SaaStr AI London is Dec 1-2!! See You There!!

Helping, founding, funding, and growing B2B start-ups.  Making it a positive-sum game for everyone involved.  VC checks $500k-$4m @ SaaStrFund.com.  2x founder with nine figures of founder exits.

"Do or do not. There is no try."

Specialties: helping people grow and become their best.  Doing not the impossible, but the unlikely.  Never giving up.

Join 10,000 of us IRL at SaastrAnnual.com May 12-14 in SF Bay!!

FREE Weekly Workshops and Live AMAs, Sign up here -> https://www.saastr.com/workshop-wednesday/

SaaStrFund.com investments include:

- Co-led Series A in Salesloft ($2.3B exit)
- Co-led Seed in Pipedrive ($1.5B exit)
- Led Seed in Algolia ($2.3B)
- First VC in Talkdesk ($10B)
- Led Seed in Gorgias ($800m)
- Led Seed in Owner.com ($1B)
- First Investor in RevenueCat ($500m)
- First VC in Logikcull ($280m exit)
- Proud smaller investor in Greenhouse ($800m exit), Sqreen ($400m exit), Automile ($1B SEK exit), Opus Pro, Higgsfield.ai, and many others!
- and much more

Jason M. Lemkin

So far I've watched 3 VC seed deals this year where the founders just decided to keep the money for themselves and not build the product.

All were on SAFEs, and they took the position they owed investors nothing and that in fact they were not even investors. Just SAFE holders.

One eventually returned cash after keeping a large chunk for themselves.

Another hired an attorney who said plainly nothing was owed to the investors and the founders could pay themselves whatever they wanted.

I did not personally invest in these deals but I might have, they had a lot going for them (or so it seemed).

This is going to happen in the Age of AI. It's the flip side of so many things also exploding so quickly and growing at insane rates.

It's just a risk to be more aware of perhaps than in the past.

SaaStr AI Annual ’26 is May 12-14 in SF Bay!! See You There!!

Engineering: sell what we have

Sales: build what I can sell

This, is The Enterprise

You can't scale if you can't recruit 

First, learn to love it

Then, learn to staff it

So I’ve been vibe coding for about 4 months and shipped 10 apps and now I’m doing something I didn’t want to do.  I’m starting to build our own vibe’d marketing automations (on top of Resend).

If there’s one thing I don’t think you should do yourself, it’s marketing automation.  Building lists, segmenting lists, sending millions of emails … this is something you don’t want to get wrong.  Or wing it.  Buy a tool that does this all day long.  

But … but … we’ve reached the limits from our existing vendors, too.

I want to use AI to hyper personalize emails in many of the same ways we do for our AI SDRs.  Not exactly the same (that would be time and cost prohibitive), but to some extent.

And our existing horizontal tools just can’t do this.

So I vibe’d a series of new campaigns to SaaStr AI this week.  We’re sending 5 different campaigns ourselves now, outside our marketing automation tools.  Soon it will be more. 

I didn’t want to.  But we needed to.

I am proud to continue my journey in Edtech with my new stealth start-up. Nothing inspires me more than working to understand how students learn, and to apply the science of learning to edtech.  For those who share my passion, I look forward to many more years together in the corridors and classrooms, virtually and in person. I love making new Edtech friends and learning about what motivates you to transform education. 

Formerly the Founder and Chief Creative Officer of Mrs Wordsmith. the award-winning literacy company for K-8 (Reception to Y8), I hope to bring my experience and learnings to bear in an exciting new capacity. Mrs Wordsmith was a dear part of my journey. I am proud to have designed, developed, edited, co-authored and worked with educators and academics globally to develop over 20 books, games, apps and white papers on the science of reading for Mrs Wordsmith.  During my tenure, we sold over 500,000 copies of books and games which are curriculum compliant in both the United States and the United Kingdom. I am grateful to have gone on this journey with many of you, and to have learned so much about what motivates students and how they learn.

Sofia Fenichell

Today, I am grateful for the launch of College CoPilot! Full demo video below! 

If you're a family, school, or guidance counselor helping kids achieve higher scores on the SAT® and conquer the college admissions process, here's one of the most helpful use cases for AI — focused 100% on the student.

I’m going through the process for the second time with my youngest right now. So I know how overwhelming it is. 

We built AI tools that feel genuinely magical:

An AI SAT® tutor that explains nuanced grammar rules (semicolon or colon and why), highlights the operative word in reading comprehension to unlock inference questions, and breaks down complex math. College CoPilot teaches in context — 24/7.

The first AI-powered deep research tools built specifically for college, helping students actually research the universities they're about to invest years of their lives in.

An essay coach that doesn't write for you, but helps you bring out your own voice.

A planner that finally keeps tests, drafts, deadlines, and chaos in one place.

Under the hood, we spent months on the hard part: context engineering. Making the tutor concise, accurate, and genuinely supportive. Building research tools that surface real insight rather than noise. Designing an essay workflow that helps kids stay authentic.

And we were lucky to build this with people who helped shape the SAT®, ACT® and selective admissions systems themselves.

College CoPilot is for families, tutors, and schools who want AI tools worthy of the stakes.

The best part? Every account comes with 3 free CoPilot seats for parents, tutors, and guidance counselors. It takes a village to get a kid into college these days. And we wanted to spread the joy, and keep the costs down for families.

Admission Accomplished.

Please share if you know families,  schools, tutor agencies and counselors looking for the world’s smartest SAT test prep and college admissions support. 

Jim Larimore Paul Weeks Donna Matovinovic Patrick Derham Edward Smallwood  

https://lnkd.in/eFjYT2g8

Founder & CEO Study Hall.AI | Every student deserves a team of personalised learning agents by their side 24/7. Google for Startups AI Accelerator | EdSafe AI Transparency Committee

Open video: StudyHall AI - College CoPilot on youtube.com

We are in an era of content hypersupply. Here’s what this means. 

The value of content is going down. Most of what's produced will never be consumed. Billions—probably trillions—of AI infographics and generated videos will never be seen by a human eye.

This isn't new. Human history is littered with exuberant waste:

- 2–3 million new books released worldwide each year, millions selling only a handful of copies
- 1+ billion YouTube videos with under 100 views
- 2.5 billion tons of food lost or wasted annually

Now add AI slop to the pile. Multiply by whatever number you want. 

The educational and economic value of most AI-generated content is probably worth less than the cost to produce it. 

So what comes next?

Not more generation. Not faster models. Better curation. Intentional interfaces. AI that filters signal from noise instead of adding to the noise.

The next wave won't be about producing more. It'll be about making less—and making it matter.

We've created the McDonald's Happy Meal of infographics. Abundant and average. But what I think of the quality isn’t what matters. 

These AI-generated infographics are good because they give more people the pride of authorship. They give more people a voice through a CoPilot. That's engagement.

Right now, everyone's focused on teachers using AI to produce more content. But that just reinforces sage-on-the-stage. Better-equipped lecturers are still lecturers. Yes, upskill teachers. But that's not the transformation.

The transformation is students creating and consuming their own content simply because they made it. The creator is the one who learns. The creator is the one who actually engages.

AI makes this possible at scale: every student gets a thought partner. They write, argue, revise, build. The teacher becomes facilitator, not performer.

Can an AI chatbot inspire kids to love reading and talk about books? I’ve had so much fun this week developing our Book Talk tool for primary and secondary with Emily Hobson and Miss Kiran S.  at Oasis. 

Edtech is always better when you work with educators in the classroom who are research-based to build inspiring AI tools that combine print and digital literacy. 

Thanks gals. You reminded me why I love doing what I do so much. Can’t wait to unveil it with you in January!

#lovereading #oralliteracy #ailiteracy #

Here are the three most honest AI head fakes of 2025.

1. Higher ed is dead. Everyone I’ve met who says this is secretly helping their kids get into college - from VCs who invest in job-destroying AI to AI Literacy bloggers who believe curriculum isn’t aligned with job growth.  

2. Teachers are using AI to shave hours off their day. All the teachers I know who use AI are love laborers. They are obsessed with learning about AI and actually investing extra hours in their day becoming AI craftsmen. 

3.  Kids don’t know how to use AI tools.


Do you agree? Any you want to add? 

Sof

My weekend AI-in-education reflection...
We’re shifting from what I call the Lost Credibility Era of education and Edtech into something more complex: the No Trust Era of education and AI.

It feels like a frontier moment. Everyone is racing toward the next horizon, pushed by competitors and pulled by hype, hoping the gold rush is real. Frenemies are everywhere, some imagined, some real.

There’s no going back to the old era. But crossing this wilderness demands TRUST: trust from learners, educators, institutions, and the public.

TRUST is hard — invisible until it’s broken, painstaking to rebuild, and essential to everything that comes next. 

I’m optimistic. But only if we choose to build trust as intentionally as we build  technology. This means we need to be human, caring and humble in our approach to innovation. We will make mistakes along the way. We have to correct them at speed and own them. 

We cannot blame Big Tech, Edtech, teachers, parents, kids, lack of capital or anything really. This is a moment for problem-solvers and critical thinkers who can be TRUSTED.  

Sof

P.S. These are my own words, not the words of AI. I am the former Mrs Wordsmith afterall! So you can have TRUST. 😁

I just asked our AI-powered College Research tool 
"Can a Polar bear get into Harvard?"

Love ❤️ the our AI responses....
Criteria: Academic Record

Typical Applicant: High GPA, challenging courses

Polar Bear Applicant: Demonstrated expertise in Arctic survival,  marine biology (potentially)

Criteria: Extracurriculars

Typical Applicant:  Leadership roles, community service

Polar Bear Applicant: Leading a pod, exceptional hunting/survival skills,  contributions to Arctic ecosystem

And then we had a nice chat about the food issues of the Harvard dining hall, such as how the lack of wild seals poses ethical and practical challenges. 

A little #SATtestprep procrastination with College Research is always a good thing! Plus it I can't think of a better way to practice AI Literacy! 

Happy Saturday!

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