, writing that it contained “All the things I know about scaling and how to try to do it well.” As it turned out, this collection of lessons from her experiences building teams at Google, Facebook, and 

 would strike a chord in the startup world. Her mandate charging readers to 

 is still one of the Review’s most widely read articles — and it’s become a timeless, oft-cited metaphor for how to thrive inside of a rapidly scaling company.

The message seemed to hit a nerve because it gave voice to the emotional realities of startup life that often go undiscussed. “You go to cocktail parties and people ask you how it’s going, and you have to fake it. You say that everything is great even though it often feels like the world is falling apart. You think it’s just you that’s struggling,” says Graham. “It mattered to a lot of people, I think, to hear that feeling is actually completely normal.”

But in her view, recognizing the normalcy of these emotions is just the first step on a long journey. “We need to flip the switch from gritting your teeth and muscling through to acknowledging and managing your emotions,” she says. “And it can start small: 

What would happen if we all talked more openly, even just to our friends, about the emotional rollercoaster of work?

In the three years since the Legos article first came out, Graham has made a side project of researching and leading discussions on these very questions. She’s given numerous talks at scaling companies such as Stripe, Slack, 

 feels like inside rapidly growing companies. And she’s also added a few more personal data points to her own collection of scaling experiences, from a successful exit (when 

 for $750 million) to a stint on yet another rapidly growing team (the 

, where she served as VP of Operations while the team scaled from 30 to over 200).

Now, as a startup advisor (and future founder mulling over company ideas of her own), Graham is back to dive even deeper into tactics for handling the emotional rollercoaster of scaling with grace. She covers why the whirlwind of emotions we face at work are “normal, but not useful,” and shares the strategies that have helped her keep her head on straight. Graham also frames up the tools she’s relied on to defang especially challenging emotions and cultivate a mindset that enabled her to thrive amid the twists and turns. Let’s get started.

There’s a wellspring of intense emotions underneath the surface of every growing startup. For founders and early employees, company building life is intense and chaotic, but in Graham’s view, that’s not necessarily a negative signal in and of itself.

“You’re fighting to survive and for people to give a shit about your company. There’s no way that the stress of building something from scratch doesn’t affect your emotions. You’re cycling through anxiety, fear, euphoria, boredom and then back to fear again as the situation changes, and that’s completely normal,” she says. “But if you don’t 

 that’s normal and how everyone secretly feels, well then you can add feeling isolated and discombobulated to the list, too.”

When you’re at an early-stage startup, a significant percentage of your time is spent feeling like the whole thing might go off a cliff.

Out of all of her scaling experiences, Graham’s time at Quip felt the most intense. The difference? She joined Quip three months before launch when there were only nine people, as opposed to the 500 that were already on board at Facebook when she joined in 2008. “I was prepared for the emotions that come with 

, which I had become familiar with from all the scaling at Facebook, but I was deeply unprepared for how different and emotional the process of helping to start a company is,” she says. “At Quip, I was more personally invested — and when you’re more connected, the highs are higher but the lows seem lower."

Graham points to the particular emotional turbulence that followed Quip’s July 2013 launch as an example. “After the pop, things started to slow down, which is normal. But I wasn't sure how we were going to follow it up and I found myself kind of spiraling,” she says. Over lunch with a friend, however, Graham got the reality check she needed. 

“I opened up about how ambivalent, insecure and uncertain I was feeling. He just looked at me and said, ‘Welcome to startups.’ That was the moment that unlocked it for me; it’s what made me realize that what I was feeling was normal. I was like, ‘Oh, a lot of people at baby startups feel this way!’ And that realization sucked the power out of the emotions and made them less intense. How much healthier would everyone be if they realized that people at all the startups they admire also feel terrified half the time?” says Graham. “There’s so much power in admitting and sharing that, in recognizing that it doesn’t actually mean that the company is driving off a cliff.”

Take a breath and realize the rollercoaster — the highs and the lows — is normal.

WHY YOU NEED TO MAKE FRIENDS WITH THE MONSTER CHEWING ON YOUR LEG

To encapsulate how these emotions show up and how we can ride out the roller coaster’s twists and turns, Graham leans on another colorful metaphor: If learning to scale yourself and your job at a startup makes you feel like a kindergartener forced to share Legos, then 

all the emotions that come with navigating a fast-growing company are like a monster chewing on your leg

“I call mine Bob,” says Graham. “He’s a tiny little monster and he seems friendly — I imagine him as a kind of muppet — but the truth is that Bob’s sole job is to make you the worst version of yourself. He aims to make you feel like you don’t know what you’re doing, to ask who even gave you this job in the first place, to behave in ways you’ll regret.”

For Graham, Bob represents all of the emotions and insecurities that can get the best of you at work. “It could be territorialism, anxiety, fear, doubt, politics, envy, FOMO, you name it. He’s like a backpack you can’t take off, a weight that you carry around with you,” she says. “Sometimes Bob is just nibbling on your toes, but other times, he’s eating your whole leg. And those territorial people that are making everyone’s life miserable at work? Bob is probably driving their car.”

And it’s not a feeling that will dissipate with time or experience. “I started talking about Bob to help people realize that you won’t outgrow or shake off the feelings he represents," says Graham. "No matter how hard you try to ignore him or get rid of him, he’s always going to be with you. 

You need to make friends with the monster because like it or not, he’s on this journey with you. The skill you need to develop is 

At any given moment, ask yourself: Is your monster mostly well contained, chewing on your toes and smiling up at you? Or is he making his way up your whole leg? "Who is driving your car? 

It’s okay to have all of these feelings, but you can’t let your emotions sit in the driver's seat. You can’t let Bob win

Your number one job in a rapidly scaling startup is to not let the monster eat you alive.

But how do you keep Bob down at your toes with so much change, ambiguity, and chaos swirling around you? Here are three guiding principles that Graham has relied on over the last decade inside scaling companies:

Simply put, the first step is to recognize that all of the emotions that accompany scaling are normal — but also that they’re not useful.

“Whether it’s fear, stress, anxiety, territorialism, or insecurity, these emotions themselves aren’t wrong. To be clear, it would be impressive if you 

 feel them on a daily, weekly, or monthly basis inside a scaling company. Acknowledging that they’re normal, that everybody else is feeling them too, is helpful in making them feel less dramatic,” she says. 

But that recognition of those emotions and their normalcy is only half the battle. In Graham’s view, what matters more is how you 

“You’re in the middle of a tornado and there are all these feelings that go along with that. But none of those emotions provide cues or advice for 

 you should act. On any given day, feeling territorial doesn’t mean you should grab all the Legos back. Feeling insecure doesn’t mean that you’re not qualified for the job. Feeling anxious doesn’t mean that the walls are actually falling in. 

You shouldn’t try to avoid the emotions or ignore them, but you shouldn’t necessarily act on them either.

Just observe the emotions – ‘Today I’m feeling territorial’ – but wait to act on them until you know what’s real.

“I can say unequivocally that all of my biggest mistakes and things I regret the most are the times when I let Bob take the wheel,” says Graham. “Whether it was my ego taking over and saying ‘I need to make that presentation,’ or ‘I need to do XYZ to prove I'm important’ in a moment of insecurity and ambiguity, acting on that initial emotion never turned out well. But I’ve never regretted pressing pause to reflect.”

But how can you tell when the timing is right to take action? While the phrase “Why don’t you sleep on it?” rings true in some cases, in Graham’s view, this approach needs a little fine-tuning to better adjust to the startup context.

“A lot of these emotions last longer than a day. If you slept on it and you're still anxious or scared, that doesn't mean you should go talk to your boss or grab all the Legos back. It’s not a sign from the startup gods that you should send that angry email,” she says. “Instead, 

 any emotion or reaction you’re having to change around you, acknowledge it, shake Bob’s hand and say, ‘I get it, today I’m feeling territorial’ and then move on. Do that every day and 

if the emotion is still the same after a two-week period, 

 you should consider doing something about it

More often than not, this exercise allow these turbulent feelings to fade into the background. “You’ll be amazed at how many emotions pass in a two-week period. Something that feels dramatic and all-consuming in May will be gone by June, and you’ll be grateful that you didn’t act on it,” says Graham.

With startups, the only constant is change. Operating on a two week time horizon creates space for that change to take place, and more importantly, settle.

Graham readily acknowledges that some situations are not a “Bob problem” as she calls it, but rather a real one. “If you're still feeling almost exactly the same way after two weeks, that’s a sign that something deeper is going on. You should talk to someone — your manager, someone you trust, a coach, a mentor. While you don’t want to act on every impulse, you don’t want to go to the other extreme of never flagging what could be a serious problem for you or for the company,” she says.

3. Remember that everyone is battling a monster.

When it feels as though the monster may be winning, Graham’s advice is to go back to work and practice empathy, for yourself and others. “It doesn't matter what day of the week it is, it doesn't matter how well the business is doing — everyone feels like a fraud. It gets worse the more senior you get. It can also be worse for women and minorities,” she says.

The key is to recognize that everyone has their own version of Bob weighing them down. “Be kind to yourself by reiterating that, in all likelihood, you aren't an impostor and there isn't someone better than you for the job you're in,” she says. “And if your colleague is behaving weird or getting territorial, try to remember that it's because they're scared and have a monster eating their leg, not because they're an asshole.”

I have spent a significant chunk of time at every job feeling like I'm failing at everything. Ask every successful, competent person you know who has a the tiniest bit of self-awareness, and they’ll tell you that it has been the same for them.

MAKING SURE THE MONSTER DOESN’T WIN: THREE CHALLENGING EMOTIONS AND TACTICS FOR MANAGING THROUGH THEM

Recognizing the monster’s presence and making him your friend is key to surviving startups. But for Graham, it's not just about making it through. "If you deal with your emotions properly while scaling, you can work towards cultivating a mindset that allows you to 

, I've found there's a way to focus on the positive and on what you can learn," she says.

Here, Graham identifies three common (and uncomfortable) emotional hurdles that the monster can throw in your path and gets tactical on how to manage through them — and come out the other side even stronger.

Challenge #1: When things feel competitive and political

In rapidly scaling startups, fixation on titles and 

 can start to develop. “It’s one way that people try to control the chaos, but this tactic is straight out of Bob the monster's playbook,” says Graham. And she’s the first to admit that it’s all too easy to get pulled in. 

“I’ll own up to the fact that I got annoyed that I wasn’t a Director at Facebook. I felt like that recognition of my skills and contributions came too late,” she says. “It’s completely normal to feel this way, we’re only human. But you have to recognize that it’s because Bob is driving." 

And things can quickly get out of hand if you don’t beat him back. "If you let Bob win, your startup’s culture will devolve into a place where people waste time fighting for credit, control, or recognition for themselves rather than focusing on what’s right for the company," says Graham. "

If people give in to their fears, hold on to their Legos, fight other people for jobs, remain overly fixated on their title and who gets the credit, they usually don't scale with the company. You have to adjust your mindset if you want to succeed at scaling

In her experience, obsessing over credit and titles is a sideshow that’s not worth the distraction. “Everything is going to change in two weeks or three months anyway. Sure, you might win this battle today, but you’ve burned bridges and everyone knows you’re out for yourself, so what happens in two months when everything changes? No one wants to work with you. That’s why I recommend swimming in the opposite direction,” she says. “My golden rule is to focus on being useful. 

Give away the credit and just worry about making the right thing happen. Be the person that makes everyone else look good, and you’ll be amazed at the opportunities that come your way over time.”

Focus on being the most useful person in the room, and the rest will follow.

To put a point on it, Graham underlines her own experience. “Let’s be real that, looking back now, no one — including myself — gives a shit what my title was at Facebook," she says. "Ultimately, I collected a set of experiences that have been invaluable to me in everything I’ve done since, and that is far more important than any title could ever be. 

Concentrate on making the company as big and successful as it can be — that is ultimately what will make the biggest difference to your career.

Challenge #2: When fear and insecurity take over

When you step into a new role or join a startup in a different space, the intimidation factor immediately sets in. While impostor’s syndrome looms large in the background for almost all of us, it’s terrifying to admit out loud that you don’t know what’s going on. But in rapidly growing startups, Graham has come to value a willingness to learn, evolve, and sound like a moron more than established experience or deep expertise.

“Many believe that they have to be an expert in order to lead something, but I’ve found that no one can truly be an expert in the face of rapid scale — and pretending to be one leads to far worse outcomes,” she says. “All too often, people are so worried about sounding smart. So many important conversations aren’t had because people are so afraid of seeming dumb. The little insecure voice in your head telling you to stay quiet and nod along, that’s Bob taking control. Asking the right questions and learning to ‘figure it out together’ is actually the most important muscle to develop. ”

Graham has learned to put Bob back in his place with a trick she picked up from 

Sorry if this is a stupid question but…

’ line. When Chris was running HR, experts would come in to give us advice and he was unafraid to say, ‘I don’t know what that term means’ or ‘Can you explain that to me?’ It immediately caused incredibly smart, talented people to slow down and use smaller words to explain complex concepts,” she says. “I’ve used questions like this almost every day since. I used it to learn about mobile at Facebook, about SaaS at Quip, and I used it literally every day to educate myself at CZI about things as complex as biomedical research and criminal justice reform,” she says.

It's incredible what you can learn when you’re willing to suspend your ego, quiet that insecure voice, acknowledge that you’re a moron and ask people to teach you.

Aside from generating learning for yourself, this tactic is also a helpful tool for sparking conversations that otherwise wouldn’t be had. “If I sit in a room and I’m confused about what’s going on, I have two choices: I can assume that everyone else knows what’s going on, and just let it the conversation happen without me. Or, I can stop the conversation and ask a potentially stupid question. It can be terrifying, but try it a couple times — you’ll be shocked at how often the confusion wasn’t because you’re a moron, it was because 

 understood what was going on,” says Graham. 

Challenge #3: When you get caught up in envy and comparison

“People forget that building companies from scratch is really fucking hard, even if it’s going well,” says Graham. “In some ways, success is almost scarier. Your inner monologue is: Can you replicate it? Can you beat it? Can you sustain it? That’s why 

the worst thing you can do is rewrite history after success

. When I look back at my experiences, most of the time I'm like, ‘Jesus, that was really hard.’ I spend a lot of time inside scaling companies talking about all the things we did wrong at the places I’ve worked, all the ways in which things looked far better from the outside than they truly were on the inside.”

This is why Graham encourages others to leave the comparison game behind. “On the individual level, 

. But the truth is, their life is usually more uncertain and more insecure. Bob's with them every day. He may be chewing on their leg for different reasons, but he's there,” she says.

This pattern emerges on the company level as well. “You spend so much energy thinking, ‘If only we could grow like they're growing,’ or ‘If only we had made that hire instead.’ But the reality is that you have no idea what’s going on in that building and whether it’s even worth your envy,” says Graham.

“A couple years ago, when I was in a dark moment, my brother reminded me of that saying from third grade, ‘

.’ I now have it as a poster on my wall," she says. "For me, it’s a reminder that the only thing that matters is that I love what I do and am proud of what I build. Nothing else.”

In short, Graham says, for startups of every shape and size, it’s essential to realize that 

mess itself doesn’t mean something is wrong while success on it’s own doesn’t indicate that everything’s smooth sailing behind the scenes

Worrying about failure and comparing yourself to the success of others isn’t useful. No matter what the rate of growth or revenue looks like, the truth is that on the inside, it always feels like a mess.

THE FINAL TAKEAWAY: REMEMBER THAT YOU’RE LUCKY

To thrive in the midst of that startup scaling mess, when the walls are threatening to cave in, lean on Graham’s tactics. Think of the emotions weighing you down as a little monster chewing on your leg — but remember that you need to keep him in check. Don’t push your emotions away, but don’t act on them either. Instead, observe how you’re feeling for two weeks to give change a chance to settle. Avoid getting sucked into power struggles by giving away the credit and focusing on being useful. Fight fear and insecurity with a willingness to play the role of the moron, and deflate feelings of envy by remembering that every successful founder is weighed down by their own monster.

the opportunity to build and scale a startup is a privilege

. “Many small companies never get funded, and many of the ones who get funded never get to scale. Even when it’s exhausting and hard, it’s important to remember that if you’re getting to build and scale a company, you’re lucky,” says Graham.

“Take advantage of this opportunity. Give it everything you’ve got, but take care of yourself, and potentially even more importantly, be kind to yourself. Don't let Bob the monster get the best of you. And if you want to do something good for the world, maybe the next time you’re at a cocktail party and someone asks how it’s going at your company, talk about the chaos and what’s hard in addition to what’s fun and going well.”

Images by ZoneCreative/Getty Images and Drawkman/Getty Images.

Make Friends with monster.jpg

After telling us to 'Give Away your Legos,' Molly Graham is back to dig deeper into tactics for handling the emotional rollercoaster of scaling startups. Here, she shares the strategies she used at the Chan Zuckerberg Initiative, Quip and Facebook to keep her head on straight and defang three common challenging situations.

Make Friends With the Monster Chewing on Your Leg, and Other Tips for Surviving Startups

 and other high-flying startups are grateful that their coach, 

, didn’t skip out on a class called Military Science as an undergrad at UCLA. What he thought was a throwaway course delivered one of his most valuable insights:

“I started noticing patterns in startups — which I’ve validated with executives and VCs over the years — that how companies scale and break matches 

. So, the most efficient group in the military is a group of three, then a group of eight, and then three groups of eight, so 24,” says Halim. “Look across companies and you’ll see that around 24 people, someone speaks up to say, ‘We need a manager.’ If a startup makes it to 48 people, the next break is often in HR. And so on. As they scale, companies have more predictable breaking points.”

This truth is not just academic for Halim, but hard-won alongside founders, many of whom he’s coached since they were barely more than a founding team. 

’s Halim has helped a team of six grow into a now famous startup that’s 300+ employees strong and valued at more than $1.5 billion. He’s coached an executive team as its startup grew from under a 100 people with a $300 million valuation to a 1,000-person company valued at more than $5 billion.

In this exclusive interview, Halim pulls at the strings of this scaling-and-breaking phenomenon to articulate what he calls 

. He explains how companies and people grow at different rates — and what this tension means for how both will break while scaling. Halim shares how he’s seen this law apply to both executive teams and to founders, including the truths each must accept and the promises each must make. The VCs that work with Halim have played back to him how the founders that abide by this law can save themselves and their teams much heartache and stress — speedbumps that can cause any startup to decelerate.

“It’s easier to work with the CEO at board meetings.”

“The CEO’s personal life seems more stable.”

“I think working with a coach saved the CEO’s marriage.”

These are the types of comments that makes the day for any executive coach — and exactly what Halim heard last fall from a few venture capitalists. They had approached him, asking why the CEOs with whom he worked with from their portfolio were more resilient, level-headed and on a better growth trajectory than some of their other founders. Halim took the compliment, but couldn’t pinpoint a common thread, given his approach is not curriculum- or framework- based but to simply discuss whatever is top of mind for his clients.

It was only later, separated from his work over the end-of-year holidays, that it came to him:

The law of startup physics: humans grow linearly, companies grow exponentially.

It was a concept that he had started sharing with his founders — and an entry point into a serious conversation about startup scaling and breaking. “Human beings grow biologically and linearly. A year from now, you will be a year older — there's no growth hacking we can do to make that happen faster. Even if we were looking at the metrics of ‘you’—the age of your bones, your height, everything — you're not going to grow exponentially. You're going to grow linearly because all biological systems do that,” says Halim. “A company, which is a collection of biological systems called humans, can grow exponentially. Especially in tech, companies exist in a world in which you can be serving 100 customers one day, and a million a year later.”

What puzzled Halim is how something that's fundamentally biological can be put together and the result is exponential. “I realized that humans actually do something that's exponential: they tell stories. They share them, believe them and have feelings about them. This is not soft science. There’s a huge organizing principle around it, which in startupland we call ‘vision,’” says Halim. “What do 

 founders do in the abstract? They say they’re going to build this thing that doesn't exist. Then, if they tell the story well, they get others excited about it and involved. Then, they can organize groups of people to put, in some measures, an unreasonable amount of effort for something imaginary in order to produce this outcome.”

Take cryptocurrency and specifically Coinbase, one of Reboot's longtime clients. “This will be a time capsule of a comment in the future, but right now we’re in the middle of people telling stories about something that does not yet have a ton a real world application in creating a ton of value. Whether it’s imaginary or not, we're in the vision phase of crypto,” says Halim. “It is a story about a future in which everything's going to be different and better. So, you have some of our smartest people in our industry moving toward it. In 2013, about a month after I started working with Coinbase, Bitcoin went to $1,200. Then, by early the next year, it dropped to $800, then $400, then $200.”  

Coinbase had been scaling the team as the price of bitcoin dropped. “You can imagine at that peak in 2013 that you had a ton of people rushing into Bitcoin, and Coinbase was hiring. So, what happened when it dropped to 200? The truth of the matter is, is they didn't lose that many people, which, from what I’ve seen over the years, is shocking,” says Halim. “Many of them are running some of their major products today, the people that run GDAX and Coinbase wallet are people that were there in the room at that time. So, you have to pause and ask: what kept them there? If you spoke with the leadership team and employees at that time, they believed in an open financial system for the world, and that it was only a matter of time before the world changed. They were determined to be a part of that, even though, I’m sure, many owned Bitcoin and lost significant personal wealth. That, to me, was one of the first times where I really saw the power of vision to get people at that scale to work through adversity. And here we are a few years later, and many of the faces at Coinbase that I knew back then are still there.”

Aside from the power of story for startups, this confluence of linear versus exponential growth has 

two key truths that Halim surfaces for his clients

. The first has to do with the law of startup physics as applied to an executive team:

1. Your startup will outpace most of its executives if it starts to grow.

Whether it’s a technical team or a startup in its entirety, Halim has seen this over and over again. “I worked with a company as the engineering team went from 20 to 60 to 100 to 200 people. In a matter of months, the engineering manager that got them from 15 to 60 people started to flounder,” says Halim. “People talk about learning on the job, but the truth of it is that managing teams growing at that clip is not something that is natural unless you've done it before. So at 60, people started to feel like they weren't being led well. So at that moment in time, you have to do what's called turning the team.”

, though Halim brings in a twist from Daniel Coyle’s 

. “Fred Wilson talks about a founder who claims that on its way to scale, a company will turn its team over three times. That means that the initial team will depart, be replaced by another team, and then replaced by yet another team again,” says Halim. “The thing is that it’s not that these people aren’t growing. It’s that they are either not growing fast 

 or there’s a barrier — ego, company structure or something else — that stalls them 

 their company. Even incredibly talented people at fast-growing companies fall behind.”

Learning can accelerate, but, on the most fundamental level, you can’t bypass the repetition it takes for mastery, whether it's management or figure skating. “When you do something, your brain creates a connection among neurons that are involved. Whether it's swinging a tennis racket or a dance partner, each time you swing, that connection fires and through the process of what's called myelination, it creates a faster connection on the circuit,” says Halim. “The myelin sheath is the white part of the brain that covers these circuits, and the more myelinated something is, the faster it fires. That’s why, if I try and hit an MLB pitch, I can’t react fast enough to hit the ball, but if an MLB player does, they can connect with a ball coming at them at 107 miles an hour. That's because that for the MLB player, those circuits are so fast. That myelination of that wiring — a biological process — only happens with repetition over time.”

If a person can only develop linearly and a company can grow exponentially, what does that mean for the employee or executive? According to Halim, there are a few options once you find yourself in a situation:

. “Firing is just one option, but one that happens frequently, because many executives’ ego can’t stomach Option 2,” says Halim. “This should never be a surprise to the person. Ideally, there’ve been conversations along the way about how the growth of the company is outpacing the growth of the executive, as well as attempts to support the person along the way with mentors, advisors and coaches. The biggest barrier to success at this point is ego, which surfaces interpersonal and cultural issues that weren’t there before the exec started struggling. The combination of being in over their head and interpersonal friction often leaves firing the exec as the best option.”

. “The other option is to recruit and integrate someone who has done the job above the executive. This conversation is difficult, but navigable,” says Halim. “Say you’re talking to the engineering manager that’s underwater at 60 people. Try saying, ‘We want to continue to help you grow in your career. But, at this moment in time, your career growth has stopped, as you're drowning, making it difficult for you to help the company continue to grow. So we’re at a crossroads, where we need to decide: do we hire above you and get you a mentor that you need to grow, or can your ego not take that and we have to replace you?’ I would love to say most people are open to hiring above, but a lot of people can't do it well.”

Both of these options are painful on many fronts: for founders, their early executives and the rest of the team. It’s also very likely to happen if founders don’t have foresight to have a more proactive conversation about a 

 earlier. This is where Halim has helped many of his founders, urging them to make a promise with their senior leaders as soon as they onboard.

: “Let’s talk about your last day first. If you look at the latest employment data, it’s likely that you're going to leave or we're going to part ways somewhere between 18 months and three years. Now you may be an exception to this trend, but we know someday it’ll happen. So with the time we have, here’s my commitment to you: My pledge to you is that we will be committed to your growth. My pledge to the company and its investors is to its continued growth. I can only keep both promises if the two stay connected. There’ll be a point when they don’t, and when that day comes, I commit to having another conversation about what’s next, whether that’s here in another role or elsewhere.”

Doing this at the onset accomplishes a few goals:

 “Delivering this statement not only brings more thoughtfulness and predictability around an employee’s stint at a company, but builds an idea of growth into company culture from the outset,” says Halim. “The term I like to use is selfish altruism. Selfish altruism is this idea that I want you to come here — and I selfishly want you to find every opportunity you can to grow yourself, but the only way you're going to be able to use those opportunities is if they're aligned with growing the company.”

 “Different than setting expectations, having this conversation helps actively define where an executive might be most effective, and of highest value to a company at a certain stage of growth,” says Halim. “I once worked with one of the first engineers at what turned out to be a unicorn. He's been an incredible mentor to people who are trying to build engineering teams from zero to 50, but he’s never managed a team of 200, 300, or a 1000. But he knows his sweet spot — and now can easily plug in as an employee or consultant in any early-stage technical team.”

 “Don’t bring up the tough conversation when you’re about to have it. Set the tone early. State the promise — or even go further to say. If we start to grow exponentially, we’ll hit a point where I’ll likely need to turn the team. We may be faced with a conversation where you may be out of your league. We may need to carve out a different role for you. Or hire above you at some point. Or part ways.’” says Halim. “Laying out those options show you have a plan from the start — not only for the company but for the new executive. And you can always reference this first conversation, which is why you have it on day one.”

The alternative is not dramatic or grim, but rather a gradual slip toward slow growth. “What it looks like all over are startups keeping somebody in a role longer than they should be in it. If that executive is an early employee, the founder feels some amount of gratitude or obligation to take care of them. But instead of doing that, the founder lets the executive sit in a position where the role is expanding far faster than they can learn, so they fail. And the founder starts to not take care of the company because it's now slowed down because she doesn't want to have the conversation she needs to have,” says Halim. “That’s what an unkempt promise looks like. It's not being honest about what the promise actually is.”

The double-edged truth of the fast-scaling startup: If the company grows as it should, it will outgrow many of its people.

2. The founder is biological, too, but this law doesn’t apply.

The founder, it turns out, is the one exception to the law of startup physics. “The CEO often says, ‘Why does everyone else lose their job and I don’t? I’m biological.’ It’s a really important question,” says Halim. “The answer gets back to the one thing humans can do that is exponential: thought, which extended turns into story or vision. You can think of a toothpick. Then you can think of 1 million toothpicks. And then you can think of the forest from whence they came. You can make those leaps in an instant, but only those mental leaps.”

Applied to the founder, exponential thought is company vision. “One of my studies is in ontological coaching, so I’m particular with words. When someone says, ‘I have a vision,” you never say, ‘Point to it.’ You say, ‘Tell me about it.’ And that’s because it’s a hallucination. A founder imagined something: a vision of how she wants the world to be. She articulates it to a co-founder, and he joins. Then to an investor, and she writes a check. And then to recruits, and they join the team,” says Halim. “The thinking of the company is limited to all the thinking in the company. Most executives in a company are thinking about OKRs — and the extent of their creativity is mostly around how to better execute what needs to get done on the roadmap. This is essentially biological, linear iteration. But that creates an average company. So you need someone in the company who’ll think bigger than the company itself, about its role in the industry and world. Take Jeff Bezos. No hired executive could’ve gone from selling books to server space to rocket ships. Only founders make those kinds of mental leaps. And that is why they can keep up with a company that is scaling exponentially. ”

The reason why a founder keeps her job is not just because of vision but because of declarative authority. “There's another unique aspect of being the founder of a company. It’s the only position in which you can hire people more senior than you that report to you. If I lead marketing, I can't hire somebody with 10 years more experience to report to me, but if I'm the founder, I can hire people with 10 years more experience than me in marketing and have them report to me,” says Halim. “They're reporting to me, again, because of this feature of leadership. They believe in this vision that I've painted, that they're signing up for and want to follow. But also because as a founder I can say, ‘We’re going here’ and it will happen, not the other way around.”

Founders are unique in this capacity for vision, as it’s not the same with hired CEOs. “A hired executive is put in place by the board, and once you’re hired by the board, you report to the board. And the board does not have exponential thinking,” says Halim. “Elon Musk is a great example of how a visionary founder part-time at Tesla and SpaceX is better than a full-time hired CEO. It’s not that there aren’t phenomenal CEOs who could take the role, or that aren’t talented. But a part-time Elon is better than a hired CEO.”

So what enables founders to tap into their full capacity to build companies that grow exponentially. “It’s intentionality around basics and extracurriculars. In other words: ‘Are you eating? Are you sleeping? Do you have a regular date night, or are you having a social life?’” says Halim. “It all has to do with peak positive emotions. I surveyed the leaders and they said, ‘I have peak emotions but most of them are not positive inside my company. There's stress and anxiety around where we are and where we could be.’ Peak positive emotions come from the ‘outside world,’ from connecting with other humans, a good night's sleep, from taking time away like changing your environment, and taking a vacation.”

: “This is a promise to my co-founders and myself. I will ‘get out of the building.’ I will take founder vacations. I will keep a date night with a spouse or loved one. If I don’t have one, I will hire an EA. This is all to help refill my mental and emotional reservoir, so I can perform in ways that I couldn't on day 10 of 14-hour days. I need to experience the full range of peak emotions to get to peak performance.”

Here is why this promise is particularly important:

 “This promise is not only important for the performance of the organization and the health of the founder, but for the performance and health of the team. Startups say we have unlimited paid time off, and then the founders don't take a day off. In this case, ask people if they’ve taken PTO, and don’t be surprised if they say no,” says Halim. “Especially at the start, people always model their behavior after the founders. Some founders, like Bart Lorang of FullContact, have taken this seriously and have something called ‘

.’ On top of salary, they will literally pay you to get out of the building. It’s that important to disconnect to recharge, but reinject better work into the company.”

 “Everything we do is meant to sprint then rest. There's also a book,

 that finds that immediately after exercising, your I.Q. goes up a couple of points,’ says Halim. ”The reason is, if you think about when we sprinted back in the caveperson days, it was either to not be eaten or to eat. So it was really important to rest and consolidate what you just learned after a sprint. Biologically, we are sprinting beings, not marathon beings. It is really unhealthy to eat consistently over time and always be nibbling on food. It turns out that it is quite healthy to stop eating for some amount of time to allow the body to go into what they call repair mode. Your cells have two different modes: growth and repair. It doesn't go into repair mode if it has an unlimited supply of growth and fuel.”

•Stokes creativity and problem-solving.

 “How many great ideas does someone have when they are working hard against a deadline and on their 14th hour of work? None. If you’re taking a breath — on a weekend away or with friends or at the gym — creativity happens,” says Halim. “Solving a problem, as Einstein says, does not happen by using the same thinking as that which created it. You can’t get super creative inside what is a company that is solving an already defined problem. You’re in a machine that’s built to solve a current problem set. Remove yourself to get new thinking.”

To drive the point home, Halim gives an example from his coaching career. “I was working with a set of founders early on at a company as they started growing exponentially and neither had taken a vacation in a long time. So I said, ‘You guys need to take a vacation in the next month’ and they didn't do it. So, I turned to their EA and I said, ‘Book them tickets. I don't care if it's a founder honeymoon, they have to leave the building.’ Since I had been there early and I had a certain amount of trust in the organization, he booked it,” says Halim. “Then, they were sending me pictures from Hawaii and the joke was, ‘Hey, we're on our founder honeymoon.’ They did it every year after that. That practice became a critical lever in their cofounder relationship, which in turn was instrumental to the health of the company.”

Halim issues one caveat around this part of the law of startup physics. “So, there's a world in which you're a small startup pre-product market fit, and there's a world in which you're after-product market fit. What I’m referring to is a post product-market fit scenario, when it’s feasible and critical to get out of the building,” says Halim. “At that stage, pace is critical and there needs to be a break. When you're on a longer kind of marathon path to scale post product/market fit, you have to build the brakes. It's like the Indy 500, the pit stops have to come at a regular clip.”

At the end of the day, the law of startup physics has everyone leaving the building — whether that’s the executives whom the startup outpaces or the founders who need to disconnect to recharge, reinvest and reintegrate new inputs into their vision. All of this happens because humans grow biologically and linearly, and startups are geared to grow exponentially. However, it doesn’t mean that this tension leads to fissures. With every early employee and executive, have a conversation about their last day on their first day. Make an explicit pact around their growth, the company’s growth, how they must connect, and how one day they won’t. Outline the options you’ll explore at that point. If you’re a founder, recognize why you’re the key to exponential growth at your company, and why that makes your tenure different than everyone else’s stint. You must also get out of the building, both to get inputs to extend the vision of the company and to set an example for your team. Schedule date nights and vacations — and stick to them as fiercely as a launch date. Your company — and people — depend on it.

“The law of startup physics need not be brutal, but it does govern how fast-growing startups scale. As an executive coach, I’ve seen it happen dozens of times. Those that orient their people around an explicit tour of duty and are forthcoming about what will happen when the company starts scaling, not only weatherproof their team, but supercharge them,” says Halim. “What’s left to do after that is taking care of the one lever to trigger exponential growth: the founders. The obvious, but often neglected solution is to get out of the building. We do it to meet customers or meet partners, but not enough for the founders’ sake in and of itself. They are the ones that stand on the edge of where their company is now, looking out at where the company could be. We need to encourage them to venture beyond the company’s periphery, not just gaze at it from a distance. If we do, they’ll come back with more than with which they left.”

Khalid-Halim_047RT (1).jpg

Reboot.io founder and professional coach Khalid Halim has guided the leadership at Coinbase, Lyft and Checkr through some of the steepest parts of their growth curve. Here, he shares the two promises every founder must make before hypergrowth. 

Hypergrowth and The Law of Startup Physics  

It’s week six in your new job at a bootstrapped startup, and the founder asks you: “Create a prototype of our software to share with investors. We don’t have a company name yet. And I need it in two days.” If this sounds familiar, chances are you’ve been an early employee at a startup. If this is your precise scenario, you’re 

When La first started with Clover Health, it was just the founders, head of product and a data scientist. She was its first designer and the company hadn’t raised any money. Now she leads an eight-person design team, Clover is 500+ people-strong and the startup has raised over $425M. Though La was a seasoned design leader (Yammer, Microsoft) before Clover Health, it was her first time as a very early employee forged in the crucible of a fast-scaling company.

In this exclusive interview, La reduces nearly every motion of an early employee to flexing one of two muscles: ruthless prioritization and high-return troubleshooting. For the former, she outlines a sequence of time management milestones to expect as an early employee in year one. For the latter, La asserts that every challenge must produce double the return in takeaways — and gives examples of that principle in action.

, there are many tools that can help generate greater efficiency. Then there are philosophies from productivity aces like Getting Things Done’s 

. All these resources can be valuable for the overworked, under-resourced early employee, but according to La, time management operates as a unique frequency for a startup’s first employees.

“At the start, it was fun taking the leap and deciding to get involved as an early employee. I was back together with people I had worked well with before,” says La. “But then it got daunting very quickly. The magnitude of the task ahead hit at once: my hybrid doer/leader role for a functional area, my learning curve in the health insurance space, and all the opportunities that Clover could go after in the market. Suddenly, spinning up felt more dizzying than galvanizing.”

Early employees: when it comes to time management, stack your priorities in two-week themes. That way you can balance actionability and flexibility.

With the support of Clover’s founders, La hit her stride when she zoomed out not only on her goals for Design at Clover, but also for herself as an early employee. “When joining a later-stage company, your role and career path are more defined,” says La. “On the other hand, for a first employee in an area like engineering or design, you must, of course, focus on shipping your part of the product. But there are also responsibilities that aren’t immediately apparent, like being the leader of a team — even if it’s just you at the moment. How you do the work — especially alongside other functional heads — sets the standard for how your team will integrate and run. Self development as a leader 

 at the company is also a responsibility. When the ladder rung above you is the founder, your goal is less to replace that person and more to come into your own. This requires original thought in defining the kind of leader you want to be and career that you want to create.”

When La speaks about how she discovered and chipped away at those responsibilities, she suggests a timeline more than tips.

 Here’s a sequence of inflection points that served La and can help you, as an early employee, gut-check your development approach to product, team and career:

Map two-week themes for the first six months.

 Context-switching is a killer for everyone — especially for early employees who have to wear multiple hats. You have to be versatile, but focused. “Early employees, like founders, must constantly operate at a balance of breadth and depth. I found the best unit of time to both efficiently execute and accrue a sufficient level of expertise on any key task was about two weeks,” says La. “For example, when vetting design agencies, all my planning, research, meetings, evaluation and decisions happened in a two-week span. Prioritizing biweekly themes creates enough momentum to create real value in a particular area of the business, but not so much as to cause a terrible setback if the intended results aren’t achieved.”

La stacked priorities based on the constraints facing the business at the outset. “The nice thing about being there at the start is that your priorities are very clear, because the constraints are numerous and looming. The most pressing must be addressed or the others won’t matter because you’ll be out of business,” says La. “For example, we’re driven by 

 [Centers for Medicare & Medicaid Services] deadlines. We had to be ready for open enrollment, which is October through December, and we had to have a brand and website. That needed to be in place before we could even think about hiring user researchers or developing a design system. Two-week themes are flexible enough that I could swap them modularly as business needs changed, if needed — and compact enough that I was too busy to waste time thinking of opportunity cost once I decided to embark on one. Focus and flexibility made this approach work for my first six months.”

Standardize how you triage your time by six months

. As Clover grew, La adopted a practice that her mentor, Airbnb’s Head of Design 

 as part of First Round’s mentorship program), calls “

“It’s a practical way to triage my time. ‘Eyes on’ is work that I don’t need to do, but need to be informed about, such as designers’ progress on projects or design requests from the org. ‘Hands on’ are actions that I need to work on independently. That could be meeting with candidates or developing the design team’s OKRs, for example,” says La. “‘Horizon’ is a category of themes and developments that are a month to six months out. It’s about to get on our team’s radar, but not yet on mine. Right now, that’s our design system, for example. This practice helps me get through to-dos and delegate. I do it on my own at the beginning of every week but at Airbnb Design’s scale, Alex does this exercise daily with a member of his staff. He emphasized to me that constant prioritization — the act of choosing to work on the right thing at the right time, over and over again — is 

 that will make or break a business. I’m now a lot more diligent about what I spend my time on, and the cost and ROI of those choices.”

Splitting one’s time into these buckets creates processes — new ways that information flows through an organization. While this creates predictability, it can also fill up one’s calendar. “As the number of stakeholders increase, there’s a tendency to build in more process. So another great tip that Alex [Schleifer] gave me is: ‘

Don’t add process unless it removes a meeting

,” says La. “That rule of thumb keeps you honest. When we started weekly Design Reviews, our goal was to give technology leadership visibility at key project milestones, and to push faster decision-making while shipping high quality solutions. Adding Design Review into our design process eliminated 5+ individual context-sharing and sign-off meetings.”

Pivot from product design to org design at month 9 to 12.

 Clover Health grew incredibly fast — in about two and half years its headcount went from five to 500. Given that, La began shifting her focus from design work to growing a design team within nine months of joining. Not only was she creating what the product was to become, but also 

“At about nine months, most my time was spent on recruiting and hiring, which was a shift out of my comfort zone. As an introvert, I noticed a change when the day held more coffee chats than independent work. When I wasn’t meeting people, I was drafting job descriptions, not just designing the product,” says La. “

This isn’t atypical for any individual contributor who becomes a manager

. However, as an early employee, a smooth transition at this moment is critical because it has a lasting effect on what the team will become — and often requires a founder’s attention. Kris [Gale, Clover Health’s co-founder] helped me realize that I was doing organizational design. I had to grow and structure a team that could get it all done.”

The key output in this time period is called 

. “When a company grows that quickly after you’ve joined, you naturally get institutional knowledge that’s layers deep. Of course, this know-how shouldn’t be organized chronologically, but by utility. Luckily, an early employee has the built-in perspective to arrange this knowledge — and I’d argue the need, not just the ability,” says La. “It was a release to get it all down and scale what I’d learned to the rest of the team. This was, and continues to be, crucial for building out our team, onboarding new design hires, the design review process and more. Growing quickly, I didn’t want the team to constantly reinvent the wheel.”

Scaling herself by documenting her design know-how gave her the bandwidth to help the company hire in a more intentional way. “When you have 15 people starting every week for 3 months you have to be extremely thoughtful about the hiring infrastructure you have in place. Communication gets exponentially complex and difficult as you grow, so we had to be conscious of who we were hiring and why,” says La. “It took months of discussing and interviewing candidates, articulating our mission and thinking about how we wanted to structure the team. At the beginning I didn’t know how to pitch health insurance in a compelling way, and we didn’t have a product to show. What we did have is an awesome mission. I internalized our mission and the potential impact for design in the industry. In expressing it, I realized just how much I believed in what we were trying to accomplish. After that it was easy to decipher which design candidates had similar beliefs and interests.”

The demands of a startup are dizzying. To anchor yourself, you must schedule time to write things down.

Any professional needs to learn how to problem-solve — but early employees have to harvest more from each challenge faced. In fact, according to La, 

as an early employee, you must mine at least two actionable takeaways for every challenge faced.

 If you aren’t hitting at least that level of learning, you aren’t 1) tackling big enough challenges for the business or 2) reflecting on and extracting enough from each task. Here are a few examples to illustrate some of La’s high-yield rate of learning as an early employee at Clover Health.

SOLVING FOR ISOLATION, LEVELING UP RECRUITING AND PROFESSIONAL NETWORK

It’s no surprise that early employees are drinking from a fire hose — and often alone. The isolation can be palpable with few or no other colleagues tackling the same swath of challenges. La found camaraderie externally early on to counter her independence — and isolation — as Clover’s first designer. “When you’re a first employee, you need peers. So one of my best moves was finding and reviving a dormant meetup. When I discovered it, there were about 80 members, they were looking for a new organizer, and there were no events scheduled. I took it over, and now the 

“It was great on the branding side for both Clover and myself. My team was still forming and I hadn’t worked in healthcare before, so developing a supportive design community was helpful,” says La. “It assisted in ways that I didn’t initially expect, and came to appreciate later on: creation of a community. It's great for professional development and finding connections in our work since not many designers have a healthcare background, and healthcare startups don't have huge design teams.”

Beyond the meetup, La sought additional resources to get the camaraderie and know-how she needed to do her job — and Clover’s co-founders stepped in. “I needed help and wanted to talk to other designers. I also didn’t know much about healthcare. 

 had healthcare experience and connected me to people at other healthcare startups, like 

 [Gale] introduced me to designers and tech leaders in San Francisco,” says La. “They didn’t do more than just set up calls. Their style is not to tell me how to get the answers but to give me access to smart people for 30-minute calls at a time. I drove a lot of these conversations because I knew what things I was weak in and what I wanted to know.”

 was how it redistributed the founders’ rolodex throughout the organization. Creating more highly-networked nodes at a company can groom leaders faster at startups at their earliest stages. “Kris [Gale] introduced me to 

If you're joining an early-stage startup:

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