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Your first employee may be the person you're least comfortable putting in charge of your next stage of growth. They may also be carrying something your next VP can't easily replace. This week's feature gets into what those early hires accumulate, why the damage grows as companies mature, and what you ought to know before reorganizing the people who helped build your business.

In this issue
■ The Department of Homeland Security proposes a new fee crafted to make it more difficult to hire international graduates
■ How a lofty fundraising valuation can come back to bite you when you start talking to potential suitors
■ Learn the risks to your business should AI get dramatically better in 2027, which it most certainly will
The gauge
41%

AI tokens have gotten considerably cheaper. Ramp's spending data puts the effective price per million tokens at $0.68, down 41% from a March peak of $1.15 (Ramp). There's a catch to using that figure in your pricing model. It's an average across what Ramp's business customers buy, and your cost for a particular task may have fallen more or less than that. Either way, cheaper models can let competitors include AI in their base price, which makes it harder to charge extra for basic AI features.

Gear changes
What moved for founders this week
Student work authorization fees

The $70,000 OPT fee could reach employees already on your payroll

The Department of Homeland Security wants to charge universities $70,000 to recommend an international student for their first period of Optional Practical Training (OPT), with a $30,000 fee for subsequent periods after the initial fee has been paid (Federal Register).

Schools pay before a student can apply

The money is due before the school recommends the student for work authorization. Schools may pass the bill to students or employers, even though DHS says the fee isn't attached to a particular employer. DHS picked a fairly unusual way to introduce a potentially enormous hiring expense.

An existing employee could be affected, too

The proposal leaves this case open, and a STEM OPT extension issued after the rule takes effect could trigger the full $70,000 initial fee if no fee has previously been paid under the new system.

This remains a proposal. Comments close in early November, and any final rule would take effect 60 days after publication. The payment arrangements between schools, students and employers are still unresolved.

Founder read: A flat $70,000 fee is a radically different investment for a new graduate than for an experienced specialist. If schools pass the cost to employers, the proposal could make entry-level international hiring unusually difficult to justify, even where the candidate is a strong fit. Companies that depend on developing junior technical talent would face a second-order problem: fewer viable opportunities to build that talent internally, with greater reliance on experienced hires later.

Also this week

Cloudflare bought Deno. Deno Deploy customers got six months to leave.

Cloudflare acquired Deno on Oct. 9, and Deno co-founder Ryan Dahl announced two deadlines for the products customers currently use. Deno Deploy, the hosting service, will shut down in six months. The standalone Deno runtime gets another year of monthly security patches and bug fixes before Deno ends its development. Paying Deploy customers will receive migration help, specifically for moving to Cloudflare Workers. The JSR package registry continues operating (Deno). Founder read: Deno has effectively given developers two separate decisions. Deploy customers must find another hosting platform within six months. Teams that continue running the Deno runtime will eventually need someone responsible for security maintenance after official development ends. Open-source availability preserves the code, but continued maintenance depends on people doing the work. A hosting migration can be completed successfully while leaving the more consequential dependency unresolved.

Airtable and Miro found buyers at a fraction of their former valuations

Bending Spoons completed its acquisition of Airtable in September at an enterprise value of about $1.3 billion. It has also agreed to buy Miro for about $1.4 billion, with that deal still awaiting closing. Both companies were once valued vastly higher. PitchBook describes the transactions as nearly 90% below their previous private valuations, although those prices are enterprise values, compared against earlier private valuations. There are now 992 private unicorns with a combined reported value of $5.7 trillion, according to PitchBook's third-quarter Venture Monitor. Those valuations are difficult to reconcile with the prices some buyers are willing to pay (PitchBook). Founder read: At the time you raise, a higher valuation may look like an unqualified win. Later, it can make an otherwise attractive acquisition difficult for investors or employees to accept. A founder who expects a strategic sale rather than an IPO should know what exit values make the current financing terms work. That analysis might favor raising less capital, keeping more ownership or accepting slower growth. The goal is preserving attractive choices when a buyer eventually arrives.

California won't accept an AI-generated firing decision on faith

California's new "No Robo Bosses Act" takes effect in 2027. Under SB 947, an employer can't discipline or fire someone based solely on an automated decision system. When an employer primarily relies on such a system, a human must corroborate the result using additional evidence, and the employee must receive written notice. If that reviewer can't verify the result, the employer can't use it to support the decision. A manager rubber-stamping a performance score isn't the review the law describes (National Law Review). Founder read: For companies selling AI-powered workforce management tools, compliance may depend on features buyers previously treated as secondary: evidence trails, reviewer controls, records of corrections and proof that notices were provided. These requirements also create a competitive distinction. A system built around an opaque performance score may require substantial redesign, while one that already preserves reviewable evidence could fit more easily into employers' approval processes.
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The 10-year cost of losing an early hire

Research on millions of U.S. startups found that losing an employee from the company's first year could leave a gap lasting a decade.

A startup can spend years recruiting better executives, building stronger teams and getting the right people into the right jobs. Yet one of the employees it can least afford to lose may be someone hired before any of those jobs existed.

Four economists studied what happened when startups unexpectedly lost employees who had joined during their first year. Revenue fell about 14% immediately after the loss. Across the following five years, the affected companies averaged roughly 12% less revenue than comparable businesses. The researchers found that the effects persisted for at least a decade.

Replacement hiring hadn't closed the gap.

The findings complicate a familiar piece of startup advice: As the company grows, some of the people who helped build it will need to make way for more experienced talent.

Elad Gil addresses this directly in his High Growth Handbook. He describes founders trying to find an early employee somewhere "where they won't do much harm, versus a place they will excel." When a founder reaches that point, Gil writes, "99% of the time the right answer is to part ways with the early employee."

It's advice about a specific problem: someone whose abilities no longer fit the company's needs.

But the researchers found that the consequences of losing an early employee grew larger as companies matured. Apparently, those first hires can accumulate something that becomes increasingly difficult to replace.

An unusually permanent vacancy

The researchers, Joonkyu Choi, Nathan Goldschlag, John Haltiwanger and J. Daniel Kim, had access to Census Bureau records covering more than 6 million U.S. startups established between 1990 and 2015.

Their problem was figuring out what employees contributed to company performance.

Ordinary turnover makes that difficult. Strong employees may leave struggling companies. Poor performers may get fired. A company may start shrinking months before anyone resigns. Comparing companies that lose employees with those that retain them would mix up cause and effect.

The economists used premature deaths instead.

They identified approximately 25,000 startups where a founder or early employee died at age 60 or younger while still working for the business. They matched those companies with similar businesses that experienced no such death, creating a sample of roughly 52,000 firms. The average company had about 15 employees in the year of the death.

The distinction between founders and early employees was deliberate. An "early joiner" was a non-founder who appeared on the payroll during the company's first year.

The researchers compared what happened afterward. When a company lost an early joiner, employment initially fell about 10% and revenue about 14%. Over the subsequent five years, the estimated gaps averaged approximately 8% and 12%, respectively.

Even after 10 years, the researchers reported that the effects "do not dissipate."

Then they repeated the exercise for employees hired during a startup's second year.

Those departures also hurt. But the damage peaked within about two years and became statistically insignificant by year five.

Apparently, something happened during the first year of a company's life that made those employees unusually consequential.

The knowledge that never made it into a job description

The economists' explanation centers on what they call "organizational capital that emerges at firm formation."

It's an academic term for something founders encounter constantly: the accumulated knowledge of how a particular business operates.

Consider what the first customer-success employee might know at a B2B software company. They may understand why an important customer's contract includes an unusual provision, which product limitations have been privately negotiated around, and how the company learned to handle an implementation problem that once threatened a renewal.

Some of that information eventually becomes documentation. Much of it may remain in the employee's judgment, habits and relationships.

An experienced replacement might be considerably better at managing a customer-success organization. That experience doesn't automatically provide the history behind decisions made before the replacement arrived.

The researchers describe this as "the firm-specific human capital embodied in early joiners accumulating over time as they remain at the firm."

They found supporting patterns in the results.

The loss was more damaging in companies six to 11 years old. It was also larger in teams of five or fewer and when the departing initial-team member had earned more before joining the startup.

The B2B results were particularly pronounced.

In business-to-business-intensive industries, losing an early joiner produced an additional decline of approximately 4.7% in employment and 9.1% in revenue relative to consumer-facing industries. The researchers calculated that these additional effects were 79% and 115% larger than the respective baseline effects in consumer-facing businesses.

The authors point to the importance of specialized relationships between businesses as a possible explanation.

That interpretation makes sense for a software company whose oldest employees have spent years learning customers' operations and accommodating requirements that were never entirely captured in a contract. But the researchers didn't directly measure the loss of individual relationships, undocumented decisions or customer knowledge. Their findings support the organizational-capital explanation without identifying exactly which pieces of knowledge account for the losses.

And the study covered startups across industries, rather than B2B SaaS companies specifically.

Gil's advice still has a place

There is one enormous difference between the departures in this study and the staffing decisions founders usually face.

Death is sudden, involuntary and accompanied by circumstances that a planned departure ordinarily avoids. There is no opportunity for a deliberate handover. The study may also capture the disruption of losing a colleague under tragic circumstances.

The economists deliberately avoided resignations and dismissals because those events are influenced by company performance and employee characteristics. They left that research for another day.

Consequently, their estimates cannot tell a founder what happens when an underperforming early employee leaves after a managed transition. A 12% revenue gap in the research sample is no basis for predicting the cost of an individual firing.

Gil, meanwhile, offers another option before separation. When an early employee no longer fits the position, he recommends trying to move the person into a role where they can succeed, even if that means accepting a demotion.

Foundation Capital's Charles Moldow makes a related observation about the first 20 employees: "The employees who got you to this point don't necessarily possess the skills to take you to the next stage."

Both assessments can be correct. An employee may have reached the limits of their management ability while retaining substantial value through customer relationships, product history and judgment accumulated during the company's earliest years.

That possibility deserves attention when the founder decides to bring in a more experienced executive.

The incoming leader's responsibilities can include learning which customer relationships depend on the early employee, what institutional knowledge remains undocumented and whether there's a meaningful role for that person after the reorganization.

Retention may require compensation, an equity refresh or an appropriate change in responsibilities. A departure may still be necessary. The research establishes no universal financial return from retaining someone who no longer fits.

But it provides a reason to examine the company's accumulated knowledge before treating an early employee's departure as an ordinary replacement exercise.

When the next senior executive takes over a function, someone needs to account for the decisions, relationships and history that predate the hire. The founder should know how much of that knowledge remains with the employee whose job is about to change.

The Prime
What to read, watch or use this week
Shahar Azulay opened his first sales negotiation at $100,000. He left with a three-year contract at $10,000 a year for software that didn't even have a user interface yet. He still says underselling was the right call. Listen from 17:49 to 24:41, where he explains why getting those first deals mattered more than their contract values, and how he eventually published a list price while offering discounts as steep as 70%. His approach makes more sense for a founder learning to sell an unfinished product than for a company with an established customer base.
Prepaid credits sound appealing until renewal time, when the customer wants to commit less and your sales team wants them to commit more. Chargebee describes a way around that annual argument: set the next year's commitment based on what the customer consumed. Read "The renewal problem with credits" for the mechanics, then "How to set the credit-to-dollar ratio" to see how individual AI actions get priced. Skip the closing sales pitch. Chargebee sells the billing infrastructure for these systems, but the underlying commercial decisions are useful regardless of platform.
How exposed is your business if AI gets dramatically better over the next two years? SaaS Capital proposes an assessment that includes an uncomfortable distinction: software that analyzes someone else's system of record starts with a weaker position than software that owns the underlying data. Read "Rating Dimension Definitions" and score your company on system of record, non-software complements, and user and usage. The framework was validated against 52 public SaaS companies. It's useful for challenging your assumptions about defensibility, although a private company's score is necessarily more speculative.
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Before you go
How I can help you

I run The Pricing Reset, a six-week engagement for founders of sales-led B2B SaaS companies whose product has outgrown the pricing they set a few years ago. I rebuild the packaging, price points and discount rules, then help put the new pricing live on new deals so the team can run it without every exception landing on the founder.

The work continues through a 90-day measurement window, with check-ins at days 30, 60 and 90 and a final readout against the company's own starting numbers.

If your pricing has not kept pace with the product, book a 20-minute call at redwoodridge.net/book, or reply with your current pricing page. I'll tell you whether The Pricing Reset applies and, if it doesn't, what I'd look at instead.

Thanks for reading. See you next Wednesday.
— Jason

P.S. When one of your earliest employees left, what was the first thing your team discovered it didn't know? Hit reply with the story. I'm especially interested in what the handoff left out.