Hey, thanks for joining for another week of New Venture Weekly.
I’m a sucker for a good newsletter (don’t look so surprised).
But newsletters are a very crowded space now.
So how do new newsletters stand out?
One idea I keep coming back to is Challenge Newsletters.
Challenge newsletters are email-based programs that guide subscribers through a series of structured daily (or weekly) prompts designed to help them build a habit, learn a skill, or ship creative work.
They usually last 10, 30, or 100 days. Think of them as a mix between a course and a habit tracker - delivered entirely through email.
Let’s jump in!
🤷 Why?
Why It’s a Good Business:
No-code, low-overhead: You can build one with an email platform and a landing page.
High perceived value: People pay to be held accountable and make progress.
Community potential: Built-in network effects if you add sharing or social proof.
Lead-gen or paid product: Use it to grow your email list or sell it as a digital product.
Nicheable: You can create these for any skill (design, writing, coding, fitness, journaling, etc).
Setup Once, Run Forever: You can set up the challenges once and run them on an automation forever.
⭐️ Examples:
Daily UI – Free 100-day design prompt newsletter for UI/UX portfolios, monetized via upsells and sponsors. Here’s the founder talking about how he makes $30k/m.
Ship 30 for 30 – Paid 30-day writing challenge with daily essays, community access, and digital writing templates.
#100DaysOfCode – Open-source 100-day coding challenge, often repackaged into email prompts and monetized with course upsells.
Write of Passage Sprint – Free 5-day writing habit challenge used as a lead magnet for a $4,000 writing course.
Gumroad 14-Day Challenge – Email challenge that helps creators launch products in 2 weeks, drives usage of Gumroad.
Build Once by Visualize Value – Premium 30-day product-building challenge focused on systems and execution.
Freelance Bold Pitching Challenge – 5-day email challenge helping freelancers pitch clients, leads into coaching offers.
30 Days of Obsidian – Free challenge teaching Obsidian workflows, acts as a funnel into a premium course.
Some of these newsletters make millions a year through these free lead-magnets alone.
🧐 Opportunities:
As I mentioned, this is an idea I’ve wanted to try for a while, so here are some of my ideas that you can try:
30 Days to Launch Your First Digital Product – For indie makers and solopreneurs.
100 Days of AI – Daily projects using AI tools like GPT, Midjourney, etc.
30 Days of Reels – For creators trying to grow via short-form content.
14-Day Email List Kickstart – Build and grow your first 100 subscribers.
21 Days to Master Notion – Daily Notion builds, templates, and systems.
30 Days of Financial Reboot – Budgeting, investing, saving - one task per day.
10-Day Startup Validation Sprint – Validate your idea fast with daily market tests.
30 Days of Cold Outreach – For freelancers and agencies booking clients.
7-Day Podcast Launch Challenge – From concept to first published episode.
30 Days of Webflow/Framer Builds – For aspiring Webflow/Framer devs and designers.
30 Days of Lovable - For devs wanting to ship fast and learn AI coding.
100 Days of Drawing – For artists building a habit and portfolio.
21-Day Morning Routine Reset – Wellness + productivity audience.
30 Days of YouTube – Create a full month of videos, one per day.
7-Day Shopify Store – Daily steps to go from zero to first customer.
14 Days to Better Sleep – For wellness brands or sleep coaches.
30 Days of Freelance Systems – Set up automations, contracts, onboarding, etc.
30 Days of Prompt Engineering – For devs or marketers mastering AI prompts.
21 Days to Your First Info Product – E-books, templates, mini-courses.
30-Day Voice Training Challenge – For vocal coaches and YouTubers.
10 Days to Better UX – Bite-sized UX audits and design principles.
30 Days of Fitness Branding – For personal trainers building an online brand.
21 Days of Apps – For builders wanting to ship quick MVPs.
30 Days of Songwriting – For musicians looking to build a daily habit.
🛠 How to Build:
Step 1: Pick a Niche That Compounds
Criteria:
Daily output is shareable (writing, design, code, content)
Audience hangs out online + subscribes to email newsletters
There's a skill gap + real desire for transformation
Obvious upsell on the backend (course, product, tool)
Step 2: Build It on Beehiiv
Once you have your idea, get set up on a tool like Beehiiv (the tool I use for this newsletter - affiliate link but you get a 30-day trial + 20% OFF for 3 months).
Step 3: Monetize It on the Backend
Sell a premium upgrade
$39–$99 “Fast Track” version with:
PDF + bonus templates
Notion board
Bonus “pre-challenge” video
Email swipe files or toolkits
Add a 1:1 or cohort upsell
Weekly group calls
Slack/Discord access
Personal feedback / coaching add-on
Affiliate offers
If your challenge uses tools (e.g. Beehiiv, Notion, Webflow, Jasper, etc.)
Plug affiliate links throughout + day 0/start email
Turn challenge participants into long-term subscribers of a paid newsletter or community
Pitch a full course / productized service at the end
Create “spin-off” challenges as separate products or lead magnets
License the format to brands or creators
🚀 How to Grow:
Package the challenge as a free (or $5) digital product.
Launch it on Product Hunt - Hit that “build-in-public / productivity” audience. Also go for PH alternatives.
Wall of progress – Showcase user completions publicly for social proof.
Twitter threads – Share journey/results with a link to challenge.
Referral program – Use SparkLoop or manual rewards to incentivize sharing.
Cross-promos – Partner with aligned newsletters for swaps or shoutouts.
Paid ads – Drive traffic to free challenge, monetize via upsells.
Blog posts – Publish Medium/LinkedIn articles with a challenge CTA.
Optional community – Create a Discord/Slack to boost retention.
Cohort-based urgency – Limited-time signups to create FOMO.
Guest creator editions – Collaborate with influencers for reach.
YouTube Shorts/TikTok – Share daily challenge tasks as video snippets.
Productized version for companies - Turn your challenge into a white-labeled product for coaching businesses, SaaS tools, or creator brands.
Post success breakdowns on Indie Hackers / Hacker News - “I launched a 14-day challenge and 1,500 people joined in 3 weeks — here’s what worked.”
Create a leaderboard or badge system - Even if it’s just a Google Sheet or image badge — gamifies the experience and fuels sharing.
🤯 Sponsors
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🔥 Cool Stuff
(Bookmark these)
Find problems that need business solutions - Access the Problems & Pain Points Database.
Want to grow your business? Here’s a database of tools that can help.
Want to promote your startup for free? Here’s a database of free places to promote your startup.
Want to turn your idea into a business? Check out this business idea checklist.
Want to differentiate from your competitors? Check out this Differentiation Strategy Guide
Want to run ads for your business? Use these proven psychological ad positioning strategies.
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