$100B software debt crunch is looming as PE-backed loans come due

Opportunities in the PE debt crunch, where your Gemini traffic went, and AI API prices down 80%? Well, sort of.

Newsletter //

Issue 2, November 3, 2026

Featured story

About $100B of PE-backed software loans come due in 2028 and 2029

SaaStr bar chart of risky loans owed by PE-backed companies: an average of $60B due two years out in 2023 to 2025, against $140B due in 2028 and $160B due in 2029, with software about a third of each year

On October 27, the Wall Street Journal reported that about $300B of risky loans owed by private-equity-backed companies come due in 2028 and 2029, five times the recent two-year average. On SaaStr the next day, Jason Lemkin noted that about a third, roughly $100B, is owed by software companies, many bought with seven-year loans in 2021, and that Thoma Bravo has already handed Medallia to its lenders.

Our thoughts

It's no secret that companies in this type of spot struggle. They tend to cut R&D, raise prices, and eventually, if things can't be overcome, they begin to lose their strongest engineers and salespeople.

At a time in software where I'd argue that adapting matters as much as a moat, or more, these companies will have an additional challenge as their ability to adapt becomes limited.

So, I'd agree with Lemkin's advice: take some time to list out and consider the customers and top talent of your competitors bought by PE firms around 2021.

There may be opportunities there in the near future.

It's no secret that companies in this type of spot struggle. They tend to cut R&D, raise prices, and eventually, if things can't be overcome, they begin to lose their strongest engineers and salespeople.

At a time in software where I'd argue that adapting matters as much as a moat, or more, these companies will have an additional challenge as their ability to adapt becomes limited.

So, I'd agree with Lemkin's advice: take some time to list out and consider the customers and top talent of your competitors bought by PE firms around 2021.

There may be opportunities there in the near future.

– Chris Heysel, CEO

More this week

Gemini stopped tagging the links it cites

Bar chart of daily visits tagged utm_source=gemini in one consultant's server logs, rising from near zero in early September to 83 on September 28, then falling to 3 the next day and staying near zero through October

SEO consultant Natzir Turrado reported on October 27 that Gemini had stopped adding a utm_source=gemini tag to links it cites. In his server logs, tagged visits vanished overnight on September 29 and hadn't returned a month later.

Our thoughts

Gemini's tags look gone for good, so expect more AI visits to show up as Direct in GA4. This means continue the basics of asking prospects how they found you and, if it was via AI, what they were asking when you were recommended.

Gemini's tags look gone for good, so expect more AI visits to show up as Direct in GA4. This means continue the basics of asking prospects how they found you and, if it was via AI, what they were asking when you were recommended.

– Chris Heysel, CEO

a16z raised about as much as 650 other US venture funds combined

SaaStr bar chart splitting the $108.5B raised by US venture funds through Q3 2026: $60.9B to other funds of $500M or more, $23.8B to Andreessen Horowitz, and $23.8B to about 650 other funds

SaaStr's Jason Lemkin showed on October 26 that a16z closed $23.8B of the $108.5B that US venture funds raised through September, as much as about 650 smaller funds combined. Over the same months, an estimated record 8,625 US startups raised a first round.

Our thoughts

This isn't necessarily a new trend or surprising. I include this more as a point of something we're watching: what is the rate of consolidation, is it increasing, and if so, why?

PitchBook notes that LPs short on cash are re-upping with the firms that paid them back, which makes sense.

What I wonder is how are funds using the additional capital to build unfair advantages that increase the likelihood of their next fund's success?

Brand is an obvious advantage for them, but their build-out of platform teams is another area we're watching. It'll be interesting to see where this goes.

This isn't necessarily a new trend or surprising. I include this more as a point of something we're watching: what is the rate of consolidation, is it increasing, and if so, why?

PitchBook notes that LPs short on cash are re-upping with the firms that paid them back, which makes sense.

What I wonder is how are funds using the additional capital to build unfair advantages that increase the likelihood of their next fund's success?

Brand is an obvious advantage for them, but their build-out of platform teams is another area we're watching. It'll be interesting to see where this goes.

– Chris Heysel, CEO

About half of B2B software buyers lean on AI at most steps of picking a vendor

Bain bar chart: 54% of B2B software buyers use generative AI most of the time or almost always to research vendors, 51% to compare shortlisted vendors, 46% to build the first list of vendors, and 32% to negotiate pricing

Bain's July survey of 207 IT decision makers found 54% use AI at least half the time to research vendors, 51% to compare a shortlist, 46% to build the first list, and 32% to negotiate. About one in five almost always use it for the first three.

Our thoughts

Bain is republishing some additional graphics from their July study.

What shocked me was the percentage of buyers that are not only using AI for initial research, but throughout the buying process. Seems increasingly important to understand how AI is perceiving you.

I suggest growth teams use any of the many open-source projects to track this. Ours is Overheard AI.

Bain is republishing some additional graphics from their July study.

What shocked me was the percentage of buyers that are not only using AI for initial research, but throughout the buying process. Seems increasingly important to understand how AI is perceiving you.

I suggest growth teams use any of the many open-source projects to track this. Ours is Overheard AI.

– Chris Heysel, CEO

OpenAI and Anthropic cut their model prices by up to 80% in a few months

Vercel line chart of its AI gateway from April to September 2026, indexed to April at 100: usage rose to 790.8, spend to 342.7, and price per token fell to 43.3

Data scientist Max Woolf tallied the cuts on October 25, including 80% off OpenAI's small Luna model in July and 40% to 60% off the cost of using Anthropic's newest Opus. He argues cheap open-weight models could keep prices falling.

Our thoughts

It's good to see open models putting pressure on the frontier labs.

The very important nuance here, though, that people forget, is that AI companies often show prices as cost per token. But different models, and even different model generations, can have significantly different amounts of tokens required per task.

Be sure to review your cost per task, and also to run your own tests, and consider what models you need for what aspects of which tasks to balance performance and price.

It's good to see open models putting pressure on the frontier labs.

The very important nuance here, though, that people forget, is that AI companies often show prices as cost per token. But different models, and even different model generations, can have significantly different amounts of tokens required per task.

Be sure to review your cost per task, and also to run your own tests, and consider what models you need for what aspects of which tasks to balance performance and price.

– Chris Heysel, CEO

The Office Buzz

Personal recommendations and thoughts from the team.

MindTime, a meditation timer

MindTime's banner: the app's ring logo and the words "MindTime, Your daily meditation timer" over a misty lake

Even 5 minutes of meditation a day is so helpful for me personally.

Most apps are freemium and keep pestering you with ads and upgrades, which inside a meditation app is completely counter to what you want. MindTime doesn't bug me. Its maker, Christian Krueger in Berlin, says technology should "help you do something meaningful, then get out of the way," and I think it shows.

No affiliation, I just use it and like it. Get it for iPhone or Android.

– Chris Heysel, CEO

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Developed for ourselves, now live for everyone.

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Last Week in GTM

Get the latest on AI and GTM.
Developed for ourselves, now live for everyone.

Email address

We’ll respect your inbox. Because we don’t like spam either.