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Y Combinator Demo Day: Classes For Angel Traders

whysavetoday by whysavetoday
June 19, 2026
in Personal finance
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Y Combinator Demo Day: Classes For Angel Traders
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A part of the rationale I have been writing about distribution and the significance of finally betting on your self was to gear myself up for Y Combinator Demo Day. For these unfamiliar, YC is the biggest and arguably one of the best startup accelerator on the earth. And it occurs to be based mostly in my yard in San Francisco.

I have been a startup investor since 2002, a enterprise capital LP since 2006, and a personal firm operator since 2009 with Monetary Samurai. I’ve liked startups and the entrepreneurial life ever since spending my center faculty years in Kuala Lumpur, Malaysia. The households with giant properties within the hills, those with the views and swimming swimming pools, had been all entrepreneurs.

As an impressionable 12-to-14-year-old boy, I figured getting picked up in a black Mercedes 280 SEL with a chauffeur seemed like much more enjoyable than taking the bus. So it caught with me early that entrepreneurship was the trail to a probably higher life.

Sadly, I chickened out after school. In 1999, a household pal supplied me a job in Shenzhen, China to run his eyeglass components manufacturing unit and probably associate with him to construct his enterprise in a brand new nation. I believe he felt like I used to be the son he by no means had, as his daughter wasn’t . As an alternative, I took the “safer” route and joined Goldman Sachs as a monetary analyst within the worldwide equities division. After 7 rounds and 55 interviews, it was too powerful to show down.

However ever since 1999, I’ve carried loads of what-ifs concerning the journey I did not take. So when the world lastly crashed in 2009, I figured it was now or by no means to begin my very own factor with the launch of Monetary Samurai. YC Demo Day was, in a manner, reliving a door I closed 26 years in the past.

Why Y Combinator Is Value Exhibiting Up For

Earlier than I get into the day, let me clarify why YC is a giant deal.

YC is essentially the most selective startup accelerator on the earth. The acceptance fee is roughly 1%, which makes Harvard look straightforward to get into by comparability. Get in, and also you obtain $500,000 for about 7% of your organization, three months of intense mentorship, and a community that opens doorways most founders spend a decade attempting to pry open.

Does this system truly work? The numbers say sure. About 4.5% of YC corporations go on to grow to be billion-dollar unicorns, versus 2.5% for different venture-backed seed-stage startups. Roughly 45% elevate a Collection A, in comparison with 33% for everybody else. So far, YC has funded greater than 90, billion-dollar corporations.

You additionally might need heard of some of them. Airbnb. Coinbase. DoorDash. Instacart. Stripe. Reddit. Dropbox. YC is nice at discovering outliers early and pouring rocket gas on them. Additionally it is a superb enterprise mannequin.

So when higher odds at a unicorn are on the desk, you present up. Even when it means standing in your toes for eight hours straight, which I fortunately did from 9:45 within the morning till 5:45.

Y Combinator And Serendipity

I discuss luck and serendipity quite a bit on Monetary Samurai. I firmly consider most outsized wealth is because of luck. And my path to attending YC Demo Day is a superb instance.

Again in 2013, I performed tennis with the co-founder of a roboadvisor known as FutureAdvisor. His co-founder, Jon, occurred to be a dad at my children’ faculty in the identical grade. Jon went on to grow to be a full associate at Y Combinator in 2023.

Many founders get caught looking for the proper startup concept earlier than they commit. However the excellent concept would not exist within the summary. The one option to discover what works is to choose one, go deep, and get suggestions from actual prospects.

On this episode of Startup College, YC’s @xuster… pic.twitter.com/ID5DanKlrv

— Y Combinator (@ycombinator) June 17, 2026

Then it turned out one of many dads in my Pokemon Go group chat was a YC alum. For years we traded raid methods and by no means as soon as talked about work. Then his firm, LanceDB, raised a Collection A, and I believed to myself, why did not I help and make investments? It is just because I had no concept what he did. Please ask folks what they do, they may shock you.

After which my softball buddy, who I additionally play poker with, talked about his co-founder at AppThority was a dad at my faculty. That is how I obtained to know Domingo, whose child is in the identical grade because the son of Garry Tan, the President and CEO of Y Combinator. I first met Domingo at a first-grade dad occasion a few years in the past, and he launched me to the assorted kinds of tequila.

So with my love of entrepreneurship, my conviction that we’re heading into an AI-driven future, and YC dad and mom seemingly throughout my faculty, I lastly needed to attend Demo Day. Because of Domingo, Garry, and the YC workers for having me.

Incredible Vitality And Creativity

Incredible Vitality And Creativity

The primary takeaway is that YC Demo Day is a blast of adrenaline that makes you wish to run by way of partitions. You do not simply wish to construct merchandise that resolve unimaginable issues. You begin questioning your whole objective.

One founder I met was Marshall Gould, a researcher in genomic medication from Oxford. He is constructing Juno, an AI well being assistant for power sickness. His firm spoke to me instantly, as a result of I suffered from power again ache for 3 years whereas in banking. If I would had an AI well being assistant to assist me get by way of these days, I’d have paid nearly something to really feel higher, or at the very least not really feel alone.

Over 1 billion folks stay with circumstances like fibromyalgia, lengthy COVID, POTS, ME/CFS, EDS, endometriosis, lupus, and MS. Greater than 15% of the world lives with some type of incapacity. And the laborious fact is that as we age, most of us will face some sickness that chips away at our high quality of life. It is a market measured in human struggling, and nearly no person is constructing particularly for it.

I’ve invited Marshall onto the Monetary Samurai podcast so extra of you may hear his story instantly. It feels nice to assist founders do nice issues for humanity.

Juno AI - AI Health Assistant AI, Founders Isaac Tolley and Marshall Gould
Juno founders Isaac Tolley and Marshall Gould. Isaac waited 14 years for an eosinophilic bronchitis prognosis. Marshall lives with ME/CFS and continues to be trying to find one thing that helps. They spent the final yr conducting analysis at Oxford and UCL to grasp what makes folks have interaction with medical chatbots, to permit Juno to ask the precise questions on the proper time and comprehensively perceive every consumer’s well being.

The Competitors To Make investments Is Powerful

By the point Demo Day arrives, the businesses with essentially the most traction have already stuffed their rounds. So if you would like an actual shot at investing, it is advisable to attain out to founders one to 3 weeks earlier than. And if you happen to aren’t a recognizable angel or a VC from a identified establishment, getting in might be powerful.

That mentioned, there are nonetheless loads of superb corporations open to new buyers on Demo Day. And as each founder and investor is aware of, the primary product isn’t the ultimate product. Firms pivot and iterate always.

My favourite pivot is Slack. It began as an inner communication device for a failed massively multiplayer on-line sport known as Glitch. The sport shut down, the workforce rebranded the device, and Slack launched in 2013. In 2021, it offered to Salesforce for $27.7 billion. Not unhealthy for a facet function of a online game no person performed.

The most important funding winners are nearly at all times non-consensus. So simply since you could not get into the YC firm that grew to $1 million in annual recurring income inside six months doesn’t suggest you have missed out. The subsequent Airbnb hardly ever appears to be like like the following Airbnb on day one.

YC Demo Day with CAIS dads, including Brady, Jeff, Sam Dogen, Garry Tan, Domingo Guerra
My fellow faculty dads exhibiting as much as YC Demo Day to help nice founders. Thanks for having us, Garry.

What Angel Traders Ought to Carry To The Desk

As an angel, if you happen to aren’t writing the largest verify, or aren’t a celeb, you’d higher add essentially the most worth. The founders value backing are those you may genuinely assist. Here is what each angel ought to suppose laborious about bringing to the desk earlier than exhibiting up:

  • Distribution. Entry to an actual viewers of potential prospects, the only hardest factor for an early-stage firm to construct from scratch.
  • Introductions to prospects who match the founder’s goal profile.
  • Assist discovering the precise early workers to spherical out a workforce.
  • Introductions to different buyers for the following spherical.
  • Working experience throughout product, advertising, and growth, ideally earned the laborious manner by truly operating a enterprise.

My edge is distribution. Monetary Samurai reaches a whole lot of 1000’s of financially subtle readers each month, precisely the viewers many fintech and shopper founders need. Add 20 years of enterprise LP relationships and 17 years operating a worthwhile enterprise, and I can assist with intros, the following spherical, and the working grind.

Be Proactive And Take Initiative

From an investor’s standpoint, there are about 200 founders in every batch to trace. So you must do your homework beforehand and slender the sphere to what’s most related. Out of your shortlist, you would possibly put money into simply 10%, so it is advisable to discuss to as many founders as doable. Construct your funnel.

I had 5 names on my record out of 196, targeted on private finance, fintech, and shopper corporations the place I knew I might add worth. I had two nice conversations and reached out to the opposite three. They did not reply, probably as a result of their rounds had been already full, which is the norm for the most popular corporations by Demo Day. No laborious emotions. I consider in serendipity. If it is meant to be, it is meant to be.

A fast word on etiquette, as a result of I’ve had differing opinions on easy methods to strategy founders. Within the first assembly, I am not a fan of interrogating a founder on their ARR, margins, cap construction, and burn fee. As an alternative, I wish to construct rapport first, take heed to their story, after which observe up with the tougher diligence questions afterward, when you could have their consideration and an actual back-and-forth going. Relationships open doorways that spreadsheets cannot. However I perceive the significance of attending to the purpose since there are such a lot of selections to be made.

Then there are the founders working the room for capital. As a result of I had a purple investor lanyard, founders knew to strategy me and my companions throughout breaks, lunch, and joyful hour in the event that they had been nonetheless closing their spherical.

I admired each one of many roughly 15 or so founders who got here as much as share their story. I made a degree to pay attention, supply encouragement, and be useful. It takes actual braveness to stroll as much as a stranger and ask for one thing. As a result of if you happen to by no means ask, you by no means get. It jogged my memory of my relationship years. In case your success fee is just 5%, you’d higher ask 20 occasions to get one sure.

YC Demo Day pitch

A Very Small World With A lot To Eat And Drink

Demo Day additionally had infinite free meals and drinks, which most conferences don’t. I appreciated the unfold inside, plus all of the meals vehicles and distributors exterior. Laborious to be in a foul temper with a taco and a beverage in hand.

Humorous sufficient, I noticed the three GPs of one other seed-stage fund I am an LP in. They had been doing their very own diligence, attempting to learn the traits. Possibly they had been even there to out-compete me on a deal. Who is aware of.

The important thing level is that the enterprise and startup world is small. In order for you alternatives to speculate, you must be genuinely good. Work on that emotional intelligence. The very last thing you need is to get blackballed since you had been impolite to a founder, confirmed up 40 minutes late with out an apology, or backed out of a handshake deal.

Be good. Then be useful. The extra you assist others, the extra folks wish to enable you to.

Open To Make investments

My closing takeaway is that being a enterprise investor is difficult. We already understand how laborious it’s to be a founder who will get an organization off the bottom. Plenty of people prefer to poke enjoyable at enterprise capitalists, considering they’ve soft lives, do not must work too laborious, and are all wealthy off their 2%+ administration charges and 20% to 30% carry. However for many VCs not within the high tier, the job is an intensive grind.

The diligence required earlier than you make investments is a full-time job. For instance, roughly 200 YC corporations current per batch, and there are 4 batches a yr. No single particular person can correctly analyze all of them, so you must area of interest down and settle for that you’re going to miss a lot.

And even if you get the assembly and determine to speculate, most startups will not return your capital, not to mention generate life-changing wealth for you and your LPs. You construct your portfolio intentionally, ideally 20 to 60 corporations, assist the place you may, and wait 8 to 11 years to see outcomes.

I hope to return to many extra Demo Days and put money into extra corporations. I’ve put aside $150,000 a yr for angel investing. Let’s examine what occurs.

And if you happen to’re a founder, YC or in any other case, elevating capital and also you suppose I can assist, please attain out. My electronic mail is on the backside of my About web page, or you may depart a remark under.

Construct on!

Are any readers buyers in YC corporations or YC founders? I would love to listen to about your expertise. What share of your capital or how a lot are you allocating to investing in startups? Have you ever had any nice successes?

Need to construct monetary freedom sooner, somewhat than later? Be a part of 60,000+ readers and get my free weekly publication each Sunday morning. No fluff, no spam, simply the identical first-person insights on private finance, actual property, startups, and monetary independence I have been sharing since 2009. The whole lot I write comes from actual expertise, not principle.



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