Mar 7, 2025 · 20m · saastr
Why I’m Scared to Buy New SaaS Apps Now with SaaStr CEO and Founder Jason Lemkin
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
SaaStr founder Jason Lemkin details nine reasons why buying B2B software has become an intimidating, high-friction ordeal due to predatory billing, aggressive lock-in, and coercive sales practices. Contrasting legacy SaaS tactics with user-friendly generative AI tools, he urges software leaders to mystery-shop their own products and remove anti-customer barriers.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 99.9% of the talking time here. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 5:25 No guest combativeness (solo monologue)
This is a solo presentation episode by Jason Lemkin without an active guest exchange; minimal brief diarized utterances represent non-combative background bleed.
Hardest push from Jason ▶ 7:20 No host pushback (solo monologue)Because this is a solo commentary format, there is no guest to receive or offer conversational pushback.
Biggest teaching moment ▶ 10:12 No schooling moments (solo monologue)There is no guest present to correct or educate the host in this solo episode.
Jason holds their own ▶ 18:10 No host hit-back dynamic (solo monologue)The host speaks uninterrupted to the audience throughout the episode rather than debating or hitting back against an interlocutor.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| The Death of Fair Billing and the Rise of Vendor Consolidation | 0 | 0 | 0 | 0 | This segment is a solo monologue by Jason Lemkin discussing vendor consolidation and the erosion of early SaaS fair billing policies. | |
| Reason 1: The Nightmare of Canceling or Downgrading Subscriptions | 0 | 0 | 0 | 0 | Monologue presentation by Lemkin sharing personal anecdotes about predatory cancellation processes and hidden downgrade links, with only minor diarized audio bleed. | |
| Reason 2: Forced Upgrades, Seat Expansion, and Arbitrary Fees | 0 | 0 | 0 | 0 | Solo presentation covering forced seat expansions, arbitrary logo branding fees, and aggressive auto-renewal legal threats. | |
| Reason 4: Unpredictable Variable Costs and Usage Surprises | 0 | 0 | 0 | 0 | Monologue addressing hidden variable costs in consumption-based pricing and the necessity of free trials in the AI era. | |
| Reason 6: Customer Success Teams Evolving into Aggressive Sales Reps | 0 | 0 | 0 | 0 | Solo rant detailing the degeneration of customer success into aggressive quota-carrying upsell channels. | |
| Reason 8: Disrespecting Buyer Time and Mandating Sales Calls | 0 | 0 | 0 | 0 | Monologue analyzing SDR tactics that mandate phone calls and disrespect prospective buyers' time. | |
| Reason 9: Data Lock-In and Export Headaches | 0 | 0 | 0 | 0 | Solo concluding segment examining data lock-in and urging founders to secretly purchase their own software to audit friction. |
Statements from this episode (14)
Lemkin: Harder Offboarding Makes Purchasing Software Far More Stressful
“And the harder it is to leave, man, the more stressful it is to buy.”
Lemkin: Slack and Zoom Avoided Price Hikes for Years Early On
“Slack and zoom never raised prices for years. Slack was disruptive in the early days because it implemented what it called the fair billing policy. And if you didn't use seats, they didn't charge you for them.”
Lemkin: Average SaaS Vendor Counts Are Down While Spend Is Up
“Zylo, which It's one of the vendors that helps you manage SAS costs and vendors reported that the average number of SAS vendors is down. It's down. And that's, I think there's a number of reasons, but it's not because spend is down. According to Gartner, spend…”
Lemkin: SaaS companies play cancellation games when growth slows
“Why aren't you? It's because you're not growing fast enough when you're playing games.”
Zoom Demanded SaaStr Upgrade to 40 Seats and Prepay Four Years
“Twice they sent us bills out of the blue telling us we had to upgrade to 40 seats and prepay four years annually.”
Lemkin: Zoom is growing at 4% annually on $4 billion revenue
“Zoom's under pressure. They're growing four percent a year at four billion.”
Lemkin: SaaStr Immediately Submits Cancellation Notices When Buying Software
“You know, a couple of years ago, we instituted a policy at little tiny Saster that as soon as we buy an app at Saster, we have to immediately send a termination notice and people made fun of me four or five years ago, but now this has become a common practice.…”
Lemkin: A $100B+ Public SaaS Company Threatens Customers With Lawsuits
“Even worse, a number of public SaaS companies you probably know threatened to sue users or threatened legal action. One of them is well over a hundred billion dollars in market cap has repeatedly. You can see it on X. If you search sent messages threatening to…”
Lemkin: Marketing vendor quoted SaaStr over $100K for 500K records
“One vendor that's several thousand dollars a year for a marketing tool wanted over a 100,000 dollars a year to support our records of 500,000.”
Lemkin: AI represents the rebirth of freemium and free trial models
“AI is also the rebirth of freemium, rebirth of free trial. We expect to try this stuff. For free and you've got to work around the cost.”
Lemkin: Lacking a free trial signals a product is too hard to use
“But if you don't have a free version for me to at least try a little bit, just says your product's too hard to use.”
Lemkin: Most SaaS customer success teams have degenerated into aggressive upsell reps
“Most of the vendors we work with customer success has turned into upsells and account managements, and they're just there to get us to buy more stuff.”
Lemkin: Hesitant to Buy New SaaS Apps Without Clear Exit
“And seriously, I am for the first time in many years in SAS, I am scared to buy new apps now, unless it's clear I can leave.”
Lemkin: SaaS Startups Should Not Add Sales Friction Before Massive Scale
“I'm going to argue until you're at mass scale, until you're at the Salesforce scale, don't add any friction to the sales process. There is an argument when you're at hundreds of millions of revenue to add friction. There is an argument that friction itself is …”