Last year I wrote a post about Reese Witherspoon.
It ended up doing around 800k impressions and 21k likes on LinkedIn.
Which honestly surprised me at the time… but the more I looked at the comments, the more obvious it became why it landed.
People were reacting to a story about what they all want: control.
By the mid-2010s, Witherspoon’s acting career had stalled.
Not really in visibility, but in opportunity.
The supply of serious female-led roles was limited and decisions about what got made sat with studios and financiers, not actors.
Reese identified the real constraint: she did not control which stories entered the production pipeline.
So she launched Reese’s Book Club, as a way to observe demand at scale.
Studios decide based on scripts and internal taste.
She decided based on audience response.
Once a book demonstrated traction, she acted through Hello Sunshine.
The core move was acquiring adaptation rights early.
Sometimes this meant optioning IP directly.
Sometimes it meant securing rights of first refusal.
In both cases, she positioned herself between the author and any future buyer.
This is the critical point.
She acquired rights before books were priced as proven IP.
When a book showed sustained demand and the projects were pitched to HBO, Hulu, or Apple, they already had:
validated audiences
clear positioning
lower downside risk
This is why projects like Big Little Lies, Little Fires Everywhere, The Morning Show, and Daisy Jones & The Six moved quickly once pitched.
The work had been done upstream.
By 2021, Hello Sunshine had a repeatable strategy:
early sourcing
audience validation
rights acquisition
selective scaling
external capital for distribution
That is why the company sold at a valuation near $900M.
And this generalizes beyond media.
Reese built an audience before building a product, prioritized ownership over exposure, and partnered with incumbents only after risk was removed.
Takeaway: She did not try to be chosen. She chose what to own.
Photo: Harper’s Bazaar
The 83(b) election: a 30-day decision with million-dollar consequences
An 83(b) election is a short IRS filing that founders use when they receive unvested stock.
It lets you choose to be taxed on the value of your shares at the time they are granted, rather than as they vest.
By default, the IRS taxes stock when it vests, not when it’s issued.
So if:
you receive 4,000,000 founder shares
they vest over 4 years
the company’s value increases over time
Then each vesting event is treated as taxable income, based on the fair market value at that moment.
That means you can owe taxes on stock you cannot sell, cannot liquidate, and may never realize value from…
This is how founders end up with six-figure tax bills and no cash.
An 83(b) election tells the IRS: “Tax me now, at today’s value, not later.”
If you file it:
you pay tax on the initial grant value
future appreciation is not taxed as income
gains are taxed later as capital gains when you sell
For early founders, the initial value is usually close to zero.
A simple example…
Founder receives 4,000,000 shares at $0.0001 per share. Total value = $400.
If they file 83(b), they pay tax on $400. Done.
If they do not file 83(b), after one year, 1,000,000 shares vest, company raises at $1/share. IRS treats that as $1,000,000 of income. Tax bill arrives even though the shares are illiquid
And timing matters more than anything.
The 83(b) must be:
filed within 30 days of stock issuance
physically sent to the IRS
properly documented
Miss the deadline and the option disappears permanently.
So do not rely on platforms or lawyers to “handle it for you” without confirmation
This is a founder responsibility.
Why does every founder default to raising VC…?
VC has become the default framing for ambition even when it’s structurally wrong for the business being built.
Somewhere along the way “Announcing our oversubscribed $5M seed round” became the default founder milestone.
Most founders don’t choose venture capital because they’ve analyzed capital requirements, exit paths, or even ownership trade-offs.
They choose it because VC is treated as the serious path. The one that signals legitimacy and scale.
But it rewards speed before control.
Founders are encouraged to raise early to “move fast”, to scale… then they have to deal with dilution, messy cap tables, or weak control.
VC is designed to finance a very specific kind of outcome: extreme scale, extreme risk, and a small number of outsized winners.
But most companies are not building for that outcome.
Of course, if your product requires regulatory clearance, clinical trials, expensive infrastructure… bootstrapping will just delay progress while competitors move faster with capital.
But to make an educated decision, the question founders should really be asking themselves is: right now, will outside capital increase the speed and quality of my decisions?
Most unhinged questions female founders got asked by VCs
1. “Are you planning to have kids?”
What it’s testing: commitment risk.
Why it’s unhinged: would you ask a guy “Do you plan on getting any woman pregnant?”
2. “You seem very prepared. Did someone help you with this deck?”
Men: “Great instincts.”
Women: “Who coached you?”
3. “Aren’t you a little young. to be a founder?”
Said to a 24-year-old woman.
4. “Is this really a problem worth solving?”
About: women’s health, education, labor, fertility.
5. I’ve had bad experiences with female founders. How emotional do you get when you’re criticized?”
No comment.
The worst pitch deck mistake
Titling your slides “The Problem,” “The Product,” “The Market,” “The Team”.
Don’t announce that there is a problem.
Obviously there is one... otherwise you wouldn’t be pitching.
Instead say, “Fortune 500 companies overspend $1M/year on unused software licenses.”
Don’t say you have a product. Everyone does.
Explain what changes the moment it exists.
What pain disappears. What decision gets easier. What the customer suddenly gains.
"Novatech reduces time to diagnosis from 4.8 years to 6 weeks"
The slide title should summarize the entire slide.
It should be the one thing I remember.
This sounds obvious, but roughly a third of the decks I see don’t do it.
If you’re working on a pitch deck and would like thoughtful feedback, I’d love to help.
With your permission, I’ll feature an anonymized version of your slides in the newsletter (confidential details removed) alongside a breakdown of my feedback. You can reach me at [email protected].