Over One Million Real World Ready!

Apply for a $1,000 grant for graduation gift books…

We’re thrilled to share that we’ve helped over 1,000,000 new graduates be “real world ready” with topics on business dinner etiquette, money, apartments, and much more!

We’ve sold over one million copies of life after school explained to 500+ colleges, 400+ companies, and 20+ greek organizations!

1,000,000 Penny Giveaway

To celebrate those million read world ready readers, we’re giving away 1,000,000 pennies:

  • We’re offering ten $1,000 grants to share our books with more graduates
  • We’ll have ten random drawings between Aug and Dec 2017.
  • Any organization is eligible (e.g. alumni office, school, company, etc).
  • The grant can only be used for life after school. explained. books ordered by Feb. 3, 2018.
  • An organization can only win once.
  • Details and winners will be posted on our Facebook page.


  • Step #1: Share the following text with at least 5 of your professional peers via email, listserv, or any social media:

Cap & Compass is giving away ten $1,000 grants before Dec. 15, 2017 for the purchase of their book “life after school. explained.” as part of their “One Million Real World Ready” celebration. http://bit.ly/2w5rTiI

We’re proud to help 1,000,000 graduates and look forward to helping even more in the 2017-2018 school year!

Product Design: What We Believe

We believe that design (broadly defined) is the key to any good product, so we felt that we should share our design beliefs with you.


Attention to detail
We obsess over fonts, shades of color, and the pixels in an icon. Details matter and get remembered by customers.

We remove stuff to create value. We explain health insurance in about 500 words.

Minimize friction
We minimize taps and headaches. If you don’t notice friction in our products, then we’re doing our jobs.

We don’t do everything. By focusing on just news, life 101 topics, and deals in our app, we have the time and attention to do these things well.

Mobile is unique
For our app, we design specifically for tiny, touchable screens used by real people with short attention spans.

No whiz-bang
We don’t add features which sound cool but get used just once.

We make products to be loved and shared. Our life 101 topics have soul.

Respect users
We ask ourselves, “Would we like this?” when building something. Our approach to advertising is respectful.


We have a responsibility to our customers and users to produce great products. If you believe what we believe, then you’ll love our book and app.

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Customer Love

At Cap & Compass, we aim to create great products and treat our customers as we’d like to be treated. We generally keep our heads down and let our customers handle the boasts.

But as a subscriber to many services myself, I often like to read what others have to say on a vendor’s website before I purchase. So here you go…


“We are very pleased with the book, and I think it will be the best gift we’ve ever given our graduating class.”

“THANK YOU, THANK YOU, THANK YOU. The books arrived and are a great success. Feedback has been wonderful.”

“Our book was a great hit! Could not have given a better ‘send-off’ graduation gift. Your entire operation – service, attention to detail, end product – were all outstanding.”

“We got our gorgeous books today! Everyone in our department ‘oohed and ahhed’ over them, I assure you!”

“WE LOVE THEM! THANKS so much for everything. You were so easy to work with – excellent in following up. You’ll be hearing from us in the future, no doubt!”


“Our alumni love the app! We’ve had several comments via social media channels indicating they find the tips useful and fun, and they appreciate the service.”

“Our program, dean, vice president, president, and marketing members love the app and what it has done for our students and alumni.”

“The dashboard for our app is an easy-to-use feature and the one-on-one contact with Cap & Compass has been extremely beneficial.”

“I’m so glad we decided to purchase your app.”

“I’m very pleased with the app. It’s extremely convenient using the dashboard to create polls, quizzes and feedback forms…”


“I do have to say, I’ve been very impressed with your company and the service we’ve received. Everything is always as it should be – or better.”

“I must tell you that I think you and your company are phenomenal! Your customer service and the speed at which you provide it are outstanding.”

“Your customer service has been wonderful and we have nothing but good things to say about the way business went with you.”

“Your company is truly exceptional! I appreciate great customer service and will definitely let others know how dependable you are.”

“I just wanted to take this time to thank you for your courtesy, professionalism, kindness and especially your patience. Your customer service is excellent.”

I hope you enjoyed them. Now back to the coal mines

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Celebrating Ten Years

Ten years ago, in the unfinished basement of our tiny Connecticut home, Jesse wrote the first edition of our flagship book, “life after school. explained.

What I remember most about that time are the late nights sitting next to each other in that damp New England basement – Jesse endlessly editing and trying out new jokes, making me laugh out loud while I was trying to write papers. It was our first year of marriage, my first year of graduate school, his first entrepreneurial venture.

The book was born out of a seminar series. In the beginning, schools would advertise free pizza to get their students to a taxes seminar. Jesse quickly learned that if you don’t make HMOs and 401(k)s funny, people will smile, take their pizza and leave.

The book has had its high moments: when a 22-year-old Marist College grad was elected mayor of his town and credited his early success to our book in his inaugural speech. And we didn’t even know the guy.

Photo from an article in the Hartford Courant, 12/6/05

And, of course, there have been low moments: like when the warehouse storing books caught fire. We learned that books are made of wood.

Over the years, we’ve loved watching our creative process spark the creativity in our customer schools – from amazing cover designs to cover photo shoots.

With over half a million copies sold, the book is very much still a living document. Over the years we’ve improved the customization options, revised pop culture references (Britney Spears out, Kim Kardashian in) and kept up with technology (Facebook didn’t exist, so neither did Facebook etiquette).

Most recently, we added chapters on Unemployment, Renters Insurance, and Travel Insurance. The book content is the foundation of our newest product – a mobile app called Crib Sheet.

A decade later, Jesse is still at his desk making edits to the book and I’ve joined him. We’ve traded in a damp New England basement for a humid Orlando office, and been joined by a local staff and a team working around the world to improve our products.

We hope you will give the updated book a read, and welcome your feedback.

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Our Team

I’m lucky to work with a talented group of people who love what they do. Let me do some introductions.

This is my crack sales team. They’re happy to answer your questions if you’re happy to take their cold calls.

Shelly, Jack, and Kyle

I use a talented team of designers/developers to help build “crib sheet,” our mobile app.

Billy, Mark, Michael, Justin, and Jordan

In case you’re wondering, they didn’t pose for this picture. They have such a sharp eye for design and symmetry that the spacing between their bodies is equidistant throughout the day.

Last, but certainly not least, I convinced my wife, Nicole, to do marketing work for me on a part-time basis in January 2010. Is it a coincidence that our blog started in January 2010?


I like to say that she had the longest job interview in the history of job interviews (almost fifteen years) and I’m lucky to borrow her brain.

And this is me:


I love my work, because it’s not a job. Plus, I have a view of a retention pond outside my window with lots of turtles.

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The Cap & Compass Story

Our first look at a hardcopy version of "life after school. explained." (2002)

Since Cap & Compass was founded in 2001, we’ve gratefully gained many loyal customers and readers due in large part to our humorous stories and life skills content. But we’ve never really had a forum to tell OUR story. So here goes…

The Early Days

After graduating from Duke in 1997 and a brief career on Wall Street, I came to realize that banking wasn’t my life’s calling. I needed to do my own thing.

I knew I wanted to start something with soul, something that could help people but also make a profit.

My early 20s were a study in mastering new situations on the fly – leaving college for life in “the city,” navigating the business culture of Wall Street, graduating from roommates to a wife.  My friends around me were going up the same, sometimes steep, learning curve.

I tossed around a number of ideas, but nothing stuck until the year 2000 when I asked my wife an innocent question over a slice of pizza during a boring airport layover.

“How about something about helping college grads, like Kaplan?” I asked.

My wife remembered a student group at Duke that tried to put on a ‘life 101’ seminar series, but they didn’t have the experience to pull it off.  She ticked off all of the life stuff she wished she’d learned at Duke (cars need oil), and I added my own (carpaccio isn’t pasta).

I can still remember scribbling notes on a sheet of paper over the next flight. And I actually kept the paper:

Notes from my flight (2000)

So I quit my potentially lucrative career in banking and told the in-laws, “Yes, I’ll support your daughter by giving funny seminars to college kids about 401(k)’s.”

I hired a stand-up comic/ex-school teacher, and together we began the long process of writing five seminars about “life after school.”

Seminar at Duke University (2001)

Presenting our material in front of a live audience of college seniors was a humbling experience. We had to be helpful, concise, and funny, or people would walk out with a smile and some free pizza.

But it was also the very best way to hone great content.

After a few months on the road, I turned the five 45-minute seminars into our popular book, “life after school. explained.

Present Day

I’ll talk more about the evolution of our products in a future blog post, but the sale of “life after school. explained.” really took off. We’ve sold over 500,000 copies to date. And we’re even more excited about the prospects of our new mobile app, “crib sheet.”

So that’s our story. I hope it’s helpful to give you a little bit of context of where we came from.

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Welcome to Our Blog

Hi. My name is Jesse Vickey and I’m the founder and president of Cap & Compass.

I like to tell people that I have three children: Elle (age 6), Beck (age 1), and my company. If you’ve ever started or run your own business, you understand.

Elle Working with Dad (2004)

I’ve never been one to post status updates or share much about myself online, but after ten years running Cap & Compass, I’ve decided to start a company blog. Here’s why.

#1. Learn About Us

Personally, I need to learn a little bit about a company before I open my wallet. I think you should too.

#2. Learn About Stuff

My team and I have worked with a lot of customers who are looking for creative ways to build loyalty with their alumni, members, or whomever. We’ve learned a lot and we’d like to share.

Thanks for reading.

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