Poker + business + applied lessons from Nassim Taleb

This summer, a casino opened up right by Boston. And I’ve swung by a few times to play Texas Hold’em — low stakes cash games.

As mentioned in my Liar’s Dice article, I love games that involve incomplete information, strategic deception, and reading people. Pokers offers an exciting challenge that complements my career.

As a start-up CEO, I’m constantly communicating with people via meetings, calls, emails — etc. At a poker table, it’s nice to be able to just sit back, relax, gather insights and make quick decisions.

Poker, like investing — is a highly analytical, solitary affair involving incomplete information — and it certainly embodies parts of my old hedge fund job that I miss.

How I play poker

My playing style is very much aligned with my personality.

I try to be very disciplined.

In general, I try to limit my losses, and really press my advantage when I have it.

At the poker table, what this means is that I will slowly lose small amounts of money, on average, for an extended period of time. And once in a while, the losses will be punctuated by a big win that will more than make up for everything.

For those of you who’ve read Nassim Taleb– this strategy should sound somewhat familiar. Taleb wrote in The Black Swan about how he became financially independent. His investment strategy was to lose money year after year. But when a previously unthinkable event happened, i.e. the 2008 financial crisis — BOOM –he made back his losses manifold.

So an hour in my shoes at the poker table might look something like this.

This is a relatively volatile strategy, but what is unique is that it is only volatile in one direction. (High Sharpe ratio, low Sortino ratio)

There are generally only positive surprises. And that is exactly what I want out of poker and in general, what we all want out of life … right?

To my knowledge, no one else plays cash poker like this. And this strategy is working out decently for me so far. Perhaps it won’t work at higher stakes tables — but we shall see.

Business — the most complex and exciting game of all

The concept of stomaching small losses and doubling down when there is a clear advantage is uncannily similar to my own business experience.

At DeepBench, we are constantly running little experiments. Sometimes they work, sometimes they don’t. We have a core business model that enables us to experiment. You can think of us as one big stack of poker chips, and we are at the table making bets.

Sometimes our experiments open doors for us and lead to areas where we want to double down. Or we are forced to do so by necessity. When the odds are in our favor — we are always prepared to go all-in with our chips. (Note, this experimental mentality is a hallmark of Amazon’s success.)

One key difference between business vs. poker decisions is that there are more things we can do in business to stack the odds increasingly in our favor. And sometimes, we can choose an entirely different game to play.

That is what makes business a much more complex and exciting game for me.

So while the stakes for running a start-up are far higher than your average poker game, ultimately, my philosophical approach to both business & poker is one and the same.

Work life harmony + freedom

About a year ago, my friend and VC investor Li Jin told me that she doesn’t believe in work life balance, but rather — she embraces work life harmony. Her words resonated strongly with me given the lessons I’ve learned from studying Warren Buffett.

For me, work life harmony means merging the professional and the personal so that work and play become one and the same. The beauty of this approach is that you will never be bored.

In contrast, I have another friend who like myself is a startup founder who likes poker. She is quite good at it — far more so than me. However, she does not tell people she plays, because she is afraid of what people like her employees & investors would think.

I can see this friend’s point of view and respect it — but I have a different approach. For me, the only way to be happy is to be free. For me, freedom requires authenticity & transparency — and that come with a risk. But as Nassim Taleb says:

I try to be purposeful with how I spend my time. And I feel fortunate to have a found a hobby in poker that aligns well with my strengths & long-term goals.


About the author: Yishi is a former hedge fund investor and current entrepreneur who enjoys thinking about businesses in his free time.

He is the CEO of DeepBench. We connect users with experts on any topic in any industry, and we also license our software to enterprises to better unlock expertise internally. (Check us out if you are interested in joining our network or using our product!)

Jack the Driver + The Bali Private Transportation Market

I recently visited Bali and had pre-arranged for a driver to take me from the airport to my hotel. This was a 2 hour trip, and I used the opportunity to get to know my driver Jack and his line of work.

riding in Jack’s car

Jack comes from a family of drivers. He has 3 brothers – all of whom drive tourists for a living. Net of nearly all costs, Jack makes $USD 4,800 a year – which is in-line with Balinese GDP / capita . Interestingly, he is unemployed half of the days of the year, and his biggest challenge is finding customers.

Why hire a private driver?

Transportation is not something I usually bother booking ahead of time, but Bali is a special case.

This is part of the reason: As you exit the airport you are swarmed by people with signs.

This certainly feels a bit overwhelming in what should be a tropical paradise. So it’s nice to be able to have a personal driver meet me inside the airport.

In every other part of the world, I’ve used Uber or the local equivalent. Bali is one of the few places where I’ve hired a dedicated private driver – for 2 main reasons.

  • Reason #1: Bali is a big island, and there are lots of places to explore. As a tourist, if I Uber over to some distant waterfall, who will drive me back? Will there even be cell phone reception? What if my phone dies? Hitchhiking no longer feels as exciting to me at age 29 as it did at age 21.
  • Reason #2:  It’s fun to build trust with someone from a different culture and learn new things. It’s nice to meet a local whom I feel safe around and who feels comfortable answering my personal questions like a) how much his car costs and b) how much he earns.

Start-up idea: daily driver booking platform in Bali

This got me thinking. What if there was a company that focused purely on providing daily drivers in Bali?

The Uber model isn’t ideal due to the aforementioned reasons.

And tour guides serve a different function than drivers. Rarely do I want a guided tour, but I will always need to get to my destination.

This potential start-up would fill the gap in-between Uber and a full-on tour agency.

Market size calculation for a private driver matching service in Bali

By my estimates – the market for matching drivers for daily trips in Bali is about $4mm annually.

While this may not be the next Uber, the beauty of this business is that all you need to get started is a smartphone & some hustle.

Simply take requests from tourists via WhatsApp, and match them to drivers via a group thread. (This was how I was originally introduced to Jack).

Acquiring both sides of the marketplace

Finding the supply is easy. I have your first 4 drivers for you: Jack and his brothers. There are 1,000+ candidates waiting at Denpasar airport any given day. Just go and speak to a few of them, size them up, select the best, and get their phone #s.

When chatting with candidates, you should screen for drivers with above-average communication skills & extrovert tendencies. As a tourist, Wikipedia can tell me all I really need to know about the temple I’m visiting. But if I want to learn about the nuances of local culture + economy, nothing beats chatting with a local!

Finding demand will be harder. The first thing I would try is to go to the smaller hotels and offer them 5% to refer guests to your private driver service. The big hotels have their own full-time drivers already, but many small hotels, including one I stayed at on this trip, don’t offer anything in the realm of transportation. Partnering with you would be a win-win proposition.

Vacation-home owners / managers would similarly be a good target. Perhaps you could even partner with AirBnb directly.

Overcoming disintermediation risk

Why wouldn’t drivers and tourists just go off-platform? There are things you can do a) immediately and b) in the future to reduce that risk.

  • Things that encourage tourists to stay with the service
    • Offer roadside assistance: customers receive comfort knowing that a 3rd party is watching over them and can help if issues arise
    • You can collect emergency contact info + address any special requests, i.e. allergies
    • In the future, you can take credit card payments up-front to help consumers a) avoid the hassle of cash and b) receive the benefits that many card-issuers offer such as trip protection.
  • Things that encourage drivers to stay with the service
    • Your 15% commission is much more reasonable than Uber’s 30%. And because this is such a capital-light model (no need to hire engineers for some time), you can afford to scale with a lower take-rate.
    • Make it clear that the more rides drivers do via your system, the more future business you will send their way
    • In the future, you can build-in a rating + review system to further strengthen the marketplace network effects

In conclusion

  • The global middle class is expanding. Independent travel is increasing.
  • At least in Bali, there is an imbalance between the supply & demand of private daily drivers.
  • The gap between Uber and full on tour agencies represents an opportunity not just in Bali but perhaps beyond (Koh Samui, Phuket?)

I really hope that someone out there reads this and gives the idea a shot.

At the very least, I’m sure you’d have fun. After all, there are far worse places to work in the world =)

Alamdhari Resort, Sideman where we stayed in Bali
A couple buddies and me hanging out!

Let me know how it goes!

Author’s note 10/20: I have been informed that Grab (Uber equivalent in SE Asia) does offer daily driver bookings. So while such competition creates challenges, it also validates the market opportunity. There could still be an opportunity for a focused, standalone service to provide a better user experience.


About the author: Yishi the co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better unlock expertise internally. (Check us out if you are interested in joining our network or using our product!)

The Mystery of Mom’s Medicine

A few weeks ago, my mom and I were chatting on the phone when she brought up something perplexing.

The backstory

A few months ago, my mom goes to her doctor for a routine appointment.

Her doctor prescribes medication, and she goes to a nearby pharmacy – Walmart –to get the prescription filled

At Walmart, based on her insurance + medication:

  • She has to pay $10 out-of-pocket per refill
  • She can buy 30-day refills, but not 90-day refills

A few days after my mom buys her medicine from Walmart – she starts getting letters in the mail from Walgreens – a competing pharmacy chain.

The first letter or 2 she ignores.

“Typical junk mail”, she thinks.

But then she notices that Walgreens is advertising their 90-day prescription refill capabilities.

Amazing – this is exactly what Mom is looking for! She can save $20 every 3 months as well as a decent chunk time if she goes with the 90-day option.

But then she wonders to herself: “How does Walgreens know that I am in the market for a 90-day prescription refill?”

Moreover – what is particularly unsettling was that Walgreens had printed the EXACT NAME of her medication on their advertisement.


Unraveling the mystery

By this point on the call, I am intrigued, and I am ready to help Mom unravel this mystery. So we start a process of elimination to uncover the truth.


Was Walgreens doing a mass market campaign? And the timing just happened to coincide with my mom’s doctor visit?


She had never received prescription-related mail from Walgreens before. The timing was too uncanny, and seeing the exact name of the drug on the letter pretty much rules out the possibility of a random mass-market mailing.

She was certain that Walgreens had access to her private medical data. But HOW did they get it?


Could someone at her doctor’s office be selling patients’ private info to Walgreens?

Very unlikely.

Multiple people across many organizations would be breaking the law at a massive scale. If it was just one doctor’s office, it isn’t worth it for any small group of employees at Walgreens to bother. If multiple doctors’ offices are involved, the level of coordination would become even more difficult.

In any case, the risk-reward tradeoff wouldn’t be worth it for anyone involved.


What if Walgreens had inserted a spy within Walmart to engage in corporate espionage?

Slightly more plausible, but still very unlikely given the risk-reward tradeoff. There are far easier, legal ways for multi-billion $ companies to make money.


Arriving at the conclusion

Within minutes, my mom and I have ruled all the possibilities that came to mind – from the reasonable to the outlandish. By process of elimination – I am 99% certain of how my mom’s private medical data ended up in a mail-advertisement.

My degree of confidence is largely informed by my previous experience as a hedge fund investor. I had done extensive research on the Pharmacy Benefit Management (PBM) industry.

PBMs are the hidden middleman that sit in between American patients, pharmacies, and employers. A simple way to think of PBMs is “insurance specifically for medications”.

I took a look at the letter that my mom had received. Sure enough, while Walgreens’ logo is on  the bottom right, the logo on the top left as well as the signatory is OptumRx — one of the 3 major American PBMs that control 70% of the market.

Each PBM has “preferred” pharmacies that it likes to work with. These preferred pharmacies receive better deals from the PBM, and can thereby offer better terms for that particular PBM’s patients – such as 90-day prescription refills.

My educated hypothesis is that Walgreens is a preferred pharmacy for my mom’s Optum prescription plan, whereas Walmart is not. And when my mom’s prescription was filled at Walmart – Optum automatically enrolled her in a mail-marketing campaign.

Therefore, I strongly suspect that Walgreens never had access to my mom’s data.


Why this matters

While our journey didn’t result in a Hollywood-worthy tale of espionage, the resolution of “The Mystery of Mom’s Medicine” raises some lingering questions about just how complex the American medical system is. I’d love to know:

  • Why doesn’t Walmart join Optum’s preferred network? Why doesn’t every pharmacy join every PBM’s “preferred network”?
  • How are those special “preferred pharmacy” deals structured?
  • What kind of kickbacks happen behind the scenes?
  • Why is everything so opaque?

Another fascinating implication is what mega-corporations do with our private data and the lopsided power that they wield.

I’m sure that at some point, my mom signed some sort of agreement allowing Optum to send her mail advertisements.

But we sign so many agreements nowadays it’s impossible to keep track of it all, and it’s impossible to think through all the implications. So when my mom received unsolicited mail advertisements with her private medical information from a company she didn’t recognize (Optum)– she found it rather unsettling – and she assumed that Walgreens had her private info.

Despite Mom’s initial unease, to Walgreens & Optum’s credit, their marketing efforts worked! And my mom is now a happy customer saving money using Walgreens rather than Walmart to fill her prescriptions.

My mom’s story is a mere microcosm of what is happening across the world, and especially in the tech sector. Today, there is a lot of political scrutiny around the Facebooks, Amazons and Googles of the world and the power that they wield in our daily lives. But in reality, this is happening in every industry and every geography, and there is no avoiding it.

The fact is, we now live in a world where privacy is fleeting and data is cheap. Not only do I think resistance is futile, but I think that the tradeoff is well worth it for the average citizen.

Walmart is a $320bn market cap behemoth. United Health (the health insurance parent company of Optum) is not too far behind at $240bn. And Walgreens clocks in at a respectable $50bn. And you know what . . . I quite enjoy seeing these gargantuans battle it out to save ordinary folks like my mom $20 every 3 months.



About the author:  Yishi the co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better unlock expertise internally. (Check us out if you are interested in joining our network or using our product!)

Unlocking Serendipity at Conferences & Events

Last month, I attended a 3-day conference focused on education & the future of work. There were 3,000+ attendees – and I barely knew any of them.

So of course, I did my homework. I spent hours browsing through hundreds of individual profiles, thought carefully about who might be interested in what I’m doing, read up on a select few attendees, and crafted and sent dozens of personalized cold emails.

Thanks to my legwork and a couple folks who did the same by reaching out to me, I had set up a few meetings in advance. And overall, I enjoyed a fantastic conference.

And of course while there, I met some people serendipitously as well. However, for every individual with whom I had a meaningful conversation, just based on sheer volume, I estimate that there were 10 missed connections.

I wish conferences & large events as a whole were structured a bit differently.


The Problem

You’ve probably experienced this before. You are a newcomer at an industry event / conference. You want to meet people, but it can be overwhelming

Take the happy hour mixer. The free food & booze is always great. After all, who doesn’t like Coronas and shrimp cocktails? (As they say, everything tastes better on a stick!)

At a mixer, by default you try to glimpse at name cards and appearances, size-up the context a bit, and try to approach people who seem open and friendly.

More or less, it’s a stab in the dark – you might meet someone who changes the direction of your business & career. More often than not, you make an acquaintance, who while a perfectly wonderful person – has different interests than yourself. Both of you realize this, so you engage in a few minutes of polite small talk before moving on.

For the most part, I do enjoy that randomness and excitement, but our time is a valuable thing. And I’ve long thought that there must be a more efficient way to maximize the value of connections created and increase the overall level of serendipity.

I doubt that my experiences & sentiments are unique.

As a whole, I wish conferences and events would do more to create connection between the attendees. And I think that there are some simple things that can be done that would add enormous value.


The Solution

The next time I sign-up for a conference or event, I would love to be asked (and be forced to respond to) 1 -3 of these questions:

  • What is ONE thing that you need help with right now professionally?
  • What is ONE topic that you would like to learn more about and why?
  • What is ONE interesting thing about your industry / position / career that few others know?

I’d want my answers to be made publicly accessible to other attendees via some type of web / mobile app interface. After all, wouldn’t you want others to try to help you?

And from the opposite perspective, I’d look for people I wish to connect with and try to “Give First” by addressing their stated needs as a way of getting in touch.

Not only are these questions great icebreakers, but they are actually even more valuable as a filtering mechanism. They help all parties better understand what they need, who to talk to, and what to say.

Interestingly enough, our company DeepBench helps people answer these exact same questions – in a slightly different setting. You can think of DeepBench’s system as a filter, designed to sift through millions of professionals around the world to make the connection that you need to find the information that you want.

We are starting to do some AI-powered matching at DeepBench right now. It is not yet used in the realm of large, live events – but our experience indicates that automatic matching of individuals can certainly be done. Sidenote: perhaps whoever pursues this idea can partner with DeepBench from a technical perspective.


Market Size Estimate

Not all event / conference attendees want to better connect with new people. For example, some VIP panelists & keynote speakers are too important to be bothered. Plus, many industry veterans attend these conferences with a key goal to reconnect with old friends.

I actually suspect that this is the primary reason that such a matchmaking tool isn’t widely used by conferences.

Most conferences are centered around the VIP speakers and NOT the masses. Even the organizers themselves are generally VIPs – after all, one has to be well connected to organize a large, successful conference.

My working hypothesis is that decision makers in this arena are disconnected from and do not feel the pain of a large chunk of end-users.

For the rest of us plebes & industry newcomers – we only know a handful of people at any event, and a better matching tool would be very useful.

I estimate that between 50-75% of all attendees at every professional conference would find helpful a filtering mechanism that helps make connections.

How did I ballpark that number? Simple – just start with the % of the population who are introverts and add a few extroverts like me who just want a tool that allows us to find the right people to approach.

If I were organizing a large, professional conference, I’d pay an extra $1-$3 / attendee for the aforementioned matching capability.

With something so simple, I could provide enormous value for my audience. And I could use this data to better understand my audience and improve the event year after year.

Within the USA alone, there are 200 million conference attendees annually – so this one feature represents a $200 – $600 million annual opportunity domestically.


Competitive Landscape and Path to Market

The market for corporate event apps is highly fragmented – see the Google Search results below. I’m not quite sure why that is. My hunch is that the barrier to entry is very low, there is no real network effect, and there is too much customization required for each conference for any single app to enjoy true economies of scale.

Customer acquisition costs & churn seem very high for a new entrant. So my conclusion is that this business opportunity is less viable as a standalone start-up idea, and more viable as part of an existing platform.

It would make much more sense for an existing conference / event technology company to build in-house, or an incumbent could license software to do this.  *coughs* Come talk to me if you are one of those incumbents! 😉



About the author:  Yishi the co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better unlock expertise internally. (Check us out if you are interested in joining our network or using our product!)

IDEA: Turning Liar’s Dice into the next Texas Hold’em

Liar’s Dice is one of the best games ever invented.

It is a fast-paced game involving luck, probability & bluffing. It is easy to learn – you don’t need to be particularly good at math. If you can divide 24 by 3 in your head, you will do just fine. And most 12-year-old kids should become proficient after 2 minutes of instruction.

If you are unfamiliar – check out this Wikipedia article. Or better yet, watch Captain Jack Sparrow challenge Davy Jones to a round of dice in this brief clip from Pirates of the Caribbean.

And the game itself is super versatile

  • You can turn it into a gambling game
  • Or a drinking game
  • Or just enjoy the challenge of trying to outwit your friends & the friendly banter that ensues =)

I first played Liar’s Dice in 2008, I’ve since introduced it to dozens of friends. Anecdotally, but almost universally – everyone I’ve taught has also become an evangelist.

The game is easy to understand but hard to master. It is very much so like Texas Hold’em Poker, but easier and things move much faster.

Unlike Poker, Liar’s Dice works well from an audience standpoint. Because there is constant, visible action, it is easy to cheer on from the sidelines and share in the glory.


I’d bet that in the past year, at least 50 million people globally have played Liar’s Dice. The game originated from Latin America. And you can find it played every day in hundreds, if not thousands of bars across Asia.

As a point of comparison, PokerStars was acquired for $4.9bn in 2014 – and is estimated to control 70% of the market. Which means that the market for online poker is $7.0bn give or take.

That could be the market for Liar’s Dice – if not larger. After all, both games require a similar combination of luck & skill, but one is easier to learn, faster-paced and more social.

Path to Market

There are two paths you could take to monetize this game.

Path #1: Work with brick & mortar casinos.

Casinos are open to testing new games. However, to go from concept to the pit floor, the process takes over 5 years and around $500,000 to cover various legal & other fees.

According to this article drawn from the work of Eliot Jacobson, a math PHD and one of the world’s leading experts in casino games, there are several criteria that any new casino game requires to be successful. I’ve listed what I believe to be the 4 most relevant criteria for Liar’s Dice.

However there is a catch. Even if you invested the time & money, and Liar’s Dice Casino Edition became a success, I’m not sure how defensible the core intellectual property would be. After all, Liar’s Dice dates back to the era of Pizzaro and the conquistadors (Although the exact origins are contested, it seems incontrovertible that the game is several centuries old).

You could probably design & patent a special table + camera contraption that is optimized for Liar’s Dice. This would earn you some royalties, and you could build a consulting business around it.

Liar’s Dice Casino Edition may generate billions for the casinos. However, if you were only to focus on brick & mortar casinos, my guess is that your entrepreneurial upside is capped in the tens of millions.

It could no doubt still be a great outcome, but you should just understand that such a prospect alone wouldn’t attract traditional venture capital funding. Perhaps you could obtain funding via angel investors or the innovation arms of the casinos themselves.

Path #2: Daily, free, online cash tournaments

There are already several existing Liar’s Dice apps. I downloaded the first one which had by far the most reviews, and gave it a test run.

Upon first glance, it’s actually a nice-looking, highly functional app!

It’s only been around for a few months and has an audience of what I estimate to be several thousand daily active users.

I chatted with the founder of YoAmbulante, the company which made the game, who mentioned that it was made by a team of 5 experienced game developers.

Pretty impressive, and I’m sure that his app has a lot of untapped potential.

A relatively simple experiment I would do if I were YoAmbulante (or had my own Liar’s Dice app) is to add $100 daily tournaments.

Such tournaments would be free to enter, and a different winner would win $100 every day. You wouldn’t need regulatory approval because people aren’t gambling – they are playing for free with the opportunity to win a cash prize.

Similar to HQ Trivia – this would build a habit amongst users and generate virality. And of course, there would be some spillover growth for your in-game purchases. Last summer, my friend built another gaming start-up around free daily tournaments with real cash payouts. And I saw this working up close and in real-time.

Liar’s Dice would be perfect for the daily, free-to-play, cash tournament model given the easy-to-learn, fast-paced, and social nature of the game.

Ultimate success: Becoming the PokerStars of Liar’s Dice.

In the long run, to capture the $7.0 billion opportunity for Liar’s Dice, you need a digital platform that provides gambling capabilities. This requires a whole host of new features such as collusion detection, ID verification, billing, privacy, compliance, and customer support. And of course, you would need the appropriate gambling licenses.

None of the above comes cheaply, but either Path 1 or 2 could be a great proof of concept and fund the long-term vision.


If you are interested in this area or are already working on something related, please reach out. And I’ll try my best to connect you with the resources & people you need.

I’d love to see Liar’s Dice become more mainstream – no matter who creates it. I’ll certainly play it myself. But as they say – the house always wins, so I’d rather work with the house =).



About the author:  Yishi the co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better unlock expertise internally. (Check us out if you are interested in joining our network or using our product!)

IDEA: Twitter meets Slack / WhatsApp

Problem & Vision

Twitter starts with public conversations and moves inward via threaded replies & direct messages.

What if there was a platform that starts the other way around—by focusing on private conversations with friends, with the ability to expand outward to include strangers?

 I read Twitter regularly to keep up to date and broaden my perspectives. Though I rarely tweet for the following 2 reasons:

  • Twitter is public and permanent, and the hurdle for posting is higher
  • I have many varied interests, and I want to maintain a coherent public identity

Ironically, I actually love sharing content with people via email / private chat.

As many of my friends know, it is very common to receive a message containing an article from me out of the blue. I try to be thoughtful about what I share and who I share it with, and this is how I prefer to connect with friends – based on mutual interest.

Often times, an article I send to a group or someone sends me leads to a thought-provoking discussion – a more nuanced conversation that I rarely see on social media. And I love it when that happens.

How do we create a space that enables those private, authentic discussions to occur, while expanding those circles of discussion in a way that feels natural, yet controlled and safe?

Twitter doesn’t give us nuanced controls to decide who gets to see our tweets by default – other than the heavy handed – “private timeline” toggle.

I do want to showcase my personal brand via a public-facing timeline.

I also want to host semi-private discussions that others can join via invite, and these discussions should not be publicly visible.

To use a concrete example – I sent this February 2019 Natty Light twitter ad to several close friends, as I thought the comments were hilarious.

Our ensuing private conversations covered the gamut of:

  • What a great advertisement this was
  • How Wiener’s Circle embraces a similar brand approach, and
  • Reminiscing over college party experiences.

On a public platform like Twitter, I doubt we would have had the same type of free-flowing conversation – but I would have loved to have the ability to branch into a discussion with strangers who know a bit more about marketing & psychology. And private communications tools such as iMessage / WhatsApp do not have the UX to easily enable users to branch out.

There should be a way to encapsulate both that free-flowing feeling of private chats & the ability to connect strangers with similar interests all on one platform. 

Product test idea

If we were entrepreneurs building this from scratch, we could take the following steps to test this on Slack: 

  • Start a Slack channel, invite a few dozen close friends that we often share content with
  • Get our close friends to agree to only use Slack to share content for a few weeks and slowly invite others
  • Create a few public as well as private groups within Slack, moderate as necessary, and see if we could keep the community growing and engaged

Market opportunity

One obvious answer is that this would become an independent social media company, and WhatsApp / Twitter would be a good proxy of value creation.

However, there would be B2B potential as well. We could be a tool for enterprises to share ideas and foster collaboration across departments.


My goal for writing these posts isn’t to personally build another business. But I do think there is room in this world for something in between Twitter & Slack / WhatsApp, and I would be very excited if someone else turned this into the next big thing.

So if you are interested in this area or are already working on something related, please reach out. And I’ll try my best to connect you with the resources & people you need. It would be cool to see a new company emerge rather than an existing tech giant dominate in this space.

Note #1: I wrote much of this in late February, before Mark Zuckerberg laid out his vision of a private, inter-operable social media platform. As I clearly agree that there is a market need here, I don’t take the cynical view that Zuckerberg is just saying this for political brownie points – though that is certainly a side benefit for him.

Note #2: Ben Thompson’s strategic analysis of this topic in Stratechery is also a great read, and I’d be much more excited to explore this from a ground-up entrepreneurial, product-design perspective.



About the author:  Yishi the co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better organize and monetize expertise. (Check us out if you are interested in joining our network or using our product!)

My Personal Mission & How I Arrived Here (Part 3 of 3)

 (Note, this is Part 3 of a 3 Part Series titled “My Personal Why”. Part 1 – Switching from Hedge Fund Investor to Software Entrepreneur, Part 2 – Warren Buffett, Charlie Munger, and the Principles of Entrepreneurship)

An interesting shaving story

A little over a year ago, I was in Las Vegas with a few business school classmates celebrating the end of the semester.

One afternoon, I found myself happily exploring storefronts along the Venetian’s indoor promenade.

I stumbled across a store called “The Art of Shaving”. The name seemed intriguing and vaguely familiar so I wandered in.

Now, my shaving habits are pretty simple. I use a mass-market razor and buy cartridges & cream in bulk from Amazon.

As I entered The Art of Shaving, it was like entering a different world. I was blown away by how complex shaving could be. There were so many blades, brushes, and ointments of all sorts – I felt overwhelmed.

Luckily, the store wasn’t very busy, and the saleswoman was ready to help. We chatted about their products for a bit, but soon the conversation migrated toward their business model.

Among the things I learned were:

  1. Procter & Gamble (owners of Gillette) bought The Art of Shaving nearly 10 years ago.
  2. Some of the store’s best revenue generators and highest margin items are razor cartridges. (And of course, they only sell Gillette cartridges.)

That was fascinating to me. Within the store (and as I would later discover online), the Art of Shaving advertises everything but its cartridges – which makes sense, since the store bills itself as a high-end brand, and the cartridges that they sell are pretty much the same ones you can buy at CVS.

It surprised me that despite all the fancy oils, creams, and gels that the brand advertises – the basic razor cartridge is still one of their biggest money-makers. And it made me think again about why Dollar Shave Club was so disruptive.

I also hypothesized that Procter & Gamble bought The Art of Shaving in 2009 to lock down a premium distribution channel and ward off potential competitors to its cash cow cartridge business. The saleswoman agreed with me – but who knows if we are right.

Ultimately, the conversation lasted a good 30 minutes. I walked out with a $28 bottle of shaving oil – partly because I felt the need to reciprocate for the saleswoman’s time and insights.


Where my mind wanders

Now I do this a lot. I’m not talking about buying boutique consumer products, but rather the act of asking everyone – from friends to strangers about business models and unit economics.

To paraphrase one of Paul Graham’s essays: It is important to pay attention to where your mind wanders when it’s free.

Well, this is where my mind frequently wanders—on vacations, on airplanes, at dinners—anywhere, anytime.

When socially acceptable, I try to steer conversations in the direction of business topics. I do so because I’m constantly seeking to better understand how the world works, and things become just a bit more REAL when the exchange of money is involved. With real stakes on the line, you truly see how incentives and human psychology come into play, and I find it all very exciting.


But what else

While I feel fortunate to have recognized this facet of my personality, that alone isn’t specific enough for me to figure out what I want to do with my career in the long-run.

I know I can grind away and get work done and motivate my teammates to do the same. But I also know that I don’t enjoy leading in such a manner, and it won’t be scalable as I grow older.

What I do enjoy, however, is curiously inquiring (like to that saleswoman), understanding people’s needs, and crafting creative deals.

It also makes me genuinely happy to connect intelligent and motivated people. (Fittingly, I co-founded a business that connects expertise.)

Much like how my mind often wanders toward business topics, it is also on the lookout for potential intros. And I have a tendency to act on those thoughts. My rationale is that, after all, 15 minutes of effort from me crafting emails could change the course of 2 people’s lives and lead to something that could change the world.

As an example, I was at a friend’s wedding last month where the bride told me that her mom is the global head of corporate travel for a prominent tech company. My thought immediately went to my friend Alex Jara who is working on an innovative travel start-up called Deal Engine that should be of great interest to her. I laid the groundwork, and when the time is right, I’ll make that intro.


Putting it all together to arrive at my personal mission

In thinking about what I want to do with my life, I try to take a pragmatic approach.

I recently made an effort to triangulate to the intersection of a) what I am good at, b) what I enjoy doing, and c) what is good for me in the long run. And I’ve come up with this diagram.

I’ve concluded that my personal mission will be to connect people to capture business opportunities together.

I’ve decided that I will use this blog as a means of broadcasting business ideas + my own analysis + personal anecdotes with the explicit goal of connecting people. I will continue to write about things I find interesting, and I will go out of my way to connect those who also find those topics interesting.

I can see how this could evolve into an investment vehicle down the road (and perhaps even merge with my current company), but for now, I will just do it for fun – in my free time.

I should mention that I don’t need to be the person to come up with these future ideas. As everyone knows, ideas are a dime a dozen, it is the execution that is hard – and my goal is to help people execute in the way that feels most natural and fun for me.

So if you think of a business opportunity that you wish to share publicly—let us discuss, and I may write about it! Together, we can spread the word and help you find the right people to connect with!



About the author: Yishi is a former hedge fund investor, current entrepreneur & MBA grad who enjoys thinking about businesses in his free time. He can be reached via yz [at]

He is also a co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better organize and monetize expertise. (Check us out if you are interested in joining our network or using our product!)

Warren Buffett, Charlie Munger, and the Principles of Entrepreneurship

Over the years, I’ve invested hundreds of hours in trying to absorb the worldly wisdom of Warren Buffett & Charlie Munger. (Saved here are the best Munger / Buffett materials that I have come across– please feel free to read, learn and share!)

The core tenets of Buffett and Munger have profoundly shaped the way that I approach life, and below are 4 of their key principles that I believe are most relevant to entrepreneurship.

 (Note, this is Part 2 of a 3 Part Series titled “My Personal Why”. Part 1 – Switching from Hedge Fund Investor to Software Entrepreneur. Part 3 – My Personal Mission & How I Arrived Here)


Principle #1: Circle of competence

“Intelligent investing is not complex, though that is far from saying that it is easy. What an investor needs is the ability to correctly evaluate selected businesses. Note that word “selected”: You don’t have to be an expert on every company, or even many. You only have to be able to evaluate companies within your circle of competence. The size of that circle is not very important; knowing its boundaries, however, is vital.”   

– Warren Buffett, 1996 Berkshire Hathaway Annual Letter

For entrepreneurs, our circle of competence comprises of all the resources that we have available.

Within one’s own circle of resources – somewhere, there needs to be some advantage.  It doesn’t have to be a huge advantage. It could be as simple as one or two key insights – combined with your skills, your network, your reputation, and your energy.

Here is a concrete example from my personal experience — at DeepBench, the start-up that I co-founded in business school, we targeted an industry that we were very familiar with. We combined our insights, experience, and grit with the resources that MIT had to offer.

Over time, we built on those limited resources that our start-up possessed, and our circle of competence grew to where we are today.

Buffett uses the following baseball analogy to reiterate this concept:

“We try to exert a Ted Williams kind of discipline. In his book The Science of Hitting, Ted explains that he carved the strike zone into 77 cells, each the size of a baseball. Swinging only at balls in his “best” cell, he knew, would allow him to bat .400; reaching for balls in his “worst” spot, the low outside corner of the strike zone, would reduce him to .230. In other words, waiting for the fat pitch would mean a trip to the Hall of Fame; swinging indiscriminately would mean a ticket to the minors.

 . . . 

In investing, I’m in a no-called strike business, which is the best business you can be in. I can look at a thousand different companies, and I don’t have to be right on every one of them or even 50 of ’em so I can pick the ball I want to hit. And the trick in investing is just to sit there and watch pitch after pitch to go by and wait for the one right in your sweet spot

— (Paragraph #1 – 1997 Berkshire Hathaway Annual Letter, Paragraph #2 – Becoming Warren Buffett – 2017 HBO Documentary)

It’s clear to me that Buffet’s baseball analogy misses the mark for entrepreneurs, and it must be reinterpreted.

Where does a start-up’s circle of competence truly lie? There are so many rapidly moving pieces that make the boundaries of that circle very difficult to discern.

As entrepreneurs, we are forced to stretch the boundaries of our circle of competence far more frequently than investors are. Entrepreneurs don’t have the luxury of waiting for the perfect pitch in our sweet spot. A start-up must keep swinging and reaching for new opportunities. An entrepreneur must do things that do not feel comfortable.

I’ve personally learned to embrace the discomfort — that is the biggest mentality shift.

Entrepreneurs must sell our vision & capabilities to investors, the media, our customers and our employees. We must set stretch goals to motivate each of those constituents.

Unlike investors who are generally passive, entrepreneurs have the opportunity to create self-fulfilling prophecies. In fact, we must do so, otherwise we cannot grow.


Principle #2 Choose the right business model

Image credit: Garth von Ahnen

‘I always used to tell [Bill] Gates that a ham sandwich could run Coca-Cola. And it was a damn good thing, too, because we had a period there a couple years ago where, if it hadn’t been that great of a business, it might not have survived.” 

— Alice Schroeder quoting Warren Buffett in The Snowball (2008 Biography)

Note: Buffett disputes the context of this quote in a 2014 CNBC interview. However, I’m guessing that: 1) Buffett is backtracking in order to minimize offense and / or 2) The quote came from Charlie Munger if not Buffett, so I’ve decided to feature it with that caveat.

In any case, I think the sentiment is clear and makes logical sense. Buffett’s implicit advice is: Invest in businesses so good that morons can run them, so that you have an extra margin of safety.

To paraphrase another quote of Warren’s: When a great management team meets a tough business model, it’s the tough business model that wins. The business model is paramount.

The single most important decision in evaluating a business is pricing power. If you’ve got the power to raise prices without losing business to a competitor, you’ve got a very good business. And if you have to have a prayer session before raising the price by 10 percent, then you’ve got a terrible business.”

— Warren Buffett, 2011 interview with the Financial Crisis Inquiry Commission

As an entrepreneur, finding the right business model is easier said than done. Every market and every opportunity is slightly different. Micro-economics (i.e. customer acquisition costs, churn rates) matter. Customer personas matter.

You won’t know for sure whether your business model will work unless you invest resources to figure it out. A useful mental model to save some effort here is a concept from the investment world called “economic moats”.

Moats are essentially barriers to entry, and here are a few great examples.

If you think about it, the phrase “a start-up’s moat” is an oxymoron, given how vulnerable a young start-up is. However, to borrow a lesson from Peter Thiel’s book, From Zero to One : if you pick your market carefully, you can create your own tiny monopoly. Then over time, you use your monopolistic power within that niche to expand your moat and circle of competence.

Even if there are no barriers to entry today, a great start-up should have a credible path to creating barriers down the road.

Personally, with DeepBench, we’ve chosen a capital-efficient, network effect business model with SaaS and content components that should result in customer stickiness and a strong competitive moat in the long-run.


Principle #3 – Understand your edge and don’t be a sucker

Matt Damon’s quote above from Rounders is a poker aphorism that surfaced in the late 70’s and was used by Warren Buffett in the 80’s. This phrase has now become very popular in the investment world.

This concept is closely related to the circle of competence. The lesson here is that you have to understand what you are investing in. To bring up Buffett’s baseball analogy again: you don’t need to swing the bat unless a pitch is in your sweet spot.

Moreover, you need to know WHY the buying opportunity exists. If you think something is cheap, you better be able to explain why. Otherwise, you are the sucker at the table.

“If you play games where other people have the aptitudes and you don’t, you’re going to lose. And that’s as close to certain as any prediction that you can make. You have to figure out where you’ve got an edge. And you’ve got to play within your own circle of competence.”

— Charlie Munger, Art of Stock Picking

As mentioned in my previous article, inefficiencies exist in both the entrepreneurial and stock market worlds.

In the stock market, for every buyer, there is a seller. When you take an action, you imply that you see something that the market does not.  As a stock market investor, it takes a dose of confidence bordering on arrogance to say that you are smarter than the market.

From a psychological perspective, this is the exact same “arrogance” that entrepreneurs must embrace when taking the plunge. You are more capable than the other entrepreneurs that have failed before you, and you are smarter than the incumbents in your industry that are somehow unable to act on this opportunity that you see. You are able to do something that people with more experience, connections, and capital cannot.

To determine where an entrepreneur sits along the boundary of calculated confidence vs. delusional arrogance, venture capitalists will often ask entrepreneurs some version of: “Why you? Why this team? Why now?”

I try my best to answer that question using the circle of competence framework. I strive to understand my own edge as well as Charlie & Warren do for themselves. And I aim not to be a sucker 😉


Principle #4 – Live a life that makes sense for yourself

Not too long ago, Warren Buffett was reading a 10-Q financial filing on a Saturday morning.

He then called the CEO of that company to ask a few questions.

The CEO replied to Warren, jokingly – “Is this what you do on Saturday mornings, read 10-Qs for fun?”

Warren replied matter-of-factly, “Yes”, and proceeded straight to his questioning.

I aspire to live a life such that my day-to-day business activities do not feel like “work”. I want my Saturday mornings to feel as equally enjoyable as my Tuesday afternoons.

I want to live life with a purpose. I want to voluntarily “work” weekends and evenings, even if I had enough resources to retire and live very comfortably for the rest of my life.

That is the life that I try to lead, as well as the mentality I look for in my current and future business partners.

Over the decades, Warren Buffett has carefully arranged his life in a way that is catered to his own peculiar strengths and needs – in other words–his own circle of competence. I think that this is one of the most critical pieces to his success.

As an example, Buffett has famously described his management style as “delegation to point of abdication”– where he will often go months or even years without talking to some of his portfolio CEOs.

The environment that Buffett has thoughtfully crafted for himself affords him the freedom to do what he does best and what he most enjoys doing: Warren Buffett has ample uninterrupted time to read, think, and make decisions.

On a related note, Jeff Bezos espouses a very similar concept called work-life harmony. Bezos states that the word “balance” in the conventional terminology of “work-life balance” implies a trade-off, and that is a limiting way to think.

I agree with him.

Personally, I’m still in the process of figuring out what my own work-life harmony looks like. I do think that it is a lifelong process that requires constant reflection and adjustments, and I feel like I’m closer than I’ve ever been.

The implications of Buffett & Bezos’ life approach for entrepreneurs are clear.

Every entrepreneur is different, and every start-up is unique. We must choose a path that fits us—a path that is uniquely tailored to our strengths and weaknesses. We must craft an environment that is authentic to our working style and our life goals.

You don’t need to be a billionaire to start making tweaks to your environment and shifting your mentality. Success won’t happen overnight, but that is no excuse to not try.



If there is anything I’ve learned from Buffett and Munger, it is that their tenets are best considered holistically.

You can’t have happiness without work-life harmony.

You can’t achieve work-life harmony unless you understand your life goals and circle of competence.

Your circle of competence defines a) your edge and b) what business models make sense for you to pursue.

If you want to get better at these things, and whether you are an entrepreneur or not, my only advice for you is to read and reflect—and Buffett and Munger’s writings are a great place to start.

If this type of thinking resonates with you, I’d like to invite you to join me on a life-long journey.

Next post, I’ll discuss my own long-term goals and how I hope to get there with your help!


About the author: Yishi is a former hedge fund investor, current entrepreneur & recent MBA grad who enjoys thinking about businesses in his free time. He can be reached via yz [at]

He is also a co-founder & CEO of DeepBench — We connect users with experts on any topic in any industry, and we also license our software to enterprises to better organize and monetize expertise. (Check us out if you are interested in joining our network or using our product!)


My Personal Why – Switching from Hedge Fund Investor to Software Entrepreneur (Part 1 of 3)

(Note, Part 2 has been published: “Warren Buffett, Charlie Munger, and the Principles of Entrepreneurship“)

I enjoyed my last job as a hedge fund investor. I found the work highly intellectually stimulating.

Being an investor aligned well with my lifelong desire to better understand how our world works

But I felt like something was missing.


Ultimately, I switched career paths and became an entrepreneur for 3 key reasons:

Reason #1 – I want to better understand business operations and the nuances of management in order to become a superior investor in the long-run.

Reason #2 – I am at the right stage of my life to take a risk. I have no kids, and my parents are doing OK financially and health-wise. From a personal perspective, I can afford a career reset if all goes south.

That is my personal Margin of Safety.  Nevertheless, I wouldn’t have made the career switch if I didn’t think that the decision would be positive Net Present Value (NPV) — which brings me to the last and most important reason.

Reason #3 – I believe that the long-term, risk-adjusted NPV of being an entrepreneur is higher than any other course of action I could have taken. This is somewhat of a contrarian view, so I will use this post to explain in detail.


I’m going where the market inefficiencies are.

As a former investor, I know that markets are inefficient for good reason. There are more unknowns, less liquidity, and more risks. But I firmly believe that if one is willing to do more legwork to address those risks, then the best returns can be found in the most inefficient markets.  

The above diagram illustrates my assertion that the best opportunities of all are found markets in which no company exists yet.  And the table below illustrates how I think about the similarities and differences between being an investor vs. entrepreneur.

Clearly, the critical process of execution is very different for an investor vs. an entrepreneur, as are the skills required to succeed. However, I assert that the high-level conceptual framework is the same.

After all, both entrepreneurs and investors look for market opportunities and capture them – the method of execution just varies, depending on how involved you want to be. Either you sit and wait (buy-and-hold hedge fund investor), or you actively build new products to serve customer needs and find more of those customers (entrepreneur). And there is everything in between (activist hedge funds, turnaround private equity shops, hands-on VCs).

Ultimately, just as hedge fund managers arbitrage market inefficiencies to generate “alpha”, so too do companies eliminate market inefficiencies by delivering value to customers. The way all companies (not only start-ups) generate “alpha” is to just keep a slice of that value created for themselves.  This is illustrated by the simplified diagram below, using Uber as an example.

Seeking like-minded people

In conclusion, I want to go where the most inefficient markets are, deliver enormous value to our customers, and capture a slice of that value for myself and my business partners, and I want to do it at scale.

Based on my conversations with other entrepreneurs and investors – I feel that very few people share my philosophical approach and see the same link between entrepreneurship and hedge fund investing as I do. If you are one of the few people in the world who thinks this way – please reach out to me!

(Part 2 – Warren Buffett’s influence on how I think about entrepreneurship, and To come: part 3 – Long-term goals and how I hope to get there (with your help!). Sign up for email updates at


About the author: Yishi is a former hedge fund investor, current entrepreneur & recent MBA grad who enjoys thinking about businesses in his free time. To contact him about this article, or suggest new future topics – he can be reached via yz[at]

He is also a co-founder & CEO of DeepBench – a company that 1) connects those who have expert insights with those who need them and 2) provides expert network software as a service. If you wish to organize knowledge within your enterprise as well as offer that expertise externally, DeepBench can provide the tools to do so!

Business Tips from David Cohen – Founder & CEO of Techstars


3 years ago, I co-founded a start-up around the concept of lease-to-own domain names. David Cohen, the co-founder of Techstars, was one of our first customers. To our chagrin . . . he was also one of our only customers!

Needless to say, that business never took off, but one great thing that emerged from that failed start-up experience is the rapport that David and I developed. I have had the privilege of receiving entrepreneurial mentorship & advice from David over the years.

I wanted to share David’s wisdom and message with the broader world, so I recently interviewed him for 40 minutes and wrote a summary of my 4 key takeaways below.

(1) Complete Audio (downloadable) and (2) Full Transcript of the interview.


Takeaway #1: Self awareness

Early on during the interview, I asked David:

“Do you have any advice for people in our late 20s, early 30s, whether we’re entrepreneurs or not, in how to become more self aware of our strengths and weaknesses and act appropriately?”

In response, David says that the 2 most effective things that he has done in his career are:

  • CEO coaching.
    • “When you get a great CEO coach, or partnership coach, it’s not about the business. It’s about you and your strengths and weaknesses. That’s super valuable to have somebody that’s really great at seeing it in you and just telling you in a trusted way”
  • 360 reviews.
    • “I know those are somewhat popular now, but that’s where I’ve learned the most about myself. The growth area is where you think you’re good at something but your peers think you’re weak at it or not good at it.
    • So just having a group of people that will give you that honest feedback and asking for it, not like hey come in and tell me today, but as a rhythm, surfaces things that you realize about yourself. “

Interestingly, through 360 reviews, David realized that he was a “conflict avoider”, and that feedback enabled him to adapt.


Takeaway #2: Building to one’s strengths

When I asked David about what has made Techstars successful, he responded:

Part of [Techstars’ success] is I’ve also built it to my strengths.

I don’t want to spend time managing people. I want to spend time finding great investments, sitting on those boards, helping those entrepreneurs succeed, influencing the strategy of Techstars, but not the day to day personnel issues and whatever else that are just not my strengths.

So it’s part of this question you asked earlier about becoming self aware.

You learn what you’re good and bad at and you can work on the things you’re bad at, but you’re probably never going to be great at them.

So you sort of take that data and you build an organization that can be successful.”

This is a common theme in other business leaders I’ve studied over the years. David has created an environment that fits his strengths.

And of course, to emulate these leaders and create such an environment, we must have a good understanding of what our strengths are – which is why the first takeaway around self-awareness is so critical.


Takeaway #3: Being authentic

Building to one’s strengths doesn’t mean ignoring one’s weaknesses. I asked David about his weaknesses and he responded:

An example of [a weakness] has been selling. In my past, I never thought of myself as good at selling or building strong personal relationships with a purpose of selling.

I’ve had to learn how to do that, with general partners in our venture funds. Relationships with limited partners, who are really important to what you’re doing, really matters and selling to them really matters.

So you work on yourself even though it’s not who you are.

Techstars has a well-known motto (famous within the organization at least) – “Shut up and execute”. Given David’s comment above, I sense that such a motto is an authentic extension of David’s own personality.


Takeaway #4: Reading people

Context: I think that reading people is a critical business skill. However, relative to a business leader’s strategic prowess, their ability to read people is often undercounted and misunderstood.

I make an effort to ask every business leader I meet about how they size people up. In December 2017, I was fortunate enough to ask Warren Buffett this question (in front of a room of 200 MBA students). Buffett mainly dodged the question – but fortunately, David Cohen provides a much better answer here:

“So one of the keys to reading someone is to ask uncommon questions that people couldn’t possibly be prepared for and get a vibe.

Are they being genuine with you? Are they willing to say, “I’ve never thought about that” or “I don’t know”.

I love those answers because the best entrepreneurs will turn those into, “I don’t know so can we talk about that? That’s really interesting. I want to come away from this with something on that.

They almost forget they’re in an interview and they really just focus on making the company better. So even if something is really out there, Do they dismiss it? Do they say, “Yeah great idea, let’s go that?” Or do they say, “I want to talk about that and learn more?”


Other topics explored during interview – (1) Complete Audio (downloadable) and (2) Full Transcript.

  • Mistakes Techstars Made early on
  • Assume good intent (David’s own blog post)
  • Don’t make yourself indispensable (David’s own blog post)
  • Impact of David’s father (David’s own blog post)
  • How David thinks about investments
  • David’s strengths as an investor
  • How Techstars almost didn’t invest in Sendgrid
  • How if David had met Travis Kalanick instead of Ryan Graves, he may not have invested in Uber


About the author: Yishi is a former hedge fund investor, current entrepreneur & recent MBA grad who enjoys thinking about businesses in his free time. To contact him about this article, or suggest new future topics – he can be reached via yz[at]

He is also a co-founder & CEO of DeepBench – a company that connects those who have expert insights with those who need them. If you wish to learn about any industry in any geography, or if you want to join the DeepBench network and be paid for your insights, his company can help!