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 most important and arguably the most effective startup accelerator on the planet. And it occurs to be primarily based in my yard in San Francisco.
I have been a startup investor since 2002, a enterprise capital LP since 2006, and a non-public firm operator since 2009 with Monetary Samurai. I’ve cherished startups and the entrepreneurial life ever since spending my center faculty years in Kuala Lumpur, Malaysia.
The households with giant houses 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 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 faculty. In 1999, a household buddy provided me a job in Shenzhen, China to run his eyeglass components manufacturing facility 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 robust to show down.
However ever since 1999, I’ve carried loads of what-ifs in regards to 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 means, reopening a door I closed 26 years in the past.
Why Y Combinator Is Price Exhibiting 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 the planet. 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 making an attempt to pry open.
Does this system really work? The numbers say sure. About 4.5% of YC firms go on to change into billion-dollar unicorns, versus 2.5% for different venture-backed seed-stage startups. Roughly 45% increase a Sequence A, in comparison with 33% for everybody else. So far, 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 gasoline on them. Additionally it is a wonderful enterprise mannequin.
So when higher odds at a unicorn are on the desk, you present up.
Y Combinator And Serendipity
I firmly imagine most outsized success 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 referred to as FutureAdvisor, a YC ‘10 firm. His co-founder, Jon, occurred to be a dad at my youngsters’ faculty in the identical grade. Jon went on to change into a full associate at Y Combinator in 2023.
This is Jon sharing recommendation on YC’s Startup College.
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 Sequence A, and I believed to myself, why did not I assist and make investments? It is just because I had no thought what he did. Please ask individuals 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 bought 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 kinds 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 workers for having me.
Incredible Power And Creativity
The primary takeaway is that YC Demo Day is a blast of adrenaline that makes you need to run by means of partitions. You need to construct merchandise that resolve onerous issues. You then begin questioning whether or not your personal work has sufficient goal and that means.
One founder I met was Marshall Gould, a researcher in genomic drugs 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 means of these days, I’d have paid virtually something to really feel higher, or not less than not really feel alone.
Over 1 billion individuals dwell with situations 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 onerous 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 virtually no one is constructing particularly for it.
I’ve invited Marshall onto the Monetary Samurai podcast (linked to an Apple interview w/ the CEO of Human Curiosity, who can also be a YC alum and identical faculty dad) so extra of you’ll be able to hear his story straight. It feels nice to assist founders do nice issues for humanity.

The Competitors To Make investments Is Powerful
By the point Demo Day arrives, the businesses with essentially the most traction have already crammed their funding rounds. So if you would like an actual shot at investing, you could attain out to founders one to 3 weeks earlier than. And in the event you aren’t a recognizable angel or a VC from a recognized establishment, getting in will be robust.
That stated, 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 is never the ultimate product. Firms pivot and iterate continually.
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 group rebranded the software, and Slack launched in 2013. In 2021, it bought to Salesforce for $27.7 billion. Not dangerous for a aspect function of a online game no one performed.
The largest funding winners are virtually 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 following Airbnb hardly ever seems like the subsequent Airbnb on day one.

What Angel Buyers Ought to Convey To The Desk
As an angel, in the event you aren’t writing the largest examine, or aren’t a star, you’d higher add essentially the most worth. The founders price backing are those you’ll be able to genuinely assist. This is what each angel ought to assume onerous about bringing to the desk earlier than exhibiting up:
- Distribution. Entry to an actual viewers of potential prospects, the one hardest factor for an early-stage firm to construct from scratch.
- Introductions to prospects who match the founder’s goal profile.
- Assist discovering the suitable early staff to spherical out a group.
- Introductions to different traders for the subsequent spherical.
- Working experience throughout product, advertising and marketing, and enlargement, ideally earned the onerous means by really 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 client founders need. Add 20 years of enterprise LP relationships and 17 years working a worthwhile enterprise, and I will help with intros, the subsequent spherical, and working insights.
Be Proactive And Take Initiative
From an investor’s standpoint, there are about 200 founders in every batch to trace. So it’s a must to do your homework beforehand and slim the sector to what’s most related. Out of your shortlist, you may spend money on simply 10%, so you could discuss to as many founders as attainable. Construct your funnel.
I had 5 names on my checklist out of 196, centered on insurance coverage, investing, actual property, and client the place I knew I may add worth. I had two nice conversations and reached out to the opposite three on-line. They did not reply, doubtless as a result of their rounds have been already full, which is the norm. No onerous emotions. I imagine 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 method 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 need to construct rapport first, take heed to their story, after which observe up with the tougher diligence questions afterward, when you might 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 method me and my companions throughout breaks, lunch, and completely satisfied 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 in the event you by no means ask, you by no means get. It jogged my memory of my relationship years. In case your success fee is barely 5%, you’d higher ask 20 occasions to get one sure.

A Very Small World With Loads 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 vans and distributors outdoors. Onerous 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 have been doing their very own diligence, making an attempt to learn the developments. Perhaps 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. If you’d like alternatives to speculate, it’s a must to 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 individuals need to show you how to.
Open To Make investments
My remaining takeaway is that being an angel investor is tough. We already know the way onerous it’s to be a founder who will get an organization off the bottom. Lots of of us prefer to poke enjoyable at enterprise capitalists, considering they’ve soft lives 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 12 months. No single particular person can correctly analyze all of them, so it’s a must to area of interest down and settle for that you’re going to miss a lot.
And even while 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 40 to 60 firms, assist the place you’ll be able to, and wait 8 to 11 years to see outcomes.
I hope to return to many extra Demo Days and spend money on extra firms. I’ve put aside $200,000 a 12 months for angel investing. Let’s see what occurs as I share the journey.
And in the event you’re a founder, YC or in any other case, elevating capital and also you assume I will help, please attain out. My e-mail is on the backside of my About web page, or you’ll be able to go away a remark under.
Construct on!
Are any readers traders in YC firms 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?
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