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. 

Speaking up about sexual harassment is hard. But we must start a new chapter.

Disclaimer: Like with everything else on my blog, these opinions are solely mine and are not representative of my employer. 

Like everyone else in the startup world, I read this story about Justin Caldbeck with both curiosity and disgust when it went viral on Thursday. Since then, many VCs, startup founders, and reporters have called his behavior appalling. And make no mistake, his behavior is extremely appalling and inappropriate.

At the same time, this story was not at all surprising to me. In fact, I’d heard about Justin’s reputation over six years ago through the founder grapevine — when I, myself, was a founder. While I didn’t know at the time whom he made inappropriate advances towards, I did hear from other female founders to be careful. Founders do talk; you hear about which investors have a bad reputation for inappropriate behavior. In other words: there have been a non-zero number of people who have known about Justin’s behavior and have not called this out for several years.

Victims and bystanders have a difficult time coming forward to report cases of sexual harassment because there are often limited penalties for the harasser. Given the track record of the tech and startup world so far, victims have reason to believe that nothing will be done about such behavior and that they only have everything to lose by reporting it. In many cases, victims risk societal repercussions, including lack of support from their colleagues who don’t want or care to involve themselves, being told they are exaggerating, that this is normal, and to stop complaining. Worse yet, victims have to put their sense of safety and future employability on the line, especially if their names end up being smeared publicly. Even HR departments that are charted with the responsibility of helping victims may have conflicts of interest and may not actually be helpful. For all these reasons and more, all too often, sexual harassment cases go unreported, and this becomes accepted as par for the course. When this cycle happens over and over again, it can be hard to see just how disturbing and messed up this is. So huge props to Niniane Wang, Susan Ho, Leiti Hsu, and others for their courage in coming forward to publicly report what happened to them, in spite of challenges by Caldbeck himself. Their actions help us as a community right our moral compass.

Their bravery has also paved the way for more stories like this to come out of the woodwork. My friend and freshman dormmate who was previously an entrepreneur recently posted to Facebook publicly about specific advances a couple of other VCs had made on her about a decade ago when she was fundraising for her company. I respect the courage it took for her to come forward with something so personal and specific. There need to be real consequences for sexual harassment, and that only starts when victims are able to come forward with their stories.

We have a real and undeniable problem here in Silicon Valley with sexual harassment. While the perpetrators themselves are to blame, the truth is, the rest of us are also part of the problem — myself included.

A few of my friends have been victims of sexual harassment. While I’ve been empathetic, I’ve never really pushed any of them hard to come forward with their stories. Knowing that reporting sexual harassment is fraught with so many difficulties for victims (as mentioned above), I’ve largely been a useless bystander, believing that victims should really just decide on their own whether they want to take personal risk in reporting their cases. A few weeks ago, one of my friends who was a victim of sexual harassment told me that it was very difficult to come forward with her story on her own. Although she eventually reported what happened to her, she said that she wished I had been more proactive in encouraging her to come forward.  The unconditional support of friends, colleagues, and managers is so clutch in helping sexual harassment victims find courage to come forward.

And she’s right. It isn’t enough for us to be empathetic and passive. It isn’t enough for all of us to go on Twitter and say, “I won’t behave like this.” I encourage you all to also commit to proactively helping and pushing victims to come forward. In particular, people who are in positions of power — especially managers and investors — are in even more of a position to be able to help, even if they are not the victim’s direct manager or investor. It could mean taking Reid Hoffman’s “Decency Pledge.” It could mean committing to particular actions that you’ll do the next time you hear about sexual harassment in your line of work.

As I challenge all of you to think about what you can concretely do, here’s what I can concretely do to help eliminate sexual harassment and inappropriate behavior in the startup world:

  • For the founders I back and have backed, if other investors have acted inappropriately towards you, I want to know.  We investors should not do business with bad apples, and I will address this issue head-on with them.
  • For employees of portfolio companies I have backed, if there is sexual harassment at your workplace that is not being addressed, I want to know about it.  I will push the founders to cultivate a safe and professional work environment. If it’s the founders themselves who are acting inappropriately, I will push them to resign and/or make things right.
  • For the teams that I manage and have managed, if someone at the company has acted inappropriately towards you, I will be your champion to help you come forward and push to make things right.

We need to stop turning a blind eye to stories about sexual harassment and unprofessional behavior. If we hear murmurings or rumors of sexual harassment, we need to follow the trail to get to the bottom of it. We need to come together to make our workplaces safe and inclusive environments. And we need to start that new chapter today.

Feel free to discuss in the comments below.

Special thanks to Min Li Chan and Eric Bahn for reading drafts of this post and providing feedback.  

Today we go back to work

I haven’t really been into politics since college. Yesterday, I cast a vote for the first time in 8+ years, and today, I’m disappointed in our country.  It isn’t right to have a president who has:

  1. Screwed over numerous business partners, customers, and employees and workers
  2. Made countless racist, sexist, homophobic, xenophobic comments including (but not limited to) calling Mexicans rapists, and would like to ban people of a particular religion from immigrating to the United States
  3. Bragged about committing sexual assault and has been accused by multiple women of committing sexual assault

I have deep faith in our country.  The US, like most of the West, has enjoyed, for centuries, a legal infrastructure that is the foundation of our businesses and industries.  This is what has allowed entrepreneurship to thrive in this country.  Contrary to what many say, our recent election doesn’t alter America’s long-term prospects, but in the near term, we are in trouble.

Regardless of your politics, Donald Trump’s ethical and moral deficiencies are concerning and disappointing.  My fear is that this country will devolve, that this country will somehow see Donald Trump as a role model and think that it is OK to screw over people, to be divisive, and to sexually assault others.

It’s also days like these when we rise up as Americans and remember why we do what we do.  No matter what is happening in the public sector right now, today we go back to work.  As a bi-product of our work, we will continue to combat these things.

Today, we go back to work to continue building, investing, and coaching technology companies that change our lives and society for the better.  We go back to work to continue to level the playing field for all entrepreneurs, regardless of race, gender, sexual orientation, nationality, or pedigree, in order to not only build a better society but to bring about progress and technology for all people and not just a select few.  We continue to be more inclusive rather than divisive and judge business ideas, business partners, employees and contractors on their competence and character rather than on what they look like or where they’re from or whom they love.

Today, we go back to work to continue to chip away at the bizarre power dynamics that may often exist in industries, such as in tech and investing — to abolish sexual assault, sexual harassment, and even just pattern matching by what people look like and not on the basis of character, grit, and results.  It makes me angry that I’ve heard too many cases in this industry this year alone, and yet, few will talk about it openly.  We need to be more vocal about this to move our society forward rather than sweeping issues like these under the rug.

We have a lot of work to do; let’s continue to make progress.

 

Cover photo by Luke Stackpoole on Unsplash

You’re thinking about startup work-life balance all wrong

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Most people (including many of my friends, peers, investors) think startup work-life balance is about time – like it’s an 8 hour day or something.  But they are ALL wrong.  Let me digress and come back.

I loved my teenage years.  But, when I describe them to other people, most people think they sounded horrible.  Why?  Because I did homework all the time.  I didn’t go to parties.  I didn’t hang out with friends outside of school.  I didn’t watch TV or movies (I think The X-Files was popular sometime in those years, but to this day, I still don’t know whether Mulder/Sculley was the guy or the chick.)  I spent most Friday nights doing math.  And I programmed for fun.  My parents aren’t Tiger parents.  I just loved it.  That WAS BALANCE to me.  Would I have wanted to take 4 more AP classes?  Hell no.  I would’ve broken down.  Would I wanted to have gone to parties.  Absolutely not – I wouldn’t have had time to work on our robots.  Spending that rough amount of time compartmentalized in that way was right for me.  It made me happy. Things progressed and went well on all fronts.  But, this kind of schedule wouldn’t have been right for other people.  I know lots of people who had this kind of schedule growing up and hated it.  That’s too bad.  Looking back, it was clearly wrong for them.  Conversely, I have other friends who spent way more time studying and on their geeky hobbies than I did and equally loved their time.  I wouldn’t have been able to have had their schedules, but it was the right balance for them.

So, going back to the startup work-life balance issue.  On one hand, you have this article which talks about Elon Musk taking one vacation in the past four years – as if that’s an unbalanced bad thing.  Frankly, it sounds to me like he doesn’t need vacation very often.  That IS BALANCE to him!  On the other hand, Ryan Carson often describes his 4-day week, and that’s balance to him.  Both Musk and Carson are manning fast-moving ships. Balance isn’t something you can quantify as a set amount of time.

Some people work more quickly than others.  Some people think more quickly than others.  Let me dive into something concrete.  People in our industry seem to applaud all-nighters.  Every time you pull an all-nighter, it could be that you don’t need much sleep, and that your optimal achievement-level is on very little sleep.  But, it could also mean that you’re just a lot dumber and less efficient than your peers who could do the same thing without pulling an all-nighter.  I’ve certainly pulled lots of all-nighters at LaunchBit that made me feel super slow the next day.  Clearly, that’s not my optimal point on a regular basis.  We need to think about what schedule is optimal for each of us on an individual level.

So let’s STOP talking about work-life balance in terms of 8-hour days or some other arbitrary fixed amount of time.  Let’s START talking about how we can all find more productivity on an individual level while keeping the ship moving quickly, having fun, and without breaking ourselves.

</RANT>