“There are a lot of things that are outside of your control, a lot of external circumstances will determine the success of your idea, whether the market timing is right for this kind of service or whether the economy is right for your kind of service or whether we meet the right people who will finance our company. Many, many external circumstances are outside of your control and will affect the outcome and you have to be okay with that.”

“There are a lot of people from whom we can learn a lot and I think the one piece of advice, don’t underestimate anyone you come across, whether they are a blue collar worker waiting for the bus or they’re the server or bar tender at a restaurant or they’re a lower ranking employee. The smartest leaders that I have ever seen have always gone around the room and asked for everybody’s opinion.”

“Courage without genius might get you to where you need to go, but genius without courage almost certainly won’t.”

“You don’t have to be the best, but you have to be dangerous. You have to learn just enough to be dangerous to build an idea, concept it and show it to the world and then it turns out there are lots of other people, including all 170 employees that work at Instagram, who are much better at doing all that stuff than I am. But you need to find people who can be drawn to the idea that you build and then they end up taking it and making it even better.”

“A company is simply a group of people and as a leader of people you have to be a great listener, you have to be a great motivator, you have to be very good at praising and looking for the best in people. People are no different from flowers, if you water flowers, they flourish, if you praise people, they flourish. And that’s a critical attribute of a leader.”

”One way to conceptualize what makes a good product, good engineering is part of it, good design is part of it, but really it’s, one way I think about at least, is maximizing the probability that someone shows up at the front door of your store, your website or whatever it is and ends up with a solved problem.”

“Don’t necessarily think that you have to have the homerun and the huge Apple computer on your first start. I’ve spent a long time in my life with skills, just building little devices for fun, for fun is one of the key things. Because that drives you to think and think and think and make it better and better and better than you ever would if you were doing it for a company. Build things first for yourself, that you would want.”

“You should find a great partner, no matter what it is that you’re doing, and you should look for someone who has very high intelligence, very high energy and very high integrity. And you need all three of those, you can’t compromise on any one of them,the worst case is you end up with a smart, hard working crook, who ends up working against your interests. And integrity is something that takes a lot of time to spend with someone to figure out.”

“Do Something you are very passionate about and don't try to chase what is kind of the hot passion of the day”

“You have to have an emotional investment in what you’re doing. If you don’t love what you’re doing, failure is pretty much guaranteed. Success is not guaranteed by any means, but failure is much more likely, if you don’t love what you’re doing.”

“It’s very rewarding when you work on something you think is going to make a very big difference and yes, it’s a little bit harder, but I think the passion that one might bring with it brings so much more energy to that, that you’re more likely to succeed.”

“Because when you’re trying to differentiate, when you’re trying to do something different, there’s going to be that gut moment, that gut sense, “Is this right? Is this not right?” If you’re not having doubt, you’re not pushing the boundaries far enough.”

“What this all comes down to is doing something exceptional for your users, whether it’s in community, whether it’s in connection or whether it’s in design. This is our big advantage as a startup, is that we can actually get away with doing this. We can make this the core part of why we’re doing business.”

“When it comes to changing the world, what I’ve learned from Steve Jobs is if you believe in a Macintosh, if you believe in iPhone, iPod, iPad, if you believe enough, then you will see it. So you need to foster the belief in what you are dreaming so that it becomes a reality, which is very different than saying, “I don’t expect anybody to believe it until I see it.” You need people to believe it before they can see it.”

“This little idea explains why some organizations and some leaders are able to inspire where others aren’t. Every single person, every single organization on the planet knows what they do, 100%. But very, very few people or organizations know why they do what they do. And by why I don’t mean to make a profit, that’s a result, it’s always a result. By why I mean what’s your purpose, what’s your cause, what’s your belief? Why does your organization exist?”

“If you don’t love it, you won’t make it through the long period of pain that is inevitable. So make sure that you take care of yourself during the process, make sure that you take care of your mental health, your physical health while you’re doing it, because it’s a long road.”

“So when we see a kid with a lemonade stand it’s different than when we see a vending machine selling lemonade, even if it’s exactly the same product. Because the story around it is what people are paying for.”

“Understand that naturally nobody is interested in your idea, the world couldn’t care less and you have to persuade them and you have to show that you’re the one person out there that can do it.”

“Another quality that I think is important is being flexible-minded or open minded. I’m not saying you shouldn’t have a vision for your idea or your product, but you need to be open for changes.”

“It’s not just about doing focus groups, it’s not just about double checking your vision, it really is about integrating this concept of testing our ideas rigorously throughout the product development process, throughout the marketing process, even as we scale on.”

“Don’t think about, “How do I get big fast?” That will happen if you actually build something super meaningful and super important. So don’t think about what is the quickest way to success, think about what is the best way to building something important, that the world really needs.”

“If you know exactly what you want to be, you need to spend as much time with people that are actually that already.”

“I think when you are starting a new business, you don’t want to go after giant markets, you want to go after small markets and you want to take over those markets quickly.”

“What you really need to do is think about what is the smallest possible test that I can run for this idea, for this concept, for this theory, get it out there and get customers using it. Because your customers are going to be the ones to tell you if it’s really working or not.”

“ A classic entrepreneurial impulse to hold the idea close to you and not go tell people, because oh, the idea is so special. That’s almost always a mistake, because your actual, real competitive advantage is not that you have this idea that you have locked away in your closet, which may or may not be accurate and you have no idea which it is. Your actual competitive advantage is if you’re assembling the intelligence around “Does this idea work? What is the right team? What is the right learning?” and we’re essentially in motion.”

“You need to define all of the worst case scenarios in terms of financial loss, time loss, etc.., look at what you’ll learn if that happens and accept and come to terms with that before you ever start. If you don’t do that, then you go straight into battling the world, trying to conquer the world with rose coloured glasses on and the first time you hit a major hiccup you’re going to become really demoralised and you will quit.”

“So just go and do it, try, learn from it, you’ll fail at some things, that’s a learning experience that you need so that you can take that on to the next experience. And don’t let people tell you it can’t be done. Because often they will tell you it can’t be done and it’s just because they don’t have the courage to try it.”

“The hardest thing to do is start. You have all these ideas and everyone has an idea, but it’s really about executing the idea and building the idea and attracting other people to help you work on the idea. That is the biggest challenge. But the way to begin is to get the idea out of your head, draw it out, talk about it, program it if you’re a programmer or make it if you’re building something.”

“I think people that look for great ideas to make money aren’t nearly as successful as those who say, “Okay, what do I really love to do? What am I excited about? What I know something about? What’s interesting and compelling?”

“That’s how we really got to where we are, we saw things that we wanted to build and we just went out and built them. And it turns out when you build stuff that you like to use, there’s a good chance that there are thousands of other people that want to use it too.”

‘Constantly seek criticism. A well thought out critique of whatever you’re doing is as viable as gold and you should seek that from everyone you can, but particularly your friends.”

“There’s this expectation that you have to have in your mind, this sort of, “I’m going to change the world, make a dent in the universe” kind of ambition. But it’s actually okay early on to just kind of solve small problems in layers until you actually get to a point where you have the capacity to do that.”

“If you don't love it, you're not having fun doing it ,you don't really love it, you're gonna give up.”

“If you’re not coming up with 10 ideas a day… that’s why I have this thing, if I’m not coming up, if I’m not filling up this page every single day, then my idea muscle will atrophy. And I started this in 2001 and I still do it every single day. You have to come up with ideas every single day or the idea muscle atrophies. The good news is, after about six months of doing that you’re like a machine, people get surprised at how many ideas you could just have anywhere.”

“The definition of values is they’re the behaviours or principles that you religiously adhere to within your company. And when I say religious I mean that no amount of data will sway you from those principles. And the degree to which you have the courage to maintain your conviction around those ideas is the degree to which you’re going to be successful over the long term.”

“And so, when we’re coming up with ideas, we always ask ourselves, “What kind of new market is this creating?” and then also, “What part of my day and what problem is it solving?” And so I’ve gone as far as taking an entire catalogue of my day from the moment I open my eyes and writing down every single thing I do and then asking myself, “Is there something here?”

“Most start-ups that fail do it ultimately because they did not make something that people wanted. They made something that they thought people would want, but they were either in denial about it, about whether it was actually any good, or somebody else came along and made something that people wanted even more.”

“I think you should be spending your money on teaching and sharing, and so that might mean hiring a writer perhaps instead of a marketing person. And start writing and start getting people to listen to what you’re saying. You can’t talk about yourself all the time, because no one’s going to come back for that, but you have to talk about things that are relevant to your industry or ideas that you have and start to build that audience up.”

“So many things go wrong when you’re starting a company and often I think people ask, “What mistakes should you avoid making?” And my answer to that question is, “Don’t even bother trying to avoid mistakes, because you’re going to make tons of mistakes and the important thing is actually learning quickly from whatever mistakes you make and not giving up.”

“I half-jokingly with a lot of people said that my job is basically to be the assistant for the rest of the company. My job is to make sure that you have what you need, you have everything you need to kick ass, that’s my job. If you don’t have that, then let me know, because I’m not doing my job.”

“If you’re not utilizing an online community, then you’re at a disadvantage to those who are. You can be asking online communities what they think about your ideas or if they have any advice with what you’re working on. Not only will you hear from people who are passionate about the subject, but you’ll be hearing from people all around the world, each with their own experiences and stories that can help you.”

ANTHONY CASALENA, SQUARESPACE

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