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AI Just Completely Wiped Out This $14B Company
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Plus: 34% of hourly workers rely on more than 1 job, a $400K side hustle fixing resumes, and tips for more passive income in 2026. ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏ ͏
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Presented by:
</span>
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</h2>
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<p style="font-weight: bold; font-size: 17px; margin-bottom: 6px; color: #111111;">
APRIL 30, 2026
</p>
<p style="font-weight: bold; font-size: 15px; margin-bottom: 10px; color: #0073e6;">
What's on deck today:
</p>
<ul style="margin-top: 0; margin-bottom: 0; padding-left: 22px; color: #333333;">
<li>
A cautionary tale about AI wiping out a business model overnight
</li>
<li>
Over 33% of hourly workers juggle multiple jobs just to survive
</li>
<li>
This person built a $400K side hustle fixing resume mistakes
</li>
<li>
What's up with passive income in 2026?
</li>
</ul>
<hr style="border: 0; border-top: 1px solid #e0e0e0; margin: 18px 0;"/>
<p style="font-weight: bold; font-size: 15px; margin-bottom: 10px; color: #0073e6;">
Market snapshot:
</p>
<ul style="margin-top: 0; margin-bottom: 0; padding-left: 22px; color: #333333;">
<li>
S&P 500
<span style="color: #cc0000;">
▼ 0.02%
</span>
</li>
<li>
Dow Jones
<span style="color: #cc0000;">
▼ 0.56%
</span>
</li>
<li>
NASDAQ
<span style="color: #cc0000;">
▼ 0.06%
</span>
</li>
</ul>
</div>
</div>
</div>
</td>
</tr>
</tbody>
</table>
<table cellpadding="0" cellspacing="0" class="" role="presentation" style="" width="100%">
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<a data-hs-link-id="0" data-hs-link-id-v2="mNZSdVnv" rel="noopener" style="text-decoration:none; font-weight:bold; color:#000000" target="_blank">
This $14 Billion Business Is Officially the First Company to Be Completely Wiped Out By AI
</a>
</span>
</span>
</span>
</span>
</h2>
</div>
</div>
</td>
</tr>
</tbody>
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<div style="line-height:175%">
<p style="line-height:150%">
<span style="font-weight: bold;">
Once the darling of Wall Street, Chegg is a cautionary tale of what happens when AI makes your entire business model obsolete overnight.
</span>
There was a time when investors and students loved the edtech company that helped with homework for $14.95 a month. Then generative AI showed up.
</p>
</div>
<p style="line-height:150%">
</p>
<p style="line-height:150%">
In February 2021, Chegg’s stock traded at $115 with a market cap of $14.7 billion. The COVID-19 pandemic had driven record demand for online education, and Chegg capitalized. But AI tools like ChatGPT and Claude offered instant answers for free, making Chegg obsolete.
</p>
<p style="line-height:150%">
</p>
<p style="line-height:150%">
The company tried to
<a data-hs-link-id="0" data-hs-link-id-v2="5vfr28js" style="color:#2563eb" target="_blank">
fight back with CheggMate
</a>
, an AI chatbot trained on its proprietary homework database. The gambit failed. Chegg laid off 248 employees in May 2025 and 388 employees (45% of staff) in October 2025, blaming “new realities of AI.” Today,
<a data-hs-link-id="0" data-hs-link-id-v2="wEMzWJMq" style="color:#2563eb" target="_blank">
the stock trades at $1.02
</a>
with a market cap of $114.59 million. The company has struggled to stay above the $1 threshold and nearly got kicked off the New York Stock Exchange.
</p>
</div>
</div>
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<h2 align="left" style="margin:0; font-size:14px; line-height:160%; font-weight:normal; text-align:left">
<span style="color: #425b76; font-family: Helvetica, Arial, sans-serif; font-size: 13px;">
<span style="--darkreader-inline-color: #e5e0d8;">
SPONSORED MESSAGE
</span>
</span>
</h2>
<p style="line-height:175%">
<span style="color: #425b76; font-family: Helvetica, Arial, sans-serif; font-size: 13px;">
</span>
</p>
<h2 align="left" style="margin:0; font-size:22px; line-height:115%; text-align:left; font-weight:bold">
<span style="font-family: Tahoma, sans-serif;">
<strong>
The Founders Who Built Their Businesses on Resistance
</strong>
</span>
</h2>
</div>
</div>
</td>
</tr>
</tbody>
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<img align="middle" alt="Building_against_resistance" src="https://inboxflows.com/_/image/https%253A%252F%252Fhs-21266006.f.hubspotemail.net%252Fhub%252F21266006%252Fhubfs%252FBuilding_against_resistance.webp%253Fwidth%253D1160%2526upscale%253Dtrue%2526name%253DBuilding_against_resistance.webp/?inbox_flows_img_sig=eyJwYXRoIjoiaHR0cHMlM0ElMkYlMkZocy0yMTI2NjAwNiIsInRpbWUiOjE3Nzc1NDY3OTEuMzM0NDY4OH0:1wIP7X:N8mDKIcLTHGdBtmhElU-mOD2LGALiqrTuXMP_dku0MM" style="outline:none; text-decoration:none; border:none; max-width:100%; font-size:16px; border-radius:2%" width="580"/>
</a>
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📈
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BUSINESS BREAKDOWN
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I Turned Resume Mistakes Into a $400K Side Hustle
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<span style="font-style: italic;">
This as-told-to story is based on a conversation with Seattle, Washington attorney and entrepreneur Jennifer Clinchy. The National Oceanic and Atmospheric Administration’s (NOAA) only enforcement attorney in the Pacific Northwest, Clinchy runs
</span>
<a data-hs-link-id="0" data-hs-link-id-v2="ki4Mm2Jc" style="color:#2563eb; font-style:italic" target="_blank">
Clinchy Career Consulting
</a>
<span style="font-style: italic;">
, offering resume consulting,
</span>
cover letter
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writing and LinkedIn optimization services, as a
</span>
side hustle
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. She launched the consulting side hustle on
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Fiverr
<span style="font-style: italic;">
in 2020 and hit $250,000 in total earnings on the platform last year.
</span>
</p>
<p style="line-height:150%">
</p>
<p style="line-height:150%">
When I was working at the White House from 2010 to 2017, I served as a hiring manager and as legal counsel there. As part of that role, I reviewed thousands of resumes from some of the most talented candidates in the country. It really showed me both how highly qualified people can have incredibly compelling resumes, as well as some surprisingly weak ones that don’t do justice to all of the skills and experience that they bring.
</p>
<p style="line-height:150%">
</p>
<p style="line-height:150%">
When I left the White House in September 2017 to accept a position with the Washington State government as director of policy and planning at Puget Sound Partnership (a state government agency), I took a 30% pay cut. During the transition, I considered starting a side hustle — and realized that many friends, colleagues, former mentees and junior employees had come to me over the years asking for advice on resumes.
</p>
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Resume writing is something that I’ve always just personally enjoyed for my own resume. It’s always a work in progress, so I was constantly reading up on different trends and best practices, and one of my friends said, “You know, you’re actually pretty good at this resume writing thing. Have you ever thought about trying to do this professionally?” I hadn’t, but I realized the skillset would transfer well.
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Quick Hits
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<a data-hs-link-id="0" data-hs-link-id-v2="MurJFSZG" rel="noopener" style="text-decoration:none; font-weight:normal; color:#000000" target="_blank">
→ Why Entrepreneurs are Adding This
<span style="text-decoration: underline; color: #0600ff;">
$50 Bitcoin Mine
</span>
r to Their Desks
</a>
</span>
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→ The Honest Truth About
<span style="text-decoration: underline; color: #0600ff;">
Passive Income in 2026
</span>
</a>
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<a data-hs-link-id="0" data-hs-link-id-v2="PqVbi3Bh" rel="noopener" style="text-decoration:none; font-weight:normal; color:#000000" target="_blank">
→
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Microsoft Expects
</span>
Headcount to Decrease in Coming Quarters
</a>
</span>
</p>
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Do This Today ✅
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<strong>
The Insight:
</strong>
Teams collaborate better when there’s a clear, emotionally compelling cause (not just a task list). When people understand and
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feel the mission,
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they self‑align, need less micromanagement and are more willing to solve problems together.
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<br/>
<strong>
Do This:
</strong>
Draft a 2‑sentence “today’s mission” for your team that ties one concrete outcome (e.g., launch X, unblock Y client, fix Z issue) to your broader purpose. Post it in your team channel and open the day’s stand‑up by reading it and asking each person how they’ll contribute.
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1 week, 3 days ago - info@n.entrepreneur.com
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