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Mindshare >> Data >> Tech ⚔️
How Wispr Flow became everyone's go-to AI voice app, their Netflix-style pricing, using monetization as a litmus test, and why they build their own…
Sep 4
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Astha from Chargebee
4
August 2025
Take the experimental budget 🧪💰
Docket's co-founder Arjun Pillai on: raising before the vertical wave hits, the m word: margins, three layers of /evals they rely on, and more.
Aug 21
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Astha from Chargebee
2
Introducing: PMF /evals ◎✨ + the wedge in AI support with RunLLM
A new newsletter /evaluating how AI-native products find PMF. Ft. Vikram Sreekanti, co-founder of RunLLM in edition #1.
Aug 7
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Astha from Chargebee
7
May 2024
Why Mailchimp never raised 📖
Ben Chestnut's reflections, framing the enteprise AI hammer, and B2B reels.
May 23, 2024
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Astha from Chargebee
3
“Don’t start a tech-enabled service” 👩💻
The service/SaaS tightrope, why PMs made up for a uniquely difficult persona, and the beautiful utility of constraints.
May 9, 2024
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Astha from Chargebee
4
April 2024
CEO -> CTO -> IC 🪃
Scratching a passionate itch, catching the PMF lightning twice, and an unlikely B2B brand bet.
Apr 25, 2024
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Astha from Chargebee
4
The all-in-one niche 🍞
Really knowing the problem space, why Photoshop/Powerpoint stuck, and raising from a position of strength.
Apr 11, 2024
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Astha from Chargebee
4
March 2024
The transitional segment 🔄
Why startups shouldn’t start with mid-market customers, deftly allaying platform risks, and observations from building an email platform.
Mar 28, 2024
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Astha from Chargebee
5
Avoiding enterprise “funny money” 🔮
The virtues of subjective-but-informed-decisions, hard truths of founder-led sales, and where to start with enterprise deals.
Mar 14, 2024
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Astha from Chargebee
4
February 2024
Who should own pricing? 💸
Deciding whether pricing strategy stays with product/GTM, the costs of pursuing foundational models, and positioning towards JTBDs not personas.
Feb 14, 2024
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Astha from Chargebee
5
January 2024
Predicting SaaS waves 🌊
The criticality of market timing, why PMF is gradual and should be measured as such, and The (SaaS) Office.
Jan 17, 2024
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Astha from Chargebee
9
Crazy, energy-draining 2021 🫠
Beyond growth frenzy, a top-down, all-hands AI excursion, and an org-building lesson on expectations and modelling.
Jan 3, 2024
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Astha from Chargebee
4
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