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    Home»Finance»Y Combinator Demo Day: Lessons For Angel Investors
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    Y Combinator Demo Day: Lessons For Angel Investors

    The Daily FuseBy The Daily FuseJune 19, 2026No Comments13 Mins Read
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    A part of the explanation I have been writing about distribution and the significance of finally betting on yourself was to gear myself up for Y Combinator Demo Day. For these unfamiliar, YC is the most important and arguably the very best startup accelerator on this planet. 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 massive properties within the hills, those with the views and swimming swimming pools, have 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 regarded 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 faculty. In 1999, a household buddy supplied me a job in Shenzhen, China to run his eyeglass components manufacturing facility and probably companion 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 robust to show down.

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

    Why Y Combinator Is Price Displaying Up For

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

    YC is essentially the most selective startup accelerator on this planet. The acceptance price 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 making an attempt to pry open.

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

    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 speak about luck and serendipity loads on Monetary Samurai. I firmly consider most outsized wealth is due to 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 referred to as FutureAdvisor. His co-founder, Jon, occurred to be a dad at my youngsters’ faculty in the identical grade. Jon went on to turn out to be a full companion at Y Combinator in 2023.

    Many founders get caught looking for the proper startup thought earlier than they commit. However the excellent thought does not exist within the summary. The one strategy to discover what works is to select one, go deep, and get suggestions from actual clients.

    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 assumed to myself, why did not I assist and make investments? It is just because I had no thought what he did. Please ask people what they do, they could 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 acquired 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 varied sorts of tequila.

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

    Improbable Power And Creativity

    Improbable Power And Creativity

    The primary takeaway is that YC Demo Day is a blast of adrenaline that makes you need to run via partitions. You do not simply need to construct merchandise that clear up unbelievable issues. You begin questioning your complete function.

    One founder I met was Marshall Gould, a researcher in genomic drugs from Oxford. He is constructing Juno, an AI well being assistant for continual sickness. His firm spoke to me instantly, as a result of I suffered from continual again ache for 3 years whereas in banking. If I might had an AI well being assistant to assist me get via 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 dwell 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 exhausting reality is that as we age, most of us will face some sickness that chips away at our high quality of life. This can be 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 immediately. It feels nice to assist founders do nice issues for humanity.

    Juno founders Isaac Tolley and Marshall Gould. Isaac waited 14 years for an eosinophilic bronchitis prognosis. Marshall lives with ME/CFS and remains to be trying to find one thing that helps. They spent the final yr conducting analysis at Oxford and UCL to know what makes folks interact with medical chatbots, to permit Juno to ask the correct questions on the proper time and comprehensively perceive every person’s well being.

    The Competitors To Make investments Is Robust

    By the point Demo Day arrives, the businesses with essentially the most traction have already crammed their rounds. So if you’d like an actual shot at investing, you could attain out to founders one to a few weeks earlier than. And for those who aren’t a recognizable angel or a VC from a recognized establishment, getting in could be robust.

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

    My favourite pivot is Slack. It began as an inside communication software for a failed massively multiplayer on-line recreation referred to as Glitch. The sport shut down, the crew rebranded the software, 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 largest 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’ve got missed out. The subsequent Airbnb not often seems to be 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 assist nice founders. Thanks for having us, Garry.

    What Angel Traders Ought to Convey To The Desk

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

    • Distribution. Entry to an actual viewers of potential clients, the one hardest factor for an early-stage firm to construct from scratch.
    • Introductions to clients who match the founder’s goal profile.
    • Assist discovering the correct early staff to spherical out a crew.
    • Introductions to different traders for the following spherical.
    • Working experience throughout product, advertising and marketing, and growth, ideally earned the exhausting approach by truly working 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 working a worthwhile enterprise, and I will help 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 sector to what’s most related. Out of your shortlist, you may put money into simply 10%, so you could discuss to as many founders as potential. Construct your funnel.

    I had 5 names on my record out of 196, centered on private finance, fintech, and shopper firms the place I knew I may 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 have been already full, which is the norm for the most popular firms by Demo Day. No exhausting emotions. I consider in serendipity. If it is meant to be, it is meant to be.

    A fast notice on etiquette, as a result of I’ve had differing opinions on 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 price. As an alternative, I need to construct rapport first, take heed to their story, after which observe up with the tougher diligence questions afterward, when you’ve gotten 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 glad hour in the event that they have 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 hear, provide encouragement, and be useful. It takes actual braveness to stroll as much as a stranger and ask for one thing. As a result of for those who by no means ask, you by no means get. It jogged my memory of my courting years. In case your success price is just 5%, you’d higher ask 20 instances to get one sure.

    YC Demo Day pitch

    A Very Small World With Lots To Eat And Drink

    Demo Day additionally had countless free meals and drinks, which most conferences don’t. I appreciated the unfold inside, plus all of the meals vehicles and distributors exterior. Exhausting to be in a nasty 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 have been doing their very own diligence, making an attempt to learn the developments. Possibly they have 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 take a position, you must be genuinely good. Work on that emotional intelligence. The very last thing you need is to get blackballed since you have 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 need to enable you to.

    Open To Make investments

    My remaining takeaway is that being a enterprise investor is tough. We already know the way exhausting it’s to be a founder who will get an organization off the bottom. A whole lot of of us prefer to poke enjoyable at enterprise capitalists, considering they’ve soft lives, do not must work too exhausting, 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 firms 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 lots.

    And even if you get the assembly and resolve to take a position, 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 firms, 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 firms. I’ve put aside $150,000 a yr for angel investing. Let’s examine what occurs.

    And for those who’re a founder, YC or in any other case, elevating capital and also you suppose I will help, please attain out. My electronic mail is on the backside of my About page, or you may depart a remark under.

    Construct on!

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

    Wish to construct monetary freedom sooner, slightly than later? Be part of 60,000+ readers and get my free weekly newsletter 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. Every thing I write comes from actual expertise, not idea.





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