From Jason: Today we’ve got a guest post with Jonathan Gurrera, on some of the crazy behavior change tactics he used to power through rejection therapy.

He’s an account strategist at Google, a gig he earned after investing dozens of hours of preparation through a system of gamification that he created for himself. It’s fair to say that he’s pretty obsessed with engineering his behavior and I think there’s a lot to learn from Jonathan’s approach to behavior change.

So enjoy and here’s Jonathan:

My experience with rejection (and how it benefits you)

One of my first encounters with The Art of Ass Kicking was reading about Jason’s experiences with Rejection Therapy. The idea of Rejection Therapy resonated with me for one reason, and one reason alone: rejection scares the living crap out of me. Nevertheless, handling rejection is such an important life skill, I didn’t feel it was an option to allow myself to be affected so strongly by it.

While all rejections are less than pleasant, I tend to let rejection control me most in social realm – especially when it comes to introducing myself to strangers or asking girls out. Quite aware of this, I’ve recently decided it was time to be more proactive with this area of my life. But rather than use a brute force strategy (i.e. pound shots when I’m not feeling social at a party), I wanted to create a system that subtly, but consistently guided me to take positive actions, even with the risk of rejection present.

My weapon of choice for creating this system was gamification, the application of game mechanics to systems where they may not have otherwise existed. Although I was new to the use of gamification for rejection therapy, I’m no stranger to using gamification to get things done, build habits, and achieve epic wins. In this post, I’ll be focusing on the use of gamification for systematically overcoming rejection. I’m still in the midst of this long-term experiment, so I’ll be sharing my progress thus far, with the hope that you can use these techniques in your own life. Continue reading

Ignite is a very cool type of event that’s held in cities across the country with a simple premise: interesting 5 minute talks given with exactly 20 slides that forward every 15 seconds.

Public speaking is a skill I think it’s worth developing and Ignite looked like a fun event (I went to one in Mountain View a few years back), so I submitted a proposal to speak at Ignite San Francisco about my experiences with Rejection Therapy.

If you aren’t familiar with Rejection Therapy: it’s a social game invented by an introverted guy named Jason Comely, and the one rule is that you must get rejected by another person at least once, every single day.

The Presentation

My other Rejection Therapy Posts:

Ignite San Francisco is run by Jon Bishop and Patti Chan and they do a fantastic job. The event was held at Public Works and was packed. Probably over 150 people came to support the speakers and they were a great (ie: supportive) crowd. I was also impressed with the creativity and delivery of the other speakers – here are some of my favorites:

What did you think of the presentation?

Click here to leave a comment with one thing you liked and one thing you think I could do better on a future talk.


Things have been super busy lately, but I promise a more regular blogging schedule is coming soon. In the meantime I thought I’d highlight some things I’ve been up to across the web that you might not have checked out:

Startup Fitness

Derek and I wrote a series of posts about working out & entrepreneurship. The first one was about How Working Out Makes Us Better Entrepreneurs, which I cross-posted here. The other two are excerpted below.

Start Up Fitness: An Entrepreneur’s Guide to Working Out

We recently wrote about how working out can be your secret weapon as an entrepreneur. It gives you more energy, stronger focus & decision-making abilities, better ideas, and deeper rest– and that’s just for starters.

But if working out is so great, why aren’t we all doing it? Well, no time, too busy, not enough energy, don’t know where to start, putting it off for later, will start tomorrow, etc… We know it’s hard to fit working out into a crazy busy life. But it is possible. And worthwhile. Living a healthier lifestyle is one that’s built step by step, one smart choice at a time. But if you’re ready to start down that path of a more energized, focused, and productive life – here are our best strategies on how to get started: (Click to read more)

Startup Fitness Advice from Battle-Hardened Entrepreneurs

We recently wrote about how working out can be your secret weapon as an entrepreneur and shared our entrepreneur’s guide to working out. This time, we turn to 14 battle-hardened founders and entrepreneurs who prioritize fitness and ask them what they do, why they do it, how they find the time, and what their advice is for others. Without further ado, here’s the awesome stuff they said: (Click to read more)

6 Thoughts on Online Dating from a Guy’s Perspective

This is a post I wrote for Kat Richter during our recent blog swap. Her blog is all about dating (most off people she’s met online) so I wrote about something I don’t cover much here: dating. Here’s the intro:

Hey guys – I’m Jason! I’m a twenty-something guy who grew up on near Boston, went to school in California (Stanford) and now live in San Francisco.

I write a blog called The Art of Ass-Kicking which means I mostly blog about things like taking cold showerslessons learned from working at a startup, and getting personally rejected 30 days straight.

One topic that doesn’t get much coverage is my dating life (surprise, surprise). Which makes it great that I’ve been partnered here with Kat for this blog swap.

I’m a big fan of online dating (as the co-founder of an Internet startup, I find that it’s the only thing that gets me out of the house and meeting people) and I know Kat has some experience with it too.

There’s definitely some big differences (in my mind) about about online dating from the male vs female perspective– and perhaps from the East Coast and the West Coast. So without further ado, here are six thoughts from me on online dating– Some of these are lessons, some are questions some are just observations. Enjoy! (Click to read more)

Rejection Therapy Podcast continues

Though I haven’t been talking about it lately, I’ve continued to host podcasts with Jason Comely around the topics of Rejection Therapy. In two recent podcasts, we discussed Rejection Therapy being optioned for a reality TV series, as well as the lessons of humility and persistence learned from doing Rejection Therapy. Check ’em out:

Rejection Therapy Reality TV Series? Here’s the Scoop: Podcast 19

Being Wrong and Rejection Therapy for Start-Ups: Podcast 18

Doing Rejection Therapy has allowed me to meet all kinds of interesting people. One of them is Matt Ramos, a college student in California. He’s in the process of transforming himself from being a shy quiet guy to a fearless doer who gets after his dreams. I thought I might share his story with you here. I hope you enjoy it!

– Jason

The Power of Having a Mindset of Infinite Opportunity

By Matt Ramos

I was a huge introvert throughout my teenage years.

I was extremely timid around all people because I made assumptions as to what they were thinking about me.

Being in a shy mindset created a life where very few doors opened for me. Or even if many doors did open, I never gave myself a chance to walk through it due to the fear of being embarrassed or rejected.

The few times I did open the door only revealed humiliating experiences. I was rejected by my high school crush of two years. I didn’t fit in with anyone because I didn’t want to be another face in the crowd, which made people call me weird. I had it rough because I was the second quietest kid in the school. So people would give their sympathy to the shyest kid in the school, whereas I was simply a shadow.

So for the next couple of years, I shut myself out from the world. If the world would be that terrible, then why should I put myself out there?

After more negative experiences, I finally stumbled on the SFGate article that features Jason Shen.

I knew I had to follow the example that was given in Rejection Therapy.

Rejection Therapy Begins

In January and February of 2011, I did a daily rejection everyday. I was able to ask people if they wanted something I offered (like food), ask girls out, ask people to study with me, ask someone for a sip of her drink, and ask people to catch up with me.

For example, there was a girl in front of me in my class that intrigued me. She seemed to be interesting. Then I thought to myself, “How can I benefit her?”

When you think in terms of benefiting that person, then they are more likely to accept. Everyone would say yes to something that benefited them right?

So on the third day of class, I finally got the courage to ask her, “Hi, so what did you think of our professor?”

She told me that, “Well he doesn’t really look like a professor; he looks more like a surfer!”

Then we ended up chatting for a few more minutes after that. Before she left, I asked her if she wanted to study with me in that class. She gladly accepted.

Throughout that whole class, we ended up chatting together. We built up rapport and started making jokes with one another.

We lost touch after the class ended because she was from out of town.

However, taking that chance enabled me to get a good grade in my class and kept me from being totally bored in that class.

I’ll take a risk of rejection for those benefits any day. Instead of sitting around on my iphone and playing Angry Birds all day, I found out that talking to strangers could be more rewarding.

Create Your Own Infinite Opportunity

It’s like an once-in-a-lifetime experience except you have full control over how you can get it. You don’t have to wait around passively for opportunity to come. You can create it at any moment.

You have the power to create as many door-opening opportunities as you’d want if you change your mindset in one way.

That one way is letting go of a desired outcome and letting that outcome just happen.

If the girl rejects you, you win because you just got rejected. If she accepts your date, then you win because you just got a date. It’s a win-win situation.

If you ask someone to help you with something (study, projects, etc.), and they say no, you win because you just got rejected. If they say yes, then you’ve got the help you need. It’s a win-win situation.

When you can think of rejection as a door-opening experience rather than a feeling of inferiority or embarrassment, then you have an infinite amount of doors in front of you all the time.

Rejection can hurt but will you let that fear of being hurt take all the opportunity away from you?

It’s your right to take a chance.

The rest is up to you to actually take that chance.

If you want to start your own 30-day Rejection Therapy challenge, you can go to, ask Jason about it, or contact me.

Matt Ramos is a college student who wants to eliminate fear, create possibilities, and contribute to the world as much as possible by the age of 30. Rejection Therapy is just one of his tools to make that vision a reality. You can visit his site here at

Asking a girl out on a date can be a scary thing. Ask any guy. Now imagine standing up in the middle of a crowded metro subway train and announcing out loud to every female on the train that you’re looking for someone to take you on a date.

Could you do it?

Well, that’s exactly what Maurice Ellis did as part of his 30 day rejection therapy challenge. And he got it on tape too. Pretty awesome.

In Episode 12 of the Rejection Therapy Podcast, Jason Comely and I interview two folks who have embarked upon the rejection therapy challenge and share their war stories. The podcast is a bit longer (50 mins) but it’s worth it – the stories are both hilarious and inspiring. And if you want to catch every episode, you can join 1,400 other folks and subscribe on iTunes.