If there’s one thing I’ve learned from running a handful of startups (including some great successes and some huge failures), it’s that maintaining the motivation and drive needed to push forward when you’d much rather be drinking beers with your friends can be tremendously challenging.

So if you find yourself in this position, don’t worry – I’ve got a present for you!  The following inspirational quotes have all helped me to stay on track when I’ve been struggling, and I hope they do the same for you.

 “Running a startup is like being punched in the face repeatedly, but working for a large company is like being waterboarded.” – Paul Graham (co-founder of Y Combinator)

I’m not going to lie – I’ve loved this quote from the first time I heard it.  There’s something so visceral about the phrase “being punched in the face repeatedly” that really rings true for me, considering the number of challenges I’ve faced throughout my business career.

When it comes to startup life, there are definitely good days and bad days – not to mention very bad days when you do feel like you’re being hit over and over again.  But it’s important to keep in mind what the alternative is.  While I’ve had the privilege of working for some great companies, this quote always reminds me that I’d much rather be working on my own on business ideas I’m passionate about than following somebody else’s lead.

“The very first company I started failed with a great bang. The second one failed a little bit less, but still failed. The third one, you know, proper failed, but it was kind of okay. I recovered quickly. Number four almost didn’t fail. It still didn’t really feel great, but it did okay. Number five was PayPal.” – Max Levchin (former CTO of PayPal)

I talked about how important I believe failure is in my post on “50 Lessons I Wish I’d Learned in School,” but this quote really illustrates why this is the case.

Just think about what would have happened if Max had gotten discouraged after his fourth failure and decided to take a steady administrative job instead of chasing his entrepreneurial dreams.  Sure, there are plenty of people out there that don’t like Paypal, but you can’t deny that the service itself wasn’t revolutionary.   Without Max’s resolve to keep pushing forward – which you should absolutely strive to emulate – the web would certainly be a very different place.

“So often people are working hard at the wrong thing. Working on the right thing is probably more important than working hard.” – Caterina Fake (co-founder of Flickr)

Really, being a successful entrepreneur isn’t just about working hard – although, yeah, that’s certainly a big part of any business’s success.  What Caterina is getting at here is that working hard on the wrong things isn’t that much better than just failing outright.

Unfortunately, it’s often difficult to tell what these “right” and “wrong” things are.  Developing the intuition needed to know when to call off a project that isn’t likely going to result in a success isn’t easy, but it’s a vital part of any entrepreneur’s personal growth.

“A few years ago, I felt like I was stuck in a rut, so I decided to follow in the footsteps of the great American philosopher, Morgan Spurlock, and try something new for 30 days. The idea is actually pretty simple. Think about something you’ve always wanted to add to your life and try it for the next 30 days. It turns out, 30 days is just about the time to add a new habit or subtract a habit – like watching the news — from your life.” – Matt Cutts

Over the past two years, I’ve picked up four separate hobbies – attaining mastery in each before moving on to the next.  And while these personal goals haven’t been directly related to my business, the discipline that I’ve developed as a result has definitely made an impact on my success with Single Grain.

So I love to see someone as high up on the food chain as Matt Cutts talking about how important it is to cultivate a wide variety of skills and experiences.  Seriously, if you ever feel like you’re stuck in a rut, you can’t go wrong with following his advice to try something new for 30 days.

“Not having a clear goal leads to death by a thousand compromises.” – Mark Pincus (founder of Zynga)

This is another quote that I love for its bold language.  The sentiment it contains is so true, and if you’ve ever found yourself feeling wishy-washy about big decisions, you know how easy it is to be swayed by the compromises recommended by others in your life.

Personally, I try to keep this quote at the back of my mind for whenever I feel that sense of indecision creeping in.  Knowing that the influence of others could lead to my business’s “death” is a great reminder for me to find my purpose and make decisions that resonate with that goal.

“Entrepreneurship is living a few years of your life like most people won’t so you can spend the rest of your life like most people can’t.” – Unknown

In a way, this quote sums up all of San Francisco to me.  Part of the reason I love living here is that everybody is running around and hustling on projects they care about – even if that means trading fun hours spent hanging out around the city to sit hunched over a computer desk.

Sure, the entrepreneurial lifestyle isn’t always fun.  But we’re not in it for the fun – we’re in it for the lifetime of financial reward that can come from putting a back-breaking effort into projects we care about.

“It’s rough out there no matter what profession you’re in. I’ve been in the business world and I’ve been in government. People ask me all the time ‘what’s the difference?’ I always tell them, in the business world, it’s dog-eat-dog and in government it’s exactly the reverse. Don’t be afraid to assert yourself, have confidence in your abilities and don’t let the bastards get you down.”Michael Bloomberg

I love Michael Bloomberg’s “balls to the wall” attitude in this quote.  Business isn’t just providing value and engaging with customers – it’s also making hard decisions and fighting to remain competitive in industries that tend to chew up startups and spit them out without a second thought.

Running a business means being tough.  If you aren’t able to stand up for yourself and hold on tight when nay-sayers try to bring you down, you might be suited for the entrepreneurial path.

“If you live for weekends or vacations, your shit is broken.” – Gary Vaynerchuk

Now, barring the fact that most SF entrepreneurs like me don’t actually *have* weekends or vacations, Gary’s right on the money.  Having a passion for the projects you commit yourself to is so vitally important to the long-term sustainability of your career.  Really, you’ve only got this one life – so why on earth would you spend your working years toiling away in jobs that don’t line up with your interests or skills??

“What if you began to expect the best from any situation? Isn’t it possible that you could write new chapters in your life with happy endings? Suspend your disbelief? Take a leap of faith? After all, what have you got to lose but misery and lack?” – Sarah Ban Breathnach

I’m not really into “The Secret,” so I’m not going to tell you that wishing magical thoughts is going to make all of your dreams come true automatically.

However, I do think there’s something to be said about maintaining a positive attitude and taking leaps when most people would rather stay planted with two feet firmly on the ground.  Entrepreneurialism requires a certain amount of “jumping in” – and you won’t be able to do this if you’re always worried about taking the logical approach to everything.

“Even if it’s a bit edgy, a bit out of your comfort zone, saying yes means that you will do something new, meet someone new and make a difference in your – and likely in others’ lives as well. Yes is what keeps us all young. It’s a tiny word that can do big things. Say it often.” – Eric Schmidt (former CEO of Google)

If you’ve ever seen the episode of “It’s Always Sunny in Philadelphia” where Charlie and Dennis make their way to Atlantic City for an animal rights benefit, you’ve seen this principle in action.

Saying “Yes” – even when you ordinarily wouldn’t – opens up doors and exposes you to new opportunities that you wouldn’t have had access to otherwise.  Sure, it might result in more work on your part or more commitments on your time, but opening yourself up to new experiences almost always results in more significant benefits than you ever imagined possible.

And really, you can always bow out gracefully later on if you need to J

Got any other quotes that I should know about?  Share the inspirational sayings that help to keep you on track in the comments section below!

  1. to be honest in all the quotes Michael Bloomberg wins the game! I am actually running a startup and this time of my life is lovable but crazy…

    People around me and the one who care for me dont really understand why i am at the front of the computer all day long and nights… sleepless nights!…Its exactly rough and its exactly dog-eating-dog! but the matter of the fact is is love this and i still want to be on this path!

  2. “Next to knowing when to seize an opportunity, the most important thing in life is to know when to forego an advantage” BENJAMIN DISRAELI

  3. And personally, I’m worried about Trim Routering beef from animals that have been used for centuries to improve physical endurance. Today the World Health Organization’s
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