A part of the explanation I have been writing about distribution and the significance of ultimately betting on your self was to gear myself up for Y Combinator Demo Day. For these unfamiliar, YC is the biggest and arguably the very best startup accelerator on this 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 personal firm operator since 2009 with Monetary Samurai. I’ve beloved startups and the entrepreneurial life ever since spending my center college years in Kuala Lumpur, Malaysia.
The households with massive 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 faculty. In 1999, a household pal supplied me a job in Shenzhen, China to run his eyeglass elements manufacturing unit and probably accomplice 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 whole lot 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 start out my very own factor with the launch of Monetary Samurai. YC Demo Day was, in a manner, reopening 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 an enormous deal.
YC is probably the most selective startup accelerator on this planet. The acceptance charge 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 grow to be billion-dollar unicorns, versus 2.5% for different venture-backed seed-stage startups. Roughly 45% elevate a Sequence A, in comparison with 33% for everybody else. Thus far, YC has funded greater than 90 billion-dollar firms.
You additionally may 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. It’s also 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’ college in the identical grade. Jon went on to grow to be a full accomplice at Y Combinator in 2023.
Here is Jon sharing recommendation on YC’s Startup Faculty.
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 folks 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 college. 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 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 college, I lastly needed to attend Demo Day. Because of Domingo, Garry, and the YC employees for having me.
Unbelievable Power And Creativity
The primary takeaway is that YC Demo Day is a blast of adrenaline that makes you need to run by partitions. You need to construct merchandise that remedy laborious issues. Then you definately begin questioning whether or not your personal work has sufficient function and that means.
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 might had an AI well being assistant to assist me get by these days, I’d have paid virtually something to really feel higher, or a minimum of not really feel alone.
Over 1 billion folks stay 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 laborious fact 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 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 similar college dad) so extra of you’ll be able to hear his story immediately. It feels nice to assist founders do nice issues for humanity.
The Competitors To Make investments Is Robust
By the point Demo Day arrives, the businesses with probably the most traction have already stuffed their funding rounds. So in order for you an actual shot at investing, it is advisable to attain out to founders one to 3 weeks earlier than. And in case you aren’t a recognizable angel or a VC from a identified establishment, getting in could be robust.
That mentioned, there are nonetheless loads of superb firms open to new buyers on Demo Day. And as each founder and investor is aware of, the primary product is never the ultimate product. Corporations pivot and iterate consistently.
My favourite pivot is Slack. It began as an inner communication device for a failed massively multiplayer on-line sport referred to as Glitch. The sport shut down, the workforce rebranded the device, and Slack launched in 2013. In 2021, it bought to Salesforce for $27.7 billion. Not unhealthy 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 have missed out. The following Airbnb not often seems like the subsequent Airbnb on day one.

What Angel Buyers Ought to Convey To The Desk
As an angel, in case you aren’t writing the largest test, or aren’t a star, you’d higher add probably the most worth. The founders price backing are those you’ll be able to 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 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 fitting early workers to spherical out a workforce.
Introductions to different buyers for the subsequent spherical.
Working experience throughout product, advertising and marketing, and enlargement, ideally earned the laborious manner by truly operating a enterprise.
My edge is distribution. Monetary Samurai reaches lots of 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 operating 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 you need to 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 speak to as many founders as attainable. Construct your funnel.
I had 5 names on my listing 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, possible as a result of their rounds had been already full, which is the norm. No laborious 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 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 charge. As an alternative, I need to construct rapport first, hearken to their story, after which observe up with the tougher diligence questions afterward, when you’ve 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 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 some extent to hear, 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 in case you by no means ask, you by no means get. It jogged my memory of my relationship years. In case your success charge is just 5%, you’d higher ask 20 instances to get one sure.

A Very Small World With A lot 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 vans and distributors outdoors. 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 had been doing their very own diligence, making an attempt to learn the traits. Perhaps 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. If you would like alternatives to speculate, you need to 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 need to show you how to.
Open To Make investments
My ultimate takeaway is that being an angel investor is difficult. We already know the way laborious it’s to be a founder who will get an organization off the bottom. A variety of people wish 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 prime 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 you need to area of interest down and settle for that you will miss lots.
And even if you get the assembly and resolve 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 put money into 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 case you’re a founder, YC or in any other case, elevating capital and also you suppose I will help, please attain out. My e-mail is on the backside of my About web page, or you’ll be able to depart a remark beneath.
Construct on!
Are any readers buyers 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?
Need to construct monetary freedom sooner, moderately than later? Be 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. Every thing I write comes from actual expertise, not principle.


