Money decisions
Your logo wall is a liability
Marquee logos landed at a third off, renewed flat, and never wrote the promised case studies. The logos cost more than they ever returned.
Archive
Founder decisions
The first time you lied to the board
It was a small thing. A number rounded up. A risk you didn't quite mention. You told yourself it was framing. The next quarter you had to maintain the frame.
Operations
Your SOC 2 Will Take Twice as Long
February: the auditor quotes six months. September: the deal needs the report. The letter lands the following February, and the deal closed elsewhere.
Team reality
8 Engineers, Zero Ships, Six Months
Thirteen people, two roadmap reviews, nothing shipped to a customer in two quarters. How teams go busy and idle at once.
Growth traps
804 registrants, zero net customers
Eight hundred registrants. Three hundred attendees. One signup. The webinar was content marketing wearing a sales costume.
Money decisions
The 409A valuation you didn't update
The last 409A was eighteen months old, and options had been granted against it. The IRS calls that compensation income.
Founder decisions
Name your successor before the bus does
If you vanished for six months, who runs the company? Most founders can't answer, and the cost is daily, not disaster.
Operations
The bug backlog nobody decides on
Reported in February, deprioritized in April, still open in November. The bug had outlasted three roadmap cycles.
Team reality
Your one-on-one is a status meeting in disguise
Thirty minutes a week for eighteen months, opening with the Q3 rollout. The manager had built a standing meeting that wasn't management.
Growth traps
Stop optimizing for the keyword nobody buys on
First page on Google. Eighteen thousand monthly visitors. Conversion to paid: 0.1%. The keyword had volume and no commercial intent.
Money decisions
The bonus pool sized for the optimistic case
The plan promised $1.2M in bonuses if the company hit target. It hit 80% of plan. Nobody had budgeted for the 80% case.
Founder decisions
The strategy doc you never wrote down
You held the strategy in your head for four years. By year five the company ran on six versions of it, each defended in a different room.
Operations
A Stable Dashboard Is the One to Worry About
The dashboard held steady for six weeks, so nobody checked it. The pipeline broke in March; the board's ARR slide was stale by $300K.
Team reality
Your best intern left for the competitor in week six
Booked to shadow for ten weeks, she ran the biggest launch by week four and had a competitor's offer by week six. What an optics-built internship really costs.
Growth traps
Eighty-six integrations, four that work
The site claimed eighty-six integrations. Four actually worked. Buyers found the gap on the second sales call and stopped trusting the rest of the pitch.
Money decisions
Draw the credit line before you need it
A $5M line sat untouched for a year. Drawn in a soft quarter, it tripped a covenant in two weeks and ended the banking relationship.
Founder decisions
The first ten employees who carried the wrong values
The values were on the wall. The first ten hires lived different ones. By employee thirty, the wall version was a fiction nobody bothered to update.
Operations
SOC 2 takes eight months, not six weeks
A buyer asked for SOC 2 in October for a year-end close. The audit takes months, not weeks. The deal died because nobody had started.
Team reality
The DEI metric reported without context
Twenty-eight percent. The number went into every board deck. Nobody asked what it measured, against what benchmark, or whether the trajectory was right.
Growth traps
A twelve-week launch that froze the company for a quarter
One product line, scoped at twelve weeks, quietly stalled the rest of the roadmap for a quarter. Why a big launch costs two to three times its headline.
Money decisions
Unhedged currency exposure
The contract was in euros, the costs in dollars, and the rate moved before the cash arrived. The deal lost its margin on an exposure nobody hedged.
Founder decisions
The roadmap you couldn't defend
The board asked why those four items. He gave four different answers. None was the real one. A roadmap of compromises dressed as strategy.
Operations
The billing system only a former contractor understands
Production revenue ran on a service nobody could fix. The contractor who built it had quit three years earlier and replied to email when he felt like it.
Team reality
47 Action Items, 2 Done
Three days, twelve people, a beautiful venue, forty-seven action items. Six months later, two were done. A vacation in business clothing.