Trends in the Tech VC industry

Coauthors: Elaine Truong, Neil Serebryany 

Over the past few months, there are a few trends in venture capital that we have noticed. As we got our toes wet, we were surprised to find out how qualitative the industry approach is when it comes to evaluating investments.

However, the VC industry has gone through a number of fundamental shifts in the last couple of years and the ways that startups are funded in the future are changing.

One of these major shifts is that more and more startups are being created every year. With so many startups to sort through, the tech VC industry has adapted with its own titanic shifts in investment methodologies and evaluations. VC is largely a people-centric industry where investors go to their network for everything from referrals, market research, and guidance in evaluating startups. However, there appears to be a trend towards  with this people-centric approach is now being complemented by quantification. Since the VC industry has such few winners (only 20% of firms make money) there’s an increasing need to test new strategies. The key disadvantage of a referrals-based process is that investors are only limited to who they know and end up missing out on potentially game-changing deals because they don’t have the analytical resources to evaluate each deal adequately. The following is a list of trends I’ve been noticing within the tech Venture Capital Industry and why they matter. 

For a long time, tech VC was like private equity where partners have traditional backgrounds in investment banking or consulting. Recently, we are seeing more partners with hyper-specialized skills and specific domain knowledge. 

As startups become increasingly competitive and more difficult to launch, the value each investor brings is significant. Tech VC firms are bringing on board specialized people who have experience with technology and startups. Notably, A16Z (Andreessen Horowitz) only has partners to have prior startup experience, resulting in a team that understands the evolution of a startup and the core technologies that power a successful venture rather than a team who understands how to do a double irish (a complex tax strategy). Tech VC used to be rooted in finance and drew it’s people from private equity private equity but it’s moving further from its finance roots since fundamentally the skills needed because tech companies develop differently at the early stage and you aren’t doing value investing - your job isn’t to make things more efficient, it’s to create new things.  Startup experience is crucial for partners to offer value to early-stage portfolio companies because former entrepreneurs will understand key metrics, great product, customers, and failure. 

Changing Expertise & Talent in VC Funds

In the 1990s, a lot of VC firms had more people who could complete an M&A transaction for a large company or advise a corporate CEO on his company’s tax strategy than people who understood product and how technology works. 

The core skills of VC employees, however, are changing. From engineers and designers to subject matter specialists, more and more VC employees have worked within the field of technology before going down the VC or consulting route due to the fact that it’s hard to intimately understand an industry and what a company should look and viscerally feel like without being present in the past at a startup. For example, KPCB’s team distribution clearly shows that individual backgrounds are more diverse, more tech-focused, and less oriented towards the world of management consulting or corporate finance.

On the partner side, it's become almost a requirement that you start a successful company or work in a senior role at a high-growth startup to become a partner at any well-respected firm. From anecdotal experience I’ve found the distribution to be successful entrepreneurs can start their own firms our become partners at existing firms while startup employees or individuals with failed startups beneath their belt become associates.

VCs that regret missing out on giants like Google and Facebook are now increasingly concerned with seeking the next hot startup. VCs know that the worst thing than being the highest bidder is being the only bidder so they tend to compete for the most-hyped-about startup. This fear of missing out on potential ‘unicorn’ companies have led to some shifts in approach. To stand out among the many VCs trying to get a piece of the hottest startup, a VC has to offer much more than funds. The investor must possess expertise, domain knowledge, connections, and must resonate with the startup’s vision in order for the startup to admit the VC in their funding round. In addition, VC partners have to demonstrate to the community that they care passionately about the startup ecosystem by speaking at conferences, writing blog posts, and maintaining their personal brand.   

A case example is discussed in this Fortune article - Renaud Laplanche, CEO of online credit site Lending Club was about to close a 9-figure funding round from private equity investors before Google Capital swooped in, with Laplanche reflecting that it was “the most value-added investment we ever had.” Similarly, Google Capital created 10 working teams from their 40,000 pool of Googlers to help portfolio company ZenPayroll with “things like choosing a new office location (Denver) and developing a plan to beef up its customer-service team.” 

This huge shift means that VC partners & employees can empathize with founders, bring more realistic expectations to the table, and, most importantly, they can help troubleshoot or provide support and guidance to their portfolio companies. Given their in-depth knowledge of tech, they can also evaluate technologies and markets better. 

Subject Matter Expertise

After A16Z came onto the scene and fundamentally challenged VC firms by introducing full- service VC’s (the CCA model), many VC firms took a similar route by offering legal and financial expertise or media opportunities (i.e. services that previously required startups to invest their own money). 
Firms are also building a lot of internal technologies to share with entrepreneurs, because they’ve realized that it doesn’t make sense to do the work over and over again in terms of building tools to scale up growth.


Angels and AngelList are revolutionizing the Valley. 

Angels are becoming increasingly powerful and active because of a few reasons:
 1) the type of investor has shifted to one with successful startup experience and
2) angels who can act quickly and make fast decisions are increasingly valued.
3) Angellist is becoming an incredibly powerful force in the valley that has delivered companies like Shyp, Honeybook and Soothe.
4) Angellist has been able to raise a $500 million dollar round.

As more and more deals arise, a phenomenon is occurring in which there are too many deals for established VC firms to screen. Thus, new types of funds and people are investing through crowdfunding and online syndicates. Additionally, the SEC is moving forward with Title III of the JOBS Act in 2016 to allow non-accredited investors to participate in equity-based crowdfunding.

VC firms also have an incentive to diversify and spread risk across their portfolio, and increase the number of investments. With pre-seed and seed rounds becoming the new “Series A,” people are making high-risk micro-investments. The AngelList investing model, which allows angels and institutions to invest online, offers more transparency in funding rounds. Entrepreneurs can increase their company’s visibility and investors can syndicate investments. 
The high number of deals and the large amount of money entering the VC market is placing more pressure on LPs to invest in ‘hit’ deals. Associate positions are increasingly competitive as LPs look for young recruits with wide networks to source investments - the best example of that is the growing number of micro VC funds (according to Samir Kaji, there were 250).

Democratization of startup funding

More and more hot startups are now being funded by regular investors rather than top 10 firms thanks to the Jobs Act, a bill to jumpstart the economy that allowed equity crowdfunding from accredited investors. Title III of the JOBS Act will level the playing field even further in 2016 by allowing non accredited individuals to participate in funding rounds. 

AngelList is the main vehicle for this type of financing and it is exploding - $100 million was raised on AngelList last year. Investors are using it as a channel to source startups and entrepreneurs are encouraged by success stories to reach out to mentors through its platform. 

Associate to fund

Associates/junior partners oftentimes have an easier time forming relationships with founders since they are more likely to have startup experience. More firms are looking for successful entrepreneurial experience rather than corporate or banking experience in their junior recruits due to the fundamental shift towards full-service firms. For firms that make seed investments, it’s difficult to find investable startups that fit their criteria since the challenge is that such early-stage startups are under the radar and relatively unknown. Thus, partners often send associates to related networking events to build their social capital. 

Lately, there has been a trend of LP’s funding the creation of small funds by these younger VC’s (see KPCB’s Edge Fund) because they oftentimes have access to a lot of deal flow and are better positioned to see trends in the marketplace due to their background and younger age.

More deals are occurring and many more companies are being funded by VCs that are encouraging a data-based reality. VC’s are catching up to automated investing trends (Google admits to using algorithms to evaluate deals) and are trying out new tools in ‘blackbox investing.’ The VC industry is becoming much more competitive and since it’s such a hits-driven industry, start discovery tools have an outsize influence. What this means is that the VC industry needs new tools to discover startups first because the traditional people-centric model isn’t working and tools like CB insights and Mattermark are trying to fix that hole. They are also looking into more efficient ways to evaluate startups because only 25% of firms make money and actually achieve superior returns. 

Quantitative discovery of companies

For a long time, venture capitals rely on second-degree referrals for investment consideration. The problem with a referrals-based networked system is that every venture capitalist is looking for the next Palmer Luckey, or the next Docker. However, so many groundbreaking innovations and teams may not have any direct links to venture capitalists. 

Venture capital is moving towards a more outbound future analyzing which factors (especially for technical companies) directly correlate with success and outreach. 

The problem lies in diminishing returns - as more people start using this type of methodology - the inefficiencies in the market that allow such a technology to work are fixed.

Quantitative Assessment of Companies

Since VCs who invest in early-stage companies often evaluate investments by the quality of founding teams, they seek a level of trust and personal connection with the entrepreneurs. Vice versa, entrepreneurs seek partners, not just investors. VC deals are assessed by looking the founders in the eye and making a subjective judgement of whether the VC can trust the founder. There are a number of problems with this approach, the biggest problem being that the type of founders being backed are of similar backgrounds and are working on ideas that target the same people. Thus, this neglects huge, untapped opportunities to make money in other unfamiliar industries. 

Currently, it takes many years of experience doing deals and witnessing financial cycles to accumulate the knowledge needed of a reputable VC. This is both time-consuming and expensive as investors will have to endure several failures before seeing a success.
The VC industry is undergoing a shift - only 25% of firms make money because the primary differentiator between the best firms and the worst has been access to deal flow. VCs are now realizing that there are other ways to differentiate themselves such as getting in earlier and crunching the data in new ways. 

Single Base

Smaller VC funds are often having an easier time achieving a 4x return due the to the fact that if you have a fund that’s $100 million or above needing to find unicorns (companies valued at a billion dollars or above) due to the math of it. If we take a 100 million dollar fund that’s later stage - each partner makes ~3 investments a year over about 3 years (the typical investment time that I’ve seen) and the fund would probably have 4 partners.  They would try to go for about 20% of a company under this model and what that means is that their companies have to create a combined $2 billion dollars of value in order to be a top fund. The mat gets even more difficult the bigger the fund is (IE: I $1 billion dollar fund would have to deliver $20 billion in value to return the fund).

Ideas for future directions include:

  1. Project based evaluation of entrepreneurs. The best way to evaluate a good entrepreneur is to work on a project with them. Possible ways to do this in a scalable way include having an online platform for entrepreneurs to propose a case study for his team to work on.

  2. Analytics tools and the methods that VCs use to eliminate subjectivity and human bias.

  3. Use affective computing tools like the facial action coding system to see how truthful entrepreneurs about a project are and if they are passionate about them.

  4. Another trend that can occur are better stores of information on typical patterns in an industry because it's hard to evaluate a founder's market assumptions without having an industry expert.

  5. Growing internationalization of startups - the goal of a startup rather than any other type of startup is to fix a problem and rapidly grow to dominate a market and the pool of venture backed startups for a long time has mostly been limited to the United States. but that makes no sense - the United States only has about 5% of the world's residents.

Overall what these trends tell us is that the VC industry is in a period of bifurcation with the top firms taking almost all of the profits and small firms existing just like a seed stage startup on the premise that in the future they’ll be able to generate large profits. VC’s are looking for new tools to nurture and discover startups and hopefully generate better returns by moving towards diversification and data-centric investment analysis.

Overview: Singapore’s Startup Landscape

My original Medium article here

Singapore is about half the size of Los Angeles but that doesn’t keep it from being an economic giant in international trade. Its humble origins from a kampong (“village”) is found in its Peranakan shop-houses, contrasted by gleaming skyscraper facades in the Marina Bay. This Economist article recounts the last 50 years of Singapore’s accomplishments. Most notably, it makes the point that the city-state’s future may suffer from a complacent society in which current prosperity will result in policies reverting to what’s tried and true instead of self-renewal. It got me thinking recently about how these S-curve societies, where maturity corresponds to a growth plateau, can continue innovating or even jump from one S-curve to the next. Perhaps the most vibrant sector to me in Singapore is its nascent startup ecosystem, dubbed the “Silicon Jungle.” We all hear about the crazy growth of Asian tiger countries, and it’s no secret that the government has played a huge role in this economic prosperity. However, this also means the government gets to decide who makes it through the funnel, which implies that decision makers have to make educated bets on companies. Once these companies mature and policies revert, would growth decline? If activity is stagnant to begin with, then any growth will appear like hypergrowth. So is it right to compare them to startup grandfathers like Silicon Valley?

I spent two summers here, the first one working for a government research arm for groundbreaking technologies and the second summer in a Singapore-born startup. I’ve noticed a few interesting things about the ecosystem, so here are my takeaways.


  • In an effort to generate the next “Google,” the government has been ramping up its startup efforts by pumping millions into investing schemes to provide capital for burgeoning startups. Co-working spaces (eg. Block 71, BASH @ Block 79), which house over 500 startups, are infrastructure projects funded by the government. Down the street are Biopolis and Fusionopolis, home to massive government divisions for technology commercialization and a factory for the next hot spin-off. In fact, the startup I worked in licenses technology exclusively with a government research arm who has injected almost S$1 million into our company, taking <4% equity in return. It’s hard for startups to ignore the enticing government grants and opportunities — even Infocomm Investments offers accelerators like StartupBootCamp or Plug & Play funding resources and curriculum support. Personally, I think this government effort is amazing and has clearly proven to drive the hypergrowth in the past years. However, I am a bit wary of startups that receive millions of government funding, build a false sense of validity, and fail in the market due to lack of product-market fit.

Wealth Power

  • In the US, a lot of the wealth is concentrated in firms and corporates whereas in Asia, it seems to follow a more traditional structure where family foundations and businesses hold more of the wealth. I’m not sure what this means for the future, but my questions are around how would this affect future investing practices? I suspect that there will be a trend towards private funds for these individuals to invest their wealth or a rise in full-service VCs who provide more than just financial resources. Additionally, more of these foundations will veer away from purely philanthropic efforts and will seek investments with measurable returns (“impact investing”). However, their investments will likely remain local or regional — a few reasons that I could think of is that most foundations operate on a regional level at most and will have difficultly with overseas deal flow. The second reason is that there is a level of risk associated with investing abroad: unfamiliarity with the local governments, inability to monitor and help startups closely, et al. Government investment arms like GIC, which has assets of over US$100 billion, increasing their efforts 3x in 2014. Last year, they invested in Square, Flipkart, and FiscalNote. This activity will likely continue to encourage funds in the upcoming years, pointing to more attractive opportunities for seed funding from the government.


  • Because the startup scene is still early stage, there has yet to be a generation before Millennials who have the key entrepreneurial experience to influence startup culture. Instead, you see many young startups copying Silicon Valley culture with its open floor plans, foosball tables, and free lunches. I noticed that in ideal Silicon Valley startups, the culture is extremely strong and inspires its employees to do more, work harder, and drive the vision forward with full force. However, those without startup experience are less familiar with these workplace attitudes. For example, being a housewife is still a coveted profession here and some even believe in the old adage of the male breadwinner (only 58% of females are in the workforce, as compared to 78% of males). Younger people are more likely to have some knowledge of startup culture or experience working for a startup. Even so, the education system is largely merit-based and emphasizes rote learning. Kids are growing up adopting risk adversity — in this year’s SG50 video played at the National Day Parade, youth answered “What do you want to be when you grow up?” Many had admirable replies like “fireman” or “politician,” but not one single person said “entrepreneur.” For a stark contrast, 7 out of 10 American high school students want to start their own company (Gallup). Singapore’s exam-based education system ultimately shapes how entrepreneurship is viewed. Outside of its tight-knit startup circle, I have seen few locals who would even consider entrepreneurship as a viable career path. This ultimately affects the job landscape and a professional’s skills. More experienced folks usually come from traditional backgrounds and have less startup experience, simply because there were fewer startups to work for a decade ago. Thus, these employees with little startup experience are used to “work-life balance” and “9-to-5 jobs”, terms used sardonically in the Valley. In my experience, this mentality is a detriment to nimble startups who must continually innovate and play catch-up.

Local Solutions

  • If you’ve been following Tech in Asia or e27, it’s likely that you’ve heard of Carousell or GrabTaxi or Lazada. I’ve noticed that a lot of the successful startups in this region are primarily ones with a validated and “safe” product, i.e. e-commerce, delivery services, etc. It’s rare to hear of someone working in drones or space exploration or even artificial intelligence. Where’s all the disruption? I discovered that most of the innovation is concentrated in government entities, like A*STAR’s research institutes, which have big purses and cushy nets to fall back on. However, they are researchers and professionals with no startup background, and thus many technologies never make it out of the ivory tower. If they ever do, then they are pounded with many challenges like low adoption rates or no product-market fit. What might work well in Silicon Valley, like virtual reality headsets, may not be well received here. The market is simply too small for disruptive technology to scale. In addition, moonshot ideas are usually high-capital, high-risk, and the small risk appetite here may set up such a startup to face many challenges. It seems to me that people in the ASEAN region are more open to B2C (e-commerce, taxis, food delivery) businesses that solve local problems instead of new frontiers. It’s simply because the local and regional markets are not ready to adopt such technologies and there is a misalignment between a disruptive product and what the market desires.


  • I found it true that quality talent is difficult to come by in SEA. Developers are seen as the bottom of the pyramid here — the celebrity job in the US might be software engineering which rakes in 6 figures, but in Singapore, the most well-respected career path is public service, finance, or professional degrees (law, medicine). This mentality discourages students to choose engineering majors in school and if they do select a tech major, then the job market is bleak for them. First, there is an issue with retaining local talent because many will gravitate towards Silicon Valley where salaries are higher and developer evangelists are aplenty. is an example of a tech startup that previously based itself in Singapore, and then moved to Silicon Valley for its higher density of talented developers. Second, local developers face competition with outsourced, cheap labor from India and China. Many startups here look to outsourced talent for their engineers, which I think is a huge mistake. It’s intuitive that a tech company’s core competency is the technology, so its engineering division should be in-house. Programmers shouldn’t be valued just only for writing code, but should be seen as contributors to the company’s future vision. Engineers are paid a third of what they’re paid in Silicon Valley, and this will hurt startups in the long run. Once the backbone of Singapore’s economy, engineering is seen as less glamorous through the eyes of Millennials. This isn’t a criticism, and it actually makes sense to me. Finance and economics are the reasons Singapore even got to the international limelight, so it’s understandable that there is such an intense focus on finance. In addition, government policies that drive growth in the financial industry allow quick transactions, attracting a bunch of expats to base businesses here if they aren’t yet enticed by MNCs (mostly banks or financial services corporations) offering hefty relocation packages.

Geography influences network.

  • Its excellent transport system overrides the ridiculous cost of getting a car here (costs 4x as a car in the US). You can bus from one side of the island to the next in an hour and a “jam” is considered laughable in this LA native’s mind. However, the geography influences who you meet, and thus this leads to easily meeting new people and tight networks. This enables new entrepreneurs to build the social capital they need to fit into the inner echelons. For example, I arrived knowing no one last July, but by the end of summer, I saw my network expand to over 300 direct connections. I wasn’t even working with a startup back then, so those were just interactions made at after-work events. There is really a huge opportunity to build the network you need to support entrepreneurial activities.

Social Circles

  • Singapore is tiny, and so are its social circles. You eventually run into the same people at startup events, or can easily get an intro to a high-ranking executive. I’ve found these “movers and shakers” to be extremely welcoming. In developed ecosystems like Silicon Valley, there tends to be a social hierarchy in which the top CEOs and VCs are difficult to access, probably due to a flood of requests for meetings and intros. However, in Singapore, there seems to be a lack of noise in the ecosystem, which has kept people open and responsive. It’s very likely that I have many 2nd-degree connections to the local unicorns, and can access the founders if I really wanted to. Once I name-drop in a conversation or mention a mutual network, it immediately gives me credibility since the receiving end would already have heard of the person. I think there’s a level of transparency in the system, and I find people to be quite genuine and trusting. Everyone wants to meet up (something about doing business face-to-face in Asian culture, perhaps) or show me around or demonstrate some sort of hospitality. This enables entrepreneurs to easily build a strong network of devoted mentors and advisers.


  • There were five full-time employees in the office at my startup, and thus five different nationalities. I appreciate that Singapore has such a diverse population and is the first country I’ve heard of that recognizes each major religion’s public holidays. Having a diverse team from the get-go may be useful when a startup is expanding regionally. No matter what nationality, I observed that there is some universal pride and respect for Singapore. I’m not suggesting that it’s populated with a bunch of chauvinists, but it seems like Singaporeans have more national pride whereas us Americans have a lot of individual pride. Maybe it’s the Asian collectivist culture or the heavy government invovlement, or the amazing feat of going from a third to first-world country in 50 years. Their trust and loyalty to one’s own country is actually quite admirable, whereas whenever patriotism comes up in America, it’s mostly associated with criticisms, tongue-in-cheek memes, or ridiculous #Murrica hashtags.

It’s difficult to see if an economies of scale model could work here, a la Walmart or Costco. Startups can reach a local maximum here, and perhaps if they’re really good, they can achieve a regional maximum. But what is the likelihood that a startup can scale internationally and reach a global impact? How do we improve the conditions for disruptive companies if there’s low adoption and no product-market fit? Because essentially in order to compete on a global scale, Singapore will need to push itself in new avenues and focus on future innovation. But who am I to dictate that what Singapore really needs is more “disruptive companies?” Maybe if the market’s not there, than it’s counterintuitive to push consumers to adopt what they don’t know they want. If Singapore doesn’t have the capabilities to replicate Silicon Valley, then maybe that shouldn’t be its true intention. Perhaps it ought to play to its strengths as a hub for startups by bringing in winning innovations and attracting overseas successes to come over, riding on already validated ideas. But how can Singapore renew itself then? As John W. Gardner wrote, “A society whose maturing consists simply of acquiring more firmly established ways of doing things is headed for the graveyard — even if it learns to do these things with greater and greater skill.” Is Singapore building its own gilded cage, and is that a good or bad thing to the startups of the future?

Thanks to all my Singaporean friends for proofreading this essay!

Starting a Startup in College

School is a runway for the amazing life you're about to have, so you've got to make it count. Founding my own business in high school and college was the most rewarding way to spend my school years. I've always had a desire to make the most impact that I can, and I'm driven by my curiosity and fascination of the world around me. When I was a freshman in high school, I felt that the scope of activities in school were too limiting and low-impact - I wanted to contribute to something that was beyond campus borders. Thus, I founded a nonprofit for human rights  and worked with activists around the world. We got a few awards and a Do Something grant to promote art therapy for former victims of human trafficking. I went to a public high school with a lot of first generation students, and noticed that their ambitions were mostly confined to less riskier career paths. Although I didn't know enough about entrepreneurship at that time to see it as a viable career option, I reasoned that starting a company while in school was at worst a learning experience and at best a great story to tell. Working on my own company really reminds me of how little I know, which drives me towards self-improvement. I was about 15 years old at that time, and this side project allowed me to think creatively and learn about the importance of creating and maintaining relationships. These lessons carried on to college, when I founded an e-commerce business right after I graduated from high school and later on, a social enterprise that took lab inventions to developing communities abroad. Below are some of my key insights that I thought were most valuable. Founding a company in college is a great way to build your network and stay motivated if you're an ambitious person. Forget frat parties, soulless internships, and other distractions. Start early, think big, and keep your ego in check by failing often. Seek out impactful, purposeful areas where you can disrupt the industry. Here are my most rewarding takeaways from starting a startup as a student.

1. It's the best career preparation ever.

Forget interview workshops and boring resume sessions. As an entrepreneur, you are constantly pitching, presenting, and getting immediate criticism. In my first interview with a national publication, I was so nervous I felt like fainting and could barely speak properly. I had to meticulously prepare for every interview after that experience. However, you really will improve over time with the more practice and support that you get. Your confidence, weaknesses, strengths, charm, and intellect are challenged when you're showing someone your passion. You're open and vulnerable, and it will teach you an incredible amount about yourself. Communicating your ideas require clarity and the ability to connect topics. There isn't a more self-revealing experience.

2. It reminds you of infinity.

CALVIN: If people sat outside and looked at the stars each night, I’ll bet they’d live a lot differently.

HOBBES: How so?

CALVIN: Well, when you look into infinity, you realize that there are more important things than what people do all day.

College can feel like a suffocating bubble with little resemblance to the real world. Projects give you purpose, and nothing gives you more enthusiasm for the future ahead than the potential of your company and how you will lead it to achieve something bigger than yourself. As a college student with an overload of classes, I felt like it was very easy to burn out, especially when I was studying 80 hours a week. However, working on a passion project that may turn into a company was my favorite pastime in college, and gave me the drive to work harder. 

3. It gives you a global perspective.

No startup can grow in seclusion. An entrepreneur thrives in the company of others, and as a founder, you will have access to a global network of ambitious young people. Brilliance begets brilliance. This is my favorite quote from Seth Godin: "Who you hang out with determines what you dream about and what you collide with. And the collisions and the dreams lead to your changes. And the changes are what you become. Change the outcome by changing your circle." Surround yourself with well-traveled, cultured, experienced, ambitious, tenacious young people. With the rising culture of conference-hopping among young people and many entrepreneurial networks, there are countless opportunities to network and get involved. I've met some of my closest friends at conferences and built long-lasting relationships from these seemingly trivial connections. 

Thoughts from Working in a Startup

The test of a good CEO is how one responds under immense stress. I believe that is the most important behavior to observe that determines a CEO's capabilities and limitations. When you don't have much runway left and customers hate your product, it can feel like daily failures are chipping away what's left of your self-esteem. Negative feedback on your product may be interpreted as a personal attack, as founders invest financially, personally, and emotionally into their ventures. I've read countless articles on the traits and habits of successful entrepreneurs, but I think experiencing working in a startup is truly a fantastic learning experience. It has really educated me on the realities of leading a company and how I can imagine it to feel when stakeholders are breathing down your neck, pressuring you to deliver.  

This summer, I interned at a Singapore-based startup that has been operating for three years. They have raised over SGD $4 mm in angel funds, won multiple awards, and is a proud example of local Singaporean innovation in the SME landscape. The small team of four people (excluding myself and a part-time assistant) inhabits a small office space, sharing a floor with another well-known Singaporean startup called XMI. In my internship experience, I learned:

1. Passion

There's no one better than yourself that knows how passionate you are about a subject, despite any attempt to broadcast your burning desire to the world. What's interesting is that the passion I feel personally for my own projects is different than the passion I see that other people have. When I'm passionate for my own venture, I never actually say outright that I am passionate in it. I'm not conscious of this passion, but I see it as an interest that I want to develop. My personal belief is that passion is something developed from grit and experience, so to say I am passionate about a new idea would be presumptuous. The definition of passion is compromised when I apply it to myself. However, when I observe how passionate others are in a venture, I witness how this is the basis for their motivation and the lifeline with which they hang onto. Their conviction is contagious and motivates employees to drive the vision forward. When our CEO pitched a VC virtually, it felt lackluster and dry. The investor seemed superficially interested, but did not make any action to move forward. However, our CEO pitched the same VC in a face-to-face meeting, the VC was incredibly enthusiastic about driving the deal forward. This is why VCs value conviction in founders and look for a passionate team in early-stage investments. It's not the actual recognition of a passionate CEO (though that's part of the puzzle), but it's the fact that this certain CEO's passion can spark something in yourself. Only when passion is demonstrated by others can we recognize the value of it ourselves. We understand passion better through someone else than on our own. 

2. Job titles are fluid.

This isn't a new discovery, but it may be difficult for some to understand that in a startup, you may be asked to deliver on things outside your domain. In fact, I believe the reason why I was hired was because I was able to understand both technical and business principles. Even though you aren't asked directly, it's good to keep in mind since it allows you to brainstorm more that you can do for the company. It's all a part of the learning process, and I've found that the key to offering valuable work is to make speed and quality as habits. To me, the worker that gets the job done in a few hours is more valuable than one who burns the midnight oil just for the bragging rights of how much time you've invested. I noticed that being fast and efficient allows me to learn faster - I don't have to be an expert in it, but I just need to be conscious of how much I need to know and what I need to know. Thus, these habits enable me to switch between different roles quickly. If we restrict ourselves to titles and descriptions, it's very easy to overlook the additional value we can offer and bypass new learning opportunities, which are the most exciting parts of working at a startup.  

3. Balance uncertainty.

Leading a team is incredibly difficult. Moreover, when you're not sure yourself of what the startup's next step is, how can you assure enough certainty in your employees without being deceptive or too certain? I think there is a general level of tolerance for uncertainty. If there is too little certainty, than employees will not have enough confidence in your ideas to efficiently execute and will quickly lose any motivation. They will feel like they are excluded from the discussion and feel like the organization is not transparent. If there is too much certainty and you under deliver, than you are essentially writing checks you can't cash, with each time there's a bounced check, an employee loses some trust in you. Certainty and more importantly, how you communicate the company's well-being, is in line with how motivated employees are.