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10 Financial Lessons for my 18 Year Old Self

Here are 10 financial lessons I’ve learned in the past 10 years that I wish I could tell my 18 year old self.

Start with the proper framework of accounts:

  1. Checking
  2. Investment (retirement)
  3. Long term savings (wedding, house, car)
  4. Short term savings (vacation)
  5. Guilt free spending (clothes, dining out, and gadgets)
  6. Emergency (three months of living expenses)
  7. Credit card (groceries, utilities, etc)
Automate your personal finance framework for investing, saving, and paying bills.

Automate your personal finance framework for investing, saving, and paying bills.


Set up automatic monthly investments, savings, and bill payments. “Paying yourself first” will help you achieve savings and investment goals and live within your means.

Avoid debt. It’s easy to start, hard to stop, and expensive to keep.

Start investing in index funds as early as possible. Hold them long term and let compound interest make you wealthy.  A dollar invested today is worth many more tomorrow. Forget mutual funds and GICs.

Don’t save mercilessly on the small things, only to spend carelessly on the big ones. Buying a house or a car is a huge purchase. Take your time, do your research, and don’t spend on needless options.

When you feel the need to buy something, put it out of your mind and wait three days.

Everything you buy has three costs: the cost of acquiring it, the cost of owning it, and the opportunity cost of not using the money for something else. Consider all of them before making a purchase.

Buy fewer things, and buy quality ones. Seek happiness in experiences, not possessions.

Money increases day-to-day happiness up to $75,000/year. Above that, life-satisfaction may increase but day-to-day happiness stays the same. Optimize for the most fulfilling work, not the highest paying.

Start a business. You’ll value money more after learning how challenging it can be to earn it outside of employment.

Three Realizations from a Having, Being, Doing Approach to Lifestyle Design

I often re-read The Four Hour Work Week by Tim Ferriss. It’s not a literary masterpiece, but I like that it challenges the conventional wisdom of “find a career, buy a big house, and retire.”

An exercise in the book has the reader create a Dreamline: a list of “Having”, “Being”, and “Doing” goals. I had a hard time assembling one at first. I searched online for “bucket list ideas” and found list after list of generic life goals. My mental breakthrough came when I bound the problem. I started asking specific questions like:

  • Where do I want to travel?
  • What do I want to learn?
  • What do I want to see in the world?

Using this approach, creating my lifetime Dreamline became easier:


Being in a relationship with things.

  • A condo
  • One performance car in my lifetime
  • A hand-made Japanese Go board


Having qualities, traits, or skills.

  • A better cook (take cooking classes)
  • Fluent in design (take self-directed design studies)


Things I would like to do and experiences I would like to have.

  • Start a tech company. Sell or IPO for $1B+
  • Invest in 25 companies to help others get their start.
  • Race the Nurburgring Nordschleife.
  • Drive an F1 car.
  • Attend the Monaco Grand Prix.
  • Go into space (Virgin Galactic or other).
  • Fly a fighter jet.
  • Race in a rally/targa.
  • Visit Japan (Tokyo, Kyoto, Fukuoka).
  • Visit Hong Kong.
  • Visit Singapore.
  • Tour Thailand (Bangkok, Chiang Mai, Phuket, Ko Phi Phi).
  • Visit Germany (Berlin, Munich).
  • Tour Italy (Florence, Venice, Rome).
  • Visit Spain (Barcelona, Madrid).
  • Visit London
  • Visit Paris.
  • Visit Vienna.
  • etc…

What started as a menial exercise turned into life changing event. It lead me to three important realizations that I’m lucky occurred early in my life:

1. Consider what you need to “have” to be happy. Many things that seem important in our daily lives (designer clothes, new technology, etc) don’t make the list. Others that do can be borrowed instead of bought.

2. Your “doing” list is likely 5x longer and 5x cheaper than your “having” list.

3. ROI on experiences is non-monetary, but critically important. As an analytical person, I found investing in experiences harder to justify than investing in assets. To come to terms with this, I developed a simple heuristic: Are the most interesting people I know the ones with the best experiences, or the biggest houses?

If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with success unexpected in common hours.

Henry David Thoreau

Improving my Environment with Ambiance App


This week I started using Ambiance App for Mac*.

Ambiance is an “environment enhancer” designed to help you create the perfect ambient atmosphere to relax, focus or reminisce.

If you walk into my office, you’ll likely hear a loop of Tea Garden Wind Chimes or the Gyuto Monks Tantric Choir. The library of 2500 ambient sounds has something for everyone.

* It’s actually an Adobe Air app. It’s SUPER buggy and is messing with my zen thing.

Vesting: Thinking Short vs Long Term

Conventional wisdom says that it’s in the company’s best interest to vest/defer the proceeds of an acquisition. It keeps the person incentivized to work on the company’s problems as the person unlocks their value over time.  The vesting schedule is usually 1-3 years, with payments being made monthly, quarterly, or sometimes annually.

Companies spend too much time worrying about locking you down for your vesting period and too little thinking what happens after that. We discussed it at length with Shopify, and at the end of the day, it was completely irrelevant. We’re here to work on challenging problems. Otherwise, we wouldn’t have done the deal in the first place.

Paying vested proceeds in a timely manner is in the best interest of any company. It allows the person to set down roots and invest in the city around them. Who is a bigger flight risk: someone who’s bought a house, started a family, and invested in local companies, or someone who is completely liquid and has no ties to the city?

Employees take up the mindset of the company. If the company thinks short term, the employee will too. If the company displays a long term vision, the employee will invest in it.

Be yourself and work as hard as you can to bring wonderful things into the world. Figure out how you want to contribute and do that, in your own way, on your own terms, as hard as you can, as much as you can, as long as you can.

John Lilly on Steve Jobs

Our Sophomore Year As Entrepreneurs

September 30th was Select Start’s second full year as a business.  Speaking for myself, Josh, and Tariq, it has been the most stressful but rewarding thing we’ve ever experienced.

In October of 2010, we had just convinced (duped?) our fifth employee to join the family.  Revenues were modest and runway was always an issue.  We occasionally got very creative with distributing founder salaries to make sure our team was looked after first.  We were finding our DNA as a company and our capabilities as individuals.

This year has been incredible.  It’s one that we’ll never forget, both personally and professionally.

  1. We’ve grown from five to 19 of the hungriest, smartest, and most talented people in the business.
  2. Our revenue is up 575%.
  3. Our profit is up a staggering 1025%.
  4. We’ve had the opportunity work with (unannounced) A-list companies.

To everyone who we’ve had stressed-out, candid, off-the-record conversations with: thank you for telling us to keep our heads down.

To our clients: thank you for trusting our engineers and designers like they were your own.

And to our engineers and designers: you are exceptional at what you do, and together you are unstoppable.

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Adam McNamara