Is Triple Triple Double Double good enough in B2B venture deals anymore?
You know the path: $1m ARR → $3m ARR → $9m ARR → $18M ARR → $36m ARR → rocketship.
Here’s the thing. On the one hand, of course it is. That compounds to 50%+ growth at $100m+ ARR. That’s a great investment. A fundamentally solid, category-defining company that can compound for a decade.
On the other hand… if you’re a VC today, there is a lot of pressure to swing for the fences:
- That deal is being compared to AI startups growing 3x-10x faster
- Your job is on the line to get into those deals
- LPs are expecting those deals
- 50%+ growth at $500m ARR is the new bar for a strong IPO
And also:
- There is massive inflation at seed & A pricing
- Founders expect FAR higher valuations for T3D2 than they used to
- In many cases, ownership is also lower at seed especially
So what do you do?
The Math Still Works (In Theory)
Let’s be clear: A T3D2 company is still an exceptional outcome. If you invest at $10m post at Seed and own 15%, and that company follows the classic path to $100m ARR at 50%+ growth, you’re looking at a $500m-$1B+ valuation at that stage. That’s a 50x return. That’s a fund returner from a single Seed investment.
The thing is, that math is under pressure.
But The Comparison Set Has Changed
Here’s what’s actually happening in partner meetings today:
Partner A: “I want to do this SaaS deal. $2m ARR, tripled last year, strong unit economics, experienced team. They’re asking $25m post.”
Partner B: “That’s interesting. But look at this AI infra company. $500K ARR, 10x growth last quarter, every Fortune 500 company is calling them. Same $25m post.”
Partner C: “And I’ve got an AI agent company that went from $0 to $5m ARR in 6 months. Also $25m post.”
Guess which deals are getting done?
The T3D2 deal looks slow by comparison, even though it’s objectively fast. It’s the same reason a 30% YoY public SaaS company gets punished while it would have been celebrated five years ago. The goalposts moved.
The Valuation Inflation Problem
But here’s where it gets really painful. That same T3D2 company that would have raised at $8m-$12m post-money at Seed in 2019-2020 is now raising at $20m-$30m post. Why?
- Founders know the market. They see AI companies raising at insane multiples.
- There’s still a lot of capital chasing deals, even if it’s concentrated at the top.
- Seed funds have gotten bigger and need to deploy more capital.
- The “standard” Seed round went from $2m-$3m to $4m-$6m+.
So now you’re paying 2-3x more for the same growth trajectory. Your ownership at Seed has gone from 15-20% to 10-15% or worse. And the AI comparison still exists.
The math gets a lot harder when you’re modeling a 30-40x instead of a 60-100x.
The LP Pressure Is Real
I’ve talked to a lot of VCs about this over the past year. Here’s what I keep hearing:
“Our LPs are asking us what percentage of our portfolio is in AI.”
“We need to show we’re not missing the platform shift.”
“The fund will be judged on whether we got into the category-defining AI companies.”
This isn’t theoretical. This is happening in quarterly LP calls. LPs want exposure to AI. They want to hear about the next OpenAI portfolio company, not about a steady SaaS business hitting its T3D2 targets.
And if you’re a mid-level partner or principal? Your promotion literally depends on whether you sourced the firm’s next breakout company. A solid T3D2 deal won’t get you there. You need the 10x outlier.
So The T3D2 Deal Can Actually Get You Fired
Here’s the dark reality: even if the T3D2 company becomes a great outcome over 7-10 years, you might not be around to see it.
If you pass on the fast-growing AI deals to do the solid SaaS business, and those AI deals become monsters, you look like you missed the wave. If you do the T3D2 deal at an inflated valuation and it grows exactly as expected but doesn’t become a fund returner because of the entry price, you look like you overpaid.
Either way, in 2-3 years when the firm is evaluating performance, you’re being measured against your peers who swung for the fences. Even if they struck out more often, if they hit one grand slam, they’re the hero.
The Founder Perspective
If you’re a founder with a T3D2 trajectory, here’s what this means for you:
The Good News:
- Your business is fundamentally sound and valuable
- There will always be smart investors who understand this
- You’re actually building something that can scale predictably
The Bad News:
- You might get less attention than AI companies
- Valuations might not keep pace with your expectations
- You need to find investors who are playing a different game
The Reality:
- Focus on finding investors who have conviction in SaaS economics
- Don’t try to position yourself as something you’re not
- Be prepared for a more disciplined fundraising process than AI companies are experiencing
So Is T3D2 Still Good Enough?
Yes. And no.
Yes, because the fundamentals haven’t changed. A company that can triple twice, double twice, and maintain 50%+ growth at scale is an exceptional business. Those exist. They return funds. They create generational wealth.
No, because the context has changed. The pricing has changed. The opportunity cost has changed. The career incentives for VCs have changed. The LP expectations have changed.
A T3D2 deal at $10m post with 20% ownership is a no-brainer. The same deal at $30m post with 12% ownership in a world where AI companies are growing 5x faster? That’s a much harder decision. Even if the long-term math works.
What I Tell Founders
When founders ask me about this dynamic, here’s what I say:
Build the best business you can. Don’t try to be an AI company if you’re not. Don’t optimize for growth at all costs if your model requires discipline. Find investors who understand your path and have the patience and conviction to back it.
The best VCs will still do these deals. They’ll do them at reasonable prices with good ownership. They might just take longer to find.
What I Tell VCs (When They Ask)
The best investments often come from going against the grain. If everyone is chasing AI at any price, maybe the real alpha is in the overlooked T3D2 SaaS business that you can get at a reasonable valuation.
But I also get it. You’re not operating in a vacuum. You have bosses, you have LPs, you have a career to think about.
Just remember: the T3D2 deals from 2015-2019 that everyone passed on to chase consumer social or blockchain or whatever the hot thing was? A lot of those became Gorgias, Deel, Notion, Figma.
The companies that just steadily executed, grew predictably, and built real businesses.
Those deals were great then. They’re still great now.
You just might have to fight harder internally to get them done.
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