During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

Full article is available here

If you're not genuine, you'll be revealed.

Sam Bankman-Fried (SBF) was called the Cryptocurrency Warren Buffet.

No wonder.

SBF's trading expertise, Blockchain knowledge, and ability to construct FTX attracted mainstream investors.

He had a fantastic worldview, donating much of his riches to charity.

As the onion layers peel back, it's clear he wasn't the altruistic media figure he portrayed.

SBF's mistakes were disastrous.

• Customer deposits were traded and borrowed by him.

• With ten other employees, he shared a $40 million mansion where they all had polyamorous relationships.

• Tone-deaf and wasteful marketing expenditures, such as the $200 million spent to change the name of the Miami Heat stadium to the FTX Arena

• Democrats received a $40 million campaign gift.

• And now there seems to be no regret.

FTX was a 32-billion-dollar cryptocurrency exchange.

It went bankrupt practically overnight.

SBF, FTX's creator, exploited client funds to leverage trade.

FTX had $1 billion in customer withdrawal reserves against $9 billion in liabilities in sister business Alameda Research.

Bloomberg Billionaire Index says it's the largest and fastest net worth loss in history.

It gets worse.

SBF's net worth is $900 Million, however he must still finalize FTX's bankruptcy.

SBF's arrest in the Bahamas and SEC inquiry followed news that his cryptocurrency exchange had crashed, losing billions in customer deposits.

A journalist contacted him on Twitter D.M., and their exchange is telling.

His ideas are revealed.

Kelsey Piper says they didn't expect him to answer because people under investigation don't comment.

Bankman-Fried wanted to communicate, and the interaction shows he has little remorse.

SBF talks honestly about FTX gaming customers' money and insults his competition.

Reporter Kelsey Piper was outraged by what he said and felt the mistakes SBF says plague him didn't evident in the messages.

Before FTX's crash, SBF was a poster child for Cryptocurrency regulation and avoided criticizing U.S. regulators.

He tells Piper that his lobbying is just excellent PR.

It shows his genuine views and supports cynics' opinions that his attempts to win over U.S. authorities were good for his image rather than Crypto.

SBF’s responses are in Grey, and Pipers are in Blue.

It's unclear if SBF cut corners for his gain. In their Twitter exchange, Piper revisits an interview question about ethics.

SBF says, "All the foolish sh*t I said"

SBF claims FTX has never invested customer monies.

Piper challenged him on Twitter.

While he insisted FTX didn't use customer deposits, he said sibling business Alameda borrowed too much from FTX's balance sheet.

He did, basically.

When consumers tried to withdraw money, FTX was short.

SBF thought Alameda had enough money to cover FTX customers' withdrawals, but life sneaks up on you.

SBF believes most exchanges have done something similar to FTX, but they haven't had a bank run (a bunch of people all wanting to get their deposits out at the same time).

SBF believes he shouldn't have consented to the bankruptcy and kept attempting to raise more money because withdrawals would be open in a month with clients whole.

If additional money came in, he needed $8 billion to bridge the creditors' deficit, and there aren't many corporations with $8 billion to spare.

Once clients feel protected, they will continue to leave their assets on the exchange, according to one idea.

Kevin OLeary, a world-renowned hedge fund manager, says not all investors will walk through the open gate once the company is safe, therefore the $8 Billion wasn't needed immediately.

SBF claims the bankruptcy was his biggest error because he could have accumulated more capital.

Final Reflections

Sam Bankman-Fried, 30, became the world's youngest billionaire in four years.

Never listen to what people say about investing; watch what they do.

SBF is a trader who gets wrecked occasionally.

Ten first-time entrepreneurs ran FTX, screwing each other with no risk management.

It prevents opposing or challenging perspectives and echo chamber highs.

Twitter D.M. conversation with a journalist is the final nail.

He lacks an experienced crew.

This event will surely speed up much-needed regulation.

It's also prompted cryptocurrency exchanges to offer proof of reserves to calm customers.

Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.

Round size

Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.

Valuation

There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.

Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.

I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.

ARR

Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.

Capitalization Rate

2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:

The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR

What next?

No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

Elon's rides start rough, but then...

Elon Musk has never been so hated.

They don’t get Elon.

• He began using PayPal in this manner.

• He began with SpaceX in a similar manner.

• He began with Tesla in this manner.

Disruptive.

Elon had rocky starts. His creativity requires it. Just like writing a first draft.

His fastest way to find the way is to avoid it.

PayPal's pricey launch

PayPal was a 1999 business flop.

They were considered insane.

Elon and his co-founders had big plans for PayPal. They adopted the popular philosophy of the time, exchanging short-term profit for growth, and pulled off a miracle just before the bubble burst.

PayPal was created as a dollar alternative. Original PayPal software allowed PalmPilot money transfers. Unfortunately, there weren't enough PalmPilot users.

Since everyone had email, the company emailed payments. Costs rose faster than sales.

The startup wanted to get a million subscribers by paying $10 to sign up and $10 for each referral. Elon thought the price was fair because PayPal made money by charging transaction fees. They needed to make money quickly.

A Wall Street Journal article valuing PayPal at $500 million attracted investors. The dot-com bubble burst soon after they rushed to get financing.

Musk and his partners sold PayPal to eBay for $1.5 billion in 2002. Musk's most successful company was PayPal.

SpaceX's start-up error

Elon and his friends bought a reconditioned ICBM in Russia in 2002.

He planned to invest much of his wealth in a stunt to promote NASA and space travel.

Many called Elon crazy.

The goal was to buy a cheap Russian rocket to launch mice or plants to Mars and return them. He thought SpaceX would revive global space interest. After a bad meeting in Moscow, Elon decided to build his own rockets to undercut launch contracts.

Then SpaceX was founded.

Elon’s plan was harder than expected.

Explosions followed explosions.

• Millions lost on cargo.

• Millions lost on the rockets.

Investors thought Elon was crazy, but he wasn't.

NASA's biggest competitor became SpaceX. NASA hired SpaceX to handle many of its missions.

Tesla's shaky beginning

Tesla began shakily.

• Clients detested their roadster.

• They continued to miss deadlines.

Lotus would handle the car while Tesla focused on the EV component, easing Tesla's entry. The business experienced elegance creep. Modifying specific parts kept the car from getting worse.

Cost overruns, delays, and other factors changed the Elise-like car's appearance. Only 7% of the Tesla Roadster's parts matched its Lotus twin.

Tesla was about to die.

Elon saved the mess as CEO.

He fired 25% of the workforce to reduce costs.

Elon Musk transformed Tesla into the world's most valuable automaker by running it like a startup.

Tesla hasn't spent a dime on advertising. They let the media do the talking by investing in innovation.

Elon sheds. Elon tries. Elon learns. Elon refines.

Twitter doesn't worry me.

The media is shocked. I’m not.

This is just Elon being Elon.

• Elon makes lean.

• Elon tries new things.

• Elon listens to feedback.

• Elon refines.

Besides Twitter will always be Twitter.

More retail traders means faster, more sophisticated, and more successful methods.

Tech specifications

Only requires a laptop and an internet connection.

We'll use OpenBB's research platform for data/analysis.

Pricing and execution on Options-Quant

Background

You don't need to know the arithmetic details to use this method.

Black-Scholes is a popular option pricing model. It's best for pricing European options. European options are only exercisable at expiration, unlike American options. American options are always exercisable.

American options carry a premium to cover for the risk of early exercise. The Black-Scholes model doesn't account for this premium, hence it can't price genuine, traded American options.

Barone-Adesi-Whaley (BAW) model. BAW modifies Black-Scholes. It accounts for exercise risk premium and stock dividends. It adds the option's early exercise value to the Black-Scholes value.

The trader need not know the formulaic derivations of this model.

https://ir.nctu.edu.tw/bitstream/11536/14182/1/000264318900005.pdf

Strategy

This strategy targets implied volatility. First, we'll locate liquid options that expire within 30 days and have minimal implied volatility.

After selecting the option that meets the requirements, we price it to get the BAW implied volatility (we choose BAW because it's a more accurate Black-Scholes model). If estimated implied volatility is larger than market volatility, we'll capture the spread.

(Calculated IV — Market IV) = (Profit)

Some approaches to target implied volatility are pricey and inaccessible to individual investors. The best and most cost-effective alternative is to acquire a straddle and delta hedge. This may sound terrifying and pricey, but as shown below, it's much less so.

The Trade

First, we want to find our ideal option, so we use OpenBB terminal to screen for options that:

• Have an IV at least 5% lower than the 20-day historical IV

• Are no more than 5% out-of-the-money

• Expire in less than 30 days

We query:

stocks/options/screen/set low_IV/scr --export Output.csv

This uses the screener function to screen for options that satisfy the above criteria, which we specify in the low IV preset (more on custom presets here). It then saves the matching results to a csv(Excel) file for viewing and analysis.

Stick to liquid names like SPY, AAPL, and QQQ since getting out of a position is just as crucial as getting in. Smaller, illiquid names have higher inefficiencies, which could restrict total profits.

We calculate IV using the BAWbisection model (the bisection is a method of calculating IV, more can be found here.) We price the IV first.

According to the BAW model, implied volatility at this level should be priced at 26.90%. When re-pricing the put, IV is 24.34%, up 3%.

Now it's evident. We must purchase the straddle (long the call and long the put) assuming the computed implied volatility is more appropriate and efficient than the market's. We just want to speculate on volatility, not price fluctuations, thus we delta hedge.

The Fun Starts

We buy both options for $7.65. (x100 multiplier). Initial delta is 2. For every dollar the stock price swings up or down, our position value moves $2.

We want delta to be 0 to avoid price vulnerability. A delta of 0 suggests our position's value won't change from underlying price changes. Being delta-hedged allows us to profit/lose from implied volatility. Shorting 2 shares makes us delta-neutral.

That's delta hedging. (Share price * shares traded) = $330.7 to become delta-neutral. You may have noted that delta is not truly 0.00. This is common since delta-hedging means getting as near to 0 as feasible, since it is rare for deltas to align at 0.00.

Now we're vulnerable to changes in Vega (and Gamma, but given we're dynamically hedging, it's not a big risk), or implied volatility. We wanted to gamble that the position's IV would climb by at least 2%, so we'll maintain it delta-hedged and watch IV.

Because the underlying moves continually, the option's delta moves continuously. A trader can short/long 5 AAPL shares at most. Paper trading lets you practice delta-hedging. Being quick-footed will help with this tactic.

Profit-Closing

As expected, implied volatility rose. By 10 minutes before market closure, the call's implied vol rose to 27% and the put's to 24%. This allowed us to sell the call for $4.95 and the put for $4.35, creating a profit of $165.

You may pull historical data to see how this trade performed. Note the implied volatility and pricing in the final options chain for August 5, 2022 (the position date).

Final Thoughts

Congratulations, that was a doozy. To reiterate, we identified tickers prone to increased implied volatility by screening OpenBB's low IV setting. We double-checked the IV by plugging the price into Options-BAW Quant's model. When volatility was off, we bought a straddle and delta-hedged it. Finally, implied volatility returned to a normal level, and we profited on the spread.

The retail trading space is very quickly catching up to that of institutions.  Commissions and fees used to kill this method, but now they cost less than $5. Watching momentum, technical analysis, and now quantitative strategies evolve is intriguing.

I'm not linked with these sites and receive no financial benefit from my writing.

Tell me how your experience goes and how I helped; I love success tales.