Lessons from a Mountaintop, by the Godfather of Fintech


By Ron Suber – ReWirement is not an alternative to retirement, but a phase of global exploration that can happen at any age.

In the last 240 days, my ReWirement journey has enabled me to meet more people from around the world, including…

  • A 23 year old Nigerian student,
  • A 27 year old Chilean hiker,
  • A 31 year old Australian rafting guide,
  • A 35 year old Spanish waiter,
  • A 48 year old Indian engineer,
  • A 56 year old English philosopher,
  • Two bikers from Aspen in their 60’s
    …and many more.

All are pivoting in one way or another, finding out professionally and personally not only “what they want to be when” but also how to live their best life in balance.

What are they balancing?

  • The necessity of work
  • The need for power
  • The lack of control
  • The draw of fame
  • The desire for adulation
  • The insistence on being right
  • The search for money, love, fun, happiness
  • And the embrace of finding one’s higher purpose

On day 231-237

While hiking through a forest in Patagonia, wading over volcanic ash for miles, kayaking around fjords amongst glaciers and jumping off cliffs into roaring rapids I found the space to contemplate more on three of the most common topics of conversation.

  • FEAR

TOPIC 1 – Fear

Many along the journey have broached the topic of fear in their lives and often asked me to share my experience in overcoming it.

Few know that fear drove me to withdraw from the Prosper deal just days before we were going to invest with Sequoia in January of 2013.

The fear of failure, fear of change, fear of losing, fear of the unknown; all drove me to say no to the Prosper opportunity that I wanted and had worked so hard on with my business partners.

My courage came from a powerful email received along with some intense persuading. While I can’t repeat here the words in the prodding, I will share for the first time excerpts from the email received in early January 2013 from a very smart professional investor .

“After 40 years, we still have not found the perfect company nor struck the perfect deal. We have witnessed employees having fist fights in the CEO’s office, invested in some that had no revenue model….some that had no CEO. But every one of them did share something in common: a phenomenal market opportunity.

We have traded “deal points” for “market opportunity points”. When faced with a decision between optimizing for legal docs and optimizing for a market opportunity, we optimize for the market opportunity. If it’s there, the docs don’t have to be perfect.

Neither the perfect company, nor the perfect deal will present itself. We look for big markets in the process of fundamental change.”

I am more thankful than ever for that email and the timeless wisdom it contains. Overcoming that fear changed the trajectory of my life and helped shape my own investment philosophy (and the strategy of using an Investment Thesis).


Before investing in anything, I physically write up a thesis document on why I should or shouldn’t.

That’s why I did not invest in cryptocurrency years ago – I could not get my head, heart and wallet around it last year or the year before. When I go back and read the potential investment thesis docs that I wrote to myself, I just wasn’t there to pull the trigger.

What about you, what did your investment thesis say?

TOPIC 2 – Appearance

We all know that objects are often not what we see in the first impression and appearances deceive many.

I stared at the three towers of Torres Del Paine in Patagonia from many angles. The majority of time, the one in the middle looked tallest but the one on the left is actually 50 meters taller. Things aren’t always as they seem in nature, business, people and life. Keep staring, stay curious but remain open.

TOPIC 3 – Adapting

Adapting is the ability to adjust and modify one’s self to new conditions and new circumstances, and it’s a proficiency we should nurture as our surroundings change ever more rapidly.

Much of the world appears to be headed in different directions, with status quo’s eroding in some places while new norms are established in others. We see it in our economic climate, our social climate, our political climate, and even the climate itself.

While change is hard and often stressful, those who adapt, succeed. Nowhere is this more clear than in nature – as evidenced by these photos from hikes in Patagonia.

What I know for sure

Clear daily intentions are more important than ever.

Along with the good in life, we are all being bombarded with
an overwhelming amount of information, misinformation, and disappointing human behavior.

I hope that sharing these insights helps you overcome your fear, make adjustments, set your intentions, discover additional clarity, find more balance and actually jump off the cliff into the rapids of your best life.

P.S. Many along the ReWirement journey are also wondering if they are still young…below contains the answer:
“Count the number of dreams you have and compare them with the number of achievements you’ve had. If you have more dreams than achievements, then you are still young”
-Shimon Peres

P.P.S. Speaking of youth, I read the book “Aging Thoughtfully” recently. It offers perspectives about living thoughtfully, clarity on life cycles, emotions, legacies and much more. Hope you enjoy it as much as I did.

By Ron Suber, Originally posted on Rewirement.com