Or: How to regain confidence after you’ve lost it.

Dear Friend,

How’s it going? Alright? You don’t look alright to me.

You look like you’re going through rough times. Like you’ve had a couple setbacks and now you’re not so sure of yourself. Like maybe you’ve lost your way.

I don’t see that swagger in your walk any more. No wink and grin that says “Watch what I’m about to do.”

And of course, your results.

Your work is dull. Mediocre. You’re going through the motions – putting in the hours but not really giving it your best. You’re playing scared. You’re watching your back instead of charging ahead. You’ve lowered both the expectations you’ve set for yourself, and for how others will treat you.

You look like you’ve given up on yourself.

But guess what? Even if you’re giving up on you, I’m not.

I believe in you. I believe in what you’re capable of. I believe in what you’ve done, where you’re going and who you will grow to become.

I’ve been there man – been in the dumps because I screwed up. Everyone was counting on me and I blew it. It sucked. Hard. I know things have been hard for you. But you gotta shake that off. Don’t let the bastards get you down you know?

I know, easier said that done, right?

But there are tangible ways of getting there. Like winning some small victories.

Set some little goals for yourself. Maybe it’s going for a 10 minute walk. Or finishing two chapters of the book each week. Or it’s coding up one tiny shippable change to the codebase.

Earn little wins and start remembering what success feels like.

Take some time everyday to feed your mind.

From now on your mental diet is cutting out junk food. Like Fox News. Or any news for that matter. No more bad economy crap. No more  getting into flame wars with trolls on Reddit.

Instead read about how Airbnb almost hung up the towel again and again before becoming a $1B company. See  Heather Dorniden fall flat on her face in a championship 600m race only to come back and win. Or how Nelson Mandela spent 27 years in prison, many of them in solitary confinement before getting elected President of South Africa in their first ever multi-racial elections.

Or just order one of the many Chicken Soup for the Soul books off Amazon. Seriously! There’s a reason they’ve sold hundreds of millions of copies.

Our world is one of second chances, of comebacks and turn arounds. The more you fill yourself with the strength of others who have turned around, the sooner yours will be. Continue reading

Photo credit: Think different! by gianlucachiari via Flickr

Coming up with startup ideas is hard. Trust me, I know. Before my team and I settled on the current idea we’re working on, we spent many weeks brainstorming different things to do. Three different people with similar backgrounds can still produce a wide array of interests, skills and areas of expertise.

Here are some of the questions you might find useful when brainstorming your startup idea. They definitely helped us.

18 Questions To Ask When Brainstorming Startup Ideas

  • What do you love about your favorite products? How can you do that in a different way or for a new market / customer base / new use case.
  • What are problems you face in your life?
  • What are problems you see happening in other people’s lives?
  • What ought to exist in the world right now that doesn’t?
  • Are there obvious new behaviors that people will engage in 5-10 years from now? How can you build the technology to enable that behavior now?
  • Where are there groups of people who are struggling to do something where your product could make it much easier for them?
  • What kind of business would be really fun / exciting personally for you to build?
  • How can you take something that’s already pretty good and make it 5x better?
  • (10 more after the jump)
    Continue reading

Can’t see the video below? Click through to the blog post.

I used to hate running. As a gymnast, the 90 feet down the vault runway was the farthest I had to go – except once in a while on Saturdays where we’d go out running and I’d breathlessly stumble my way through a mile or two.

I’m now running a couple times a week and loving it.

I’ll write more about this new found love soon – but this old Nike commercial just reminded me how integral running is to the human experience. Definitely gets me pumped for tomorrow morning’s run.

Or: How I Transformed into a Douchebag of Epic Proportions

I recently read a great post by Jared Tame, author of Startups Opensourced on the process he uses to land meetings with almost anyone. It was great advice but he definitely got some heat for it – check out some of the comments on Hacker News:

  • This has to be one of the lamest things I have ever read on hacker news.
  • coincidentally, this is the same hack that celebrity stalkers use to get free restraining orders.
  • Good GOD this is a terrible system.

Here we have a guy who wrote a really valuable book where successful startup founders shared their hard-earned wisdom – and shares the actual technique he used (not just an idea he had) about how he was able to connect with these famous and busy people. This is really valuable stuff.

And while lots of people appreciated that, he got tons of hate for it – so much that he had to write a followup post. How is that fair?

It’s not. But guess what – it also won’t stop him from becoming successful. Consider this:

  • Every successful individual you can think of has a pack of people who just hate their guts.
  • Every successful company has people who think their products are worthless.
  • Every successful book / article has people who think the ideas are stupid and wrong.

Want to know my new motto?

Love the hate.

Embrace it. Realize that if you do something or say something and no cares – you’ve got a problem on your hands. The articles that were my most popular were also the ones that got the most hate:

What’s that line from Gandhi? “First they ignore you. Then they mock you. Then they fight you. Then you win.”

Mocking (aka hating) is a step up from ignoring. Having haters, more than having fans, lets you know you’re on the right track. Lots of things can generate positive feelings – few things inspire intense dislike. I would say the former are more likely to be mediocre and the latter are more likely to be great.

Of course the caveate here is that there’s a difference between critical feedback and hate. Critical feedback is something you can use to improve what you’re doing – make it better, more useful, more impactful, more sustainable. It’s important to always get feedback from the people who use/consume what you produce and from people who have a good/wise perspective on what you’re doing. Allow that feedback to inform your efforts. Ignore it at your own peril.

Hate is produced by people who aren’t trying to be helpful. Hate is done with a desire to tear down, to ridicule and mock for the purpose of destruction and marginalization.

Hate is when people post this on your “What Should I Write About” widget

(That’s my widget at some point last year, by the way)

Hmm – good question dude. The exact moment? I think it was sometime after dinner on March 12, 2009. I was over at your house and about to do your mom when I thought …

But in all seriousness, I don’t care that this guy was trolling me. I would laugh every time I saw this as the top suggestion. It meant I was saying something that struck a nerve. Now if all my feedback was stuff like this, I would reconsider what I was doing. You probably want to make sure your balance of positive to negative feedback is better than 50/50.

The fact is, I get tons of emails and comments from people who tell me they love what I’m writing about and really get motivated and learn stuff from reading my blog. It’s at least 70/30 if not better.

It’s the people who get value out of what you do. Those are the people you should care about if you do any creative work.

So remember – love the hate, because without enemies you are nothing, and continue to speak, write, build and work fearlessly towards the things you believe in.

I’ll close out with some wise words from Mr. Ralph Waldo Emerson from his fantastic essay Self Reliance.

Speak what you think now in hard words, and to-morrow speak what to-morrow thinks in hard words again, though it contradict every thing you said to-day. — ‘Ah, so you shall be sure to be misunderstood.’ — Is it so bad, then, to be misunderstood? Pythagoras was misunderstood, and Socrates, and Jesus, and Luther, and Copernicus, and Galileo, and Newton, and every pure and wise spirit that ever took flesh. To be great is to be misunderstood.

I co-wrote a post with the awesome Derek Flanzraich which first appeared here: Protip: How Working Out Makes Us Better Entrepreneurs – got a fair amount of attention on Hacker News too. Hope you enjoy it! We’ve got another related post coming up so make sure to keep checking Derek’s site as it’ll post there first. (photo credit “Pumping Iron” by Midiman on Flickr)

We’re entrepreneurs. We pour unbelievable amounts of time, hustle, and blood into our companies, making sure the product is amazing, the users are delighted, the team is inspired, and the investors are excited about the future.

There’s a lot to do and we’ve got to have the energy and the stamina to last through some very full days. It’s not easy, but we’ve been pulling it off. What’s our secret weapon in this battle against crushing work loads? It’s not an app. It’s not a pill. It’s not a version of GTD. It’s just a simple thing we call working out.

Surprised? You shouldn’t be. Working out isn’t just about looking sexier, but about getting more out of your mind and body. Most entrepreneurs who get regular physical activity find that there are many other (more practical) reasons for heading to the gym/bike trail/yoga mat. Here’s why we do it:


Perhaps it’s strange to think that expending energy provides more of it, but a 2008 study found that regular low-intensity exercise increased energy by 20% and reduced fatigue by 65% for sedentary people. Work days are tough, big deadlines are stressful, and there are always so many things to do– but we’ve found just an hour in the gym can give us the extra juice we need to power through the day. And on the really busy days when we don’t have an hour to spare, we’ll usually still end up taking 20-25 minutes for a short run, brisk walk, or a set of pushups & situps. We blow off steam and then return happier and more energized.


Working out also helps us get mentally sharper. When you’re constantly juggling different tasks and keeping a variety of perspectives in mind, you’ve got to find ways to bring it in. Sometimes that means clearing your mind completely. Trust us- when doing that third set of squats or pushing for the final mile on that run, you aren’t going to be worried about your user growth or the bazillion things you want to change about your website. Clearing your head can help you be more productive when you dive back into the issues.

Additionally, physical activity directly improves your ability to think and make the right calls. By improving your circulation, your body can pump blood and deliver nutients and oxygen to your key organ (like your brain) more effectively. Physical activity does a killer job of delivering nutrients and oxygen to your tissues. One study, for example, used neuroimaging to demonstrate that older adults saw measurable increases in focus and decision making after engaging in a 6 month fitness regimen. Another study in 2010 found moderate exercise resulted in a short-term 5-10% improvement in executive function. So working out can help you be sharper and avoid making blunders that you’ll regret after.


What does Brad Feld, founder of Tech Stars do when he wants to think about an idea? Hegoes for a run. Bob Iger, President & CEO of The Walt Disney Company, works out at 4:30am every morning with a personal trainer. OnSwipe’s CEO, Jason Baptiste, just raised a $5M Series Awesome– but he’s been working out for more than 10 years and constantly tweets about being at Crunch late into the night. We’re constantly surprised by how many important insights come from things that are totally unrelated to work. One of us, for example, swears by taking long showers. Another on taking long car rides without any set destination. It makes sense right? How many breakthroughs happen while staring for hours into a computer screen?

Again, the evidence isn’t just anecdotal: one study showed that participants that engaged in moderate cardio exercise showed more creativity immediately following the exercise, with the boost continuing at least 2 hours later. In the longer term, another study found the brains of people who exercise regularly have higher levels of brain derived neurotropic factor, a “factor” that ultimately increases capacity for knowledge. Working out just gives you better ideas.


Sleep? What’s sleep? Unfortunately, there’s pretty definitive proof a good night’s sleep can improve your concentration, productivity and mood. And, worse, lack of sleep isstrongly correlated to weight gain. But the good news is regular physical activity can help you fall asleep faster and deepen your sleep, too- as long as you don’t work out to close to bedtime. And by the way, the good night’s sleep is pretty non-negotiable. A recent New York Times article reported a study that showed people who slept 6 hours a night for two weeks had the cognitive equivalent of being drunk. You don’t drink (a lot) on the job do you? Then get more rest.

Long story short, not only will working out make you healthier and look better (with other unintended, but awesome side effects like, say, improved confidence), but also it will improve your energy, focus, efficiency, inspiration, and rest. At least that’s what we’ve found.

Give it a shot – we promise you won’t regret it. And if you need help making it work, stay tuned. The next part of this series will give some practical pointers on how to get more exercise into your schedule.

How does working out make you a better entrepreneur? Let us know in the comments!

Jason Shen is the cofounder of an early stage tech startup in San Francisco. He’s a former NCAA gymnastics national champion, can do 100 consecutive pushups and helps people make things happen at his blog: The Art of Ass-Kicking. You can reach him at jasonyshen [at] gmail [dot] com or @jasonshen.

Derek Flanzraich is ceo & founder of Greatist, a high-quality health & fitness media startup working to inform and inspire people to make one healthier choice per week. He loves any exercise that’s named after superheroes. You can reach him at derek [dot] flanzraich [at] gmail.com or @thederek.

Want to read other stuff by us? Check out Winning Isn’t Normal by Jason and Build Empires, Not Businesses by Derek.