What they'll do is scarier.

My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.

They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.

Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.

This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.

Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it

The unsettling reality behind door #1

You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.

They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.

Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.

My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.

Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.

Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.

Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.

I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.

The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.

When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.

Who's in danger?

In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.

Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).

This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.

If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).

The kiss of death (and how to avoid it)

If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?

I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.

Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.

How can you avoid this bottomless pit? Tips:

• Understand your burn rate

• Keep an eye on your growth or profitability.

• Analyze each and every marketing channel and initiative.

• Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.

Not as much as your grandfather

My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.

More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.

Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

It's ok and even desired to be unprofitable if you're gaining revenue at a reasonable cost and have 100%+ net dollar retention, meaning you never lose customers and expand them. To estimate the acceptable cost of new SaaS revenue, we compare new revenue to operating loss and payback period. If you pay back the customer acquisition cost in 1.5 years and never lose them (100%+ NDR), you're doing well.

To evaluate payback period, we compared new revenue to net operating loss for the last 73 SaaS companies to IPO since October 2017. (55 out of 73). Here's the data. 1/(new revenue/operating loss) equals payback period. New revenue/operating loss equals cost of new revenue.

Payback averages a year. 55 SaaS companies that weren't profitable at IPO got a 1-year payback. Outstanding. If you pay for a customer in a year and never lose them (100%+ NDR), you're establishing a valuable business. The average was 1.3 years, which is within the 1.5-year range.

New revenue costs $0.96 on average. These SaaS companies lost $0.96 every $1 of new revenue last year. Again, impressive. Average new revenue per operating loss was $1.59.

Loss-in-operations definition. Operating loss revenue COGS S&M R&D G&A (technical point: be sure to use the absolute value of operating loss). It's wrong to only consider S&M costs and ignore other business costs. Operating loss and new revenue are measured over one year to eliminate seasonality.

Operating losses are desirable if you never lose a customer and have a quick payback period, especially when SaaS enterprises are valued on ARR. The payback period should be under 1.5 years, the cost of new income < $1, and net dollar retention 100%.

This is for young entrepreneurs, especially in tech.

People give useless success advice on TikTok and Reddit. Early risers, bookworms, etc. Entrepreneurship courses. Work hard and hustle.

False. These aren't successful traits.

I mean, organization is good. As someone who founded several businesses and now works at a VC firm, I find these tips to be clichés.

Based on founding four successful businesses and working with other successful firms, here's my best actionable advice:

1. Choose a sector or a niche and become an expert in it.

This is more generic than my next tip, but it's a must-do that's often overlooked. Become an expert in the industry or niche you want to enter. Discover everything.

Buy (future) competitors' products. Understand consumers' pain points. Market-test. Target keyword combos. Learn technical details.

The most successful businesses I've worked with were all formed by 9-5 employees. They knew the industry's pain points. They started a business targeting these pain points.

2. Choose a niche or industry crossroads to target.

How do you choose an industry or niche? What if your industry is too competitive?

List your skills and hobbies. Randomness is fine. Find an intersection between two interests or skills.

Say you build websites well. You like cars.

Web design is a *very* competitive industry. Cars and web design?

Instead of web design, target car dealers and mechanics. Build a few fake demo auto mechanic websites, then cold call shops with poor websites. Verticalize.

I've noticed a pattern:

• Person works in a particular industry for a corporation.

• Person gains expertise in the relevant industry.

• Person quits their job and launches a small business to address a problem that their former employer was unwilling to address.

I originally posted this on Reddit and it seemed to have taken off so I decided to share it with you all.

Focus on the product. When someone buys from you, you convince them the product's value exceeds the price. It's not fair and favors the buyer.

Creating a superior product or service will win. Narrowing this helps you outcompete others.

You may be their only (lucky) option.

It’s simply not conceivable, or at least not credible.

One of the most touted selling points of Crypto has always been this grandiose idea of decentralization. Bitcoin first arose in 2009 after the housing crisis and subsequent crash that came with it. It aimed to solve this supposed issue of centralization. Nobody “owns” Bitcoin in theory, so the idea then goes that it won’t be subject to the same downfalls that led to the 2008 crash or similarly speculative events that led to the 2008 disaster. The issue is the banks, not the human nature associated with the greedy individuals running them.

Subsequent blockchains have attempted to fix many of the issues of Bitcoin by increasing capacity, decreasing the costs and processing times associated with Bitcoin, and expanding what can be done with their blockchains. Since nobody owns Bitcoin, it hasn’t really been able to be expanded on. You have people like Vitalk Buterin, however, that actively work on Ethereum though.

The leap from Bitcoin to Ethereum was a massive leap toward centralization, and the trend has only gotten worse. In fact, crypto has since become almost exclusively centralized in recent years.

Decentralization is only good in theory

It’s a good idea. In fact, it’s a wonderful idea. However, like other utopian societies, individuals misjudge human nature and greed. In a perfect world, decentralization would certainly be a wonderful idea because sure, people may function as their own banks, move payments immediately, remain anonymous, and so on. However, underneath this are a couple issues:

• You can already send money instantaneously today.

• They are not decentralized.

• Decentralization is a bad idea.

• Being your own bank is a stupid move.

Let’s break these down. Some are quite simple, but lets have a look.

Sending money right away

One thing with crypto is the idea that you can send payments instantly. This has pretty much been entirely solved in current times. You can transmit significant sums of money instantly for a nominal cost and it’s instantaneously cleared. Venmo was launched in 2009 and has since increased to prominence, and currently is on most people's phones. I can directly send ANY amount of money quickly from my bank to another person's Venmo account.

Comparing that with ETH and Bitcoin, Venmo wins all around. I can send money to someone for free instantly in dollars and the only fee paid is optional depending on when you want it.

Both Bitcoin and Ethereum are subject to demand. If the blockchains have a lot of people trying to process transactions fee’s go up, and the time that it takes to receive your crypto takes longer. When Ethereum gets bad, people have reported spending several thousand of dollars on just 1 transaction.

These transactions take place via “miners” bundling and confirming transactions, then recording them on the blockchain to confirm that the transaction did indeed happen. They charge fees to do this and are also paid in Bitcoin/ETH. When a transaction is confirmed, it's then sent to the other users wallet. This within itself is subject to lots of controversy because each transaction needs to be confirmed 6 times, this takes massive amounts of power, and most of the power is wasted because this is an adversarial system in which the person that mines the transaction gets paid, and everyone else is out of luck. Also, these could theoretically be subject to a “51% attack” in which anyone with over 51% of the mining hash rate could effectively control all of the transactions, and reverse transactions while keeping the BTC resulting in “double spending”.

There are tons of other issues with this, but essentially it means: They rely on these third parties to confirm the transactions. Without people confirming these transactions, Bitcoin stalls completely, and if anyone becomes too dominant they can effectively control bitcoin.

Not to mention, these transactions are in Bitcoin and ETH, not dollars. So, you need to convert them to dollars still, and that's several more transactions, and likely to take several days anyway as the centralized exchange needs to send you the money by traditional methods.

They are not distributed

That takes me to the following point. This isn’t decentralized, at all. Bitcoin is the closest it gets because Satoshi basically closed it to new upgrades, although its still subject to:

• Whales

• Miners

It’s vital to realize that these are often the same folks. While whales aren’t centralized entities typically, they can considerably effect the price and outcome of Bitcoin. If the largest wallets holding as much as 1 million BTC were to sell, it’d effectively collapse the price perhaps beyond repair. However, Bitcoin can and is pretty much controlled by the miners. Further, Bitcoin is more like an oligarchy than decentralized. It’s been effectively used to make the rich richer, and both the mining and price is impacted by the rich. The overwhelming minority of those actually using it are retail investors. The retail investors are basically never the ones generating money from it either.

As far as ETH and other cryptos go, there is realistically 0 case for them being decentralized. Vitalik could not only kill it but even walking away from it would likely lead to a significant decline. It has tons of issues right now that Vitalik has promised to fix with the eventual Ethereum 2.0., and stepping away from it wouldn’t help.

Most tokens as well are generally tied to some promise of future developments and creators. The same is true for most NFT projects. The reason 99% of crypto and NFT projects fail is because they failed to deliver on various promises or bad dev teams, or poor innovation, or the founders just straight up stole from everyone. I could go more in-depth than this but go find any project and if there is a dev team, company, or person tied to it then it's likely, not decentralized. The success of that project is directly tied to the dev team, and if they wanted to, most hold large wallets and could sell it all off effectively killing the project. Not to mention, any crypto project that doesn’t have a locked contract can 100% be completely rugged and they can run off with all of the money.

Decentralization is undesirable

Even if they were decentralized then it would not be a good thing. The graphic above indicates this is effectively a rich person’s unregulated playground… so it’s exactly like… the very issue it tried to solve?

Not to mention, it’s supposedly meant to prevent things like 2008, but is regularly subjected to 50–90% drawdowns in value? Back when Bitcoin was only known in niche parts of the dark web and illegal markets, it would regularly drop as much as 90% and has a long history of massive drawdowns.

The majority of crypto is blatant scams, and ALL of crypto is a “zero” or “negative” sum game in that it relies on the next person buying for people to make money. This is not a good thing. This has yet to solve any issues around what caused the 2008 crisis. Rather, it seemingly amplified all of the bad parts of it actually. Crypto is the ultimate speculative asset and realistically has no valuation metric. People invest in Apple because it has revenue and cash on hand. People invest in crypto purely for speculation. The lack of regulation or accountability means this is amplified to the most extreme degree where anything goes: Fraud, deception, pump and dumps, scams, etc. This results in a pure speculative madhouse where, unsurprisingly, only the rich win. Not only that but the deck is massively stacked in against the everyday investor because you can’t do a pump and dump without money.

At the heart of all of this is still the same issues: greed and human nature. However, in setting out to solve the issues that allowed 2008 to happen, they made something that literally took all of the bad parts of 2008 and then amplified it. 2008, similarly, was due to greed and human nature but was allowed to happen due to lack of oversite, rich people's excessive leverage over the poor, and excessive speculation. Crypto trades SOLELY on human emotion, has 0 oversite, is pure speculation, and the power dynamic is just as bad or worse.

Why should each individual be their own bank?

This is the last one, and it's short and basic. Why do we want people functioning as their own bank? Everything we do relies on another person. Without the internet, and internet providers there is no crypto. We don’t have people functioning as their own home and car manufacturers or internet service providers. Sure, you might specialize in some of these things, but masquerading as your own bank is a horrible idea.

I am not in the banking industry so I don’t know all the issues with banking. Most people aren’t in banking or crypto, so they don’t know the ENDLESS scams associated with it, and they are bound to lose their money eventually.

If you appreciate this article and want to read more from me and authors like me, without any limits, consider buying me a coffee: buymeacoffee.com/calebnaysmith

If you think NFTs are awful, check out the art market.

The fervor around NFTs has subsided in recent months due to the crypto market crash and the media's short attention span. They were all anyone could talk about earlier this spring. Last semester, when passions were high and field luminaries were discussing "slurp juices," I asked my students and students from over 20 other universities what they thought of NFTs.

According to many, NFTs were either tasteless pyramid schemes or a new way for artists to make money. NFTs contributed to the climate crisis and harmed the environment, but so did air travel, fast fashion, and smartphones. Some students complained that NFTs were cheap, tasteless, algorithmically generated schlock, but others asked how this was different from other art.

I'm not sure what I expected, but the intensity of students' reactions surprised me. They had strong, emotional opinions about a technology I'd always considered administrative. NFTs address ownership and accounting, like most crypto/blockchain projects.

Art markets can be irrational, arbitrary, and subject to the same scams and schemes as any market. And maybe a few shenanigans that are unique to the art world.

The Fairness Question

Fairness, a deflating moral currency, was the general sentiment (the less of it in circulation, the more ardently we clamor for it.) These students, almost all of whom are artists, complained to the mismatch between the quality of the work in some notable NFT collections and the excessive amounts these items were fetching on the market. They can sketch a Bored Ape or Lazy Lion in their sleep. Why should they buy ramen with school loans while certain swindlers get rich?

I understand students. Art markets are unjust. They can be irrational, arbitrary, and governed by chance and circumstance, like any market. And art-world shenanigans.

Almost every mainstream critique leveled against NFTs applies just as easily to art markets

Over 50% of artworks in circulation are fake, say experts. Sincere art collectors and institutions are upset by the prevalence of fake goods on the market. Not everyone. Wealthy people and companies use art as investments. They can use cultural institutions like museums and galleries to increase the value of inherited art collections. People sometimes buy artworks and use family ties or connections to museums or other cultural taste-makers to hype the work in their collection, driving up the price and allowing them to sell for a profit. Money launderers can disguise capital flows by using market whims, hype, and fluctuating asset prices.

Almost every mainstream critique leveled against NFTs applies just as easily to art markets.

Art has always been this way. Edward Kienholz's 1989 print series satirized art markets. He stamped 395 identical pieces of paper from $1 to $395. Each piece was initially priced as indicated. Kienholz was joking about a strange feature of art markets: once the last print in a series sells for $395, all previous works are worth at least that much. The entire series is valued at its highest auction price. I don't know what a Kienholz print sells for today (inquire with the gallery), but it's more than $395.

I love Lee Lozano's 1969 "Real Money Piece." Lozano put cash in various denominations in a jar in her apartment and gave it to visitors. She wrote, "Offer guests coffee, diet pepsi, bourbon, half-and-half, ice water, grass, and money." "Offer real money as candy."

Lee Lozano kept track of who she gave money to, how much they took, if any, and how they reacted to the offer of free money without explanation. Diverse reactions. Some found it funny, others found it strange, and others didn't care. Lozano rarely says:

Apr 17 Keith Sonnier refused, later screws lid very tightly back on. Apr 27 Kaltenbach takes all the money out of the jar when I offer it, examines all the money & puts it all back in jar. Says he doesn’t need money now. Apr 28 David Parson refused, laughing. May 1 Warren C. Ingersoll refused. He got very upset about my “attitude towards money.” May 4 Keith Sonnier refused, but said he would take money if he needed it which he might in the near future. May 7 Dick Anderson barely glances at the money when I stick it under his nose and says “Oh no thanks, I intend to earn it on my own.” May 8 Billy Bryant Copley didn’t take any but then it was sort of spoiled because I had told him about this piece on the phone & he had time to think about it he said.

Smart Contracts (smart as in fair, not smart as in Blockchain)

Cornell University's Cheryl Finley has done a lot of research on secondary art markets. I first learned about her research when I met her at the University of Florida's Harn Museum, where she spoke about smart contracts (smart as in fair, not smart as in Blockchain) and new protocols that could help artists who are often left out of the economic benefits of their own work, including women and women of color.

Her talk included findings from her ArtNet op-ed with Lauren van Haaften-Schick, Christian Reeder, and Amy Whitaker.

NFTs allow us to think about and hack on formal contractual relationships outside a system of laws that is currently not set up to service our community.

The ArtNet article The Recent Sale of Amy Sherald's ‘Welfare Queen' Symbolizes the Urgent Need for Resale Royalties and Economic Equity for Artists discussed Sherald's 2012 portrait of a regal woman in a purple dress wearing a sparkling crown and elegant set of pearls against a vibrant red background.

Amy Sherald sold "Welfare Queen" to Princeton professor Imani Perry. Sherald agreed to a payment plan to accommodate Perry's budget.

Amy Sherald rose to fame for her 2016 portrait of Michelle Obama and her full-length portrait of Breonna Taylor, one of the most famous works of the past decade.

As is common, Sherald's rising star drove up the price of her earlier works. Perry's "Welfare Queen" sold for $3.9 million in 2021.

Imani Perry's early investment paid off big-time. Amy Sherald, whose work directly increased the painting's value and who was on an artist's shoestring budget when she agreed to sell "Welfare Queen" in 2012, did not see any of the 2021 auction money. Perry and the auction house got that money.

Sherald sold her Breonna Taylor portrait to the Smithsonian and Louisville's Speed Art Museum to fund a $1 million scholarship. This is a great example of what an artist can do for the community if they can amass wealth through their work.

NFTs haven't solved all of the art market's problems — fakes, money laundering, market manipulation — but they didn't create them. Blockchain and NFTs are credited with making these issues more transparent. More ideas emerge daily about what a smart contract should do for artists.

NFTs are a copyright solution. They allow us to hack formal contractual relationships outside a law system that doesn't serve our community.

Amy Sherald shows the good smart contracts can do (as in, well-considered, self-determined contracts, not necessarily blockchain contracts.) Giving back to our community, deciding where and how our work can be sold or displayed, and ensuring artists share in the equity of our work and the economy our labor creates.