I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.

Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.

Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.

As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.

YC startups by status after 12 years:

Half the startups have failed, over one-third have exited, and the rest are still operating.

In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.

Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.

I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.

Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.

YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)

After 10 years of working in scale-ups, I've embraced a few concepts for scaling Tech and Product teams.

First, cross-functionalize teams. Product Managers represent the business, Product Designers the consumer, and Engineers build.

I organize teams of 5-10 individuals, following AWS's two pizza teams guidelines, with a Product Trio guiding each.

If more individuals are needed to reach a goal, I group teams under a Product Trio.

With Engineering being the biggest group, Staff/Principal Engineers often support the Trio on cross-team technical decisions.

Product Managers, Engineering Managers, or Engineers in the team may manage projects (depending on the project or aim), but the trio is collectively responsible for the team's output and outcome.

Once the Product Trio model is created, roles, duties, team ceremonies, and cooperation models must be clarified.

Keep reporting lines by discipline. Line managers are accountable for each individual's advancement, thus it's crucial that they know the work in detail.

Cross-team collaboration becomes more important after 3 teams (15-30 people). Teams can easily diverge in how they write code, run ceremonies, and build products.

Establishing groups of people that are cross-team, but grouped by discipline and skills, sharing and agreeing on working practices becomes critical.

The “Spotify Guild” model has been where I’ve taken a lot of my inspiration from.

Last, establish a taxonomy for communication channels.

In Slack, I create one channel per team and one per guild (and one for me to have discussions with the team leads).

These are just some of the basic principles I follow to organize teams.

A book I particularly like about team types and how they interact with each other is https://teamtopologies.com/.

5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.

I was entering tens of millions of records per hour when I first published Slonik PostgreSQL client for Node.js. The data being entered was usually flat, making it straightforward to use INSERT INTO ... SELECT * FROM unnset() pattern. I advocated the unnest approach for inserting rows in groups (that was part I).

However, today I’ve found a better way: jsonb_to_recordset.

jsonb_to_recordset expands the top-level JSON array of objects to a set of rows having the composite type defined by an AS clause.

jsonb_to_recordset allows us to query and insert records from arbitrary JSON, like unnest. Since we're giving JSON to PostgreSQL instead of unnest, the final format is more expressive and powerful.

SELECT *
FROM json_to_recordset('[{"name":"John","tags":["foo","bar"]},{"name":"Jane","tags":["baz"]}]')
AS t1(name text, tags text[]);
 name |   tags
------+-----------
 John | {foo,bar}
 Jane | {baz}
(2 rows)

Let’s demonstrate how you would use it to insert data.

Inserting data using json_to_recordset

Say you need to insert a list of people with attributes into the database.

const persons = [
  {
    name: 'John',
    tags: ['foo', 'bar']
  },
  {
    name: 'Jane',
    tags: ['baz']
  }
];

You may be tempted to traverse through the array and insert each record separately, e.g.

for (const person of persons) {
  await pool.query(sql`
    INSERT INTO person (name, tags)
    VALUES (
      ${person.name},
      ${sql.array(person.tags, 'text[]')}
    )
  `);
}

It's easier to read and grasp when working with a few records. If you're like me and troubleshoot a 2M+ insert query per day, batching inserts may be beneficial.

What prompted the search for better alternatives.

Inserting using unnest pattern might look like this:

await pool.query(sql`
  INSERT INTO public.person (name, tags)
  SELECT t1.name, t1.tags::text[]
  FROM unnest(
    ${sql.array(['John', 'Jane'], 'text')},
    ${sql.array(['{foo,bar}', '{baz}'], 'text')}
  ) AS t1.(name, tags);
`);

You must convert arrays into PostgreSQL array strings and provide them as text arguments, which is unsightly. Iterating the array to create slices for each column is likewise unattractive.

However, with jsonb_to_recordset, we can:

await pool.query(sql`
  INSERT INTO person (name, tags)
  SELECT *
  FROM jsonb_to_recordset(${sql.jsonb(persons)}) AS t(name text, tags text[])
`);

In contrast to the unnest approach, using jsonb_to_recordset we can easily insert complex nested data structures, and we can pass the original JSON document to the query without needing to manipulate it.

In terms of performance they are also exactly the same. As such, my current recommendation is to prefer jsonb_to_recordset whenever inserting lots of rows or nested data structures.

Monkey jpegs and shitcoins have tarnished Web3's reputation. Let’s move on.

Web3 was called "the internet's future."

Well, 'crypto bros' shouted about it loudly.

As quickly as it arrived to be the next internet, it appears to be dead. It's had scandals, turbulence, and crashes galore:

• Web 3.0's cryptocurrencies have crashed. Bitcoin's all-time high was $66,935. This month, Ethereum fell from $2130 to $1117. Six months ago, the cryptocurrency market peaked at $3 trillion. Worst is likely ahead.

• Gas fees make even the simplest Web3 blockchain transactions unsustainable.

• Terra, Luna, and other dollar pegs collapsed, hurting crypto markets. Celsius, a crypto lender backed by VCs and Canada's second-largest pension fund, and Binance, a crypto marketplace, have withheld money and coins. They're near collapse.

• NFT sales are falling rapidly and losing public interest.

Web3 has few real-world uses, like most crypto/blockchain technologies. Web3's image has been tarnished by monkey profile pictures and shitcoins while failing to become decentralized (the whole concept is controlled by VCs).

The damage seems irreparable, leaving Web3 in the gutter.

Step forward our new saviour — Web5

Fear not though, as hero awaits to drag us out of the Web3 hellscape. Jack Dorsey revealed his plan to save the internet quickly.

Dorsey has long criticized Web3, believing that VC capital and silicon valley insiders have created a centralized platform. In a tweet that upset believers and VCs (he was promptly blocked by Marc Andreessen), Dorsey argued, "You don't own "Web3." VCs and LPs do. Their incentives prevent it. It's a centralized organization with a new name.

Dorsey announced Web5 on June 10 in a very Elon-like manner. Block's TBD unit will work on the project (formerly Square).

Web5's pitch is that users will control their own data and identity. Bitcoin-based. Sound familiar? The presentation pack's official definition emphasizes decentralization. Web5 is a decentralized web platform that enables developers to write decentralized web apps using decentralized identifiers, verifiable credentials, and decentralized web nodes, returning ownership and control over identity and data to individuals.

Web5 would be permission-less, open, and token-less. What that means for Earth is anyone's guess. Identity. Ownership. Blockchains. Bitcoin. Different.

Web4 appears to have been skipped, forever destined to wish it could have shown the world what it could have been. (It was probably crap.) As this iteration combines Web2 and Web3, simple math and common sense add up to 5. Or something.

Dorsey and his team have had this idea simmering for a while. Daniel Buchner, a member of Block's Decentralized Identity team, said, "We're finishing up Web5's technical components."

Web5 could be the project that decentralizes the internet. It must be useful to users and convince everyone to drop the countless Web3 projects, products, services, coins, blockchains, and websites being developed as I write this.

Web5 may be too late for Dorsey and the incoming flood of creators.

Web6 is planned!

The next months and years will be hectic and less stable than the transition from Web 1.0 to Web 2.0. 

• Web1 was around 1991-2004.

• Web2 ran from 2004 to 2021. (though the Web3 term was first used in 2014, it only really gained traction years later.)

• Web3 lasted a year.

• Web4 is dead.

Silicon Valley billionaires are turning it into a startup-style race, each disrupting the next iteration until they crack it. Or destroy it completely.

Web5 won't last either.