Putting Family First in Financial Planning

A happy engaged couple in their 20s before they figure out how to integrate their finances… (July 2001)

Living a healthy financial life is far more difficult than most people believe. For most of us, our education in personal finance is relatively limited. We learn some from our parents and our friends, but for the most part, we are left to educate ourselves. This is not primarily an issue of intelligence, ambition, or capability. You can have an IQ over 140 and multiple degrees from incredible institutions and still not really understand the difference between a bank account and a brokerage account, what actions lead to a good credit score, or how to think about decisions like whether to rent or buy a house. 

This is one of the reasons why for the past six years I have invested the time and effort to create and teach a new course at Stanford University class, “Personal Finance for Engineers.” And after teaching the class to more than 1,000 students, it has given me quite a bit of perspective on how different people approach financial issues in their lives.

But as difficult as personal finance is for individuals, it is far simpler than the reality that most people face. 

Couples Are Not An Edge Case

The reason is simple: most of us are not alone. It turns out that ~62% of Americans between the ages of 25-54 are either married or cohabitating with a partner.

Financial planning is fundamentally different for couples. When my wife and I were married over 20 years ago, we received lots of marital advice, but very little guidance on how to merge our finances and plan our financial lives together. Over the past two decades, we have now seen a plethora of software applications and services developed to help people with a broad range of financial problems, and yet almost all of them are still designed primarily for individuals, not couples.

The financial lives of couples are becoming more complicated than ever. 80% of couples are now dual-career and dual-income. Making all of your accounts “joint” is no longer an effective solution, in fact, the most common way dual-income couples manage money is a through a “yours/mine/ours” method. 

Slide from Stanford CS 007 on Financial Planning for Couples, “Personal Finance for Engineers,” Session 8, 2022

Traditional financial advice has always been focused on families. Most financial planners insist on working with both partners in a relationship for the simple reason that their financial lives are intertwined. Their financial goals are planned together and both partners are required to make any financial plan successful. 

It’s not an accident that the highest tier of financial advisory firms refer to themselves as family offices.

Unfortunately, if you don’t have a liquid net worth of at least $1 million, it can be difficult or impossible to get a high quality financial advisor, and most couples do not have anywhere close to that amount when they are just starting their lives together.

This is why I am so excited to see Plenty launch today.

Plenty is building a home where families collaboratively manage their financial lives, beginning with the couple

The Next Wave of Fintech

The way forward will not be based on cloning the strategies that worked in the previous wave of fintech, but we can learn a lot from past technology transitions to see where fintech is headed. In particular, there are a lot of common attributes between how we navigated the transition between Web 1.0 and Web 2.0 after the internet bubble burst in 2000.

Three key trends will define the next wave of breakthrough products:

• Single Player → Multiplayer
• Millennial focus → Multigenerational
• Replicated products → Novel products & services

At Daffy, we have built our platform around these three ideas. Last fall, we became the first major donor-advised fund to offer native support for families (up to 24 people!)

With the launch of Plenty today, we will now see what a modern platform for financial planning could look like when it is designed to be multiplayer from day one. 

Congrats to team at Plenty on their launch, and proud to be an early investor. 🎉

Daffy: From Acorns to LinkedIn

This blog post was also published on Daffy.org

Steve Jobs famously talked about connecting the dots of your life in his now well-known commencement speech in 2005. There’s something incredibly insightful and at the same time humbling about that framing as a founder when you look at the differences between the product you set out to build, and where the journey takes you once you launch.

Daffy was based on a number of fairly simple, but powerful, inspirations:

• The idea that we teach our children to put money aside for charity, but that as adults we rarely follow that lesson.
• The idea that donor-advised funds are a great financial product, but are largely unknown to most people because the incumbents cater almost exclusively to the wealthy.
• The idea that the same behavioral finance insights that led us to build better systems to help people to save and invest could also be used to help people give.
• The idea that a simple app, like Acorns, could over ten years help a customer base of almost five million paying users with their financial health.

When Alejandro & I raised our $4.8M seed round in 2020 to help build what is now known as Daffy, the Donor-Advised Fund for You™, it was very much based on the idea that we would build the Acorns for Charity. That’s what we pitched.

A little over one year ago, on September 30, 2021, we launched the service. Launching a new product is always both a triumphant and humbling process. It’s so powerful to see people using and enjoying something new that you and your team brought into the world. At the same time, the initial launch is almost always the beginning of the learning process, because real customers have a way of showing you the truth about where they see value in your creation.

So, not surprisingly, it quickly became obvious that we had missed something fundamental in our initial concept of the product.

Giving is not like saving on one very important dimension. Unlike saving, giving is fundamentally better with other people. We discover new causes and charities through other people. We are inspired to give by other people. Most importantly, we support the causes and charities we care deeply about with other people.

The more we learn from our members, the more we’ve come to realize that Daffy is meant to be more than just the best donor-advised fund on the market.

We set out to build the Acorns of Charity, but the future of Daffy may look much more like LinkedIn.

Giving is Better Together

The best software product clues tend to come from the organic actions of customers, and this has definitely been true with Daffy. In this case, our first clue came from people sharing their inspiration around giving with others. 

Every DAF allows their members to include a note to the charity with their donation, and when we designed Daffy, we included this feature. However, with every Daffy donation, the member is given the option to add a public note about why they give. For an optional feature, we weren’t expecting heavy adoption, but in our first year, over 36% of our donations had a public note.

These notes are not like typical internet posts. In many cases, they reflect emotional and deeply personal motivations for supporting causes and organizations.

It might be hard to believe, but in the early days of LinkedIn, there was a lot of public debate about what identity online would look like. Would people have a single profile that represented them on the web, or would we have multiple, reflecting the different slices of our lives? Mark Zuckerberg argued for the former, while Reid Hoffman argued for the latter.

What we believe we have discovered at Daffy is that there is another identity that is meaningful to people, and yet does not seem to have a home online: our charitable identity.

Our Charitable Identity

Even at LinkedIn, it was clear that there were going to be more than just social and professional profiles. Our identities and relationships are often compartmentalized based on context: think about what you ask someone you just meet at a party vs. a conference vs. a school event. At a little league game, I’m not even sure that I have a name — I’m just Julia’s Dad! These identities flourish and wane over the course of our lives, sometimes merging, sometimes fading.

Over the past few decades, it has become clear that there is a resurgence in how people think about themselves philanthropically. The causes you believe in, the organizations you support, the people you work with to make a difference — all of these matter increasingly to people. Perhaps it is a reflection of the times we live in, or perhaps it is an aspect of maturing generations. Whatever the cause, however, it is clear that people are eager to share this part of themselves with friends and colleagues, and also seek this information about others. We are proud of the roles and responsibilities we take on with charitable organizations and the people who work for these organizations.

Discovery. Inspiration. Support.

These seem to be some of the major emotional drivers behind the activity we see from our early Daffy members, and yet this seems to get lost on existing platforms. It’s so hard to compete with dating, news, shopping, and careers.

Fulfilling Our Series A Vision

2022 has not been a kind year for technology companies in general and has definitely been a tough fundraising environment for venture-backed startups. However, when Alejandro & I realized what we needed to do, we also knew we needed to raise our Series A sooner rather than later.

We know that building out this platform will take years, and we are grateful to Ribbit Capital and XYZ Ventures for supporting this vision, and we are especially grateful to the dozens of leaders and luminaries who have individually invested in our efforts.

Today, on Giving Tuesday, we are starting to roll out our first features that will help bring this vision to life. A place where people can not only share the causes and charities they personally support, but also spotlight a charity they are working to support right now. A way to learn who our friends and colleagues give to, and the opportunity to be inspired by their generosity and support their efforts. 

All of these features are layered over our ground-breaking, modern donor-advised fund platform, built from the ground up to help people be more generous by setting their own personal giving goals and then helping them achieve them.

All throughout November, our #BeMoreGenerous campaign gathered 30 notable leaders including Reid Hoffman (co-founder of LinkedIn), Charles Best (Founder of DonorsChoose), and Amy Chang (Board of Directors at the Walt Disney Co.) to use our new “Charity Spotlight” feature to share the charities they support this holiday season — and inspire others to give.

As of today, that feature is now available to every Daffy member.

Together, we believe that we can increase giving by over $1.2 Trillion dollars over the next decade in the United States alone, with an even larger opportunity globally.

If you are one of the 60-70 million households in the United States who give to charity every year, go to daffy.org now and set up an account. It’s completely free for members just starting out with a balance of under $100.

Connect with your trusted friends and colleagues. Share the causes and organizations you believe in. Inspire others to give, and more importantly, connect more people to organizations that desperately need more support. Include your family, and foster real discussions about the causes and organizations you support.

Daffy launched just a little over a year ago, and we are grateful to the thousands of people who have already signed up for the service. But our aspirations are audacious.

Our vision is a world where everyone puts something aside regularly for those less fortunate than themselves. A community of millions, not thousands.

Come join us.

Build The Future You Want To See

One of the reasons that I am so passionate about entrepreneurship is because of my belief that companies can be highly effective agents of change.

This isn’t just a feature of technology companies built in Silicon Valley. Vanguard is an inspiring example, headquartered in Malvern, PA. They are immensely successful — now responsible for over $8 trillion in assets, and yet their impact is far broader than assets alone might suggest. Vanguard makes just a fraction of the revenue ($6.9B) of Fidelity Investments ($24B), but this is because Vanguard focuses more on making money for their customers rather than themselves. And while Vanguard has millions of happy customers, there are tens of millions of investors who are not customers of Vanguard who pay lower fees and have more money in retirement because Vanguard exists. They have forced an entire industry to offer higher quality financial products at lower prices.

Two years ago, Alejandro & I set out to build a category-defining company in a space that has been ignored for far too long. Each step of the way, I shared pieces of our story:

• My original intention to start a company
• Our initial seed round funding
• Our audacious goal to help unlock an additional $1.2 trillion for charity
• The future of fintech (2025)

Today’s release of Daffy for Families is a major milestone in our journey to fulfill that vision.

The Next Generation of Fintech

2022 has been a very difficult year for the economy, and it has been particularly hard on the venture-based startup ecosystem. We feel very fortunate to have raised our $17.1M Series A in February, giving us ample time to invest in our platform.

The way forward will not be based on cloning the strategies that worked in the previous wave of fintech, but we can learn a lot from past technology transitions to see where fintech is headed. In particular, there are a lot of common attributes between how we navigated the transition between Web 1.0 and Web 2.0 after the internet bubble burst in 2000.

Three key trends will define the next wave of breakthrough products:

1. Single Player → Multiplayer
2. Millennial focus → Multigenerational
3. Replicated products → Novel products & services

Daffy for Families is the first feature that we’ve shipped that illustrates all three.

Giving Together is Better Than Giving Alone

Unlike most financial products and services, giving is fundamentally better when done with others. We learn from each other, we challenge each other, and we inspire each other.

But why does every donor-advised fund have to look like a retirement account?

Why can’t grandparents engage with their children and grandchildren around the causes and organizations they support? Why can’t children learn from their parents about how and why they give?

Alejandro & I are both parents, and as a parent, you learn a few hard-earned lessons. One of those lessons is the simple fact that actions speak louder than words. It’s one thing to tell your children that reading is important, but it’s a very different thing for your children to see you read.

The move from Web 1.0 to Web 2.0 was based on fundamental insights like these, and it’s the reason why LinkedIn does not look like Monster.com.

Over the past decade, I have been floored by how many intelligent and passionate people work to support charitable organizations, and yet it has become increasingly clear that they are frustrated. Frustrated by the slow pace of technology. Frustrated by the inability to help people give. Frustrated by an industry driven by a business model that focuses too much on dollars and not enough on people.

They are looking for something new — an agent of change, a new platform, a new model that can unlock the way people connect with the causes and organizations they support.

We think Daffy could be that platform.

Leadership Through Product

With Daffy for Families, we are asking the industry a simple question: Why don’t you let families give together?

Almost every major consumer platform has family sharing, and yet Fidelity, Schwab, and yes, even Vanguard haven’t invested in this basic capability.

Why?

My best guess is that their business model, which is based on charging a fee based on a percentage of assets, makes features like this look expensive. After all, having more people on a fund to help inspire each other to give will likely lead to more money going to charity and less money sitting in funds earning fee revenue.

Daffy was built to be different. We have a simple mission: help people be more generous, more often. We are also quite proud to have a business model that rewards having more people involved with giving rather than more dollars sitting in accounts.

It has been just one year since we launched Daffy, and yet already we are already shipping features that may take the industry years to copy.

We can’t do it alone. Every member who joins our platform helps force the industry to change. Together, we believe that we can unlock the generosity of millions, and in the process, free up trillions of dollars for worthy causes and organizations.

Check out Daffy for Families. Set up a fund. Invite your loved ones.

Join us. 💗

Figma: A Random Walk in Palo Alto

Figma’s first conference, Config 2020.

On June 25, 2013, Dylan Field, one of my favorite interns from LinkedIn dropped by Wealthfront headquarters in Palo Alto to catch up and get some advice about his new startup, Figma.

At the time, I was up to ears with work as the new CEO, trying to sell the crazy idea that someday millions of people would let computers, rather than humans, manage their money.

But I always take time for people, particularly students just coming out of college and embarking on a career in Silicon Valley. So I met with Dylan for an hour, and we walked around the City Center in Palo Alto talking about his new company. The next day, I sent him a note asking if there was any more room in his seed round, offering to help him with product, growth, and recruiting.

Yesterday, that company (Figma) was acquired by Adobe for $20 Billion.

From Intern to Founder

In 2010, Dylan was an intern at LinkedIn, on the data science team overseen by my friend DJ Patil. However, search & data science were closely intertwined at LinkedIn, and since search was an area that I was responsible for, I spent a lot of time with team brainstorming new ideas and working through product problems. For some reason, I distinctly remember that Dylan was the first intern to ever make me feel old, based on one offhand comment about how he was too young to see the Star Wars prequels when they came out. 🤦‍♂️

Regardless, Dylan was brilliant and delight to talk to about almost any topic, and we kept in touch loosely through social media when he went back to school. He ended up interning at Flipboard, a company that happened to be founded by an engineer from Apple who co-taught CS 196P at Stanford with me, their first class on iPhone development. Dylan stayed close to the data science team at LinkedIn, and so we ended up with more than a few reasons to stay connected. I had left LinkedIn to take an EIR role at Greylock, so was just starting to become an active angel investor.

All of this led to that one walk around Palo Alto.

The Figma Pitch

There was no deck involved, and the meeting was not about fund raising. As it turned out, Dylan had already largely raised his seed round. In fact, a TechCrunch article came out about it that day. Going into the meeting, I had absolutely no idea what Dylan was working on, and knowing Dylan, it literally could have been anything and it wouldn’t have surprised me.

Instead, Dylan & I talked about the transition from Desktop to Web 2.0, and whether now was the right time to bring graphic design to the cloud. John Lilly & I had discussed a hypothesis about this while I was at Greylock, and it was one where I had come to have conviction. The basic premise was that the combination of Web 2.0, Social, and Mobile had finally created the possibility of building truly useful and user-friendly collaborative software in the cloud that was an order of magnitude better than desktop software and would finally drive the migration of professionals to web applications. More importantly, we believed that the history of desktop software contained clues to which types of software would be converted first: productivity applications (late 70s/early 80s), then enterprise applications, graphic design & desktop publishing, and finally personal finance. In fact, this theory is part of the reason I spent 2012 exploring the idea of bringing financial software to the cloud, eventually leading me to the sector now called “fintech” and my role at Wealthfront.

As we talked about this theory, Dylan then shared with me one of those simple insights that seems so obvious in hindsight, but was anything but obvious at the time. He told me that with WebGL in the browser, he thought now was the time to move graphic design to the cloud. As someone who had spent significant time in grad school on computer graphics, my initial reaction was very negative. In my mind, graphic design was incredibly compute intensive, to the point where professionals used highly optimized $10K workstations, multiple GPUs, and optimized data storage to get the local performance they desired.

Dylan was not deterred. He explained that the heavy compute was the exact reason why moving to the cloud made sense. By providing high powered machines in the cloud, anyone could get access to an almost arbitrary amount of power without spending $10K, and latency & bandwidth had progressed to the point where shipping the UI bits to the client was a solved problem.

He was right.

It was a simple moment, but I had to admit that multiplayer gaming had already solved problems of low latency, collaborative UI, and that it might be possible to extend that to the web now. Graphic design wasn’t just going to move to the web – eventually it was going to be better, faster, and cheaper online. On top of that, collaboration would be the killer feature that desktop couldn’t match.

The initial product idea, a photo editor in the cloud, turned out to not be the right way to ride this wave. But in the end, Dylan & team were intelligent and flexible enough to clearly iterate to a product that not only is riding that wave, but is also defining it.

Silicon Valley is about People

When I graduated from business school, my first job was as an Associate at a venture capital firm in Menlo Park. 2001 was a rough time to start in venture capital, but I was excited because I loved the idea of investing capital with founders when everyone else had pulled back. Our office, however, was too large, built out for a boom that had been cut short in 2000. As a result, they gave me a choice of offices.

I picked the one no one wanted, adjacent to the reception area. People thought it was too noisy, but I always left the door open. The reason was quite simple: when founders came in, I wanted to overhear how they treated our receptionist. You can learn a lot about a person based on how they treat people with less power when no one else is around.

Success in Silicon Valley is a dizzying combination of skill and luck, execution, and timing. But first and foremost, it is about people. One of the reasons that the most successful software cultures struggle to avoid hierarchy, is that the rapid change in platform capabilities means that the half-life of experience is brutal. The best solution for a problem five years ago may not be the the best solution today, and it very likely won’t be the best solution five years from now. As a result, young engineers approaching problems for the first time can sometimes see opportunities that the most experienced can’t. Other times, a “new” problem can actually just be a rehash of a problem that was common decades ago. The key is always to work the problem, and always work to avoid the destructive HiPPO anti-pattern. (HiPPO = the highest paid person’s opinion)

These days, online discussion is filled with debates about impressing your boss, impressing your CEO, impressing the company. To me, this misses the real opportunity. For most people, their best opportunities are likely ahead of them, and the connection to that opportunity will mostly come from a co-worker, a “weak connection,” and likely someone who isn’t above you in power and hierarchy.

Dylan was an intern, and not even an intern on my team. There was no obvious reason for me to spend time with him, other than that he is an amazing human being. Very intelligent, and also very kind. A long term, first principles thinker, but also someone who gets his hands dirty building. Ambitious, not to be a billionaire, but ambitious to make a difference and have an impact.

As an angel investor, I tend to look for a strong, authentic connection between a founder and the product they are building. For me to invest, I have to believe the founder is not only tackling a problem big enough to generate venture returns, but also is someone who is intelligent, trustworthy, and ambitious.

Dylan might have been an intern, but even as a teenager, he was all three.

A True Silicon Valley Story

Our careers are built based on the overlay of networks that we build. Every school, every job, every company is an opportunity to connect with people. It will only be obvious with hindsight which connections will generate the most value in your career, but try to remember that everyone may have something you can learn from.

There were quite a few executives at LinkedIn, and more than a few interns. There was no way to predict this type of outcome. Nine years ago, I became an investor in Figma, and two years ago Dylan became an investor in my new startup, Daffy. Roles change fairly quickly, but relationships with good people last decades.

Congratulations to Dylan, Evan, and the whole Figma team. This acquisition is just one more step in the fulfillment of a broad vision to elevate design in every organization. 🎉

It’s a true Silicon Valley story, and one we should all be rooting for.

A Goal for Giving

Like many people, for most of my career, I never set an explicit goal for giving to charity. While I was raised to believe that everyone should put something aside for those less fortunate than themselves, in practice, I mostly gave only when I was asked. Sometimes it was a friend running a marathon for a worthy cause they had a deep connection to. Other times it was a fundraiser for one of the schools that my children attended. But overall, it was reactive, not proactive.

This all changed for me in 2011.

I first learned about donor-advised funds when LinkedIn went public in 2011. All of a sudden, private wealth managers became ubiquitous on campus. Part their sales process, as it turns out, was to promote the tax-deductible benefits of giving to charity through donor-advised funds.

The concept of a donor-advised fund appealed to me, but it raised an important question: how much should you contribute to a donor-advised fund? I had no idea.

Fortunately, at the time, my accountant recommended a fairly simple approach: take whatever amount you plan to give to charity every year, multiply it by ten, and contribute that to a donor-advised fund. The best part? By investing the money upfront in a donor-advised fund, I could potentially fund years eleven or twelve with the proceeds.

For the first time, I was forced to answer what should have been a very simple question: how much did I want to give to charity every year?

At the time, I chose $20,000, which was 10% of my base salary at LinkedIn.

More importantly, I now had a giving goal. And it changed everything about the way I give.

The Two Hard Problems With Giving

It turns out that there are two hard problems inherent in giving money to charity:

1. How much can you afford to give?
2. Who should you give the money to?

Until I had a donor-advised fund, I never realized how much the first problem influenced my generosity. But every time I was asked for a donation, there was friction as I tried to figure out what I could afford. However, once I had a giving goal, the first problem largely went away. As a result, I found it easier to give when I found an organization or cause that I believed in.

More importantly, the goal made me more generous. While the donor-advised fund did not change the amount that I thought I should give to charity, it did change the amount that I actually gave to charity. Looking back at my records before 2011, it is clear that having a goal increased my actual giving by more than 100%.

This shouldn’t be surprising. Behavioral economists have known for a long time that pre-commitment can dramatically increase the amount that people save for retirement. Why couldn’t it also work for giving?

This is the reason Alejandro & I started Daffy.

Set Your Giving Goal Today

Our research shows that when asked, most people intend to give a larger amount to charity than they actually end up giving in practice. At Daffy, we call this difference the Generosity Gap. It may sound like a small thing, but we believe that if everyone set a giving goal, it could increase the money given to charity by more than one trillion dollars over the next ten years.

Every year, we set goals for ourselves. Financial goals. Fitness goals. Diet goals.

Until 2011, I didn’t know what a donor-advised fund was, and I didn’t have a giving goal. But in 2022, you can sign up for Daffy in minutes, set a giving goal for the year, and have an app at your fingertips anytime you find the desire to give.

This year, consider setting a goal for your giving and be the generous person that you want to be.

Join us.

It’s Time to Build… in Public

In 2020, I set off to build a new company. At the time, I never would have imagined that we’d end up building one during the largest pandemic in a century.

Lao Tzu said that a journey of a thousand miles begins with a single step, and I count myself fortunate to have made the best first step possible in finding a truly world-class co-founder. Alejandro is one of those rare talents that makes Silicon Valley special, a true builder and an inspiration. Together we set off on a journey to turn an audacious mission and vision into a reality.

We have been very fortunate. Despite building this company during the COVID-19 pandemic, we have been joined by an incredibly talented team. Each member of our founding team has taken a leap of faith that together we’ll be able to build something out of nothing. So many investors have also been willing to take that leap with us and fund our early efforts.

Today is the day. Not an ending, but a beginning. We’re coming out of stealth, and we’re ready to start building in public. It’s hard to explain how exciting and terrifying this moment is.

Introducing Daffy

Daffy is a community and platform built around people willing to make a simple commitment to regularly put money aside for those less fortunate than themselves. At its heart beats a fintech core: a new modern donor-advised fund built from the ground up for this purpose.

Daffy is the Donor Advised Fund for You™.

Unlike most financial products, giving is inherently social, and we see immense opportunity to bring people together around the causes and organizations that they support.

You can read more about Daffy here, learn more about our team here, and get a quick walkthrough of the product here.

Who Taught You To Be Good?

Alejandro & I are big believers in talking to customers, and so we spent a lot of time talking to people about how they think about giving to charity. Through the course of that research, we came to two important insights:

1. Moral Compass. Almost everyone has a person in their life — a parent, a relative, a teacher, a priest — who instilled in them a strong sense of what it means to be a good person. Some people even say that they can still hear that person’s voice when they decide to do the right thing. Invariably, that person taught them the importance of giving to those less fortunate than themselves.
   
2. Guilt. Almost everyone has an idea of what they believe they should be giving to charity every year. Interestingly, there is very little agreement on what that amount is, but for almost every person we spoke to, there is a number. Unfortunately, very few people live up to that ideal. Our lives are too busy, and giving often falls off people’s immediate to-do lists. The can gets kicked down the road. As a result, people are not able to be the type of person they want to be. The person that their moral compass would be proud of.

Technology Can Help

We believe that technology has a role to play in solving this problem. Why can’t we use the same techniques that we have used to help people shop and save to help people give?

By automating giving, we believe that technology can help people be more generous, more often. We can help people be the good people that they want to be.

In some ways, it is not surprising that a company born during the pandemic would focus its efforts on one of the biggest problems caused by the pandemic. There are millions of people struggling, and we believe that there are millions of people who want to do something to help. We believe that there are millions of people who want to take action, who want to support the causes and organizations that will help build a better world.

We believe that there are millions of people who are willing to make a commitment to give.

Come join us.

Silicon Valley Home Prices, Stock Prices & Bitcoin (2021)

A little less than four years ago, I wrote a post about home prices in Silicon Valley and how they relate to stock prices and Bitcoin. It was one of the most popular posts on my blog from 2017.

The original compared housing prices in Palo Alto to a few of the largest technology companies in Silicon Valley, with Bitcoin added just for fun. Given the incredible rise in technology stock prices and Bitcoin in the past few years, it seemed worthwhile to update the data in the original post.

Talking about home prices in Silicon Valley is always a sensitive topic, because the lack of affordable housing continues to be a both difficult and heavily political topic. As someone who grew up here, it seems painfully obvious that the primary problem is the overwhelming resistance of local city councils to approve housing unit construction that meets ever increasing demand.

This post isn’t about that issue.

Instead, this is an attempt to look at the housing market through another lens. Most financial estimates of housing cost tend to compare the price of housing to incomes, which makes sense since for most people in most places, the affordability of a home is directly related to the size of the mortgage that they can obtain for that home. In general, houses are purchased based on income, not assets.

In Silicon Valley, of course, income looks a bit different since many people in Silicon Valley work for technology companies, and most technology companies compensate their employees with equity.

Palo Alto Home Prices

I chose Palo Alto as a proxy for Silicon Valley home prices because it is historically “ground zero” for Silicon Valley tech companies, and it has relatively close proximity to all of the massive tech giants (Apple, Google, Facebook).

The original post started the data sets in June 2012, since this was roughly when Facebook became a public company. For this post, I’ve extended the data sets all the way to March 2021.

All housing prices have been sourced from Zillow. All stock prices have been sourced from Yahoo Finance, and reflect the price adjusted for dividends. All Bitcoin prices have been sourced from Investing.com.

This is what Zillow looks like today for Palo Alto:

As you can see, in June 2012, the average Palo Alto home cost $1.44M. Roughly five years later, in June 2017, that average price was up 84.6% to $2.55M. Now, in March 2021, that price has risen a total of 117.9% to $3.15M.

That’s certainly a much faster increase than any normal measure of inflation, whether looking at changes in prices or wages. But what happens if we look at those increases in comparison to the stocks of some of the largest technology employers in Silicon Valley?

Apple ($AAPL)

Apple is the most valuable public company in the world right now, measured by market capitalization ($2.023 Trillion as of March 18, 2021), and second most profitable ($55.256B in 2020). Thanks to their exceptional financial performance, Apple stock ($AAPL) has increased significantly since June 2012, rising (split-adjusted) from $18.79 per share to $124.76 in March 2021. That’s a gain of over 565.8%.

Wow. 😳

Let’s look at Palo Alto home prices as measured in dollars, and then let’s look at them in comparison priced in shares of $AAPL.

This chart tells a very different story than the one from 2017.

In the five years from June 2012 to June 2017, Apple stock was volatile, but over the entire time period almost exactly matched the growth in Palo Alto home prices. However, the run up since 2017 has been incredible.

Split-adjusted, it took 76,839 shares of $AAPL to purchase the average home in Palo Alto. By March of 2021, that number had dropped to only 25,216 shares.

This isn’t surprising, since Palo Alto home prices are only up 117.9% over that time period, and Apple shares are up 564%. But what this means from a practical viewpoint is that for people converting one asset (Apple stock) into another (Palo Alto housing), it has become easier, not harder, to purchase the average home.

Google ($GOOGL)

Google tells a similar story to Apple in 2021, even though that wasn’t the case in the original post. Since 2017, Apple stock has clearly outperformed Google, leaving them with almost identical price increases from June 2012. (By itself, that’s somewhat of an amazing fact given the relative ages of the two companies).

As of March 2021, Google has a market capitalization of $1.37 Trillion, significant less than Apple’s. However, they have seen price appreciation of 557.3% since June 2012, rising from a split-adjusted $316.80 per share to an amazing $2,082.22 per share in March 2021.

Let’s look at Palo Alto home prices as measured in dollars, and then let’s look at them in comparison priced in shares of $GOOGL.

If you compare this chart to the one for Apple, it tells a different story but has a similar ending. Google shares are clearly more volatile than Palo Alto housing, but they have fairly consistently appreciated over the past decade.

In June of 2012, it would have taken 4,557 shares of Google stock to purchase the average home in Palo Alto. By March 2021, that number had dropped to only 1,511 shares.

So while Palo Alto home price appreciation has been tremendous by any historical measure, Palo Alto housing has become cheaper in the past decade for people holding Google stock, and more expensive for people holding dollars.

Facebook ($FB)

Facebook, the youngest of the massive tech giants, already has one of the largest market capitalizations in the world. As of today, Facebook is valued at $793.4 Billion. Facebook stock has risen an incredible 1208.2% since June of 2012, from a price of $21.71 per share to a price of $284.01 in March 2021.

At this point, you know how this story goes. With growth of over 1200%, Facebook stock goes a lot further in 2021 than it did in 2012, even against daunting Palo Alto housing prices.

In June of 2012, it would have taken 66,500 share of Facebook to purchase the average home in Palo Alto. By March of 2021, that number was down to just 11,077 shares. Quite incredible.

Bitcoin ($BTC)

While I realize that Bitcoin isn’t a large employer in Silicon Valley, nor is it a stock, the original idea for this post came from a joke I made on Twitter back in 2017.

Well, at least the price of homes in Silicon Valley is dropping rapidly when valued in Bitcoin. $BTC 🤔

— Adam Nash (@adamnash) June 6, 2017

Most of you likely already know the story here. Bitcoin price appreciation in the past 12 months has been unbelievably high, so looking back to June 2012 is going to be somewhat jarring.

In June of 2012, the price of Bitcoin was about $9.40. By March of 2021, it had risen to $57,326.20. That’s a gain of over 609,753%.

The growth rate in Bitcoin prices, as measured in US dollars, has been so incredible, this chart is almost impossible to read in recent years.

For context, in June of 2012, it took about 153,586.2 Bitcoin to purchase the average home in Palo Alto. By March of 2021, that number had dropped to just 54.9 Bitcoin.

This, of course, has a number of dramatic implications. As measured in US dollars, or in real assets like Palo Alto real estate, the wealth of Bitcoin holders has increased dramatically. As measured in US dollars, the average price of a house in Palo Alto has increased by 117.9% in less than 10 years. However, as measured in Bitcoin, the average price of a house in Palo Alto has decreased by 99.96%.

There aren’t many people who invested in Bitcoin back in 2012, but a disproportionate number of them were in Silicon Valley. However, even based on recent numbers, the story is similar.

In March of 2019, you could have purchased the average house in Palo Alto for 702.0 Bitcoin. Just two years later, in March 2021, the average house in Palo sold for 54.9 Bitcoin. That means the average home in Palo Alto, as measured in Bitcoin, has decrease by 92.2% in just the past two years alone.

Silicon Valley Is Seeing Significant Asset Inflation

These charts are not meant to imply direct causality, but in many ways they confirm several economic facts about Silicon Valley that may not be obvious when looking at nationwide statistics.

Because technology employers in Silicon Valley compensate most employees with equity, it is very likely that asset inflation in stock (and crypto) markets has some impact on the housing market. This is likely exacerbated by the lack of new housing construction in Silicon Valley.

The fact is, if you are fortunate enough to have equity in one of the tech giants, or if you have been an investor in Bitcoin, houses might actually look cheaper in 2021 than they did in 2012, or even in 2020.

What is most surprising about the data refresh is the apparent detachment of equity and crypto prices from the prices of Palo Alto real estate. There are a number of potential reasons why this might have happened. One theory is that real estate markets move relatively slowly compared to equities and crypto, and so the rapid price increases of 2020 have not yet worked their way into the market. A second theory is that large technology company compensation has been shifting away from stock options to RSUs, leading employees to hold less stock as they convert their shares to cash on vesting. A third theory is that we’re seeing complicated effects from COVID, as windfall money from equity and crypto markets may be flowing into other places rather than local real estate.

(Before the San Francisco crowd gets too rowdy, there is absolutely no evidence yet that more money is flowing into San Francisco real estate instead of Palo Alto this cycle.)

In any case, whatever the reasons may be, it is always worth checking the actual data to see whether it confirms or contradicts our intuition.

Let’s check back in another four years.

 

Just Getting Started…

“The journey of a thousand miles begins with a single step” — Lao Tzu

As the year draws to a close, I wanted to share some good news: Alejandro Crosa & I have started a new company, and we’ve raised an initial round of funding led by Ribbit Capital.

This was one of my goals for 2020, and I couldn’t be more delighted to be setting off on this adventure with Alejandro.

Alejandro is one of those rare talents that makes Silicon Valley special. When we first met, he was a contract engineer from Argentina, referred by Google to LinkedIn as we prepared for the Open Social launch back in 2007. But Alejandro had an unstoppable desire to learn, moving from platform to search to mobile. Together, we collaborated on a number of innovative prototypes, including a search engine for Twitter based on LinkedIn data (I still miss this one…)

His passion for new technologies, design, and great products is inspiring. 

Even after we both left LinkedIn, we kept in touch, and talked often about starting a company together. This is that company.

Alejandro & I believe that there is still a lot more to do in consumer fintech, and that through software we can help bring purpose to the way people approach their financial lives. 

Micky & Nick have built one of the pre-eminent firms in fintech; they risked their own money and believed in the category long before most venture firms were willing to invest. We couldn’t be more excited to partner with Ribbit on this new adventure.

I also want to thank Ross Fubini at XYZ Venture Capital for his support, as well as a humbling list of friends & angels for backing this new idea. So thank you to Gina Bianchini, Amy Chang, Walter Cruttenden, Dylan Field, Todd Goldberg, Minnie Ingersoll, Aaron Levie, John Lilly, Gokul Rajaram, Mike Schroepfer, Leonard Speiser, James Tamplin, Rahul Vohra, Liza Wang, and the rest of our investors for supporting us. 

Most importantly, we are hiring! If you are a talented engineer or designer excited about consumer fintech, and want to take a shot at building a platform that just might change the world for the better, come join us! 🦍

We’re just getting started. 🎉

 

Fintech 2025: The Next Wave

When I first joined Greylock at the end of 2011, Fintech wasn’t even a word that was commonly used in the venture capital community. Less than a decade later, however, Fintech has become almost ubiquitous. The category has not only proven that it can generate real revenues and scale, but also that it can create a large number of multi-billion dollar companies.

Unfortunately, when you are looking at seed stage opportunities, you have to think clearly about markets where there is the potential to build new multi-billion dollar product & companies.

When the bubble burst in 2000-2, there was a lot of thought put into what had worked and what hadn’t worked with Web 1.0, and those insights formed the basis of the next wave of software companies (Web 2.0 / Social). Some of those same issues have plagued Fintech 1.0, and may instruct how to think about Fintech 2.0.

As 2019 drew to a close, I took the opportunity to spend some time thinking about exciting new opportunities in consumer fintech. These continue to be areas that I’m investing against both as an angel and as a founder.

Beyond Millennials

For the last decade, a vast majority of consumer fintech startups have focused on millennial customers. This really isn’t surprising because the traditional financial services industry is so heavily invested in their older customers. By the numbers, households tend to build income and assets as they age, and the incumbents have spent decades servicing this customer base.

Young people, on the other hand, were the perfect market for new, unproven products and services. Young people are less tied to existing brands and services, more likely to be technophilic, and have simpler financial needs.

As we enter the next decade, however, consumer acceptance of new financial products & services will continue to grow, leaving new demographics open to new products & services. This would have been true regardless, but it seems clear that the COVID-19 pandemic has accelerated this opportunity.

These customer segments will be more competitive, but also potentially more valuable, as they collectively are much larger than the millennial market.

Single Player to Multiplayer

Traditional financial products & services are single player, which makes sense since people tend to expect a high degree of privacy around their finances, and products built for individuals are much simpler to design, market, and activate.

However, many new fintech services are built around a subscription-model, where three numbers tend to dominate: acquisition costs, average revenue per user, and churn rate. The last, of course, is a heavy determinate of lifetime value.

Multiplayer products & services have a number of advantages. Multiplayer products are inherently viral, pulling more people into the system and lowering average acquisition costs. More importantly, multiplayer products are fundamentally stickier, leading to lower churn rates and higher lifetime values.

One of the big shifts from Web 1.0 to Web 2.0 was designing products & services to be intrinsically multiplayer. This was one of the fundamental differences between the design of LinkedIn (Web 2.0) and Monster.com (Web 1.0).

Novel Products & Services

When web development began in earnest in the 1990s, most initial product concepts were just moving existing products & services online. Mail order catalogs already existed, but we put them online. Yellow pages already existed, but we put them online. There were a few novel products (eBay), but for the most part, we collectively just moved a lot of products into the cloud, with all the advantages that global reach & distribution brought.

Fintech 1.0 has also mostly replicated existing products, put them on modern technology platforms, and made them broadly available to customers (like young adults) who have been mostly underserved.

However, one of the great opportunities in Fintech long-term is leveraging technology platforms and distribution to create products & services that were not viable, or even possible, in the physical world. With Web 2.0, we saw a large number of products & services that just couldn’t have existed offline.

2020 Examples

Not surprisingly, ambitious founders have already started building products & services along these new dimensions.

Carefull is a novel service that connects Millennial & Gen X adults with the finances of their aging parents. Once connected, it provides peace of mind for customers that if anything unexpected happens with their parents’ or grandparents’ finances, they will be alerted.

PaceIt, led by Prof. Shlomo Benartzi, is working to tackle the problem of retirement income directly by building a service designed with retirees (or near retirees) in mind. This is one of the most challenging and potentially valuable financial services, and PaceIt believes they can deliver a highly differentiated service based on sound insights from behavioral economics.

Braid is a novel debit card designed from the ground-up for households and small groups (e.g. roommates), providing a standard way to transparently share expenses between groups of people.

Pillar Life is a digital platform that helps people protect and care for their aging loved ones. Pillar replaces outdated & messy physical files with a secure online vault where you can easily store, organize, and share all your family’s most important information like financial accounts, legal documents, medical records, and more.

2020 may have been a terrible year on most dimensions, but as an angel investor for over nine years, it turned out to be my most active one yet. Hopefully, this bodes well for the future of Fintech, and for the financial products & services we’ll all be able to enjoy in the coming years.

 

Joining the Board of Directors at Shift

Today, I’m happy to announce that I’ve joined the Board of Directors of Shift, a company that has spent the last 6 years reimagining the used car experience. Shift is a marketplace that buys and sells cars directly from consumers without all the usual shady tactics that run rampant in the industry. With Shift, buying & selling a used car is  simple.

In 1991, when I turned 16, I had my first used car buying experience. My father took me to several different lots where we looked at the almost random assortment of cars in our price range. As it turns out, my father is a surprisingly good negotiator and had no trouble walking away from a bad deal. Unfortunately, that meant we walked off each and every lot we visited that day empty handed.

Fortunately for me, my uncle saved us from having to do another day of traditional used car shopping, and I drove his used Toyota pick-up all through college and grad school. But for millions of people, buying & selling a used car is still too painful, expensive, and complicated.

A Better Way to Buy & Sell Used Cars

When George Arison & Minnie Ingersoll came to visit me to talk about the new company they had started, I was immediately impressed with their excitement for a truly mobile-first approach to buying & selling used cars. Over the years, I’ve been phenomenally impressed with the way the team iterated and expanded on their original vision. In 2017, I had the opportunity to sell a used car on the platform, and it was transformationally better than my previous experiences trading in cars to dealerships or selling the car directly through classified ads.

As a product leader & angel investor, I try to focus on products & companies that are working to reinvent a key customer experience. In 2014, I invested in just six companies; they included Gusto, OpenDoor, and Shift.

For many people, buying and selling a car is one of the largest transactions they make in their financial lives. The system has long been littered with opaque practices, overblown loans, and sleazy sales tactics. Taking the high road, Shift has made transparency their hallmark, listing out any fees, doing away with haggling, and making financing more user-friendly and easier to understand. They even built out a loan term predictor so customers can know for certain what they can afford before they even start shopping. 

The company is now slated to go public in the coming weeks, and has grown considerably on the West Coast, aided by its  first-class operations and Silicon Valley culture. Customers finally have a way to buy or sell a car for a fair price without leaving their driveway.

Joining the Board of Directors at Shift

I’ve spent my professional life working to build products that truly improve the lives of ordinary people: whether a working mom who uses eBay to earn a little extra income on the side, a young college grad beginning to build their professional reputation, or the up-and-coming eager to start saving & investing.

I felt fortunate to have been one of the original angel investors in Shift. I was delighted when we sold our car through the service. I’m now grateful for the opportunity to join George, Toby, and their team as they make the transition to being a public company.

• Press Release
• Company Blog

If you are looking to buy or sell a used car, please get Shift a try. Reach out, and let me know about your experience. We’re excited about the road ahead.

A New Year & A New Adventure

Some personal news to share today.  After a great tour of duty at Dropbox, I’ve decided to take the leap into something new.

Having a January birthday has always added a little weight to my New Year’s resolutions, and as it turns out, 2020 was a big one for me. 45 might not be the biggest milestone birthday, but combined with the weight of a new decade, it had me thinking deeply over the holidays. Fortunately, I was able to spend a good deal of time with friends & family, and by New Year’s Eve I felt comfortable with a simple, but important, decision.

2020 will be different. This will be the year that I go off on my own.

The hardest part of this process was telling my team at Dropbox. I feel so very fortunate to have had the opportunity to lead such an amazing group of professionals. And as proud as I am of what we accomplished in 2018 & 2019, I’m even more excited about what this team will deliver for their customers in 2020 & beyond. 

For me, I’ll be spending the next few months preparing for the long road ahead founding a company. As one of the growing number of “operator-angels,” I’ll continue to advise and support the talented teams at the companies where I’ve invested over the past 8 years. Primarily, though, I’ll be spending time on a couple of specific fintech ideas that I think have the potential to be great companies. 

I have spent over 20 years learning to build & design great products and great companies, but somehow never my own. As an angel investor, I’ve now helped fund and advise over fifty amazing founding teams, and have had a front row seat to their struggles and successes. It’s time to take the plunge.

And who knows? I hear 45 is the best time to start.

Be A Great Product Leader – Amplify 2019

On October 8, 2019, I was asked to give my talk, “Be A Great Product Leader” to a huge audience at Amplify 2019, the product management conference organized by Amplitude.*

The talk is named after possibly my most famous blog post on the topic of product leadership from 2011, Be A Great Product Leader.

For those of you who have seen earlier renditions of this talk, this version was cut down to thirty minutes, and as a result has a subset of topics. All of the lessons in this talk started as blog posts:

1. The Secret to Product Prioritization. Three Buckets
2. Find the Heat. Don’t Be Afraid to Talk About Emotion.
3. Einstein’s Razor. Make Things As Simple As Possible, But Not Simpler.
4. Obsess About Your Non-Users. Growth Comes from Them.
5. Solve the Product Maze Backwards. Think Back from the Future.
6. Know Your Superpower. Product. Design. Engineering.

Over the past ten years, I’ve given versions of this talk at over twenty different companies and conferences, but there has never been shareable video of it. Fortunately, Amplitude captured the video and  posted full video of all of their talks, including mine.

Product leadership continues to be a hot topic in the industry, and I hope that these lessons will help inspire more people to become great product leaders.

 

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* Special thank you to Melinda Byerley for making the introduction!

How Will You Measure Your Life?

Source: Deseret News, Jan 24, 2020

On January 23, 2020, Clayton Christensen passed away at the age of 67.

I found out about his passing during my commute home from work on Friday, and it left me reflecting deeply on my experiences with Clay. I enrolled in his class back in 2000 at HBS, and was fortunate enough to have him agree to be an advisor to me on an independent project on the topic of disruption. Over the years, when I would visit HBS for recruiting or for a case study, I would always try to stop by to see him. Ever gracious and thoughtful, he may have been the most influential professor in my life.

There have been some wonderful pieces written about Clay in the past couple of days, mostly reflecting on his impact on management theory or his lifelong dedication to his family and his church. The list of his accomplishments is appropriately long. However, there are a few personal details I’d like to add to the story.

First Meeting

Many people are familiar with Clay’s work on innovation and disruption, made famous by his 1997 book, The Innovators Dilemma. It’s always shocking to me when I meet people in Silicon Valley who haven’t read it – that’s how fundamental it has been in shaping my thinking about business & strategy.

However, the professor I met at Harvard twenty years ago didn’t talk about innovation, disruption or how to build a successful business. He talked about the morality of business, the ethics of leadership and about his own personal journey.

Clay was a warm and friendly person, but when I first saw in him walk into our class, it was hard to ignore just how tall he was. At Harvard, the third row of seating is known as the “Power Deck” because when seated you are eye-level with the professor. I used to joke that in Clay’s class, it was the fourth row that was the Power Deck.

In some ways, Clay’s height made his approachability and humility even more surprising and authentic.

Clay’s class was supposed to be about strategy, but he opened his first lecture with a discussion of people. He spoke about how we spend most of the hours of our adult lives  at work, and how impactful those hours are on the emotional wellbeing of people even outside of work. He asked us to think about great managers we’d had in the past who supported us and gave us energy, and terrible managers who had drained us of it.

And that’s when he told us that he believed that being a great manager was one of great moral responsibility, because your leadership would either make the people who worked for you miserable, or they could bring those people joy & accomplishment.

When Clay talked about leadership, he talked about it with a clarity and conviction that is rare. To this day, when I take on a new leadership position, I talk to my teams about the responsibility I feel to them based on Clay’s words.

Professional Journey

Clay’s professional journey also resonated with me. Most people don’t know that Clay himself was a founder, starting a company focused on advanced ceramics back in the 1980s material science boom. It’s a bit of personal trivia, but my first love at Stanford  wasn’t Computer Science. It was the Introduction to Material Science that made me decide to major in Engineering.

But after that experience, Clay had decided to go back to school. It is unusual for an MBA to go back to get a PhD, but he went back because he wanted to study management and teach. His passion for a more rigorous framework on how managers make decisions led him to the insights that became The Innovator’s Dilemma, and the career that we all know him for. His fundamental belief that managers were intelligent and capable led him to frame an incredible problem: how do large companies continue to fail when they have access to so many smart people and almost unlimited strategic resources?

However, his choice wasn’t purely motivated by academic or professional interest. He talked openly about his family, his wife and his children, and the life he wanted to create for them. He talked about his faith, and how he wanted to be judged in the end.

Not everyone who is religious leads an exemplary life, but for Clay, his faith seemed to amplify and enforce his ethical rigor. In his later work, he would argue that it was easier to hold the line ethically 100% of the time than 98% of the time, because one compromise leads to another, then another.

How Will You Measure Your Life?

Over the years, when I would visit Clay at HBS, he was always warm and encouraging. We would discuss each career move I made: eBay, LinkedIn, Greylock, Wealthfront. The clarity of his strategic thinking was always a gift, and his willingness to engage and debate when we disagreed was always a bit surprising to me. But Clay loved to sharpen his thinking, and had seemingly no ego tied to defending ideas or business strategies. He just loved finding more insight; a twinkle in his eye in the pursuit of a clearer glimpse of the truth. I always left of our conversations feeling amplified by both his support and his energy.

In 2010, Clay published a piece based on these ideas that became a book by the same name, How Will You Measure Your Life.  It is worth reading, and even re-reading.

I have a pretty clear idea of how my ideas have generated enormous revenue for companies that have used my research; I know I’ve had a substantial impact. But as I’ve confronted this disease, it’s been interesting to see how unimportant that impact is to me now. I’ve concluded that the metric by which God will assess my life isn’t dollars but the individual people whose lives I’ve touched.

I think that’s the way it will work for us all. Don’t worry about the level of individual prominence you have achieved; worry about the individuals you have helped become better people. This is my final recommendation: Think about the metric by which your life will be judged, and make a resolution to live every day so that in the end, your life will be judged a success.

Rest in Peace, Clay.

Three Types of Risk: Making Decisions in the Face of Uncertainty

One of the fond memories I have of my first two years at LinkedIn was coming into the office almost every Sunday to spend a couple of hours with Reid Hoffman.

Our conversations covered a wide range of topics, but the time ensured that we were fully aligned on the strategy of the company and the priorities we were pursuing.

One of the topics that I was most fond of discussing was the nature of risk, and how to best lead teams when facing the various types of risk that are commonplace at hypergrowth startups.

Here, Reid never varied, and I quickly adopted his framework as my own. In the end, most of our productive discussion involved deciding which of three types of risk a particular decision involved.

Three Types of Risk

Categorizing the type of risk you face is incredibly useful in helping teams understand how much effort and consideration to spending on making various types of decision in the face of uncertainty.

For hypergrowth startups, risk can be categorized as one of the following types:

1. Fatal Risk
2. Painful Risk
3. Embarrassment Risk

Fatal risks are true bet-the-company issues. They are not that common, but they deserve clarity and focus. If you get the answer wrong here, the company is dead. These risks are unavoidable in early-stage startups, but as companies grow they become more and more uncommon. In fact, most large companies lose the ability or even recognition of these type of risks as they age.

Painful risks involve decisions that have significant repercussions if they go the wrong way. You might miss a key goal, or lose key people. They are recoverable, but there are real ramifications to getting the answer wrong.

Embarrassment risks have no significant impact if they are missed. All that is necessary is to acknowledge the mistake, change course, and move on.

Embarrassment risks are particularly difficult for smart & ambitious people, largely due to insecurity and ego. People want to be perceived as intelligent and successful, and they incorrectly map that to always being correct.

Unfortunately, most people at hypergrowth startups spend far too much time debating embarrassment risk, and they don’t take enough painful risks.

What About Type 1 & Type 2 Decisions?

Jeff Bezos has more recently popularized a different framework, based on two types of decision. This framework is often described in the context of the decision to move forward with Amazon Prime, which at the time was mostly a judgment call versus a data-driven decision.

In his framework:

• Type 1 decisions are irreversible. Spend time on them.
• Type 2 decisions are reversible, like walking through a door. Make them quickly and move on.

Overall, this framework is helpful. Thinking through the reversibility of decisions helps prioritize speed vs. perfection. When it comes to execution, the perfect truly can be the enemy of the good enough.

The problem is that almost every decision at a company is reversible, so it tends to not provide that much insight into why some risks feel harder to take than others.

Lessons in Execution

In some ways, you could describe painful risk & embarrassment risk as two sub-categories of Type 2 decisions. The speed of execution depends on taking these type 2 decisions quickly and aggressively, framing them as risk, and clearly articulating what the team will do if it doesn’t play out as expected.

Leaders need to embody this type of decision making, to give permission to newer employees to take risks and communicate their decision making effectively.

Otherwise, a spiral of low expectations and low-risk options will quickly put you in a vice when faced with more aggressive competitors. Worse, you won’t be taking enough shots on goal to learn fast enough to have high odds of success.

Large companies trend towards this problem because decisions become increasingly about the personal positioning of individuals for their own advancement, rather than optimizing for the best results for the company or their customers.

Ironically, taking painful risks may be the only way to set yourself up for exceptional outcomes.

The next time you see your team facing a decision in the face of uncertainty, try to quickly agree on what type of risk you are facing and what type of decision you are making. In most cases, you’ll be able to make decisions more quickly and save your time for the rare, but very real, risks that you have to navigate with your product and your business.

 

The Future of Drone Safety

Every time I go to the CODE Conference, I learn something new. There is something about watching some of the most prominent technology executives and founders responding to questions from talented journalists that gets me thinking.

Four years ago, I wrote about the transition technology CEOs needed to make from economics to politics. Coming back from this year’s gathering, there  is no question in my mind that this insight turned out to be true. Responsibility was a significant theme this year. As the technology industry continues to grow and mature,  more and more people are looking to investors and technology leaders to think ahead about potential issues that will happen when their creations become ubiquitous.

It got me thinking about drones.

The Problem with Drones

The FAA projects that the number of drones will reach 7 million in just the US alone by 2020. The growth rates for both consumer and commercial drones continue to grow at a rapid rate. The FAA estimates that there will be over 3.5 million hobbyist drones in the US by 2012.

Over the past few years, I’ve made a few investments in startups in the drone space. But until last year, I hadn’t given significant consideration to all of the safety issues around drones, particularly as they fly over large crowds or critical infrastructure.

The problem is fairly simple. Large venues, like sports stadiums, and critical infrastructure are largely defenseless against drones. Whether it’s a music festival, a weekend football game or anything of that sort, most people don’t realize that event managers really have no solution to protect a crowd. Whether accidental or intentional, there is a real risk that a malfunction or crash could harm people.

The Need for Active Measures

Long term, of course, we can imagine a world where drones can be programmed to avoid these spaces, (Airmap is a great example of a company making this happen). However, We can’t just assume or depend on this to be universally true – that risks the mistake of being overly idealistic. There needs to be an active solution to protect critical areas.

There are a number of companies working on solutions that involve intercepting and disabling drones that enter space that needs to be protected. In fact, there are solutions like drone on drone capture (with nets) 🕷, projectile solutions (shoot it down) 🔫, even flamethrowers! 🔥

Unfortunately, these kinetic measures make little sense in cases where the drones are flying over areas that need protection. If the concern is a drone crashing into a crowd or important infrastructure, these solutions run significant additional risk of the drone or pieces of the drone causing damage on impact. While there is definitely a market for kinetic solutions in the military and related markets, but it seems like a bad fit for the majority of the simple but real threats out there.

A Software-Based Solution for Drone Protection

Last year, as the co-chairman of ICON, I had the good fortune to meet Gilad Sahar, the co-founder and CEO of Convexum. With the unique insight that comes from military experience with both the costs & benefits of active solutions, they have developed a non-violent, software-based active measure to help automate perimeter protection from drones.

The concept is fairly simple.

Convexum has developed a device that allows companies & governments to detect when a drone is entering a restricted space, take control of the drone, and land it safely. A cloud-based service ensures that all Convexum devices have up-to-date signatures for known drones.

Initially, they are seeing significant demand for this solution around critical infrastructure, like energy development, and sporting venues. Long term, I can easily imagine a future where a non-violent solution for drone protection would be highly desirable anywhere we don’t want to bear the safety risk (like schools).

Working with Government

Europe has already provided a clear path for companies and government entities to receive the permits & exemptions needed to deploy this type of solution. (In fact, Enel has already deployed a solution to protect power plants.) Congress & Senate debating this now in the US, but seems to be one of the few remaining areas of true bi-partisan alignment.

I’ve personally been so impressed with Gilad & Convexum, I’ve decided to help them by becoming an advisor to the company.

Let’s hope this is part of an increasing pattern of entrepreneurs and investors thinking ahead about safety and regulation, and supporting technologies early that can help solve these eventual problems.