Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

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!

Startup entrepreneurs assume what risks when pitching?

Last week I signed four NDAs.

Four!

NDA stands for non-disclosure agreement. A legal document given to someone receiving confidential information. By signing, the person pledges not to share the information for a certain time. If they do, they may be in breach of contract and face legal action.

Companies use NDAs to protect trade secrets and confidential internal information from employees and contractors. Appropriate. If you manage a huge, successful firm, you don't want your employees selling their information to your competitors. To be true, business NDAs don't always prevent corporate espionage, but they usually make employees and contractors think twice before sharing.

I understand employee and contractor NDAs, but I wasn't asked to sign one. I counsel entrepreneurs, thus the NDAs I signed last week were from startups that wanted my feedback on their concepts.

I’m not a startup investor. I give startup guidance online. Despite that, four entrepreneurs thought their company ideas were so important they wanted me to sign a generically written legal form they probably acquired from a shady, spam-filled legal templates website before we could chat.

False. One company tried to get me to sign their NDA a few days after our conversation. I gently rejected, but their tenacity encouraged me. I considered sending retroactive NDAs to everyone I've ever talked to about one of my startups in case they establish a successful company based on something I said.

Two of the other three NDAs were from nearly identical companies. Good thing I didn't sign an NDA for the first one, else they may have sued me for talking to the second one as though I control the firms people pitch me.

I wasn't talking to the fourth NDA company. Instead, I received an unsolicited email from someone who wanted comments on their fundraising pitch deck but required me to sign an NDA before sending it.

That's right, before I could read a random Internet stranger's unsolicited pitch deck, I had to sign his NDA, potentially limiting my ability to discuss what was in it.

You should understand. Advisors, mentors, investors, etc. talk to hundreds of businesses each year. They cannot manage all the companies they deal with, thus they cannot risk legal trouble by talking to someone. Well, if I signed NDAs for all the startups I spoke with, half of the 300+ articles I've written on Medium over the past several years could get me sued into the next century because I've undoubtedly addressed topics in my articles that I discussed with them.

The four NDAs I received last week are part of a recent trend of entrepreneurs sending out NDAs before meetings, despite the practical and legal issues. They act like asking someone to sign away their right to talk about all they see and hear in a day is as straightforward as asking for a glass of water.

Given this inflow of NDAs, I wanted to briefly remind entrepreneurs reading this blog about the merits and cons of requesting investors (or others in the startup ecosystem) to sign your NDA.

Benefits of having investors sign your NDA include:

None. Zero. Nothing.

Disadvantages of requesting investor NDAs:

• You'll come off as an amateur who has no idea what it takes to launch a successful firm.

• Investors won't trust you with their money since you appear to be a complete amateur.

• Printing NDAs will be a waste of paper because no genuine entrepreneur will ever sign one.

I apologize for missing any cons. Please leave your remarks.

Market fraud

Due to its decentralized and fragmented character, the crypto market has integrity difficulties.

Cryptocurrencies are an immature sector, therefore market manipulation becomes a bigger issue. Many research have attempted to uncover these abuses. CryptoCompare's newest one highlights some of the industry's most typical scams.

Why are these concerns so common in the crypto market? First, even the largest centralized exchanges remain unregulated due to industry immaturity. A low-liquidity market segment makes an attack more harmful. Finally, market surveillance solutions not implemented reduce transparency.

In CryptoCompare's latest exchange benchmark, 62.4% of assessed exchanges had a market surveillance system, although only 18.1% utilised an external solution. To address market integrity, this measure must improve dramatically. Before discussing the report's malpractices, note that this is not a full list of attacks and hacks.

Clean Trading

An investor buys and sells concurrently to increase the asset's price. Centralized and decentralized exchanges show this misconduct. 23 exchanges have a volume-volatility correlation < 0.1 during the previous 100 days, according to CryptoCompares. In August 2022, Exchange A reported $2.5 trillion in artificial and/or erroneous volume, up from $33.8 billion the month before.

Spoofing

Criminals create and cancel fake orders before they can be filled. Since manipulators can hide in larger trading volumes, larger exchanges have more spoofing. A trader placed a 20.8 BTC ask order at $19,036 when BTC was trading at $19,043. BTC declined 0.13% to $19,018 in a minute. At 18:48, the trader canceled the ask order without filling it.

Front-Running

Most cryptocurrency front-running involves inside trading. Traditional stock markets forbid this. Since most digital asset information is public, this is harder. Retailers could utilize bots to front-run.

CryptoCompare found digital wallets of people who traded like insiders on exchange listings. The figure below shows excess cumulative anomalous returns (CAR) before a coin listing on an exchange.

Finally, LAYERING is a sequence of spoofs in which successive orders are put along a ladder of greater (layering offers) or lower (layering bids) values. The paper concludes with recommendations to mitigate market manipulation. Exchange data transparency, market surveillance, and regulatory oversight could reduce manipulative tactics.

A few days ago, I was discussing dall-e with two art and tech pals. One artist acquaintance said she knew a frightened illustrator. Would the ability to create anything with a click derail her career? The artist feared this. My curator friend smiled and said this has always been a dread among artists. When the camera was invented, didn't painters say this? Even in the Instagram era, painting exists.

When art and technology collide, there's room for innovation, experimentation, and fear — especially if the technology replicates or replaces art making. What is art's future with dall-e? How does technology affect music, beyond visual art? Recently, I saw "ABBA Voyage," a holographic ABBA concert in London.

"Abba voyage?" my phone asked in early March. A Gen X friend I met through a fashion blogging ring texted me.

"What's abba Voyage?" I asked while opening my front door with keys and coffee.

We're going! Marti, visiting London, took me to a show.

"Absolutely no ABBA songs here." I responded.

My parents didn't play ABBA much, so I don't know much about them. Dad liked Jimi Hendrix, Cream, Deep Purple, and New Orleans jazz. Marti told me ABBA Voyage was a holographic ABBA show with a live band.

The show was fun, extraordinary fun. Nearly everyone on the dance floor wore wigs, ankle-breaking platforms, sequins, and bellbottoms. I saw some millennials and Zoomers among the boomers.

I was intoxicated by the experience.

Automatons date back to the 18th-century mechanical turk. The mechanical turk was a chess automaton operated by a person. The mechanical turk seemed to perform like a human without human intervention, but it required a human in the loop to work properly.

Humans have used non-humans in entertainment for centuries, such as puppets, shadow play, and smoke and mirrors. A show can have animatronic, technological, and non-technological elements, and a live show can blur real and illusion. From medieval puppet shows to mechanical turks to AI filters, bots, and holograms, entertainment has evolved over time.

I'm not a hologram skeptic, but I'm skeptical of technology, especially since I work with it. I love live performances, I love hearing singers breathe, forget lines, and make jokes. Live shows are my favorite because I love watching performers make mistakes or interact with the audience. ABBA Voyage was different.

Marti and I traveled to Manchester after ABBA Voyage to see Liam Gallagher. Similar but different vibe. Similar in that thousands dressed up for the show. ABBA's energy was dizzying. 90s chic replaced sequins in the crowd. Doc Martens, nylon jackets, bucket hats, shaggy hair. The Charlatans and Liam Gallagher opened and closed, respectively. Fireworks. Incredible. People went crazy. Yelling exhausted my voice.

This week in music featured AI-enabled holograms and a decades-old rocker. Both are warm and gooey in our memories.

After seeing both, I'm wondering if we need AI hologram shows. Why? Is it good?

Like everything tech-related, my answer is "maybe." Because context and performance matter. Liam Gallagher and ABBA both had great, different shows.

For a hologram to work, it must be impossible and big. It must be big, showy, and improbable to justify a hologram. It must feel...expensive, like a stadium pop show. According to a quick search, ABBA broke up on bad terms. Reuniting is unlikely. This is also why Prince or Tupac hologram shows work. We can only engage with their legacy through covers or...holograms.

I drove around listening to the radio a few weeks ago. "Dreaming of You" by Selena played. Selena's music defined my childhood. I sang along and turned up the volume (or as loud as my husband would allow me while driving on the highway).

I discovered Selena's music six months after her death, so I never saw her perform live. My babysitter Melissa played me her album after I moved to Houston. Melissa took me to see the Selena movie five times when it came out. I quickly wore out my VHS copy. I constantly sang "Bibi Bibi Bom Bom" and "Como la Flor." I love Selena. A Selena hologram? Yes, probably.

Instagram advertised a cellist's Arthur Russell tribute show. Russell is another deceased artist I love. I almost walked down the aisle to "This is How We Walk on the Moon," but our cellist couldn't find it. Instead, I walked to Magnetic Fields' "The Book of Love." I "discovered" Russell after a friend introduced me to his music a few years ago.

I use these as analogies for the Liam Gallagher and ABBA concerts.

You have no idea how much I'd pay to see a hologram of Selena's 1995 Houston Livestock Show and Rodeo concert. Arthur Russell's hologram is unnecessary. Russell's work was intimate and performance-based. We can't separate his life from his legacy; popular audiences overlooked his genius. He died of AIDS broke. Like Selena, he died prematurely. Given his music and history, another performer would be a better choice than a hologram. He's no Selena. Selena could have rivaled Beyonce.

Pop shows' size works for holograms. Along with ABBA holograms, there was an anime movie and a light show that would put Tron to shame. ABBA created a tourable stadium show. The event was lavish, expensive, and well-planned. Pop, unlike rock, isn't gritty. Liam Gallagher hologram? No longer impossible, it wouldn't work. He's touring. I'm not sure if a rockstar alone should be rendered as a hologram; it was the show that made ABBA a hologram.

Holograms, like AI, are part of the future of entertainment, but not all of it. Because only modern interpretations of Arthur Russell's work reveal his legacy. That's his legacy.

Large-scale arena performers may use holograms in the future, but the experience must be impossible. A teacher once said that the only way to convey emotion in opera is through song, and I feel the same way about holograms, AR, VR, and mixed reality. A story's impossibility must make sense, like in opera. Impossibility and bombastic performance must be present for an immersive element to "work." ABBA was an impossible and improbable experience, which made it magical. It helped the holographic show work.

Marti told me about ABBA Voyage. She said it was a great concert. Marti has worked in music since the 1990s. She's a music expert; she's seen many shows.

Ai isn't a god or sentient, and the ABBA holograms aren't real. The renderings were glassy-eyed, flat, and robotic, like the Polar Express or the Jaws shark. Even today, the uncanny valley is insurmountable. We know it's not real because it's not about reality. It was about a suspended moment and performance feelings.

I knew this was impossible, an 'unreal' experience, but the emotions I felt were real, like watching a movie or tv show. Perhaps this is one of the better uses of AI, like CGI and special effects, like the beauty of entertainment- we were enraptured and entertained for hours. I've been playing ABBA since then.