When to Hire Fractional Executives Instead of Full-Time

You should fire yourself from doing all admin work. Anything that is repeatable, but yet like easy in a sense, you should not be touching. Fire yourself from ever touching payroll ever again. Do not ever, ever do it ever again. Onboarding, the full onboarding, the full offboarding, IT, you name it, finance. If you're still managing accounts payable and accounts receivable, you're insane.

Welcome to Manage Chaos Podcast, where we give you the startup business rundown in less time than it takes for you to get to work. I'm Katrina Purcell, and today I am joined by Adam Spector, 4-time founder, angel investor in over 200 startups, including 14 unicorns, and the founder and CEO of Chore. A former product ops leader at Twitter, Symantec, and multiple venture-backed companies, Adam helps founders replace operational chaos with systems that scale. Adam, you and I were separated at birth in our desire for systems that scale.

Yes, we definitely were, Katrina. It's good to be here, by the way.

Thanks so much for coming on. So you've invested in over 200 startups, you've seen 14 unicorns. When you look under the hood during due diligence, what's that number one operational red flag that makes you concerned about the founder's ability to scale?

I mean, you know, it's actually so, so I invest really early. So actually for me, it's not really looking under the hood as much as it is understanding the founder themselves. And the founder themselves, what I'm looking at is, are they obsessed with this and are they willing to work harder than anyone else to achieve the outcomes that you expect? In other words, how good are they as individuals? Um, and look, anyone listening to this probably already thinks of themselves as pretty good at what they do. But the simple fact is most people are not, and most people are not as obsessed as like the really obsessed people are, like really, truly obsessed. You think about it, you dream about it, you can barely go to sleep because you're thinking about it. You just want to go solve it every day. Like that is obsession and most people don't have that.

I love that. So is that what you would say is kind of the operational habit that your unicorns shared in the early days?

For sure. It's a level of obsession. But, but the thing is, I guess from an operational standpoint, to be even more specific, What obsession leads to, and this is the important thing for operations, is focus. And focus is how the best companies succeed in not being distracted by what I call SOS or shiny object syndrome. It's very easy as a founder, you're hopefully taking in information from a million different places and getting that information in. And it's very easy to go, I want to run in this direction or this direction or this direction. And you have to not be that little puppy dog that like sees a new ball and runs after it. You have to say, you know what? No, like, I'm obsessed with solving this one problem, and until we solve this in a way that is so utterly unique, different, and delightful, I'm not gonna get distracted.

Yeah, I really love that. I think shiny object syndrome, a lot of founders have that because it, they follow the money. So, oh, this person wants to pay me if I do this thing, which has nothing to do with my core business, but they'll pay me. And people tend to then say, okay, I should follow that. How do you keep folks on the path, or does their singular obsession keep them on the path?

I think mostly the obsession keeps them on the path. There is a trade-off sometimes, and this is the really hard part. And truthfully, I even struggle with this sometimes with my company, Chore. When you hit product-market fit, then it just works and it's really easy to stay focused. The problem is like knowing if you've hit PMF and if you haven't hit PMF, that you almost should explore other options. So if you have a customer who says, hey, can we try this or go in this direction or do this? You might say yes. I mean, I'll give you some examples for our, for our company at Chore. We have, we run back office services for startups. So it's essentially HR, finance, compliance, and equity, all the key things to run your back office. There's a lot of add-ons to that. So we have companies who say, hey, like, can you help us with, like, we do all of HR. They're like, well, do you also help with like the recruiting process? And then there's some other key areas too, where it's like, okay, what other pieces would we add on? And so we kind of, we want to say yes to many of these, but it's also like, well, where at some point you expand and now you're just, you're you're running every admin task known to man, and then that, that you're never gonna be good at any of them really. You just become spread too thin.

Yeah, I completely agree. So, your life thesis really mirrors mine, which is sort of that execution is greater than strategy. A lot of founders tend to have that visionary hat, and to be fair, that's why my company exists, because they are so visionary, but they have no idea how to actually make that vision a reality. How do you go about convincing founders to sort of get outta the clouds and focus on boring execution?

Yeah, I mean, I, I just try to ask I'm like, what have you actually done today? Like, what have you literally done today or this week that you are proud of? If you look back on this week, so we do something called Friday Wins at Chor. Friday Wins, and we look like, what was the big thing you got completed this week? Like, what are you excited by to share with the team that you actually did? And frankly, a lot of times founders, and frankly, a lot of people on your team have trouble saying what that one big thing was. It just was a week of doing random things that just kept coming up. And it's like, you didn't actually achieve much if that's what happened. So like, what was that big thing? I accomplished X. This is my one big target. And if you have one of those every week, you'll have accomplished 52 big things in a year. And that actually starts to become a real something to be really proud of instead of just saying, I don't know, I lost my time in email and Slack messages.

That's always my favorite part of let's look at your calendar. So your calendar might mirror mine, which is very color-coded. Everything is blocked. There's, you know, and founders are like, my calendar, why would you wanna look at that? And it's like random meeting, random thing, but no, time blocking, no sense of organization.

So I was actually just gonna say, I like to do an audit of my calendar. I used to do it every quarter. I probably do it more once, like once a year now, but an audited calendar is a good thing to do. But time blocks, you mentioned that. So we actually require everyone on our team to have time blocks for when they're working on different types of work. And I used to have, I got rid of it. I can talk about why I wanna get it back, but I used to have a time block just for focus time on my own calendar where I could just say like, I'm gonna sit here and focus on Just instead of bouncing from meeting to meeting to meeting to meeting, which what ends up happening the more sort of quote unquote senior you get, I wanna have a focus time where I can clean out all my emails, all my messages, and then even dig into maybe building one or two things myself too.

I love that. But wait, why? Okay, why did you get rid of it?

I got rid of it because we, um, let go of our former salesperson and we wanted to fix— so my, myself and my sort of head of go-to-market decided to split sales to do some experiments ourselves cuz we wanted to really dig in on the sales front. And I was covering sort of the afternoons. On the sales front, he was covering the morning, and the afternoon is when I had my time block. So I needed to open that up for sales calls to come in, which worked, but it meant my afternoons now became 30-minute meeting after 30-minute meeting after 30-minute meeting.

Right. Back to back to back to back. Yeah. Because you're back in founder-led sales.

Yep. Um, and that is good when you're trying to experiment, but it also can be really tiring too.

Yeah. So the afternoon is when you're most focused. So all my focus time's in the morning. That's when I'm firing on all cylinders.

So I can be pretty focused in the afternoon. I feel like I'm actually pretty good really throughout the day, which is, I think, maybe rare, but I probably would prefer a focus block in the morning and just like boom, get things done. However, being on the West Coast is, and I've lived here for, I've lived in San Francisco for 16 years, I've had to be good at doing like my focus time in the afternoon, 'cause that's when there's just fewer, fewer meetings because a large percentage of my customers, my team as well, is sort of offline from, you know, by 4:00 PM Pacific time. Yeah. You know, it's already 7:00 PM East Coast, so like it's quiet, it just, it's quieter. So you just gotta, it's more time to focus on.

Yeah. And as a founder, you kind of have to learn to adapt to what those cycles are. For a long time, so I'm on the East Coast, but a long time I, I was servicing, uh, UK clients. So no morning focus time because they're already in the middle of their day and they're raring to go by then. And you kind of just have to hit the ground running.

Exactly right. And look, this is the other thing that as US-based founders, we're really privileged in is like, so I work with people all over the world. You know, for a lot of those people, they're working the night shift in many cases. And so the idea of me being able to say, well, I can go block my morning to focus is like to them a joke. They're like, your morning means what? I block my like 1 AM to 4 AM and I get to focus then? Like, no, like, I mean, it just doesn't work that way. So yeah, you gotta, we, we're lucky enough that I can say it's during sort of a normal quote unquote day and I can go to bed when the, when the sun goes down. Um, I feel privileged just in that.

Exactly. So you've famously called back office operations an undifferentiated tax on success.

Yeah.

Most of our listeners are in a really awkward phase of sort of too big. They're not doing it by themselves anymore, right? But they're not quite big enough to hire a full-time VP of finance or a full-time HR person. What is your advice for navigating that sort of sticky in-the-middle phase? And what is one task that they should just officially fire themselves from?

Let me do a macro answer to that and then I'll give you a specific task. Yeah. The macro answer is you should fire yourself from doing all, essentially all admin work. Anything that is repeatable, but yet like easy in a sense, you should not be touching. So to me, that is literally all things HR. So, so to be specific, fire yourself from ever touching payroll ever again. Do not log into your payroll system. Do not touch it. Do not play with it. Do not ever, ever do it ever again. But it goes for all things HR, onboarding, the full onboarding, the full offboarding, IT, you name it. Finance. If you're still managing accounts payable and accounts receivable, you're insane. Like compliance. If you're dealing with the letters the state's going to send you and, you know, you let someone go, they send you a letter. saying, hey, you owe us. This person says they claim unemployment. You need to fill out this form to tell us that it's true. And you're filling that out or calling the state because the state says you owe way more than you have. Like, what are you doing? Like, do you actually care about building a real startup or are you just there to like keep yourself busy and pretend you're doing something worthwhile for the world? Like, give me a break. Like, that is a joke. So like, fire yourself from all of that. Hand it all off. Delegate everything. The way to solve it— certainly I'm biased, but like— you actually now can delegate this work to fractional outsourced teams such as Chore, who does this work for you, like delegate it to experts. The analogy that I use is one that hopefully most people will understand. Probably everyone listening, listening to this has some sort of business that runs on the internet. My guess is most of those people don't have a server in their garage. That seems funny, right? But it's— that's how people used to do it, right? Yeah. So 20 years ago, you used to have a server in your garage, right? That's what you do because there wasn't AWS. And then AWS came out and said, you know what, we are going to be better We are going to focus solely on building the world's best servers. It's going to be in the cloud. It will always be on. We'll have all the security and we'll give you just the fraction that you need of a server instead of buying a whole server. We'll maintain it. It always stays, all the things that come with it. They charge a little bit of a premium for that, right? They charge a premium so you never have to think about it. It's just off your plate and you know, it just works. The same exact thing now exists for operations in the back office. And if you don't do that, you're insane. Why would you still think this is a core competency for your business? to run this stuff yourself. And I, I'll pause there, but like Katrina, we can certainly talk about like the pain of recruiting, hiring, managing people.

Yeah, all those things.

Like literally that is just overhead. No one, like no company wins today because they have more people. Like literally that's actually a negative, like negative signal for VCs. So like, why would you wanna hire anybody in the back office? Like CFO, head of HR, all the way down through payroll manager.

So what is the most chaotic moment that you've had in scaling Chore?

Oh man, I think I, I can say it sort of right now, but it changes all the time. The most chaotic moment moment in some ways. Like, well, so we, we sort of spun off from my previous company and became our own independent company. That was pretty chaotic. I think we did it really well and really cleanly, um, and we were able to get— become profitable pretty quickly, which is great, you know. But every stage is different, right? So that was— we were— when we started, we were a 7-person company off the gate when we sort of spun out. Money-losing 7-person company. Um, I think the next big one was— and this is sort of pretty traditional— you hit like 20 people or so, it gets chaotic. We're at about 45 people today, and it's It's not chaotic. It is chaotic, but not like the bigger thing is more trying to figure out how do you keep up to date with AI and how that's changing things, right? As I just mentioned, I don't want to be proud of the fact that we have a 45-person company. That's almost an irrelevant number in the grand scheme of saying what sort of good business have we built? So do we have 45 people, but we're doing hundreds of millions of dollars in revenue? Like, that would be great. So we're not doing hundreds of millions of revenue, but like, That's the real question. So it's chaotic because the question keeps coming, how do we move faster every single day with fewer people? So that is the chaotic piece. And that's a question the same way I ask, I don't want to hire more people. So how do I automate things? Or how do I delegate it to outsourced consultants whose job it is to be really good and efficient at what they do? That pace of that is picking up, right? Yeah. 5 years ago, we just say, I'm going to hire more people. I have enough work in Human resources, I need to hire an HR person. Well, today, like, no, you should— your first thing should be, can I delegate this to a third party or can I build it myself? And that's the chaotic piece that I feel right now, because we're— we think about that every single day.

Right. And I think that's actually what most founders are thinking about every day is AI, how it's going to change things, how they should be learning. What's a resource that you go to to get the latest news or feel like you're as up to date as possible on all the new stuff?

I mean, that's like an impossible question. Yeah. There's so much happening every single day that it's nearly impossible. Truly, though, I have a fantastic executive coach. He's also an advisor to Chore. His name's Ari Meisel. He's great, and he's really deep into AI stuff and building a lot of his own things. He previously built a virtual assistant company, um, and sort of automated all these key pieces. So he's just a badass resource for that stuff. Also internally, we've, we spun up late last year, essentially a product AI team. to focus solely on like what, how many things can we build with AI on like a weekly basis, like experiment, build, and then take the things that are good and productize them. And so we're constantly sharing ideas or doing new things and we're sharing that with the team. And then I, you know, like I just, I read a ton of stuff and there's just so much happening. It's, it's, it feels, I think the people who are deep in the AI space are feeling this and I certainly am even, and I'm not that deep, but I do live in San Francisco. So it's here. There's so much happening. It's, it's almost like drinking from a fire hose and that is exhausting.

Yeah. And I think it's also, how is it applicable to you, right? There's a lot of different things happening, a lot of new stuff, but it's not all maybe applicable, right? And, and how do you start to differentiate what that looks like? I think that's where people are gonna be successful or not.

Yeah. And look, the problem is like, to go back to the SOS point, you wanna try all the new things. You're like, oh, this new model's like way better. Well, I should be using the new model cuz it's way better. But it's like, oh God, I gotta change up my whole workflow for this. And like, yeah, at some point you just say it's just not worth it. Like, let's just hope the model that I'm using will keep updating itself and not stress it.

Yeah. Okay. So Adam, we have reached time unfortunately, which is very sad. But what is one thing, one key takeaway that you'd like the listeners to, to remember?

Say no to everything that's not directly related to your product. Delegate, delegate everything else.

That is a perfect way to end this episode of Manage Chaos Podcast. Thanks for tuning in. Please like, follow, and subscribe us anywhere that you get your podcasts, and we will see you on the next episode.

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