Jonathan Kestenbaum

Entrepreneur, Investor & Board Member - focused on WorkTech

[Jonathan Kestenbaum @JKestenbaum]

https://t.co/1NyZUAkNGg

[Jonathan Kestenbaum @JKestenbaum]

Just as we built the assembly line around machines that augmented physical labor during the Industrial Revolution, we are now building the assembly line around machines that augment knowledge work. The challenge is no longer how to move materials through a factory, but how to move information, decisions, and expertise through an organization. AI isn’t simply another tool it’s the machinery around which the next generation of work will be organized.

[Jonathan Kestenbaum @JKestenbaum]

@AndrewYang AI doesn’t eliminate work. It reallocates labor. The real policy challenge is not job creation; it’s workforce transition. How do we help a customer service representative become an HVAC technician, a healthcare coordinator, a skilled operator, or an AI-enabled salesperson?

[Jonathan Kestenbaum @JKestenbaum]

@RoundtableSpace On top of being Nuked which is absolutely true, it says “you must be getting tired, it’s late, maybe we should pick up tomorrow” every couple prompts. It’s 10 am dude…

[Jonathan Kestenbaum @JKestenbaum]

@sweatystartup AI isn’t the bubble.
Bad implementation is.

[Jonathan Kestenbaum @JKestenbaum]

Everyone's debating whether AI is hitting a scaling wall.

Wrong wall.

https://t.co/ZvEZJqoSnv

[Jonathan Kestenbaum @JKestenbaum]

https://t.co/1NyZUAkNGg

[Jonathan Kestenbaum @JKestenbaum]

@BernieSanders https://t.co/lvPNUPZqri

[Jonathan Kestenbaum @JKestenbaum]

AGI is replacing people. But it pays nothing back.
It’s time we tax AGI like we tax humans.
Here’s how—and why it matters.
👉 https://t.co/BK7CMcTwYM

[Jonathan Kestenbaum @JKestenbaum]

@sweatystartup Happy for Marshall. Having done a lot of staffing and WorkTech M&A, I’d love to see the GP math behind a $52M valuation. That’s a big bet unless the contract GP is exceptionally real and durable.

[Jonathan Kestenbaum @JKestenbaum]

@JesseTinsley I agree — if you buy them at the right price. AI will compress traditional SaaS margins, so if you can acquire these companies at services-level multiples and then bring in AI, you’re in the money.

[Jonathan Kestenbaum @JKestenbaum]

@Wisdom_HQ 116

[Jonathan Kestenbaum @JKestenbaum]

AI didn’t take your job in 2025.
It took your tasks.
2026 is the year it comes for your org chart.

We spent the last year talking about AI adoption like it was installing a CRM.
Cute.

The truth? You don’t get efficiency until you restructure the workforce around AI and almost nobody has done that yet.

Meanwhile:

- Programmatic advertising stopped being “spray and pray” and became “pay only for quality.”
- SaaS as we know it is dying.
- Identity fraud is exploding, and blockchain is finally (yes, finally) ready for its grown-up table.

And the next big KPI?
Not candidate experience.
Hiring manager experience.

2026 is going to be messy.
Not because the tech isn’t ready but because the organizations aren’t.

Read more here: https://t.co/lSepi4MJI9

[Jonathan Kestenbaum @JKestenbaum]

@unseen1_unseen AI

[Jonathan Kestenbaum @JKestenbaum]

@adamscrabble Great video!

[Jonathan Kestenbaum @JKestenbaum]

@MarioNawfal @PeterDiamandis Here are my thoughts: https://t.co/BK7CMcTwYM

[Jonathan Kestenbaum @JKestenbaum]

@AndrewYang Here is my take: https://t.co/FYmjvbdGfE

[Jonathan Kestenbaum @JKestenbaum]

AGI is replacing people. But it pays nothing back.
It’s time we tax AGI like we tax humans.
Here’s how—and why it matters.
👉 https://t.co/BK7CMcTwYM

[Jonathan Kestenbaum @JKestenbaum]

@rand_longevity Check out @MonarchTractor

[Jonathan Kestenbaum @JKestenbaum]

@CherryTruthy @JoshBobrowsky @adcock_brett I agree that there are bad actors on both sides for sure

[Jonathan Kestenbaum @JKestenbaum]

@vottofanaccount @JoshBobrowsky @adcock_brett It’s about having open transparent conversations. If someone who worked for me got an offer I couldn’t compete with I would be happy for them & support it. However if it’s all about $$ all the time I would want to know that at the beginning so we could set expectations both ways

[Jonathan Kestenbaum @JKestenbaum]

@CherryTruthy @JoshBobrowsky @adcock_brett Actually yes, that is exactly what is offered.