Machine Learning and Neural Networks

If you ever wanted a good example of what machine learning is and how neural networks work, just check out this video.

Now imagine this same technique applied to a massive data set, processed with computing power by, for example, Google’s off-the-shelf Machine Learning Platform.  Leveraging these tools with unique data sets and specialized know-how will be the vector of differentiation for software companies over the medium term.

Risk (Loss Ratio) Management is Key to Long Term Success in Investing

There are no brave old people in finance. Because if you’re brave, you mostly get destroyed in your 30s and 40s. If you make it to your 50s and 60s and you’re still prospering, you have a very good sense of how to avoid problems and when to be conservative or aggressive with your investments.

This is such a good quote from Steve Schwarzman via Dan Primack.

Having just come through a massive risk-on investing period in Silicon Valley, an era where seemingly nothing but reward has been discussed (irrespective of investment entry point in a company’s life cycle) it is a nice reminder that reward AND risk management matters. Some risky bets might not fall you today, especially in private equity where feedback loops are long, but I can tell you from observing investment firms come, go, and stick around, over time, risk is a killer to a fund manager’s career and investors’ capital. (more…)

Mental Models and Technology Investing

As a lower risk operator in the technology investment markets, I operate well behind the venture capital frontlines, where hype and momentum reign supreme (because that’s just how that game works). Yet, it is still helpful to consider where the Seed-Stage and Early-Stage VC technology investment horizon is heading. What trends are real versus hype? Now that hype has worn off and the opportunists have moved on to the next buzz word, who is left doing real work? Which companies are emerging as winners from overfunded early-stage areas? What is realistically going to occur over the next 5-7 years with a winning company? What market segments are perhaps cheap due to investor biases? (AdTech?) Even though I might not make a move for years, pondering these questions is helpful to form a prepared mind.

HBR Transformative TechnologyConstantly questioning technology’s evolution is why I found the mental model shown at left from this HBR article interesting. This model highlights the differences in proliferation between foundational versus transformative technologies, comparing Blockchain today to TCP/IP (i.e. the Internet) in 1972.

While this model is helpful to compartmentalize things, the reality is that investing in technology is sloppy business. Sometimes it is hard to see where technology is heading, like driving in the fog. Other times, it’s obvious – less a matter of if, but when. Yet, even if a technology trend is obvious and the timing of its proliferation is roughly predictable, determining the winning company for investment is difficult, especially when squared with entry valuation and the number of “horses in the race” on a hyped technology trend. (more…)

Confusing Simplicity with Ease

Yesterday I had a nice conversation with a very thoughtful investor. He noted that while investing is pretty simple — buy low, sell high — people often confuse its simplicity for ease.

I love this notion. Because over the years, I have come to realize that investment success is predicated on some pretty basic principles: Hard work, thoughtful valuation discipline, strong underwriting and careful portfolio construction. As an investor, this enables you to find unique opportunities and buy investments to sell at a higher price, while ensuring that the distribution of profitable and unprofitable investments in a portfolio, on average, deliver a solid return. This sounds pretty easy, right?

After analyzing the strategies and results of countless public and private investment strategies over the past 16 years, I have come to realize that no matter your strategy or “angle”, making profitable investments, especially above-average investments, is not just hard, it’s extremely hard. The good news is that there are strategies which can make this challenge easier, namely specialization. Employing a narrowed focus, whether it be sector, stage or geography, can meaningfully stengthen the building blocks of investing (hard work, valuation, underwriting). Specialization enables you to work a niche, uncovering riches in the niches.

So, while the seductiveness of investing’s simple nature can make something hard seem easy, there are some basic things that can make a hard thing easier. And what is more fun than winning at something that is hard?

Starting a Company Feels Like You Are Unemployed

I have had numerous friends and family members negatively affected by the shakeout at Zenefits, so I was hesitant to write this post, but this quote from Parker Conrad, the founder of Zenefits, is a key one that I wanted to reflect upon.

“When you start a new company, it kinda feels like you’re unemployed,” Conrad told Axios shortly after his Demo Day presentation. A program like Y Combinator can motivate and bring structure to a founder’s work, he added.”

I couldn’t agree more about the unemployment bit. At the beginning, even with great co-founders, starting a company is a mental challenge and feels a lot like unemployment (save for all of the hard work you are doing). No paychecks. Sparse email traffic. No direction. Limited accountability. Total schedule flexibility. (more…)

Thoughts on the Snap IPO

Professionally I don’t get too excited about consumer technology IPOs, but I sometimes find myself entrapped, following certain consumer names for personal reasons. Snap is my current haunt. Snap has been a fun saga to follow and experience. I went from skeptic, to Snap user, to Facebook Stories user, and now back to being an avid Snap user (for good). I used to live in Venice Beach and skateboard past Snap’s first office before Snap was Snap; my old boss is now Snap’s #3 exec; and I constantly toil with wrapping my head around the sheer size of the opportunity around this company (it’s a big one).

For all of these reasons, I wanted to put my brief thoughts down on paper to hold myself accountable and to share some insights with readers. For full disclosure, I am not buying IPO stock, I don’t own any stock, and this is not investment advice (see disclaimer below). This is just my initial set of high-level thoughts to focus in on what I believe are the key issues. If you want vast reams of analysis, metrics, and fun with numbers, I would point you to Snap’s S-1Goodwater Capital’s review, RetailRoadshow, or here, here, and here. Lastly, apologies for the poor grammar below; I am in heavy GSD mode these days due to my two start-ups (family and company). (more…)

Michael Mauboussin on Maximizing the Probability of Investment Success

Sourcing, underwriting and constructing a portfolio of investments that produce attractive investor returns is tough and sloppy work. That is why I liked this quote from Michael Mauboussin on putting process around investing.

“We have no control over outcomes, but we can control the process. Of course, outcomes matter, but by focusing our attention on process, we maximize our chances of good outcomes.” — Michael J. Mauboussin

Being Different and Finding Your Career Groove

“It’s about the journey, not the destination.”

I love this quote and often use it to keep things in perspective, especially careers.

When reading professional biographies and interviewing job candidates, it often seems as if careers are a linear process. However, as I grow older, while it is true that some people enjoy careers that are truly linear, I am coming to appreciate that careers are more like a journey with a rough destination in mind. Individuals are constantly striving to reach their long term career goal, while having fun (however you define it) and picking up pieces of knowledge at each stop along the way to help them do so. (more…)

Life’s Lessons from Byron R. Wien, Vice Chairman, Multi-Asset Investing, Blackstone

I recently came across the below life tips from Byron R. Wien, Vice Chairman, Multi-Asset Investing, at Blackstone. Good reminders to keep life heading in the right direction!

1. Concentrate on finding a big idea that will make an impact on the people you want to influence. The Ten Surprises, which I started doing in 1986, has been a defining product. People all over the world are aware of it and identify me with it. What they seem to like about it is that I put myself at risk by going on record with these events which I believe are probable and hold myself accountable at year-end. If you want to be successful and live a long, stimulating life, keep yourself at risk intellectually all the time.

2. Network intensely. Luck plays a big role in life, and there is no better way to increase your luck than by knowing as many people as possible. Nurture your network by (more…)

I’m Back!

After 3+ years of hibernation due to the silence required by my technology investment banking role at Credit Suisse, I’m excited to be back to writing!

When I left off in 2012, my posts were getting increasingly long and complex, and as a result, more time consuming. I enjoyed long-form writing when I had a lot of free time. However, nowadays, I have less time for writing due to increased demands from work and a growing family. As a result, now that I’m back to writing, it may be more sporadic and it will certainly be more brief and less heavily edited. (more…)