Build Lightning‑In‑a‑Bottle Solutions, Not Nice‑to‑Have Features
It's perhaps surprising, but if I had one piece of advice for a B2B entrepreneur getting started, it wouldn't be about culture, execution or product nuances. My advice would be to make sure what you're working on is something customers badly want. The legendary Frank Slootman uses the idiom "lightning in a bottle." Clients only switch technologies or try something new if it's radically better. If your pitch is "[incumbent] is too expensive" or "our UI is better," you often don't have the lightning yet. "Nice to have" technologies show up as: * "How can we prove the ROI?" * "We'll get back to you in a few weeks" * "How are you better than [incumbent vendor]?" " "We're swamped now but will get back to you" * "It's just a matter of time - we'll get there eventually" Sometimes these customers end up buying. But those long sales cycles can feel like torture unless they are paired with very high price points and a lot of capital. The reason I was motivated to write this is that the situation is even more confusing for an entrepreneur (or VC) right now. Customers are in a unique situation where their bosses and boards are saying "you have to buy AI technology." So they start looking for "RL for [domain]" or "agents for [domain]." Yet, often they don't even have a use case that's defined. The founder gets the wrong signal, thinking they have a "must have" product. But when the budget tide eventually rolls out, customers will cull AI spending to fewer vendors and some of the "nice to have" AI startups could be drowning in churn. I've seen hundreds of founders go through this process (pre- and post-transformer). What sucks the most is that they waste years of their lives on ideas that the market doesn't badly need - and often end up with little financial reward at the end. The best founders I know keep searching and iterating until they find a product-market where customers are banging on their doors to get it.
SaaS Isn't Dead—Legacy Software Still Generates Cash
There's a meme going around that SaaS is Over! It's good clickbait for sure. But the extremes are both wrong. SaaS isn't over. Nor is it the same as it was. The past tech transitions tell the tale - mainframe...
Repeat Customer Feedback Loops For
How do you actually learn from your customers in B2B? I get asked a lot about my biggest learnings from my last company (Gainsight). It's hard to not feel cliched. Culture! Focus! Strategy! But there's a thing I did 1000+ times that...
Adopt Multi‑product Strategy Early to Avoid Growth Wall
The #1 thing I wish I had done sooner at Gainsight: multi-product to avoid the "growth wall." Every market flattens out eventually. For some (e.g., search advertising), it takes a long time. But for most, it happens sooner than you think....
Public Markets Value SaaS at 2‑6× Revenue
This post from @rohitdotmittal says the quiet part out loud. Ultimately the public markets are the arbiters of value. So many great SaaS cos trade between 2x and 6x revenue. Important for founders to know this.
Custom AI Needed Until Generalization Boosts Corporate Efficiency
Let's talk AGI and GDP - and a question I have... I have no idea when AGI is coming or even what the precise definition is. But there's one thing I have strong priors around: large companies have incredibly bespoke processes -...
Target the Goldilocks Zone: Mid‑Maturity Enterprise AI Customers
Just spoke to a friend who founded an early-stage AI startup (yes, this was an actual conversation - not one of those LinkedIn “I was just chatting with…” cold opens 😭). We were talking about a real dilemma: enterprise buyers...
Vibe Coding May Intensify Pricing and GTM Pressure
@jasonlk Agreed. Do you think tho that the threat of vibe coding plus ability for more competitors to emerge will create more pricing and gtm pressure?
Hire Only When Role Is Clearly Defined, Avoid Obligatory Hiring
This post on hiring [link in comments] by Gaurav Vohra (H/T Gokul Rajaram ) caught my eye. The title can be misread, but the underlying point hits on something I’ve seen in tech companies—big and small—for years. I’ve made this...
Old Lessons Still Matter in AI-Driven Future
Not everything we’ve done in our careers is relevant for the future. But some of it absolutely is. As I think about what I do next (spoiler: I truly have no idea yet), I’ve been reflecting on the distance between...
Craft Client Meals Guests Actually Look Forward To
How do you run client meals that people actually look forward to? I've led hundreds of customer lunches and dinners over the years. As Erica Mansfield Robin Merritt Emily Wilkes Kat Leong Lauren Olerich know well, I have a very...
AI Founders Now Prioritize Real-World Use Cases over Models
Quick takeaways from yesterdays excellent CVAI conference: 1. So many inspiring entrepreneurs presented 2. Agentic pricing is still in the wild west 3. Same with agentic UX 4. Fascinating to see founders talking more about the underlying application use cases versus just the models...
Grant Lee's Unconventional, Actionable Startup Advice
Epic startup advice from @thisisgrantlee of @GammaApp - super practical and non-consensus
AI Turns SaaS Margins Into Growth Opportunity
Some are saying “AI killed SaaS.” Maybe the truth is closer to (paraphrasing Bezos): “SaaS’ margins are AI’s opportunity.” And the opportunity may be to embrace the new business model of lower margins and larger markets. Let me explain. Software companies...
AI Makes Software Forever Modern, Ending Legacy Drag
People talk a lot about AI enabling "personalized" software. An equally exciting thing for me is allowing software that's always modern. As software businesses age, there is often little incentive for vendors to continuously make their products "modern." As such, customers...
Automated AI Customer Service Hits Uncanny Valley
When all is said and done, pre-generative AI "automated" customer service will be the ultimate "uncanny valley."