Rare token hunter. VP growth @labelbox past: Co-founder @upcraftai, CMO @BookCameo, @remoteyear founder
San Francisco, CA
Joined January 2011
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Greg Caplan retweeted
Manu (@manuaero) joined Jason Calacanis on This Week in AI alongside @sarahookr (Adaption Labs) and @spirosx (Resolve AI) to break down the rapidly shifting AI landscape.
From the Token Price Wars and Demis Hassabis’ recent call for an AI oversight board, to the Uber vs. Waymo robotaxi battle, and a reality check on whether orbital data centers are science fiction or closer than we think (Manu’s aerospace engineering background came in handy) 🚀
A few key insights from Manu:
- Proprietary intelligence is the new edge: As base model costs decline, the real winners will be defined by what they own: proprietary data, customized RL environments, deep domain expertise, and continuous feedback loops.
- From models to moats: The narrative is shifting. The biggest opportunity is not building another general frontier model, but architecting intelligence systems around an enterprise’s unique workflows and expertise.
- Owning the enterprise intelligence stack: General purpose AI will continue to raise the baseline for everyday productivity, but true industry differentiation, whether in banking, pharmaceuticals, or manufacturing and beyond, will come from owning the proprietary knowledge layer that compounds over time.
Greg Caplan retweeted
It’s been awesome watching Greg build out Upcraft from day 1. Congratulations!!
Thrilled to announce that @labelbox is acquiring Upcraft! 🚀
After 5 incredible years building agents that automate smart human-like engagement, this is the perfect next chapter for the whole team.
We're pumped because Labelbox is leading the way in data-centric AI and powering the datasets that train the world's best models. Bringing our agent tech to Alignerr means we'll make expert recruitment, onboarding, matching, and support way faster and smarter.
With billions pouring into post-training and reinforcement learning right now, expert-generated data is the biggest bottleneck for giving models real human taste and judgment. This move directly tackles that.
Huge thanks to our investors for believing in us from the start. @ilyaf and the team at @kleinerperkins, your guidance and support built the team that made this possible. To all our backers, thank you for turning our vision into reality. Grateful for the journey and excited this brings some upside your way.
Long term, this feels massive. AI's future depends on combining human expertise with agent-driven scale. As models get insanely capable, compute isn't the limit anymore. It's high-quality, expert-curated data that adds nuance, judgment, and taste. By agentifying marketplaces like Alignerr, we unlock a flywheel: pull in more experts, generate richer data, build better models. It's not just about one acquisition. It's accelerating the path to truly reliable, human-aligned AI. Can't wait to build it with the Labelbox crew!
Greg Caplan retweeted
Mamoon and Ilya are great, if you are considering working with them, I highly recommend it: fortune.com/2026/01/31/insid…
Greg Caplan retweeted
It always feels like @gdcaplan is playing 5 years in the future. He and I first connected when he was CEO @remoteyear. He’s since gone on to run marketing @BookCameo and is now building AI sales agents at @upcraftai. So fun to talk growth marketing with him on his RevUp podcast.
Greg Caplan retweeted
Omg Senator Fetterman bought a George Santos cameo for Bob Menendez.
I thought my ethically-challenged colleague @BobMenendezNJ could use some encouragement given his substantial legal problems.
So, I approached a seasoned expert on the matter to give ‘Bobby from Jersey’ some advice.
Greg Caplan retweeted
Starting a thread for my normal friends who don't experience my feed.
You've been completely scammed about "open air prisons" + concentration camps
See below for what life was like in Gaza, starting with a luxury car dealership that opened Aug 2023 in Gaza City (h/t @imshin)
👇
Greg Caplan retweeted
I’m excited to (finally) announce the launch of my newest incubated venture: @TurpentineMedia, a network of podcasts, newsletters, and more covering tech, business, and culture, from the perspective of industry insiders and experts.
Think The Ringer or Barstool, for tech.
We (@ASalyers3 @NatalieToren) believe that the world’s most interesting, important, and useful ideas and experiences come from those with skin in the game, sharing their expertise and passion – now matter how niche the topic.
We are excited to build a tech media company, by tech people, that is decisively pro-tech and that exists to helps people improve at their jobs.
More broadly, I believe building an independent media company is a great wedge into other products as well as a great asset for my investing at @villageglobal
More on what we’re building, why now/why us, our lineup of upcoming shows and hosts, open roles, etc below.
But the tl;dr is: we’re looking for new shows, hosts, and sponsors. If you think you might be the next Lenny Rachitsky, All In, Acquired, or [xyz show] for your niche – or you want your company to reach a particular niche audience – DM us or get in touch on our website @TurpentineMedia.
Greg Caplan retweeted
So uh started looking into Trady.com from our FASTest CEO Domm...so far 80% of the businesses I've contacted from the site don't seem to be real (shell companies set up with fake yelp and google listings), 90% of them don't pick up the phone, 1 said trady made their landing page without their permission, and 2 so far seem to actually be using their product but said Trady sponsored them.
Greg Caplan retweeted
Is eating at a restaurant really eating? Is sleeping at a hotel really sleeping? Is shopping online really shopping? Whole essay written by someone who thinks we work the same as we did building physical widgets. Couldn't even cite productivity decline, just old man hand-waving..
Greg Caplan retweeted
I’ve spent my life wandering cities and countries. Most people think it’s rather unusual…But now studies suggest that wandering actually makes you happy 😍 Well, here’s to more travel, roaming the earth and happiness in 2023! wsj.com/articles/the-emotion…
Greg Caplan retweeted
I would guess 1 in 10 small service businesses allow for online quote requests and online payment.
Using a software like Jobber is the best way to get a competitive advantage that I can think of.
Lowest hanging fruit out there to make good money.
Would be in top 5% instantly.
Greg Caplan retweeted
remote work has become the "dog ate my homework" excuse for institutional and corporate failure.
Greg Caplan retweeted
If you are out of ideas, go for a walk.
This paper found walking (whether outdoors or a treadmill) increased key types of creative thinking for over 80% of undergraduates. The reasons are not fully clear, but there seem to be direct effects on the brain. apa.org/pubs/journals/releas…
Greg Caplan retweeted
“Above all, do not lose your desire to walk: Every day I walk myself into a state of well-being and walk away from every illness; I have walked myself into my best thoughts, and I know of no thought so burdensome that one cannot walk away from it.” — Søren Kierkegaard
Greg Caplan retweeted
i should work from my phone more, i wish it were easier. i‘ve broken free from the office, the next step is untethering from my desk.
in 10 years it might seem crazy that we had to sit stationary at a desk for 8 hours a day
Greg Caplan retweeted
Biggest permanent change due to the pandemic is remote work:
Office occupancy still down by more than 50% (!) and the return to office trend is starting to plateau
