The Information Newsletter: Jessica Lessin's Premium Tech Journalism ($399/Year)
The definitive guide to The Information—Silicon Valley's most exclusive tech newsletter with 6 specialized editions, proprietary scoops, and insider access. Founded by former WSJ journalist Jessica Lessin in 2013.
Trusted by tech executives, venture capitalists, and industry insiders who need strategic intelligence, not just news.
Quick Facts: The Information
Founder
Jessica Lessin (former WSJ)
Founded
December 2013
Pricing
$399/year ($39/month)
Newsletters
6 specialized editions
Headquarters
San Francisco, CA
Team Size
~60 employees
Focus
Exclusive tech scoops
Business Model
100% subscription (no ads)
Pro Tier
$999/year (data access)
The Information vs. Other Premium Tech Newsletters
| Newsletter | Price/Year | Focus | Best For |
|---|---|---|---|
| The Information | $399 | Exclusive tech scoops & analysis | Executives, VCs, tech pros |
| Stratechery | $150 | Tech business strategy | Strategic thinkers, PMs |
| Not Boring | $100 | Tech trends & deep dives | Founders, investors |
| CB Insights | $2,000+ | Market intelligence & data | Corporate strategy teams |
| StrictlyVC | $300 | VC ecosystem & deals | VC professionals |
Most tech professionals subscribe to 3-5 premium newsletters = $1,000-$5,000/year
Key Takeaways
- Founded by Jessica Lessin (former Wall Street Journal tech reporter) in December 2013
- $399/year standard subscription ($39/month), with Pro tier at $999/year for proprietary data
- 6 specialized newsletters: The Briefing (daily), AI Agenda, Dealmaker, AI Infrastructure, Applied AI, The Weekend
- 100% subscription-based—no advertising revenue, enabling deeper investigative journalism
- 60-person newsroom in San Francisco producing exclusive Silicon Valley scoops
- Consolidate with Readless to maximize ROI from The Information + other premium sources
What is The Information?
The Information is a subscription-based technology news website founded by journalist Jessica Lessin in December 2013. Lessin, a former Wall Street Journal technology reporter, created The Information to deliver exclusive, deeply-reported scoops and analysis on Silicon Valley without the constraints of ad-driven journalism.
Unlike free tech news sites like TechCrunch or The Verge that rely on advertising revenue and prioritize speed and volume, The Information operates on a 100% subscription model ($399/year). This enables the 60-person newsroom to focus on investigative journalism, insider access to executives and venture capitalists, and exclusive scoops that break days before competitors report them.
Why The Information Costs $399/Year
The subscription-only model means no clickbait, no SEO optimization, no viral headline chasing. Reporters spend weeks on investigative pieces. The newsroom has deep Silicon Valley relationships that provide insider access to boardrooms, funding rounds, and strategic decisions before they become public.
- Exclusive scoops: The Information regularly breaks major tech stories 12-48 hours before mainstream outlets
- No advertising influence: Reporters aren't pressured to avoid critical coverage of advertisers
- Quality over quantity: Focus on strategic intelligence for decision-makers, not daily news volume
- Proprietary data (Pro tier): Databases tracking 4,000+ tech industry individuals, org charts, market trends
Who is Jessica Lessin?
Jessica Lessin is a veteran technology journalist who covered tech for The Wall Street Journal before founding The Information in 2013. Her vision was to create a publication that serves tech industry professionals—not casual readers—with the depth and insider access they need to make strategic decisions.
Under her leadership, The Information has become one of the most respected sources for tech industry intelligence, competing with established outlets through exclusive reporting and deep Silicon Valley relationships. The publication has broken major stories on companies like Meta, Apple, Google, OpenAI, and dozens of unicorn startups.
How The Information is Different
TechCrunch / The Verge
- • Free, ad-supported
- • Hundreds of articles daily
- • Focus on speed & SEO
- • General tech audience
- • Breaking news emphasis
The Information
- • $399/year subscription
- • Quality over quantity
- • Investigative depth
- • Tech professionals only
- • Exclusive insider access
The Information Pricing & Subscription Tiers
STANDARD
$399
per year
($39/month if billed monthly)
- Access to all 6 newsletters
- Exclusive reporting & scoops
- Full article archive
- Mobile app access
- Best for: Executives, PMs, tech professionals
INFORMATION PRO
$999
per year
(launched Feb 2023)
- Everything in Standard
- Proprietary databases (4,000+ people tracked)
- Exclusive org charts (50 companies)
- Market trend datasets
- Monthly reader surveys
- Best for: VCs, C-suite, corporate strategy teams
YOUNG PROFESSIONAL
$225
per year
(age 30 and under)
- All Standard features
- Access to events
- Exclusive community
- Discounted rate (44% off)
- Best for: Early-career tech professionals, students
The Premium Subscription Problem
Annual Spend
The Information ($399) + Stratechery ($150) + Not Boring ($100) + CB Insights ($2,000) = $2,649/year
Actual Usage
Most professionals only deeply read 30-40% of premium content due to overwhelm
Wasted Value
Reading only 30% = $1,800/year wasted in unused subscription value
Readless helps you actually use what you're paying for
Maximize My Premium SubscriptionsWho Subscribes to The Information?
The Information is designed for tech industry professionals who need strategic intelligence, not casual readers. Here's how Readless helps different audiences maximize their premium subscriptions.
Tech Executive (C-Suite)
Annual Premium Spend:
$5,000-$15,000/year
Typical Sources:
The Information ($399), Stratechery ($150), CB Insights ($2,000+), Not Boring ($100), industry research
Pain Point:
Subscribe to 10-15 premium sources but only deeply read 30% due to overwhelm
Readless Solution:
Morning digest surfaces what matters from each source. Click through to read full premium content when relevant.
ROI:
90% utilization rate vs. 30% = $4,500+ value unlocked from existing subscriptions
Venture Capital Investor
Annual Premium Spend:
$10,000+/year
Typical Sources:
The Information Pro ($999), StrictlyVC ($300), Pitchbook ($7,000+), CB Insights, Dealmaker newsletters
Pain Point:
Deal flow intelligence scattered across 20+ sources. Miss critical funding rounds or trends.
Readless Solution:
Daily digest consolidates deal flow + AI spots emerging patterns across sources
ROI:
One early insight on promising startup = ROI for entire year of tools + Readless
Product Manager / Tech Lead
Annual Premium Spend:
$1,500-$3,000/year
Typical Sources:
The Information ($399), Stratechery ($150), Not Boring ($100), Lenny's Newsletter, Product Management newsletters
Pain Point:
All sources provide valuable insights but reading 5+ premium newsletters weekly = 90+ minutes
Readless Solution:
Weekly digest helps prioritize which articles to read in full. Never miss competitor moves or tech trends.
ROI:
Better product decisions from actually consuming all sources. 60 min weekly → 15 min = 180 hours/year saved
Founder / Startup Operator
Annual Premium Spend:
$800-$2,000/year
Typical Sources:
The Information ($399), Not Boring ($100), The Generalist ($200), YC Library, startup newsletters
Pain Point:
Need to stay informed on tech trends, fundraising landscape, and competitive intelligence but limited time
Readless Solution:
Daily or weekly digest keeps you informed without the time drain. Focus on building.
ROI:
Competitive intelligence + trend spotting = fundraising advantage worth 100x the subscription cost
The Information vs. Other Premium Tech Newsletters
Detailed comparison of premium tech newsletters to help you choose the right mix
| Newsletter | Price/Year | Pro Tier | Focus | Target Audience | # Newsletters |
|---|---|---|---|---|---|
| The Information | $399/year | $999/year | Exclusive tech scoops & analysis | Executives, VCs, tech professionals | 6 specialized newsletters |
| Stratechery | $150/year | $180/year (Daily Update) | Tech business strategy & analysis | Strategic thinkers, product managers | 3 weekly updates |
| Not Boring | $100/year | N/A | Tech trends & business deep dives | Founders, investors, enthusiasts | Weekly essays |
| CB Insights | $2,000+/year | Enterprise pricing | Market intelligence & data | Corporate strategy teams, investors | Research briefs + database access |
| StrictlyVC | $300/year | N/A | VC ecosystem & deals | Venture capital professionals | Daily VC news |
When to Choose The Information
- You need exclusive scoops breaking 12-48 hours before mainstream outlets
- Insider access matters—boardroom decisions, funding rounds, strategic moves
- You're a decision-maker who needs intelligence, not just news updates
- Multiple specializations—6 newsletters covering AI, VC deals, infrastructure, etc.
Or Subscribe to Multiple & Consolidate
Most tech executives subscribe to The Information AND Stratechery AND Not Boring AND CB Insights. That's $2,600+/year and 90+ minutes daily across 15+ emails per week.
Readless consolidates all of them into one 12-minute digest, removes duplicate coverage (e.g., the same OpenAI funding round covered by 5 sources), and organizes everything by topic.
Learn how Readless works →How Readless Handles The Information (and Other Premium Newsletters)
Forward The Information Newsletters
Set up forwarding from your Information newsletters (The Briefing, AI Agenda, Dealmaker, etc.) to your @mail.readless.app address. Or subscribe directly to The Information using your Readless address. Works with Stratechery, Not Boring, CB Insights, and any premium newsletter.
AI Extracts Key Insights
Readless AI processes each Information newsletter, extracting the main scoop, key data points, and unique insights. Preserves source attribution so you can cite The Information in executive briefings or investor memos.
Your original premium content remains private, encrypted, and accessible only to you
Cross-Source Intelligence
AI spots connections across your premium sources: "The Information reports OpenAI raised $6.6B at $157B valuation, Stratechery analyzes strategic implications for Microsoft partnership, CB Insights shows this is 44% higher than last round."
Example: When 5 newsletters cover the same funding round, you get one consolidated summary with the unique angle from each source—not 5 separate articles saying the same thing.
Smart Prioritization & Click-Through
Digest shows which Information articles deserve deep reading vs. which are just FYI. Click through to access complete original premium content (paywalled articles remain behind The Information's paywall). Never miss exclusive scoops that matter to your work.
Before Readless vs. With Readless
Before Readless
6:00 AM - The Briefing arrives (12 min)
7:00 AM - Stratechery daily update (10 min)
8:00 AM - CB Insights research brief (15 min)
9:00 AM - AI Agenda newsletter (8 min)
Weekly - Dealmaker + Not Boring (20 min each)
Total: 90+ minutes daily, scattered across morning. Only read 30% due to overwhelm.
With Readless
6:00 AM - One consolidated digest (12 min)
- ✓ All stories from all premium sources
- ✓ Duplicates removed (AI detects same scoop across sources)
- ✓ Organized by topic: AI, Funding, Strategy, Industry
- ✓ Click through to full Information articles when needed
- ✓ Cross-source intelligence (connections you'd miss)
Total: 12 minutes, one focused read. 90% utilization rate of all sources. Save 78 minutes daily = 325 hours/year.
Calculate Your ROI: The Information + Other Premium Newsletters
| Scenario | Annual Cost | Usage Rate | Effective Value |
|---|---|---|---|
| Before Readless The Information ($399) + Stratechery ($150) + Not Boring ($100) + CB Insights ($2,000) + others | $5,000 | 30% read | $1,500 value ($3,500 wasted due to overwhelm) |
| With Readless Same subscriptions + Readless Pro ($59/year) | $5,059 | 90% utilized | $4,500 value (+$3,000 unlocked value) |
Net Gain: $3,000/year in unlocked subscription value Plus additional benefits: 325 hours/year saved (90 min daily → 12 min), better strategic decisions from actually consuming all sources, cross-source intelligence you'd miss reading individually, zero subscription guilt | |||
Real Executive Example
Subscriptions:
- • The Information: $399/year
- • The Information Pro: $999/year
- • Stratechery: $150/year
- • Not Boring: $100/year
- • CB Insights: $2,000/year
- • StrictlyVC: $300/year
- • 10 other premium sources: ~$2,000/year
Total: $5,948/year
Before Readless:
Reading 30% due to overwhelm = $1,784 effective value, $4,164 wasted
With Readless ($59/year):
Reading 90% = $5,353 effective value
Net gain: $3,569/year in unlocked value + 325 hours saved
Enterprise-Grade Security for The Information and Premium Content
End-to-End Encryption
All emails encrypted in transit (TLS 1.3) and at rest (AES-256). Your $399/year Information subscription content and other premium newsletters are private and secure. Only you can access your paywalled content.
Zero Third-Party Sharing
We never share your Information newsletters or other premium content with third parties, AI training companies, or data brokers. Used exclusively for your personal digest generation.
SOC 2 Type 2 (In Progress)
Enterprise-grade security compliance audit underway. Already compliant with GDPR for EU users and CCPA for California residents. Data residency controls available.
Original Content Accessible
Full original newsletters (The Information, Stratechery, etc.) remain in your Readless inbox. Click through anytime to read complete articles, verify facts for citations, or deep-dive on specific scoops.
Why Security Matters for Premium Subscriptions
You're paying $5,000+/year for exclusive intelligence. The Information's scoops on upcoming IPOs, funding rounds, or strategic shifts could move markets if leaked early. Our security infrastructure ensures your premium content stays confidential.
- No AI training on your data (unlike free email services)
- Information paywalls remain intact (we don't republish premium content)
- Summaries are for your eyes only—not shared or indexed
What Tech Professionals Say About Newsletter Overload
"The relentless overload that's wearing us down is generated by a belief that 'good' work requires increasing busyness—faster responses to email and chats, more meetings, more tasks, more hours."
— Cal Newport, Author of Deep Work
This is exactly why consolidating premium newsletters like The Information with AI-powered tools like Readless matters. You maintain strategic intelligence without the overwhelm.
Industry Statistics (2025-2026)
77%
of media leaders say subscriptions are "important or very important" for 2025 (Reuters Institute survey of 326 media leaders in 51 countries)
$45M
Substack's current annualized revenue (2025), driven by premium subscriptions. The tech professional newsletter market is booming.
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Frequently Asked Questions About The Information
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