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What if the biggest companies of
the next decade don’t even exist
yet—and you’re sitting on the
window to build one?
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We’ve been here before. In 2005,
Aaron Levie
launched
Box
when the internet was slow, browsers
were clunky, and iPhones didn’t
exist. His timing was perfect: as
mobile and cloud reshaped IT, Box
rode the wave and became a
multi-billion-dollar company.
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Now, we’re at the edge of another
seismic shift. But unlike the early
cloud era—where startups had to
convince enterprises to
believe—the script has flipped.
Enterprises are already bought in
on AI.
Leaders have used ChatGPT to draft
copy or summarize docs. They’ve seen
the magic firsthand. The vision no
longer needs selling—execution does.
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And this creates the single best
opening for founders in 10–20 years.
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The Real Opportunity: Turning
“Useless Work” into Strategic
Value
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Inside every big company sits a
treasure trove of
unstructured data: contracts,
presentations, invoices, research.
Historically, this content has been
dead weight—impossible to query,
automate, or scale. AI agents change
that.
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Even more powerful: AI frees teams
from the
“necessary but useless” work—searching files, summarizing docs,
copy-pasting data—that eats up hours
but creates zero strategic value.
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Instead of burning human capital on
repetitive tasks, companies can
redirect it to
innovation, customer time, and
proactive growth.
That’s where breakthroughs happen.
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And here’s the kicker: AI doesn’t
just replace existing work—it
unlocks the
“backlog of economically unviable
projects”
companies could never justify
staffing. Suddenly, a 50-person
startup can execute like a
500-person enterprise.
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Why Startups, Not Giants, Will
Lead
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The SaaS categories of the 2008–2014
era—CRM, payroll, email—are locked
down by incumbents. But AI is
introducing
brand-new “nouns and verbs”—entire categories of work that no
software has ever solved because it
required human expertise.
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Think specialized legal reviews,
niche research, or creative
analysis. These are greenfield
opportunities. No Salesforce, no
Gusto, no incumbent. Just wide-open
space for a scrappy startup to
dominate.
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Rethinking Business Models: From
Seats to Consumption
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Here’s where things get even more
exciting. Traditional SaaS was
capped by seats: you sold licenses
per human. But AI agents aren’t
human. They scale infinitely.
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This flips monetization to
consumption-based models:
charge per contract reviewed, per
dataset analyzed, per campaign
executed. If a human review costs
$10, and your AI agent delivers it
for $2 with better accuracy, you’ve
just redefined the economics of an
industry.
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The winning companies won’t just
sell raw AI—they’ll build
workflow software that adds
unique value and context. That’s how you preserve 80–90%
gross margins and stay defensible
even as token costs drop.
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The Founder Playbook for the AI
Era
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Aaron Levie’s advice to founders is
simple but urgent:
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Learn the classics:
Crossing the Chasm,
Innovator’s Dilemma, Blue
Ocean Strategy.
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Build with allies: Even
one strong co-founder makes
the grind survivable.
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Follow tailwinds: Focus
where AI fundamentally
transforms
a market, not where you’re
fighting incumbents.
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Think bigger: This
window won’t return for
another decade or two.
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Design matters: Great
design isn’t just aesthetic—it
makes products more usable,
more viral, and more fun to
build.
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The cloud era minted Salesforce,
Workday, and Box. The AI era will
mint the next generation of $10B+
companies.
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The only question is:
Will one of them be yours?
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Aaron Levie: Why
Startups Win In
The AI Era
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Founders: Don’t wait. Start building
where AI unlocks new value, new
workflows, and new markets. The
window is open—and it won’t stay open for
long.
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