One thing no one talks about are the differences in how investors within the same VC firm make investment decisions. Firms are supposed to be united in their decisions. But, the untold secret is that often there’s a lot of disagreement within a partnership over what deals to do. Sometimes these conversations can become heated. But ultimately, if a firm decides to do a deal or pass, the entire firm is united on that front – even if individuals within the firm feel differently. I’ve talked about the differences between the consensus model and the champion model on this blog before.
This is no different at Hustle Fund. There are often deals that I do that the rest of the investment team thinks are awful. And vice versa. Part of why we have a champion model at Hustle Fund — where any investment professional can do any deal he/she likes — is that outliers tend to be the most contentious.
One of the reasons for differences in opinion about a company lies in what individuals think are the most important aspects of an early stage company. For example, my business partner Eric Bahn really values great products and fast shipping of product. Of course, I think this is important as well, but in my list of things that I care most about, product isn’t always top of the list. And of course, it also depends on what the specific industry is. If you’re selling Salesforce to salespeople, then product is less important than if you’re selling a Canva subscription to designers. Product matters more to certain customers than others. But there are many other nuances about how my decision making is different from my colleagues’ that I hadn’t been able to quite articulate before…until now.
First, some context about our decision-making framework at Hustle Fund. When we evaluate startups, we use a 4 point system. 4 is excellent. 1 is terrible. By having a range from 1-4, it forces the decision maker to pick a number that is either on the weaker or stronger side. No one can pick 2.5 — you have to take a stance on whether you believe a given company is strong or weak in a certain area. And then using this point system, we grade a company across a variety of axes. But ultimately, the scores are meant to help our investors guide thinking; there’s no minimum overall score that a company needs to achieve in order to receive an investment offer. Moreover, if a company scored all 4s, it’s also possible for that company to not receive investment. E.g. it might be a pre-IPO company that has clearly proven out an amazing team, an amazing product, amazing traction etc…but then it’s no longer a pre-seed company.
So with our scoring system, the vast majority of companies we meet do not score highly, including those we end up investing in. The companies are all early, and we do not have grade inflation. But the scoring does show patterns in what each of the investors on our team care about. And having amassed a large data set of how our investment team thinks, I’m excited to share with you our results on how each investor on our team differs in thought process.
Average Scores Across Our Criteria:
We used AI to help us analyze our investment patterns. For the companies who received funding from Hustle Fund (our portfolio companies), these were the average scores we gave our companies when we decided to invest.
Team: 2.98
Product: 2.32
Market: 2.79
Execution: 2.76
Fundraisability: 2.48
This is pretty interesting, because you can see that our investment team cares about “team” most importantly. As a whole, when we meet with a founding team, we are making our decisions to invest in large part because we are impressed with the team. In contrast, even if we don’t believe the current product is great or we don’t believe the team can fundraise, we’re often still willing to make the bet anyway. As a generalization, the categories of product and fundraisibility matters a lot less relative to other criteria.
Scores Per Investor (with commentary from AI):
Elizabeth Yin: tends to score lower on average, especially in Product (2.01 average) and Fundraisability (2.19 average)
Eric Bahn: gives higher scores across the board, particularly in Fundraisability (2.65 average)
Haley Bryant: has the highest scores in Execution (3.06) and relatively high in Team (3.5)
Shiyan Koh: has high scores in Market (3.05) and Fundraisability (2.80)
This is particularly interesting and can be interpreted in a few ways.
Since these are scores for companies that get investment, my scores could be interpreted in a couple of ways. You could say I see the weakest dealflow across my team (!) or you could also interpret this to say I’m the hardest grader of everyone, including the companies we invest in. There’s probably some truth to both in that I care less about how developed your product is and care less about a founder’s fundraisibility than my peers. In fact, across the industry, many VCs care a lot about whether a startup will get follow-on funding, but I very much prefer the founder who has less glitz and glamour and just gets to work. It also means that a startup who receives funding from me may end up being largely bootstrapped for longer and may have fewer downstream investors chasing them until they achieve some serious results. That’s a bet that I’m willing to make that few VCs will make.
You can see that Haley cares most about execution and team. Shiyan most about market. This isn’t to say they both don’t care about other criterion, but you can see what we all think a lot about. (Eric gets along with everyone and hands out A+ marks to everyone :).)
Variations in Scoring (with commentary from AI):
The variations in scoring are relatively moderate across all investment team members and criteria, with Fundraisability showing the highest variation for Eric Bahn (1.03) and the lowest for Haley Bryant (0.51). This means that Eric will back a bunch of teams that he thinks can’t raise more money as well as a bunch of teams he thinks will raise money very easily.
Elizabeth Yin and Eric Bahn show more significant variations in Product and Fundraisability scores. This means that Eric and I will back some teams that have great products and high fundraisibility as well as those that don’t. We do this because many ideas don’t require that much money or a rocket science product, but other businesses do. It’s case by case.
Haley Bryant and Shiyan Koh have lower variations in Market and Execution scores, indicating all of their teams need to have strong market arguments and strong executing teams.
Common Themes and Observations:
According to our AI that did this analysis, “Each investor has a distinct scoring pattern, reflecting their unique perspectives or priorities in evaluating startups. This diversity in viewpoints enriches the investment decision-making process but also highlights the importance of consensus-building or weighting different criteria according to strategic priorities.”
Basically, we look at companies in different ways but individually, have distinct things we look for. If I were pitching Hustle Fund with a new company, I would be looking to pitch the person on our team who was best suited for my company. E.g. I would pitch Shiyan if I had a huge fascinating market, but if I were not great at fundraising, I would pitch myself with a more bootstrapped approach.
This week, I had a really fascinating conversation with a portfolio founder named Joshua Lee, who’s the CEO and co-founder of a company called Ardius. Ardius helps startups claim R&D tax credits. So it’s a no-brainer why founders sign up for Ardius, because they can get free money, and Ardius takes a cut of what they are able to help founders get. If they can’t help you get any credits, they don’t get paid.
But what was fascinating was that when I was talking with Joshua, he said that one of his learnings in trying so many startups over the years, was that founders don’t think enough about their exit path before starting a company. Ardius, in fact, was not his first company, and so after many companies that didn’t work out, he decided to work backwards to figure out what to build.
I asked him, well, what do you mean?
He said that when he started Ardius, he not only talked with potential customers, but also talked with potential competitors – large companies who could potentially be building a competing product on their own. He was trying to see if he could manufacture his own exit before starting Ardius. He wanted to know what the M&A appetite would be if he were successful. He wanted to know how big of an opportunity large companies saw in what he was building.
And I asked “wasn’t that kind of dangerous to talk to companies that would potentially be building the same thing?” And he said, when he talked with a lot of the major players in the HR benefits space, in fact, many of them were building a competitor to Ardius. And some of them even told him they would squash his company.
While that was frightening to him, his thesis was that if you’re good, startups are actually way scrappier, faster, and more specialized and can run circles around most large companies. And as it would turn out, he was able to plant seeds in their heads that in case they were not happy with their own progress, they should stay in touch.
Ardius ended up doing quite well as an independent entity. And that caught the eye of all of these would-be competitors. Fast forward, Ardius was acquired by Gusto in 2021 after discussing with all the major players in the HR benefits space. These were relationships Joshua had already been building for years, which made the acquisition process quite smooth.
Now this whole story is a pretty controversial path. Many venture capitalists wouldn’t like this path, because VCs would prefer companies to keep raising money if it makes sense to continue to swing for a larger exit. After all, VCs need their winners to be large enough to above and beyond overcome the losses of portfolio companies who fail.
But, Joshua’s view is that VCs should think about the faster liquidity they could get with a manufactured exit. Instead of waiting 15 years to get to 100x (or more), would you rather wait 5 years and take a 10x? He thinks the idea that you have to wait a long time for liquidity in venture is outdated. From an IRR perspective, his model is also way better. In fact, in this particular example, the IRR of the longer time period is 36% vs 58% for the shorter time period.
Not to mention that we didn’t talk about how with his model, the team isn’t grinding too long to lead to burn out. Nor does the team become too big and chaotic, as you often see at large fast-growth late stage startups.
His argument certainly made sense to me. Certainly, if you were running your own angel investments, his proposed model is intriguing. You get your money back sooner, and you can redeploy sooner into other investments.
But, it made me think why this doesn’t work in the traditional VC model. VCs are judged on multiples returned as liquid cash over the term of the fund. Typically funds have a 10 year lifespan. So in this model, the winners aren’t around long enough to become huge winners. And yet, if you’re getting money back in year 5, you don’t have enough time either to deploy the returned capital back into new startups. So, the cash is just sorta stuck — either doing follow on checks into later stage companies, which tend to have lower multiples than early stage startups OR it just gets returned as cash and isn’t enough cash to make up for many of the portfolio losses. In other words, this model — assuming it works — works really well in an evergreen fund but not in a fund with a set term limit of 10 years.
All of that said, his model of building relationships with potential partners / acquirers / competitors from day 1 is smart — even if you aren’t looking to get acquired right away. One of my other portfolio founders did something similar, not for the purpose of M&A, but for the purpose of building relationships and ended up getting acquired by essentially a would-be competitor, because she had built those relationships early.
It may be scary talking with potential competitors – especially when you have nothing – but if you truly believe that your startup is great, you can outcompete your competition. As we’ve seen time and again, more funding does not equate to more success.
One thing that I am skeptical of in this model is the notion that you can actually predict what will be acquired. And therefore, your loss ratio is lower. Afterall, one of the hardest parts about building a startup is finding a repeatable sales process and enough customers who want to pay for your product. M&A demand is predicated on the assumption that your product will find very strong product-market fit. If you are able to find customers but only slowly, your would-be acquirers might decide that there isn’t enough demand for your idea. And, you might not be able to manufacture the M&A deal you thought existed when you set out to begin your company. In other words, I’m skeptical that you can come up with a higher batting average of ideas that are successful that companies will want to buy than the traditional VC model.
I always learn a lot from my portfolio founders, and this model of building-for-exits is certainly food for thought.
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Last year was an incredible year for artificial intelligence (AI). If the rise of the internet was an inflection point, the rise of artificial intelligence (in my opinion) is an even more massive one.
I think what I’m most excited about is that sometime in the near future, everyone will have the ability and the access to build anythingdigital. It could be websites, movies/films, songs, mobile apps, comic books. You just need a device (phone / laptop / tablet), internet, and creativity.
In the 90s, with the rise of the internet, this started to become possible, but you still had to run to Barnes and Noble to buy books on how to code. The most motivated quick learners reaped the benefits of the internet in the first inning. You also often needed servers that filled closets and needed to handle the maintenance of all this yourself. It was not a super accessible period of time — not anyone could do this — but it laid the foundation for where we are today.
Fast forward to today, you don’t need to know how to code to build digital things. There are so many no code tools available to take the heavy lifting off of building, and you can learn about all of this with simple video tutorials on YouTube. There is so much that has already been made accessible to the billions of people on this planet. I learn a ton from watching YouTube videos — there is no better educator than YouTube (in my opinion).
Yet, despite these advances, there are some things that historically have still been hard in the last decade or so. For those who have no talent — like me — design, for example, is still hard. I can read and watch tutorials all day, and I still will not be able to draw well to save my life. If I practice for years, I could probably get better, but I won’t be able to come up with cool images or videos in the next couple of months.
Until last year.
Enter Midjourney and so many others. Last year, I thought I could finally fulfill my childhood dream of becoming a cartoonist to draw comics about my favorite stuffed animals I grew up with — all with zero talent.
But, is it hype or is it real?
Meet Warren Hippothat I created with Midjourney
My childhood stuffed animal Warren Hippo should be at least 30+ years old by now, but he is somehow forever 5 years old and will always be 5 years old.
Midjourney was able to make him look pretty real. And more importantly, pretty close to the original Warren Hippo too:
Meet the original Warren Hippo
Pretty close-ish right? I thought I was on my way to becoming a professional artist.
Unfortunately, image consistency quickly became a huge problem, and it’s one of the top issues that Midjourney users want solved (according to a poll in their Discord community).
Midjourney renderings of Warren in various poses. He seems to have…evolved into a different hippo.
Modifying Warren into different poses was an entirely different exercise. Pretty challenging, and he turned into a different hippo. While it’s still really impressive that you can generate these new images of different poses in about 30 seconds, the character consistency will have to get better in order for the technology to truly enable the next generation of comic book artists, brand marketers, and designers, etc.
And this issue isn’t just limited to Midjourney. The generation AI tools I’ve played with are all really good at generating single-use images, but it’s much much harder to create themes, characters, and brands that you can use over and over again. This is getting better, as you can now seed designs with other images and you can preserve past images as well. But, as of writing this blog post, this is still a major blocking point.
In addition, these tools are all great with common images — like dogs. If you want to create a cartoon dog, it’s easy.
But what about something that doesn’t really exist? Something that doesn’t really exist even in people’s imaginations? Like a hippocorn?
Dunky has wings and a rainbow horn and two large teeth
Unfortunately, because the internet doesn’t really know what a hippocorn is supposed to look like, it’s hard to describe it using generation AI tools. You get weird stuff like this:
Early version of a generated hippocorn image
In fact, we did many iterations on our prompts to try to create a good hippocorn design for our announcement of our plushie. Alas, we were unsuccessful.
Generative AI tools are, by definition, horrible at creating images that don’t really exist, because it has no data to work with.
Over the holidays, I was determined to create a great hippocorn cartoon using Midjourney. So I spent a couple of days working on this. (I know, this is a ridiculous hobby.) I realized that if I were going to be successful, I needed to feed it the data to train on. I ended up seeding Midjourney with a ton of photos of our stuffed hippocorn, and the results turned out a lot better.
After a few days of work, this looks a lot closer to our plushie hippocorn Dunky
But even in seeding it, Midjourney struggled to identify its wings (this is why you see a white shawl around the hippocorn). It took a long time to interpret the two white squares as teeth as well.
In addition, it struggled to render different poses of Dunky as well. You can see the teeth were lost.
Renderings of Dunky the hippocornafter having a tooth extraction at the dentist
But, maybe it’s good enough for some use cases.
Ultimately, we were only able to create hippocorn cartoons because we already had designed a hippocorn. In other words, we needed a designer to create our stuffed hippocorn in order to feed the AI models with our design. It would have been impossible to create a hippocorn from scratch with no designer.
This is where AI still falls short. If you are creating something completely new, you will still need a designer to design what you are developing. That being said, AI can probably speed up some bits that are too tedious to do manually, saving your designer some time.
Why bother with your stupid hippocorns?
As we assess products in AI, which is an incredibly competitive space, these nuances matter…A LOT! I think it’s easy as a VC to watch a demo of a product and say “Wow, that image generator can do ABC things.” But really testing the limits and edge cases is important to understand the state of AI and stay on top of who has the lead.
It’s also important not to write off any of these companies because of these limits. I’ve seen so much change in all of these generative AI design products in just the past few months. They are getting better so quickly, and I suspect in a year from now, some of these problems that I’m writing about here will be solved.
What the future looks like?
Eventually, we’ll look back and say, “Wow, the 2020s was an amazing era for technology.” You’ll be able to build movie studios from your computer and distribute your films on the internet, disrupting the traditional movie industry. You’ll be able to write or draw books, including graphic novels, on the internet and distributed on the internet, disrupting the publishing industry. You’ll be able to create websites and mobile apps more easily — as just one person.
So, if I were going to start a new company today, I would probably not build an AI company — there are so many of them. I would probably build a company that thrives with the assumption there will be a lot of AI companies to help us design and build faster and so much more. For example, at Hustle Fund, we hire no-code developers, because you no longer need to code everything from scratch to get things built. That’s an occupation that didn’t exist even five years ago. So, what are the new roles that will emerge in the next five years? I’m sure there will be prompt engineers in the coming few years. Or maybe QA testers for AI. Maybe you’ll need tooling or legal for the creations you develop through all of these AI tools. Think about what that world looks like — I would build a company for that world, because it is arriving so quickly.
Momentum is moving creativity forward quickly. We’ll see new brands arising from individuals and influencers. The next few years will be remarkable.
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A decade ago, I wrote a blog post about how I was not crushing it with my startup LaunchBit.
In that post, I added this graph:
It looked good — up and to the right (though no labeled axes publicly disclosed). But, on a day-to-day basis, the graph looked like this and more importantly, *felt* like this:
Doing a startup is HARD, because it’s hard to see the long-term ups of where you’ve come from and how much you’ve accomplished. And it’s easy to see all the troughs you have to stomach today.
The headfake about my current company Hustle Fund is that even though we are a VC fund, we share many more similarities to our startups than we share with other VCs. This may sound counterintuitive, but we have revenue (with ups and downs of it – just like our startups) and lots of people (30+) who count on a paycheck. Managing money and lots of people is what makes companies hard!
I write this post, because I know that a lot of startups are struggling right now. Capital is tight. It’s hard to make money. It’s hard to console your team who may be worried about the market. I know – I get it.
An example of one trough that I’m going through right now is that I recently learned that I will have to personally chip in a lot of cash — more than I made last year — to cover a company tax situation. I know that so many startups often have founders contribute to their respective businesses to make ends meet. We all face the same issues. This won’t be easy for me. But we’ll figure it out.
In fact, the past couple of weeks or so have been the toughest point for me in our journey — even tougher than those first few months when my business partner Eric and I couldn’t raise that much money for our Fund 1. In many ways, it’s much harder to go through troughs when you’re a bigger company than when you’re two people working in a garage. (Ok, Eric still works in his garage).
A decade ago, I felt every trough so deeply. I was stressed. But there are a few things I’ve changed over time.
Gratitude
A few months ago, I spoke with one of our founders whose company is thriving. But, she saw her business go to zero during the pandemic and recounted how one day during the pandemic, it was just so stressful, she cried her eyes out in her empty office. I asked her, “What made you decide to continue your company and how did you ever pull through?” She told me that she realized that just being able to sit on the floor and cry about her startup was a privilege and that she wanted to continue.
That conversation summarizes how I think about my own startup problems now. It’s a privilege to be able to do this work day in and day out. No one is making me do a startup. It is a gift to be able to work with the amazing Hustle Fund team to get through problems – I am so so grateful.
So even though there are a tons of ups and downs in doing a startup, there’s no way I would give this up to do something else.
My health / habits
I’ve talked a bit on Twitter about how I’ve changed some of my habits which has made it immensely easier to handle stress.
With my first company, I used to feel stressed all the time and had lots of trouble sleeping.
The ups and downs never go away in building a company, but here are things that I do differently in building @HustleFundVC
Sleep early and wake up early to get a better handle on the day
These changes alone have helped me get a better grapple of not only my time but also my stress.
I also think being a second time founder helps. You know what issues can crop up and not much is surprising anymore.
But, The Ups and Downs are Always There
I think founders often think that if they can just get to the next milestone or the next round of funding, there’ll be more stability and fewer ups and downs. This couldn’t be further from the truth.
On some level, there’s more stability — there are more people to mitigate the chaos (assuming good processes in managing the team). But there’s also just more at stake and issues always arise, so the problems become bigger.
This is fundamentally what startups are all about. Constantly ploughing through and getting pummeled and rinsing and repeating. And this can be depressing for some founders. And, this is not for everyone — and that’s ok to move on.
But if you’re still excited to try to surf your startup wave, keep going! Everyone gets pummeled over and over again — you’re not alone — but just get back up on the board and continue. You’ll figure it out.
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Although I invest in a lot of pre-revenue startups, a stage where I see most companies get stuck is the pre-series A stage. There are two primary ways that companies tend to get stuck. A startup:
Has product-market fit but is too chaotic in trying to serve demand
Doesn’t have product-market fit but thinks they do and overly spends money and runs out of money
What is product-market fit?
At a high level: You have found product market fit when you can repeatably acquire customers for a lower cost than what they are worth to you. This is not earth shattering. This is a simple business statement. Are your costs lower than your revenues? Are you profitable? And can you get more and more customers over time in a systematic way?
I’ve written about this before on Twitter:
What the @#*($&# is product market fit?
I've been trying to study PM fit for the last decade. First with my own startup (that never reached PM fit) and then with my < 300 companies I've invested in and the tens of thousands I've reviewed. Here are my thoughts on PM fit:
This is something I didn’t understand when I was a founder. Investors would often go around saying “you just know you have it,” which I didn’t find helpful back then. Now on the investor side, I think this is a true statement: if you can’t keep up with sustainable demand, then you have product-market fit. If you are overly spending — i.e. payback period is longer than say 6 months at the seed stage — to get demand, then you don’t have it. You are just spending money unsustainably.
It’s important to be honest with yourself about whether you have it. The truth is – most companies never achieve product-market fit. And, my startup certainly never had it. The market doesn’t generally need most companies. And that’s ok.
Even companies with product-market fit can fall apart
However, even if you have product-market fit, that’s only half the battle in running a company. I often see companies still get stuck. I’ve had many portfolio companies find product-market fit but get close to either running out of money OR actually run out of money, because they didn’t keep a close eye on their cash management.
Even if you are basically profitable in serving your customers, you can still go out of business. For example, if you have a large cash outlay upfront to buy materials for your product before you bring in revenue from selling said product, you could easily run out of money. If you haven’t read the book Shoe Dog, by Phil Knight yet, I highly recommend reading it to dig deeper into this particular conundrum. Shoe Dog is the story about Nike and how they almost ran out of money quite frequently. In Shoe Dog, Nike needs to pay for materials to make their shoes upfront and then sell them later. But, the more shoes they sell, the bigger their outlay of cash has to be each time they buy more materials. So although Nike has a ton of demand for their shoes, it’s incredibly difficult for Phil to solve for their liquidity issues to keep up with demand. Their success actually creates cash problems for them.
This issue doesn’t just happen with e-commerce companies. It happens with logistics companies, ad companies, and B2B companies as well. There’s often a hefty outlay of cash upfront to pay for people to help serve a deal or pay for the cost of goods.
Pre-series A companies need to optimize
For all the reasons described above, I’ve thought a lot about the optimization of growth and startups. Everyone – investors and founders – are all fixated on growth. But once you have some growth, especially during tougher financial markets when it’s less easy to raise money, it’s the founders who can optimize their companies well who will be positioned to be successful.
Truthfully, Hustle Fund recently has been working through its own growing pains of optimization. We have 30+ people now at Hustle Fund and beyond our VC funds, we have several business lines that all work together. Some business lines have product-market fit. Others are more nascent and are too early to tell.
With my last startup LaunchBit, we never hit product-market fit, and we never were this large either in team size or revenue. And with so many people, at Hustle Fund, it’s sometimes hard for us to figure out what cash outlays are happening to ensure profitability when we are paid. In addition, with so many new people at our company, sometimes there’s just a lot of chaos. So we had to make some changes to our own business:
We now have a Company Operating System that allows for scale
For most of the last five years – esp in the beginning – most of the knowledge of how we do work at Hustle Fund has been in people’s individual heads. After a while, this made onboarding new hires challenging and it slowed down work.
Every company goes through this transition where at first, it’s fast to not have documentation and processes (e.g. 2 people in a garage who are still figuring things out). But at a certain point, this way of working becomes a crutch and then you have a lot of inefficiencies on your team when no one knows where things are or what is happening or who does what.
Spearheaded by Thenuka Karunaratne, he set up the system for us to help level us up to do business at scale. Thank you Thenuka! In our Company OS:
There’s a single source of truth
Everything is documented there
If you do something more than once, we record a video and just add the video to the documentation to make it faster / easier to document. No one has time to write documentation
Done is better than perfect. Revisions happen all the time
Consistent communication channels creates prioritization
Hustle Fund is also a fully remote company across the globe. Most of the people who work here had never worked at remote companies before, so we had a tough learning curve in how to communicate – especially across time zones.
We had to set up guidelines on what communication channels are for what and everyone must be aware of these from day 1.
E.g. Email — this is where work gets done. Subject lines with [ACTION] or [ACTION by 3/1/2023] get higher priority within our team.
In contrast, Slack is where messages go to die. BUT, Slack is important. We have a Shoutouts channel to praise people on our team publicly. We have a channel for news articles. A channel for our own weekly updates. As you can see, these are all great channels for getting to know team members and staying in the know.
We also use Async.com and Loom videos a lot to remove meetings. Instead of a meeting, we send a Loom video or an Async voice memo. It’s way quicker than writing details in an email, and the recipient can quickly read the transcription to digest it. And, you can also convey emotion, which is so so important when you are sending feedback on ideas.
Templates, templates, templates
Lastly, we write and share templates with our team on what to say to various scenarios. This allows us to have consistent messaging and with two clicks, we can respond to most inquiries fairly quickly. There is no reason to re-invent the wheel.
As you can see from our own journey of leveling up both at Hustle Fund and helping our portfolio companies level up, I’ve always wanted to create an epic guided offsite for pre-series A founders.
So, I’ve been working closely with Tam Pham, the newest addition to our team, in creating a Hustlers’ Retreat–a guided strategic offsite for leadership teams this year.
Here’s the thing: Lots of founders get bogged down in the weeds with things that seem important, but don’t actually move the needle on the business – for all the reasons above.
So here’s our vision for Hustlers’ Retreat: we’ll take ~25 leadership teams out of their daily chaos into nature. They will finally have time to slow down and think strategically about their future.
We’ll facilitate workshops to help founders with their top priorities and build their company operating system. We’ll also offer sessions on customer acquisition and fundraising.
The goal is to help pre-series A companies with:
Prioritization
Getting leverage on their time: Going from an individual contributor to a manager
Raising money beyond the seed: What they should do today to prepare for future raises
Attracting A-players to work for their tiny startups: Plus retaining those key employees when you have limited cash
Acquiring customers: Growth will always be a constant at every stage
The best part? We’ll take care of the whole experience. The Hustlers’ retreat will have:
a private property that spans hundreds of acres in beautiful Sonoma County
cooks on-site to provide nutritious food for you and your team
our team and guest speakers to facilitate all the workshops and sessions
fun activities to recharge & connect like volleyball, board games, a pool party + more
a community of hustlers just like yourself to connect and learn from each other
Our goal is that every leadership team will walk away feeling recharged, aligned, and energized to tackle the next chapter of their business at scale.
Anyone can join, but the sweet spot is for pre-series-A cos.
You have a live product
You’re making at least 6 figures/yr w a path to 7 next yr
You have a team
So if you’re a founder who is at a key inflection point in your business, we designed the Hustlers’ Retreat for you. It will take place Aug 20-24, 2023. We’re also doing something crazy and paying for your lodging (4 nights) onsite to the first 35 tickets, use code “HUSTLER”.
My teammates and I will be connecting with founders throughout the week and facilitating sessions. Hope to see you there!
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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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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…
to learn about great companies / improve dealflow
to help your existing portfolio companies by building key connections
to help your own VC fund’s fundraising efforts
to grow your angel investing syndicate
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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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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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! :D
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 withcapital, 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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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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Tactical fundraising by Elizabeth Yin 