Capturing the view from Mori Tower, Roppongi Hills, Tokyo (Photo credit: Junko Nagao)

Since I moved to Japan over a year and a half ago, almost every business meeting I have had starts the same way. We file into a room, smile politely at each other, parade around the table to exchange business cards in the proper order, we sit down in our prescribed seats, and then there is an inevitable moment of awkwardness, followed by a perplexed stare, alternating between me, my Japanese colleague, and my business card.

In Japan, being polite, particularly in a business context, is of the utmost importance. I know people are not trying to be rude. I’m used to it by now, and I can’t blame them. I know I am unusual. The first question they ask is usually to slyly confirm that I am actually a Managing Partner of Fresco Capital. Given my age, my gender, and my most obvious foreign-ness, the fact that I am sitting across from them as an equal is undeniably shocking. The reactions are always entertaining — some are delighted, some are clearly offended, others in complete denial.

The first few months of this, my cheeks would burn in embarrassment as I responded politely to confirm my position and deliver the introduction of Fresco Capital, my heart filled with pre-emptive defensiveness and the chip on my shoulder aching deeply. Now, I revel in the routine and am grateful for my ability to use their response as a strong filter for potential partnership. You have to be open and curious to new things to find success in the world we live in today, and here I am, able to gauge that within the first thirty seconds of a meeting. Lucky me.

Then, comes their real question, accompanied by a puzzled brow and a heavy air of anticipation: “Allison-san, but why are you in Japan?” I used to dread this question, because just like anything in our quickly advancing world, the answer is complex and there are an infinite number of ways I could reply, most of which would not be relevant or appropriate for a business context. So, I experimented with different responses, carefully gauging the subsequent temperature of the meeting given a certain response, and attempted to rapidly iterate my way to a productive answer. At least I learned quickly that sarcasm is not well received here.

Connecting the Dots

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever.”

— Steve Jobs

Reflections at the Imperial Palace, Tokyo.

Part of the problem was that, until very recently, I honestly didn’t have a full picture as to why I believed so strongly it made sense for me, and for Fresco, to set up our first new global office and team in Japan. Sure, I had an intense personal attraction to Japan, as well as a strong “Spidey sense” that there was a big opportunity for us to be one of the few global VCs in Japan. And whether it comes to people, investments, or partnerships, I’ve learned to trust my gut.

When we decided to bring Fresco to Japan, the dots looked a little bit like this:

Pros:

• I’ve wanted to live in Japan since I was ten years old, when I made a best friend at summer camp who was from Tokyo. She started teaching me about Japan, and I was hooked. I tried to move here after college, but couldn’t make it work, and ended up going to Goldman Sachs in New York City instead.
• I love sushi more than anything else in the world. Seriously, though.
• Tokyo air is cleaner than Hong Kong, and Japan is arguably the safest country in the world.
• We were just starting to raise a new fund, and there were interested investors in Japan.
• My partners were keen to expand our global presence and set up a new international office.
• Our portfolio companies were interested in expanding to Japan, or were already beginning the process, but needed help.
• My then-fiance’s employer asked him to move to Tokyo and long distance sucks.

Cons:

• My then-fiance became my ex-fiance, which was sad and embarrassing and very clearly crossed off more than one of the pros.
• As a result, I knew exactly zero people in Japan.
• I hadn’t spoken Japanese in nearly ten years.
• After finally building our reputation in Hong Kong and China, we would be starting from square one, yet again.

Now that I have been in Japan for a year and a half, we raised a fund from Japanese LPs, I built a team of the most intelligent, forward thinking, and well connected Japanese partners, and we have brought four of our portfolio companies to Japan, I am starting to see the dots crystallise into a critical pattern that clarifies that initial gut feeling of why I and Fresco and need to be in Japan right now.

So, Here’s Why:

Our role as venture capitalists and my personal role as a trailblazer and explorer of the unknown is to create the future. We are living in unprecedented times, and the ways of building value in the past are no longer working. Our personal lives, our governments, our corporations, our jobs, and our infrastructure are being transformed by fundamental shifts in demographics, technology, and globalisation. Consequently, these key trends are shaping the period in which we live, and Japan is the first country in the world delicately poised on the precipice of these changes, reluctantly forced to navigate this complex but critical new era.

Just what are these critical shifts how are they playing out in Japan?

Reflections at the Imperial Palace, Tokyo.

1) Demographics

As a society, we created a series of formal structures to help individuals navigate their lives on Earth. These include the construct of marriage, a formal education system, corporate careers, pensions, and healthcare. Today, people are living longer, women are economically empowered, birth rates in developing countries are declining, and the Baby Boomer generation is retiring. These trends are forcing us to re-examine how and why we plan our lives and redefine the social and political structures that we have traditionally relied upon.

Japan is on the cutting edge of this trend. Long known for their health and long life expectancy, a child born in Japan today has a 50% chance of living to 109, the longest in the world. Simultaneously, birth rates in Japan have declined and the overall population is now declining at the fastest rate globally. Every year, Japan sells more adult diapers than baby diapers. How will the jobs market and government infrastructure adapt? A retiring generation of Baby Boomers is dramatically stressing pensions and healthcare, which were previously predicated upon an assumption that the current working population could support retirees. How will the country cope and how will infrastructure need to transform to support these unexpected trends? I don’t know, but we will soon find out.

Shibuya crossing, photo credit Daryan Shamkhali

2) Urbanization

As outlined in The 100-Year Life, “We are quietly witnessing the most extraordinary migration that humanity has ever experienced… from the countryside to the city.” In 2010, 3.6 billion people lived in cities, but by 2050 that number will be 6.3 billion. This is changing the shape and needs of urban infrastructure, and technology pays a key role in creating efficiencies that did not exist before.

Again, Japan is on the forefront of this trend. With over 38 million people, Tokyo is the largest city in the world. As of 2015, 93.5% of the population in Japan lives in cities (compared with a global average of 54%, 81% in the United States, and 55% in China). Not only that, but the migration continues as the population ages and technology jobs are proliferating in urban centres. Tokyo’s population is increasing at nearly 1% per year, and 90% of the people moving to Tokyo are between the ages of 15–29, even as the general population of Japan is rapidly declining.

Ueyama, Okayama. Rural areas have been hit hardest by the stagnating economy.

3) Stagnating Economic Growth

After the Great Financial Crisis rocked the US economy, then Europe, then the rest of the world, we have entered an unprecedented time of economic stagnation. Governments have responded by cutting interest rates to near-zero, and this has impacted the growth and development financial markets, savings rates, inflation, and GDP growth. Though the US and Europe are only now starting to grapple with the long term effects of these policies, Japan has been plagued by these trends for years and is now being forced to find new ways to climb out of its economic rut.

Vending machines and advertisement for the Robot Show, Shibuya.

4) Technology & Automation of Jobs

The internet is a relatively recent invention, but the change it is bringing on the world is accelerating rapidly. Personal computers have democratised access to information and resources, and social networks have opened up opportunities and connections that were previously seen as proprietary. Technology has impacted or been integrated into all products and services, and in this sense, every company is now a technology company in some way. As a result, every job is now a technology job, many jobs are now being automated or replaced completely, and new jobs are emerging on an hourly basis.

Both historically, with the automation of the manufacturing process, and socially, with the Japanese cultural fascination with robots, Japan has adapted and even embraced automation unlike any other country in the world. With a generation ready to retire, Japan is in a position to remain a thought leader in this sense. By 2060, the population in Japan is expected to be 87 million, a dramatic reduction from a high of 127 million. As stated in the 100-Year Life, “rather than worrying that robots are going to take our jobs, we should be delighted that they are arriving just in time to boost a flagging working population and maintain output, productivity, and living standards.” Indeed, if there is anywhere in the world where that may be true, it is Japan.

The Olympics are forcing Japan to think more globally.

5) Globalisation

As evidenced by the refugee crisis in Europe, global trade, the outsourcing of jobs, the current proliferation of cyberattacks, shifts in commodity prices, and the increase in correlation of global financial markets, the world is more connected than ever. People are scared, national identities are being threatened, and politicians are struggling to figure out how to adapt. As evidenced by Brexit, the election of Donald Trump and the subsequent impending reality of a wall, we are now facing resistance to globalisation in the form of isolationism and anti-immigration policies.

Though it remains to be seen how this will impact the US or European economy, for better or worse, this inward-looking, nationalistic approach is not new to Japan. The impact it has had on economic growth and innovation is alarming, and with the 2020 Olympics looming, Japan is now facing a critical moment where its leaders are seeing that opening up to the rest of the world is the only option. Again, what this looks like and how Japanese society, culture, and the economy will adapt remains to be seen. But the time to find the answers is now.

Conclusion: An Era of Questions

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.” — Rainer Maria Rilke, Letters to a Young Poet

The view of Mt. Fuji from Yamanaka Lake, Yamanakako

More than ever, the future is plagued by questions. How will we, as both individuals and societies, adapt to these critical shifts in the the fabric of our world? What will the future look like and what role should we play in creating it? Many people travel the world looking for answers. What I have learned is that, thanks to the internet, Google, and good old human egos, answers are everywhere. However, given the complexity and interconnectedness of this next stage of growth, none of them are fully relevant.

My raison d’être in Japan is not to find the answers — because, there are none (yet). More importantly, living and working in Japan is forcing me to face and engage with the most difficult questions facing our generation. Just like I had to iterate my way to the proper response to, “Why am I here?”, Fresco’s presence in Japan is allowing us, our partners, our investors, and our portfolio companies to test solutions at a pace not possible anywhere else in the world. Hopefully, what we discover together will prove to be one of the most valuable exports Japan has ever seen.

For the last 15 years or so, I’ve been making the trek to the Consumer Electronics Show out in Las Vegas every winter. It’s where all the coolest next-generation gadgets and technologies are showcased.

I just got back from CES 2017 and I have to say it was one of the most exciting events I can remember. There were more than 177,000 people at last year’s event, and if I had to guess, I’d say we beat that number this year.

If you’ve never been to CES before, let me try to paint a picture. Events are scattered all across the city. But no matter where you wind up, the geeks hang out in the back showcasing their wares in small booths while the brand-name companies (e.g., Samsung and Sony) set up shop up front in larger booths.

That being the case, it appears the Internet of Things has finally become mainstream. This year, the IoT booths moved from the back of the room to the front of the room while VR and AR technologies were all over the back booths this year. We can expect these nascent technologies to make it to the front over the next few years as they develop further.

CES continues to attract more and more folks from around the globe. This year, there were more foreign entrepreneurs, investors, and professionals at CES — from China and Japan in particular.

There were also a number of other themes I picked on over the four-day event.

Smaller Companies Turned Out

At an event as large as CES, you obviously expect to run into the Amazons, Nikons, and Sonys of the world. (e.g.Nikon Project Helix)

They’re still there. But nowadays, the smaller booths are filled up by companies located all across the world. This year, companies from (not surprisingly) China and (surprisingly) Paris appeared to have spent the much money to showcase at CES.

Having all of these smaller companies with cool little products is great. It’s not every day that you’re able to check out an ozone ionizer that you can stick in your shoe to get the smell out. Or take a 3-D body scan and get a five inch 3-D printed version of yourself.

Fifteen years ago, that kind of product wouldn’t have a chance at CES. Today, they’re everywhere. What is more important is that they are not even in production yet, just a small batch run and now taking pre-orders or publicizing their Kickstarter. This wasn’t possible, even five years ago.

Car Manufacturers Prefer CES

The future of the car seems to hinge on technology.

Cars were everywhere at CES this year. There were connected cars and autonomous vehicles. Car manufacturers appear much more interested in releasing cars at CES instead of at the standard auto shows. They’re not going to the Detroit Auto Show to launch a new line; they’re coming to Vegas and doing that at CES.

All of the big name manufacturers — like Ford, BMW, GM, and Volkswagen — made the trek to CES. Of course Faraday was there, but more importantly, they took 64,000 pre-orders at CES for their $200k that is only in the concept phase. Even compared to last year, it was very apparent that technology is taking over the automobile industry.

The IoT Was Really Everywhere

At CES events in the past, IoT booths were all about mesh networks and sensors. Today, we’re seeing sensors in consumer products.

Everything is connected. There was even a connected hairbrush, which is the epitome of an unnecessary connected device. Still, products like that are great because in the coming years, the market will push out unnecessary devices. It’s just a simple issue of supply and demand.

Samsung — which has successfully shaken off its Note 7 debacle — was all the rage at CES. They built an entire connected kitchen which was completely mobbed. Everything was connected to the point we literally thought everything was connected. Unfortunately, the sink wasn’t connected — which we were kind of bummed about. It is silly. But if everything else is connected. . .

Thank You, Alexa

Alexa was truly everywhere, too.

Amazon opened up its API, and have manufacturers very obviously jumped all over it already. It bears repeating: Alexa was everywhere. Amazon even found a way to partner with physical buildings and futuristic robots.

Amazon made a huge investment in Alexa, which has already found a home in a number of IoT applications. In essence, Alexa is now the interface for all IoT devices that connects everything together. Who knows what the future will hold?

Looking Forward: CES 2018

Drones are becoming increasingly popular, but it’s relatively still “geeky”. I suspect we’ll see more mainstream drones at CES next year.

There are so many startups working on AI, AR, and VR. I am expecting to pursue an enormous selection of small batch manufacturers working with these technologies in 2018.

See you in Vegas next year!

Some people think venture capital is just fine and doesn’t need to change. Others want to turn it into a hyper liquid automated platform.

It’s time to call bullshit on both views.

Traditional venture capital needs to be transformed and the process will happen one person at a time.

I gave a presentation to a group of family office investors and corporate investors about the “Do’s and Don’ts of Venture Investing” earlier this year using martial arts training as a metaphor. It covers a lot of basics, with details here and here.

The discussion below starts with some of the traditional issues around risk and return, then moves on to ideas about how to transform venture capital.

At the black belt level, the emphasis shifts to higher level training, including awareness of self and the environment.

A typical mistake for a beginner in karate is to punch before stepping. This results in no power — as we learned in brown belt, strength starts from the bottom and flows upwards. It seems easy which why it’s actually difficult and in fact many people simply don’t even notice the mistake. Even with the incorrect technique, it still feels correct.

Getting the timing right in venture investing is similarly a challenge. The biggest mistake is to sell too early. The only thing worse than missing out on a billion dollar investment is being an early investor and then selling out to a new investor for a small profit and missing out on the much bigger gain. I know of one investor who came in very early into Alibaba only to sell soon just to get the money back because of concerns about risk. Whoops.

Of course, there are certain situations where it’s better to sell. This can happen especially when a wave of lemming behaviour overcomes investors to jump into a theme.

There’s no formula for getting the right timing to sell, but compared to all other investments venture capital is about long-term returns, so you should be thinking in terms of years and decades, not day trading.

The foundation of looking at the risk vs. return over time is to always evaluate decisions as if you were investing for the first time. In reality, that’s difficult in venture capital because of the knowledge built up over time after an initial investment and the overall lack of liquidity. Still, it helps to set the right framework. A more detached assessment of risk vs. return tends to lead away from binary all or nothing decisions and towards a more measured approach.

Of course, the process is not all about numbers. In fact, understanding the motivation of founders, other investors and of course your own goals is critical. If the company has been grinding it out for 10+ years and everyone is ready to move on, it may not matter that the best financial decision would be to continue for another 10 years because from a motivation perspective the journey has finished. Conversely, if the company has just received a lucrative M&A offer, this might be just the catalyst for a highly motivated founder to push for a more aggressive scaling up strategy and reject the early exit. Human inputs can be the most important factors when it comes to evaluating risk vs. return.

People are surrounded by external distractions. In addition, our minds are constantly creating internal distractions. This noise stops us from concentrating.

One description of traditional martial arts is “moving meditation”. Embedded in this description is the idea of having an empty mind. The first step is to navigate external distractions. The more difficult challenge is to manage internal distractions. Rather than trying to push the distractions out of our mind with mental energy, which is impossible, the training emphasizes acknowledging distractions and then being able to let go of them. Empty mind is not a static state of being, it is a dynamic process.

At first glance, it seems ridiculous that an empty mind would be an important skill for venture investing. Traditional wisdom suggest that experience, especially domain expertise, is necessary to be a successful venture investor.

The problem with experience is that it is actually one form of noise. The deeper the experience, the louder the noise. If you have 23 years of experience building microcomputers and some kid comes along with an idea for a personal computer, all your experience screams “impossible, no way this will work”. If you’ve spent all your career selling packaged software and someone suggest selling software for a monthly subscription, your instincts react immediately that customers simply wouldn’t trust software that they don’t own. If you’ve built billion dollar satellites and a young team proposes to create a network of cubesats, the first reaction is to treat it as a toy project. That’s the voice of experience speaking.

An empty mind allows even experienced venture investors to stay open to new opportunities. You can’t ignore your experience — those thoughts will always be there. Instead, acknowledge them, let them float away, and then let your empty mind stay open.

The common assumption is that martial arts focuses on fighting. But upon closer inspection, there’s a clear emphasis on peace by many traditional martial arts teachers. Fighting is the last option of traditional martial arts.

Many startup founders and venture investors make heavy use of war and sports metaphors — destroy the competition, hunt down customers, don’t be a loser.

Words and metaphors influence behaviour and actions. So by definition people being led by these words will be approaching the world with at zero sum perspective. For them to win, others have to lose. Zero sum thinking implies a lack of new value creation. If you believe that technology is supposed to create new value, not simply take value from others, then by definition these zero sum metaphors should be rejected.

Of course many others will continue to view the world from a zero sum perspective no matter what you do. Instead of wasting your energy on constantly fighting with them, focus instead on partners who you can trust.

Trust is much easier to build with aligned incentives and shared values. Aligned incentives alone may not be enough if the partner is going to find a way to cheat at the first opportunity. Shared values create great intentions but without aligned incentives, there may be no tangible outcomes. So it’s important to have both.

The right partners will help you reach your goals faster no matter what games others are playing.

Reaching a black belt level in traditional martial arts is not an end goal. It is more like reaching the starting line of the journey. At the higher levels, this learning includes the willingness to embrace paradox in many ways.

Traditional karate training obviously places a big emphasis on learning the basics. The only way to do this is through repetition so that it becomes automatic.

But the ultimate goal is not to become a clone of others from the past. Instead, every single karate student has a unique signature style. If you try to develop your signature style at the white belt level, you’ll just be fooling yourself. The style develops naturally over time without any extra effort through the process of repetition.

Learning from other investors about venture investing is a great shortcut. After all, nobody has the time to invent it all from nothing. To this day, I’m still reading Fred Wilson and Brad Feld on a regular basis.

You should absolutely learn from what venture investors are sharing both in public content and in private meetings.

But a copy and paste approach is unlikely to be optimal. Every venture investor’s background is unique. Each era is different. And it’s all path dependent. As an example, one of the big differences about our team at Fresco Capital compared to most other venture investors is our global cross-border approach. Most early stage investors are local and that works for them. We’ve chosen to be different precisely because of our background and experiences.

Instead of a copy and past approach, better to take the time to find trusted partners and work together with them. Co-create solutions that meet your unique needs. The ideal partners adds strengths to fill your gaps. This could be knowledge, network or other resources.

A key part of our global approach is working with local partners who are on the ground everyday in the local market. So just being global is not enough — working with these local partners is a key differentiation.

Martial arts starts with physical training. At a certain point, however, the mental and spiritual aspects of martial arts become more important than the physical training.

This doesn’t mean that the physical training is not important. The physical training is a gateway to reach the mental and spiritual benefits. Rather than being independent, they are integrated.

Venture investing starts with financial returns. This has to be the foundation. And many people do view venture investing as a box that takes money in and spits money out a few years later.

But this view overlooks the potential direct and indirect benefits beyond just the box of cash perspective. There can be positive effects on revenues, efficiency, and speed for related businesses. There may be harder to measure, but perhaps even more important, soft benefits such as upgraded team skills, improved innovation and entirely new business units which grow larger than existing businesses. Most importantly of all, all of this investment in innovation can, and should, be used to actually improve people’s lives.

It’s important to emphasize that these additional benefits are unlikely to materialize if financial returns don’t set a strong foundation. So start with the financial returns. But don’t limit your imagination to a box of cash. The ultimate potential is much bigger.

Venture capital investors are always questioning and challenging assumptions in other industries. It’s important that venture capital itself faces the same kinds of questions and challenges.

While industry insiders are looking for new ways to differentiate, a little extra push from external forces can only help accelerate the process.

Ultimately, the best way to learn something is share it with others. In karate, this means training new students and then having them train students. This passes on the physical skills plus also the philosophy and values. None of this can be truly learned by reading a blog post or watching a video.

There is no substitute for person to person training.

Historically, venture capital was a very secretive industry. Knowledge was not shared and venture capital firms put a lot of efforts into controlling information flow. This started to change in the past 15 years as the industry started to open up. Blogs and in person events have allowed people to learn more about venture investing. But the reality is that most of the activity is still behind closed doors.

True innovation requires an open ecosystem, and venture capital also needs to join this trend. So our view is that successful venture investors should not be trying to hide the secrets of investing from others.

We believe there is tremendous value to be created in sharing knowledge about venture investing with others. More and more new investors are getting involved in venture capital. Without effective co-operation, that money may be completely wasted on bad investments.

Rather than hoping that other investors fail, we believe that the startup ecosystem desperately needs more high quality investors. This is not a zero sum game.

Of course, the challenge is to identify the right kinds of partners. There has to be an alignment of both values and incentives.

There’s a saying in karate: “a black belt is just a white belt who never gave up”. Learning to learn is the most important lesson of all. I’m still learning plenty about both karate and venture capital.

It’s this learning that is the secret power of how we can transform venture capital one person at a time.

At the start of 2017, people are planning for the year, quarter, month, week and even day. If you plan for 10 years, that’s viewed as long-term. A few crazy people have a 100 year plan. But who has a 1,000 year plan?

Hiroshi Tsukakoshi. I came across his masterpiece, Tree-Ring Management, at a bookstore in Narita airport, hidden in the tiny English section between travel and language books.

Tsukakoshi gives a 100 year calendar to all of his new employees when they first join and also asks them to think about their 1,000 year plan.

Why?

He gives his own reasons in the book and you should read those directly from him. Here’s why I like the idea.

1) Take the long view, appreciate now

It’s not about me or you. It’s not even about my children or your children. It’s about generations upon generations in the future. That gives us perspective from the long view. To see beyond the horizon.

At the same time, the length of our individual lives is insignificant. Mark your forecast death date on a 1,000 year calendar. Even if you’re off by 23 years, it’s still roughly in the same spot. This gives you the emotional conviction that time is short. Appreciate the moment you have right now.

2) Dream big, start small

To make a positive impact that lasts 1,000 years ain’t easy. It’s like rolling a snowball down a hill. Even when you die, the snowball is going to be small. But if the snowball is made in the right way and the hill is long enough and various random elements align, just maybe it’s possible that in 1,000 years the snowball is still rolling and growing. The only way to get there is to dream big.

To make that giant snowball, you don’t start by building a giant snowball. You start by making a small snowball. Then finding a mountain. Then rolling. And learning from what happens. Maybe you made a mistake creating the snowball. Maybe it was the wrong timing. Maybe it was the wrong mountain. Keep learning and doing. But start small.

3) Everything connects, improve yourself

We’ve got social networks, airplane networks and AI networks. The list is endless. In the past, it really could take 1,000 years for an idea to spread across a network. Now it can take 1,000 milliseconds. This creates a giant opportunity for a 1,000 year plan to impact more things faster and is one key difference from the past.

But everything being connected is also overwhelming for us. A 1,000 year perspective helps eliminate the noise. Before I can tell you how to improve, I’d better start by improving myself. Before you tell others where to focus their attention, it’s worth managing your own attention habits. Before we can change history, we have to be able to change ourselves.

What?

If you take a 1,000 year view, what should you do?

1) Find something

Explore. Maybe you’ll find something new. And it’s not just about physically going somewhere. Zero, heliocentricity and gravity were all found.

2) Make something

Create. Maybe people will like it. The wheel, the Tao Te Ching and the Mona Lisa are still pretty popular.

3) Change something

Transform. Maybe there’s a better way. Politics, religion and business are all in desperate need of an upgrade.

How?

Some people are already working with a 1,000 year plan mentality.

But it can be hard to start. Here are a few ideas.

1) Ask

Take a look at something around you right now and ask “is this the catalyst for my 1,000 year plan?” Most likely the answer will be “no”. So keep looking, and asking, all day. By the end of day one, you should have at least 101 bad ideas. Keep going till you find something interesting.

2) Observe

The next time you feel happy/surprised/angry or maybe just have a funny feeling in your gut, think about what’s causing that. Triggers of emotions tend to be good places to start looking. But don’t stop with emotions. Start observing everything.

3) Remix

Take two random things and combine them. The new remix is probably a bad idea but save it just in case. Make 99. They’re all probably bad but save them just in case. Keep going and at some point you’ll start to notice patterns and outliers. Follow those.

The best time to make a 1,000 year plan is now.

Start the survey

As an American living abroad, I have been shielded from a lot of the insanity of this year’s election, but even sitting here in Tokyo, halfway across the world, the vitriol and frustration is palpable. Sure, the Presidential Election in the United States is always charged with emotion, but as almost anyone who has voted in multiple election cycles would agree, this year is particularly heated.

People have said harsh goodbyes to friends, unable to empathise with their choices. Families have lost touch, fearful of the difficult conversations that would ensue if the topic of politics were to be broached (I’m sad to say I speak from personal experience on that one). The very foundation of the Two Party System has been irrevocably damaged. The question of what it really means to be an American remains up for debate.

One thing is clear: Shit is broken. The world we lived in previously has changed. The American Dream used to be: work hard in school, get good grades, go to college, get a good job, find a wife who will take care of your house, buy a house, work hard, rise in the ranks, save your money, provide your children with a better life than you had, rinse, repeat. Sorry guys (yes, I mean guys), no can do.

For most people, that is no longer an option. College doesn’t guarantee you a job anymore (trust me, even a Harvard degree is worth less than it used to be). And even if it does get you a job, your job has probably started to be replaced by technology. Entire companies are being dismantled, so the idea of a long-term career at one company is rare. Most women don’t want to be just wives anymore, nor do they have to be. As the Great Financial Crisis taught us so painfully, houses don’t always go up in value, so they are not a safe investment anymore. Interest rates are zero, so saving doesn’t do you much good either. So… yeah, shit is broken. The promises we were sold have turned out to be empty, and it’s not really anyone’s fault, either. It just is.

Sure, we can try to put it all back together again. Go ahead and try. Even if that were possible, it still wouldn’t work again. Why, you ask? But why, can’t we just go back to the glory days? One word: technology. Technology has not only changed the world, but it has changed how fast the world changes. As our most recent Nobel Prize winner, Bob Dylan, so eloquently pointed out… “The times they are a’changing.” And they’re changing faster than ever before.

Nassim Nicholas Taleb, author of the Black Swan, wrote a fantastic book called Antifragile. I have a short attention span, so I’m not going to lie to you, I only read half of it. But the takeaway is this; Fragility is when you break something, and you cannot repair it. Resilience is when you break something, and it can return to its previous state. Antifragility (the best way to be), is when you break something, and it returns to an even better state, more powerful and strong than before it was broken.

I can only hope that part of what makes America great is that we are the definition of antifragile. We need to have faith in our ability to heal these rifts that emerged from the US election, to face the difficult conversations that must take place, and to emerge a stronger, more informed, more creative, and more antifragile nation than we were before.

Doing that, however, requires us to take a step back, to set aside our emotions, and to take a deep look at the incredibly valuable and previously unseen information revealed by this election. So let’s remove the emotion, take a quick look at the facts brought to light by this year’s Presidential Saga, and dedicate ourselves to building something better in its wake.

What have we learned?

Technology has forever changed how we, as individuals, make decisions.

We used to live in a world where information was difficult to access, and we relied on key institutions like the political parties, the media (newspapers, TV personalities), academic and religious institutions to tell us what we needed to know to make an informed decision.

Now, we get our information from the internet. Anyone can read about the candidates online, anyone can publish their opinion, anyone can state a “fact”, or share their emotional reactions. We have become infinite information consumers and producers.

As a result, it has been shown that our grip on the truth is loosening. Our willingness to hear arguments counter to our own beliefs is weakening. Our strength to overcome our own biases is diminishing.

The systems that have kept our world stable have not gotten the memo.

The key systems and infrastructure which shape our lives were all created in a time before technology existed. The idea that we would be meeting our mates on Tinder, sharing our momentary thoughts and emotions on Facebook, carpooling to work in a stranger’s car, or tracking our daily food intake and steps on an app were completely unfathomable at the time of their creation.

So, where does it all break down? Jobs. The systems that support the world as we know it can be broken down as follows: corporations that provide us with jobs, education which prepares us for those jobs, the government which protects those jobs and protects us if we don’t have jobs. (Ben Thompson writes brilliantly on this system here, if you’re interested in learning more how this system was created and why.)

As technology accelerates, companies are being forced to adapt to increase margins, productivity, and profits for investors. As a result, jobs are being automated. Because technology evolves faster than we can learn, or the education system can provide us with relevant skills, we are losing our jobs. People without jobs are angry, disappointed, disenchanted, and scared. Not a good equation for an election, or for anything for that matter.

It is up to us to rebuild those systems in a way that will last.

Technology is not a trend. It is not a sector. It is an inevitable force redefining the world in every way. This will not change, it will only accelerate. As outlined by the concept of singularity, the rate of change of technology will only get faster and faster. This unleashes unfathomable potential, but can also be disastrous if we don’t create a system that can keep up.

This brings us back to the concept of antifragility. We can’t simply repair our broken systems. We can’t simply aim for resilience. The only option is to imagine and re-build the world on a foundation that gains from change, and as a result, actually gets stronger over time.

Okay, fine. But what can we do about it now?

First, we have to stop wishing for “the way things were” and start taking a deep look at how we can start rebuilding a world that fits today’s reality. Because of technology, we are living in a world where we have unprecedented power as individuals. Yes, that is terrifying. But it’s also fucking awesome, because it means we all matter and we all have a role to play.

I continue to believe the only way for each of us to start making a difference is through education. Whether this is in K-12, universities, corporate training, online platforms, whatever. A few ideas:

• Educate individuals on how to find, assess, and synthesize what is valid information and what is not.
• Encourage empathy so that we have the discipline and intellectual strength to accommodate the views of others.
• Raise awareness around our inherent biases so we know how to truly listen and learn.
• Create ways that professionals can continually learn new skills, quickly and efficiently, so we can always find jobs.
• Provide access to information about what jobs are available, and what we need to be get them.

The list goes on and on. Everyone needs to play their part, but first they need the tools that empower them to do so.

I am personally dedicated to doing whatever I can to help rebuild the systems that shape our world (not just America). That’s why we created Fresco Capital, where we are investing in the technology transforming these very sectors that need serious upgrades: education technology, work technology, digital healthcare. But that’s just one small part of a much bigger, more important picture of creating a new future.

So… let’s stop whining about this fucking disaster of an election and get started.

Whether it’s the Oscars, the legal system, or hiring practices, diversity is a trending topic of conversation. While I’m excited we’re talking about diversity, the conversation often ends up being both boring and frustrating because it is most often raised in a moral context: “Hire more diverse candidates because you should, because it’s right, because it’s fair.”

In reality, however, I have found that context almost always trumps morals. You might think you know what is the “right” thing to do, but where you live, where you’re from, what your incentives are, who you’re answering to, when you have to answer to them, the opportunity costs — all of these factors convert our sense of “right” and “wrong” into a million shades of grey. So, instead of insisting on a black and white world, let’s acknowledge the spectrum and reframe the conversation.

When it comes to diversity, don’t do what’s right. Do what’s smart. Instead of guilt tripping homogenous organisations and giving out gold stars to anyone who has a “Diversity Initiative”, let’s talk about why anyone who doesn’t is just plain dumb. Diversity is not a moral imperative. It is a business imperative.

The Reality of Bias

As humans, we are hard wired to trust people that are like us. It’s normal. It’s an instinct. It’s a tribal thing. And it makes sense. After all, we are biologically designed to perpetuate our genes. This is why most humans are naturally attracted to people that look like us. Really, look closely at your married friends. It’s kind of creepy.

When it comes to business and we are faced with dealing with another person or entity, smart people want to reduce risk. If you can predict someone’s behaviour, you will have less risk than if you cannot predict their behaviour. If you know what they will do, how they will act, you can prepare accordingly and thus ensure a positive outcome.
Unfortunately, people often prove to be unpredictable. But, we do have the perception that we can control our own behaviour. So, naturally, it follows that if we believe someone is like us, we believe we can more accurately predict their behaviour.

Working with people like you = more predictable = less risk = more control. Boom. I do it, too. I meet someone with an equally terrible Chicago accent, another young American in business in Asia, another Harvard graduate, someone else who wears tortoise shell glasses…. yes, I am instinctually predisposed to like them a little bit more. I’m not going to deny it. Instead, I prefer to acknowledge it, embrace it, and figure out how to turn it into an opportunity.

The Opportunity

As a venture capital fund, there are three key aspects that contribute to our success: sourcing the best deals, adding value to our existing investments, and fundraising. Diversity provides a competitive edge in every part of our business.

1. Source Better Deals

One of the first lessons I learned as a VC is that the worst investment you will ever make is the one you don’t. Our biggest risk is passing on the next Facebook. As such, it is to our benefit to leave no stone unturned, to reduce bias when evaluating investments, to look at every startup as if it could be the next world-changing, billion dollar business.

While I can train myself to reduce my own bias, we’ve already established it is unavoidably embedded in my instincts thanks to millions of years of natural selection, so it might take a while. In the meantime, what I can do is build a team that, collectively, is equally open to all entrepreneurs and technologies.
In addition to our 3 Managing Partners, we also rely on our 3 Venture Partners and our network of 23 Impact Partners to channel quality deal flow. Collectively, our team spans the US, Europe, Asia, Africa, and the Middle East, they have experience in technology, sales, marketing, enterprise, consumer, education and healthcare. They are college dropouts and Ivy League grads. They are Millennials and Baby Boomers. If there is an interesting entrepreneur doing something remarkable somewhere in the world, it is very likely they will look at our team and either know someone, or see themselves in someone.

2. Work More Effectively with Your Teams

The second key element of being a successful VC is working with your portfolio companies to ensure their success. This requires close relationships with founders. Open and authentic communication allows us to stay ahead of potential roadblocks, to properly leverage our network and our resources, and to make high quality connections that help our teams grow their businesses.

We invest in all types of founders — approximately 50% of our portfolio companies are co-founded or run by women. We have teams based in Canada, the US, Europe, and Asia. We work with experienced entrepreneurs, as well as first-time founders. Each founder has a unique chip on their shoulder, has their own communication style, and thus naturally connects with different types of people. Because we have a diverse team, founders tend to gravitate toward one of us, and thus are more likely to be open with us, to ask for help, to raise potential issues as they arise. This gives us a significant edge in terms of our ability to add value to our investments.

3. Raise More Money

As an emerging VC fund, we are constantly fundraising. Similar to what we experience as investors ourselves, our Limited Partners (LPs) want to mitigate risk by building trust with our team. Our LPs include family offices, corporates, and individuals from all around the globe. Canadians, Americans, Indians, Brits, Japanese, Chinese, ex-financiers, young entrepreneurs, family offices and 100+ year old corporations. While we have delivered, and will continue to deliver exciting returns, the reality is that investors write you a check because they trust you. And we trust people who are like us.

Sometimes, when we meet with potential investors, I don’t say a word. They take one look at me, make their assumptions, and only want to hear from my male partners. Other times, I get all the eye contact, and end up speaking the entire time. It just depends on what they’re looking for, what they care about, and who they are more inclined to trust. I can’t change what an investor wants or trusts (though believe me, sometimes, I would like to). However, if we have a diverse team, we are more likely to be able to connect with any given investor. Which means we have more opportunities to raise capital, which makes us more successful in the long run.

Don’t Be Dumb

At the end of the day, I do believe diversity and equal opportunity are the right thing to do. However, as a realist, I acknowledge that doing what is “right” is often not enough. We have a diverse team because it gives us a significant edge in every part of our business.

Even if you’re not an investor, chances are you’re still looking for innovative new ideas and fresh insight into how you need to evolve to grow revenue and avoid disruption. In order to that, you need to understand your customers and attract the best talent, and having a diverse team helps you do both of those things.
Build a diverse team not because you want people to think you’re “good”, you’re “right”, or you’re “progressive”. That’s bullshit. Build a diverse team because it gives you an edge. Because it’s the smart thing the do.

There has been an explosion of hardware startups over the past few years led by the Maker Movement and startup programs like Hax (where I’m an advisor). I’ve seen and worked with well over 100 hardware companies in the past five years. In that time, I have observed that hardware startups think differently than software startups. They shouldn’t. All hardware companies are software companies. The sooner they realize it, the sooner they’ll become successful.

Look at today’s most successful hardware companies. Apple and Tesla build amazing, innovative hardware. And at its heart, a Tesla is an iPad on wheels.

It’s okay if you don’t believe me. But I just upgraded to version 7.1 of their software, which includes self-parking and summon features. It means my car self-drives in parking lots. It’s not even software in disguise. It’s just software. They didn’t send me any new hardware, just an update over WiFi.

Software isn’t Second Priority

It’s tied for first. Obviously a hardware company needs an amazing design and has to worry about manufacturing. The economics of a hardware startup are different. But a great hardware solution needs great software.

If you were going to build the connected camera (as if your iPhone didn’t suffice), designing and engineering a perfect, beautiful camera wouldn’t be enough. People want to frame their pictures, or share them online. Your camera has to have a user-friendly social element or you’ve missed the boat. And if you don’t want to design your own social software, it needs to integrate deeply with Instagram, Facebook, and Twitter.

People, including me, are spoiled. We expect a great software experience wherever we go. If you’re building an IoT product, it’s not enough to connect something to the internet. Users need utility from your software too.

Software can never be an afterthought.

This area is where hardware companies miss out. If they don’t prioritize software, they’ll be unsuccessful. I saw this happen with a company in the pet space. After their successful Kickstarter campaign, they delivered an awesome hardware solution with so-so software. Once they upgraded their software and then built an app that augmented the experience, they were able to draw in new users to their hardware as well as keep the existing customers who purchased their hardware more engaged. Lastly, the additional software opened up way more monetization opportunities besides the hardware. (Nobody besides Apple makes money on hardware.) Only once the company realized that software was the key ingredient did their hardware solution become successful.

What Separates Leaders from Followers

Most fitness trackers do the same thing. They count steps, measure progress, and suggest goals. But if you use a tracking device, I’ll bet it’s a Fitbit.

It should be. Fitbit has the best solution for helping you stay fit and lose weight. It’s simple to compete against your friends (and yourself) as you work towards fitness goals. I find myself walking more so I can catch up with my competitive friends. I take particular pleasure (and taunt them) when I beat my friends on the the leaderboard.

Products are supposed to get a particular job done. The job isn’t to count steps, or else there’d be little distinction between the trackers. Fitbit has invested time, energy, and resources into building a data analytics solution to solve the real job: helping people lose weight. And why are they so successful? Because they invested in software that accompanies their hardware.

In my experience, I’ve never invested in a hardware company. I’ve only invested in hardware or IoT companies that are software or big data companies in disguise. It’s a massive differentiator.

Hardware’s Maturation

Consider this: Intel, a global hardware leader, has more software developers than Facebook. Intel is a software company that happens to produce hardware.

If it’s good enough for world-shaking market leaders, it’s good enough for your hardware startup. Go become a software company as well.

Here in Silicon Valley, it is commonly said that it is “easy” to $1m in seed funding and $100m in Series C/D growth funding, but impossible to raise the $5-7m in Series A funding. This has been called the Series A Gap, or the lack of funds for startups looking to break out of angel and seed funding.

There is no Series A Gap

Over the past year as a VC in Silicon Valley, I’ve worked with Fresco’s portfolio companies and met countless other startups looking for funding. I’ve seen good companies left for dead when trying to raise a Series A and some raise a Series A in just a few weeks. I’ve rolled up my sleeves and worked with the founders on their deck, valuation, strategy, and ultimately their pitch. Along the way in the trenches of Series A fundraising, I’ve learned something: there is no Series A Gap.

Pitchbook and other sources have confirmed what my gut has been saying for the past year: there has been a modest rise of Series A capital over the past few years, but there is a glut of seed funding in the market today-as much as 4x higher in the past 5 years. So it is comparatively easy to raise a Seed round creating more and more startups looking for the same amount of Series A funding.

Startups have little problem raising seed funds these days. They string together $500k-$2m from many different people on an open source convertible note, typically $100k at a time. (AKA the “Party Round.”) Then they go out and try to find the right product-market fit and business model. Some make it and go on to raise a Series A pretty quickly. Most do not.

The Rise of the Second Seed Round

The companies that don’t find the product market fit or develop their business model try for a Series A and fail. Typically they are competing against companies that have already found their business model and are executing against it. Eventually they run out of money.

If you run out of money during your seed round and you can’t raise a Series A, in the past you had three choices:

1. Fold the business
2. Raise a “down” round
3. Keep struggling along on nights and weekends

Now what founders are doing is going out and getting a second seed round. Typically more money than the first seed and almost always at a much higher valuation. Some people call these rounds “pre-A” and “super seed.” I’ve seen a ton of them, some that should be a down round but have a crazy high valuation. (I’ve walked away from two of them in the past month alone.)

For example consider this funding for startup NewCo;

• Angel funding $200k @ $2m cap
• Seed funding $1.3m @ $7m cap
• Seed funding II $2.2m @ $12m cap

NewCo now has 20 or more note holders and an insane valuation. If you have a $12m cap on your convertible note and you raised $2.2m on it, chances are your valuation at the Series A will be near $30m. The problem is that now your revenue and growth trends have to justify that $30m valuation. Unless the business model is really strong and the company is progressing nicely, raising a Series A will be all but impossible. There is no Series A Gap, but rather a glut of seed funding and a self-inflicted wound of raising too many seed rounds with little or no growth to show for it.

What to Do?

Founders are better off trying to raise one larger seed (with a lead!) and using the round to focus like a laser beam on finding the right product market fit while keeping the burn low. If you need a second seed round, try to keep the valuation under control and have very specific metrics as what you want to accomplish in order to position yourself for an A.