Pitch for the check you want

Welcome to Startups Weekly, a nuanced take on this week’s startup news and trends by Senior Reporter and Equity co-host Natasha Mascarenhas. To get this in your inbox, subscribe here.

Tech’s guiding principles these days aren’t too difficult to find: discipline, focus and cash conservation. But I’ve always found those same focuses to be especially in conflict with what it means to be an early-stage founder pitching your vision: You have to have Elon Musk-level ambition, big dreams and the ability to sell a company to investors before there are any real metrics behind it.

In some ways, it’s the job of the investor to see the reason to say yes anyway. In other ways, the downturn is very much making early-stage founders professionalize sooner and sooner; philosophically looking more like the late-stage company pitching for its Series C than the buzzy pre-seed.

I’ve been noticing small things about how early-stage founders have changed their pitches, suggesting that the checks are currently less about the messiah and more about the monetization.

Read the rest of my column on TC+: “Founders change their pitch.”

In the rest of this newsletter we’re talking about AI attribution, venture layoffs and modern entrepreneurship. As always, you can follow me on Twitter or Instagram to continue the conversation. If you feel like supporting me extra, subscribe to my very free Substack.

We’re actually starting to see AI be a factor in tech layoffs

Layoffs are almost a daily occurrence during this news cycle — I covered Chief and Clubhouse layoffs within an hour of each other — but the reasons behind each reduction often lack specificity. Dropbox surprised me. CEO Drew Houston, who laid off 16% of staff this week, cited “the AI era of computing” in relation to the layoffs. “We’ve believed for many years that AI will give us new superpowers and completely transform knowledge work. And we’ve been building toward this future for a long time, as this year’s product pipeline will demonstrate,” he said.

Here’s what to know: I expect there to be more redundancies in workforces that are partially attributed to artificial intelligence. It’s not a new take: The concern I hear most often around AI is its ability, or intent, to replace everyone’s jobs. To break from that pattern is to land lots of snaps: Harvey AI, backed by Sequoia this week, is the buzz all over tech dinners for its pitch to supercharge lawyers.

dropbox glitch

Image Credits: TechCrunch

Venture’s down

TC’s Mary Ann Azevedo broke news this week: “Fintech-focused VC firm Anthemis Group lays off 28% of staff as part of restructuring.” She reports, “Anthemis declined to provide further specifics around its strategy moving forward, instead pointing me to this blog post from co-founder Amy Nauiokas. In the post, Nauiokas writes that the firm aims to “translate 2022’s reckoning in private markets into enduring change in the structure and method of early-stage investing.”

Here’s what to know: We don’t see venture layoffs often, even though I have a feeling many are ghosts these days. Reductions will continue — and maybe more loudly this time. Last June, Backstage Capital fired most of its staff, with now only two people remaining at the venture firm.

A modern take on an entrepreneur

On Equity this week, I interviewed Ocho’s Ankur Nagpal, the founder of the business owner-focused fintech, as well as Teachable and Vibe Capital. We spoke about everything from the temperature of solo GPs and how building in public has impacted his trajectory.

Here’s an excerpt we got within minutes of recording: “A great CEO … you have to be mildly sociopathic. And there’s a lot of stuff that I just like struggled with when it came to being CEO, because it would be against my values as a person,” Nagpal said.

Bright multi colored balls randomly arranged on pink strings blue background, used in post about Betterdata

Image Credits: Getty Images

Etc., etc.

A weird parallel: Instacart’s co-founder and former CEO Apoorva Mehta raised $30 million for his new healthcare startup, WSJ reported last year. That news makes it all the more interesting that Instacart’s current CEO, Fidji Simo, co-founded a healthcare clinic, according to Fortune. According to TechCrunch, what a weird parallel between a grocery delivery startup’s past and present leadership! Jokes aside, maybe it’s a nod to what Amazon tried to do with Whole Foods and One Medical, Instacart edition.
Big apologies: to those who I missed in Boston last week. I was ready to jump on stage but then food poisoning — from a coffee shop that shall remain unnamed — got the best of me. I heard it was a hoot, though, so check out TC+ recap posts coming at you soon.
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Of course: It’s already Disrupt season. Reminder that there’s a ticket for every budget and role.
And finally, I have a shameless plug: Scoops make me! If you hear about a venture firm or startup winning, raising, flailing, or, oh I don’t know, booting an executive because of internal happenings, tell me. I love seeing early pitch decks and term sheets too. Happy to talk about anonymity and explain more of my process and what I’m looking for. You can tell me stuff on Signal at +1 925 271 0912. No pitches, please.