A fascinating business conversation.

This week at Web Summit, I had mentor hour.

Mentor hour connects startups with experienced entrepreneurs.

The YC-selected founder who mentored me had grown his company to $100 million in 18 months.

I had 45 minutes to question him.

I've compiled this.

Context

Founder's name is Zack.

After working in private equity, Zack opted to acquire an MBA.

Surrounded by entrepreneurs at a prominent school, he decided to become one himself.

Unsure how to proceed, he bet on two horses.

On one side, he received an offer from folks who needed help running their startup owing to lack of time. On the other hand, he had an idea for a SaaS to start himself.

He just needed to validate it.

Validating

Since Zack's proposal helped companies, he contacted university entrepreneurs for comments.

He contacted university founders.

Once he knew he'd correctly identified the problem and that people were willing to pay to address it, he started developing.

He earned $100k in a university entrepreneurship competition.

His plan was evident by then.

The other startup's founders saw his potential and granted him $400k to launch his own SaaS.

Hiring

He started looking for a tech co-founder because he lacked IT skills.

He interviewed dozens and picked the finest.

As he didn't want to wait for his program to be ready, he contacted hundreds of potential clients and got 15 letters of intent promising they'd join up when it was available.

YC accepted him by then.

He had enough positive signals to raise.

Raising

He didn't say how many VCs he called, but he indicated 50 were interested.

He jammed meetings into two weeks to generate pressure and encourage them to invest.

Seed raise: $11 million.

Selling

His objective was to contact as many entrepreneurs as possible to promote his product.

He first contacted startups by scraping CrunchBase data.

Once he had more money, he started targeting companies with ZoomInfo.

His VC urged him not to hire salespeople until he closed 50 clients himself.

He closed 100 and hired a CRO through a headhunter.

Scaling

Three persons started the business.

1. He primarily works in sales.

2. Coding the product was done by his co-founder.

3. Another person performing operational duties.

He regretted recruiting the third co-founder, who was ineffective (could have hired an employee instead).

He wanted his company to be big, so he hired two young marketing people from a competing company.

After validating several marketing channels, he chose PR.

$100 Million and under

He developed a sales team and now employs 30 individuals.

He raised a $100 million Series A.

Additionally, he stated

• He’s been rejected a lot. Like, a lot.

• Two great books to read: Steve Jobs by Isaacson, and Why Startups Fail by Tom Eisenmann.

• The best skill to learn for non-tech founders is “telling stories”, which means sales. A founder’s main job is to convince: co-founders, employees, investors, and customers. Learn code, or learn sales.

Conclusion

I often read about these stories but hardly take them seriously.

Zack was amazing.

Three things about him stand out:

1. His vision. He possessed a certain amount of fire.

2. His vitality. The man had a lot of enthusiasm and spoke quickly and decisively. He takes no chances and pushes the envelope in all he does.

3. His Rolex.

He didn't do all this in 18 months.

Not really.

He couldn't launch his company without private equity experience.

These accounts disregard entrepreneurs' original knowledge.

Hormozi will tell you how he founded Gym Launch, but he won't tell you how he had a gym first, how he worked at uni to pay for his gym, or how he went to the gym and learnt about fitness, which gave him the idea to open his own.

Nobody knows nothing. If you scale quickly, it's probable because you gained information early.

Lincoln said, "Give me six hours to chop down a tree, and I'll spend four sharpening the axe."

Sharper axes cut trees faster.

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.

Writing for readers:

14 years of daily writing.

I post practically everything on social media. I authored hundreds of articles, thousands of tweets, and numerous volumes to almost no one.

Tens of thousands of readers regularly praise me.

I despised writing. I'm stuck now.

I've learned what readers like and what doesn't.

Here are some essential guidelines for writing with impact:

Readers won't understand your work if you can't.

Though obvious, this slipped me up. Share your truths.

Stories engage human brains.

Showing the journey of a person from worm to butterfly inspires the human spirit.

Overthinking hinders powerful writing.

The best ideas come from inner understanding in between thoughts.

Avoid writing to find it. Write.

Writing a masterpiece isn't motivating.

Write for five minutes to simplify. Step-by-step, entertaining, easy steps.

Good writing requires a willingness to make mistakes.

So write loads of garbage that you can edit into a good piece.

Courageous writing.

A courageous story will move readers. Personal experience is best.

Go where few dare.

Templates, outlines, and boundaries help.

Limitations enhance writing.

Excellent writing is straightforward and readable, removing all the unnecessary fat.

Use five words instead of nine.

Use ordinary words instead of uncommon ones.

Readers desire relatability.

Too much perfection will turn it off.

Write to solve an issue if you can't think of anything to write.

Instead, read to inspire. Best authors read.

Every tweet, thread, and novel must have a central idea.

What's its point?

This can make writing confusing.

️ Don't direct your reader.

Readers quit reading. Demonstrate, describe, and relate.

Even if no one responds, have fun. If you hate writing it, the reader will too.

Email, landing pages, and digital content

Today's most significant skill:

Copywriting.

Unfortunately, most people don't know how to write successful copy because they weren't taught in school.

I've been obsessed with copywriting for two years. I've read 15 books, completed 3 courses, and studied internet's best digital entrepreneurs.

Here are 8 copywriting frameworks that educate more than a four-year degree.

1. Feature — Advantage — Benefit (F.A.B)

This is the most basic copywriting foundation. Email marketing, landing page copy, and digital video ads can use it.

F.A.B says:

• How it works (feature)

• which is helpful (advantage)

• What's at stake (benefit)

The Hustle uses this framework on their landing page to convince people to sign up:

2. P. A. S. T. O. R.

This framework is for longer-form copywriting. PASTOR uses stories to engage with prospects. It explains why people should buy this offer.

PASTOR means:

• Problem

• Amplify

• Story

• Testimonial

• Offer

• Response

Dan Koe's landing page is a great example. It shows PASTOR frame-by-frame.

3. Before — After — Bridge

Before-after-bridge is a copywriting framework that draws attention and shows value quickly.

This framework highlights:

• where you are

• where you want to be

• how to get there

Works great for: Email threads/landing pages

Zain Kahn utilizes this framework to write viral threads.

4. Q.U.E.S.T

QUEST is about empathetic writing. You know their issues, obstacles, and headaches. This allows coverups.

QUEST:

• Qualifies

• Understands

• Educates

• Stimulates

• Transitions

Tom Hirst's landing page uses the QUEST framework.

5. The 4P’s model

The 4P’s approach pushes your prospect to action. It educates and persuades quickly.

4Ps:

• The problem the visitor is dealing with

• The promise that will help them

• The proof the promise works

• A push towards action

Mark Manson is a bestselling author, digital creator, and pop-philosopher. He's also a great copywriter, and his membership offer uses the 4P’s framework.

6. Problem — Agitate — Solution (P.A.S)

Up-and-coming marketers should understand problem-agitate-solution copywriting. Once you understand one structure, others are easier. It drives passion and presents a clear solution.

PAS outlines:

• The issue the visitor is having

• It then intensifies this issue through emotion.

• finally offers an answer to that issue (the offer)

The customer's story loops. Nicolas Cole and Dickie Bush use PAS to promote Ship 30 for 30.

7. Star — Story — Solution (S.S.S)

PASTOR + PAS = star-solution-story. Like PAS, it employs stories to persuade.

S.S.S. is effective storytelling:

• Star: (Person had a problem)

• Story: (until they had a breakthrough)

• Solution: (That created a transformation)

Ali Abdaal is a YouTuber with a great S.S.S copy.

8. Attention — Interest — Desire — Action

AIDA is another classic. This copywriting framework is great for fast-paced environments (think all digital content on Linkedin, Twitter, Medium, etc.).

It works with:

• Page landings

• writing on thread

• Email

It's a good structure since it's concise, attention-grabbing, and action-oriented.

Shane Martin, Twitter's creator, uses this approach to create viral content.

TL;DR

8 copywriting frameworks that teach marketing better than a four-year degree

• Feature-advantage-benefit

• Before-after-bridge

• Star-story-solution

• P.A.S.T.O.R

• Q.U.E.S.T

• A.I.D.A

• P.A.S

• 4P’s

WTF is wrong with you people?

When I was laid off as editor of my town's daily newspaper, I went silent on social media. I knew it was coming and had been quietly removing personal items each day, but the pain was intense.

I posted a day later. I didn't bad-mouth GateHouse Media but expressed my sadness at leaving the newspaper industry, pride in my accomplishments, and hope for success in another industry.

Normal job-loss response.

What do you recognize as abnormal?

The bullshit I’ve been reading from laid-off folks on LinkedIn.

If you're there, you know. Many Twitter or Facebook/Meta employees recently lost their jobs.

Well, many of them did not “lose their job,” actually. They were “impacted by the layoffs” at their former employer. I keep seeing that phrase.

Why don’t they want to actually say it? Why the euphemism?

Many are excited about the opportunities ahead. The jobless deny being sad.

They're ecstatic! They have big plans.

Hope so. Sincerely! Being laid off stinks, especially if, like me, your skills are obsolete. It's worse if, like me, you're too old to start a new career. Ageism exists despite denials.

Nowadays, professionalism seems to demand psychotic levels of fake optimism.

Why? Life is unpredictable. That's indisputable. You shouldn't constantly complain or cry in public, but you also shouldn't pretend everything's great.

It makes you look psychotic, not positive. It's like saying at work:

“I was impacted by the death of my spouse of 20 years this week, and many of you have reached out to me, expressing your sympathy. However, I’m choosing to remember the amazing things we shared. I feel confident that there is another marriage out there for me, and after taking a quiet weekend trip to reset myself, I’ll be out there looking for the next great marital adventure! #staypositive #available #opentolove

Also:

“Now looking for our next #dreamhome after our entire neighborhood was demolished by a wildfire last night. We feel so lucky to have lived near so many amazing and inspirational neighbors, all of whom we will miss as we go on our next housing adventure. The best house for us is yet to come! If you have a great neighborhood you’d recommend, please feel free to reach out and touch base with us! #newhouse #newneighborhood #newlife

Admit it. That’s creepy.

The constant optimism makes me feel sick to my stomach.

Viscerally.

I hate fakes.

Imagine a fake wood grain desk. Wouldn't it be better if the designer accepted that it's plastic and went with that?

Real is better but not always nice. When something isn't nice, you don't have to go into detail, but you also shouldn't pretend it's great.

How to announce your job loss to the world.

Do not pretend to be happy, but don't cry and drink vodka all afternoon.

Say you loved your job, and that you're looking for new opportunities.

Yes, if you'll miss your coworkers. Otherwise, don't badmouth. No bridge-burning!

Please specify the job you want. You may want to pivot.

Alternatively, try this.

You could always flame out.

If you've pushed yourself too far into toxic positivity, you may be ready to burn it all down. If so, make it worthwhile by writing something like this:

Well, I was shitcanned by the losers at #Acme today. That bitch Linda in HR threw me under the bus just because she saw that one of my “friends” tagged me in some beach pics on social media after I called in sick with Covid. The good thing is I will no longer have to watch my ass around that #asspincher Ron in accounting, but I’m sad that I will no longer have a cushy job with high pay or access to the primo office supplies I’ve been sneaking home for the last five years. (Those gel pens were the best!) I am going to be taking some time off to enjoy my unemployment and hammer down shots of Jägermeister but in about five months I’ll be looking for anything easy with high pay and great benefits. Reach out if you can help! #officesupplies #unemploymentrocks #drinkinglikeagirlboss #acmesucks

It beats the fake positivity.

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.