In college, I joined a non-profit, Elmseed Enterprise Fund, a microfinance institute that lent $1,000-$3,000 to low-income entrepreneurs who didn’t have access to traditional credit. I thought it was a really interesting organization which had a mission I could get behind, having started my own little enterprises in high school with seed capital provided by my parents. From my time running Elmseed, I really saw how a little capital can change people’s lives — access to capital is such a critical problem in the world.

We funded an entrepreneur to start a hot dog cart who went on to spawn many more food carts around town. We funded a contractor who started to get big jobs from the university. In all these cases, we were able to make a significant individual impact, if not community impact, through capital.

Money has a multiplicative effect. When one individual can start a business (e.g. coffee cart), that person now has business needs (e.g. coffee beans from the local roaster). $1 can generate more than $1 of wealth in a community. 

One year, I came up with an idea to get more capital in the world of microfinance. We would go to big corporations and ask they temporarily donated money to a new fund which would buy up existing loans made by microfinance institutions to free up capital for those microfinance institutes to lend out again. The big idea was that we would only use that capital for 3 or 6 months before sending the money on to a charity that corporation already supported. So now Goldman Sachs could say it not only gave $1,000,000 to women’s education but it could say it gave $1,000,000 to microfinance and to women’s education (when it really was the same $1,000,000). Some of co-founders of the non-profit took the idea and started to get some major banks behind it. Unfortunately, I had to lessen my involvement over time as PaperG took off.

Recently, I’ve dipped my toe back into this world. I’m volunteering my fundraising and marketing knowledge to help out Acumen Fund, a wonderful funding model for social enterprises. It has pioneered the concept of “patient capital” — which is a financial investment with no expectation of turning a quick profit and focuses on maximum social impact over financial. It is funding some amazing social enterprises around the world and really investing in building a network of people trying to change the world. Expect to hear more about it from me in the months to come.

John Steinbeck on Falling in Love: A 1958 Letter

One painting that came alive for me on a recent trip to Paris was The Raft of the Medusa. It depicts some men on a raft after the first-time commander made a mistake during a voyage. It captures the moment in which salvation comes and rescue is in sight on the horizon.

For first time founders, this painting probably reflects some truth about that first major mistake or failing in their startups’ lives – whether it is a major customer loss, funding falling through, or press blow up. Right after that happens, you feel like it’s all over and you just want to find a way to survive.  Things may not only feel desperate but may become so, as people resort to drastic measures to keep the ship afloat.

I’ve come to realize that everyday can bring new hope. You just have to keep an eye out for opportunity and do everything you can to make it through the ordeal. If you can do that, you’ll be all the wiser and stronger for the next battle – whether it’s the next fundraise, customer deal, or startup. 

I started off on the bunny slopes the other week when we took the office out to skiing but by Day Two, I was doing real runs (albeit easier ones). I had a different teacher each day. I had never really skied before so it all truly was a learning experience for me. The whole experience made me wonder what separated a great teacher (or sensei if you will) from just an okay (or sufficient) teacher.

The ski instructor in the first day had to suffer through teaching the very basics to everyone in the class – young adult couples and housewives in their 40’s (and me). Early on, it was obvious there were huge gaps in the class in terms of natural ability or at least willingness to learn. He was clearly explaining how to do things but he couldn’t figure out new ways of explaining when the first ones failed to catch on for some of the students. The instructor had to teach towards the lowest common denominator and kept repeating drills long after some had mastered them due to the less astute students. As a result, the more advance students began to get bored and would do things on their own (I was on Youtube watching videos on how to ski). The instructor quickly lost control of the class. He’d only regain control once the lowest common denominator could do an exercise. Without a word, we’d move on to the next thing.

The ski instructor on the second day immediately tested everyone and separated them into different groups. From there, she would explain the theory behind things and the practical implementation. Then, we’d do it and get immediate critique and even were told what we could do better if we did the exercise as told since there is always room for improvement. She would give a lot of positive reinforcement as we were going through the exercise. By the end, she was taking us on runs that most people took days of learning before trying.

Comparing the two:

1. There’s a huge difference between knowing how to do something yourself and being able to explain it. You have to use different angles to explanations to ensure everyone can comprehend what they’re supposed to do.
2. You need to use positive reinforcement to make sure people feel like they are doing the right things.
3. You also need to challenge people to go for the next level rather than let them get comfortable with what they can do or should be able to do.
4. You cannot overestimate people’s attention spans and you got to keep them engaged.

That weekend is making me think about all the great and merely okay teachers I’ve ever had. What else separates them?

How economic-lotteries shape careers in certain industries and how they are becoming more common