A couple months ago, I announced the acquisition of Fetchnotes, a startup I took from ENGR 490 at the University of Michigan through Techstars in Boston. Like any startup experience, there were a lot of ups and downs, and I’ve spent the past few months trying to digest what lessons I’ll take with me to my new gig at Occipital and beyond.
In the spirit of sharing knowledge for the next generation of masochists — er, entrepreneurs — I figured I’d share as many “generalizable” lessons as possible. Plus, now when people ask me “What did you learn?” I can just send them this URL.
On product and the quest for product-market-fit
- There is literally nothing more important than reaching and maximizing product-market-fit. Until you have it to some non-trivial degree, everything else is just a massively uphill battle. Hiring sucks because no one wants to work for a no-name company with no traction. Fundraising sucks because no one wants to invest in a company with no traction. Getting press sucks because no one wants to write about a company with no funding or traction. Not to mention you have zero inbound for any of these things. The more product-market-fit you achieve, the more these issues tend to resolve themselves (and make way for new and more complicated issues). In other words, figuring out how to maximize product-market-fit is the single highest-leverage activity you can spend your time on because it makes other tasks easier.
- You can find product-market-fit with the wrong group of customers. Our initial hypothesis was that the reason people don’t use productivity apps is because the existing tools are too complex and feature-rich for the mainstream crowd. We thought the “spectrum of productivity” looked like this:
And we were sort of right:
We did find product-market fit with this “underserved majority” in the middle, but there weren’t enough of them to build a big business around (one reason we were moving more toward collaboration as time went on). The productivity user spectrum was much more binary than we thought it would be — you tended to be either someone who cared a lot or not at all. And the true majority just doesn’t give a shit. (Side note: I think this is changing as time goes on, but seed-stage startups generally don’t have the runway to wait out social change!)
- Product-market-fit moves. When we launched in 2012, cross-platform sync was actually still kind of a big deal, and there were a non-insignificant number of people who used us because our sync was better than other products in the space. By 2014, this was the expectation. Constantly re-evaluate your market position, even after you’ve “achieved” product-market-fit.
- You should be brutally honest about how much product-market-fit you really have achieved, and be clear about the implications of what that means. This isn’t for the sake of self-awareness, but rather so that you can prioritize features/experiments. If you’re still far from product-market-fit, 10% improvements on your sign up flow are a total waste of time. This may sound ridiculous, but “not terrible” is a totally acceptable threshold for most of your non-critical metrics.
- Related to this, post-launch you should also know, “What are the top 1–3 hypotheses or product questions that still need to be proved?” Everyone on your team should know these things. This isn’t meant to describe nitty-gritty product management goals like “Will this feature increase D1 retention?” but existential questions like “Does our product allow us to grow virally?” or “Will people perceive our recommendations as ads or helpful?”
- Know where your product begins and ends. You should be deliberate about what use cases and groups of people your product is really good for, and which ones are better-served by other products. This is particularly hard for flexible products (like Fetchnotes) that can be used for so many things. We knew that if you just took a note every now and then about a book someone mentioned, you weren’t our target user, and in the same way if you were looking for a project manager or CRM, that was also not what our product was for. Try to map these use cases and tools out on a spectrum.
- Related to this, your users will have mental walls about the way they think about your product and what it is/isn’t for. Breaking these down and getting them to think about it in a different way is basically impossible without radical changes. More on that here.
- There are product problems and there are product trade-offs. Constantly, you’re forced to say, “Well, that creates this problem for this use case, but it makes A, B, and C use cases that are more common/important much easier.” Recognize that you will have to make trade-offs, or you’ll never get anything done.
- No one ever wished they spent less time talking to customers, but quite often people do regret listening to them. First, there’s the obvious challenge of discerning “what they need” from “what they say they want,” but I think good product leaders know how to do that. The larger challenge is to discern, all things equal, who to listen to vs. ignore. This is why knowing your product’s identity is so important.
- Regardless of what I just said, you’re probably not talking to your customers enough.
- Good products have a soul. During Techstars, one of our mentors told me something I never forgot: “Every time I use Fetchnotes I can tell that you guys put a bit of yourselves into the app.” Great products aren’t just a tool or way to do things. They’re imbued with the unique personalities and quirks of their creators right down to the copy, color schemes, animations, and communications.
- Surveys are a good tool for getting a basic understanding of behavior/perception quickly, but watching your metrics and having sit down conversations with users is the only way to get a true understanding of what’s going on. Too often, surveys are used as a lazy way of getting product feedback. Get on the phone and talk to people. Take them out to lunch if you can.
- Asking the right questions is half the battle (more on that here). There’s a fine line between customer validation (“is this the right product?”) and UX testing (“is this product easy to use?”), and most people assume they’re doing the former when they’re actually just doing the latter. Don’t fall into this trap.
- You can get a lot further than you think without writing code. Our first “MVP” was actually having people text me their notes (with the organizational tags in the text) to my personal phone number, and I would organize them in a Google Doc. Sometimes we’d have “server lags” and it would take awhile for your notes to show up — i.e., I was in class. There’s only so much you can learn without the real product, but this did teach me a lot about how people would use it, frequency, utility, etc.
- On a related note, you’re probably moving to high-fidelity mock-ups too fast when doing design. Doing so often causes you to commit too early to a design path, rather than exploring other ideas in sketches/wireframes.
- There’s an art to dogfooding your product — too little and you don’t have enough user empathy, and too much and you become a different kind of user. You shouldn’t use your product for use cases “because it’s possible.” We fucked up on this (used it too much) and had to readjust the lens through which we were looking at the product.
- When evaluating problems to solve, you need to be in the green box.
- Continuity is a critical but overlooked criteria for social product adoption. Products for groups of friends almost always flop because groups of friends change so frequently that it’s hard to build habits. Units like a families endure over the course of a lifetime. Given a long enough time horizon, I have a theory that almost all “groups of friends” products will either be co-opted by Facebook or never get people to move away from SMS/email in the first place.
- On the topic of habit formation, read everything ever written by Nir Eyal.
- In almost all cases pre-product-market-fit, your data will be murky about whether or not something is working and you’ll be relying on your gut. After some level of initial product-market-fit, you can start to rely more on metrics and set goals for whether or not something is working. But before that, you need to be comfortable shooting arrows through the fog. This is really hard for people that come from large companies/academia.
- Your product’s biggest competition is almost never another product. It’s probably some stupid hacky way that someone is solving the problem without technology, and their apathy toward trying something new. Stop thinking about competition as solely other entities and more about controlling mindshare.
- On the topic of competition, you’re probably way too worried about it. Chances are, they have no idea who you are, and even if they did know who you are, your existence wouldn’t change their business strategy very much. I actually had fairly open lines of communication with most of my “competitors,” and I got a lot more value than harm out of it in the form of lessons learned from failed experiments, metrics comps, and different perspectives. Moreover, having relationships at these companies opens the door for potential M&A/biz dev.
- You can often brute force non-trivial levels of traction, regardless (or even in spite of) what you’re building. That pig-headed determination is absolutely necessary to get things off the ground, but it can mislead you into thinking that you’ve achieved product-market-fit. Take time every few months to sit down and really question whether or not people are using your product because you persuaded them, or because there’s an underlying, enduring, and unique value proposition that extends beyond your persuasive abilities. Founder hustle doesn’t scale.
- The only thing more powerful than the laziness of the average consumer is their unwillingness to spend money. People will go through mind-blowing lengths to avoid paying just one dollar. We are a truly idiotic species when it comes to the way we think about money.
On managing cash
- Money is a constraint, but your scarcest resource is actually time. CEOs are usually way too cheap, especially first-timers that had been bootstrapping pre-funding. I know I was.
- Most of the expenses you actually spend time debating end up having zero impact on your overall runway. If you added up all of the expenses for non-critical items (extra monitors, snacks, team events, etc), it probably would have cost maybe a few weeks worth of runway over the course of a raise period. A happy team firing on all cylinders for 17 months will get 2–3x more done than a frugal, stressed out, and inefficient team will in 18. Stop being cheap and just say yes unless it’s ridiculous. (This obviously does not apply when you’re bootstrapping and teetering on the brink of death. In that case, be as frugal as possible.)
- Top-line revenue doesn’t practically make that much of a difference in the early stages of a funded company. Most funded companies depend on at least some non-insignificant level of scale to be profitable, so it’s normally not worth spending time trying to turn $500/month into $1,000/month if your burn rate is $50,000/month. You should absolutely spend time worrying about the drivers of revenue (like conversion rates, turning on different streams, etc.) — because that’s what tells you “at scale, this is roughly what we should expect” — but the top-line number isn’t going to make an impact on how you run your business until you have enough volume.
On fundraising and investors
- Every venture capitalist will tell you some variant of: “Our firm cares more about engagement than top-line user numbers.” At the same time, 90% of them have an internal threshold for number of downloads, MAUs, revenue, or something else before they take you seriously.
- Investors (pre and post funding) focus way too much on financial projections, timelines, roadmaps, and other forms of “filling in the gaps” because uncertainty is scary (more on that here). Good investors recognize that it’s at best a meaningless exercise pre-product-market-fit, and at worst totally counterproductive. Investors, please stop making founders spend time on something we both give so little legitimacy. You know these came from my ass. I know these came from my ass. Let’s please stop kidding ourselves.
- This is not to say that building models is a waste of time. They’re a good way to validate whether or not strategies are even remotely feasible, or flesh out assumptions. But let’s treat them like what they are — guesswork. There are only 2 goals in seed stage: 1) build a product the world needs and 2) get enough users or customers that you can raise more money or become profitable.
- Post-PMF, projections, timelines, etc. make more sense. This is another reason why it’s important to be conscious about where you are on the PMF spectrum — so you can communicate when these exercises are or aren’t important. Unfortunately, most investors run away from pre-PMF companies, so you’re incentivized to act like you’re post-PMF when you’re really not, and this is often a big factor in people committing to ideas too early.
- Make sure you are building relationships with the people who are ultimately writing you a check. With angel investors and VC funds (where the person you’re talking to has check-writing authority), you necessarily create a relationship with that person through the process of pitching, negotiating and keeping them in the loop post-raise. With angel groups and VC funds with more distributed authority, this doesn’t happen without you putting in extra legwork. You need to work at this, because when it comes time for you to ask for more money (which you definitely will) you want it to be as much about a belief in you as possible — NOT a financial decision.
- On this note, recognize that any investment in an early-stage company makes very little sense financially when you apply logic and math. You have no revenue, a half-working product, an incomplete (and often inexperienced) team, and a fuzzy vision. For someone to put tens of thousands (if not hundreds of thousands) of their hard-earned money into that is totally irrational when you really start to think about it. Good investors invest because they believe in you to defy the odds, and that what you’re building should exist in the world. That’s why it’s important to tell a story that connects with people, not just one that “makes sense.”
- Keeping investors updated on metrics and product development is relatively easy (even though most people suck at it). Keeping investors updated on strategy and shifts in thinking about the business is incredibly difficult. I still haven’t found a good way of doing this without sitting down in person.
- More $ is not always better. The more money you raise, the more achievably positive outcomes you take off the table for you and your team. Learn venture economics (I suggest reading Venture Deals).
- Counter to this, very few companies die because they raised too much money, whereas many companies die from raising too little. It’s a balance and you should err on the side of more.
- First meetings with an investor should be with the CEO only, but meetings with multiple people from a group almost always benefit from having your co-founder(s) in the room. In other words, try to keep the numbers equal on both sides (and shield your other cofounders from the distraction) until things get serious. Try to avoid having investors come by to “meet the team” until it looks like it’s a done deal — it tends to make people feel like zoo animals.
- People say there’s a lot of seed capital in the ecosystem, but it’s a bullshit statement because the requirements of a seed round now look like what used to be the requirements of a Series A: a fully-fleshed out product with solid metrics on a large pool of people. There isn’t nearly enough money in the ecosystem for “figure shit out mode”, whether that happens at the beginning or in the middle of a company lifecycle. I’m unsure whether or not this is healthy — yes, capital only gets invested in good companies (i.e., it’s a weeder system), but great companies may not ever come into existence. Manu Kumar just wrote an epic analysis of this.
- The most frustrating no you’ll ever receive is, “We really love you as an entrepreneur, but we just don’t think this is going to be the one. We hope you come back to us when you start your next company!” It’s like telling a parent, “We really like you as parents, but your baby is simply too ugly for our day care. Please make sure you think of us when you have a cuter baby!” You shouldn’t take this personally, but you will.
- Both investors and entrepreneurs care too much about valuation. For investors, standard liquidation preferences and anti-dilution provisions protect their capital. For entrepreneurs, they tend to see it as the number that defines their success up until that point, when in fact provisions around control (veto rights, board seats, etc.) make a tremendously larger impact on your day-to-day operations and the possibility of a personally positive outcome.
- Your existing investors are your most important source of follow-on capital. First, when they invest in their pro rata its a strong source of confidence to outsiders. Second, people are way more likely to say yes a second time if they said yes already. I was shocked by how many people I thought were “one and done” actually came through in my second round. So, don’t forget to keep these relationships warm — all it takes is grabbing lunch every few months.
- When you ask investors to reinvest, portray it as, “This is your pro rata — are you in?” Not, “Would you like to reinvest?” There is technically no such thing as “pro rata” on convertible notes, but I calculated it anyway and gave my early angels “pro rata rights” on my priced round. They were grateful for the opportunity, as founders apparently don’t always offer. And here I was thinking, “Are you kidding?! Of COURSE I’ll take more money!”
- There are only four ways an investor says yes: 1) you have massive traction, 2) you have social proof from other trusted investors/accelerators/mentors, 3) they have a personal passion for the problem/industry/product, 4) they have a personal relationship with the founder. If one of those doesn’t apply, you might get someone to take a really deep dive, but in the end there will be some stupid, idiosyncratic reason they say no at the last minute.
(So you have a gauge for relative frequency, out of the 12 entities that said yes to me, 5 were because of social proof like Techstars or another person they respected investing, 6 were because of personal relationships, and 1 was because of a deep personal passion for the problem/product.)
- “Hockey stick” companies will always get funded quickly, and these are the stories you hear about. However, most of us exist in the no man’s land of “good product, decent numbers” but short of a hockey stick. For us, fundraising is a fucking nightmare — not because it’s impossible, but because it’s just barely possible.
- You don’t need a PR firm to get press from tech media. I’ve been able to land articles in most of the major publications through mostly cold emails to reporters. All they want is a good story — they really don’t care where it comes from, and in fact they often discount stories from PR firms unless they have an existing relationship. If you have a good story for the right reporter at the right time, it will probably get covered. If you do not, then it will probably not get covered. A PR firm may help you better craft your story, but that should really be a core competency of your CEO. (Side note: This doesn’t mean PR firms don’t have value — just that they are not gatekeepers to coverage.)
- What’s going on behind the scenes at a company is a TOTALLY different scenario than what you see in the press. I have seen companies get glowing press when I know their company is in the shitter, and I’ve seen people win awards when I know they’ve already given up. Remember that when you get discouraged from all the funding and M&A announcements. Don’t get sucked into the hype.
- Related to this, you also have no idea what other companies are really thinking behind the scenes. I’ve been amazed at how many times I’ve passed judgment on someone else’s idea or strategy only to meet someone from the company and realize it was just an experiment, or they have something really novel up their sleeves, or, despite what you think, it’s actually working.
- You get one chance per year to shamelessly ask every single person you know for help spreading the word about something by sharing on Facebook/Twitter. Only one. Make it count.
- Weird shit gets attention. See this and this.
- Outside of the tech community, people don’t invite their friends to try out apps just because they like them. It’s not something normal people like doing, and if they do recommend your app to another person, it’ll be outside of your invite flow (verbal, via FB chat, etc). It happens, but don’t bank your strategy on it.
- People do send invites if there’s an explicit reason to use the product with another person. We had a lot of success prompting people to invite others around very targeted suggested social use cases:
- Overall, the only way to grow “virally” is to maximize the touch points between your users and non-users through the course of their normal and organic use of the product. For example, I want to share a note with you, but you’re not on the product yet, so I share it with your email or phone number.
- Optimize for the percentage of people sharing content (particularly outbound) through your service, not the percentage of people that convert on invites. You can have a 100% conversion rate on invites, but if people don’t share content no invites will be generated. In other words, optimize as high up the funnel as possible. Practically speaking, if a user is trying to share content with another user, don’t gate it just so that you can get the invited user to sign up. They won’t, and the inviting user will stop sharing content with non-users.
- “Growth hacking” is NOT a growth strategy. It’s a holistic framework for thinking about growth strategies. This term has been butchered to the point that it hardly means anything anymore. Calling growth hacking your growth strategy is like saying “agile” is your product strategy. Stop doing that.
- Understanding your user persona is the first step to marketing. If you don’t have a narrow person you’re building for, it’s hard to identify where to find them. At the same time, this is basically impossible to do well for horizontal consumer products.
- Doing things that don’t scale is totally fine…until you need to scale. We were really good at unscalable growth hacks (guest blogging, one-off partnerships, press, App Store features) but finding sustainable, cost-effective growth strategies is way more difficult. “Hacks” started to lose impact around 50,000 users.
- Growth doesn’t happen without retention. See this. Don’t focus on growth until you’re retaining users. Seriously. I know you want to. I know you think you’re ready, and I know all your investors are breathing down your neck about it. But if you have a leaky bucket, your efforts will all be for naught. This is why everything always come back to product.
- Read everything ever written by Andrew Chen. Or take his course. Or both. You should probably do both.
“Assume that everyone on earth is unreliable and full of shit until they prove otherwise. Except for me and your mother.” — Dad, some time in middle school
- This is the most important and consistently true piece of fatherly advice I ever received. By and large, people far oversell both their ability and willingness to help you, and you should never rely on anyone until they prove they deliver. Moreover, when it looks like you won’t be the hockey stick you thought you’d be, people have a way of disappearing. Except for your mom and dad.
- The people who defy this rule are special. Hire them, get them as investors, and don’t ever take them for granted. You will work with them again and again.
- Most advice is unreliable, because it’s often given by successful people who faced optimal scenarios (that’s why they’re sought out for advice, after all). 90% of the time you are not facing an optimal scenario — you’re in the in between, and you don’t have the same kind of leverage they did. Don’t blindly assume what worked for someone else will work for you.
- Respect the people you read more than the people you watch. I find people tend to overly aggrandize great orators — it’s easy to get so wrapped up in charismatic delivery that you don’t realize they didn’t really say anything that novel or substantive. Then again, I might just be biased as a better writer than speaker.
- The most important investment someone makes in you is when they join your team as an early employee. They’re investing a far more precious asset than money (which they are too, via sacrificed earnings) — they’re investing their time. They are committing literally years of their life to a vision that wasn’t even theirs, long before it has the validation to make that choice easy. They have to explain to their friends and family why they chose to join some rinky-dink little startup over companies they’ve heard of like Facebook and Google. The people that have the balls to do that are unbelievably special, and it is both your duty and your honor to ensure it’s a worthwhile adventure.
- Co-founder compatibility isn’t about having the same working styles/personalities — it’s about having complementary working styles/personalities. If you’re both conflict-avoiders, you’re going to have a bad time.
- On this note, never fool yourself into believing that you can change people. Yes, people change, and yes, you can and should have an impact on that, but betting on this is going to lead to issues. This is particularly true with things like work ethic — you can get someone to work harder for a short period, but over time they always revert back to their defaults. If you think someone consistently isn’t pulling their weight, it is very unlikely that you can get them to change this long-term.
- On this note, defaults are set within the first 1–3 months of employment. After this period, it’s extremely difficult to change work style, punctuality, etc. Make sure you set the pace in these first few months and over-communicate your expectations.
- There are quickly compounding consequences to pushing employees beyond their limits (i.e., working late or coming in on weekends). Sometimes it’s necessary for very short-term bursts, but more often than not you just think it is due to the pressure you are under. Leave this decision to your co-founder/CTO (or whoever is running engineering), who is both aware of the external pressures the company is facing but also more tightly in tune with the team’s energy. He or she will make a better decision than you will as CEO.
- Get to know your employees on a real, personal level. Know what makes them tick, what motivates them, and what drives them totally insane. Know what they do for fun, what their relationship is like with their family, and what’s going on with their significant other’s life. This is the shit that people bring into the office with them every single day, and I can cite countless examples of nipping issues in the bud (or not chasing the wrong issues) only because I knew people on a level that most managers find unnecessary.
- Compliments are an important part of being a manager. Early on, I tended to just assume people knew I valued their work and didn’t need reinforcement. It’s actually in the throes of the chaos and uncertainty of a startup that reassuring people of the impact they’re making is most important. Don’t overlook this.
- Start doing one-on-ones. Not because you don’t already have an open line of communication with your team, but because it gives everyone a specific, dedicated time to talk about anything that’s on their mind. It’s a lot easier to discuss something that’s bothering you in a one-on-one than it is to muster the courage to bring it up on your own. Plus, this is also an opportunity for you to relay strategy/priorities in a more personal way.
- Outside of tech, people will generally have zero concept of what your life is actually like. Common misconceptions:
- You’re rich
- You’re the “boss” and can do whatever you want
- You’re some sort of prodigy
- You know how to fix their iPhone
- You can get them a job.
Not to mention massive misconceptions about money, press, users, etc. Overall, people tend to massively overinflate you as way more successful and talented than you actually are.
On dropping out of school and becoming a “real company” and a “real adult”
- Looking back, overall, I’m very happy with my decision to leave school. Not because we had an exit or any result of the company itself, but because I accelerated my rate of learning far faster than my peers. I think that’s because of the startup experience itself, not dropping out, but if I waited a year to take that leap I know our momentum would have waned by the time I graduated. Overall, I think I am ~2–3 years ahead of where I would have been career-wise.
- Dropping out has a very real impact on the relationship with your friends and family. It puts you in a different life stage than most of your peers, and I’ve seen it really strain relationships. Worse, your family may not be supportive at all, and this can make your life a living hell. I’m fortunate that my family was exceptionally supportive, but I still feel guilty that I robbed my parents of seeing their only child graduate from college in The Big House (the University of Michigan’s football stadium). Not to mention robbing my grandfather of seeing his oldest grandchild graduate from his own alma mater — but my uncle graduated from UM, so I feel less bad.
- Dropping out of school had virtually no impact on my job prospects in the technology industry. Absolutely zero. If I was going into another industry, this would likely be less true.
- The first year (2012–2013) was the hardest — I had all this stress to deal with as we transitioned from student startup to “real company,” and on Facebook I saw nothing but photos of my friends partying away their senior year. Meanwhile, I knew practically zero people in Boston when I moved there.
- When you tell people you dropped out of school to do a tech startup, they jump to Zuckerberg/Jobs/Gates comparisons like clockwork — nearly every single person. They say it in one of two ways: “Oh! You must be like Mark Zuckerberg or Bill Gates! That’s so cool!” or, “Oh! Well, Mark Zuckerberg and Bill Gates both dropped out of school, and look how well they did!” The former is certainly annoying, but the latter is just plain condescending. It’s as if they think it’s something you need to be assured about.
- Overall, you get more attention than you deserve just for being a dropout —people still aren’t used to the concept. This is beneficial for PR (Exhibit A).
- Dropping out is absolutely not the right choice for most people. But it’s the right choice for enough people that it’s worth considering.
- When you leave school, you don’t suddenly become a real company by working more hours. You need to rethink how the fact that you’re full-time changes everything from the way you run your development process to the way you hire to the way you think about your overall goals as a company. It takes deliberate effort, and there will be growing pains. Frankly, this part fucking sucks.
- Related to the above, going full-time on a startup for the first time means you lose the ability to divert your attention to other priorities. When things aren’t going well, you don’t have a French exam to take your mind off things. The emotions (good and bad) are magnified.
- What was impressive while you were a student startup is, at best, the baseline when you enter the real world. You were a big fish in a tiny pond and the real world places a lot higher expectations on you once you can’t play the student card.
- The substance of college classes do absolutely nothing to prepare you to be an entrepreneur or even a key player in a startup. Zero. And I went to fucking business school. However, campus life— being surrounded by highly ambitious, smart people, and trying out many “versions” of yourself — was an important formative experience I’m glad I had for 3 years. That’s hard to replicate without enrolling in college (but it’s becoming increasingly possible).
On being a founder and CEO
- Non-founders will never understand the unique journey of a startup founder. This is why, over time, your close friends end up being 1 of 2 people: startup founders and friends from college/youth.
- You as a CEO face a fundamentally different journey than anyone else on the team, even your other founders:
1) You’re privy to way more external feedback, and one of your most important roles is filtering that input appropriately and absorbing the rest.
2) You’re the rock. You can’t talk about how much you hate a certain investor, or how you’re afraid the company is going to die, or how pissed you are at an employee for something. If you do, you’re going to stress your employees out even more than they already are and fuck up the culture. This is another reason why you mostly hang out with startup founders — you need to vent to someone who gets it. Even then, you’re worried about what will get back to the wrong people. Balancing being too poly-anna with being too real is one of the hardest things about being a CEO. You need to be able to absorb the stress to keep your team focused, but also filter just enough down to create a sense of urgency. Being the rock can really fucking suck.
3) Related to the above, you live in a world of uncertainty that is fundamentally unimaginable for most people. There have been at least 3 times in the history of our company where we were weeks away from not making payroll, and I don’t think we ever had more than a year’s worth of cash on hand. You know every single way your company is probably fucked (because you listen to people tell you why constantly), but “probably” seems like good enough odds to you. You live in a world of unanswered existential questions, but you have to tell a cohesive story that keeps everyone excited — including yourself. There comes a time in every CEO’s journey where you have to convince people of something that you’re not even sure of, but you know that if you don’t all hope is lost. Over the entire course of our company’s life, the only times I can legitimately say I was depressed were on days when I had to do that.
- As a founder, you need to be good enough to do anything, but you never really have time to specialize. This has a tremendous impact on your career, and it should not be taken lightly. I’m a really good generalist, and I know I can learn anything, but who is a company going to hire? Someone with 5 years of experience doing lots of things, some of which are what they’re looking for, or someone with 5 years of experience doing the 1 thing they really need someone for? Despite being very experienced, to many companies I’m unemployable.
- As a founder/CEO, you get to socialize with people way above your league (either deliberately or accidentally). Don’t be the guy that asks for coffee “just to connect”, but being a founder gives you more of a pretext for reaching out to people than you have as a role player. These are relationships that put your life and career on a different trajectory — don’t take them for granted.
- Be effortful about trying to open up this opportunity to your team — you can often enable them to meet their idols, but they don’t think to ask. I wish I did this more.
- Have a keen self-awareness of what you’re really good at and what you’re really bad at. Spend as much time as possible on the former, and hire people to do the latter.
- When you raise capital at such a young age, you get a totally warped perspective on money. When I was 18, $25,000 seemed like an impossibly large amount of money. By age 21, I was regularly talking to people about giving me millions of dollars. There have been at least 10 times over the past 3 years that I have looked at my Chase.com bank overview and seen enough money to purchase a private island in one bank account (the business account), but not enough money to buy lunch that day in the other (my personal one). It’s a weird feeling.
At the end of the day, your job is to bring talented people together, and empower them to do the best of work of their lives. I succeeded at this task more than I could have ever imagined.
But it was really hard not to buy that island.
On managing stress
- Know yourself and how you best manage stress. It took me years into Fetchnotes to discover my love of getting lost in audiobooks on long hikes, but I’ve been much less stressed out since.
- Relatedly, taking time off is as important for you as it is for other people on your team. There’s a religion to founders being workaholics, and while yes, it’s hard to do anything truly impactful working 40 hours per week, working all night, on weekends, and through holidays does way more harm than help over time.
- Also on this note, have ONE thing per week that is sacred. For me, that was going to Michigan football game watches on fall Saturdays, or during the offseason taking Saturday to hike/bike and listen to audiobooks. Make sure this is something away from both your house and your office, and if possible avoid email.
- Use an email app that lets you snooze emails (like Acompli or Mailbox), and end every day with an empty inbox. Even if it means snoozing dozens of messages.
- Try not to work from home, or if you do at least don’t work from bed. When you get in bed, close your email client so it doesn’t ping you with anything. When I have shit to do on weekends, I go to bars with wifi because I try to psychologically anchor my apartment as a place without stress. Additionally, it’s better to stay at the office late than go home “on time” and do more work there.
- Know your rhythm. If you’re not a morning person, sleep in and work later. If you’re not a night owl, get in early and leave in time to have a life after work. That said, basically zero people I know regularly start their day at noon and are actually productive. Personally, I would usually wake up around 8:30am, be in the office just before 10am, and stay until about 8pm. (But this would often stretch later during high-intensity periods.)
- Sleep more. Seriously! You’re probably not sleeping enough. I know I wasn’t.
Closing, unorganized thoughts
- Every era of entrepreneurship has a “zeitgeist,” or a predominant way of thinking that dominates a period of time. Growth hacking was the one I came of age during in 2011. Understand how that influences the way you look at the world and company-building, both good and bad.
- You don’t need to build your company in Silicon Valley, but you DO need to spend time building relationships out there. Don’t worry about not being ready (i.e., “I don’t have enough users for investors there to take me seriously”) — the fact that you even feel that way underscores why Silicon Valley is such a special place. Don’t ignore it just because you have pride in the place you’re currently building your company.
- Just like you can accrue technical debt, you can also accrue “entrepreneurial debt” — where you fuck up the culture, investors, or product strategy by taking shortcuts for immediate needs. Just like technical debt, sometimes entrepreneurial debt gets so large that your only option is starting from scratch (which means the company dies).
- The difference between luck and skill is extremely difficult to recognize. We hail results, often never stopping to question whether they’re the result of the power of the rocket ship or the talent of the person guiding it. I find this is is especially the case in Silicon Valley, where early employees at big companies are worshipped.
- Luck isn’t random. Work hard to maximize your Luck Surface Area.
- Starting up is the art of prioritization. EVERYTHING is important, but it’s a matter of deciding which important things you’re going to spend time on and which you’re going to ignore. At any given time there were at least a dozen “major” issues I was ignoring so I could focus on the “existentially-threatening” issues.
- Starting up is the art of solving chicken and egg problems — namely, you need money to make progress, and you need progress to attract or make money. I believe this acts as a giant weeder mechanism for entrepreneurs — the good ones figure out how to make something give, and the bad ones don’t get off the ground and waste other people’s money.
- Starting up is about stories — the story your product tells its customers about how you’ll improve their lives, the stories you tell investors about how you’ll make them money, and the stories you tell your employees about why your company is the best way they can spend a large chunk of their precious time on earth. This is why I’ve always valued coming from a journalism background.
- The most important story of them all — more important than any of the ones mentioned above — is the story the founders tell themselves about why their company needs to exist. This story very rarely changes or loses conviction. But when it begins to waver, there is very little that can be done to get it back.
- Be well-read, well-rounded, well-travelled, and interesting. Your job as CEO is inspiring others, and the more you know about people, places, and things the easier it is to make real, deep connections.
- On this note, read a lot, but read outside of your discipline. There a lot of mediocre business and business psychology books, but I find I get the most out of reading about things like anthropology and genetics. They help you understand why society is the way it is, not just why individuals say or do stupid things.
- Tip well, hold the door open, and be nice to service professionals. You should be doing this for the sake of being a good person, but people notice.
Have any questions? Drop me a line any time here if I can be helpful.