Nobody Tweets About Month 7 in Procurement
The Unicorn Porn Industrial Complex Is Making You Feel Like Shit for Building Real Software
“We got it,” she texted.
After weeks of our champion modeling business cases, late-night texts dissecting objections, and that demo that went so well, their CFO almost smiled, we finally received budget approval from one of the largest banks in North America.
I grabbed the champagne we’d been saving, made my way to our VP of Sales’ desk, bottle in hand, grinning like an idiot.
She looked me up and down. “I hope you didn’t open that.”
“But... we got it?” I stammered.
“We got budget approval. Now we have to go through procurement.”
“How long does that…”
“Months. And don’t say shit to the board yet. It ain’t over ‘til the wire hits.”
Deflated, I deleted my draft message to investors and slunk back to my desk.
That “done deal” took eight more months to close, even though we timed it perfectly: a new EVP hire who wanted to drive change, the right budget cycle, and a champion with real power. After demos, due diligence, and internal board approval, we still had:
Eight months in procurement
Two rounds of legal reviews (both sides)
A security audit that restarted everything
Walking away from the deal twice
Two bank reorgs
A new EVP replacing our champion
A bajillion contract redlines
One lawyer’s call that lasted four hours
This, my friends, is real enterprise B2B software.
The Unicorn Porn Industrial Complex
Meanwhile, on Twitter/X:
“$2MM in three months used to be impressive. Now we expect it in ten days. Right now, momentum is the only moat.” - Bryan Kim
I can’t get lawyers to review an MSA in ten days.
Sigh, where do I start? This messaging isn’t just annoying, it’s dangerous. Because founders building real enterprise businesses are looking at this shit and thinking they’re failing. It’s like we briefly learned about growth at all costs during the heady ZIRP days, and now we've completely forgotten.
Let’s break down the numbers with the math everyone seems to forget exists.
$54,794.52 MRR × 36.5 = $2,000,000 ARR
Cool. Cool. Cool. Now show me:
The actual signed contracts
What happens when those subsidized LLM credits run out
Month 2 retention
Month 6 retention
CAC payback that isn’t fictional
Whether a single dollar is from a company with a procurement department
I could slap together an AI wrapper, charge $20/month, dump $50/month in free credits into each account, and watch people sign up. It would take me about ten days to hit those numbers, too.
You know what I couldn’t do in ten days? Get legal approval from a single Fortune 500 company.
What Actually Happens in Enterprise
Here’s the timeline nobody tweets about:
Month 1-2: The Honeymoon
Your champion loves you
Demos go great
“This is exactly what we need”
You start sizing your Series A and worrying about how you’ll manage your overflowing pipeline
Month 3-4: Reality Arrives
“We need to bring in IT”
“Security wants to do a review”
“Can you fill out this 47-page vendor questionnaire?”
We’ve onboarded you to NetSuite; now you get to re-enter that vendor questionnaire.
Your champion stops responding as fast
Month 5-6: Procurement Hell
“We’re mandated to get three quotes”
RFP goes out (to your competitors)
Bake-off begins
The deal you thought was done is now competitive
Month 7-8: Legal Thunderdome
Your lawyer meets their lawyer
Liability caps
Indemnification clauses
You need to double your insurance, which triples your premiums somehow
Data processing agreements
That one sentence that takes four calls to resolve
Month 9-10: The Near-Death Experience
“The deal is falling apart”
War room convened
Your champion’s boss has concerns
New stakeholder appears who hates everything except your competitor that they once implemented and are connected to on LinkedIn
Month 11-12: False Finishes
“We’re all set, just needs final signatures”
Org reorg happens
“It’s been more than 6 months; we need to redo the pen tests.”
New stakeholder wants to review everything
Your champion gets promoted/leaves/reassigned
Month 13-18: Actual Close
Wire hits
Now you can open the champagne
Now you can tell the board, but they’re already focused on the next deals.
This isn’t broken. This is the business model.
The Data Nobody Wants to Hear
Kyle Poyar’s research on growth benchmarks:
7.5% of startups hit $1MM ARR in under 2 years
3.3% hit it before year one
The median time to $1MM ARR? 2-3 years. You read that right, two to three years.
But wait, what about all those “overnight successes”? Kyle has the receipts.
Lovable: Eighteen months of development before their breakthrough, following previous unsuccessful attempts (GPT Engineer) that fizzled after launch. The “sudden” success had a year and a half of groundwork.
Clay: Six years of grinding before revenue traction. Six. Years. Most teams and investors would’ve called it quits, but then growth exploded. But nobody tweets about years 1-5. Side note: There are so many Clays, I think I may have used an earlier version, but I’m not sure.
StackBlitz: Seven years clawing to $700K ARR. Then Bolt.new hit $4MM in four weeks. Everyone talks about the four weeks. Nobody mentions the seven years.
And then my favorite, Cursor: the one everyone forgets. Eleven months of private development before their March 2023 launch. Then nine more months to hit $1M ARR. Now everyone screams about their explosive growth from $4M to $50M ARR in 2024. But that’s 20+ months after they started building. With zero marketing spend. And with a product developers literally couldn’t live without once they tried it.
So despite what you’re hearing, the pattern isn’t “build fast, win big.” It’s “build for years in obscurity, then maybe something hits.”
Why “Momentum as Moat” Is Specifically Wrong for Enterprise
Consumer/PLG businesses can move fast because:
Individual buyers making individual decisions
Credit card transactions
No procurement departments
No legal review
Can pivot weekly based on usage data
Enterprise businesses cannot move fast because:
Committee decisions with 8-12 stakeholders
Six-figure+ contracts requiring CFO approval
Mandatory procurement processes (seriously, it’s in their policies)
Legal reviews on both sides
Security audits
Integration with systems they literally cannot break
Reference calls from customers you don’t have yet
You know what the actual moat is in enterprise?
The fact that it takes 8-18 months to close a deal.
Your competitors have to climb the same mountain. Every logo you land is a castle they have to siege. Each implementation becomes integration debt for their competitive displacement.
Fast-follow doesn’t work when the “follow” takes a year and a half.
What This Means If You’re Building Enterprise
If you’re six months in and don’t have $1MM ARR, you’re not behind. You’re on time.
If your deals take 6-18 months to close, that’s not a bug. That’s enterprise.
If you have three pilots and zero revenue, you’re further along than the “10 days to millions” crowd with their phantom churn.
If procurement is killing you: Everyone. Every single company. This is the game, try to see it as a challenge, and remember it’s business, not personal. Well, most of the time.
Could you pivot to SMB? Price at $99/month? Let people swipe cards? Sure. Some companies should. But if you’re building for enterprise buyers, you’re playing a different sport entirely.
The Real Metrics That Matter
Stop comparing yourself to consumer SaaS:
Bad metric: Time to $1MM ARR
Good metric: Contract value + renewal rate
Bad metric: signup velocity
Good metric: Pipeline coverage at 3x quota
Bad metric: Daily active users
Good metric: Successful implementations/champion retention
Bad metric: Viral coefficient
Good metric: Reference customers willing to take calls. Customers who take you with them when they switch jobs.
Your $500K annual contract, which took 14 months to close, is worth more than $2MM in MRR that churns at 15% per month. Because in 12 months, you’ll still have $450K. They’ll have $350K.
Durability beats velocity in enterprise.
What Actually Kills Enterprise Startups
It’s not slow sales cycles.
It’s running out of money before the pipeline converts.
The math is brutal:
9-month sales cycle
Need 3 months to onboard/implement
First renewal at month 21
Need 18 months of runway when you start selling
Most enterprise startups die in “the valley of death”, that 12-18 month period where:
Demos are going great
Pipeline looks incredible
The board is asking about revenue
Your bank account is bleeding out
Nothing has closed yet
This is why enterprise founders need to:
Raise more than feels comfortable (you need longer runway)
Start selling earlier than feels ready (add 6 months to your timeline)
Have fewer, bigger targets (ten $500K deals > fifty $100K deals)
Get comfortable with awkward board meetings (where you explain why nothing closed yet)
Find the right investors who get B2B Enterprise, founder-investor fit is a real thing.
The Truth About Enterprise That Nobody Tweets
Real enterprise deals require:
Vendor insurance certificates
SOC 2 compliance (Type II, they don’t care about Type I)
Redlined vendor agreements (every single one)
Multiple reference calls
Security questionnaires that take 40 hours to complete
Proof of financial stability
Proof of D&O insurance
Integration with systems deployed in 2008 that nobody understands anymore
Your buyer isn’t being difficult. They’re betting their job on you.
They’re rolling you out to 5,000 users. If your shit breaks, they’re in a conference room explaining why they bought from a startup instead of the incumbent. Their boss is asking why they didn’t go with the “safe choice.” Their career is on the line.
They should move slowly. It’s the rational decision.
So What Do You Do?
If you’re building consumer/PLG, great. Move fast. Tweet your revenue. Optimize for momentum. None of this applies to you.
If you’re building enterprise:
“Don’t believe the hype” - Public Enemy, 1988
Stop reading Twitter unicorn porn threads. They’re not for you.
Stop feeling behind because someone’s MRR × 36.5 math went viral.
Stop apologizing for deals taking “too long.”
Your job isn’t to speedrun it. Your job is to survive it.
Start measuring:
Contract value
Pipeline quality
Champion conviction
Renewal rates (even from pilots)
Reference customer strength
Keep the champagne in the office. You’ll need it when the wire hits.
Just don’t open it when you get budget approval, like me, when I was a naïve idiot.