Since starting Onlook back in January, I’ve met quite a few people who are toying with the idea of entrepreneurship as their next career move, and I felt like sharing some of the (hard) truths that I’ve experienced while working on my own startup.

This is by no means an effort to discourage people from pursuing entrepreneurship, but a list I would have appreciated while I was in the phase of thinking about starting a startup. I felt many of these truths while I was working on Wanderlift, my first serious venture, but as I’ve matured and seen more of how the world operates, I can now feel confident that these are reality.

Obligatory disclaimer – All of these points are from the lens of building a venture-backed startup. There are plenty of other forms of entrepreneurship (like building your own embedded ops company – shoutout to Hup), but even so, there may be some relevant overlap for any kind of side-hustle.

16 truths of entrepreneurship

No. 1

People do not want to associate with companies that are not either a) cool or b) winning – You must be perceived as doing well. In harsher words, people don’t want to associate with losers, so don’t come off as one.

• One way you can prevent being perceived as a loser is by avoiding what I call “JV” a.k.a “Junior Varsity” behavior. It’s totally ok to make mistakes but try your best to quickly correct them. Make the mistake once, and try your best to never make it again.

• Try to excel at your professional behavior. People tend to be impressed when you have your life together and are tight with your process of doing anything. This is like the Broken-windows theory of your professional life – presenting well in one aspect of your life helps people assume that other parts of your life are going well too.

No.2

You cannot “will” something into existence – it must be earned…

• There is a lot of “playing-house” in startup land that so many of us are guilty of. Paul Graham wrote about this concept, but it boils down to “don’t mistake motion for progress”. So many people think the first thing you need to do with a project is get all of this other logistical BS setup before you can launch or do anything.
• I continuously come back to YC’s advice that the only two things you should prioritize are 1) talking to users and 2) building product. Everything else – and occasionally, even building product – is “playing house.”
• Doing anything is better than thinking of doing something, so go forth and earn what you think should exist.

No. 3

…and you don’t know what you can earn unless you try.

• You’ll overthink when the perfect time is to launch. You’ll tell yourself that just one more feature will be the winner for your company. The truth is, your ego is getting in the way of you learning a big big lesson by putting an idea out into the world.
• You should try to throw your business into the fire as much as you can. Especially because people will resonate with your message and mission more so than your actual product for much of the early days. It’s why I’ve come to realize that the title and logline (one-liner) of your startup (something I picked up from Save the Cat) are so critical – it’s what gets people fired up. This is a great article on writing loglines for scripts, but this amazing writeup on category design is a great reference for thinking about the logline of businesses.

No. 4

Entrepreneurship is purely rejection. You have to be prepared to be rejected constantly. Constantly. Again. And Again. And one more time. And Again.

• You will be rejected by investors, by potential employees, by customers who signed up and said they’d be interested in your product, by everyone.
• Most of entrepreneurship is just following up with people to actually get a rejection. At least a rejection is some peace of mind that they’re not interested, but sometimes you may just have a moment of opportunity and surprise where someone extends themselves to help you, or says “yes”.
• Nike recently put out an ad that captures the mentality: Winning isn’t for everyone.

It’s totally true with entrepreneurship. Have I (me, Daniel) won? Hell no! But I have to operate with this mentality because it’s the only way things will be achieved. See Point 2.

No. 5

Because you’re always pitching, you must be optimistic (Point 1).

• People invest their time, reputation, and resources in you for the possibility of your success, and it’s up to you to convince them. People don’t invest in neutrality, and they definitely don’t invest in pessimism.
• Your only role is to be the most optimistic about your idea because you’re the only one who is relentlessly optimistic about your vision and your idea.
• This comes with the caveat that you should not pitch to customers the first time you meet them. You should be “discovering” their problems and opinions, but for everyone else who isn’t a customer, you should be optimistic.

No. 6

The types of people that build companies are the ones that build companies (Points 2, 3).

• The people who build companies don’t talk about building a company someday, they don’t fantasize about the lore of a company, they don’t go to every startup event in their city. They actually do the thing and make something.
• This is totally and entirely obvious advice, but you will never have a grip on what actually works if you don’t try it yourself.
• How do you make something? You just do something. Right now. Get that Twitter handle. Write your first LinkedIn post. Doing anything is how you do the thing. You’ll need an audience for whatever you have, so start building it right now.

No. 7

If you run into a roadblock, it’s likely because you’re afraid to “Just…”. Just do X. Just do Y. Just email Z. I have to remind myself this all the time.

If you are serious about building a company, you should get on YC Cofounder matching immediately. It will take you months to find someone who is compatible, and you need to let the world know that you want to be someone that builds companies.

• All of the people I’ve met who are shy about getting on YC Cofounder matching are not serious enough about building a company. It is the easiest thing you can do to start meeting other people who have self-selected to be an entrepreneur.
• I’ll emphasize again, that even if you have a cofounder in-mind, YC Cofounder matching is a great pipeline for potential talent, so you must get on the platform. It is JV to not even try to get in front of other smart people.
• People’s willingness to take this very very low and approachable step is the biggest indicator of whether they’re playing house with the idea of startups.

No. 8

Losing touch with who you’re solving a problem for is very very easy. It is more important to know your customer than building something.

• You really should try your best to be in continuous contact with your customer, even if you think you’re your own customer. This is a very hard lesson I have to remind myself of all the time.

No. 9

Startups are in the business of urgency – If you’re not feeling the urgency, you either need to be talking to more people, or trying more experiments.

• There are plenty of other ways to build a business, but if you chose the VC money route, you need to get learning. Try Reddit, try Hacker News, try calling a friend, try texting a coworker, try LinkedIn messaging another founder. Try anything to learn more.

No. 10

Despite the need for urgency, you will burn out if you don’t occasionally take breaks.

• It is so much more fulfilling to get back into work after a half-day or a weekend break.
• I still am learning this lesson because at every moment I think I need to be doing something to move the needle forward for my company. This coffee-break has been one of the few days that I’ve not forced myself to actively work on Onlook, and yet I still ended up putting 2 low-pressure hours in.

No. 11

Your company won’t live or die by major big decisions, but mostly through the culmination of many smaller decisions (Points 2, 3, 6).

• The types of decisions you make should be dramatic enough to get you enough data to know where to go next. It’s why talking to users is helpful – sometimes just talking to 3 people will get you a ton of insight into how much someone cares about a problem and whether it’s worth solving.
• You’ll probably worry much more over small decisions than the larger ones, so try to focus on larger, higher-impact decisions.

No. 12

There is a baseline of performance people look for in assessing your startup. Do your best to hit that baseline.

• This is one of the reasons why San Francisco is the most successful startup hub: you can look around and understand very quickly what successful startups look like and emulate them.
• Being adjacent to other startups that are performing in this baseline is signal in of itself – getting referrals from other builders to investors, partners, and companies are a great way to show you're on the right level.

No. 13

The most important thing you need to do is likely what you’re avoiding.

• A great way to not “play house” is to tackle what you’re avoiding. Playing house will always be easy to do, but the hard stuff is where you learn things.
• You should practice lifting your “do hard stuff” muscle as much as possible so it becomes habit. You’ll feel a sense of adrenaline and relief when you try something hard – try to get that feeling as many times as you can during the week.

No. 14

Raising money is the most irrational, frustrating thing you’ll do.

• You’ll wonder why you have to go through the process. You’ll wonder how some people can be so bad at their jobs of getting back to you. You will have to grit through and smile through the process of dealing with the widest array of characters and personalities – both good but mostly bad.
• You will need to talk to over 100 people and be ready for every one of them to give you some reason as to why you’re not a fit for their fund at this time (Point 4).
• Investing is not the same as building – keep this in mind with every conversation you have with an investor. That’s another way of saying the advice you’ll get from investors will very likely be normie common-knowledge unless they are specialists or have built something before.

No. 15

The biggest challenge you’ll face is maintaining your own belief in yourself.

• The belief that you’re capable of overcoming hardship, that you will continue to persist against all of the rejection (Point 4), and that you’ll remain optimistic (Point 5) when things are not working out.
• The belief that even though there will be so so many bad days, you’ll wake up and do it again tomorrow. The beatings will continue until morale improves.

• This ties to many of the themes I’ve written about in the past, including:

• Don't be your first rejector

• The person you choose to be right now

No. 16

Finally, the only way to do entrepreneurship is your way.

• I have read so so so much advice, listened to so many podcasts, watched so many videos on everything related to startups. Some of the advice is applicable, but you should think of startup propaganda as a source of inspiration, not gospel you’re prescribed to follow.
• For example, if you want to “fake” the way you build your company by pretending to be someone else and it gets you results, then by all means do it.
• Treat all of the advice out there as frameworks and ideas that might be helpful but lean on believing in your own ability more than the hacks and tricks other people encourage you to follow. After all, at the end of the day you’re the one that has to go and do the thing.

I’m sure there will be many other truths to come in the months ahead, but I hope this helps other current and aspiring entrepreneurs navigate the wildly chaotic and fulfilling journey of making something.

If you want to follow along with my journey of building Onlook, I’m writing about it on Substack here.

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https://github.com/onlook-dev/onlook