Stephen Webb – Investment Analyst turned Internet Entrepreneur

Stephen Webb is the Director of Market Development at Portfolio Monkey, a San Francisco based startup that provides simple web based investment tools for the DIY investor.  Previously, Stephen worked as an analyst at Bristlecone Advisors, an investment and wealth management firm for high net worth clients.  He has also worked at the Russell Investment Group and Merrill Lynch.  He has an MBA from the University of Montana and a BA from the University of North Carolina-Chapel Hill.

When not working at Portfolio Monkey, you can most likely find Stephen on a near-by river fishing, thinking about fishing, or planning a fishing trip.  At the least, you’ll find him embellishing a story of previous fishing accomplishments to anyone who’ll listen.

What are you up to?

I’m focused on Portfolio Monkey and continuing to work on developing our investment applications and our marketing efforts.   This has been my first experience taking the startup plunge and the shift into this new world from a previous career in a corporate setting has surprisingly been one of the easiest transitions I’ve ever experienced.  It certainly helps to be working with a group of talented people and doing something you’re passionate about.

With everything that’s taken place in the financial markets over the past 9 months, we’re continuing to hear and read about significant changes taking place in how people manage their money.  Disintermediation is certainly one of the hot topics for discussion as a greater number of people look to take the reins themselves and conduct their trading online.  This bodes well for a company like ours that offers a complementary service to online trading.

Our goal is to provide DIY investors with easy-to-use tools that help them understand and manage their investment portfolios more effectively.   We try to simplify the process for the user while also providing education on concepts in conducting an analytical and intelligent approach to investing.

What are you into

Whenever time away from work is available, I’m into whatever recreation activities I can find.  Maintaining a sound work life balance has not always been easy for me to come by, but it’s been something I’ve been refocusing my energies towards.  For me, that usually encompasses some activity in the outdoors.  By setting aside time for extracurricular activities outside of the work place, I’ve found that my energy level and focus at work has increased dramatically.  I haven’t always been diligent about “letting work go” in the past, but ultimately found that to be a path towards high stress and burning out.  With some careful planning and a little bit of organization, I’ve found it’s actually pretty easy to get everything done during day that needs to, and I’ve still got time to bike, fish, or go for a hike in the afternoon or weekend.  I haven’t yet perfected the art of leaving the phone at home though and have been known to take work calls while standing in the middle of a trout stream.

How do you get stuff done?

Ultimately, my daily goal and overall method for getting stuff done is through a constant search for “flow.”  Flow is a feeling of energized focus and full involvement in whatever activity is being pursued at that particular moment.  It’s what’s defined by Mihaly Csikszentmihalyi in his book, Finding Flow, as “a state of effortless actions towards some project or task.”  It can apply to everything from skiing or closing a business deal.  It’s commonly what athletes refer to as “being in the zone.”  It’s not always an easy thing to attain, but the pursuit of it leads to a fuller and generally more rewarding day.

A few general things that I do each day to focus on being fully involved in the task at hand:

Defining a clear set of goals for the day.

I incorporate this by outlining the goals for each project that needs to be accomplished that day.  It’s much more detailed than just a simple to-do list.  I provide a lot of detail, sub-items etc. so that I have a very clear vision of what needs to be accomplished.  This allows me to stay more focused on the task during the day and evaluate what was and was not successful at the end of each day.

Eliminate surrounding distractions.

Some common examples are emails, twittering, or blogging.  Now, I’ll be the first to sing the praises for each of these wonderful forms of communication.   They are extremely useful tools for work, but I also find them to be a common source of distraction from other projects if not managed carefully.  Constantly bouncing back and forth between them and projects at hand is not being focused. I’ll admit that I’ve struggled with this in the past, but have become much more conscientious about it now and realize it can lead to inefficiency.  By setting aside certain times in the day to catch up on emails, twitter, blog etc., you can stay focused on each of your projects and move closer towards the elusive state of flow.

You mentioned that the transition from a corporate environment to the startup world has been easy, what’s made it so?

Although the overall product is different, the concepts now are very similar to what I’ve done previously in analyzing and advising investment strategies for Private Clients.  There’s always a great deal of quantitative analysis that goes on behind-the-scenes, but the client (or user) is usually only focused on the end result and how it translates into investment returns.

Previously, when I had client meetings, I would usually focus some portion of the discussion on educating or providing insight into the proper framework and approach for investing.   Similarly at Portfolio Monkey, a huge part of our focus is on providing a significant education component to the website.  The goal is to provide users with tools but also with information and a training ground to learn and perfect investing strategies.  This aspect of education also fits into the marketing wheel house in that we’re trying to continually bring our user base up the investment learning curve and make them more sophisticated with financial markets.

Talk a little bit more about the concept of “flow” and how it relates to both personal activities.

As I mentioned before, flow comes from being fully involved and focused on a particular activity to such a high degree that its pursuit becomes almost effortless.  In addition to the clear goals and zero distractions, the other necessary factors for flow include a pursuit that is both highly challenging but also requiring of skills the individual is highly proficient with.  When these factors are present, attention becomes ordered and fully invested and there is no room in the consciousness for distracting thoughts.

In his book, Csikszentmihalyi argues that it’s the full involvement in flow, not happiness, that makes for a more fulfilling and rewarding life.  While one can be happy for external factors such as a serene relationship, or a sunny day at the beach, happiness stemming from flow is of our own making and thus more fulfilling.

I often find flow when I’m fishing a river (often by myself) and am focused solely on reading the stream, studying what insects are hatching, and measuring just the right drift on my fly line.  At that particular moment, I’m fully immersed in one singular goal and have completely removed all other distractions.  For others, this activity might be singing in a choir, painting a picture, or playing golf.  Watching television doesn’t count.



Portfolio Monkey