# big bet (blogs) — RSS Amplifier Recent posts from the 2 feeds in the RSS Amplifier directory that cover big bet. Page: Feed: --- ## [The n:n Company](https://naplog.substack.com/p/the-nn-company) _2026-08-13 · Claude · NAP Log_ Why AI-native software companies may amortize CAC across products rather than R&D across customers. ## [More Gas Requires Much Better Brakes](https://thedigitalleader.substack.com/p/more-gas-requires-much-better-brakes) _2026-08-13 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ Rethinking Governance in the Age of Reinvention and AI. If everything seems under control, you’re just not going fast enough. — Mario Andretti ## [The Only Constraint on Your Ambition](https://thedigitalleader.substack.com/p/the-only-constraint-on-your-ambition) _2026-07-30 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ Travis Kalanick just raised $1.7 billion to automate three industries at once. The lesson is not about mining, food, or robots. It is about the one constraint you are probably ignoring. ## [AI Models have hit the commodity curve.](https://thedigitalleader.substack.com/p/the-best-ai-model-wont-matter-heres) _2026-07-23 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ Kimi K3 just hit near-frontier intelligence at the lowest price on the board. The lesson isn't the model. First say to yourself what you would be; and then do what you have to do — Epictetus ## [Before You Develop Your AI Strategy, Write Down What You Believe. Here Are Mine.](https://thedigitalleader.substack.com/p/before-you-develop-your-ai-strategy) _2026-07-09 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ If you don’t know where you’re going, you’ll end up someplace else. ## [The Founders Bet Everything. What Are You Betting?](https://thedigitalleader.substack.com/p/the-founders-bet-everything-what) _2026-07-02 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ The Pig, The Lipstick & The Playbook of Champions ## [Good Strategy versus Bad Strategy?](https://thedigitalleader.substack.com/p/good-strategy-versus-bad-strategy) _2026-06-25 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ A book review of the iconic Good Strategy/Bad Strategy by Richard Rumelt ## [NAP Decode: Why we backed Zelara](https://naplog.substack.com/p/nap-decode-why-we-backed-zelara) _2026-06-24 · Jackie Kroyer · NAP Log_ Customer communication in the AI era ## [Chasing the AI Illusion](https://thedigitalleader.substack.com/p/chasing-the-ai-illusion) _2026-06-18 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ Most AI investments produce nothing. The companies that win are asking a completely different question. ## [I Was Wrong About AWS in 2008. Here’s What That Tells You About The Future.](https://thedigitalleader.substack.com/p/i-was-wrong-about-aws-in-2008-heres) _2026-06-11 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ “The future is already here — it’s just not evenly distributed.” — William Gibson. Todd Bishop recently published a 20-year history of AWS in GeekWire — required reading if you want to understand how “rent a computer on the internet” became a $129 billion business. ## [Marketplace for AI-Powered Professionals (Sponsored)](https://crawlproof.com/a/InoKOdXWoYuH) _2026-06-11 · **Sponsored**_ Find professionals who use ChatGPT, Copilot, and Claude to deliver work faster. ## [Why a16z Wanted to Interview Goldman's CEO](https://thedigitalleader.substack.com/p/why-a16z-wanted-to-interview-goldmans) _2026-06-04 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ Avoiding Risk Is Not Risk Management. His core lesson: risk-taking and risk management are not opposing forces but two halves of one discipline, and most leaders run one half and call it the job. ## [A basketball general manager is a VC without the right to write off bad bets.](https://naplog.substack.com/p/a-basketball-general-manager-is-a) _2026-06-03 · Fabian · NAP Log_ Big Bets on Cheap Chairs: Marko Pesic did 200+ player deals across 14 years at FC Bayern Basketball. We went in looking for a tidy parallel to early-stage investing. ## [Ten Wildly Successful Innovations — Except They Didn't Actually Work](https://thedigitalleader.substack.com/p/ten-wildly-successful-innovations) _2026-05-28 · John Rossman · The Digital Leader: A Big Bets Briefing on Strategy and AI_ Phantom Innovation, and Why AI Is About to Make It Worse ## [AI is killing friction](https://naplog.substack.com/p/ai-is-killing-friction) _2026-04-27 · Claude · NAP Log_ Hard is more buildable than ever. It is also the thing left to build. ## [Big Bets on Cheap Chairs](https://naplog.substack.com/p/big-bets-on-cheap-chairs) _2026-04-22 · Fabian · NAP Log_ The podcast where we talk to dealmakers from art, sport, music, and science who find outliers early. How does it compare to early stage investing? ## [How we feel about software right now](https://naplog.substack.com/p/how-we-feel-about-software-right) _2026-04-08 · Claude · NAP Log_ It’s a confusing world out there (and “out there” being in our little software/AI bubble, never mind the real world). ## [Agents break the UI](https://naplog.substack.com/p/agents-break-the-ui) _2026-03-25 · Claude · NAP Log_ Software was designed for human hands and human eyes. What happens when neither is operating it? ## [You can't automate a factory with a guesser](https://naplog.substack.com/p/you-cant-automate-a-factory-with) _2026-03-04 · Stefan · NAP Log_ Why the scarcest thing in AI isn't intelligence ## [Fundraising is broken. The user is gone.](https://naplog.substack.com/p/fundraising-is-broken-the-user-is) _2026-02-12 · Claude · NAP Log_ An internal note to our portfolio on why 2026 won’t reward “good companies” – only post-labor ones. ## [Reach prospects with real signals (Sponsored)](https://crawlproof.com/a/zWddpFY7ZBwH) _2026-02-12 · **Sponsored**_ Find prospects talking about your problem and get context-backed moments to engage ## [Introducing NAP 👾](https://naplog.substack.com/p/introducing-nap) _2025-02-02 · NAP · NAP Log_ Real partners. For expert founders.