In hindsight, my first few years spent working at Goldman Sachs were some of the toughest but formative moments in my career and life.

Many people asked how and whether working at a Wall Street bank was necessary to start my businesses (JRINK, Apothékary) and each time I say, “hell yes“. It taught me three value-based personality traits: grit, determination, and heart-based decision making.

These three things also catapulted me later to quit my glossy job, leave the bright lights of New York City, move to Mozambique, and finally to DC where I ultimately found my true calling of being a creator.

While finance may not be as glamorized as “startups”, I owe so much to my former profession for providing me the confidence and backbone of how I make decisions in life, love and business.

  1. Risk is relative to price. The risk of loss, be it in investing or in life, is relative to the price or worth of a given decision. The higher the stakes, the higher the reward. Don’t be afraid to take smart bets like starting your own business if you know the full downside (e.g. $25k of initial capital, 2 years of time, etc.) and can hedge for it (e.g. adequate savings).
  2. Diversify your portfolio. With a plethora of choices available but limited resources, “asset allocation” is probably one of the most important considerations in life management. Don’t put all your eggs into one basket – set yourself up so when life throws a curveball at you, you aren’t completely wiped off your feet. It’s never a healthy scenario if you let one external variable be responsible for most of your returns or happiness. Don’t let any one thing be your everything.
  3. Timing can mean everything. It’s like going to Trader Joe’s on a Sunday at 5pm or meeting Romeo in a time of change. If you get in at the wrong time it’ll likely be an overcrowded or overly burdening experience and your exit, a stressful long one. Be opportunistic and
  4. Forget sunk costs. Things inevitably change but knowing what’s in versus out of our control is important. If something has fundamentally changed, the time or money spent previously should be rendered irrelevant. Limit your losses by moving on and making space for something better. When one door closes, another opens.
  5. Limit making decisions based on emotions. Psychological pressures make people make bad decisions and throw good money/time/effort after bad. Angry, scared, or under the influence, we often say or do many things we regret down the road so where possible, try to make decisions after a day of rest.
  6. No one likes desperation. In a tough environment when things aren’t going one’s way, the propensity to make emotional decisions is high. Effectively, standards get dropped and weaker terms are accepted. Know thy worth and remember the fiduciary duty you owe to yourself, above all else.
  7. Create a set of values to guide you. It’s in moments of immense pressure where we really see one’s character. Entrepreneurship is also glamorized but actually is a very lonely path. Knowing your guiding principles (I like to do this cardsort exercise every six months) and “your why’s” gives you a moral compass to guide you through turbulent and uncomfortable times.
  8. Have your own personal Board of Directors. Regardless of your strength as an individual, you are not immune to a constant surrounding of bad influence. Choose to be around humble, happy, and generous people that are exemplars of wisdom.
  9. Do your best, have fun and enjoy the ride. We’ll “win” some trades and we’ll “lose” some. What builds character is not avoiding mistakes – it’s how you choose to think and act afterwards. Success, to me, is a series of failures with no loss of enthusiasm along the way.

It’s this irrational yet predictable nature in all of us that create opportunities, establish common ground with others, and form a war chest of stories so fun to share and grow from.