#93 – Evolving roles as the company grows (Ben Grynol & Mike DiDonato)

If there’s one thing that’s true about growth and change in a startup, it’s that it’s constant. Mike DiDonato was one of the first hires outside of the core team in the earliest days of Levels. He’s seen the company go from a handful of employees to 50 and all of the iterations that have happened along the way. Mike sat down with Levels Head of Growth Ben Grynol to talk about how the key to growing along with a startup is to replace yourself regularly, how early days can feel like quicksand, and how imposter syndrome happens to everyone.

11:43 – A scrappy way to get things done

In the early days of Levels, Mike and Josh had to take care of major product issues themselves.

I remember Josh had, we were at a WeWork and he’s like, “Hey, I just got a shipment of 500 covers to my house. There’s an issue.” I’m like, “What?” He’s like, “There’s no adhesive.” So we had to, I remember, going back to his house, and there was just this massive bag of these black silicone covers. And then I don’t know if it was 3M or some kind of double-sided adhesive. And so we had to peel the one part without damaging the other side. You had to be really delicate. I mean, remember, it was 500 of these. And at the time it was 10:00 at night, and sitting on the floor, and we’re just doing it. I think Josh probably wanted to hit me over the head with the hammer because I tell everyone, I failed arts and crafts when I was in grade school, I was not good with those things. And I’m like, “Am I doing this right?” And he’s like, “Yeah.” And meanwhile, I think Josh had to edit, or correct almost every one that I did. And it definitely wasn’t scalable for sure, but it was really important. It was something we promised people that we would get this, it was a scrappy way to get that done.

17:00 – Give your job away as you scale

Growth in a startup means that you seek to replace yourself as things scale up. It’s counterintuitive to how many other industries work.

One of the things that really stuck out to me, was I think there’s a quote. “If you want to grow as fast as your company, you have to give away your job every couple months.” And I was like, “What?” Now it’s not the first time that I heard this, because Sam said to me and has, he was like, “Always seek to replace yourself.” And I can’t speak for other tech companies. I know Google says this a lot, but I don’t know if every company believes it, but it’s really foreign as opposed to other industries. I was coming at it from this finance banking perspective, like, “What? Replace myself, wouldn’t that be putting myself out of a job?” And I was like, “Give a deal away? That doesn’t make any sense.” But it comes back to with, I think, you may have said this to me. Everything, almost everything about scaling is counterintuitive.

22:16 – Bringing on new people means you can do more

Mike said that before they hired anyone else on his team, he started feeling like he was sinking in quicksand with all of the responsibilities piling up.

And leading up to that, I think it was pretty clear, although I could have done a much better job of voicing it, but it was starting to feel like quicksand, a feeling of quicksand. I just couldn’t get ahead. It was, for the longest time, before we had an app and before we had all of these members, it was like, “Hey, you need to manage the experience for a few hundred people. You need to surface feedback, or get product feedback for the product team, AKA David. And that’s what it is. And as you can take on new things, great.” But started taking on all of these things, so ops and product, and you can even say that what Sam and I were doing with the lead calls, it was in a sense almost like marketing. Whatever. And there was this shift, and there was all these things on my plate. And once Miz came in, it was helpful A, to make me feel better.

27:52 – Responsibility not to fail

The heaviest weight was the responsibility to the rest of the team and the members.

I just felt this immense responsibility that A, this for the first time, was my first experience working on something that just was so aligned with my values and my purpose. And I knew how important the work that we were doing, and all of these … It was basically the founders, and then me and John, and these people trusted me. And I was not going to let them down. And more importantly, it was not going to let our members down. These people that paid us this money and had these expectations.

28:31 – Don’t fail in silence

At Levels every experiment or challenge teaches us something and we need to communicate that.

I think what I was missing at times was the awareness that this was really going to happen. It was not a scalable thing that we were doing. But we have this thing at Levels, you can’t fail in silence. It’s okay, we run experiments all the time. Document it, take learnings from it. That’s amazing. That’s a win. But we just can’t fail in silence. I don’t want to say that I failed in silence, but I just didn’t know, was it okay for me to say, “Hey, I’m drowning?” And I eventually did get to that point. But it definitely wasn’t an ego that like, “This is who I am, and who it defines me.” It was more, “I have such the gratitude to be a part of this. And even more grateful that these put people have put their trust, and I’m not going to let them down.”

31:19 – Pitch in where you can

In a startup environment titles and ego can’t get in the way of getting things done and fulfilling your mission.

And even for you, when you first joined Levels, I mean, someone looking externally, that maybe doesn’t have, that isn’t playing the long game, would be like, “Oh, well, is he really doing something that the head of growth would be doing?” Because you were just focusing on these super important things like community, and all those different … And I was like, “No, that was really helpful for me to be a part of, and see that.” And it goes back to the idea that no one really cares. And Sam says this all the time, “It doesn’t matter who does what. What matters is that we get these things done, and we achieve our mission and really put a dent, and solve this metabolic health crisis.”

35:01 – Buckling under a heavy load

The overwhelm at the beginning came from a combination of new things to learn and the amount of things that needed to be juggled at once.

So coming back to quicksand, it was a lot of new things, but it was also just this shear load of things. I was still literally the only person managing the experience for everyone. We had an app at this time, but we had way more people using the product, and more and more responsibility was being put on me, to not only manage that, but also manage the ops, or general operations, in general. Because I think at that time one of the things we needed, is we needed to get Josh off of operations, so that he and Casey could focus more on podcasts and media, and all the amazing plan that Tom created. It was a conjunction, I’d say, it was a lot of foreign things, but it was also just managing everything.

39:32 – Growth and change are constant

Mike realized that growth and change weren’t temporary states. This was how it would be for as long as the company exists.

They’re all very foreign. Every one of them’s foreign, and one of the episodes that really hit home for me that we did, was the one with Braden. And he talked about Imposter Syndrome, and we all get that, especially when we try something new. But again a big thing for me that changed, was hearing from you. Like, “This is what we’re going to do. This is just how we’re going to do it.” And you’re like, “This isn’t going to be for a few months, this is going to be in perpetuity.” Even now you’ll still check in with me, and be like, “Hey, how are you feeling about growth, about the change?”

41:22 – There is no such thing as overcommunication

Nothing can go catastrophically wrong as long as everyone is always communicating with each other.

So first thing is, know where you are, make sure you’re with your people, say, you’re tribe, or the right place for this. If you’re at the right place, the first thing, communication, first thing is communication. There is no upper bound of communication. If there is, someone will tell you. But why I say that, is people have a problem, when they get caught off guard. If you’re communicating these things, whether it’s a process thing, or updates about a particular project, I’d say … That’s one of the biggest things that I’ve found, is as long as people are informed or in the loop, at least at Levels, there’s not really something that can go catastrophically wrong. That’s just more of a meta thing that I found working with this company.

43:19 – Build the mechanism

Think about what you want your role to look like in the future and then build the mechanisms that will replace you and allow you to step up into that role.

And as far as high level, replacing yourself, I think it’s important to know what kind of person do you ultimately want to be within the organization. Do you want to … You’re never going to be the head of, let’s take an arbitrary department, the head of customer support, if you’re answering every customer question. You’re never going to be the head of marketing, or the editorial director, if you’re writing every piece of content. Don’t be the mechanism, build the mechanism.

Mike DiDonato (00:00):

I think it’s important to know what kind of person do you ultimately want to be within the organization? You’re never going to be the head of, take an arbitrary department, the head of customer support if you’re answering every customer question. You’re never going to be the head of marketing, or the editorial director if you’re writing every piece of content. Don’t be the mechanism, build the mechanism.

Ben Grynol (00:45):

I’m Ben Grynol, part of the early startup team here at Levels. We’re building tech that helps people to understand their metabolic health. And this is your front row seat to everything we do. This is a whole new level.

Ben Grynol (00:58):

When Levels started in late June, June 25th, 2019, it was Josh Clemente, Sam Corcos, just two of them. Quickly, the team scaled to be David Flinner, Andrew Conner, and Casey Means. The five co-founders of Levels. Shortly after that, a sixth team member joined, that’s Mike DiDonato. Mike is one of the earliest team members of Levels. He has seen everything change. He has seen the product go from being what we called the Mike-bot, it was literally Mike texting with people back and forth to understand their data, and to give them insight about what was going on. All the way to where we are today.

Ben Grynol (01:50):

We still have a very long way to go, but a lot has changed. In February, while we’re at around 50 people now, that’s a big Delta from the six when Mike started only two years ago, and things will continue to evolve. So Mike has a very special lens on what it has been like to be part of the Levels team as we’ve scaled. He holds some of these stories near and dear to his heart. So Mike and I sat down, and we discussed the backstory, some of the history of Levels, things that might have been uncovered in other episodes, and new stories that haven’t surfaced before. It was a great conversation, here’s where we kick things off.

Ben Grynol (02:34):

We’ve talked a little bit about the backstory of Levels, and you have experienced, we’ve been talking so much about experience and lived experience, and shared experience, and all these things. But you have experienced Levels from its foundation. So you watch things change and evolve, and it’s basically a new company every six months. From the Mike-bot days, when you’re doing text messages, until where we’re at now. You’ve done almost every role, except for basically being an engineer.

Mike DiDonato (03:12):

They definitely, let me, before we jump in, they don’t want me in the code base. Engineers don’t want me there. Copy doesn’t want me there. Members definitely do not want me there. Things will be breaking fast, but yeah, sorry.

Ben Grynol (03:28):

You can learn. So let’s walk through some of these backstories. How have you seen things evolve and change?

Mike DiDonato (03:39):

Oh man. Well, we may have covered this in another pod, but I knew about Levels right before it was Levels. It was, what was it? What did we call it in the first few episodes? Maple Syrup? Maple Biometrics, right?

Ben Grynol (03:55):

You got it. Maple Biometrics.

Mike DiDonato (03:59):

As Kate called it, Maple Syrup. Yeah, so I actually remember, tell me if this is too early, but vividly, I remember when Sam and Josh got reconnected, do we think that’s too early?

Ben Grynol (04:18):

Never too early.

Mike DiDonato (04:20):

All right, cool.

Ben Grynol (04:21):

[Crosstalk 00:04:21] timeframe we’re talking in May of 2019.

Mike DiDonato (04:25):

Yeah, and Josh had introduced me to this idea a while ago, and we were jamming. I was still deep in this finance banking world. Then I remember this day vividly, because I was, I just got back from California in May of 2019. And it was my oldest niece’s Holy Communion. And I came back, and Josh came over, I forget for what reason. I don’t know, he was like, “Yo, things have changed.” And I was like, “What do you mean?” And he told me the story about Sam and going up to New York, and then obviously that epic juice cart story.

Mike DiDonato (05:10):

And I think my first reaction was like, “Well, who was this Sam guy? Who was this guy? Is he to be trusted?” And it turns out Sam’s one of the most genuine, and some of the most high integrity people I’ve ever met in my life. But told me that, obviously I super excited. I was super excited for a friend, and for the idea of what this company would be. I remember I was on the survey when they were trying to figure out a name for the new company. I was part of the email survey, and had voted for Levels. Then over the summer, was doing my own thing. And Josh and Sam mean, I think it was David joined first? Yeah. And then Andrew and Casey. I think I was actually the first, or one of the first customers in August.

Mike DiDonato (06:08):

No, it would’ve been September, beginning of September, 2019. I remember doing a call with David, a feedback call, and I was just like, “Ah, this is so interesting.” And I knew from afar that I’d wanted to be a part of this company in some fashion. And then David and I were talking, and I think I was training for a marathon, or half marathon. David’s like, “Oh, you should wear Levels, blah, blah, blah.” And then Josh and I were chatting about something unrelated. At this time I personally had left finance and banking, and was just thinking through what the next thing was, and got to November. And I remember Josh was like, “Hey,” it was one evening. It was like the first week of November, “What are you doing?”

Mike DiDonato (07:09):

And I was like, “Oh,” I think I just got done with a workout, and I was eating food. And he came over, and I’m going to really like botch the whole, but he’s like, “Yes, what are your plans?” And I’m like, “What do you mean?” He’s like, “Are you going to go back to the finance and banking thing?” I was like, “Oh no.” I was like, “That’s, I’m casting votes every day to never do that again, personally.” And he’s like, “Well, look, we could,” he’s like, “I think there’s a place for you here.” I don’t think he finished that sentence. And I was like, “Let’s go.” I don’t think I asked what it was. I don’t think I asked about compensation or anything. And he’s like, “Are you sure?” And I’m like, “Yes. And it was typical Levels fashion, I had …

Mike DiDonato (08:03):

He’s like, “All right, well, you have to read all these papers. You have to read this book.” And I had, my inbox was just full of different resources to get ramped up on. And from there, at that time, the member base was obviously much smaller than it was today. The product was quite different. At this point in time, there was no app, there was no branded Levels box. It was, people received a cardboard box with a month supply of continuous glucose monitors, and an email to schedule your onboarding call with, I think, at that time, it was primarily David. And what had happened, it got to the point where the reason David was doing what he was doing, is he was trying to understand what the needs were. So that, from the product perspective, he could think through, “Okay, what do we need to build?” And it got to the point where David had no more bandwidth, and he’s like, “All right, I need to go focus on product stuff, but we need somebody to, basically, manage this experience.”

Mike DiDonato (09:10):

And that was the David-bot, and the Mike-bot, it was literally I, the responsibilities there were, do onboarding calls, and check in, and debrief calls with everyone. And all throughout the process, since we didn’t have an app, we had a dedicated text message line, where the individuals using the product were just texting us screenshots, and some text. And we weren’t really clear what was data entry, versus what was a question. It was, Josh was like, “Yeah, you got this right?” And I was like, “Yeah, totally have this covered.”

Mike DiDonato (10:03):

And I remember one of the really fascinating parts from my perspective, before we get through the whole journey, is it’s so funny, some of the people that I interacted with were, externally, member-wise, so early, many of them ended up becoming investors, and our really excellent partners, and supporters of our mission. Which thinking about that now, it’s a pretty cool feeling, right? So much happens in what is it? Almost three-ish years, call it two and a half, between two and a half and three years. But that was the David- and Mike-bot days. And then I remember one quick story before we go any further. I think there’s a picture attached to this. We had, so we have our performance covers now. They look very different than what they looked like in 2019.

Mike DiDonato (11:13):

They were made of this silicone, hard silicone mold. And the, it was something about either the orders, or actually the vendor, there was an issue with the vendor so that the mold needed a way to stay on to your skin. So some kind of adhesive that was not going to interfere or cause any allergic response. And I remember Josh had, we were at a WeWork and he’s like, “Hey, I just got a shipment of 500 covers to my house. There’s an issue.” I’m like, “What?” He’s like, “There’s no adhesive.” So we had to, I remember, going back to his house, and there was just this massive bag of these black silicone covers. And then I don’t know if it was [3M 00:12:13], or some kind of double-sided adhesive.

Mike DiDonato (12:17):

And so we had to peel the one part without damaging the other side. You had to be really delicate. I mean, remember, it was 500 of these. And at the time I was, it was 10:00 at night, and sitting on the floor, and we’re just doing it. I think Josh probably wanted to hit me over the head with the hammer because I tell everyone, I failed arts and crafts when I was in grade school, I was not good with those things. And I’m like, “Am I doing this right?” And he’s like, “Yeah.” And meanwhile, I think Josh had to edit, or correct almost every one that I did. And it definitely wasn’t scalable for sure, but it was really important. It was something we promised people that we would get this, it was a scrappy way to get that done.

Mike DiDonato (13:09):

I know, I didn’t take the picture, josh did. He had the, it’s a pretty, I think you’ve seen it. I think you’ve said that it’s one of your favorite pictures. It’s just literally sitting on a concrete floor, and just surround it by covers. I think it was the dead of winner. It was just, looking back on that it, it wasn’t scalable, but it was definitely scrappy. At the end of the day, we didn’t stop until it was done, and everyone got what they were supposed to get.

Ben Grynol (13:41):

When you’re doing all these things, there’s something really fun about that. It’s very intimate to think back on some of these experiences. To think like, “Man, that was fun. We were sitting on …” As terrible as it can sound at the time, it’s also, you can look back on those things fondly, and you can take like, “Wow, it was a necessary step to take.” And so as the company evolves from sitting cross-legged on a cold concrete floor, cutting out adhesive, to where we are now. And we’re still so early, we’re working and working to get to a point where we are launched publicly. What has it felt like, if you’re being totally honest with yourself, what has it felt like going through all this? Is it comfortable? Is it exciting? Is it uncomfortable, or uncertain?

Ben Grynol (14:39):

What are some of the feelings that you have as the team grows, as the product changes, as things get harder? Your role changes, what you’re responsible for changes. This happens in some companies, people will do the same thing for years and years, without a lot of variation in what they’re doing. And in a startup, especially with the way you’ve experienced a startup, things are constantly evolving and going through that change can feel totally different to different people.

Mike DiDonato (15:14):

This is a great topic. And you must remind me before we stop, because there are a few company milestones that I do want to touch on. But this is, probably what you’re talking about here, is how rapidly things change. Especially as someone that’s never worked at an emerging growth company, right? My previous employer was a behemoth, hundreds of thousands of employees, and things started to really, I shouldn’t say that, things have been changing forever. We’ve gone through, we were remote pre-world pandemic, and obviously we’ve moved through this pandemic. But one of the best things that I think was shared with me, it’s something, one of the resources, that I’ll talk about in a second.

Mike DiDonato (16:10):

But Sam, I think all of this needs to be prefaced by, you need to make sure that you’re at the right place, that you’re with, your company has the culture that we have. I mean, everything’s not going to be the same exactly. But Sam says this all the time. He still says it to this day, every three to six months, “Hey Mike, it’s basically a new company.” And as we add people, things are going to continue to change. They’re going to, that’s what’s going to happen. I forget if it was Sam or Josh, somebody on the team had shared with me, I think it was from First Round Review, “Giving away your LEGOs.” And it was a very foreign term for me. One of the things that really stuck out to me, was I think there’s a quote. “If you want to grow as fast as your company. You have to give away your job every couple months.”

Mike DiDonato (17:16):

And I was like, “What?” Now it’s not the first time that I heard this, because Sam said to me and has, he was like, “Always seek to replace yourself.” And I can’t speak for other tech companies. I know Google says this a lot, but I don’t know if every company believes it, but it’s really foreign as opposed to other industries. I was coming at it from this finance banking perspective, like, “What? Replace myself, wouldn’t that be putting myself out of a job?” And I was like, “Give a deal away? That doesn’t make any sense.” But it comes back to with, I think, you may have said this to me. Everything, almost everything about scaling is counterintuitive. And when I was reading that piece from First Round Review, it was something like, “Oftentimes your initial response when someone new, or new people join us, is to take your LEGOs, grab them right away.”

Mike DiDonato (18:25):

And basically, micromanage in some way. But the real best way to manage like this, or navigate this scaling process, is to ignore those instincts, and have more of an abundance mindset. Go find more LEGOs, build a better tower, or something. Chances, especially with how early even we are right now, there’s still plenty of work to do. As more and more people join, if you take a look around, and don’t give into initial instinct, the odds are, there’s going to be something very new that you can go and dive right into, that the company needs.

Mike DiDonato (19:15):

And again, it was a really new thought experiment for me. This thought, it’s true, adding people doesn’t mean that there’s less work. It means that we can all do more, we can literally all do more. Like for you, if one person is the entire marketing department, imagine what happens when you add more and more amazing people. I remember Sam in emails to people would say, “Oh yeah, here’s the ops, I’ll check with the ops team.” And I’m thinking to myself, “The ops team is it’s me, and Josh, but Josh is moving away.” And the thing about this thought of replacing yourself, and always seeking to replace yourself, I think it only works if it’s a top down experiment.

Mike DiDonato (20:17):

If I think about Josh’s role in various ways has changed five different times, Casey’s, David’s, Sam’s. Sam needs to be in the trenches with me, fielding lead calls of people that signed up on our wait list, so that we can learn more about the people that are interested in the product, so that we can start building things into the product that these people want. And obviously that’s not what Sam does now, but I think it really only, it’s very much a cultural-driven thing. I think, as most things are at companies, but it’s a really, what’s the best way to say this?

Mike DiDonato (21:15):

It’s uncomfortable, to give the, but it’s all about how you approach it. Because any time that I’ve actually replaced myself, it’s always been a net positive. It’s always been a net positive, definitely for the company. And oftentimes it’s freed me up, and giving me mental bandwidth to think differently. When you do only … Sometimes we get focused, we have this laser-focus, and at times we can miss the forest for the trees. And the great example, a really, one of the main milestones, that I wanted to talk, that I was saying we had to come back to, is when [inaudible 00:22:16] joined the company. And leading up to that, I think it was pretty clear, although I could have done a much better job of voicing it, but it was starting to feel like quicksand, a feeling of quicksand.

Mike DiDonato (22:31):

I just couldn’t get ahead. I was, for the longest time, before we had an app and before we had all of these members, it was like, “Hey, you need to manage the experience for a few hundred people. You need to surface feedback, or get product feedback for the product team, AKA David. And that’s what it is. And as you can take on new things, great.” But started taking on all of these things, so ops and product, and you can even say that what Sam and I were doing with the lead calls, it was in a sense almost like marketing. Whatever. And there was this shift, and there was all these things on my plate. And once [inaudible 00:23:20] came in, it was helpful A, to make me feel better. Like I said, I think I was feeling that quicksand-feeling.

Mike DiDonato (23:38):

And also to see how he navigated it, and see that systems-thinking approach. Don’t be the mechanism, build the mechanism. It’s the, I think, one of the hardest parts about that replace yourself, is to just get beyond that initial response. And understand that’s a distraction, like, “Oh, well, is that really okay?” And then really focus on the big picture. It’s something, I think, depending upon your background or where you come from, who you are, it’s like there’s a learning curve, both cognitively how to approach that, and then psychologically. I know that I’ve actually, I’d say probably, in the last three plus months, I’ve really started to get in a groove, understanding, approaching big problems with that perspective. I think one of the things that’s been really helpful, is working with the Athena-team, it’s been really beneficial for me personally.

Ben Grynol (25:04):

Do you find that the quicksand, so going through all of this rapid change, do you feel that the quicksand is analogous to failure? So the idea of replacing yourself, if you’re doing things right, you aim to replace yourself, you aim to make what you doing, not from a role perspective, but from your involvement in it, obsolete? That’s sort of the goal, is to make yourself obsolete, because there is either a process or there are other people to do the work. Now there’s more people, there are different people that might have more experience, but that’s this this idea of stripping away the ego. The ego being, and not being an ego-maniac, where you go around with overconfidence, but the ego in a Freudian sense, where you strip away the ego and your identity, that, “I am this of that,” which is the case in, it’s easy to go down that path, “I’m the this of that, and that is me.”

Ben Grynol (26:13):

And you strip it away, and you’re like, “Wait, that’s a small portion of me. It does not define who I am, but it doesn’t matter if I’m the this of that, because I’m a part of a greater whole, and I’m still a part of that whole, and I’m going to be doing something different.” And so how have you thought about that idea of quicksand, not feeling like failure? Or has it felt like failure, and maybe that’s why it’s been quicksand? How have you stripped away the identity part of it, knowing that you’re still making an impact, doing different things.

Mike DiDonato (26:44):

Yeah, this is a really, and I want to make sure I get this right. Because of how quickly the company changes, I think I was a little bit, maybe slow at times, to adjust the lens I was looking through. When I first joined Levels, I was manning the relationship for A, our close friends, close network, family members. One of the first people I talked to was Sam’s dad. I was like, “Oh man, I cannot mess this up.” And then it was people with the last name, Flinner, and Conner, and Means, and I’m like, “Oh, damn, we don’t want to mess anything up, but definitely not this.” And it was with everything that I do, I approached this thing with like such a strong purpose. I feel like this, what’s the word I’m looking for? Not pride, but this weight, like people are depending on me, like [crosstalk 00:27:49]-

Ben Grynol (27:49):

Responsibility?

Mike DiDonato (27:50):

Responsibility, right, there we go. Thank you, sir. I just felt this immense responsibility that A, this for the first time, was my first experience working on something that just was so aligned with my values and my purpose. And I knew how important the work that we were doing, and all of these … It was basically the founders, and then me and John, and these people trusted me. And I was not going to let them down. And more importantly, it was not going to let our members down. These people that paid us this money and had these expectations.

Mike DiDonato (28:27):

That’s where I think there was some distortion when we get to like the quicksand. I think what I was missing at times, was the awareness that this was really going to happen. This way, it was not a scalable thing, what we were doing. But we have this thing at Levels, you can’t fail in silence. It’s okay, we run experiments all the time. Document it, take learnings from it. That’s amazing. That’s a win. But we just can’t fail in silence. I don’t want to say that I failed in silence, but I just didn’t know, was it okay for me to say, “Hey, I’m drowning,” and I eventually did get to that point. But it definitely wasn’t an ego that like, “This is who I am, and who it defines me.” It was more, “I have such a, the gratitude to be a part of this. And even more grateful that these put people have put their trust, and I’m not going to let them down.”

Mike DiDonato (29:30):

I mean, our team, I mean our members and that’s how I approach many things. Now where I think, one of the things that has really helped me, although I still have a lot of room to grow with this, is when you joined the team, A, you brought like a different energy to the team, and one that I definitely have since gravitated to. But it was, I remember one of our conversations, we worked really closely for a good six-ish months, or five or six months, something like that. And you said this to me like, “Look, we’re not the experts. We’re not. We’re going to do things. We’re going to take them as far as we possibly can. And then you know what we’re going to do? We’re going to bring someone in that’s better. That’s what we’re going to do. And the company is going to get way better.”

Mike DiDonato (30:15):

I think a really excellent example of this is, remember when we were doing the, what was it? The journaling initiatives, where we asked some people to just talk, “Record yourself, tell us about your day with Levels.” And one of them, we got many very thoughtful responses. I should clarify that. But there was this person, his name’s Chris Jones, it was such a detailed and thoughtful response. You could just tell something was different. I mean, turns out now that guy, Chris Jones, actually leads member experience here at Levels. But I think that was really helpful to hear it, like some of the interactions that you and I had. You’re like, “Look, this is just what’s going to happen. We have these projects. Neither of us are the, ‘Subject matter experts,’ but we’ll take them as far as we can. We’ll see if they’re useful, then we’ll bring someone, or something, or people to take this on.”

Mike DiDonato (31:19):

And even for you, when you first joined Levels, I mean, someone looking externally, that maybe doesn’t have, that isn’t playing the long game, would be like, “Oh, well, is he really doing something that the head of growth would be doing?” Because you were just focusing on these super important things like community, and all those different … And I was like, “No, that was really helpful for me to be a part of, and see that.” And it goes back to the … No one really cares. And Sam says this all the time, “It doesn’t matter who does what. What matters is that we get these things done, and we achieve our mission and really put a dent, and solve this metabolic health crisis.”

Mike DiDonato (32:03):

Like that’s what matters. We need to deliver an excellent experience for our members, and make sure that we get them closer to their long-term goals. We have a long way to go, a long way. But this mindset of … It was interesting, you said, “Ego.” It’s like, man, that doesn’t matter, head of whatever, none of that matters. It just doesn’t. And it does take a specific kind of people, or a person and team to really … No one has any, however you want to define, “Ego,” whichever one we’re talking about, nobody in the team has that. Nobody. It’s just, we’re all aligned, and we know what we’re working towards, and that’s what it is. And it’s definitely, you feel that from the top down.

Ben Grynol (32:50):

Did you feel when … So we were doing the member insights, building that up, just now member insights, member experience, everything you’ve done through the history, everything you’re doing now. Has it felt, and maybe it’s a combination of everything, maybe it’s none of them. But have you felt that it’s on the edge of a skillset? That it’s outside of your comfort zone? That it’s unfamiliar territory? Has it felt like any of those, all of those? Is that, because that’s what I’d imagine leads to quicksand? Where you’re like, “Whoa, I’ll figure it out,” but it’s easy to get wrapped up in the negative self talk of, “I don’t know.” It’s a lot easier to focus on the, “I’ll figure it out.”

Mike DiDonato (33:39):

So let me say, so it’s all been very foreign. But the quicksand feeling really came from just … It was two parts. It was at that time, things were getting insane. It was a big transformation, we’re talking about like the summer of 2020. And I think [inaudible 00:34:02] joined in August of 2020. I could be a little bit wrong, but I think so.

Ben Grynol (34:06):

September of 2020.

Mike DiDonato (34:08):

Okay. All right. You know what? Actually, I remember when Josh had interviewed [inaudible 00:34:12], and he did him, we had this thing called, “Teach me something,” and he taught him TextExpander, I believe, if I’m not mistaken. But this was right before, the summer of 2020, things changed in the company. A shift in the company was spring 2020, summer, 2020. We were supposed to, I think, we were going to raise in Q1 of 2020, then this thing COVID happened and changed things a little bit. That was another moment that I realized that I was working at a different company. I remember I actually pulled up the memo. Sam wrote a really transparent memo once COVID came in, and I was like, “Wow, am I … This company is amazing. This person is really being honest, and open, and transparent and saying, ‘This is what we’re going to do.’”

Mike DiDonato (35:01):

So coming back to quicksand, it was a lot of new things, but it was also just this shear load of things. I was still literally the only person managing the experience for everyone. We had an app at this time, but we had way more people using the product, and more and more responsibility was being put on me, to not only my manage that, but also manage the ops, or general operations, in general. Because I think at that time we needed, one of the things we needed, is we needed to get Josh off of operations, so that he and Casey could focus more on podcasts and media, and all the amazing plan that Tom created. It was a conjunction, I’d say, it was a lot of foreign things, but it was also just managing everything.

Mike DiDonato (35:56):

I remember my email would be blowing up, because Sam, it was right around fundraising, and Sam was talking to investors, and it was like, “Plus Mike, plus Mike, to the email that’ll help you. Plus Mike.” And it was a fun time, though. It was, it definitely did get to the quicksand feeling, but it was, and not that it’s not fun now, but even looking back on that. I can’t remember being, I was down visiting my mom at the beach, and I was just locked upstairs, just hammering away on email. We had the messaging platform front. Actually I don’t want to, this just popped into my head, which is really important, because, and I want to come back to the feelings of [inaudible 00:36:47] foreign as well.

Mike DiDonato (36:49):

But thinking about, since I said the beach, and talking about replacing yourself, I remember there was this night and I just got to see my mom down at the beach, and it was late, and Sam sent me text messages like, “Hey, do you have time to talk?” And it was a little bit late, but yeah, I was like, “Of course.” And we had just migrated, or not just, but migrated away. We were using a CRM tool to manage a lot of things. We were migrating off of that, and some Zapier stuff and Google Sheets, to Retool to be our source of truth for order fulfillment.

Mike DiDonato (37:30):

And Sam called me was like, “Hey, I’m not sure what happened. Do you know what happened? It looks like we have all of these open orders that never got filled.” And he’s like, “They need to get filled.” So I wasn’t filling orders typically, but I took it on me to go ahead and get it done. Sam and I talked weeks later, and we were just talking about that, and the process that we had then for orders, we were super janky. We were using Google Sheets to push orders, and consultations through.

Mike DiDonato (38:11):

And Sam’s like, we’re talking and he’s like, and this wasn’t in a malicious way. He’s like, “That must have been an awful experience.” And I was laughing and I was like, “Yeah, it was not fun.” He’s like, “Well, it’s your fault.” And it wasn’t like, “You’re a bad person,” thought of it was a learning experience. He’s like, “Look, I tell you this all the time, replace yourself. No one at this company should be doing things that they don’t want to do, but it’s on us to build those mechanisms.”

Mike DiDonato (38:45):

It just jumped out to me about the, it literally just popped in my mind, because they were talking about the beach and it was funny. There’s so many examples here of the importance of that. It’s like a … And every time that I think I’ve realized exactly, not just the value in how to do it, there’s just always another subtle reminder. So ultimately pushed up against that quicksand, and taking on these new things. I think you said your original question was, “Is it an uncomfortable thing? Is it because they’re new? Is it because it’s a skill thing?”

Mike DiDonato (39:32):

They’re all very foreign. Every one of them’s foreign, and one of the episodes that really hit home for me that we did, was the one with [Braden 00:39:40]. And he talked about Imposter Syndrome, and we all get that, especially when we try something new. But again, a big way, or big thing for me that changed, was hearing from you. Like, “This is what we’re going to do. This is just how we’re going to do it.” And you’re like, “This isn’t going to be for a few months, this is going to be in perpetuity.” Even now you’ll still check in with me, and be like, “Hey, how are you feeling about growth, about the change?”

Mike DiDonato (40:14):

And again, one of the things from that First Round Review, and it’s really true. If you want to grow as fast as your company, you have to give away your job every couple months. You have to resist that urge to hold onto these things. At times I think I may be, you need to be self-aware, and I’m very self-aware. I think maybe a couple times, I held onto things longer than I should have, it’s part of being human. But it’s how I see it.

Ben Grynol (40:45):

Given everything that you’ve experienced. So it’s your lived experience, but if you’re being introspective, and gleaning insight from everything that you’ve experienced and learned, what advice do you have for anyone? So anyone going through exponential growth at an early stage company? Things move fast, right? If you’re taking away one nugget, what’s that nugget? What do give as advice to someone else who might be experiencing these same things, quicksand, Imposter Syndrome, giving away Legos?

Mike DiDonato (41:22):

So first thing is, know where you are, make sure you’re with your people, say, you’re tribe, or the right place for this. If you’re at the right place, the first thing, communication, first thing is communication. There is no upper bound of communication. If there is, someone will tell you. But why I say that, is people have a problem, when they get caught off guard. If you’re communicating these things, whether it’s a process thing, or updates about a particular project, I’d say … That’s one of the biggest things that I’ve found, is as long as people are informed or in the loop, at least at Levels, there’s not really something that can go catastrophically wrong. That’s just more of a meta thing that I found working with this company.

Mike DiDonato (42:41):

But resist the urge, resist the urge to … How about this? Delay that initial urge, delay it, wait for, I think it might even be in that First Round Review piece. When someone new joins, if you feel uncomfortable, or you feel like you might be displaced, or you have some kind of insecurity, delay that urge for a minute. Have a conversation with that person. And as far as high level, replacing yourself, I think it’s important to know what kind of person do you ultimately want to be within the organization. Do you want to … You’re never going to be the head of, let’s take an arbitrary department, the head of customer support, if you’re answering every customer question. You’re never going to be the head of marketing, or the editorial director, if you’re writing every piece of content. Don’t be the mechanism, build the mechanism.

Ben Grynol (44:18):

Yeah, that gets to a very interesting point of thinking through how you can scale your role, scale your time, scale your outlook on what it is you’re doing. To your point of communication, it’s not just about being transparent and having a high cadence of communication to make sure that everybody is aware of things that are going on. But it’s also equally, arguably more important to be honest about feelings, the way you’re feeling about things. So if you open up and you create, you open the door of being a vulnerable, no one’s going to shun that, or shy away from that. They’re going to say, “Thank you for letting me know that you are underwater. You are feeling overwhelmed. You feel like there is some quicksand.” The outcome of not having that, is much worse because people say, “I had no idea.”

Ben Grynol (45:23):

And when you open up that door, people want to help. They want to find a way so that you don’t feel like that. That’s where this idea of communication, of being honest, of finding ways to replace yourself. You can only do that if you maintain a level of transparency and honesty with yourself, transparency with others, honesty with yourself, and really introspection to say, “Is this what I want to be working on right now?” And even if it’s not, but you’re tasked with it, you’re doing the best job you can. If you aren’t doing the best job you can, knowing it’s okay to ask for help. And that only comes from communication.

Mike DiDonato (46:03):

One of the episodes that was that really hit home for me, was the one that you did with Josh and Sam about founder dynamics. And I didn’t have that context, right? I was at the company, but I didn’t have the context to understand what was actually happening. That was, they were talking about a time, I think it was the spring of 2020. We have this, at times, thought, and I think Sam says this, either it’s the knowledge gap, or something, we just assume at times that people know everything. Or know what’s in our mind. That’s one of the reasons that we bias towards documentation and things. But the reality is there’s so many different things happening, that oftentimes people have no idea what’s happening unless you clearly communicate it. So be honest and open with what you want to do, and what you want to try.

Mike DiDonato (47:03):

If that’s not mapping to your core responsibilities, or what you’re doing, find a way out. Find a way out, and communicate that. Not saying to just drop all your responsibilities, but come up with a plan. I think being vulnerable is something really important. Vulnerability it’s difficult for a lot of people, not just in the professional environment, but personally, too. So be honest with yourself as well. Don’t think that just because you’re doing one thing, that you have to do that for the rest of your life, for the rest of the time with the company. Because it’s likely, especially if you’re at an emerging growth company, that position either may not exist, or it might look completely different. And what you once loved about it, might not exist.