Why Holding Companies Beat SaaS for Enterprise AI
Michael Lee and Sequence joined the Dell Family Office to take Baldwin private in a $7.7 billion deal, proving permanent capital can out-execute standard private equity and venture models.
10+ hours of podcasts, in 5 minutes.
How software subscriptions are changing, and which SaaS companies are exposed. 25 write-ups from 11 shows so far, the newest from September 2026.
AI agents are pushing software vendors toward direct database access and outcome-based pricing. Custom AI coding tools and slower growth have slashed legacy valuations. Incumbents integrating AI into established workflows continue to see strong demand.
Incumbents maintain strong growth by adding AI to established workflows. Salesforce, Atlassian, and Twilio saw stock jumps of 20% or more after monetizing new agent features for existing customers.
Falling growth rates cause steep private market corrections. Airtable and Miro suffered value drops of nearly 90% from peak valuations. Miro saw the valuation multiple compress from 30x to under 3x annual recurring revenue.
Autonomous software coworkers threaten the standard per-seat billing structure. Vendors capture the larger outsourced human services budget by selling finished outcomes.
Matt Bank revealed that GEM flipped its software budget within twelve months, moving from 90% third-party tools to 90% in-house software development.
From Why Allocators Are Replacing Commercial SaaS With In-House Code, Capital Allocators · Sep 20
Enterprises spend roughly $6 on outsourced human services for every $1 they spend on software tools.
From Why the Next Trillion-Dollar Software Firm Sells Outcomes, 20VC with Harry Stebbings · Aug 30
A multi-year drop to 5% annual growth compressed Miro's valuation multiple to under 3x ARR, down from near 30x at its peak.
From Miro's 89% Crash: What Happens When SaaS Growth Stops, TBPN · Sep 13
Across 7 shows, there was broad agreement on two critical trends: AI agents are fundamentally reshaping software value, shifting it from traditional user interfaces to headless, API-first architectures. Concurrently, a severe and escalating compute and power crisis, driven by infrastructure limitations, rising costs, and increasing public opposition to new data center construction, threatens AI's growth.
Where they split: A key tension emerged around the necessity versus the environmental and social costs of expanding AI infrastructure. Some argued for the critical need to build more data centers to maintain global AI leadership, while others highlighted the immense energy consumption and local burden of these facilities, fueling public and political opposition.
Across 2 shows, commentators agreed that Airtable's sale at roughly 1.28 billion dollars down from an 11 billion dollar peak highlights a brutal valuation correction for horizontal SaaS businesses facing slowing venture growth and AI substitution.
Where they split: All-In framed the collapse as a product vulnerability caused by AI tools replacing traditional no-code platforms, while 20VC emphasized financial mechanics and the lack of private equity buyer competition for legacy SaaS assets.
Michael Lee and Sequence joined the Dell Family Office to take Baldwin private in a $7.7 billion deal, proving permanent capital can out-execute standard private equity and venture models.
Matt Bank revealed that GEM flipped its software budget within twelve months, moving from 90% third-party tools to 90% in-house software development.
Bending Spoons acquired digital whiteboard maker Miro for $1.79 billion, an 89% collapse from its peak private valuation of $17.5 billion.
Orion Advisor Solutions' diligence team claimed HiddenLevers owed $600,000 in uncollected state sales taxes following shifting state tax rules for SaaS companies.
Salesforce shares surged over 20% after raising guidance and integrating its data layer directly with Anthropic's Claude.
Enterprises spend roughly $6 on outsourced human services for every $1 they spend on software tools.
AI agents aren't killing SaaS; they're revitalizing it by interacting with existing software tools. Claire Vo admitted a "trough of despair" about SaaS, only to find agents excel at "pressing buttons" within applications.
Autonomous agents are shifting enterprise software from human copilots to a coworker model, directly threatening per-seat pricing models.
Referrals need to be a product feature: Don't treat referral programs as an afterthought. Integrate them deeply, make rewards easy to discover, and align them directly with product usage limits.
Valuation Cliffs are Real: Airtable's collapse from an $11.7 billion valuation to $1.28 billion (a 90% drop) shows that even profitable, growing SaaS companies are not immune to brutal market corrections, especially when chasing…
AirTable, once valued at $11 billion, sold for $1.285 billion despite doing $485 million in ARR and growing 20% year-on-year. This 88% valuation cut signals a harsh market correction for horizontal SaaS apps.
The average unicorn now stays private for over 12 years in the US, a direct result of abundant private capital and secondary markets offering employee liquidity without a public IPO.
10+ hours of podcasts, distilled into one 5-minute read. Free, every Sunday morning.
One email a week. Unsubscribe with one click.