Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

I pitched 10 brands per workday for a total of 200.

How did I do?

It was difficult.

I've never pitched so much.

What did this challenge teach me?

• the superiority of quality over quantity

• When you need help, outsource

• Don't disregard burnout in order to complete a challenge because it exists.

First, pitching brands for brand deals requires quality. Find firms that align with your brand to expose to your audience.

If you associate with any company, you'll lose audience loyalty. I didn't lose sight of that, but I couldn't resist finishing the task.

Outsourcing.

Delegating work to teammates is effective.

I wish I'd done it.

Three people can pitch 200 companies a month significantly faster than one.

One person does research, one to two do outreach, and one to two do follow-up and negotiating.

Simple.

In 2022, I'll outsource everything.

Burnout.

I felt this, so I slowed down at the end of the month.

Thanksgiving week in November was slow.

I was buying and decorating for Christmas. First time putting up outdoor holiday lights was fun.

Much was happening.

I'm not perfect.

I'm being honest.

The Outcomes

Less than 50 brands pitched.

Result: A deal with 3 brands.

I hoped for 4 brands with reaching out to 200 companies, so three with under 50 is wonderful.

That’s a 6% conversion rate!

Whoo-hoo!

I needed 2%.

Here's a screenshot from one of the deals I booked.

These companies fit my company well. Each campaign is different, but I've booked $2,450 in brand work with a couple of pending transactions for December and January.

$2,450 in brand work booked!

How did I do? You tell me.

Is this something you’d try yourself?

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 ;)

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.