How to Go From Startup to Scale: Lessons from Top Business Operator Regina Gerbeaux

There are a lot of people who are takers, who have a lot of clout, who have these amazing networks, who are very well known and liked in their spaces. You can define that as successful, but I would not define success so narrowly. If you go over to somebody's home and they have this beautiful big house with all the amenities and just a really beautiful looking house, you don't go in and say, wow, I love your plumbing, or wow, I love your wiring. You go in and you talk about the aesthetics of it. You talk about, wow, this is such a big and modern and beautiful place, look at the wood accents, look at the metal accents, you cannot have room for takers. You have to at best optimize takers to become matchers, but even then, it's usually not worth it in my opinion. When it comes to hiring, when you're trying to avoid hiring takers, listen to the kind of language that they use. When they talk about their accomplishments at another company, did they say that they did everything by themselves and that they didn't have any help? Do they prop themselves up as the person who was kind of the mastermind behind all these other things.

One of the reasons I was really excited to do this is when you think about sort of like founders and creators, most sort of fall into this bucket of, I want to be creative and I want to work on just the stuff that I like, right? Whether it's like a creator or a founder building a multi-billion dollar company, one of the sort of unsung things that isn't talked about is, is the operations part of it, which really like pulls everything together. And you are one of the sort of like best operators I know within the context of everything that we did at On Deck, your work with Matt, who's been on the podcast. And when it comes to operations, again, like founders and creators don't really care that much about it, right? One of the things that I was thinking about from our pre-conversation was even if I look at what I want to do in the next 10 years, it's how do I play this infinite game of taking ideas that are in my head, and executing them creatively without worrying about sort of like the operation and stuff. And the thing is, I can do that, but you know what happens when someone does that, which is if you don't have operations, things will just collapse, right? So for creators and founders that are listening, can you contextualize actually the importance of operations and why we've been like spending so much time on this because, and why it's important?

It's such a good question. The way I like to think about operations is thinking about What it means to have a really nice home. So for example, if you go over to somebody's home and they have this beautiful big house with, you know, all the amenities and just a really beautiful looking house, you don't go in and say, wow, I love your plumbing, or wow, I love your wiring. You go in and you talk about the aesthetics of it. You talk about, wow, this is such a big and modern and beautiful place. Look at the wood accents.

Look at the metal accents.

And, you know, I'm sort of revealing the kind of house I like through this analogy. But the last thing you really think about saying is, oh my gosh, your plumbing is exquisite, or, wow, look at these electric wirings, or, wow, your insulation in this house is amazing. And I think the reason that I bring this analogy up is that, you know, operations is very similar to the plumbing, the electricity, the wiring, the insulation. Because the house is not livable, no matter how beautiful it is, if you don't have those things. I think somebody would rather live in a modest home with all of those things working properly than living in this giant mansion with none of those things or broken things. And as you know, those are also often the things that are the most expensive to maintain and to Fix if they are wrong or if something breaks or something goes bad, right? So in a lot of ways, for founders and creators or whoever is building anything, you have to have a very solid foundation, meaning it's not just the rock that you're building your house on, so to speak, but also the plumbing, the electricity, the wiring, the insulation, and so on. And I think operations forms those things. You can't have the beautiful home without those Essential components. I also like to think of, you know, a human's hierarchy of needs. You have to have food and shelter and clothing and water and all of those things, and then you can have the rest of the stuff. Well, so many people try to jump to the part where they're successful and wealthy and well-off and famous, but you can't have that unless you have your basic components first. And similarly, when you're building anything like this, you can take it all the way back to first principles. When you build anything, You have to have a solid foundation. You have to make sure that your needs are met. And I think that operations basically encapsulates all of the things that are necessary in order for you to be able to think big and stretch and grow and not have the house crumble while you're doing so.

And when people are— when I even like first thought of operations, right? Like my first instinct is let's jump to, let's build a Notion board or let's do Trello. It's sort of like the tactical side of it. One of the insights that you— I remember learning from you when we were at On Deck was it first starts with the person. So can you talk about the importance of actually starting with the person first and not jumping straight away to like tools and tactics?

Sure. So I think long story short, you don't have a company if you don't have people. And what I mean by that is it doesn't mean that you have to have lots and lots and lots of people. But I do think that if you want to build something truly exquisite, And extraordinary, it takes a team, it takes a village to do so. And the only way you can have these people on board with you is either if they feel very cared for, or they feel like they can benefit from the relationship, or both. You know, the best leaders figure out a way to trigger both. And the reason that both matter is because if you make someone feel Like they can benefit from the situation, that's nice, but that's very transactional. And the danger with that is that you risk finding people that are takers or matchers. You know, Adam Grant has this book called Give and Take that I love. And if you find those people that are very transactional in the way that they interact with you or other people, they're not going to be there for you during the hardest times. And as you know, building anything worth building has these peaks and these valleys, and you want somebody who's gonna stick through all of that. Similarly, if you, you know, find people who care deeply because you make them feel really good, that's awesome. But I think that means you've won a friend, and you want somebody who's going to say, you know, I have a desire to make something bigger than me, and I have a desire to do this with people that I really love. So I think both go hand in hand. And the way that you get the best people to work with you and follow you from place to place to place is by really investing in them and caring about them, by taking the time to get to know them, and by genuinely giving a damn about them, right? And only then do you have the building block for people that are really, hopefully they're smart, they're ambitious, they're talented, and they actually care. You know, and they're going to go with you through the peaks and the valleys. You can't have a solidly run organization that executes constantly and at a high bar and well, unless they feel like there's a reason for them to do that. You know, talented, smart, ambitious people are not going to tolerate bad behavior. They're not going to sit around and tolerate somebody who's going to treat them like lesser than or like They're a dispensable number, right? And frankly, most of them can probably go off and do just fine at any other job or any other place, or they might even start their own thing. So you really, you know, have to give them the reason to see that the best place they can be is working with you. So you can't have operations unless you take care of the people first.

So, so meta question on this, whether it's in terms of like hiring or once someone has joined your team, how do you operationalize these 2 concepts of caring and the benefit part?

When I started my first tech company, I was 19 and I didn't hire my first person until I was 21. And during that conversation, I remember, I remember talking to this person. She and I were already really good friends in college. We both went to USC together and we were both in the same class and we spent a lot of time with each other already. And so it became this no-brainer that I should bring her onto my team 'cause we already cared for each other and we liked each other and she was smart and very, very capable, a much better musician than I was. It was a music business, right? But the conversation that she and I had, which set the precedent for every person I hired after, was, this is more than just a paycheck and I want you to know that. You can probably, Earn more money somewhere else. You can probably— you would probably qualify to teach at whatever school or whatever. But like, if you're here, you're here because you believe in what we're doing. What we're doing is this. And then I would explain the mission to her, which was at that time it was to bring joy through music for people of all walks of life. And so I use this example because I think during the hiring process, it's important to assess out the why behind a person's intent and being there. I also think it's important to find examples, right? Like, instead of them just telling you about how gung-ho they are on their mission, try to understand what is it that you are trying to build in your own company, whether you're a creator or you're a founder. What are those things that you care about? And then ask that person, you know, To demonstrate a time where they really cared about something in the same way. That's the— that's one of the best ways you can find cultural fit. You can also do this during reference calls. So when I would do reference calls, I don't, you know, just call and say, hey, tell me all the bad things that people had to say about this person, which, you know, there are some people that do reference calls like that, and that's fine. It's a legitimate way of doing a reference call. But for me, what I wanna know is, okay, if I care deeply about having a we, not me attitude at my company or whatever I'm building, I'm going to ask that person, can you think of a time that this person demonstrated this kind of character where they put that entire team above themselves, where they made an actually significant sacrifice for your team, right? Or tell me about a time where they were faced with a hard decision where they had the choice to either sacrifice for the rest of the team, for the greater good of the company or their team, or they chose to, you know, do something that was to their advantage. And then I don't sway it, you know, going one way or another. I don't frame it as a, tell me about how they sacrifice. I just wanna know, like, what did this person choose to do? And so, those are some ways that you can suss out whether somebody is a really good fit for your culture, and you know that you're gonna be able to build this kind of relationship with them during the hiring process. And then I'll share another story about what it looks like when you finally hire someone and you onboard them, right? I see the onboarding process is the most pivotal time, one of the most pivotal time for developing the relationship with this new employee or this new teammate because you're just starting out this working relationship. Maybe you've been friends for a really long time, but when you start working with someone, it completely reframes and changes the relationship. There's a new— Aspect or a new element introduced to your relationship, which can be a really beautiful thing, right? And so I think availability is really important in the first 90 days. That's going to be the time that you're really building great connection with this person. And a couple of different ways I see this happening include offering a space where somebody feels like they can ask you a lot of questions, right? So, one thing I would do is, like, in this particular example that I have in mind, and I'll share the story in a second, I had an asynchronous Slack channel with this person set up where he could just ask me any questions, any and all questions, and I would actually message him and say, what questions do you have for me today? And I could have set up a bot to do that, but it took me 2 seconds to do, right? Drop your questions in, and I'm gonna answer all of them by the end of the day. Right? And then I can batch answer them. I also had them have an onboarding buddy. So, they, in this case, there were already other people on the team. I would've been their onboarding buddy if I was the only person on the team, but they were able to go and ask these other people all the questions that they had. And then finally, when it came down to feedback, in this particular case, the person I'm thinking about, one of the best people I think I've ever hired in my career, my entire career. And he came up to me one day and said, am I doing enough? Right? And he had been on the team maybe for 2, 2 and a half weeks. And I remember just thinking, oh my gosh, I love this guy. Like, he, he was like, I don't feel like I'm doing enough and I want to improve. Right? And, and that to me, that told me a couple of things. One, we have trust because he's coming to me and saying to his boss, to the person who has the power to hire or fire him, That he feels like he's not doing enough too. He wants to improve. I care about people that constantly want to do better and be better, not only for, you know, themselves or for me, but for the entire team, for everybody that's depending on them. And then, you know, 3, he wanted really concrete, tangible steps. So, when somebody does that, I think some managers could be like, oh, what a lot this person Like, can't just do it on their own. I have to get involved. Well, guess what? When you hire someone, you have to get involved. That's just part of the job, right? If you don't want to do that, bring somebody on who's going to do that for you, or don't bring people on. Don't build a company. And the thing is, like, you, even if you bring somebody on to do it for you, just know, know that that person that you have doing that is going to be the person The new employee trusts, not you. You can't outsource something like that. So in this case, this person, going back to the story, he says, am I doing enough? I don't feel like I'm doing enough, and here are the things that worry me. And I wrote back and I basically told him, yeah, like, I think you're going at about 80% of what you can do, and here are the different ways, here are the different questions you can ask yourself. And in this case, this person was quite young. And I basically said, look, this isn't college anymore where somebody is going to assign you homework, then you have to study for a quiz or whatever. You have to ask yourself, what is the next thing I can do to be helpful to my team? How can I sacrifice something in order to make life easier for everyone else? And the beauty behind this word sacrifice, I think people have The notion that you have to stay up really late and like work super long hours to be considered like as that you're sacrificing something. But the beautiful thing when you have a culture and a team like this is that everybody is doing this for the rest of the team and it actually makes your life easier. And so if everybody has this mentality and nobody on the team is a taker and everybody there wants to genuinely help everyone around them, that's when you have a really solid team. And in this case, I think Sachit, you know, the launch team like this, I think that was generally speaking the culture of the people that were there. And we were like 20, 30 people in one quarter. So, it was not like it was a significant amount of time to build this over a long period, but it was like hiring all these people at the same time and then going from there was a lot. So, I told them, what can you do to help other people? How can you volunteer? How can you jump in? You know, I want to see initiative. And this goes into this concept of bias towards action, which I'm very passionate about. The concept of bias towards action basically says, how can I get something done in the next 30 minutes? Right. But I think even more powerful than that, and something that I challenge every operator I talk to, every— and even every founder and creator I talk to, because I think the most effective people have this already, is how can I get this done before anybody even asks me to do this? That means you are becoming attentive and predicting the needs of the people around you, and you just take that initiative and you say, this is what I'm going to do, right? That's the mark of a true leader. That's the mark of somebody who is going to be highly effective. That is the mark of somebody that's going to be an amazing operator. And those are sort of the tactics that you can, you know, use or the things that you can think about when it comes to, you know, the onboarding process.

One of the things that you also mentioned in here was that the right person, they're not takers, right? So, and I'm glad you mentioned sort of like Adam Grant's framework of like givers and takers. The same thing there, like how would you, when you're hiring, what can you do to like make sure that the person that you don't bring on ends up being a taker and they're only looking out for themselves? Especially when people are really good at telling stories and narratives and all those different things.

There are a couple of different ways I think you can make sure you're not hiring takers. Obviously, it's not foolproof. There are always going to be people that are really good at faking it. And so that's why, you know, regardless of the hiring process, you have to be okay with letting people go quickly if you, as soon as you sense it, 'cause it is like a toxic poison that will spoil the entire well as soon as they enter. You cannot have room for takers. You have to, at best, optimize takers to become matchers, but even then, it's usually not worth it in my opinion. So, when it comes to hiring, when you're trying to avoid hiring takers, listen to the kind of language that they use. When they talk about their accomplishments at another company, did they say that they did everything by themselves and that they didn't have any help? Was it the case that they talked badly about other people on their team? Do they prop themselves up as the person who was kind of the mastermind behind all these other things, right? Look for, look for how their work experience looks like too. I think sometimes people that are takers can have these crazy work histories where they're just jumping from place to place, like month, month after month, right? And I think that that can sometimes be optimizing for, you know, positioning, right? And then moving on, positioning and moving on. And then honestly, I think it's a matter of understanding how they interact with people who are maybe perceived as lesser than to them. Are they really good about talking as we— and we did this together and it was a team effort when it comes to their equals and peers or people that Are ranked higher than them? Or can they do that also with younger people? Can they say, I honestly really relied on the help of these amazing interns that were there, or these like really fresh out of college kids, and like we all got together and they were honestly the ones that were super smart and just like executed on all of these things? Can they talk about their projects that way? Can they talk about times that they have failed? Like, takers are awful at talking about failures because they don't want to admit that they've done something that, you know, was not successful. Can they talk about it in a way that does not avert blame, that is not shameful? Can they approach it from a lens of curiosity? I think those are the main ones that I look for. And again, it's an art, not a science. If it was a science, we'd all be expert hires, right? And there's a reason why Recruiting agencies like make so much money. It's because there are people that specialize in looking for these kinds of behaviors. But I think the main thing is understanding how to listen to how somebody talks, you know, and what kinds of conversations are they having with you? What kinds of questions do they have for you? That's another good one. So if you're a hiring manager and by the end you say, what questions do you have for me?

Mm-hmm.

And they ask you about things like where, if everything is very like financially motivated or if everything is not very, if there aren't really any people-oriented questions, I think those are all red flags. And you can see that I'm taking a lot of time to think about this because obviously it's not so straight cut and it's not black and white, but this is such an important topic, right? need to optimize for hiring amazing people that are givers rather than people that are just going to drain a company and then walk away. I think everybody can also have their own take on what a taker and giver looks like, right? Like, there are some companies that are optimized just for like growing really big, really fast, and then exiting, right? And that's fine. Like, if you're going to be that kind of person and if you yourself are a taker and you're okay with that, And you already know that, just know that that's the kind of culture you're building. There's no such thing as the right culture or a wrong culture. I'm giving all of this, you know, input from my own point of view, which is that I never want to work at a company or build a company that is run by takers. But I think there's room for every, for every type of person, right? It's just, that's not the kind of company I'm interested in building.

So, and I think to add to that, it also doesn't, because this is something I've realized over, over sort of like last few years, which is if someone's a taker or someone's doing something wrong or whatever in their company, even though like we're like, oh, like that person should not be successful, they're still successful, right? So this also doesn't reflect on success because you can be a taker and still be really successful. It's, as you said, it's about building the kind of company you want.

And in that sense, um, I want to say something to that effect. And that is, I think it really depends on what you mean by successful and how you define successful. There are a lot of people who are takers who are very financially well off, who have a lot of clout, who have these amazing networks, who are very well known and liked in their spaces or whatever, right? You can define that as successful. But I, for example, don't I would not define, I would not define success so narrowly. I don't think for, like, for me personally, if somebody has done something to wrong somebody where they've, they have a lot of, you know, skeletons in their closet as they ascend the path towards, you know, this version of success, I don't consider that successful at all because at the end of the day, you still have those skeletons in your closet. So again, it really depends on how you define it. And it depends on whether you're optimizing for short-term gains, right? A finite game, or if you're thinking long-term, because people don't forget how you make them feel. People don't forget the things you do. People will, well, people will cheer for you until it becomes more sexy to root for your demise. That's something people have to think about. Yeah.

And, and definitely like when I, when I was thinking, when I said successful, I meant sort of like the outwardly successful part of it. And, and the thing I was getting at there was In a lot of sense, in a sense that when you're thinking about this, companies end up being a reflection of the founder or the creator psychology, right? Because whatever sort of like, whatever values they have get reflected within their own company. So can you talk about the importance of CEO psychology? And when you're working with a CEO or a founder, what are some of the tools and tactics you recommend they use? In that sort of like zone. Wow.

Yeah. Founder psychology, man. It's, it's really funny because, you know, my job as a coach is part tactical in the sense that we talk about real business problems and we work through ideas and I serve as sort of the sounding board. But that's only part of coaching. There's this whole other thing that usually comes out once my coachees and I have built a really good relationship. Where it really becomes about their psychology, not only as a leader, but as a parent, as a spouse, as a partner, as a friend. Like, it really comes out. And the reason for that is it turns out you are the same person wherever you go, whether you're at work or you're at home or you're out with friends or whatever, right? And so the way that you behave translates in one way or another to the work that you do. So, I sometimes get coaches who are amazing, amazing, you know, business, and they're really great at leading product, and they're able to close deals like crazy, but they're largely burned out and unhappy. And when we kind of unpack why, at first they think it's a business problem, they think that, you know, it's their team, or they think that something is just stressful and they can't sleep at night. And then when you really think about it, and when we really unpack those layers and peel that onion, they start realizing, oh, you know, I can see I'm a micromanager, or, oh, I don't do enough praise, or I don't, you know, I don't celebrate my team enough. And then when we unpack why, it can, it can go to some really personal places really quickly. It can be, my mom never praised me when I was growing up. My dad never thought anything was good enough. My spouse thinks that I should make more money. Like, and there's so many other reasons why somebody will feel a certain way and therefore treat their team a certain way. So, from a very tactical perspective, it's good for CEOs to be very aware of who they are and why they behave a certain way without being victim-blamed, without saying, well, this stuff was done to me, or that stuff was done to me, and I'm just a victim in this whole situation. Like, that's not helpful. But what is helpful is, wow, I have the self-awareness to understand that I don't value people the way that I should be, and I don't treat them with respect or like they're an indispensable part of my team because I was never treated that way, you know, or I have issues around whatever. And usually by that time, I'll recommend that they go and see a professional therapist, right? I think that's important. I think everybody should be in therapy, right? But that's the first part of understanding your own psychology. And only when you understand your own psychology can you then help coach your team into understanding why they make certain decisions or why they behave a certain way. I had a teammate, a direct report a while back, And this particular person was very misunderstood in the company, right? And they were super talented, right? Amazing at what they did. But I think this person struggled with relating to people, and as a result, it became really difficult for other people on the team to build a relationship with this person. So it was purely, you know, business for a while. And this was not a coachee of mine. This is like an actual Working relationship, right? So I started learning to build trust with this person, and I can't explain to a T, like a formula, how I did it, but a large part of building trust is really just making sure that person feels seen and understood. I think there's a lot of talk around people feeling heard, and I think feeling heard is wonderful and it's super essential and necessary. But I also think it's important for people to be seen. What does that mean? Well, it means that there's no reason outside of seeing them to make them feel seen. For feeling heard, like, there is the benefit of you knowing that that's gonna make them trust you more, and it helps you understand them deeper, and it just, it makes them feel good. But being seen is something completely different, where when you see someone, you see them for who they are. you don't judge them, and you don't try to manipulate, you know, who they are or what they've said or anything. You just see them for who they are. And I made this person feel very seen. And slowly but surely, you know, as I extended my vulnerabilities, as I extended my imperfections as a leader, this person also started opening up to me. And then I was like, oh, this is so clear as to why this person is not, you know, But it's not trusting of other people. This person's been wronged many times in the past. This person's been, you know, gone through the gauntlet and through hell and back, both in their work life and their professional, their, and in their personal life. So having this understanding helped me cultivate trust. And guess what? When you cultivate trust with one person, when this closed-up person cultivates trust with one person on the team, the likelihood, especially as a leader, the likelihood that they feel more willing to build trust and relationship with everybody else on their team grow significantly. Also, this person, for the amazing work that they were doing before, performance just went up even more. And I just didn't even think that was possible, but this person outperformed as a result and felt safe to do so. So, again, I think you understanding yourself and your psychology is the prerequisite in order for you to help other people on your team. And nobody wants to take advice from the asshole who doesn't understand themselves. They just go, oh, you're just like trying to diagnose me and you're trying to make me feel like there's something wrong with me, but you're not even aware of your own shortcomings. And so for any creator, like even for any creator or any founder, even with creators, like you have an audience and your audience will only listen to you and follow you if they feel like you're very in touch with who you are and if you're authentic and genuine. If you come across as this like fake Instagram person, content creator who just wants to sell a bunch of shit, nobody wants to listen to you. So you have to understand yourself first so that you can connect with your audience in a genuinely authentic way so that they can also feel like they're involved in your life and they can also share their life with you. And that's what, you know, forget the woo-woo fuzzies, like that's just a smart And I love that you mentioned sort of like going through therapy.

One of my favorite stories actually around this is there's a show Actors Roundtable and I'm blanking on his name. It's the guy who played Magic Johnson in the HBO documentary on the Lakers. And he's sitting there with like Samuel L. Jackson and a few other actors. And he said something so insightful. He was like, yeah, I realized when the show was going to come out, I knew I was going to be famous. But I don't know how to deal with fame. So what I did was I just went to a therapist and started talking about it and like learned how to do all of these things. And you have this moment where Samuel L. Jackson, right, who's like one of the biggest actors in the world, just looks at him and goes, wait, so hold on, you didn't know how to deal with fame, so you just went to a therapist and you were like, I'll learn how to deal with fame? He goes, yeah. And Samuel L. Jackson just looks at him and goes, that's fucking smart. Like he was just like, this is such a smart thing. And, and so, and it was just like such a great moment of like, oh yeah, like these are all these things that like none of, and especially creators, right? Like when you become famous, you have no idea how to deal with that. And so therapy definitely is a great tool. Are there other tools that you recommend to people besides that? Tools or modalities or different kinds of coaching or books or whatever?

I mean, the, Hindsight is always 20/20. So if those are you who are listening and not yet famous, go and find your group of like really genuine friends first that are there for you. Because as you know, once you have fame or you're financially successful, people will wanna be around you, maybe not always for the right reason. So establish your core group right now, right? The therapy note is such an interesting one because I think the other reason why You know, Samuel L. Jackson thought this was really fucking smart. It's because a therapist is not going to try to pander to you a certain way, the way that some of your friends or acquaintances will. They are a licensed therapist that is there to listen and help you process your emotions, and they don't care if your net worth is $10 or $100 million or $10 billion, right? They're there to work with you. A thought process with you and they're not, like a therapist who will be, you know, truly professional will maintain that kind of relationship with you. So in that sense, you actually get advice from an objective third party. So advice from an objective third party, making friends with people before you become somebody and remembering who those people are for you when you get to that point, 2 really amazing things. But those are external. The third thing you can do is internal, which is again, self-awareness and mindfulness practices. I think when people feel anxious and they don't know how to deal with fame or they don't know what to do because their company is taking off, a lot of this is because there's a lot of external pressure and there's a lot of pressure around doing more and chasing a high. And that is a very finite mindset, right? It's like, oh, you have to do the next thing and be more extreme, right? Um, not to use a not-safe-for-work kind of, um, analogy, but I think this is very similar to the porn industry where you have people that start out and they're immature and like they just, they get their big break, whatever, but they're so— the market is so saturated with you know, sex workers and porn stars, that you have to continue to do more and more and more extreme things and be willing to do things that you're not necessarily comfortable into doing, that you told yourself in the beginning you would not do, in order to remain relevant. And so very similar to that, you know, I think it's important for founders and creators to not fall into the toxic and damaging loop of just doing more and more because the fans say so, and you're doing things that are not genuine to you. You have to maintain a sense of who you are and what you care about, and remember that you're living for you and not for anyone else, right? That is actually going to be the thing that differentiates you from many people because you are living a life that is truly authentic to you. It's not manufactured for someone else to consume. So if we think about the best musicians and the best artists, they were constantly changing. Like Picasso changed the way that he painted and drew like a million times because he didn't want people to ever predict what he was going to do. You look at, you know, Michelin star chefs, they go and change their menu or they like scrap things altogether and start over something new. You look at musicians who have changed their sound and the kind of music they make over time. You look at, you know, actors who decide to You know, move out of one genre into the other. Matthew McConaughey is probably the first name that comes to mind who went from rom-coms to doing more serious, serious, you know, acting work. And so very similarly, the third way in order to deal with this kind of stuff is remember who you're doing it for. You can remember by practicing mindfulness. You can remember by meditating on Stoic concepts like memento mori. You're gonna die one day, right? Um, don't, you know, put your, uh, your hopes and dreams and the passions, you know, all, all of these things are really helpful in you remaining grounded on who you are so that you're not living a life that is for someone else. You're doing it for you.

Well, one of the things I love doing is collecting testimonials and yes, it's great for marketing, but I've realized like in the times when it's like testing or trying, They're really good to look at to remind yourself of why you're doing things and the good things that you're doing. So let's switch gears a bit now into, okay, so let's say I'm a founder or a creator, I'm listening to this, I'm convinced on operations, right? How do you actually make it happen? And I remember one of the emails that we had before we started recording, because I feel like you have this instinct and intuition to it, but you're talking about something very general and you just went, yeah, I wanted to connect with people.

Yeah.

So I had like sent like X amount of emails and did this and did like 200 calls or whatever in 2 weeks or 3 weeks. So, so actually first question too, before we jump into that is how much process is too much process? And when should a founder actually start thinking about and creating processes and not go into sort of over-engineering something that isn't even working? How do you think about that?

Great question. I am not going to try to reinvent the wheel here. I think Claire Hughes Johnson, the COO of Stripe, had the best sort of framework for thinking about this. And I don't— she probably got it from someone, or maybe she invented it, I don't know. But, um, in her new book Scaling People, Claire talks about how at Stripe they never had more than, you know, 5 processes for any given team to remember at any time. And the reason for capping it at 5 is because if you have too many processes, nobody's going to follow them. There's too much stuff to remember. And the other beauty behind capping it, it doesn't have to be 5 for you or your company, it can be whatever, but being really intentional about capping it is helpful because it really forces you to ask the why behind the process, right? You don't want to restrain your team to, you know, arbitrary bureaucratic red tape, especially if your team is early and building really fast, or you found, you know, some traction and now you're trying to really pour fuel onto the fire. I think that's— it's too early when you're pre-product market fit to have a lot of process. That being said, if you have no process or no frameworks, I should say, framework sources process, just as a side caveat, I think of frameworks as a little bit more flexible in general rules of thumb, whereas process to me is more like a list of how-tos, right, with tangible steps. I think if you're so early on and you have no frameworks in place, you end up risking compromising your team and compromising the efforts, right, that you're trying to make towards hitting product market fit or creating a really great product. As a creator. And Claire says in her book that if you have a game and there are no rules, then people are going to get hurt. And so that's the reason that you need, you know, some kind of framework in place. So for an early stage company, I would recommend being extremely methodical on how you approach answering questions in pursuit of product market fit. So again, like, Goggin. I'm not going to reinvent the wheel, but Goggin wrote a really amazing post on First Round's blog around the minimum viable test. And that is a great example of a framework that you can use early on as a founder to remain very disciplined in how you are vetting your ideas and how you're killing them or how you're deciding to go. It's not just based on gut feeling, right? And it's a great way to learn a lot about your customers and about your desired product that you're building, right? So, you know, early stage frameworks are great. Once you hit product market fit and you're scaling, that's when you really need processes in place, like actual, a little bit more bureaucracy, unfortunately. Just because as a lot of things are happening and as you're scaling really fast, people are going to get hurt if you don't have rules in place. It's also one of those cases where once you grow beyond 50 to 100 people, people need that kind of structure in order to know how to behave in the company. It also means that, you know, your culture is informed by these processes that you're putting, and hopefully by that time you have a better idea of the company you want to create and what kind of culture you want. there to be. What was the second part of the question? You had talked about like how to think about processes. What was the second part?

I was going to get to that. So I took a detour sort of like why it's important. And I love that sort of like distinction between process versus framework. So let's say you're working with, or you're coaching a CEO, or maybe like working in a company and they have the sort of like frameworks, Then they find product market fit and they start adding people, right? Like they go to like 4 or 5 people, 10 people or whatever. And maybe you can like share some examples from either like stuff you did at On Deck or your work with Matt. At that point, how do you think about like starting to build the sort of like operational side or operational framework for the company? Like what's the like tactical like 30, 60, 90 day thing that happens or the strategies that you use?

Yeah, the 30, 60, 90 days is going to be hard because it's going to be different from like company to company, right? Like you're not going to have the same 30, 60, 90 days for a hard tech company that's launching a rocket to the, you know, outer space versus like a SaaS product. So we won't go there. I think it's really important to make sure that your team understands what the mission and objectives are. Before you even do anything else, in order for people to know how to behave and where to inject process, you have to know what your mission is. If you're trying to add process before you understand what your mission is, like, it's not going to work. The example I'll give is from our time at Outback, right? We had a vision of creating the next, you know, Stanford in the cloud or democratizing access to education. slash community and network regardless of where you lived. And so my job, right, was to help build the process around launching all these fellowships. But I didn't know that that was my job. Like some— so I think Brandon, my manager, was like, we're going to launch all these fellowships. That's your job now. He didn't say build the process around it. He just said go forth and launch, right? Of which ODP on that podcast was one of them. So I took a step back and was like, okay, this is a really big goal. How am I going to accomplish this goal? And hopefully, of course, the goal is informed by the objective, which is informed by the vision, which is informed by the mission. Like there is a hierarchy that has to happen and preferably this happens once you've found product market fit. But in my case, I was just handed, you know, something to do. They said, this is your mission, right? All right, this is my mission. It's tied to the larger company mission. And I quickly saw there's no way that we could do this with a small number of people. So the minute you start introducing people, right, or the minute you know that there's something that has to be replicated, those are usually good signs for a process that has to be put in place. So we had something at Onda called PEMDAS that the launch team built and that I oversaw. And PEMDAS was basically like this huge checklist of All the things that had to happen in order for a fellowship to launch. You remember PEMDAS, Sachit, because you used it to launch OVP. And it started, you know, all the way from the very beginning when a program director joined, all the way to when we launched the fellowship and a little bit after that.

Mm-hmm.

The other kind of sign for adding process in is if things have to be done in a very tight timeline. So as I talk about Pandas, it reminds me that some program directors had 12 weeks to go from joining a company to launching a profitable, you know, essentially a product, like an arm of a business, or, you know, where they were the CEO of their fellowship. That's kind of how it was framed at the time. And so, you know, if there has to be stuff that's done really quickly, you have very little space for error, and you have very little room to deviate from what's already being done, right? And program directors can have, in this case, they have their own kind of flexibility to adapt as they needed it, but what was important was writing everything down so that they knew, oh, here are the steps I didn't even think of, right? Because I'm joining a new company, and I don't even, you know, know all the people on the team and who I'm supposed to interact with whom for what. And so that also became a really great sign that we need a process in place. And then finally, just in terms of hiring discipline, I think having processes tells you, oh, this is the amount of work that somebody is expected to do. Here are all the things that need to be done, and let's, you know, go and give them, you know, this number of people that they need in order to run their programs and/or like to build their products. And so From a hiring standpoint, I think process, that's also a good, you know, practice when you're hiring a lot of people and you need to know what the headcount should look like. So those are a couple of things I would look out for when it comes to knowing when to implement process. And then in terms of the how, it's the question I always ask myself is, what needs to be true in order for this to be true? So if you want Y to be true, what is the X that has to happen? So in this particular story, if I wanted to launch 20 fellowships, what has to be true in order for me to launch one fellowship? In order for me to launch one fellowship, what are the different moving parts? And so I made it a team effort where I wrote to every single head in the leadership team and I said, I need you to send me a list of all of the things that you need, that you do to be involved with the program director when launching a fellowship, right? And not only is that good for the program director who is now going to understand that that is what, you know, that is a resource there and available for them, but it's also great for you because now you have a point of contact with each person and you don't actually have to go and like do a bunch of one-on-ones in order to meet all the new people. Like they already know that you're kind of the go-to person and they know how to interact with you, right? So collecting all of that information took several weeks. Because it was like this hairy, audacious, a lot of moving parts. Trying to figure out the order was also really difficult. But, you know, it was a lot of long nights and organizing all the information. And in the very end, it worked, right? Like we launched 20 fellowships using PEMDAS, probably more actually, but 20 while I was there.

One of the interesting things when I'm thinking about PEMDAS is And I'm sort of relating to this concept that Matt talks about, which is really like finding your zone of genius. And it was really interesting to see how sort of PDs adapted the process to what was either their zone of genius or like what they were bringing into the fellowship, right? Like for example, like what I'm thinking about is, let's say like KP, for example, with ODNC, the No-Code Fellowship, he was just really great at community and he brought that into it, right? Candice with Climate, like had the operational experience. And so she was really able to like operate well. I came in more with probably more of the expertise in podcasting and at that fellowship than a lot of different other ones. And so when you're designing this process, how do you think about sort of like the adaptability of it based on the person or the people with, including like team members that are part of the process?

Yeah, what a great question. I think That's why, again, I'm going to relate this to what I said before, where it takes people on your team in order to have a viable product, right? Or to have a viable business or a company or startup. I think in this case, when we talk about PDs, program directors, they were in a lot of ways the CEO of their own fellowship, right? And it's not like a PD was launching on their own. They were launching with a team to support them, right? or in most cases, one person that was the operations person. And so processes are, and frameworks are great in that they're flexible and they don't assign specific roles to people. It's your job to take the process and figure out which, how to divvy up the work. And so, you know, in KP's case, he was so good at community. And so I never had to worry about whether he was going to fill his fellowship or not. But as a result, he was not necessarily, you know, he didn't love doing the operations parts. And so he was like, Gina, you do it. And then whoever, like, my ops person is, Chanel in this case, who is just a beast of an operator and great at community and great at everything, like, she's just amazing and so talented. Like, that was a great fit, right, for them to build together. And then For you, you had— you brought in the expertise side of it, and you also had some community you brought in as well, but you didn't love the operations part of it. So we're like, all right, Nancy's really good at this, so let's have her do that. And again, she was awesome at it, and she was on top of it, and she, you know, did the parts that you weren't energized by doing. And hopefully when you're assembling a team, you like look for people who are energized by those things. So, you know, look for the people who love talking to people, who love putting processes together. I mean, Nancy co-wrote ChemDAS. So, you know, that if that says anything about how geared someone is to tackle operational components or not, like, it's great. The final thing about this, again, going back to people make up your team, and so you have to take care of people. is you have to make sure that they don't feel like this is bitch work or that their work is not important, right? In the cases where I would see program directors and operations people not get along is whenever operations people felt like they were doing grunt work that was not valuable or useful, right? And so it really comes down to how that person communicates, you know, how the, how the PD would communicate with the operations person. Are they really a team? Like, or are you just, you know, hiring Basically a glorified assistant to do work for you. Like, that dynamic would determine whether people got along or not, right? Are you my peer and equal, or are you somebody who I expect to just do work for me? And that will change, you know, the outcome. So I, I once had a really amazing person I worked with, and she did all sorts of work, from really important work to more menial kind of work and everything in between. And she always did it with an amazing attitude. And I remember asking her, why, like, do you love doing all of this? And she was like, I love doing probably about 85% of the work that I do, and especially when it's hard and challenging work. But, you know, for the rest of it, I have a good attitude about it because I know it has to be done. I know it's important for the company. It's the plumbing. Of the company. It doesn't work, and the house doesn't stand if I don't do these things. And so, I know because you, Regina, have made me feel like this is really important work, and it's the stuff that allows us to continue and persist. And you've made that clear to me week in and week out during our one-on-ones. So, yes, I'll do that work, and I love it, right? I love it because I love this team.

Yeah, it's like, care about the person, but also have respect for what they're doing because Whether it's an EA or a different role, it all is important. And this question is for probably like all the creators that are listening, because I know my creators and they don't usually like doing operations. In fact, when I've seen some of the stuff that Nancy and I worked together after on Deck and she helped us build, creators are just literally like jaws on the floor in terms of the way we've like systemized certain things. And so let's say I'm a creator and I'm looking for sort of like that operating partner, right? You went through sort of like that transition from, I think, chief of staff to CEO yourself, and then you've also facilitated this transition of, I think, EA to chief of staff to CEO for certain other people. Can you break down sort of what is the differences in these roles? And if I'm a creator, how do I understand which role to bring in? Or if I wanna have someone go from the other, like how do you even think about that?

Great question. Typically, I'm not going to break it down from title to title because I think titles are pretty arbitrary. I've met some incredibly shitty, you know, C-suite people that are like not organized. I've also met some really amazingly talented executive assistants who like, you know, could easily have been an amazing, you know, COO, right? Like, so let's ignore titles for a second. Let's just talk about the different stages of an operator. So when someone is starting out and they're kind of learning the ropes, I would consider that entry level. So this person is really good at taking tasks that are already spelled out for them. You give them a task, you tell them how to do it, and they go and they do it, right? That's level 1, and that's pretty entry level. That's pretty junior. And I don't think there's anything wrong with that. I think Everybody has to go through that at a certain point, like especially if you're early on in your career or you've just pivoted into, you know, startups or whatever. Like if you've changed careers, you're starting from the beginning, you're learning again. People that move past this level into level 2 are people who can start taking on tasks without being told how to do them. They're resourceful, they know how to think critically, they know how to use resources like Google or ChatGPT. To look up how to do something, and so that becomes the next level. This person is now still being handed tasks, but they can figure out how to do it on their own. If they don't know how to do it, they'll search for it, and the person they work with doesn't have to teach them how to do it because they know that it's going to get done. That's level two. Congratulations, you graduated. Level three is when you start taking on tasks that are not. necessarily clear-cut and spelled out, as in like you could type an answer, like type a question into Google or ChatGPT, and it won't give you a direct, here's how you do everything step by step. It's usually involving a bigger project with more moving parts versus one task start to finish. And that person will now have to start piecing things together, using critical thinking and trying to assess what is in the company's best interest, and how can I prioritize accordingly? How can I, you know, make sure that I'm balancing my tasks well? That's level 3, where you start taking on projects, right? Level 4 is when the person that you're working with can just hand you a project and then say, here's like a project, or here's an initiative. You figure out what the actual goal is here, and like what Or sorry, the other way around. Like a person hands you a goal and they say, here's the goal, you figure out what the project is and how to get there. And that is like the next step of an operator. So if the goal is, hey, we have— this is a really shitty goal, by the way, but if we, for the sake of the argument, like our goal is to raise a Series A by like, you know, summer. Okay, what has to be true in order to raise Series A? You have to go and do that thinking now. Okay, well, What do our metrics look like? What do our financials look like? What is our— like, it's usually numbers-based. And so, and by the way, as a caveat, as you see, like, each level going on, we're on level 4, and with every level, this person has to have access to more and more information. So it also depends on how much information you want to share with them. By level 4, if you're telling them, here's a goal, go forth and do this thing, you have to be willing to trust them with the numbers. Like, let's say Hey, our goal is to raise a Series A, $20 million, let's say $10 to $20 million. You have to be able to tell them, hey, these are where our numbers are, here's our revenue, here's our P&L, and here's like what needs to happen. That's a lot of trust. So again, it takes time for people to get to that point, right? But that's level 4. Now you have a goal. Now you have to figure out how to get there. And I think you've really like made it when Even before the person you're working with thinks about it, you're able to see the needs of the company. You're able to forecast it very similar to bias towards action. But bias towards action is really task-oriented. And I'm talking about vision-oriented or strategy-oriented. You're thinking way ahead. You're going, hey, for like we're in 2023 right now, for 2024, like mid-year to end of year, like we have like this thing is going to happen or this technology is going to be in a certain place. We need to start aligning, you know, the pieces to get there. I know this incredible chief of staff. She's probably the best chief of staff I've ever met in my life. And she's the chief of staff to someone I coach. But she works in a heavily regulated field. And when she first started out, I would say she started out at like a level 3 where she didn't have to be taught what to do. She could look things up. And that's what really made her a great chief of staff. She was able to go and like search for how to do something. And so her exec could just tell her, hey, here's something we need to get done. She'll go, okay, and she'll go and do it, right? But, you know, this chief of staff was so good because she started thinking— she started taking over strategy, she started taking over planning, she started looking long term. And she was like, I love this company. I want to be here for years. And this is like where I see the regulatory kind of landscape going. So now we have to start thinking about strategy and planning and I have to get everybody else on the same page. I mean, and when I talk to this, you know, exec who sees her like this person was not threatened by their chief of staff at all. This person said, hell, if in 2 years this person is still doing this and is doing it even better, I would happily give up my C-suite role for this person because they're probably better at that role. I mean, that is infinite thinking. That is somebody who doesn't see it as zero-sum. That is somebody who is like, there's something else out there for me. And this is like an amazing move for this chief of staff and everybody wins. So those are the different tiers. I would say for operators, I need to write that into a write-up actually, because it just kind of lives in my brain right now while we're recording this. And, and then I think in terms of creators and founders, especially for your audience, all these creators who are so creative and love doing stuff, but they hate the operations part of it, you have to create an environment where that's possible. That means you have to be so clear on your mission. You have to be so clear on the trajectory. You have to be so clear on explaining to people, you know, what needs to be done and why. Only when you're super good at that can you hire people. That can operate and do the rest, right? Because they're going to see something that you have that they don't necessarily have, which is clear vision. Operators, you know, sometimes just want to do the execution part. They don't want to, you know, necessarily think unless they're like on level 5, like where they're already, you know, thinking ahead before you. Like hiring somebody that fits into like level 3 is like Really, really, really solid. They're also going to be expensive. So that's something to consider, right? You can't expect these amazing talented operators to come cheap. So things to consider.

If I'm a founder or creator listening to this, this is actually, I think this is the same question asked in 2 different ways. So feel free to answer in whichever way you'd like or both. If I'm a founder or creator listening to this, You mentioned the importance of the environment, right? How can I create the environment to both hire and bring in and sort of have the evolution of this person from, let's say, like level 1 to 4? And then if you're an operator listening, how can an operator go from level 1 to 4? Sort of what are like mindsets or tools or tactics that they can use to have that evolution?

Yeah, these are really good questions, Sachit. They're really excellent. I think for operators, I'm going to talk from the operator lens first because that's, you know, what we were just most recently on. Operators need to have a constantly turned-on learning mindset. They have to be willing to learn anything and everything. They have to not be afraid of not knowing something because the only way you get better is if you learn, right? And I have seen operators learn how to you know, create, uh, like look over legal documents, send out all sorts of fine— like do financial stuff, financial projections. I've seen them learn how to do inventory management, like logistics and everything in between. It is the best job to have if you want to learn how a company is really running, right? And so you have to constantly have an operator's mindset, um, and a learning mindset. You cannot ever, you know, allow your fear of not knowing how to do something bar you from learning how to do it. Learner's mindset is number one. I think on the reverse, for creators and founders who are trying to hire and retain this kind of talent, you have to make it okay for them to constantly be learning. I think with every operator I've ever worked with, I have done my very best to try and remind them, hey, you're not perfect, and I don't expect perfection. I expect hard work and persistence, right? I don't expect you to already show up knowing everything, but you, you know, hopefully will not make the same mistake twice. You will hopefully be curious and always like be willing to dive into things to learn new stuff. And the most important thing, even beyond what I just said, the most important thing for a trader or a founder to do is take interest in your operators. Help them learn, right? If you can help them learn, guess what? You don't have to do it. Like, they're already going to feel great learning and doing more, and you get to assist them. So the best execs I've ever worked with, um, both in a working capacity and a coaching capacity, have genuinely invested in their operators. They go, hey, How can I help you learn? How can I, you know, leverage my network to help you succeed? And there has to be this infinite mindset of positive sum where you're not thinking, oh, if this person learns all these things, they're gonna leave and start a copycat of whatever I'm doing. Like, that's not the point here. The point is, if you treat someone right and you invest in them and you make sure they're not a taker, you're gonna end up so much better off. You're gonna have a great, amazing relationship with this person. This person is going to go on to do amazing things. You have to be willing to understand that they're not going to be working with you forever. And so you might as well set them up for the best success possible so that they understand that they benefited from their time working with you and you get to walk away from that, you know, relationship as friends. I think that's so important. But you should never be a founder who or a creator who only sees them as dispensable or sees them as replaceable or sees them as cheap talent or sees them as whatever. And like, you have to be willing to invest in them, not because you want returns from it for your business, but the first and foremost reason that you are investing in them is because you genuinely care for them. You ask them how they're doing, you ask them how their life is, you ask them, you know, are they learning? You ask them about where they want to be in their career. You make that You, and you don't give them all the work to do that. You basically say, hey, there is this person in my network who I think would be an amazing mentor for you. Let me, and I already asked them and I reached out to them and I said, there's this amazing talent. Would you like to have mentoring, you know, with this person? You don't make them go, oh, well, you know, I know these amazing people, but you're not important enough for them to rub elbows with you, so you can't be around them. And like, that's the number one way to make Talented operators quit.

So it is by not fooling them, right? And one of the hacks, it's not even a hack, but it sounds, I'm just using that word honestly, is whenever I bring in someone in that role, I find the best course for that position. And I just go, okay, I've bought this course for you here, go through it. And also, can you teach me? Because one, it shows them that you care, but also like gets, see, like it tells you if the person is actually interested in learning. And whenever I've done that, the operator person has come back with like, this was amazing because you're showing like you're investing in that learning right off the bat.

100%. 100%. Like, I couldn't agree enough. There was a coachee that I had who originally coaching was just for them. And the chief of staff joined a little bit later. And this coachee went out of their way to say, would you go and talk to my new chief of staff, and would you, you know, share your tips and your learnings with this person? And I know I wasn't the only person that this coachee approached to set up these relationships. So within this chief of staff's, this new chief of staff's, like, first couple of weeks, they managed to meet all of the people or many people who this exec cared about so that this chief of staff had an avenue of support and could learn from any of us. And that's the kind of care that wins loyalty, that transcends any company or any project or any initiative. These people will follow you anywhere you go because they know that you invested in them and they are going to invest in you as a result.

So, so let's say I've hired, brought in someone right at one of these levels and I'll just sort of like throw out some concepts. I want to kind of learn on how to actually make this happen. So there's like concepts like shadowing, tactical empathy, all these different things. So if some, if a founder or creator has brought in this person now, what does that 30, 60, 90 day look like? And maybe it's not even that in terms of getting that person up to speed so that they can become the best operator working with you.

So you've already mentioned a couple of really good practices that I think have a lot of merit. So the first one, Of course, the concept of shadowing is basically having your new hire learn how you think, behave, and act, right? I think that's really appropriate for, you know, operations-type folks. I also think it's great if you're making a hire who is tasked with, you know, running a specific department or whatever. I think it's great for them to sit and like watch how you do things. But I think you have to go the step further. By making sure that you do open up an avenue for them to ask great questions. So as I mentioned earlier in the podcast, having that asynchronous Slack channel where they can ask any and all questions is really important. Having an onboarding buddy, if possible, somebody that's been there a little bit longer than they have, is really helpful. And I would actually, you know, argue that if a person has been around for, you know, 3 weeks, I think that person already knows a lot more than the new person coming in, and therefore they can work together to onboard this new person. So it doesn't have to be somebody that's been with the company for 6 months to 12 months or like longer, right? It can be really short. So an onboarding buddy, an async channel, having that person watch how you work. And I think it's important to mention, you know, in this environment where we have a lot more hybrid work situations or remote work situations, shadowing can feel like a really daunting Sort of experiment where it's like, how do you follow somebody around all day and watch them work if you're not in the same location? Well, the good news is instead of shadowing, you can do what, you know, we would call coworking sessions where during the first, you know, several weeks you just sit down with this person and the two of you like work together silently. And that means you like share a screen. You explain the processes that you're doing, and then that person can ask questions. I would avoid doing coworking time that is unstructured. So I've seen coworking sessions where a person just comes online and then they share their screen and they're answering a bunch of emails. And there's some merit to that if you expect like an EA, for example, to answer emails, you know, according to your voice or whatever. But good EAs and operators and chief of staffs and so on will learn Even just by reading, you know, like for example, when I was a chief of staff, I learned how to write like my boss by, you know, just reading a lot of his emails and learning that he put double spaces after periods and learning that he liked using the word therefore and so on and so forth, right? I didn't have to sit there and actually watch him write emails in order to learn all these things. And so I think all of those are valuable tactics. I think, again, During that onboarding phase, investing in developing a relationship with that person is important. So if I were to start a company and it was new and I was bringing on my first employee and I knew that we were going to work together in a really, really close, tight capacity, I would try to make some kind of effort to see that in person for a couple days at least, just to bond. And the purpose of that is not necessarily to get them to work harder or be more dedicated to the company. That's a nice bonus. But I think the purpose is to get to know each other as deeply as human beings. So, there was actually someone who I brought onto my team and they, like, we both lived in different places, but we met in a kind of middle common ground place and we spent, you know, 3 days together and we didn't we did do work things, obviously. We worked together, we sat in the same space, and it didn't have to be a long time, but we did really fun things together. We did extracurriculars together, we went out for food, we had mutual friends, and so we like went and hung out with them. And, you know, it was a general— generally speaking, like an environment that fostered trust between the two of us as human beings. And this person got to see how I was as a human being, not just as their boss or as their manager or whatever, the leader of a company. It's just, you know, they saw me for who I was, me. They got to see how I interacted with my husband. They got to see the things I cared about. I got to have, you know, pillow talk with them and ask them like at night, hey, what are the things you care about? And these are the kind of conversations that I think happen really organically when you're in person. So The good news here is you don't have to spend 90 days in person with your new hire, but I think even just having a small stint is a really nice to have for like a weekend where, you know, let's say you cover their childcare, you spend time with them, you have like a loose itinerary of things that you both have in common that you'd like to do together, and then you also make time for these personal deep conversations of like, what is it that you want in life? What is it that you care about? Just tell me, you know, how you can see our company doing better. Tell me how you can see me doing better. How about you? And I have these things that I want for you based on the things that you care about. That's how I would approach onboarding. And yes, it's time intensive. Yes, you have to give a shit. Yes, it's a lot of work, and it's a lot easier if there's like this like magic wand that you can wave and say, do this thing, and all of a sudden all of your direct reports will be fantastic and amazing. But it does take effort and time and energy and attention. But as a result, you have loyalty for life from some of the smartest people you'll ever work with.

And as a follow-up to that, this is a question from my friend Zion, who was very excited that I was interviewing you. So let's say you're doing all these things, right? And especially if you're a creator like doesn't really know how to operate, or you're not really like looking at feedback and all of these things. How do you know that someone is on track or not so that you don't end up sort of like having this thing where you check in 30 days later or 45 days later and the person hasn't absorbed anything? So what does that sort of like feedback cycle look like?

Yeah, that's why touchpoints are, are really important early on. I try to give my, you know, my new hires feedback within the first Several days that they're there. You know, feedback doesn't imply that somebody has done something greatly wrong. Feedback is just your take from where you're sitting on a situation that involves another person and how they are performing or what they're doing. So, you know, if, for example, I brought someone on and they were Meeting my expectations about 80% of time, meaning they did all the things that I assigned them to do, but maybe they were moving a little bit slower. Maybe, you know, I messaged them on Slack and they don't get back to me until over 24 hours later. These are all things that you can communicate, right, early on and provide feedback. You should never go more than a week And I'm late even if you ask long for like early hires in terms of like how they're performing and how they're doing. And a lot of these conversations will organically come up, which is the nicest part. You don't have to force it to happen when you have constant check-ins. If you're having one-on-ones with them, when you're checking in on their progress, where you're assessing how they're feeling, where you say, okay, let's sit down and come up with a game plan for how you're going to succeed in this role. Let's talk about, you know, our, you know, email cadence or Slack cadence, whatever. Like, there's always going to be points of improvement where you can say, hey, you know, I love that you've just like really gone heads down and like are doing all sorts of stuff and it's only your first week. I just wanted to share with you that, you know, for our company, because we make changes so often and so quickly, I think it's really important for us to have a cadence where we're communicating frequently and quickly, and you're not just disappearing for an entire day, because the chances of something changing in that 24 hours that you disappeared are pretty high. And as a result, I don't want you doing a bunch of work that, you know, is thrown away because we couldn't reach you. So, what is a way that we can come up with a solution together? So that we can have more constant contact? Would a daily standup in the morning before all of our meetings be a good touchpoint for us to like get updated? Is it a matter of, you know, using Slack more often? Is there, you know, a preferred method by which you want us to communicate, or are you okay with us using this channel to work together? And they'll, you know, during their first week, they'll Be receptive to feedback, hopefully, or, and if they're not, that's a good red flag for you to let go quickly. But chances are they'll say, oh my gosh, I'm so sorry. I'm just like, this last company I worked at, they were really, really big on just like getting as much work done and talking less and doing more. And so I just went deep work. And so I'm still learning how to work in this new environment. Thank you for letting me know, right? And you can even say, hey, what are the things I can do In your opinion, to help facilitate that communication? Or like, I would love to, you know, be on the same page with you, so what are some things you think I could do? And that forces them to think about what it's like to be in your shoes working with them, and that overall cultivates a lot of tactical empathy.

What I love is so much of this comes to just creating that trust and like actually caring about the person.

It really is that simple. I, I, I, I know it doesn't sound revolutionary or anything, but that's really all it is. Can you care about people and relationships?

I'll bring this sort of like to the thing that we started with, which is sort of like this like radical, crazy idea that I have. And I'd be curious to hear your thoughts on this. When I look at sort of like the journey of creators, right? One of the patterns I've identified is a creator will start something. It takes like 1 to 3 years to make it successful. And when it starts getting to that point, They're like, all right, I'm done. And they'll kind of like move on to the next thing and burn that thing down because that's the evolution of their creator journey, right? And so if someone's a creator and sort of like has that kind of a mindset, can they actually start bringing in this sort of like operator kind of person, establish the trust, establish the care so that when they want to move on to the next thing, instead of burning it down, basically sort of the operator can take over and then run that thing. And you can almost play this infinite game of doing more and more creative projects. But when you're moving on to the next ones, you're not really, you're not burning down whatever you've done because you've built the team or you have the operator to actually run and handle that.

100%. I mean, I, my first business is still running to this day because I did that, right? I started it in 2012 and I passed it on to my former employees in 2019. I sold it to them in this case because I thought to myself, do I want to still be attached to this, or is it possible for me to completely let go in order to start my new thing? Because I, in this case, I was moving from completely different career into a new sector, right? I think the idea of creators starting something, building it out, making it amazing, and moving on to something else Uh, is common. And I think the approach by which what you choose to do with this thing you've already started and is now successful depends on the reason for you moving on. Sometimes creators move on because they're— they feel like that's the end of that chapter and they don't— they're ready to just part ways with it. In which case, great. Like, go and find someone to micro-acquire it or bring someone on who is amazing. You know, trusted person. It's basically like when you're a startup founder and you have a new CEO come and take charge and you become the chairman or chairwoman of your company. Like, that's totally fine. If the idea, though, is that you want to move on to something else and that you don't— like, you feel like that stint was a good run for what it was and now you're ready to move on, I don't think there's any shame in shutting something down either. Because again, shutting something down and perceiving it from a negative lens implies that you should never let go of things that are amazing and great, right? Like, and, and for what purpose? To accumulate more? Like, what is the purpose of holding on to it? Now, if it's really like, I created this amazing community of people who genuinely care about each other and care about this thing that I've created, I don't want to leave them behind and I want someone to keep running it because I'm passionate about this, but I'm ready to be a participant in this community rather than leader of this community. Great, keep it alive. But if it's like, I made something great for what it was, I think it's time to wind it down. I don't know if there's somebody who I know today who I trust to, you know, Take over, I think it's okay to walk away from it. Because again, like, what has to be true? Again, it's always that question. What has to be true in order for someone to properly take over? You have to have deep, deep trust with it. If you think you have to have deep trust with, you know, people you hire, you have to have deep trust with people that take over. That's one thing. You have to still be willing to have your foot in that door. Which can be really hard for some people. Like, some people want to have a clean break, and they don't think it's possible to move into a new stage of their life if they still have a foot through that door.

Yeah.

You have to be still in some ways invested in that person and their success, because here's the danger. If you have someone take over and you don't actually really care about the community or about the product or whatever, You risk becoming a transactional relationship with this person that's taken over. And just like it's really hard to build trust, it's easy to break it. You know, in this case, you've built trust with this person and it's really easy to break it if you get upset and you blame them for like, for the company not doing as well or the community is taking a different direction from you. It's really hard. You have to be ready to kind of give it a life of its own if you're gonna pass it on to someone else, so.

Which again goes down to psychology of like learning to let go.

Learning to let go, learning that the best thing that you are ever going to start is not the thing that you're working on now, which sounds so crazy for a lot of creators and for a lot of founders. It's like, what are you talking about? I spend all my hours, all my waking hours thinking about this, working on this, breathing it, eating it, sleeping it. And yeah, that's amazing. And I'm not saying that the thing you're working on is not great right now. It is. But I'm saying that in order to pursue the great and to continue this fight, there has to be a mission that you're living for, and it never stops. You just keep going, right? You're always gonna do something greater. And if, if you think the thing that you're working on is the greatest thing now, you've essentially capped yourself on how amazing you can be. I also think it's one of these things where people should never be afraid of approaching and learning new things. Like in my own career, I started off as a music teacher, then I ran a music school, then it became the best music school in Southern California, and then I gave it all up to do what? To go into tech? Like that was crazy. And then I started a wedding vendor CRM business and then taught myself how to code and then got a job in operations. Like, and it felt weird being 27. And an intern again, working with like 20-year-old kids, right? But I was willing to do it because I was willing to reinvent myself. And then I didn't even know what the chief of staff role was when I like applied for the job. I just was told that I would be a really good one. And I learned about it, like I read voraciously about it until I learned what it was. Then I didn't know what a COO's responsibilities were. I didn't even know what coaching really was. And now I'm a coach. So, You can't be afraid of burning something and going to something new, especially if you're ready for something new. And now people ask me, Regina, why are you going into direct-to-consumer, like, space? Why are you doing CPGs, consumer packaged goods? Like, that's crazy. You're trading out bits for atoms again. And I, to that, I just say, well, People look crazy until they're not, right? And then people go, I always knew that you were gonna be able to, you know, succeed in this realm. And no, you didn't. I couldn't, you couldn't have known that I was going to, 'cause I didn't. So, you know, life is all about learning and getting better and making relationships along the way and collecting really good stories so you have a cool eulogy when you die.

Yeah, I love how all your answers are setting up like so nicely for the next question. We could keep on going on this, but we'll sort of bring this to a close. The thing I always like ending with is what are you most excited for in the next 1 or 3 or 5 years or whatever timeline you want to, you think about it in?

What am I most excited for in what way? In my life or in general, the world?

Yeah, it could be in terms of like what you're working on, the world or whatever. Because you mentioned the CPG company, I didn't know if that was public. So I know that's part of it.

Yeah, yeah. So I am currently working on 2 things. I'm still coaching full-time right now, and I have this amazing small group of coachees that I work with, and that's been really fulfilling for me. So I found, I think, something that falls into my zone of genius because I'm helping these people build tactical empathy and learn about themselves and also make really great tactical business decisions as a result of knowing themselves very well. So I'm still doing that. But I started another company back in February. And it's a company called Secret Sauce, where we're, you know, the first online platform that— and marketplace that basically curates all of the best sauces from small batch sauce makers and restaurateurs around the world. And we send sauce boxes to our users based on their taste palate and their dietary needs and their You know, cooking styles. And this had nothing to do with any job that I've ever had in my life, right? Like, I grew up in the restaurant industry. Like, my father worked in hospitality and he was a busboy and then a server and eventually started his own Vietnamese restaurant in Redwood City. And so that's the extent of, you know, restaurateur kind of life that I've had. But I found a question in that that got me curious, which is why You know, I'm excited to be a founder again. And people are like, wait, what do you mean you're going into food and beverage and consumer packaged goods? You don't even know anything about it. And that's the thing with operators. We are constantly learning. We're constantly exposing ourselves to something new. We don't need to stick to what we know. And in fact, like the best operators crave learning new things because it means that they're doing better and they're becoming better. And with that, like, what am I excited about? Like the internet. I know the Internet of Things was invented so long ago, but The internet gives us access to just, it's a crazy amount of information, but you can, you can get, you know, the equivalent of, you know, several bachelor's degrees just by going online and reading and listening and listening to podcasts like yours, Sachit, and like consuming creator economy stuff. Like, I, it just is so crazy to me that, you know, we live in this day and age where anything is possible 'cause you can just constantly teach yourself. You can reinvent yourself. If you don't like your career, you don't like your life now, you can start over. And I understand also that this is an incredibly privileged thing to say. There are some people that don't have the luxury of like spending all day listening and learning and doing things and consuming stuff. I understand that. But I also think, you know, by and large, for most people that are listening to this podcast, you have the ability— like, you've probably listened to an hour-long podcast at this point. Like, you could be doing anything, but you're learning. Right. And that's really amazing to me. So going back to Secret Sauce, I'm excited to go into a completely new field and see what I can build here and then see what I can build after that. I'm excited for that. I just turned 30 recently, and so I'm excited to hopefully become a mom in the next couple of years. Like, I'm at the stage in my life right now where parenthood is exciting of a thought, and I'd like to See where that takes me. It again, like, I don't know how to be a mom and I don't know what that's like or anything, but I'm excited to learn about that. And again, like, that kind of goes to human resilience and human knowledge. Like, there's so many things that we do throughout our lives that are kind of forced upon us because of one reason or another, but we've always come out on the other side of it. You know, if you're listening to this, you are alive and you've survived stuff. That's really cool to me. Um, in the startup space, I mean, gosh, like everybody is talking about ChatGPT, but really, like, I just think having access to all of this information is one thing, and then having access to information that is organized in a way that makes coherent sense is like something else. So I'm really excited to see how technology can enable us to make connections across different disciplines that we've never been able to make before. I'm excited that there is a pro— like a, a product that basically has infinite knowledge, like infinite human knowledge, things that have already been recorded, um, that has the, like, the ability, theoretically speaking, has infinite memory to make connections across all of the different disciplines that we otherwise would not be. It's basically Roam Research or Obsidian on steroids. Um, I'm excited for the innovation of you know, this technology basically being able to produce full-on web apps, which basically means non-technical founders and creators are able to have access to a level playing field of making technology without needing a technical co-founder. I'm excited for that. And I'm excited for a world where I think ultimately, you know, access to information is getting more and more democratized day by day where you, you know, and this is not just information that you're consuming, but also, you know, the kinds of products that you're exposed to. Direct-to-consumer was not nearly as big of a thing. Like, I mean, even 10 years ago, right? Like the— if you think 15 years back, the concept of buying something online was scary for people, right? So now as creators, we get to have exposure to this whole new audience, and we don't need to go and, you know, sell ourselves to like these multibillion-dollar corporations in order to get something off the ground anymore. So I'm excited for that. Gosh, I'm excited about so many things. I'm excited for bootstrapped businesses. I think that this whole SVB thing recently has really woken— and then also that market in general has woken people up to the fact that if you're taking venture money from like a tier 1 investor, they're going to expect like a $50 billion outcome, you know, in order to make the returns make sense for their funds, which is totally fine and like that's great. But majority of us are not gonna be building $50 billion IPO companies, and I don't know that it's healthy for a majority of people to do that. So in a world where there's so much technology and so much information available and so many people that wanna just do and create things, I'm excited to see people start prioritizing profitability and building products that actually work and last versus like these fast companies that are built and then fizzle out like 10 years later because of one reason or another. So all of those things are exciting. I'm excited about, you know, the progress of technology. So my, my husband, you know, is a software engineer and he works for a company called Zotara and they do battery testing and modeling. And in a world where, you know, climate change is very real and we are going to have to pursue renewables with much more urgency, I'm excited to see technology come about where it makes all of this possible. So with, you know, batteries, we have the risk of things exploding or not doing well under certain pressures or environments. And so the company that my husband works for, basically is able to model like what happens over a battery's lifecycle. And I think as we have these kinds of innovations, like it makes having renewables more and more efficient and more safe. And I think the more we move towards that, the better chance we have as a species. So, you know, I'm excited to see what these smart people with all this information, with like the ability to create amazing products and have like the larger scope of humanity kind of in mind, what they can do to make really amazing products.

Yeah, I think especially that combination where you said with like the bootstrap companies where you can do what you want and sort of ChatGPT and AI. I really think like the next 10 years, like there's been this whole thing of execution is more important than ideas and all of those things. I think the next 10 years could be like the age of the ideas people, because now you can actually go from idea to full-fledged product to like full, like something completely built with just AI. And I think that's going to be really magical when people explore that.

Yeah, I mostly agree with that. As an operator, I need to say that you still have to execute in some ways, but execution has now definitely become a lot easier compared to what it was before. I agree with that.

Yes. And if people want to dig in more, uh, the website is coachingfounder.com. I love all the resources that you have there. Anywhere else you want to shout out or want people to go if they have any questions, if they want to reach out to you afterwards?

Yeah, they can connect with me on LinkedIn at Regina Gerbeaux, G-E-R-B-E-A-U-X. Just send a note that you found me through the podcast and happy to connect in that medium. And yeah, like you can follow me on Twitter. I will be posting more things that are SaaS related and also coaching related. on there and in general, just what it's like to create a company again as, you know, a third-time founder.

So can people buy the sauces yet or is that not public yet?

It's still in alpha right now, but I'm working on a website eventually. The domain that is reserved is getsauces.com, but it's not up yet. I have a secret Tally form that is floating around on the internet somewhere. So if you message me for it, Yes, you can actually order a Sauce Box. I will send you the link. But I just had this influx of orders that I like have to fulfill. So it's a good problem to have. But yes, if you hunt me down, I will send you a form and you can, you can, you know, be one of the first people to say you got a Sauce Box in the earliest days of Secret Sauce before it becomes a big company.

Message, message, Regina, for the sauces. Thank you. Also, just thank Lucas, Sabrina, and David for all the research that we did. before this, and thank you so much for coming on.

Thanks for having me.