What Does the Near Future of Artificial Intelligence Look Like and What Should I Build?

If you haven’t already read Packy McCormick’s blog post this morning on Attention is All You Need, I highly recommend it.

He always writes with incredible insight, but today’s post is especially important as we think about technology in the next several years and decades to come. Of course, you guessed it – his post is about OpenAI. I want to build on that post and suggest some thoughts on where the best places to build are in light of where OpenAI is positioning itself in the market.

Some context

A few months ago, we saw the launch and rise of ChatGPT, a personal assistant that allows users to ask questions and make requests. ChatGPT is the first product ever to reach 100m users in just a couple of months, an incredible feat that surprised just about everyone. Then, last week, we saw the launch of ChatGPT plugins. With the launch of plugins, users will be able to extend ChatGPT’s capabilities to be able to take actions available across other websites within the ChatGPT interface. 

For example, in the future, within ChatGPT, I ought to be able to ask ChatGPT to: 

  • Text all my Facebook friends a fun made-up song on their respective birthdays
  • Search Kayak for the cheapest premium economy flights to London from San Francisco that serves Haagen Dazs ice cream mid-flight
  • Write a script for me that will re-organize my email inbox, prioritizing my founders first

Months ago, I think we saw all of this functionality coming down the pipe.  But up until recently, I wouldn’t have thought that OpenAI themselves would develop a consumer-facing product to tackle all of this functionality. Like many others, I thought that OpenAI would continue extending their platform to more and more startups and developers to build on top of their technology.

What does this mean for developers?

The crux of the matter is that OpenAI is currently running two strategies right now – a platform strategy and a consumer strategy. 

Examples of the platform strategy include Apple and Zapier. Without developers, Zapier would cease to exist and Apple would be largely useless without any apps on their devices. Although both have created “example apps”, neither company really attempts to build their own consumer-facing applications that compete with their partners’ products. 

Examples of the consumer strategy are companies like Facebook and Twitter. You go to those sites and you generally stay on those sites, scrolling through all their content. And, although both started out with developer platform programs, at this point, both largely have just built all the functionality on their sites.

No site can be perfectly labeled a platform strategy or a consumer strategy. E.g One could argue that Apple created Numbers, which is a consumer-facing application, but let’s be real, who uses Numbers? 🙂 

And in fact, running both a platform and a consumer strategy simultaneously is challenging. As Packy mentions in his post:

“All of that is if OpenAI decides to play nice with its partners. If OpenAI optimizes for its ChatGPT users, though, it’s going to disintermediate a ton of businesses and force them into changing how they operate.

In fact, an example of a company that struggles with trying to run both a platform strategy and consumer strategy is Amazon. 

Amazon started out as a platform for e-commerce stores to build on top of. I have friends who run online stores who initially hopped on Amazon and reaped the benefits of their logistics support, distribution reach, among many other helpful features. 

But you may have noticed that Amazon also now sells their own end products – everything from shoes to paper shredders. And their products are GREAT. One of my friends who runs an online store found that at first, it was hugely beneficial to her business to be on Amazon, but eventually, Amazon came out with an identical clone of her products, utilizing all the data from their Amazon presence to know that she was making bank, and Amazon wanted a piece of that action. 

Needless to say, my friend knew she wouldn’t win on Amazon, so she left their platform. And her store continues to grow and thrive as an independent site. In many ways, Shopify exists as the platform strategy in this space to challenge the power of Amazon and provide an alternative for e-commerce stores as Amazon adopts more and more of a consumer-facing strategy.

This brings us back to OpenAI – if there’s even an outside chance developers think OpenAI will copy them and integrate their functionality into ChatGPT, then top developers won’t want to partner with them. This creates a large opening for a potential competitor to truly go after the platform strategy. But said competitor will have to move quickly AND will need to reassure developers that they will not launch consumer-facing offerings that will compete with their own partners.

In many ways, one might be wondering how OpenAI ended up in this situation of pursuing two conflicting strategies. Pure speculation here, but I can see how one might like to start w/ the platform strategy. But, in launching ChatGPT – perhaps initially just as an example app – much like how Numbers is an example app, they may have been as surprised by their fast and impressive distribution success. And if you’re able to attract 100m users that quickly, then it only makes sense to double-down on the consumer strategy and ditch the platform strategy. Afterall, owning the end user experience and being the brand that a consumer remembers is the preferred strategy here if you can pull it off. It allows you to compete with Google and just about every destination site on the internet. It only makes sense for them to switch strategies at this point.

So who ends up serving developers?

There are certainly a lot of would-be OpenAI competitors looming around, but right now, it’s not clear to me who will move into this opening that OpenAI is creating. This will be a land grab to own the platform strategy in the AI space. Platform strategies often have one of two things that partner companies gravitate toward: 1) Distribution and 2) Technology. 

For the former, we’ve talked about why people build on Apple or sell on Amazon – clearly distribution. In this case, a would-be competitor to OpenAI would have to offer strong technology. 

An analogous example that comes to mind here is TSMC. TSMC is arguably the best contract chip designer and manufacturer in the world. Although most people think that being in the semiconductor chip business is a horrible commoditized business, TSMC has margins upwards of near 50%! If you’re competing on technology utilizing a platform-strategy, you’d better be #1 or perhaps #2 in technology, because if you are #8, your tech largely is a commodity. 

technology computer lines board
Photo by Pixabay on Pexels.com

TSMC manages to generate these kinds of margins, because they can produce very tiny chips, which means that phones and computers can cram in more chips into a limited amount of space for more computing power for their devices. Unlike in a consumer-facing strategy, no one cares if your chips are more user friendly or look nice or you have better customer support. The only thing that matters with this strategy is that you have superior technical specs. TSMC has continued to be the market leader over the decades, because they continue to reinvest vast amounts of profits and capital into staying the leader in this market.

This is what it will take to win the platform strategy in AI. Strong technology is a starting point but continued betterment is equally important to maintain the lead. And in AI, how do you come out with better and better models? By amassing more and more data. 

So I think what we may end up seeing here are weird alliances – I could imagine some sort of partnership between websites that have a lot of data and an OpenAI competitor here so that existing large destination sites will not lose to ChatGPT. 

In fact, we’ve seen this movie before. When Apple launched the iPhone, Google rallied around the Open Handset Alliance as a hedge to ensure that Apple would not soak up all the mobile traffic in the world. With this open working group consisting of top mobile carriers and handset makers to support Android, an open source mobile operating system, Google was able to come out with a competitor that they wouldn’t have been able to develop on their own. In a similar vein, when social networks were taking off and Facebook was dominating, Google rallied around Open Social, which was an open source social app SDK with support from many of the top social networking competitors to try to compete with Facebook at that time. 

We will definitely see something similar here – whether it’s through the alliance of various existing players to compete directly with ChatGPT’s vision or a single player attempting to go head-to-head with OpenAI on the developer-strategy much like what Shopify did with Amazon. In the ChatGPT world, you will be able to do everything on their site and in a competing world, you will be able to do much more on all the other sites. Both versions will win, because power is never left unchecked.

So what should I build? 

With the AI world in flux, how should I, as an entrepreneur, navigate this? I think that we should assume that every site in the future will utilize AI to provide a better user experience with greater personalization.

So if you’re trying to build the next AI image creator or the AI trip planner, etc, consider it too competitive already. In fact, Adobe, Canva, etc are all rolling out their generative AI tools within their own existing programs. Even for websites that have terrible tech teams, you should assume there will be an OpenAI competitor who will serve those tech-unsavvy websites to make adding AI to any website really easy. 

In software, distribution often wins, and as such, if I were building a new product, just like at most other points in software history, I would go after the spaces where I either a) had distribution edge already, b) saw an opening where there’s not an existing large player with distribution, or c) had an insight into a uniquely differentiated product in an existing space. And I might partner with an OpenAI competitor that is friendly to developers to ensure OpenAI doesn’t integrate my functionality into ChatGPT.

And if you are building infrastructure in AI, I think the opportunity is now to go after a developer-focused OpenAI competitor. But you need to be #1 and stay #1.

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Leadership during a crisis

Wow. What a week.

I’m sure most of you reading this are in and around startups and already know what I’m referring to. But if not, the most popular bank for startups and VCs called Silicon Valley Bank just went under. They are still getting a final count on what percentage of deposits are not insured, but I’ve seen 97% being floated around. That’s a lot of money potentially gone.

But we’re all tired of hearing about what we think happened or whether a buyer will come along. The much more important thing to talk about is what to do in a crisis situation.

Over-communicate. And then communicate some more.

One of the biggest mistakes I see organizations make during a crisis is their failure to communicate swiftly and with poise. Often organizations want to find all the facts and think about the right words to say. They want to focus on solving the problem.

Unfortunately, this is a big mistake. And it’s a mistake that happens all the time — such as in this crisis with SVB or during COVID or when employee allegations about abuse or harassment emerge, etc. Companies make this mistake over and over again — both big and small companies.

It is important to own your communications and use them to get ahead of a situation that is spiraling downwards. In fact, this is so critical that I’ve spent the last 2 days drafting communications for many of our portfolio companies in figuring out what to tell their investors, business partners, and/or employees yesterday.

It’s not so much about what the comms actually say but how they make people feel. The feeling you want to convey is 1) You got this under control – leadership is on it and ppl can count on you, 2) if you don’t have all the answers, you will get info and will keep people informed as you go along, 3) your door is always open to chat.

If this isn’t done swiftly, even if you are actively working on a solution to a crisis, people will lose faith in you, because they are unaware of the steps you are taking. As such, it is much more important to communicate something — anything — quickly and update your comms as you go along than to try to write the perfect thing 4 days later. The best time to do this is in the first 24 hours of a situation emerging.

So, in this situation, if you haven’t already sent out communications to your employees and investors, I’d highly recommend doing that today. It can be short and sweet:

For investors:

  • You may have heard about SVB (link)
  • We were/weren’t affected and to what extent
  • If affected, we are still trying to learn X and will keep you informed
  • Thank you for your support always

For employees:

  • You may have heard about SVB (link)
  • We were/weren’t affected and to what extent
  • 1 line about payroll – i.e. rest assured, we are actively looking at loan options to make this work (if with SVB) / or we were not affected
  • Business is as usual
  • If you have questions / concerns, my door is always open

As the CEO or head of your org, your job is leadership. This means that communication and morale is your #1 responsibility. I often see CEOs think they are too busy to address the communications during a crisis mode. They are too busy trying to solve the problem. But communications is everything.

In addition, during a crisis, you’ll often see people go above and beyond. It could be from within your company but it may also be through external partners. In a crisis, there are people helping all the time. This is the time to thank them and make them feel extra appreciated.

Over the years, we’ve done this a few ways: we’ve sent food (treats from a grocery store, meals from Doordash, and gift cards to restaurants). We’ve sent alcohol and ridiculous stuffed animals and stupid stuff to make people laugh. It’s just a way to show appreciation and thank people.

Ultimately, your communications with everyone is about saying “I see / hear you. I’m on this situation. I appreciate you.” That is leadership.

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The Return of Camp Hustle

Today is a big day for my team. We’re announcing the return of Camp Hustle.

But first, I want to talk a bit about what is top of mind for me going into the new year. One thing I think deeply about a lot is how can we get a lot more great startups funded.

Part of this answer is through our Hustle Fund pre-seed fund. Part of this answer is through our 1000+ member global angel club called Angel Squad.

But the vast majority of this answer lies in helping more investors — whether they are new VCs or angels — in their journey. We need to help more people jump into the startup-investing game AND become successful.

This effort starts with community — connecting more great budding investors together to level up everyone’s investing through capital, knowledge, and networks.

We started resuming live events last year with Camp Hustle 2022 and we’re back this year to help connect more investors.

My colleague Haley Bryant interviewed Sequoia VC Jess Lee at last year’s Camp Hustle

What is Camp Hustle?

Camp Hustle is an in-person event exclusively for investors. (Now, if you’re a founder, I’ll get to why you may care about this in a minute…hang tight and read on…)

It’s a full day of networking (a lot), talks (a few) and live pitches (with real-time pitch analysis). It’s taking place on May 17, 2023 in the Bay Area.

What’s the point?

We write a lot of free content and throw free online events on startup investing. But I’m also a big believer that attending events where you can meet people to help you level up is life-changing.

The purpose of Camp Hustle is to help you meet other investors.

Why would you want to meet other investors? Well, for starters…

  1. to learn about great companies / improve dealflow
  2. to help your existing portfolio companies by building key connections
  3. to help your own VC fund’s fundraising efforts
  4. to grow your angel investing syndicate
  5. to meet kind, creative, successful investors who love the same things you do

What happens at Camp Hustle?

In addition to structured and unstructured networking opportunities, Camp Hustle will also feature:

  • talks from founders with multi-millions in revenue
  • a Shark Tank-style pitch event
  • small group discussions on hot-button topics
  • ample time to chat with 200 other investors
  • great food (and s’mores)
Shiyan and I kicking off last year’s Camp Hustle

If you’re a founder, do you want to pitch your business at Camp Hustle?

One of the most requested online events that we’ve often done are pitch-feedback events. This year, at Camp Hustle 2023, you can apply to pitch your startup live (by April 15). And if you’re selected, you’ll get to pitch in front of 200 investors and will receive live feedback on your pitch as well.

Let’s get more great startups funded!

I look forward to seeing you at the event. Grab your ticket here and use the code EYLIST to knock down the price. FYI, that discount code expires on Jan 31.

Regardless, I’d love your help in amplifying this so that we can connect more investors to get more great startups funded.

Hope to see you in person at Camp Hustle!

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My first trip to Vietnam

Happy new year!

I’ve been meaning to post this for a while now and my hope is to write more this year.

Last fall, I took a trip to Vietnam, my first time traveling there. I was really impressed with the people and the country! The energy in Ho Chi Minh was incredible. Construction and buildings are popping up left and right. You can feel the rise of the city and the country as a whole. Being there felt a lot like how I remember feeling when I visited China in 2005. The excitement of fast growth. It’s so hard to believe that this was the same country that the US left in shambles less than 50 years ago. In fact, while the US is suffering from inflation and declining growth, Vietnam’s inflation today is only ~3% and their GDP is expected to grow 6-8% per year in the near term. Remarkable.

We took our Hustle Fund team there because, we have invested in a LOT of startups in Vietnam, almost all of whom we invested in via video conference — even pre-pandemic! In meeting many of our founders for the first time, I was really impressed with the level of passion and hustle. And what so many of them have achieved with their companies in such a short period of time is mindblowing.

Celebrating Eric’s birthday w/ our portfolio founders at CTY Kitchen, which had great food and is owned by one of our founders (check it out in Ho Chi Minh!)

Vietnam reminded me of why we invest in so many companies in emerging markets. My trip reinforced my belief that growth is so much faster in green field markets. Although ⅔ of our startups are still going after the United States market, the myriad of opportunities in emerging markets to build huge companies is so much larger.

A lot of our portfolio companies in Vietnam are on a tear. And, one such company whom we visited was Dat Bike, an electric motor bike company. The founder Son Nguyen, has an amazing story and background. He grew up in a beach town called Da Nang and was able to get scholarships to study computer science in the United States. After graduation, he worked as a software engineer in the US, but he always felt like there was something he could be doing for his home country. He realize that in Vietnam (which has ~100 million people) most people ride motorbikes, but few people ride electric motorbikes. Existing specs for electric motorbikes are too poor (not enough power and not enough distance at the right price). So he decided to start an electric bike company to make Vietnam greener.

Our team visiting Dat Bike and gearing up to ride

But Son didn’t actually know anything about electrical engineering or building a motorbike! So he learned everything he could on YouTube in order to build his first prototype!

Then he also convinced two of his American friends to move from Silicon Valley to Vietnam with him to build this company even though neither had roots in or any connection to Vietnam. He debuted his bike on a Shark Tank-equivalent show in Vietnam from which he was able to find supplier-contacts and future hires for the company. Today, they employ hundreds of people, and they are just getting started. You can see their bikes on the road when you visit Vietnam.

Janel, Jamie, and Chloe gearing up to ride in the streets of Ho Chi Minh

The bike is so smooth and quiet. In part, it’s because they threw all design assumptions out the window and started from first principles in building a new bike for the Vietnamese market from the ground up.

Maybe not the smartest decision to ride an electric motorbike in the rain with flip flops

Founding stories like Son’s — and most of our founders — is why I feel so privileged and lucky to be able to invest in inspiring startups.

Beyond meeting with our portfolio founders and potential investors / co-investors in Vietnam, in true Hustle Fund form – we also got everyone outside hiking during a torrential rain storm to see a totally different perspective of Vietnam.

Part of the Hustle Fund team from a lookout on a mountain completely drenched

I always love traveling with the Hustle Fund team. But, Vietnam was particularly fantastic — the entrepreneurial spirit, the startup community in Ho Chi Minh, the countryside, and the FOOD! I’m excited to see how things have changed in another five years.

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Happy 5th birthday Hustle Fund!

Wow, it’s hard to believe it’s been 5 years since we started Hustle Fund! In the last 5 years, we have: 

  • Raised and deployed ~$130m
  • Brought on 25 team members at Hustle Fund
  • Built a community of nearly ~1000 Angel Squad members
  • Funded ~400 portfolio companies
  • Worked with ~300 LPs
  • Grown to 100k+ followers on my Twitter acct

I’ll let you know how it’s going in about another 5 years! 😀

For all of this, I am so grateful. All that we have achieved has been a community team effort. Hustle Fund is so much more than a VC fund. It has become a movement.

I say this because movements are about values. Movements are about being mission-aligned. When we started Hustle Fund, we didn’t set out to build a VC fund per se. We set out to solve a problem that we personally understood well that we could work on solving over the rest of our careers of 30+ years. The mission that we are on is to democratize wealth via startups by helping startups with capital, knowledge, and networks.

In our first inning of Hustle Fund, we focused just on the capital problem. Specifically, how can we help more fantastic startups who may not have a rich uncle get capital at the pre-revenue stage? Without a warm intro and without needing to be in Silicon Valley. 

This is the hardest stage to raise money, and five years ago, there were only a handful of VCs addressing this stage. Fast forward to today, we have raised 3 funds. The latest one we are announcing today is a $46m fund to continue to address the pre-seed stage.

But perhaps, something I’m even more proud of is the informal influence we’ve had on so many other funds and angels who now invest at pre-seed, especially those who are willing to make a bet on founders they don’t know. Pre-seed funding is far from being solved, but I’m proud of the work we have done — the work we all have done — in making a dent in this problem in just the last 5 years. And, we will all continue to keep working on improving capital at this pre-seed stage.

Giving thanks

I’m particularly thankful to our LPs and founders. It took us 700+ meetings to raise our Fund 1, and I will never forget those early believers. Thank you for saying yes to us. Without you – literally without our founders and LPs – we would not be here. We have been so fortunate to be able to work with a ton of amazing founders around the globe.

When Eric and I started Hustle Fund, we thought that we might just form a small team of people in the Bay Area. That idea went out the window immediately when we realized we really wanted to bring Shiyan onto the team (and she was moving back to Singapore)! From there, we have recruited a phenomenal team of entrepreneurial, sharp, and also kind people. Special thanks to Jason, Thenuka, George, Kera, Tam, Haley, Will, Lidia, Chloe, Hung, Susan, Ha, Brian, Janel, Jamie, Nicole, Kabe, Andy, Todd, EJ, Erica, Mike, Jasmin, Maria, Karuna, Melanie, Amelia, Audrey, Anthony, Kenn, Davyn, Joseph, Wilson, Christine, Cjin and Chels for getting this off the ground. There was very little reason to join this ship when it was just a dream, so thank you for joining.

One of my early lessons in starting a company years ago was that you don’t start a company with a co-founder. You start a company with a co-founder AND his/her entire family. Thank you Eric and Shiyan — I couldn’t have asked for better co-founders in this journey. And, also to our families, too, who have been so patient and supportive of us. Special thanks to B, K, and JJJS who aren’t in the limelight but have been so critical to Hustle Fund becoming reality.

The next inning of Hustle Fund that we started last year was to address capital in other ways as well as to make an impact on spreading startup knowledge and increasing networking opportunities for great founders. While my partners and I have been focused on our fund, last January, Brian Nichols, who is the General Manager for Angel Squad assembled an amazing community of angel investors from all over the world. Many of these wonderful people were completely new to angel investing, bringing new capital and expertise into startup ecosystems. These people come from large tech companies and their own startups but also many other professions. We have doctors, lawyers, professional athletes, a poker player, a professional chef, and many other occupations represented from all over the globe. This diverse group of nearly 1000 angel investors are active, engaged, and want to help startups. They move quickly, are smart, and have conviction. I’m biased, but this is probably the best angel investing community you will find anywhere — all because of the amazing, humble, and kind angel investors who have joined. I’m so proud of this community because of who the people are.

What has surprised me most about Angel Squad is though it’s less than 2 years old, they have deployed way more capital than our Fund 1! So while many people are fixated on trying to raise VC funds or raise money from VC funds, sometimes the better solution to mobilize capital is by empowering angel investors and cultivating new ones. There is so much money in the world — it just needs to be catalyzed. Beyond capital, I am also thankful that many people within Angel Squad have provided our startups with valuable advice in areas like design, engineering, hiring, sales, and business development. I’m floored and thankful that there are such helpful people in the world who are so generous with their time.

Beyond Angel Squad, we’ve also been partnering with other General Managers on our team who have launched initiatives that are also trying to make a big impact on capital, knowledge, and networks in startups in other ways. More to come. The next few years will be exciting.

I think many people think that being a VC is easy. But, truth be told, being an emerging fund manager is akin to starting a company. You have to raise money with nothing to show. And you have to market yourself like crazy. In the last 5 years, in order to get to this point, we’ve burned the midnight oil so many nights. But if effecting change were easy, it wouldn’t be worth doing. So for those of you who have “hustled hard” on a startup or a new fund, I see you. I know it’s a tough road of ups and downs (and honestly, mostly downs). But, if you cut out all the noise of who is becoming a unicorn or who raised what funding and really dig deep as to why you’re doing what you do, I hope you find the courage to keep going and wish you tremendous success.

It has been a privilege and a dream to be able to do this work and work on a mission that means a lot to mean, and I look forward to the next 25 years. Thank you so much, Hustle Fund fam!

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Some reflections on turning 40

Last week, I celebrated my 40th birthday with my family (which is pretty amusing since my birthday was last November).

When I think back about the last few decades, a few stories from my professional life come to mind that I thought I would share here.

1) Serendipity and luck trump everything.

Certainly hard work and skills are important, but luck and being at the right place at the right time is so critical.

I wasn’t born into a family of entrepreneurs or even tech. I got into startups, because of a couple of key events that happened to me. One event that got me into startups happened in 1996 growing up in the SF Bay Area during my freshman year of high school. My best friend Jennifer told me one day that her cousin Tony was building an internet startup. And she asked me if I wanted to help him and their startup over winter break. I didn’t know what a startup was, but I also had nothing major going on during winter break. So, we took the Caltrain up to San Francisco to “help” Tony. When we showed up, the place was honestly a bit of a mess and chaotic. But it was exciting! Tony and his friends were working together on all kinds of projects. They didn’t have to dress up in “grownup-work-clothing”. And they could eat all the pizza they wanted. It was the dream.

I wasn’t any help to their company. But I knew from that day on, *that* was what I wanted to do when I grew up. I didn’t even know how they made money or that there was even money to be made. But, even from that early day, it was inspiring to see a group of friends come together to build something bigger than themselves. A couple years later that company LinkExchange was acquired by Microsoft for a reported ~$200m. Tony — who was Tony Hsieh — would go on to become an active angel investor in many startups and become CEO of Zappos. And while I didn’t know it that day, he would also later have a bigger impact on my life as well as my startup LaunchBit and Hustle Fund, as I’ve written about before here. I’m incredibly grateful for the path he set me on, and that was entirely serendipitous.

2) Failure leads to success.

One of the things I’ve noticed is that most successful people have had *a lot* of failures as well. But people only talk about the successes.

For me, failure and success are oddly connected. When I was nearing the end of college, I thought I wanted to go to business school, and I applied to a few business schools in the fall of my senior year. Throughout this process, I had wanted to visit a couple of business schools I was applying to in Boston, but my money was tight, and I didn’t want to pay for a plane ticket to Boston from California.

Coincidentally, around that time, I saw an ad for a contest, in which the prize was a free trip to Boston from anywhere in the US. I immediately entered the contest on a whim, and amazingly, I won!

The contest was sponsored by the DISCO career forum, which was/is one of the largest job fairs for jobs in Japan. And oddly enough, it was and still is held in Boston every year. In fact, at the job fair, I met tons of people from Japan who flew to Boston just to apply for jobs back home!

I didn’t care about the job fair. I was merely excited to fly to Boston, see my friends, and visit a couple of schools for a couple of days. But, in order to get my reimbursement for my plane ticket, I had to attend the DISCO career forum for 2 days. While there, I met a ton of companies and even interviewed on the spot for various jobs. Although I wasn’t actually looking for a job, by the end of the weekend, I got a job offer!

I soon learned that I didn’t get accepted into any business school, but at this point, I was very excited about the job offer I received and accepted it.

About a year later, I packed my bags and moved to Tokyo. But, a month into it, I was told that I couldn’t stay in that role, because my Japanese was not good enough. Wow, was I getting fired? After just a month into my first job?? That night, I sobbed my eyes out.

To their credit, my former employer was extremely helpful in this situation. They gave me a few choices and told me that I could still stay at the company for about a year if I moved into marketing (so that I wouldn’t have to talk with customers with my poor Japanese 🙂 ). But they didn’t have budget to pay for me much beyond that, so I had to find something else to do.

I decided to re-apply to business school. But this time, I only had time to apply to one school – so I chose to re-apply to MIT which was the school I liked best after visiting. And, fortunately, the entire application was the same except for one question: “What have you done in the last year?” a topic on which I had a lot to say from my experiences in working in Japan. A mere few weeks later, I received an email saying there was a decision ready. I had not even received an opportunity interview this time, so I was pretty certain it was a fast rejection, but it turns out, I had gotten in!

Looking back, failure and success were so well coupled together. I failed to get into business school so I got a job. I failed to keep the job, so I went to business school.

3) Frugality and portfolio construction are keys to wealth. Wealth is freedom. 

I am a huge fan of the FIRE (Financial Independence, Retire Early) movement and was an avid reader of Mr. Money Mustache. I think when most people aspire to become wealthy, they think they need to be super successful with building a hit company or something like that so that they can buy all the stuff they want.

In truth, when you get there, many people realize that the stuff isn’t interesting. Wealth is about the ability to be free. Free from ever having to work at a job or on a project you don’t like again. Free from feeling pressure to work with bad people. Free to work on the things you do actually like or find worthwhile. Free to spend your time however you like. 

And it actually doesn’t take a life-changing event to become wealthy. Even if you never have a hit company, you can still become wealthy — with frugality and strategic investing. 

In my 20s, I quit my job to start a company. My husband was a post-doc (read: paid pretty much nothing). I took odd and end gigs to make ends meet and scrimped like crazy. This was pre-gig-economy, so random jobs I did included being followed around by a researcher from Xerox Parc, categorizing whiskeys, and critiquing MBA resumes for international students. I remember on the rare occasion we would go out to eat, I would get very nervous if we exceeded spending $25 in total. 

In looking back on that, most people – especially in my peer group of tech friends – think about $25 as “Oh, it’s just $25.” I have many friends who believe that saving $6 here and there on SBUX lattes and avocado toast is meaningless. It’s just $6. And as a millennial, I do believe there are systemic issues with our financial system and incentives, I also do believe that investing the equivalent of one latte a day can make you a millionaire.

The right way to think about spending decisions is in its compounded value. You take $6 a day and throw on a 7% annual interest rate in the public stock market or 12% annual rate or higher(!) in the private markets. That $6 daily latte is actually worth over $350k+ in your 40s if you take the money and invest it. Just from *investing* your latte money daily, your average person who invests in standard index funds available to everyone and lives an average lifespan *will become a millionaire*.

That’s pretty remarkable. 

But I think the topic of portfolio construction for investments is incredibly confusing. And frankly speaking, I think most people find the topic boring and honestly scary – you could lose all your money! Loss aversion is probably one of the biggest roadblocks to more people investing – even in index funds.

I, too, have thought for many years that investing was scary. But I read somewhere when I was very young that putting your money in a savings account actually *loses* you money due to inflation (which today stands at 8%+ annually!). And, I have been investing in index funds ever since my first job in high school. In other words, I was motivated to invest by the idea that I was losing money by merely saving it!

Now at 40, and having seen even some of the meager earnings I had in my teens compound, I still believe index funds are a fantastic place to put your money. You can passively compound and grow it reliably, because it’s diversified and rides on the economic growth of the world.

But, the one thing I do regret about my investment choices was not investing earlier in *private markets*. I didn’t know anything about investing in startups until the last few years. In fact, for many years, the thought had never even crossed my mind to become an angel investor. I always thought you needed to be super loaded to do that.

And then when I was in my 30s, one of my entrepreneur-friends, who at the time had not yet had an exit, told me that he had been angel-investing into friends’ startups with $1k each. This surprised me. How could you invest $1k checks into startups? Why would anyone take that kind of money? I also didn’t understand how he was accredited to be able to do this (I have since learned that his own startup was valued above a certain amount, and his net worth on paper made him accredited). The world of startup investing was utterly unfamiliar to me even though I was a founder myself at the time!

And, it was very inaccessible — there was no information online anywhere on how to get into any of this. Friends learned from friends how to angel invest. I had wished there were an accessible way to get into small check startup investing once I had some level of a portfolio with my index fund investing. I wanted to be able to add some additional risk/higher reward to my portfolio in an educated and balanced way.

And, this is why my colleague Brian Nichols started a program called Angel Squad at Hustle Fund – to empower small angel investors to learn, invest alongside us for even as small as $1k checks, and network with each other as they start and further their angel investing endeavors. We now have almost 1000 angel investors in this community and the next cohort beings soon if you want to apply to join Angel Squad.

4) Family balance is challenging. Take all the help you can get. 

Being an entrepreneur is about doing a lot of sprints while running a marathon. I think the only way I’ve made things work is to rely a lot on help and to not attempt or even care about perfection.

How my child perceives me. I would love a gravity-defying computer like that.

Throughout the pandemic, things were tough for just about everyone. I remember this one day that summed up my life: my husband was working at his lab. I had tons of back-to-back meetings as sh*t hit the fan with everything. My older child who didn’t know how to use a computer needed help logging on to an online class. And my younger one wasn’t quite potty trained and had just pooped on the floor and then stepped in it and ran around from room to room. All at the same time. 

After that happened, my parents who live a few miles away from me, so graciously offered to take the kids to live with them for the *next several months*. That was huge. And I’m incredibly grateful. I don’t know how we would’ve pulled through without that help.

I recently listened to Indra Nooyi’s memoir My Life in Full: Work, Family, and Our Future about how her career progressed through Pepsi, and the multi-generational help she received from family resonated with me. As much as we’ve progressed and moved forward with society, there’s still a lot of burdens or asks that fall on the mom. Don’t get me wrong, I think my husband is a phenomenal dad, and many of my friends are amazing dads as well. Many dads do so much for their kids and childcare these days.

But society still puts a lot of little burdens on moms in unsuspecting ways. And, it’s the little things that add up. For example, during the pandemic, some of the moms in my kid’s class sent out emails asking folks to submit a page for the school yearbook. Thinking those were mass emails, I just completely ignored them. Eventually, those emails turned into a personal one sent directly to me.

You can bet my husband never received those emails even though he is on the parent list and certainly didn’t receive the direct personal one. I politely responded that unfortunately I didn’t have the bandwidth to do a class yearbook page for my first grader. (I mean…who does a yearbook page for first grade??) You might think, “well, it’s just someone asking you to do a yearbook page – sheesh. No biggie.” But it’s all the hundreds of little requests that happen everyday that compound and particularly on moms.

My child created this sign for my office

As it turned out, the mother who emailed me ended up taking on the task to do the yearbook page *herself* for my first grader. I never saw the yearbook page, because I didn’t order the school yearbook (see #3 on frugality). (Also, did anything interesting even happen during the remote school year?)  

Family balance continues to be a struggle, and honestly, I think this is an area that is still being pioneered. After years of getting unhelpful advice from people who have never been in a similar situation before, I think I’ve learned to just embrace the situation. You do the best you can. And that’s ok. Say yes to help. It will work out.

5) Adventures spark inspiration. Routine makes you better. There’s a balance.

Because I grew up the SF Bay Area my whole life, after college graduation, I decided I would go far far away. Even though I knew I wanted to start a company someday, I first wanted to see the world (on someone else’s dime of course — see point #3 on frugality).

So, I left the Bay Area in 2004. I interned at CERN in Switzerland. I worked in Japan in the middle of nowhere (in a town called Suwa in the Nagano prefecture) and also in downtown Tokyo (see point #2 on basically getting fired). I interned in India at Infosys. I briefly worked on a project in New Zealand. I did everything I could to not come back to the Bay Area (until I had my first kid). 

Although none of these trips were for the purpose of entrepreneurship or starting a business, oddly enough, I ended up meeting so many people who would end up becoming successful entrepreneurs. For example, in my intern group in India, one person noticed that a lot of food was served on leaves there. He later started a company in the US to make high end disposable plates made out of leaves, and that company is doing really well. 

I often hear that one of the best ways to figure out how to start a company is by working at other startups or by trying lots of different business ideas. That certainly is one path. But, sometimes, I think the most off-the-beaten path ideas — the ones with most opportunity — are where others are not looking. And that means also exploring or being an adventurer in paths that others are not taking. 

That could mean pursuing an unusual career path. Or living somewhere others are not.

I have been investing in global companies for the past several years now, and while I’m no expert in any and all problems, many of the problems that international entrepreneurs describe to me — at least on some level — are familiar because of my time abroad.

At the same time, running around from place to place and going from one new project to another has its limits. Entrepreneurial skills are honed by doing the same boring thing day in and day out. Just like practicing a sport or a musical instrument, it’s the repetitive mundane that makes you get better. And of course your role changes as your company grows — going from individual contributor to manager to CEO of a large company. But, working on the same problem day in and day out is mundane to many people. And to grow something big is work across a decade or more by doing the same mundane thing better and better everyday.

My thinking about entrepreneurship changed after my company LaunchBit was acquired by BuySellAds in 2014. The CEO and co-founder Todd Garland bootstrapped BuySellAds, and they have quietly become a behemoth. They have grown their ad network tremendously, and they answer to no one. Approaching 15 years, they just continue to hone their supply side and demand side, and that’s how you grow — there are no shortcuts to honing your skills year in and year out. 

Most people, including my younger self, don’t have the discipline to do that. But after many years of doing the same thing over and over, eventually you get really good, and a business does well enough to become really exciting. And BuySellAds has been able to push into new initiatives while keeping their cash cow afloat. They’ve gone into other areas beyond ads, building out a portfolio of other businesses, working with great people. This is the kind of stuff you can do when you own your own destiny and don’t need to answer to investors. And it’s the kind of thing you can do when you’ve got a flywheel going. I’m convinced Todd will be one of the first bootstrapped billionaires — AND most people probably won’t ever know it. 

I think too many entrepreneurs, including my younger myself, are enamored with getting acquired, because they don’t have the patience and the fortitude to do the same thing day in and day out. (And as a VC, of course, I like exits too). But, as trite as this may sound — my lesson from BuySellAds is that the journey is the reward. Getting better at honing your skills everyday is the goal. Being able to do cool stuff with cool people, work on interesting problems, and make money *is* the dream. 

I probably have about 30 — if I’m lucky 40 — good working years left. And, Hustle Fund is my last job. Our mission at Hustle Fund is to democratize wealth via startups by increasing capital, knowledge, and networks in startup ecosystems everywhere. It’s a company I won’t ever sell, because it’s what I want to work on forever. And though not everyday is easy in building Hustle Fund, over the years, I’ve learned to thoroughly enjoy the entrepreneurial journey of embracing all the ups and downs. It’s a joy and a privilege to be able to work on this problem with an amazing team. 

These are just a handful of learnings I’ve had over the last couple of decades. I look forward to learning so much more between now and age 50. 

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