Peer Effect
Best way to scale? Your peers have the answers.
This is the podcast for scaleup founders looking for insightful, actionable wisdom from some of the best operators around. Each week we’ll explore one secret that other founders and experts are using right now and how to implement it.
It’s practical wisdom to build the company AND life you want. Hosted by renowned founder coach and advisor James Johnson.
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Peer Effect
Overcoming Imposter Syndrome - with Charlie Greene of Remento
Charlie is the Founder of Remento, which was poised for a groundbreaking product last year. Drawing on his experience as a former speechwriter in the Obama administration, Charlie's journey is a rollercoaster of suspense, high stakes, and critical decisions.
We now step into the world of Remento on the Wednesday before Memorial Day, 2022, as the clock counts down to their monumental product launch.
Charlie is facing a critical moment in his entrepreneurial journey. Attending a pivotal board meeting, Charlie and his team had to shift their focus from refining their product to launching it within 100 days.
One of the defining moments arrives when Charlie finds himself grappling with imposter syndrome.
He faces a pivotal choice: to pretend confidence or embrace vulnerability and admit his uncertainties. It's a decision that will reshape the dynamics within his team and influence the course of Remento's journey.
In this episode we discuss,
- The critical role of resilience, humility, and vulnerability in leadership
- The willingness to be authentic, even in the face of adversity
- Insights into the power of staying true to oneself while navigating the challenges of entrepreneurship.
In this episode, Charlie shares his experiences and lessons learned from the Remento launch. Reflection and celebration are emphasised in the hurricane of startup life, reminding us of the importance of taking a moment to appreciate milestones achieved.
More from James:
Connect with James on LinkedIn or at peer-effect.com
So I'm delighted to welcome to the show today Charlie. He's the founder of Remento, which so far has raised over three million dollars to capture stories of relatives. He was also a speech writer in the Obama administration. Welcome, charlie. Thank you so much. I'm happy to be here so doing all some things at Remento at the moment. When are we going back to my coaching time machine?
Speaker 2:We are going back to the Wednesday before Memorial Day in 2022.
Speaker 1:Okay, wow, so it's not too much for jump. What's happening for you in Memorial Day 22?
Speaker 2:Well, it's just a couple of days before, and the moment that we're going back to involves a board meeting that really changed the trajectory of our company. For context, we had raised our round of seed funding 10 months before that and over the period between July of 2021 and May of 2022, it spent time doing basically two things the first was hiring a team that could help us execute against our mission, and the second was building a product that, for the first 10 months, could really serve as basically a research apparatus to help us understand if the vision in our head, which we had believed manifested in a very specific product like, made sense. And it was on May 25th that we realized that the time period that felt a lot like a science project of experimenting and testing and learning was no longer. The clock had been turned on and we had to act quickly.
Speaker 1:So quite a nice low pressure start like things have gone well, built the team, experimenting and quiet. What was this event that kind of turned the clock on?
Speaker 2:Yes. So for those 10 months we had spent the majority of our time working through the weight list of like a really nice size weight list that we accumulated even before we had raised the money, and in 10 months we got through about a third of those people, sharing different iterations of the product, getting feedback and developing what was, for me, a really exciting perspective on what was working really well and the areas where we realized we were just simply dead wrong about what we thought would work. So at the week of May 25th we'll start on May 23rd, which is a Monday we had our entire team at LA. We had just moved offices. I had hung up a 40 square foot adhesive whiteboard on one of our new walls, which I would never recommend trying to do solo. Thankfully I had my co-founder, but it was still a static mess. We got the adhesive whiteboard on the wall and our team spent the first two days of that week mapping out everything we realized was kind of the state of affairs of the company, the things that were working, the things that weren't working, the things that we wanted to test, the things that we wanted to hold ourselves accountable to, and how we would think about over the course of the coming months, be able to fold these into a product that we would be able to release.
Speaker 2:And on May 25th I went into a board meeting and it became very clear that the expectation was that by Labor Day we would have a product in market and that, depending on the year, is roughly 100 days. And I remember so vividly our offices in Culver City, our board was meeting in Santa Monica and it was a 16 minute drive back to the office and I remember getting into my car and wishing it was a 16 day trip back, because I knew that when I got back I was going to have to tell the team that everything that we had just spent the last 48 hours getting super excited about tackling would have to be scrapped, because what it was now time to do is focus on how do we bring everything that we have learned to market in a product that, fundamentally, we are going to be embarrassed to share with the people that we care about, which, for the record, every founder will tell you is exactly what your first product should look like. But I think, in reflection, that's a lesson that I imagine is hard for most founders to learn. It certainly was for me and just to give you a quick sense of the things that we needed to figure out in those 100 days. We had to figure out what we were going to launch Our product had absolutely not considered things like permissioning, legal sharing of content, all things that we believed to be absolutely critical to the user experience.
Speaker 2:We had spent no time on our go to market, thinking that the product and the viral loops that would be a part of the product would be a big part of our growth. We had spent no time on our branding. We had hired an agency to help us rebuild our brand, create a logo, create a landing page, test those landing pages. On top of all of that, we had gotten a cease and desist order that the name that we were using was probably not worthy of pursuing, given what would be an almost certain legal fight if we tried to use the name heirloom. So that was really the nail the really the nail on the coffin, and we had basically 100 days to take a science project and turn it into a product that we could bring to market.
Speaker 1:So just just to just to recap, for instance, it sounds like before this meeting you had a product that you would kind of experiment with, so it was kind of a science project. It approved, it approved the concept, but it but you had all. You just spent the two days of the team coming out with like what a really exciting next version of the product was going to be. You went to your board meeting and said no, no, no, you've got to release your existing one inside of 100 days.
Speaker 2:Is that right? That's that's. It's almost exactly right with this, the small caveat that it wasn't you have to exist. Your current version it's. You have to put something into the market by Labor Day, and one of the reasons why was we actually, up to this point hadn't announced our funding yet. The idea was that we would announce the fact that we were funded as a business once we actually had a product that we could lean into and drive attention to. So we had to, over the course of this 100 days, figure out what we were going to launch, what the launch was going to look like, what we were going to call ourselves, and then ultimately be able to wrap all of that into the press release that would say that this business exists and it's ready for people to download the app.
Speaker 1:I'm really curious how that felt in that meeting, when you kind of came in, I imagine, quite excited with all the things you're going to do and you were sitting with all the key sort of stakeholders financially in your business and they're like, no, no, actually, this is what you need to do. I wonder what your initial gut reaction to that was.
Speaker 2:Well, I'll just say, first of all, it was absolutely terrifying, and what was so terrifying was it felt like it was going to require us to make a huge set of compromises at a time where every day was providing additional clarity about what would ultimately serve our business best.
Speaker 2:So I remember going into that meeting so far it up, because I felt like the future was more clear than I ever could have imagined it would have been, and yet it was going to require us to release something into market that we knew fundamentally would not be as powerful and able to recognize its potential as the thing that we all imagined in our heads.
Speaker 3:So I would say terrifying is the first word I would describe that moment.
Speaker 1:Was there any instinct to push back on that guidance?
Speaker 2:There really wasn't, because it was absolutely the right thing to have told us at that time.
Speaker 2:Labor Day was going to be over a year since we raised our initial money and when I am chatting with first-time founders now, I just regurgitate the advice that was given to me in that meeting and the advice that I got before that meeting and the advice that I was given by fellow founder friends after, which is the first thing you released to your market, is going to make you uncomfortable because it, in doing the release, will teach you so much more than you could ever learn in stealth in closed beta. It made me uncomfortable, but it was a spoon of medicine that, as I was being served, it felt brutal, but I also knew, as it was being delivered to me, it was exactly the thing that we need to do and not to cut to the conclusion but, it ultimately ended up being one of the most important moments of encouragement and coaching, which felt like tough love and admittedly, it was delivered as very tough love and some of the best advice and encouragement that we ever got.
Speaker 1:Okay, so you've spent two days of your team. They're super stoked about what's about to happen in terms of version two of Remento, or not Remento, as it was called back then. You then go to the Traitors Board Meeting, you take your medicine, you hear it and you go okay, no, you're right. And then you've got 16 minutes to go back to your team and figure out how to tell them it's all, it's all, it's all change.
Speaker 2:Yeah, it was. It was a very short 16 minutes I was. I wish it had been a lot longer, but as I was, as I was driving back, it felt like there were basically two options in front of me. Option one was to pretend that I knew exactly what to do, which was very much what I thought was expected of the CEO and co-founder of an early stage company, a late stage company, any company, and that was personally drawn from a lot of my experiences where I worked for people who I respected so damn much, who always seemed to have the perfect answer. That was one of the tremendous biases that, as I started this journey as a founder, I've come to recognize, which is it is not always the case that the person at the top knows exactly what to do. And the second option on the table was, after having meditated on that, that first realization was to walk into the room and say I don't know what the path forward is, but here are all of the balls that we are going to have to juggle over the next hundred days.
Speaker 2:So for me it was kind of like this existential style question of the leader that I wanted to be. Did I want to aspire to be the leader like the ones that I had worked with in the past who always seemed to know everything, who maybe they were wrong, but they always had the exact plan? Or did I want to be the leader that walked into the room and said I'm not sure what we want to do next. Let's figure it out together. And as I say it now, I think like listening to myself, it seems so obvious that the plan B is exactly what we should all be doing as leaders.
Speaker 2:But, it wasn't nearly as clear to me at the time. Ultimately, that's exactly what we did. I went into the room, I sat down in the chair and I said the reality is that things are different than they were three hours ago. Let me explain to this team exactly what's just happened, and every person on this team represents a different function. It's one of the beautiful things about being a small company it's really understand who's good at doing what, because they're all fundamentally different things, and I think it was in that moment that it became very clear that the team, having been empowered to work with me to figure out what this plan would be created a level of shared terror, certainly, but also empowerment and motivation that our team had actually never felt and seen before.
Speaker 1:Interesting. So do you feel like the outcome of that meeting was even greater engagement than the outcome of the previous two days?
Speaker 2:It was certainly different. It was a different level of excitement right, it was one of them was based much more on the opportunity to be able to build something great. I think the second meeting was one more focused on the fear of totally whiffing it, because what was very clear to all of us is we had staked our names as being part of the founding team building something, and I think the product that any of us build is unique and different. There are some things that are very similar across many different companies, but for us, we had all come together to build something that we felt truly would make the world a better place if we were successful. So there was the ego associated with professionally wanting to be a part of a one and not a zero, but at least for me, and I think for others as well, there was this real sense of pressure that we place in ourselves to be able to execute against the mission that, if we were able to fulfill, would make a difference.
Speaker 1:It sounds almost like it's both for you as a leader but also for the team as a whole, like a sort of maturity moment, like the sense of, up until you've gone to that meeting, it was kind of like a school project. There was no external marking. It was kind of like you've got to kind of play in secret, almost with no real consequence, and then suddenly it's kind of like no, no, there's a timeframe, there's public success, failure, there's kind of consequence. It just sort of like going from school to your first job or something.
Speaker 2:It totally does Like we're playing in the real leagues here and the school project is a little bit of revisionist history in my part. That's the way that I think about the first 10 months of what we were building. It certainly felt at the time that the stakes were high, but it did feel like it was more like we were in an incubator or in a lab. Then we were having to execute against a timeline for which there would be consequences if we fell behind. So it was a maturity moment. It was a realizing that we have to be accountable to ourselves, also to others, and I would say it was a moment of like professional maturity for me as well, where I realized that providing more context to the team allows people to be able to understand the variables and make choices for themselves that reflect the conditions that we operate in. So coming into a company where imposter syndrome is inevitable but I think at the time I felt like I had like three or four times more imposter syndrome than anyone else could have felt.
Speaker 2:My background is non-traditional, non-linear, this is my first time working at a tech company and now I had a meaningful role in running one, so I remember being very skeptical at the time of knowing what to do next, and it felt like having the answers would have been what was expected. And ultimately, what was such a beautiful thing to watch is to see everyone in that room take on the weight of figuring out what to do together.
Speaker 1:That's really interesting. You say your path to this position was non-linear. Like you said, you'd been a speech-rising bar demonstration, which you felt led you to more sort of potential imposter syndrome. When you looked around at your peers, did you feel that they had like more of a background into the roles that they?
Speaker 2:had. I can say from my perspective, it certainly felt like someone who had been running one-on-ones for the last six years in a technology context. Having been trained in those practices had a leg up on me. Having to learn a lot of that stuff on the fly and be coached and mentored from people that I worked with.
Speaker 2:The corollary is there were things that I was probably able to do a little bit more thoughtfully with a little bit more experience, but from a tactical perspective, I found that the first year of running this business felt like a lot of catch-up, which I think the reality is. They say this about being president. Of course, being president is something like being a founder. There are very few roles that can perfectly prepare you for this job. At least that's been the case for me. So, yeah, I certainly felt at the moment that there were people who were probably better prepared in certain areas to be able to weather the early kind of turbulence of an early stage startup than I was.
Speaker 2:But at the same time, I was as motivated, I was as willing to learn and I think one of the reasons for my success is I've always been able to surround myself with people who are just phenomenally talented at what they do, and I've never resisted the urge to seek feedback along the way from how. I knew my job better from them.
Speaker 1:It's really interesting to know that the response to imposter syndrome was not to go for Route 1, which was I know everything and sort of fake it, but actually to expose yourself and go. I don't know, and let's all do this together. In retrospect it sounds like the right decision and the obvious decision, but how much sort of backwards and forwards was in your head on which way to go.
Speaker 2:Yeah, well, I mean, you're exactly right. Like it's antithetical to what imposter syndrome tells us we should do. Like, if we're skeptical as to whether or not we have the answers, we want to confirm that we are either correct or incorrect. So we go for the path that leads us to confirm that we think we have all the answers reality.
Speaker 2:We actually don't. So I think up until the last, up until that point, the previous 10 months, like I was acting under the impression that I had all the answers and in retrospect that was just so backwards, such a backwards way to approach building a company, particularly one where you have what is the tremendous privilege, as CEO, of having the opportunity to hire only the people you want. It's like by far the best part of my job. I get to decide, at the end of the day, who exactly is on our team, and why on earth would I ever build and bring together a team that doesn't reflect a diversity of skill set and expertise that would allow all of us to do a job that I couldn't do on my own.
Speaker 2:Of course, it makes so much sense, but it was in that 16 minute drive home for me as a leader that it just became so clear that I didn't have an option.
Speaker 2:Me trying to couple together a plan in that 16 minutes, it just wouldn't have made sense to anyone in that room and it would have felt so disconnected from the previous 48 hours that we had just had. So, in a way, being able to point the finger at an external force that was casting a set of very specific controls for us over the next 100 days, it allowed us to come together and for me to take off, I would say, the CEO had as the person who's making all the decisions, and take on the CEO as coach had and say, like my job is to make sure that everyone on this team can do their best work. And I remember, like driving home, I was reflecting back on one of my professors from business school. Ryan Bewell has an amazing framework where he talks about high performing teams having three different dimensions. The dimensions are capability, motivation and license. So I remember, as I was hiring for this team, I was thinking through in my head does this team reflect those three different dimensions? And as I was driving back, I was doing like this mental inventory of my head, thinking, okay, does this team have the capability to do what is expected of us? And the answer was unequivocally yes.
Speaker 2:Every single person on this team has, in every moment up until this point, risen to the challenge that's been presented to them. So capability we checked the box. Are they motivated? At an early stage startup no one is joining if they're not motivated. Everyone is highly, highly motivated for this to be a positive outcome because they've staked their own professional reputation on that. So motivation is clear.
Speaker 2:There's one part of the triangle that's left and that's license. Do they have the license to be able to do the job that's expected of them? Do they feel empowered to be able to do great work? So at that moment, that was the question Like if this team is going to be successful, there's nothing we can do about the capability right now. There's nothing we can do about the motivation right now. Thankfully, those are both in good shape.
Speaker 2:This is a question of do they have a license to do good work? And the only way that you can give people the license to do good work is to push the decision making down to the level where everyone actually has a vested interest in the outcome, but then also their ability to shape the outcome. And that's ultimately what the meeting that followed after our board meeting did, where we refilled up our 40-foot whiteboard, with a go-to-market plan, with a product development and strategy plan, with a quality assurance and testing plan, and made sure that, in addition to all of those things, we came up with a name, we began a trademark process, we built a website and did all the other things. So the number of different elements of the team was able to come together to accomplish in the 100 days was amazing in retrospect easily the most productive three-month time span of our company's history. And it was only because I didn't feel like at the time I had a choice.
Speaker 1:Having unlocked this team and unlocked the next stages, did that increase or decrease your feeling of embossed syndrome?
Speaker 2:The imposter syndrome is still super real. But what I have now is a sense that, through the single experience of that moment, just a data point. There are now more data points, but a data point that says when we actually step out of the limelight for a second as a founder and invite others to be a part of that moment, it's when we are able to unlock the biggest and greatest potential from our team.
Speaker 1:It's very impressive that you in that meeting, responded with humility and said okay, no, no, you guys know what you're doing.
Speaker 1:The investor meeting first. Both how you handled investor meeting and the team meeting could have been handled very differently and I say that having been a founder and having probably handled some of those meetings differently myself, but like feeling defensive, feeling excited and then defensive and uncomfortable, being a room of investors who had those knowledge gap, experience gap, it's quite easy to respond to that defensively and go no, no, no, this is the plan, rather than actually listening because you feel defensive and uncomfortable. So I think that's really impressive and then, in the space of 16 minutes, being able to get yourself back, back aligned, to address the team in a way that would resonate with them. It would be quite easy to have been sort of blown off course by that meeting. So I'm just curious did you have any background before this in dealing with, like I said, with emotion, intelligence, or managing your, managing your chimp or sort of mindfulness to keep yourself calm and centered in both of those meetings?
Speaker 2:I think the answer is yes. I think I did have experience doing that, but I would have never at the time identified it as experience with emotional intelligence. Like for me in my life, I had the opportunity to learn pretty early on that resilience is a muscle and it's grown and developed over time, and people who have overcome challenges have the really important ability to empathize Thank you in a way that is incredibly powerful if channeled and can be debilitating if it's not. But I think for me, humility has always been one of the values that has mattered most to me personally and the people that I care about and the teams that I've had the privilege of being able to bring together.
Speaker 2:One of our company values is no ego amigo. It's like if we can't, if we can't, as a company, look out for each other and have each other's backs, like, what are we doing here? So I think the corollary with empathy that is so important for teams to become high functioning is vulnerability, and there's a tremendous amount of research around the connection between vulnerability and psychological safety, which is such a critical and necessary preconditioning condition for high functioning teams to be able to show up and do their best work every day. So what became very clear to me over the course of my career, having seen the people that I was so impressed by at a distance open up and share and be vulnerable. It just changes everything. It just totally changes everything.
Speaker 2:We are most scared of the things that we don't know, and as soon as we see the people that we work with, that we respect, that we look up to being human and sharing what's on their mind. It's just an invitation to join their team. That was one of the things that every person that I've ever worked with has done such an amazing and wonderful job of. So it's something that, as I think about the leaders that have shaped the way that I think about leadership, it's something that I model as well, and I think it's especially important, as a straight white man leading a company, to recognize that people are showing up to the workplace, the home space, like with such different experiences. If we can find it within ourselves to open up and be vulnerable and talk about the things that we're thinking about, it just creates the space for the people that we spend our time with to do the same.
Speaker 1:It's really personal. I feel we could go down a whole path down there, so so the audience can hear where the story goes. I feel like that was quite a pivotal moment. You had this a hundred days. What happened at the end of the hundred days and where are you? What's the Romento story today?
Speaker 2:Yeah well, it was total madness. I mean again taking all of these component pieces of different experiments, putting them into a single end-to-end app that got released to the app store, got approved to the app store, got reviews into the app store, and then wrapping all of that into a company launch with a go-to-market and public relations. Like it was a Herculean effort and just such an awesome, awesome thing to be a part of. Admittedly, though, it was a huge act of vulnerability, and I don't think I'd ever appreciated that how much it is.
Speaker 2:Launching something into the world, the first thing that you put your name on, that you put into the world, and I think this is one of the reasons why founders tell you to launch things earlier. It's because if you feel that the stakes are lower when you start getting the feedback that you want and the feedback that you don't, it just feels lower stakes because you released it so early to begin with. So we launched our product, we came up with a new name, the name is trademarked, everything is going really well, and then I think all of us had this feeling in our stomach that was like, oh my gosh, now what do we do? We've just released all of this content. We've been flooded with messages from different people who are pouring into our personal messages, into our LinkedIn account. Strangers are reaching out, people are using the app and they're telling us. This problem resonates so much. I love what you guys are building. There are parts of this that are dead right. There are parts of it that feel off, but overall, kudos to you.
Speaker 3:And I was like oh my gosh awesome.
Speaker 2:We haven't thought about what's next for 103 days and it was like let's go back into our phone and find that image that we took before we erased the whiteboard to see what was on there. So one of the big moments that was important for our team to be able to embrace and move through was that pause. That was very necessary at the end of having launched. As a founder, we know that one of the things that distinguishes early stage companies from others is speed. So our bias is towards moving quickly and I'm an incredibly impatient person when it comes to the product development process, in part because I'm just so excited about what we're building.
Speaker 2:So I've worked on that and I've learned, but I was so ready to start taking out what comes next that another learning moment for me was realizing how important it is to celebrate a team and good work when it happens. So we definitely did take some time to pause and reflect on On that moment. But yet it's been at this point almost a year since we launched the product we launched, and we ended up launching just after Labor Day because we learned that launching a brand new product at the very end of the summer is not the right time to do that. So we were able to convince everyone that it made more sense to do it at the beginning of September, and our product is in market. It's a mobile app that is designed to help families collect and enrich the stories of the people that are most near and dear to them.
Speaker 2:We use a variety of different prompts for being able to bring the stories of the people that we care about to life in a recorded context, and our team has spent all of the time since we finished celebrating our launch, which did not last very long, to today, thinking about what the second and third and fourth versions of of of Remento look like, in large part driven by all of the new tooling that's become available to our team thanks to many of the developments related to artificial intelligence. So there's a lot of different stuff that we're working on right now, none of which have, I would say, the level of intensity as we felt during those those hundred days. But I can assure you that we're definitely still moving fast and have a lot of really exciting stuff in the in the pipeline.
Speaker 1:And looking back on it today, what, what's, what's maybe a big takeaway, apart from maybe having your board meetings about two, three hours further away. So give you, give yourself more time when you come back.
Speaker 2:I think my biggest takeaway is is how important it is to hire the right team A and B, to make sure that when you hire the team, you're willing to bring them into not just the execution of the plan but the development of the plan, and I think that's that's something that comes really naturally to a lot of people, and it certainly did not come naturally to me, and most of that was because I was just so damn excited about what we were building.
Speaker 2:I had the vision just so crystal clear in my mind, and it wasn't until I had the opportunity to step back and realize that I was being asked to do something that I could not do on my own, that I had the opportunity to bring other people in. So I would say that would be my, my, my, my biggest takeaway hire right and then and then bring people truly into the way that you think about the opportunities running after.
Speaker 1:Amazing Charlie. Thank you so much for sharing all of that. It was fascinating and very, very insightful.
Speaker 2:It was such a pleasure. I want to say one of the great privileges of what what I get to do is I get to talk to a lot of our advisors, who are scientists and professional interviewers, about interviewing best practices, and time and again, the thing that it always comes back to is being the biggest distinguisher between the best and the rest when it comes to interviewing. Is active listening, right listening a little bit more, not writing out your full list of questions, and it was the reason why I was so excited to be on this podcast, because you are the gold standard for active listening, actively getting coached as I go through the conversation. So I'm just honored to be on the podcast.
Speaker 1:Thank you.
Speaker 3:Charlie, as you heard today, coaching opens up a whole range of insights and areas to explore. If you have a potential moment to revisit on the podcast or just want to learn more about coaching, book in for a 30 minute chat with me at peer-effectcom.
