The $25M Jenni AI founder story

Hey, it's Guy & Farzan,

Three nights out last weekend. The kind where Monday morning feels like a negotiation with your body. Worth it though. Back to business. Today's founder stories won't write themselves. Let's go.

Reading time: 8.25 mins

In the mail today. 3 founder stories, 2 founder notes

 Founder story 1 

From his parent's basement to $25M valuation while battling cancer."

That's what David Park achieved with Jenni AI. But this "overnight success" was 10 years in the making.

Here's the wild story:
→ Started at age 16 with a failed clothing brand
→ Dropped out of college to chase the startup dream
→ Cold-called from his childhood bedroom for years
→ Built company to $8M annual revenue
→ Now valued at $25M

But the fascinating part isn't just the numbers - it's how the vision evolved:
- 2016: "I want to be a founder and build stuff"
- 2020: "AI can revolutionize how people write"
- 2021: "Let's make AI writing accessible to students and professionals"
- 2023: "We're building the future of AI-assisted content creation"
- 2024: "Anyone can create high-quality content with AI"

The journey wasn't smooth:
- Multiple failed business ideas before finding Jenny
- Months at $2,000 MRR with no growth
- Had to borrow money from mom just to afford Chipotle
- Missed $250K investment due to romantic distraction
- Diagnosed with cancer while company was thriving

Then everything changed. An investor who backed Uber heard David on a small podcast and reached out with $100,000.

Today's results:
- $8M annual revenue
- $25M valuation
- Thousands of users worldwide
- Viral growth through social media
- Self-sustaining team and operations

Key insight about the future of AI writing: We're moving from manual content creation to AI-assisted creation - just like how word processors replaced typewriters.

The biggest opportunities now?
→ Understanding what users truly need
→ Building based on deep customer feedback
→ Using viral marketing and social media strategically

Real example:
David shifted from selling harder to listening harder - asking users "What do you dislike? How does this fit your workflow?" That changed everything.

Why this matters:
The bottleneck in AI startups is shifting from "Can you build the technology?" to "Can you understand your users deeply enough?"

User feedback and persistence are becoming more valuable than technical brilliance alone.

This is why David believes that entrepreneurs must be prepared to give their all, understanding that even with tireless effort, success is never guaranteed.

The future isn't just about building AI tools, it's about understanding human needs deeply enough to build the right AI tools.

Founder story 2

From broke single Dad to $6.5M: The flea market reseller story

Rick, 41, went from being a broke single dad in 2008 to generating $6.5M annually reselling pre-owned clothing. Started by flipping a broken phone on eBay for quick profit, bought for $35, sold for $70 same day. That lightbulb moment led to 20 years of relentless hustle.

His evolution:
- From electronics to eBay's #1 men's clothing seller ($2.5M/year, 100K items sold)
- Now B2B wholesale model (current $6.5M revenue).

Wakes before 6am to hit flea markets while others sleep, sourcing designer pieces like Burberry, Hermès, and Patagonia for pennies on the dollar.

Key insight:
Success came from tenacity and showing up every single day for nearly 20 years—he's never taken a day off. His wholesale model now serves resellers who order 1,000+ pieces weekly.

His philosophy:
"When you unlock the power to multiply money... how can you rest?" The drive stems from watching his grandfather die two weeks after retiring—teaching him to keep moving, keep going, never stop.

Founder story 3

Simo Lemhandez: From McKinsey Consultant to 7 figure CRM revolutionary with folk

The Journey
- Grew up in Morocco in a family of entrepreneurs
- Completed intensive Classe préparatoire and was accepted to both HEC and Polytechnique
- Worked at Morgan Stanley (investment banking) and McKinsey (consulting)
- Attended Le Wagon tech bootcamp to learn coding
- Met Thibaud Elziere (founder of Fotolia, sold to Adobe) randomly after DMing him on Twitter
- Founded folk in 2021
- Built company to 3,500 clients and seven-figure ARR
- Raised $9 million in SAFE funding from Accel and 100 angel investors including founders of Webflow, Dropbox, and Behance

The Evolution of Vision
- 2019-2020: "I need a better way to manage my freelance client relationships than Notion"
- 2021: "Let's reinvent CRM and go after the king of SaaS: Salesforce"
- 2022-2023: "Build a CRM that's easy-to-use like Notion but integrated with your entire world"
- 2024: "Create an all-in-one platform that's proactive with AI"
- 2025: "Build a future where AI assistants handle sales work, letting people focus on human connection"

Overcoming Obstacles
- Left stable, prestigious jobs at Morgan Stanley and McKinsey to start from scratch
- Spent 18 months building the product before full launch
- Faced the challenge of entering a mature, crowded market dominated by giants
- Had to set an extremely high bar to compete with established players
- Discovered that even though people hate their current CRMs, changing is difficult
- Balanced building product features while simultaneously mastering distribution

Today's Impact
- Seven figures in annual recurring revenue (ARR)
- 3,500 company clients
- 18 employees
- 150,000 website visitors per month
- $9 million in funding from top-tier investors
- Strong presence across Product Hunt, Chrome Store, and G2 reviews

Growth Strategies That Worked
- Early Hype Building: Created homepage before product existed, generated 10,000 waitlist signups
- Launch Repeatedly: "Every opportunity is a good one to launch. The worst thing isn't to be ridiculed, but to go unnoticed"
- Scientific Testing: Systematically tested acquisition channels using effort, cost, conversion, and average basket metrics
- Multi-Channel Approach: SEO, Google/Meta/Reddit/LinkedIn ads, affiliate program, influencer partnerships
- Product-Led Growth: Engineered the product for natural sharing and collaboration
- White-Glove Onboarding: Personal onboarding for early users to collect qualitative feedback
- Affiliate Program: Following HubSpot's model where 50% of new revenue comes from partners
- Free Trial Over Freemium: High-engagement trial period instead of freemium model

Key Milestones
- Met Thibaud Elziere after hearing him on a podcast and DMing him on Twitter
- Built initial homepage and collected 10,000 waitlist signups
- Spent 18 months developing the product while gradually giving access to waitlist cohorts
- Launched on Product Hunt after seeing strong retention and engagement metrics
- Built team to 18 employees
- Reached seven-figure ARR with 3,500 company clients
- Secured $9 million in funding from Accel and angel investors

The Philosophy

"The best growth hack is word of mouth. It's free and scales infinitely. And the only way to engineer word of mouth is to build a great product."

"Successful people are macro-optimist, micro-pessimist."

"People: Choose your cofounder wisely. Choose your team wisely. Money: Don't run out of cash. Treat money as if it were your own. Market: Fall in love with a problem, not your product. Distribution: Think about distribution as much as you think about the product. It shouldn't be an afterthought. Energy: It's hard. It's a grueling marathon. And it never gets easier. Enjoy the ride: I can't think of anything more fun to do professionally."

"Mature categories are hard. Even though people hate their CRM, the bar is super high, and there is a lot to build. It's harder than we expected."

The Vision for the Future
In 24 months, Simo envisions a fundamentally different way of selling:
- CRMs will capture ALL data automatically from every channel—communication platforms, social media, websites, meetings, calls, and videoconferences
- Hyperspecialized AI assistants will work on behalf of salespeople: research assistants to study companies, scoring assistants to prioritize leads, email assistants to identify follow-ups, meeting assistants to provide daily briefings
- Salespeople will focus on the human part of their job—connecting with people—while context-aware assistants handle the rest
- The role of sales will shift from manual data entry and research to authentic human relationship building

folk's Competitive Edge
What makes folk different in a crowded CRM market:
- Easy-to-use, set up, and customize like Notion with a flexible data model
- Integrated with LinkedIn, emails, calendar, and WhatsApp
- Automatic data enrichment using seven different providers combined
- All-in-one platform combining email sequences, lead picking, and enrichment
- Proactive AI that updates contact fields automatically, follows up on your behalf, and drafts emails
- Built for a market where existing players have very low Net Promoter Scores and are perceived as slow, manual, and cumbersome

 Founder note from Joseph Lee founder of Supademo  

I celebrated my birthday this weekend. These are the 20 biggest lessons I’ve learned over the past year. 👇🏽

1. Life becomes 10X more fun when you prioritise experiences over things.

2. You are the sum of the people you are around. If there is negativity, remove it quickly.

3. You can be a great mum + build something epic. But you will need a village to do it.

4. Be obsessed with protecting your time. It is by far your most powerful asset.

5. Do not let the internet tell how hard you should or shouldn’t work. Only you decide that.

6. You are not responsible for your kids happiness, let them experience disappointment.

7. There will always be another goal to chase. Make sure you stop and smell the roses.

8. Kids don’t need you there all the time. They need the time you are there to be uninterrupted.

9. If you are evolving quickly some people will leave your life. Get comfortable with that.

10. Marriage is about seasons. Sometimes it’s your time to shine and sometimes it’s theirs.

11. Success is more about what you say no to than what you say yes to. Ruthlessly prioritise.

12. The people who say ‘everyone has the same 24 hours in a day’ are liars.

13. Failure is just part of the process, get comfortable with it.

14. Being afraid is an asset. Use it to drive you forward.

15. Self doubt will try to stop you. Be proactive about fighting it.

16. Don’t speak negatively about yourself. Not even as a joke.

17. There is no such thing as balance. Only priorities.

18. As a leader your principle job is to chase the urgency.

19. Having a great idea is a fallacy. Execution is everything.

20. Your parents are getting older. Tell them you love them more.

 A founder note we loved

That’s all for this week. See you in 7 days.

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Cheers

Guy + Farzan
Founderoo