A part of the explanation I have been writing about distribution and the significance of ultimately betting on yourself 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 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 beloved 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 appeared 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 buddy supplied me a job in Shenzhen, China to run his eyeglass elements 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 a substitute, 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 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 begin my very own factor with the launch of Monetary Samurai. YC Demo Day was, in a method, reopening a door I closed 26 years in the past.
Why Y Combinator Is Value Displaying 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 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 attempting 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 Sequence A, in comparison with 33% for everybody else. Thus 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 superb 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 due to luck. And my path to attending YC Demo Day is a good 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 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 concept what he did. Please ask people 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 received 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 varieties 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. Because of Domingo, Garry, and the YC employees for having me.
Unbelievable Power And Creativity
The principle takeaway is that YC Demo Day is a blast of adrenaline that makes you need to run via partitions. You need to construct merchandise that remedy arduous issues. Then you definately begin questioning whether or not your personal work has sufficient objective and which 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 via these days, I might have paid nearly something to really feel higher, or not less than not really feel alone.
Over 1 billion individuals 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 arduous 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 one is constructing particularly for it.
I’ve invited Marshall onto the Financial Samurai podcast so extra of you may hear his story immediately. 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 stuffed their funding rounds. So if you would like an actual shot at investing, that you must attain out to founders one to a few weeks earlier than. And when you aren’t a recognizable angel or a VC from a identified establishment, getting in could be powerful.
That mentioned, there are nonetheless loads of wonderful firms 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 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 workforce rebranded the software, and Slack launched in 2013. In 2021, it offered to Salesforce for $27.7 billion. Not unhealthy for a aspect function of a online game no one performed.
The most important funding winners are nearly all the time 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 does not imply you have missed out. The subsequent Airbnb not often appears like the subsequent Airbnb on day one.

What Angel Traders Ought to Carry To The Desk
As an angel, when you aren’t writing the most important examine, or aren’t a star, you’d higher add essentially the most worth. The founders value backing are those you may genuinely assist. This is what each angel ought to assume arduous about bringing to the desk earlier than displaying 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 suitable early workers to spherical out a workforce.
- Introductions to different buyers for the subsequent spherical.
- Working experience throughout product, advertising, and enlargement, ideally earned the arduous method by truly working a enterprise.
My edge is distribution. Monetary Samurai reaches a whole bunch of hundreds 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 can assist 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 important to do your homework beforehand and slim the sphere to what’s most related. Out of your shortlist, you would possibly put money into simply 10%, so that you must discuss to as many founders as attainable. Construct your funnel.
I had 5 names on my record out of 196, targeted on insurance coverage, investing, actual property, and client the place I knew I might 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 arduous 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 a substitute, I need to construct rapport first, take heed to their story, after which observe up with the more durable 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 choices 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 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 some extent 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 when you by no means ask, you by no means get. It jogged my memory of my courting years. In case your success charge is just 5%, you’d higher ask 20 occasions to get one sure.

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 vans and distributors outdoors. Laborious 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, attempting to learn the tendencies. 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. In order for you alternatives to take a position, it’s important 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 provide help to.
Open To Make investments
My last takeaway is that being an angel investor is hard. We already understand how arduous it’s to be a founder who will get an organization off the bottom. Plenty of of us wish to poke enjoyable at enterprise capitalists, considering they’ve comfortable 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 individual can correctly analyze all of them, so it’s important to area of interest down and settle for that you’re going to miss loads.
And even if you get the assembly and determine 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 40 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 12 months for angel investing. Let’s see what occurs as I share the journey.
And when you’re a founder, YC or in any other case, elevating capital and also you assume I can assist, please attain out. My e-mail is on the backside of my About page, or you may 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?
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