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Startups
Practical takes on B2B sales, fractional CRO leadership and go-to-market, from 20-plus years carrying the number on five continents.
If Your Company Might Only Last Six Months, Your Sales Math Changes
A CTech opinion argues your next business might last six months, and that can be enough. If that is the bet, sell for fast payback, not distant lifetime value.
40 Companies, One Category, 20 of Them Israeli. How Do You Sell?
Nikesh Arora counts 40 firms racing to secure AI agents, at least 20 Israeli. When the category is a knife fight, the deck does not win. The sales motion does.
Debt Does Not Kill Companies. Soft Revenue Plus Debt Does.
Analysts warn that debt could amplify the damage AI does to businesses. The real risk is debt stacked on revenue that was never durable. Fix the revenue first.
The Sales Metrics Founders Should Actually Track
Founders drown in dashboards. Here are the five sales metrics that predict revenue, the vanity numbers to ignore, and when each one should make you act.
Enterprise Sales for Startups: Selling to Companies 100x Your Size
Selling to giants means committees, procurement, and long cycles. Land a champion, multi-thread the account, de-risk the buy, and never single-thread.
$4.6B in Revenue. An $8B Loss. A Possible $2 Trillion Valuation.
Anthropic makes $4.6B, loses $8B+ operating, and could be worth $2 trillion. Three numbers that shouldn't fit together, and in 2026 somehow do.
OpenWeb Raised $390M and Hit a $1.5B Valuation. Now It's Seeking Insolvency Protection.
OpenWeb raised $390M at a $1.5B valuation and now seeks insolvency protection. The lesson for founders: fix the revenue machine while you still have runway.
How to Forecast Revenue When You Have No Sales History
No sales history? A top-down wish is not a forecast. Here is how to build a bottoms-up revenue model from activity and conversion assumptions you can defend.
How to Build a B2B Sales Process From Scratch
A CRM with random stages is not a sales process. How to build a real B2B sales process from scratch, with buyer-based stages and a forecast you can trust.
Why Your Startup Can't Sell (And It's Not the Product)
Most founders blame the product when sales stall. The real problem is almost always the motion around it. Here is how to tell, and what to fix first.
When to Hire Your First Salesperson (Founders Wait Too Long, Then Panic)
Revenue milestones do not tell you when to hire your first salesperson. A repeatable motion you can hand off does. Here is what ready actually looks like.
From $4.8 Billion to $60 Million. A Great Product Cannot Save a Broken Business Model.
Nano-X had revolutionary imaging technology and still lost 99 percent of its value. The cause was a business model that cash could not support.
A Startup Raised $20 Million. It Just Sold for $150,000.
Swish.ai had Coca-Cola, Nestlé and CyberArk as customers and still sold for the price of a used car. Logos are not revenue, and it never built a sales engine.
20 Sales Problems EVERYONE has - 1 Platform with 20 solutions.
Most B2B founders are not bad at selling. They are selling without a system.
Costco loses money on gas on purpose. Here is the strategy.
THAT is the entire strategy. Across 747 stations, Costco makes a few cents per gallon. Regular gas stations make 25 to 35 cents. Lines wrap around their.
Wix added $150M in revenue, then fired 1,000 people to afford it.
This week it is firing 1,000 people to afford it. Revenue up 14% to $541 million. A $34 million profit last year turned into a $57 million loss. Cash flow down.
I tracked 300 founders from my old sales calls. A quarter are already gone.
I went through 300 old sales calls and a quarter of the companies are gone. Most had good products. They left sales and go-to-market for later.
Most Companies Can't Afford a REALLY Good VP Sales
A really good VP Sales costs $250K to $350K a year before the team around them. Many startups take on that overhead too early, when a fractional model fits.
Why does this bus cost 15x more in Boston than in Beijing? It is not quality.
A bus costs about $80,000 in Beijing and up to $1.2 million in Boston. The gap is system tax, and most sales organizations are paying it too.
The quickest way to become a millionaire? Start as a billionaire.
Ilan Ben-Dov built a $5.1 billion empire on debt and watched it wash away. The lesson for founders is that growth built without trust is a sandcastle.