4HWW Mentorship Contest Finalists

Ben and Reid wrote an in-depth post about risk and resilience for Tim Ferriss’s Four Hour Workweek blog. Over 500 people commented on the post, sharing their story of risk in their career. We selected the top three comments and reproduced them below. Please read their stories and then vote on who should win special mentorship, free books, and a free LinkedIn premium account. The link to vote is at the bottom of the page.


Samuel P.N. Cook: Iraq War vet giving up retirement benefits to find new passion

What do you do when your whole life is spent learning how to kill efficiently?

I am a Cavalry Officer in the United States Army, teaching history at West Point. And I recently realized that I am “caught” by the giant trap that is government service.

The U.S. Army has a retirement system which guarantees you half of your salary for the rest of your life once you have served 20 years. This is actually a legacy that dates all the way back to the days of Rome, where Soldiers of the Empire were given a farm after 20 years of service in the Legion.

The problem today (for the Army’s retirement system) is that most Soldiers end up living almost 40 years after they retire. And having 12 years of active service, going on 13, I realized that I was “trapped” by the security of this retirement system. Everyone I spoke to advised me that it would be crazy to give this up. Just gut it out, they say. Serve 7 more years.

My risk: I have made the “crazy” decision to leave the U.S. Army (and the retirement benefits). I have discovered website building and internet marketing as a passion, and have decided to build something in the fitness market.


Dennis Keohane: Teacher in a rut looking to use experience to pivot into new career

I have been teaching in a private school for 8 years now, eighth grade English, and I am good at my job, I find teaching boys about literature and life VERY rewarding, and, my career path is stable. The school I work at is full of teachers and administrators who have been here for between 20-40 years.

However, I am not happy. I am in full blown pivot mode. I know I need to make a change, yet I have the very heavy risk of change weighing me down at times. My pay is not very good, which I have been told is not going to change. I have a growing family: two kids under 3, a great wife who is also an educator, and a mortgage that is probably more than we should be paying. For the financial stability of my family, I cannot stay in the same job, and I cannot quit and risk the instability of joblessness.

However, I don’t have much experience outside of teaching. I do earn some nods and laughs when I have spoken to people in other fields and tell them that I have a great deal of experience in sales/marketing/product evangelism: I do it everyday, selling Shakespeare and having my customers come back wanting more.

I feel stuck. I feel constantly thwarted by my lack of experience and the feelings that sometimes rise that I do have a good job. But I know deep down that I don’t have the right job for me – at times my creativity and experimentation in the classroom have been penalized.

My risk: Potentially quit teaching and pivot into a more rewarding gig in tech, marketing, sales, and education in the Boston area — while supporting my family.


Cheryl Obermiller: Victim of embezzlement wants to protect small business owners

I am Cheryl Obermiller, former model and agency owner, mother of 8, grandmother of 13, host mom to 9 foreign exchange students, married for 27 years, certified scuba diver, overcame my fear of heights by climbing Mayan pyramids in Belize, run 3 miles every morning prior to doing a weight workout, and love to cook! In 1993 I founded my own heavy construction company, and by 2000 had turned it into a multi-million dollar business.

In 2010 I discovered that my long-time company accountant had, over the last eight years embezzled around a million dollars and almost bankrupted me. She reported to prison for a three year sentence in November 2011. The financial devastation was almost secondary to the emotional trauma – I cannot even describe the full impact of such a crime.

I am writing a book/program to teach small business owners how to protect themselves from financial fraud, which is called “My Accountant’s Drawers: the Small Business Owner’s Guide to Outwitting Embezzlers, Thieves and Scallywags.” Over the past couple of years, I have read thousands of fraud cases and been completely blown away by the very basic and simple-to-catch tactics used by over 90% of embezzlers. Most business owners don’t understand the risk of fraud in their own organizations; they are creative people who love promoting and expanding their businesses but hate paperwork. This makes them – us – easy targets for financial disaster.

My risk: Complete my book this summer and then travel around promoting it and speaking on financial fraud. This will require that I step away from my mostly-recovered, multimillion-dollar construction company and let three of our grown sons run it.


Thank you for reading the stories of the three finalists.


What will the winner receive?
We will personally invest in making the winner’s next career move successful, which includes the following:
  • Over email and in a 30-minute phone call, we’ll suggest relevant opportunities, key people to meet, and provide motivational support. The initial 30-minute call will be with Ben, and the follow-up emails will include Reid.
  • Two signed copies of The Start-Up of You
  • Their story will be highlighted in our LinkedIn Group.
  • Free Linkedin Premium subscription