A few weeks ago, my brother completed high school! His graduation was the culmination of a personal “no-sibling-left-behind” mission that I set to help my siblings attend college. My brother moved in with me “fresh-off-the-boat” right after I graduated from business school. I assumed guardianship of a teenager when most of my friends were setting … Continue reading Startups & Teenagers – The curious case of Benjamin Button

Recently, I was considering investing in a business whose brand I really like. The capital structure was unique because although young, the company had been funded through a very low-interest loan from an angel investor. Maturity for the loan was approaching in six months and the investor refused to extend the term. The company desperately … Continue reading Hurdle rates – If the bar is too low it might be a trap

Starting in 2004, I spent a few years tracking the promising story of Freddy Adu. Freddy, then a “14” year old phenomenon, and widely tipped to be the next big thing in soccer, became the youngest athlete ever to sign a professional soccer contract. He was drafted by D.C. United. United made a bet that … Continue reading Scalability – Just because it’s small doesn’t mean it will grow

Recently, I attended a conference on investing in food and nutrition companies at the University Club. One of the panelists dropped the statement above. It was catchy so I dwelt on it for a while on the train ride back home. I wanted to share my notes. Trade spend is a blanket term for all … Continue reading Trade spend effectiveness – It’s easy to get in through the back, but hard to get out through the front

Back in the day when analysts were still getting paid in investment banking, a friend decided to “invest” in a $80,000 Porsche. His reason was to “use this baby to woo and close on a wife asap then hopefully afford car payments on a dual income.” Those who know me well also know how I … Continue reading Operating leverage – Benefits are for closers, the rest get slaughtered

A few weeks ago, Instacart, the grocery delivery service provider, announced that 40% of its business had achieved profitability…at the unit economic level. According to the Bloomberg article, Instacart has raised $275mm in equity since its founding in 2012. This story is the perfect case study to conclude our unit economics discussion. Unit economics and … Continue reading Part 3: Unit economics – Because you gotta survive long enough to make the $

I received feedback from some of my readers that my latest post wasn’t easy to understand. So I spent the remainder of last week brainstorming ways to explain the concept better. The light switch moment occurred on Sunday while I was running the New York half marathon. I spent most of the race sketching out … Continue reading Part 2: Unit economics – Because you gotta survive long enough to make the $

Last week, I attended the Expo West trade show in Anaheim with colleagues. This event is a great American show of entrepreneurial aspiration and competitiveness. Entrepreneurs showcase their product and contend for opportunities with buyers, vendors and investors. What struck me was that unlike middle school, not all of these great companies take home a … Continue reading Unit economics – Because you gotta survive long enough to make the $

Outside of investing, I occasionally enjoy listening to hip hop music. A shared trait between the two trades is a maniacal focus on “the things that matter”. In hip hop it’s almost always cash and in investing it’s return on investment. Hip hop artists and investors alike casually drop catchy phrases to reinforce this philosophy. … Continue reading If it doesn’t make sense it doesn’t make $ – In support of spreadsheets

One afternoon, a long time ago, I was taking a stroll on Times Square and made a snap decision to buy a digital camera to bring as a gift to my parents on my next visit. I walked into one of the touristy electronic stores. The owner, some enthusiastic chap, thought it worthwhile to rehearse … Continue reading CDs and Sunglasses – Not all $ are created equal