definition of what this means, how to apply it, but you could just say that thing that rolled off the tongue and that got brought up a lot more than something else, which was less fun to say. Yeah.

Oh, Jake, it's so true. You know, for a long time, you know, as a coach, I try to constantly like give people tools and memes to remember. And I used to really shy away from gimmicks. And so then, you know, somebody once said to me, they should get curious, not furious. And I was like, whatever. But now I use that all the time by myself. Because it's actually like super helpful when things rhyme or when they have some play on words or they're fun to say, because to your point that they are memorable and actually it's not that they understand, it's that they remember.

Yes, absolutely. And I am someone who often is guilty of using like 5 words when 3 words will do, or, you know, adding more specificity and trying to get to some Platonic ideal of rightness. And so I'm always now very sensitive to someone saying like, eh, that's kind of wordy, can we cut that down? And in most cases, it's way, way more valuable to get to the short, snappy version because that'll give you 80 or 90% of the accuracy and actually get remembered rather than have something that's theoretically right and never gets used.

Right, that's, yeah, that's great. So Jake, I'm curious about some of the other specific skills that has to do with what you were just talking about with managing other people. Were there other specific skills that you had to learn or that came easy to you in terms of either managing yourself or managing the business?

I would say, I mean, one of the things that I had the most challenges with and also feel like I've made a lot of progress on, but it's still an ongoing challenge, is just like managing my own psychology.

Mm-hmm.

You know, there's inherent in this business of, you know, starting a company and seeing it grow and having occasional dips and problems. Uh, it's just like a roller coaster of emotions. Uh, and so trying to make sure that number one, I can at least just manage and deal with the peaks and the troughs, uh, better, but then also set the right tone for the rest of the team because I often have information that they don't have and folks are cognizant of that information asymmetry and they're looking to me to be like, okay, we just came out of a board meeting Or he just came out of a board meeting. Does he look pissed off?

Right.

Or does he look excited?

Right.

And what does that mean? And is that, does that mean that, you know, the company's going down the tubes and he just hasn't told me yet? So thinking about like, what is the nonverbal cues I'm sending to the rest of the team? And then also just how I modulate my own happiness or frustration or excitement or whatever, given a big customer just signed on or a big customer just churned or we didn't close the round or we did.

Yeah, yeah, yeah. I think that is like so hard for all founders. I mean, the journey is inherently kind of filled with ups and downs. And actually, while we're on this topic, since it's filled with ups and downs, I can imagine for you, you don't always know if you're winning. You think you're winning, but then you have a setback. And so it can be like a little bit circuitous. How do you personally deal with the bad moments in your day-to-day?

You know, I— there's a couple different things that I do. Um, one is, you know, I have a meditation practice which has been really helpful just in terms of, uh, dealing with it, with those day-to-day things. Uh, there's sometimes that I don't do a great job of dealing with it and I get really frustrated and I go for a walk or I go for a cry or something like that, and that honestly helps. Uh, and there's, there's this concept of, um I think this is from like a Ben Horowitz essay around feeling pressure versus applying pressure. And I found that very helpful where sometimes if I like feel like, you know, everything is caving in on me and, you know, someone just quit and the thing didn't work out and think like, oh my gosh, I just can't handle all this. I remember I actually don't have to handle all this. There is a group of people around me and I can ask more of them. And since they are amazing people, they deliver on that and they, under pressure, they do great. And so like just thinking about we are a whole, it is not necessarily up to me, uh, to handle all this and fix all this. Uh, and that has been really helpful. Uh, and the other thing is like I recently started doing just like a little gratitude journal, um, where, uh, every day in the morning and before I go to sleep, it's super simple. It's just like 3 bullet points. Things that I'm grateful for. And it might be things at work, it might be things personally. There's just so many things going right, even on my worst day. Just reminding myself of that has been really helpful.

Mm, that's amazing. A very powerful practice. That's really great. So speaking of people around you, let's talk about co-founders, right? Because you certainly had a co-founder at Stitch. I know you have a co-founder at Common Paper. I think they're two different co-founders, but talk about how you met your co-founder, maybe back from Stitch, and talk about your relationship and some highlights and lowlights.

Sure. Uh, so Bob is my co-founder from RJ Metrics and Stitch, uh, and, uh, we met, uh, at a summer internship and then first job out of college at a firm called Insight Venture Partners and, uh, just became friendly there. It was a small, like, analyst class, only like 6 or 7 people. And so got to know each other working there. And he was the one, like, I was very interested in a startup and I had a lot of ideas that I wasn't thrilled about. And he was the one that had the specific idea that we ended up doing.

Mm.

Um, so it was great for a lot of reasons, both because I knew him and I had like worked with him and seen and like respected him already. So it wasn't, uh, as big of a leap. Um, and it was great where I feel like we had a very professional focus relationship at first, and then over the years of working together developed a really close friendship as well. Um, and where now, even though we're not working together, uh, day to day, Uh, we catch up frequently. I'm actually going to his house tomorrow. Um, and, uh, we're, um, it's still like something where I go to him for advice, he goes to me for advice, and we are very philosophically aligned about how, uh, a lot, a lot of areas. So he's an amazing sounding board. Um, at Common Paper, uh, my co-founder, uh, is a guy named Ben, and he actually was, uh, started as an engineer at RJ Metrics and was promoted and promoted and promoted. And by the time the company got acquired, he was leading the engineering team at Magento. And just an amazing human. And like, as I was setting out to start this business and thinking about like, who would be the, the right person, again, it was a lot of similar things where like, very valuable to have worked with someone in a professional setting. And like, I knew him somewhat, you know, socially as well, but it wasn't as close. And we've, I think, you know, we've been at Common Paper only for a little while, but it's been so great spending time with him. And the thing that I think I got lucky with, with Bob and then made a very deliberate choice with is with Ben is thinking about like the people that you spend the most time with, you know, the handful of those people, you end up becoming sort of like the, the average of those people. And that's not an original idea to me, I don't know where I heard it, but just thinking about what a solid person Bob is and what a great person Ben is and thinking about that like this is hopefully going to be a many, many years process and having Ben rub off on me, uh, and having him like, uh, like learning from him and working with him is just something I'm super, super excited about.

Um, that is great. And so that you're talking there about sort of the personhood, the humanity of these two people, the character of these two people, which is amazing. When you— especially when you think, because Bob you've had kind of a long journey with— when you think about first becoming co-founders with Bob, either at RJ Metrics, or again, there's an opportunity at Stitch. Did you do anything formal to kind of align your values and your vision as co-founders? Like, I recommend in my book From Startup to Grownup doing a co-founder prenup, like the idea that it's not really an agreement as much as it's a set of questions that you can ask each other and keep revisiting as you go forward to stay aligned. Did you do anything like that?

Uh, so the short answer is, uh, with Bob, no, and with Ben, yes. This is another case where I think I got really lucky, uh, before and tried to be a deliberate about it now. And both cases, it's working out great. Whereas, you know, I think we figured out a lot of that stuff as we went along with Bob and was fortunate that, you know, we ended up being really aligned. Um, whereas, uh, with Ben, I remember, you know, I went on a, a walk with him to talk about this idea and him doing this and, and, you know, what it would mean to do it together. And then the next day, he sent me this huge email with a bunch of questions.

Oh wow.

Yeah, it was great. Uh, and some of the questions I was like, oh wow, that is a great question. I hadn't thought about that. And it was, it was a lot about what we want out of the company, what we want out of each other. Uh, and it was a really useful process for us to go back and forth on it, just thinking about like, what are the expectations we set with each other? What does success look like? Um, what is the kind of team we want to build and the company we want to build? Uh, and all that Uh, was really helpful. Uh, and again, I, I'm not sure how much of it it changed our mind on, but I think it, it more like uncovered things we hadn't thought about and just was increased underlining and bolding the fact that this seemed like a really good idea for the two of us.

So it was confirming in this case. Do you think there would have been any deal breakers or any kind of red lights or warning signs through going through that process and talking about those things?

I think maybe with someone else there might have been, um, you know, like I, there wasn't anything with me and Ben where it was like, uh, you want X and I want Y and I'm not going to give and I need you to cave on it. Like there was nothing like that. Uh, it was more like, hey, what do you want from me in this situation? And I was like, oh wow, that's great. I never thought about that situation.

Like what, like what situation? Can you remember?

Yeah, one thing was like, uh, a location. It was like he was, you know, pointing out that he didn't want to move. And he knows that, you know, some companies, it's important to relocate to the Bay Area. And, you know, he was also talking about the timeline. He's got kids and he's like, you know, for at least this long, I want to be in this area and this is important to me. And after that, I'm, you know, more open to it. And I was like, it just wasn't on my radar that I would ever ask him to move or I would ever ask anyone to move because I was already thinking about this company as a distributed thing. And that was another thing that, you know, we talked about is like, what does it mean to be distributed? How do we, how do we work that way? Um, but yeah, just that example of location where it was something that was obviously really important to him and I just kind of assumed it would be fine. And so I'm glad that we got on the same page about it. Um, but it wasn't like it ultimately, we discovered that we were on the same page rather than had to align.

Yeah, I got it. But it was helpful to probably have those conversations.

Totally.

You know, you just mentioned distributed environment. So, um, I am curious, I know that Common Paper is still new to this world. Yes. And, you know, we've just come out of the pandemic. And so I think people are all rethinking the notion of distributed workspace and hybrid and all those things. What early impressions do you have about distributed work the way you're doing it?

Yeah, it's a good question. And you're right, it's still early days. The short answer is that my impression so far are that the trade-offs are worth it. There's definitely pluses and minuses compared to being all co-located in the same place, uh, and I think probably the biggest plus of the distributed model is just a much, uh, bigger universe of people to recruit. And that's been really important as we've been, you know, bringing on, uh, the first people and starting to branch out. Uh, the— there's also certain kinds of collaboration that are really great in the distributed model. Uh, you know, we're, we're really trying to put an emphasis on written asynchronous stuff, which makes sure that everybody has a voice, uh, and someone who's maybe not as comfortable speaking up in a meeting can still have their voice heard, uh, still make sure that we're getting all the different viewpoints and getting to the best outcome. Uh, but there's also certain things that are worse. There's certain things that, like, just the random conversations that don't happen where you need to put a lot more effort into it. Uh, and Ben actually called this out the other day where there was one thing in a meeting where we got pretty far and realized that we had been operating with different assumptions for a while. Um, and he said, oh, you know, I bet this is something where if we were in the same office every day, this would have came up really early and we would have figured it out. Uh, where it's only since we have these like more prescribed scoped interactions now, you know, those random conversations aren't happening. Uh, and so I think it's something that we need to be mindful of. Uh, and so that's one example. The other one, which I'm really thinking a lot about, uh, and is about to become much more important, um, is just the, the trust and rapport building, uh, where the first couple people that we hired are all people that we've worked with before. Uh, and so there is that base level of trust, base level of rapport and understanding. Uh, and this coming week, actually we have our first person starting, uh, who is not someone that we worked with before.

Uh, we don't know him, a stranger.

He's a stranger and, uh, he seems great and, you know, absolutely, you know, knocked everything in the interview out of the park and I'm really excited for him. Uh, but this is going to be a somewhat different challenge because, uh, he doesn't have that shared background and history and, and embedded trust and we need to think about how to build that. And so we want to be really deliberate about, you know, making sure he feels included, making sure that we can trust him and he can trust us, and just having those like non-task-oriented collaboration and conversations where we build that up intentionally.

Right. That's great. That's great, Jake. And it's definitely a challenge, but as you said, it has pros and cons, including the idea of actually in some ways being a more inclusive work environment because it can, you know, people don't have to always just jump into meetings. There can be a lot more written. And to your point about asynchronous communication, You know, people who are in an office together can be less disciplined about documenting things, and when you're remote, you don't have that luxury. So it actually makes for a better sort of systemic running of the business.

I think that's a great point. And I, uh, was reading something about like at very large companies, like if you're at Google, like you're not going to meet every other person at Google for in-person meetings, even if they're like on another building on the same campus. And so like they're kind of quasi-distributed anyway. So I think it's just more of a question of when you focus on it and how. And I'm, I'm really excited about developing the practices and the, the, the rituals and the, the methodology that enables us to do it at potentially any scale, although I'm sure it's going to have to evolve and change a lot.

Right, right. That's great. That's fantastic. So when we think about the people around you, what I'm always interested in is how CEOs think about and approach complicated conversations, difficult conversations, delicate conversations. How do you think about approaching them with your employees and executives? Like, what are some examples of the most awkward or challenging conversations? And then how do you approach them? Are there scripts or tools that you find effective?

Oh, sure. Yeah. Uh, and one thing I'll say is that I know that I am much better at written feedback than verbal feedback. And so when I have, you know, some constructive criticism to give or potentially a tough conversation, I will absolutely script it out, uh, and often rehearse it one or two times.

Oh, great.

Yeah, yeah. Think about like, okay, how is this gonna, gonna go? Uh, it doesn't always go great, but, uh, you know, it definitely is, is a challenge that I, I try to make.

Wait, Jake, I'm gonna interrupt you for one second. When you say you script it out, and I tell everybody to script it out, And you can only script out your, your part of that.

True.

Right? So, but what do you, what do you, how do you sort of do it even though you can only script out your part?

So what I'll do is think about like, okay, what is, what is the most important one or two things that I want this person to do as a result? And it's not even, it's often not necessarily like what do I want them to take away? It's like, what do I want the behavior change to be? Because it's, It might, you know, it's great if we agree on everything, but like, if we're getting to a situation where there's a problem, then it may just be that the challenge may be a different interpretation and understanding, or it may be like, I need you to disagree and commit. Like, yes, I understand, but you know, this is, this is the way this works here. So I think some of it is really just thinking about, okay, what is the actual outcome that I want?. And then I try to have at least one, hopefully two or three, examples of the specific thing I'm talking about. Because there have been many times where I've said, "Here's a challenge and I want you to do this differently," and the person didn't know what I was talking about and asked me for an example. And I was like, "Well, that is a very reasonable question." That's right.

Go!

Yeah. Which really, you know, and then that really muddles the thing. So trying to have an example or two. Uh, and then, you know, thinking— putting it in the context also of, uh, like not essentializing it. Like, it's not that you are a bad person because of X. There is this behavior which is unproductive, and I would like this different behavior. And also giving, giving the why as to like, yes, it may be locally good for you to do that, but think about these 7 other people and the impact on them. And like, we're not trying to optimize for you, we are trying to optimize for the company and the customers and all these other things. Um, so those are like the elements. And for, for certain, um, for certain like conversations, I might have like a blog post or a model that I could go back to. Um, but in general, that's kind of the framework of thinking about like, what do I want to get out of it? What are the examples? And then like, what is the important thing around how to deliver it? And like, how are they potentially going to feel hearing this?

Yeah, that's very wise. I don't want to put you on the spot, but like, are there some examples, just anonymous examples, you can sort of share with us just to give an an example of when you've had a difficult or delicate, uh, either feedback conversation or other kind of conversation?

Sure. Um, there, uh, here's, here's an example of someone who, uh, when we made the switch, you know, when COVID happened, uh, and they had a lot going on at home, uh, they had a very demanding job, and in meetings they were giving the nonverbal signals that the meeting was not important. Oh, and like what? Like just not, you know, always typing during the meetings, not looking directly at people in the eye, uh, you know, chiming in like super intensive— intensively, like in 2 minutes, and then being silent for the rest of the meeting. Uh, and I basically had a conversation with them just saying like, I know you've got a lot going on. And maybe we should talk about, uh, you know, just, you know, you either not attending some of these— like, I'd rather have you not there, uh, or just, you know, at a smaller number of things and really dialed in. Uh, and, you know, it's— it was a very odd situation because of the pandemic, because they were at home, they, you know, they've got kids running around and everything. And like, so I tried to again talk about like the specific behaviors that I wanted to change, just like You looking right into the camera. I also like, they might've had a monitor set up that made them look like they weren't paying attention, but they are paying attention. And I was like, you know, I could just hear you typing. And I think other people are thinking like, we're in this meeting. I don't think he's taking notes.

That's right.

Uh, and so just like these handful of behaviors that like I wanted to see, uh, like looking straight at it, not typing, uh, trying to actively listen for the whole thing. Yeah, you know, not look away and then like be really dialed in and say like, hey, I disagree with this thing because like there's obviously a difference between the part you're engaged with and the part that you're not. And just like also expressing understanding that like, I get it, this is like a really hard time. And so there's whatever X meetings a week that you're in. Can we dial that back to X divided by 2 and you just be totally in and dialed in for those meetings? And I think he received it well. And, you know, it was, it was, uh, not something that had been a problem when we were in person. And so I think it would— that was like a relatively easier case because it was just like there was an obvious, uh, catalyst. Yeah. Um, and, you know, it wasn't like he was the absolute best meeting attendee in the world after that, but it was significantly better.

Yeah. So it was— it sort of had the desired effect.

It did, yes.

Yeah, yeah, that's great. So let me switch gears a little bit to talk about culture because you have RJ Metrics, and then we have Stitch, and now we have Common Paper. So I'm saying to myself, my goodness, you've had a lot of opportunity to start a company and think about culture, or not, and to watch culture evolve or intentionally evolve the culture, or not, as you go. I'm curious, what have been some of your early experiences with thinking about building culture, and how do you think about that right now?

Sure. Uh, it was something that was not on my radar at first. Uh, I, I remember hearing a lot about culture and that was important and just not knowing what to do about it. It was like, yeah, culture is important. I was like, okay. Like, I, and I, and then I just eventually thought that maybe it's just being a good person. Like, don't be mean. Right. Uh, don't, uh, Yeah, don't like fire people for no reason, you know, and that was my— the next iteration of my understanding of culture. And then one of the things which I ultimately learned was a big problem with the culture at RJ Metrics, and I tried very hard to change at Stitch, and I think we were successful, uh, and that, you know, it has not been an issue at all with Common Paper, uh, is that, um, the, the way that we gave feedback, and like, I think, uh, at Stitch we were very much a culture of feedback, and that was helpful. Where at RJ Metrics it was really not great. And insofar as where one person would come to me and say they had a problem with another person. So Jane tells me that she has a problem with Sally, and I thought it was very important to be empathetic and to listen and say, "Oh, that's really tough. I'm sorry you have to deal with that." Maybe I would give some suggestions on how to deal with Sally, and that was it. And I figured, my job is to be, uh, you know, uh, the ear and the shoulder for this person. And this, uh, was maybe part of the right thing but led to just a really festering problem, uh, where like these two people did not directly work out their problems and it was just them coming to me and complaining about the, the other people, uh. And what I eventually learned to do and the, the culture that I wanted to create was that, uh, the only option is to have a direct, uh, conversation with the other person. And there were variations in how to do that. And, and this is— I'll give the caveat that, like, if the problem is, like, sexual harassment or something like that, then that's— this does not apply. But for the vast majority of, like, day-to-day workplace things, uh, if Jane comes to me and says Sally is, uh, you know, doing this thing wrong, I'll listen, I'll maybe ask some questions, I'll say, okay, uh, would you like to have a one-on-one conversation with Sally, or would you like me in the room? Um, and there's just like, those, those are the only two options here. And then like, you know, what do you think is important to get out of that? And immediately drive towards, this is something we have to work out. And like, it is obvious to all of us that we work this out. Uh, and that sort of feedback is something we tried to bake into the evaluation process where we included 360 reviews., where we had regular— and it was all written and there was this cadence and like we had little review parties where the day it was due, people hung out in the kitchen and we got, you know, food and like it just tried to make it something where like this is a recurring ritual of giving feedback to each other. Wow. That is just like part of our job.

Yeah.

Uh, and everyone knew to expect it and like people got feedback on whether or not they were not giving good enough feedback. Like if you just said, oh, this person is great. And you said that like, like Yeah, they are great, but you're doing them a disservice around not giving them the feedback. And so I think it's one thing to say we're about feedback, but to assign tasks and to, you know, say this is in deadlines and really make it a core part of the thing. And then just one other example of this, trying to create a culture of feedback. I was incredibly grateful that over time people were, became comfortable with giving me feedback in like public settings. And I tried to celebrate and say thank you every time I got it. Where like, I remember I introduced something at an all-hands meeting. Our head of product, a guy named Mark Franz, you know, raised his hand and said, I see you introducing this and it's maybe a good idea, but like, I feel like this is something that it would have— it's kind of a missed opportunity that we weren't all brought in on this and it like made it part of like a decision process. And like, it totally threw me back on my heels and I was like, that is a great point, you know, thank you very much for raising that. And just, you know, kind of publicly celebrating him for giving me feedback, I think enabled everyone else to see that this is a good thing to do. And it's not just to me, it's not just from me, but from and to everybody on the team.

Yeah.

Wow.

That is a very powerful CEO moment where you sort of showcase to everybody, hey everybody, feedback is good, not bad, even to me. That's amazing, Jake. But I got to rewind the tape a little bit. Feedback parties? What? Can you tell us about the feedback parties?

I, I think our— and that's maybe some, uh, creative branding, uh, where, um, we use a tool called Small Improvements. And I'm sure there's a bunch of other things you could use where it's where we kept track of our one-on-ones, where we kept track of our like written feedback, uh, once a quarter, where the manager, uh, you know, gives feedback to, uh, the, the team member. The team member self-assesses, and then we assign out, you know, some representative people that they work with for a 360. Feedback, uh, you know, from different teams and whatnot. And, uh, every cycle, uh, Sam, our head of people, she would set deadlines and say, you know, this needs to be done here, this needs to be done there. And invariably, you know, everyone's busy, uh, they'll, you know, wait until like the day before the deadline and they say, oh crap, I've got whatever, 4 people that I need to give feedback to. And it's not something that you could just do in 3 minutes. Like, this is like, we really want you to think about it and like write something out and be specific. And so this was like at first totally spontaneous, and then I think eventually encouraged, was that, you know, we had this big kitchen with a lot of food and snacks, and people would like just start like the day before it was due working on their feedback there. And then, you know, we made sure there was beer, we made sure there were— there was, you know, particularly good food. And it became kind of just like a recurring thing that once a quarter you knew that you could— you know, it's not a collaborative activity, but there's some amount of camaraderie and maybe you know, nice being around your coworkers as you're doing this thing, which you know is important, maybe not the most fun thing in the world.

Yeah, totally. I love that so much. That's so great. You know, I tell my clients all the time to have homework parties, right? Which is just like you're saying, like, it's an individual task, but go do it with 5, 6, 7 people and do it in a celebratory way with like food and whatever. Because you have to allocate the time one way or the other. And the idea of coworking is actually like, actually just makes everything more fun.

I completely, completely agree.

Yeah, that's a great ritual. So let me talk to you about your leadership style. So again, you've had all these different experiences from, you know, little baby startup to mature startup to different, um, exit events. How do you think that your leadership style has changed, uh, over time since, you know, through all these experiences?

I would say that Well, one thing that has changed a lot is just my understanding of the importance of delegating. And like, hand in hand with that is training. Like, this is another thing, and I may be a broken record on stuff like this, but like, I was so naive and just like fundamentally bad at the concept of training when we got started. And I remember the first person that I started working with at RJ Metrics who we brought in to help me. I was doing all like the new client implementations and I think I'm lucky that we, you know, got one of my friends to come part-time and help with implementations. And it's good that he was my friend because anyone else would have quit. That's right. And I would just get so frustrated with him saying like, why aren't you doing this better? You know, like, why? You're supposed to be helping me out with this. It's taking 10 times as long now, right? Like, why don't you get this? 'And he fortunately pushed back on me and like said, like, you know, this is just some product that you guys made. Nobody else in the world knows how to do this.' Uh, and I was like, 'Oh, that is a very good point. Yeah, of course you don't know how to do this.' Uh, and you know, he figured it out, and he, together with him and other people that we brought on board, started to have more of like a formal training process. And then ultimately, like, now, uh, at Common Paper we have like, here are all the things that we want to get done before the person starts. Here's all the things we want to get done in their first week. Here's all the things we want to get done in the first 2 months.

What are some of those things? What are some of those things, Jake?

So yeah, sure. Some of the, like, you know, before they start, it's a lot of box-checking things like HR compliance, sign their NDA, stuff like that. Uh, in the first week, uh, you know, for the, the engineer that's about to start, you know, uh, their first day, hopefully they are going to ship some code in some form. Maybe it's just typo correction, but all the way into production. There's also things around having one-on-ones with different members of the team, watching customer testimonials of other people in our industry. You need to develop context on what the landscape of competitive and complementary tools are out there. And so this is a 20-minute video, it's a webinar, and you got to watch that. Um, there's also stuff like we have this, uh, like goofy tradition where the first Wednesday of every month everybody wears a whale t-shirt, uh, and it's Whale Wednesday.

Whale Wednesday, folks, you heard it here first.

This is the most important thing for a startup. If you're not doing this, you're doomed to failure. And so like in their first week, one of the tasks is buy a Whale Wednesday compliant t-shirt, and then in the first 2 months it's like make sure to wear your Whale Wednesday on the first shirt, and then it's just something to like show off on Zoom and talk about with other people. And did you get it on Etsy, or did you get it on Threadless, or whatever? Uh, and it's just something where like trying to ingrain the habits and rituals— and some of it is like very task-specific, some of it is just knowing stuff, some of it is getting to know people. Um, and it's really not so important what's on the list when you first make it. It's that you revisit that after the next person starts and thinks, oh, You know, what, what should they have known? What, what did they get, uh, have a roadblock because we didn't buy their computer soon enough? Or we, um, you know, they had a really hard time working on this first project because they didn't know this. And how would they know this? It's only because we told them to read this or watch this or things like that.

Yeah. Oh, that's great. How did I just have to ask, how did, how did you come up with Whale Wednesdays?

Uh, Ben is the one who deserves the credit for it. And so he previously was an engineering leader at Betterment. And that is a tradition that his team at Betterment has. And I actually don't know, uh, uh, how or why that came to be. Uh, but as soon as he mentioned this to me, I was like, oh yes, absolutely. That is entirely in line with, uh, the goofy sort of thing that works well over Zoom. Uh, that, uh, it's perfect for us.

Oh, that's amazing. You know, I interviewed Jon Stein, um, the president, the founder of Betterment. Do you know John?

I don't.

Same last name, unrelated?

Yes, a very good last name.

Very good last name.

I am a Betterment customer. Yeah.

Oh, good, good. John was very— what I loved about John and talking to him is that he actually said to me, "In some ways, I feel like I started Betterment so that I could develop company culture." You know, he's very into culture. He's very into rituals. He's very into camaraderie among the team. So amazing to hear that sort of being populated now and sent out to the world through his team. I think he'll be very gratified to hear that.

Yes. And I'm assuming that this is the part of the culture that he was most into.

The whales.

And most wants to spread out into the world.

That's all we talked— my book, that's all we talked about, whales.

That's great. That's great.

Now, Jake, how do you think about— there's a lot of people around you giving advice. Again, you've dealt with boards and you've got other folks and certainly then you got acquired. So then you had other people giving you advice. Advice. When do you think about taking the advice, and when do you think about discarding it since you know your business best? Like, how do you draw that line between being open and also being, like, focused?

Yeah, this is— it's tricky, uh, and there are definitely cases where, especially early on, where I took things that the board said as, like, mandatory instructions, and in hindsight they would have been much more productively taken as, here is an idea. Right. And is there an example? Sure. I think, you know, some of the things were around the way and volume of people that we hired on our sales team at RJ Metrics. And this is something that ultimately led to, you know, I would say my biggest professional mistake, which was the lead-up to— we had a layoff at RJ. And, you know, we ended up laying off about 25% of our team. And it was super hard. And I mean, it was much harder for the people impacted by it. But it was, you know, definitely the worst day of my professional life. And there were a bunch of things around basically what was working at one of our board members' other portfolio companies, actually several of their portfolio companies. They had companies that were more successful than us.. And there were certain tactics and certain like, uh, guidelines that they were using and they were just generally hiring faster than us. And we were just, you know, first-time entrepreneurs out here in Philly where like we just figured that those people that were doing better than us were doing something right.

Right.

In reality, they were doing a lot of things right. Uh, but you know, that combined with some, uh, unfortunate interpretation of some data that made us think things were going better than they were. And yeah, led us to eventually, you know, hire faster and hire faster and hire faster and then realize, oh no, this model isn't working. And then, you know, given that we were there, the, the layoff was the only thing to do to save the company. But, you know, really, really unfortunate that we got ourselves into that situation in the first place.

Yeah.

And I'd say just like the, the broader like rubric for when to take the advice versus when to just, you know, take it as an idea. I would say some of it is around, you know, what problems are actually solved problems and what things are, you know, the actual place where we're supposed to be applying our vision. Um, because, you know, there's some things like, I feel like you really only get a handful of things that you should do truly original and different in a company. Like, if you're innovating on everything, you're going to get a lot of stuff wrong. And so you might have a vision for the market or your product or what your customer needs, or maybe that there's some new customer that didn't buy before but it's going to start now. Uh, but like, we're not also innovating on our PTO policy or our, you know, um, you know, our sales comp or something like that. Like, there are some things where, uh, you know, there have been many experiments, there are a handful of things that work, and we're just going to follow the best practice for that. So when we get a piece of advice like, hey, you're doing this really basic thing that every company does and you're doing it wrong, or you're not moving to the next level, that is something I try to pay very close attention to. Uh, but if it's like, I think your target customer wants X, and I think to myself, well, like, I've had 100 conversations with our target customers, how many have you had? Right. Uh, or, or like, my core thing in starting this company is that I think this target customer want something different than what they're getting. And so that, you know, is a case where it's much more like, I hear you, thank you for the feedback, I'm going to stick with my way of doing it. And they're obviously not all black and white, but I think that's at least one rubric we use to try to think about like, what is, um, yeah, when to follow the advice and when to stick with our instincts.

Yeah, that's great. It also feels like it's like when you know you have an earned secret, like you've done the work Yes.

Yeah, that's a great point. Yeah. And like, there's a lot of cases where someone says, I just don't think people will do that. And I was like, oh, actually, I know 20 people who did that.

Right. Yeah. Right. Okay. That's great. So you talked about one of the tough setbacks you had when you had to lay off 25% of your workforce. Would you say that's your toughest setback, or is there another setback you could talk about? Because I'd love to hear how you kind of dealt with a really bad setback and what you learned from it.

Sure, uh, I'd say that, that one was certainly very tough. The other one that comes to mind is, um, we had a customer, uh, not like the super early days, but like probably maybe midway through our journey at RJ Metrics, where, uh, they were a great customer and my sense of self-worth was very, very tied up in them. Like, I had sourced the lead, sold them, implemented them, supported them, had the relationship upsold them to like a 3x bigger deal. And then the CEO ended up investing in us. And it was just like, you know, the case study was the top thing on the front of our homepage. It was just like, amazing. And I felt a lot of pride in it.

Yeah.

And then a little while later, you know, a couple years later, I, you know, wasn't as close to it. And then a member of my team told me that that customer was churning. And I was, uh, incredibly bummed out about that and felt like I had not, you know, nurtured this thing that was like such a pivotal, pivotal thing for the company. And, you know, I scrambled and tried to save it and completely failed and just, uh, was feeling really down on myself. And also like we had had like a spike in churn in general around this time, so it was like like not just the one, it was like a problem that was on my radar and then hit really, really close to home in the worst way. Uh, and I remember walking home from work that day just like incredibly, incredibly bummed. Uh, and then, uh, some guy on the street who, uh, I, you know, I didn't know and looked like he might be, you know, experiencing mental illness or homelessness, uh, but just got right in my face and pointed his finger like right against my nose and said, hey, fuck you, man. And I was just like shocked and like burst into tears and didn't know what was going on. I was just like standing there for a few minutes. I was like, I don't— I don't like who everyone— it feels like it's coming at me from every direction. And then like I went home and I calmed down and like it reminded me that like while this was a really rough day at work, like, I have a home to come home to with a roof and an AC and a heater. And like, I can have dinner this night and have as much as I need. And then I go back to work the next day and work with a bunch of people I really like. And so like, while it was the case that this was a really rough day and not one that I wanted to repeat, there were so many other things to be grateful for. That, that is, is something I go back to a lot and just try to remember all those other things that, that I've got going.

Yeah. Yeah. Very powerful to have that kind of perspective, you know, and just back to also like there are ups and downs in the journey and you have to kind of realize that and come to terms with it. Right.

Yeah. And, and just having, having more of everything helps a little bit because like when you, when you start out and it's just, there is one customer or there is one investor and it's either like, they say yes or no, and it's either you're top of the world or, you know, the bottom of the ocean. Uh, having more of those data points just helps you be less moved by any of those one things.

Right, right. Totally. So let's move on to the acquisition of Stitch. So I'll just— again, I want to focus on that because that's when you and I knew each other. And, you know, frankly, that was a pretty good outcome for you, like pretty darn good. And I'm, I'm just wondering, you know, it's sort of the founder's dream to build up something of value and then somehow or other either get acquired or go IPO or something to sort of determine the marker of success. But I have to also think that even for, for actually for both of the startups that you sold, there has to be some feeling of letting go of your baby. So I'm just curious if you can talk about that, um, from your point of view.

Sure. Yeah, it's having the company get acquired. There are a ton of things that were great about it. And I'm really grateful that we had a great outcome. And the folks at like Talend that, that acquired us were really lucky. You know, I've heard a lot of horror stories about companies getting acquired. And, you know, our experience was just so much better than so many of the other people that I've heard about. Uh, there were definitely some challenges though, uh, and challenges around just like as simple as things like I used to have the final say on stuff and then I didn't have the final say on stuff anymore. And also just, you know, having both the implied and in some cases real responsibility for the outcomes but not the authority to make, uh, all the decisions, uh, and just trying to optimize for this greater whole that was not the thing that I originally signed up for working with. And, and again, just navigating like, you know, a, uh, 1,000-person-plus org going from a, you know, 30 or 40-person org, just a lot of challenges. And things as simple as like what we call the product and do we change the brand name, uh, were very, very challenging, uh, all the way to like what is our strategic vision for this company and team and product and office full of people in Philly? Uh, and so yeah, it was definitely— yeah, it was a big learning experience, and, uh, parts of it were rough for sure.

Yeah, yeah. Um, how did you kind of come to terms with it?

I think, you know, and this is something that you helped me out with tremendously, but like understanding that this was all what aspects of the cohesive whole and like the, the part of the journey that I had already been on, and I continued to be on, where like, any individual thing in isolation might seem unfair, or might seem bad. But like, that these things really can't be disaggregated. It's like really happy about selling the company, really annoyed that they might want to change the name of, of the product. Like, those are, those are, those are the same thing. Uh, those are not, uh, two different things. Uh, and then also thinking about this as like, oh sure, maybe I'm annoyed dealing with this person who doesn't want us to do things the way that we want to do. Um, but maybe it would be kind of fun to learn how to like influence people in an org. And maybe, like, maybe this is not something that's so alien and different than working with one of the team members that I've worked with for years. Like, maybe this is— I can leverage some of the same skills, or I can learn something new. Um, and just, I think, just changing my mindset a little bit. And, you know, ultimately I did decide that it wasn't somewhere I wanted to be long term, and I ended up leaving. And like that was always a question mark of— I never worked at like a much, much larger company before, and so did I want to pursue that path? And it kind of helped me understand that no, I do really want to stick at that much earlier phase. Um, so yeah, I thought about it as almost like this is a period of, of learning and experimentation, a lot like the, the period of the very early stages of a startup is a period of learning and experimentation.. And maybe your first product doesn't work perfectly, and maybe, uh, you know, this time integrating the startup doesn't work perfectly, but both of those are potentially okay.

Yeah, yeah, amazing, Jake. That's so helpful and quite astute. Um, so just a few more questions for you. What do you wish you'd known earlier on your journey?

Honestly, that the thing that comes to mind is I wish I knew about meditation and cognitive behavioral therapy for insomnia. Those are the things that like the, uh, have been most helpful for like me, you know, managing my, um, psychology and like insomnia from stress and whatever. Those are— if I could go back to like my 20 or 23-year-old self and give me any advice, I would like point myself to those two things.

That's— yes, that's so wise. Managing yourself or managing your own psychology is so— it's like unsung. Nobody talks about it. It, but it's like so important, right? Yeah, yeah, totally. So is that— does that align with advice you have for other founders? Do you have other advice for other founders as they embark on their journey to grow into leaders?

Well, uh, so yes, I do, uh, suggest that to other founders when— whenever I can. Uh, you know, I'll give meditation.

Meditation.

Yeah, just do it. Go, go, go do it. Uh, there's also like, um, a more like business-focused set of advice that I might give myself in the past, and that also might be useful. And probably the key one is thinking about the phases of a startup as more discrete rather than continuous, where, um, like, I, I think early in my journey it was about like, okay, how do we make the product a little bit better? How do we get like one more customer? And that is like very useful things to focus on. And a lot of our time was correctly spent on that. But especially in the, in the RJ Metrics journey, I think we were too focused on that kind of incremental progress, and not focused enough on like, okay, we've got 10 customers, how are we going to get 1,000? And I think if we had stepped back and thought like, what is our strategy going to be? Like, what do we need to do like qualitatively differently. I think that could have led to a better outcome with less bumps. And, you know, it's tough to know with the counterfactual. It's definitely something that we did a somewhat better job of at Stitch and that we were trying to do at Common Paper. We're just really thinking about, like, the first phase is making sure that anybody wants the thing that you're making. The second phase is like, okay, can you, like, prove that you're adding some value? And then maybe the third phase is, okay, how do you scale it up? And those phases might look differently for consumer versus B2B or software versus hardware or whatever, um, but really thinking in advance about what are those phases and then when do we switch. Because the things that you need to do on day one are often significantly different than the things that it makes sense to do once you've proved the first thing and need to switch into the second thing, right?

So being more specific and sort of granular about those different stages and what you should be doing inside of those different stages.

Right. Yeah. And then, yeah, just realizing that our success criteria should change.

Yeah. Oh, that's great. Right. So how you determine success should change. That's great.

Yeah.

Jake, so awesome. So powerful. So insightful. Is there anything else that you want to share?

I would say thank you. Thank you because for a lot of this journey, I mean, the thing that may not have been obvious, but a lot of these lessons learned were through your help, or at least, you know, you helped me get somewhere that maybe I would have gotten to, maybe I wouldn't have gotten to, but got there a lot faster and got there in a more enjoyable and educated way. So yeah, I would say thank you so much for helping me get to, to where I am today, and hopefully somewhere better that I'll get to later.

Ah, Jake, that is so rewarding to hear. Thank you so much. And such a joy to have worked with you. And it's so— it's such a joy to see you thriving now. And I I just want to say thank you for being on this podcast as an early guest and for sharing your wisdom, which I know will be very, very valuable to other founders. So, thank you, Jake. It was great to see you.

Thank you. Likewise. So much fun.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.