Everyone Should Read, Write, and Think Alone

“I take a lot of time just to read and think about things by myself.” – Mark Zuckerberg

Maybe because I’m a natural introvert, but I like to sit alone and reflect. I like to step back from everything, slow it down, and think. That’s why I love writing in this blog. It’s a moment in my week that allows/forces me to think clearly.

My life has a million things going on at any moment. I work in tech, which means things are constantly changing. What worked yesterday doesn’t mean it will work today. I’m in a constant state of motion. Sometimes I feel like I’m reacting more than I’m thoughtfully moving forward. I feel like information comes in one ear and out the other.

That’s why when I read this quote by Mark Zuckerberg, it really resonated with me. When asked about his weekly work hours, he stated that he was only in the office for 50-60 hours a week. But he’s constantly thinking about Facebook. More importantly, he states that he takes a lot of time to read and think about things by himself.

I think more people need to do this. Regardless of what your occupation is, you should take time to read, reflect, and write. I love writing because it clarifies your thoughts. You don’t necessarily have to make your thoughts public. I also write in a journal from time to time, where I keep more personal thoughts. But it’s the same exercise as this weekly blog and similar to the annual exercise I do when I reflect on what I want. No matter the medium, I find it very cathartic to just sit back, read, think, and write.

If you’re having trouble getting started, let me pose a question to you. I’m currently reading Peter Thiel’s Zero to One. In it, he states that he often asks interviewees this simple question, “What important truth do very few people agree with you on?” What’s your answer to this question?

In a future blog post I will answer this question. But if you’re stuck on what to think and write about, start with this question.





TalkAnything Interview with Rachael King


In this episode of TalkAnything, I had the pleasure of speaking with Rachael King. I met Rachael on Twitter years ago. We finally met about a year ago, as she was making the move to Los Angeles.

Her move to Los Angeles coincided with a new position at DogVacay, as its new Head of Communications. Rachael’s journey to DogVacay is a great one. It’s one that any young professionals in any industry can learn from. Rachael started at a job that has nothing to do with her current career. But she turned her hobbies into her career, and hustled to meet the right people. It’s a great lesson on career growth and how to use technology to network.

FYI: I used new microphones for this interview. The way it recorded, my voice is in your left ear and Rachael’s is in your right. My voice isn’t as loud as Rachael’s voice, but that’s ok. You want to hear what she has to say more than me ūüėČ

Lastly, here’s Mr. Buttersworth’s Instagram account.

Does Work/Life Balance Exist?


Is it possible to have it all? Is there such thing as a “work/life balance?” I have chosen to believe that you can have everything and live with balance. I wrote about it earlier this year, it’s clearly something I think about and struggle with mightily.

I’m 31 but I feel old. Which is ridiculous because I’m not. But I see my friends going out all the time, seemingly having so much fun, and I can’t help but wonder…am I wasting my youth?

I had a lot of fun in my early-mid twenties. Up until the age of about 25/26 I went out a lot, drank a lot, cared about little. I knew I had dreams and ambitions, but when you’re getting really drunk on a Wednesday and waking up hungover to get to work on Thursday, how dedicated are you?

I started my first company a few weeks shy of my 27th birthday. Since then, I’ve felt like I’m constantly getting punched in the face. I’m happier about that I’m actually working on my dreams, but I question whether or not I’m happier. I look at Facebook and Instagram and I see my friends having really fun times. They’re traveling, drinking, sun bathing, and whatever else seems like ridiculous amounts of fun. While here I am on my computer, looking on with envy, feeling a bit frustrated, and confused.


But if I look at the flip side, are my friends accomplishing their professional goals? Are they on their way to accomplishing their professional goals? My suspect not. So I’m torn. Is there a way for me to enjoy my youth and focus on my career? Do I even want to be out drinking anymore, like my friends are?

I’m clearly in the midst of a mini life-crisis. I’m dealing with my internal conflict, weighing the juxtaposition between raging the raging twenty-something lifestyle and calmer, mature adult life. ¬†Can I ever balance this?

I don’t have the answer. I struggle with this, just as everyone else. I probably just think about it more than most. The only thing I am going to do is this…continue to have faith. Have faith that my hard work will pay off. Have faith that the life I envision will come true and that these years of struggle will be worth it.

What Do You Want?

what do you want

What do you want? It’s a question that I always ask my friends. “If there were no obstacles, what do you want in life? What’s your wildest dream?” I ask this to help them eliminate doubt and¬†to focus on what they truly want. Then I help them work backwards to figure out a plan to get there.

I believe that self-reflection is an underrated exercise, but one that’s extremely vital to an individual’s self-improvement. The most successful people are constantly reinventing themselves, always aware of who they are and their surroundings. Shortly after I started my first company, I started an annual exercise of asking myself a series of questions about my personal and professional life.

It’s been about five years since I first started this exercise. I have an Evernote document where I write down what I want, both professionally and personally, then I map out my strategy to get there. For the most part, my goals have remained constant.¬†There are minor tweaks based on experience but it has kept me on the path I most desire.

I bring this exercise up for two reasons. One, I’ve been making some decisions based on what I “should” do, not what I¬†wanted to¬†do. These are two different reasons for making a decision and when I choose what I should do, I’m never as happy. Second, a close friend asked me point blank, “What would you change in your life to make it better?”

Being presented this question forced me to say, out loud, what I want in my life. It was weird saying it out loud. But I was very quick to point out two things I’d do to make my current life more enjoyable. Now I’m focusing my energy on how I can improve myself in these two aspects of life. Which makes me feel happier, more focused, and more confident with my decisions.

If you’re interested in this exercise, below is¬†the template of questions I ask myself. The questions are simple, my answers are long and thought out. While it might not pertain to you, the part that I’ve actually found the most interesting is the last section where I ask myself, “Entrepreneurs I Admire.” The job functions of these entrepreneurs has been refined over time. I can clearly see where my journey is taking me and I’m quite happy with the direction.

What Do I Want in Life?



How Do I Get There?



What Do I NOT Want To Be?



What Do I Like to Do?


Who Do I Want to Be Around?


Entrepreneurs I Admire

Why Do I Admire Him/Her?

What Do I Want to Emulate?


TalkAnything – Interview with Joe Cannon

Screen Shot 2015-03-26 at 11.57.16 PMAlright, the TalkAnything podcast is back. This week I’m talking with my buddy Joe Cannon. Joe is the Director of Marketing at Sports Studio. He probably has one of the coolest jobs you’ve never heard of. He outfits commercials, TV shows, and movies, with any sports apparel you see.

Joe and I¬†have a great discussion about how he got into this line of work and how all the moving pieces go together when you’re dealing with brands, production companies, networks, leagues, etc. I thought our discussion about why you sometimes see official logos and why you sometimes don’t was really interesting. It’s something I’ve always wondered.

Here’s the link to the Jabari Parker/Gatorade commercial mentioned in the interview.

You can find Joe online everywhere with the username “joecannonballs,” like his Instagram account.

The audio is good, but the volumes change between my three transition. Whoops! So just be prepared for that. Otherwise, enjoy!

On Wisconsin! #FinalFour

I’ve got all year to write about growth hacking, mobile payments, and other tech related topics. Today, I’m still basking in the glory of the Wisconsin Badgers’ return to the Final Four.

It’s no secret that I’m a proud alum of the University of Wisconsin-Madison. I love my alma mater. I love the campus, the school spirit, and our athletic¬†programs. We have a lot to be proud of.

Our athletic department is one of the finest in the country. We do things right. Our football team doesn’t lower admission standards for athletes, yet we still have the second highest revenue of all college programs. In addition to winning on the field, we graduate athletes.

Congratulations to the Wisconsin Men’s Basketball team and the rest of Badger Nation. Looking forward to next week and our rematch with the University of Kentucky in the Final Four!

I Am a Feminist

This is my follow up post to, “Am I a Feminist?

Just a few months ago, I wrote a post, essentially asking out loud if I was a feminist. At the time I had a point of contention with the word “feminist.” I wrote:

My first thought when I hear this word is an eccentric woman, who makes a big fuss with every single issue related to women’s rights. I’d say my feelings toward this first reaction leans towards annoyance.

In hindsight, I sounded misguided. But I’m not going to apologize. I was being honest and I think that’s how you start conversations of change. (FWIW:¬†Even women have issues with the word¬†feminism) Since I wrote that post I’ve thought a lot about the word feminism.

In my meager attempt to offer some type of solution, I thought we had two options when it came to the word “feminist.”

Either we need to desensitize everyone to the word feminism, or we need to come up with a new phrase.

Perhaps desensitize wasn’t the right way to present change, but my intention was to find a way for people (both men and women) to feel comfortable calling themselves a feminist. Then I saw Aziz Ansari’s interview on David Letterman the other night. I think he explains feminism and the fear people have with the word perfectly.

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Like Ansari says in the video, feminism is the belief that men and women should have equal rights and opportunities.

When you break it down like that, it’s much easier to align yourself as a feminist. Block out Precious’ mom attacking you, and it’s hard not to feel comfortable calling yourself a feminist.

Hi, my name is Jesse and I’m a feminist.


Last week, I posted on Facebook that I had backed Girls Driving for a Difference on Kickstarter. Four female Stanford students will be driving around the country and teaching middle school¬†girls the design process and empowering them to be tomorrow’s leaders.

In my Facebook status I wrote:

If we want more women in tech and leadership roles, we need to start empowering young girls today. I want my niece to have every opportunity available to her in twenty years. If you are aware of other noteworthy organizations/projects that I can support in some way, please let me know how I can help.

I love my niece to pieces. I don’t have children or know when I will.¬†But as I get older, I’m starting to feel that desire to make the world better for the next generation. To me, that’s my niece. She’s an extremely bright five-year old. I hope she pursues a career in math and science. But it’s her life, not mine. I’ll support her in whatever endeavor she chooses. But what I do want is for her to have all the opportunities at her disposal. I want her to expel her energy for greatness, not equality.

My niece, Aya.

My niece, Aya.

Therefore I will be doing my part to help fight¬†for equality. Right now, I don’t have a ton of money or influence. I’m not in a position to hire more women executives in technology (yet!). But what I do have is this blog and my everyday life. I’m going to do what I can¬†to spread the word around me that feminism isn’t a bad word and encourage others to stand up for feminism (including you reader!).

Please let me know of any events, organizations, or projects that I can support in some way to continue to spread the word. In my youth, I fear I might have been misogynistic and I’m paranoid¬†I still project misogyny on occasion to the world. I’m not a perfect person, but I’m striving to improve myself and the world around me. Let’s do it together.

TWIST: David Heinemeier Hansson

I’m in Phoenix this weekend, getting some much needed R&R with my friends. We’re going to be going to a Brewer’s spring training game and some hip hop festival in Tempe. It’s going to be a blast. I know you can’t wait for my Sunday posts (sarcasm) I’m leaving you with this fantastic interview with David Heinemeier Hansson.

David is the co-founder of Basecamp and the creator of Ruby on Rails. He’s a a top notch entrepreneur/technologist (and a race car driver on the side). But the best part about him, to me, is how pragmatic he is when it comes to building businesses. He has great insights on companies, especially tech valuations.

This interview (conducted by Jason Calacanis for This Week in Startups) is more than 90 minutes long, but it’s entirely worth your time. Enjoy!

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Bad Startup Ideas



I was at the Launch Festival last week up in San Francisco. I met a lot of people and heard a lot of pitches. As someone who aspires to be an investor, I like to put on an investor’s hat when I listen to these startup pitches. Would I invest? Why or why not? Since I can’t do much due diligence on the team and traction, this exercise is mostly about the idea behind the startup. It’s a limited exercise, but it’s good to fire up that part of my brain anyway.

I left San Francisco a little discouraged. Usually I feel reinvigorated by smart people, bursting with enthusiasm. Instead, I felt discouraged because I felt like I was hearing the same idea, packaged with a different bow. Maybe that’s what it’s like being an investor? The usual buzzwords like big data, mobile, and real-time were prevalent.¬†The biggest buzzword was “connect.” So much so, one of the main sponsors was a startup called Connect. Whether it’s your cloud apps or someone in your immediate vicinity, startups wanted to connect you using your mobile device, analyzing big data, in real-time.

Hyperbolic app descriptions¬†aside, I felt like I was listening to the same businesses over and over again. Startups and products are supposed to be about building great problems that solve real problems by unquestionably intelligent and determined people. I felt like there were too many people who just wanted to get into the startup game and were forcing a “problem.” As I tweeted later, the problems being solved felt more like minor inconveniences than real problems.

This mindset is also a double edged sword. That’s because we don’t know what the next big ideas are. No one really does. Venture investors can give you a good idea based on the volume of pitches they receive, but even they don’t really know. Case in point, Twitter. When I first signed up for Twitter in 2008, I didn’t get it. It took me a few weeks¬†from the time I signed up to the time I sent my first tweet. You could argue it wasn’t solving a real problem I had. But today Twitter is a $30 billion company and I use it nearly every day. It solved an information and communication problem I didn’t really know I had. Could the minor inconvenience I overlook actually be the root of the next billion dollar company? The other day, I was skimming Twitter and I saw a great tweet from Sam Altman (President of Y Combinator).

I had to read it a few times, but this¬†tweet¬†rang true to me. It is easy to make fun of someone’s startup. I’m sure I’ve made fun of someone’s location-based, social network for dogs at some point. But that’s not what I like about startups. That’s not what I like to talk about with my startup friends. I much prefer to discuss the viability of an idea and how it can be tweaked into something great. How can I help the founder gain customers or tighten their messaging? How can this idea go from zero to a million? I love the high¬†of walking away from a meeting with someone, feeling smarter and rethinking how I do business. That’s exciting and part of the reason why I aspire to be an investor.

I love startups because of its blend of hope, passion, naivet√©, and possibly ignorance. The world is not perfect and there is always a problem to solve. I hope anyone out there reading this thinks twice before mocking an entrepreneur’s ideas and dream. It’s easy to be a dick and laugh. It’s not easy being helpful, like really helpful and not that generic advice you hear “advisors” give out.

Instead, figure out a way to help the entrepreneur. Everyone has had a bad idea. But it might just take a slight nudge to the left to turn that bad idea into a great one. Would you rather be the person nudging someone along? Or the “realist” who masks negativity by “telling it how it is?”