On Timing

I don't give a fuck about timing anymore

Author

Noah Jacobs
July 05, 2026

2026.07.05

CLIX

[To hell with Timing; The Twilight Zone; Fallout; The MBAs Have Replaced the Pirates; Contrarian By Nature; Happy 4th]

Thesis: Taking action you believe is right gets a better return than looking for consensus or waiting for the perfect timing.

[To hell with Timing]

I got an exceptional piece of solicited advice from my Jiu Jitsu coach a week or so ago.

He told me to stop waiting for the someone else's mistake to advance my position or escape. Rather, go ahead and leverage proper form and technique on your own terms.

I have abnormally strong defense. This means I can sit in a compromised position for longer than is natural & I rarely if ever panic. I'm stuck sitting there waiting for the other person to mess up, though.

His point was I should stop waiting. I don't always need to be sneaky and clever. Sometimes, I can just very clearly and blatantly do the basic escapes with good form even if the top person is pressing me quite hard.

The same goes for attacking; I can do less waiting on them messing up and more asserting what I want to happen until it does.

I applied this advice and had immediate amazing results. It's rare you get such effective feedback.

To hell with timing; play your own game, regardless of theirs. You need to be aware of what they're doing and take advantage of it when they mess up, but you can also more aggressively do more of what you know works, too.

As a recovering finance bro, I think about markets and timing a lot.

The market my startup, WhiteWhale, is playing in, is really, really weird right now. Too much money was raised, and now there's nominal acquisitions, aggressive pivots, and overall consolidation.

This, I believe, is downstream of a Silicon Valley that has lost the spirit of the Pirate and had it replaced with the spirit of the MBA. Like I was waiting for good timing in jiu jitsu, they’re sitting they’re waiting for market consensus and someone else to make the first move.

You need to remember that you can make moves and assert yourself and take risks. That’s part of the game.

The bigger risk, at some point, is waiting & following.

[The Twilight Zone]

The market I am playing in is fucking weird. Overall, I'd call it 'data for sales & marketing teams.' But, the lines here are really thin, because a lot of 'infrastructure' companies (email sending, workflow automations) also do data and data companies do infrastructure.

In the past few months, here are some of the highlights:

I don't know how much Warmly, or CommonRoom were acquired for, but I will attempt to back into each in HubSpot & Zoom 10q's when they release. Rumor's about Pocus's acquisition price are not good.

[Fallout]

I find this all so weird because it feels like we're entering the fallout zone of a space where so much more money was invested by VC than was ever warranted.

If you ignore the revenue from the CRM company’s data projects, the revenue of the big data companies in the space is maybe $2B per annum (Lemlist $53M + Apollo ‘approaching’ $200M + 6Sense $200M + ZoomInfo ~$1.25B + Clay $100M + RocketReach $40M + DemandBase $200M). A lot of these numbers are self reported, unaudited, and of questionable reliability, and I’m probably missing a few big ones, but I’d be shocked if I was missing more than another $1B lying around somewhere. And, to boot, calling some of these companies truly data companies is a stretch.

Note the vast majority of this comes from one company that sells contact data that a lot of people in the market are arguing is too expensive because it’s increasingly commoditized.

Yes, $2B is a lot of money in terms of absolute dollar value. And it is big enough to make it a very attractive pie for myself & Jack; while we only play in a sliver of the $2B market (won’t even touch contact data!), every dollar we earn puts us in a better position.

But, this is NOT a lot of money for the companies going out and raising tens of millions of dollars and some even getting valued as unicorns.

If your company gets valued at even $100M, you’d have to hit $10M ARR and sell your business at 10x Revenue to break even (VC’s don’t want to break even, they want a 10x return!).

Even if you did this, if your churn was 9% a month (not uncommon in this space!), and you're not even profitable yet, whose going to buy you for 10x revenue to actually make it break even?

Put another way, if you’re value at anywhere near 9 figures, you’re already at 1/9th the public value of the company that does more than half of all of the revenue in the space. To get your investors their 10x return, you need to be worth more than the company doing half of the fucking revenue.

You'd better have some really differentiated technology, but that's hard to do when you're pressured to build the everything tool and water down any differentiation you have. And, of course, there's the greater fool theory, but that's not something I'd bet on when exit planning.

The only thing I can think of is maybe these companies are arguing they’ll expand the SaaS market or get revenue by firing a bunch of sales people? The AI SDRs claiming they do that aren’t fairing so well (source: talk to literally any sales person or sales leader instead of the founders selling it).

Any who, there’s really not much place left to turn for a lot of these companies other than an acquisition from an incumbent, but who knows how much that is for. The Corp Dev team's I've spoken with in the space have struck me as very shrewd and likely to get a favorable price. Also probably why no one ever says what they got bought for.

The more time I spend here, the worse of a market I think this is for VCs.

You already know how I feel about AI Valuations, but this does make me wonder how bad other software markets are.

[The MBAs Have Replaced the Pirates]

I think the glut of companies with such aggressive funding in this space is a down stream symptom of a perversion in Silicon Valley: it's shifted from the gun slingers and risk taking mavericks to consensus seeking MBAs & rent seekers.

When I think of entrepreneurship and risk taking, I think of:

Gets me fired up every time

I don't think of:

  • Someone finishing a degree at a Top 20 University

  • Working at either a startup that's so big it's become big tech or a management consulting job

  • Moving to the Bay because tech

  • Making a slide deck that explains how the thing you haven't built yet will one day be really big

  • Vaguely 'doing AI' because it's the main thing right now

  • More slides on tam, sam, som, moat, differentiation for a product that doesn't exist yet

  • Raising a bunch of money to spend it within a year and either raise more money or go out of business.

  • Go build on the cloud with docker and kubernetes because you're supposed to build on the cloud with docker and kubernetes and hey AWS gave us $100K in free money to do it!

Listen, if you need to raise money, go and raise it. But a lot of the time it just feels like the 'track you're supposed to do,' sponsored by this self reinforcing feedback loop that even if you don't need to raise in a vacuum, because other people are raising you now need to in order to keep up!

Do what you believe is right, and do it with good form. To hell with the timing.

[Contrarian By Nature]

I really believe that all of the best founders / investors / VCs don't give a fuck what anyone else is doing. They just go for it.

Sure, they're aware of consensus, but it's far from the most interesting thing they spend their time focusing on.

One of my friends with a very real product and very real business with an incredible asymmetric opportunity is raising right now. Apparently, the largest fund in the world will only invest at this stage if you 'already have a term sheet in hand' from another investor.

That is insane. That's literally waiting for consensus.

I've written about being a contrarian before. I'm starting to wonder if being a contrarian is actually a necessary condition to get a truly out sized return. If you don't take a contrarian stance, you're by definition betting on market consensus. Where's the out sized return in that?

A good trade becomes a bad trade if everyone has already placed it.

Regardless, you're certainly not waiting to move a particular way until you're 'supposed' to move or other people say the timing is absolutely perfect. You're just moving as you see fit.

At WhiteWhale, running a lot of our own scrapers was something everyone told me was a waste of time, or at the least was very confused about, as was building on prem servers and a slew of other technical decisions.

These decisions, though, are some of the big reasons we've been profitable nearly the entire time.

If we would've listened to the market's consensus (now is the time to just go full port into cloud, use apis, don't waste your time), we'd have literally the same product everyone else does, and we'd probably be losing money.

We just did this shit because we thought it was right. And so far, it's working.

And all of this is without mentioning the number of people who told us we needed to raise. Thank god we didn't, or we might be in the weird growing fallout zone starting to consume our market.

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[Happy 4th]

You have to remember, I have no fucking idea what I'm doing.

But what I do have is a growing confidence that I will figure it out, no matter what comes.

And I'll take advice that I think is good, but I have an allergy to any prescribed path.

Maybe that's risky, but it's intoxicating, too.

The spirit of the pirate is a lot more enriching than the spirit of the MBA. It makes you feel so much more alive and so much more real.

To hell with timing, you do you. Conveniently, this is inline with the mythology of America & our independence day.

Happy 4th, keep the spirit of the pirate alive.

Live Deeply,