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The Great Reshuffling

❝

“Should I stay, or should I go?”

I'm on a plane flying back from a week in SF. During my time there, I:

Had dinner and drinks with 25 CFOs
Had beers with 50 finance professionals
Had like 57 coffees with banker and investor friends

To state the obvious: I had a lot of liquids.

The consistent theme across all three groups, who all function inside the same ecosystem, is an ever-present angst. A haunting anxiety about whether they're working on the right shit, and a begrudging awareness that the ground beneath them has shifted.

There's been a lot of back and forth on X lately about the "permanent underclass" in SF (ONLY making $500K a year!?!).

— # (#)

The TL;DR:

There's a group of ~10,000 people who in the last five years have reached retirement wealth, cashing out $20M+
- Anthropic just ran a secondary and capped it at $30M per person. 75 people hit the $30M bogey.
  - Good luck buying real estate there. You'll have to live in a hovel
There are so many more in SaaS who thought they were going to hit the lottery, and didn't
So, what should people making good but not retirement money do, now that the standard tech path to wealth has changed?

Here are three anecdotes from my trip. And yes, anecdotes are anecdotes… Conversations, a point in time, not a dataset. But there’s a lotta truth in anecdotes.

1. A CFO of a $50M ARR SaaS company, six years in, telling me he's thinking about jumping to an AI company rather than playing for an exit at his current spot (which is hard-pivoting to AI itself). They're talking about hiring a banker in their next board meeting. Even if he gets the sale done, it's for a lot less than he thought it would be two years ago. Closer to $300M than $1B.

And also, who is buying a $50M ARR SaaS company right now?

His job is going to be way harder
People are going to be mad he sold it for less than they expected
His personal outcome may not be as hot

Regardless, you do want to have an exit to something you started. (Ask for the carve-out, my guy!)

2. A banker in cybersecurity now working on more defense deals than SaaS security deals, because his network yanked him over there.

He admits he's not a defense person. He did not study military history in college, but did enjoy the Brad Pitt movie Fury
It's a natural adjacency to security, and many of the CFOs in his network are taking jobs there. He knows who butters his bread
In reality, the defense tech companies are more near-term IPO candidates than the cyber ones
This will open up transaction value on debt and follow-on offerings as well

3. An investor whose IC won't fund anything with the word "SaaS" attached to it. AI, Defense, or Hardware/Compute. If it says SaaS don’t “pass” go.

Even if some SaaS companies are good companies, the firms are thinking about their investment brand.
They want to credibly claim "we are the #1 investor of hypergrowth AI companies at the Series B and C stage."
Also, see anecdote #1. They're related.

Observation #1: Whewwww. It's good to not live in SF right now. I’m editing this post from a retirement community in Naples, FL. Not only am I the only person who works in tech, I'm the only person working this Wednesday.

Observation #2: The common thread is that these are successful people in their early 40s. They've built great careers, but ones that haven't been long enough to accumulate F'you money.

Bobby Axelrod, early Anthropic employee

Now they're looking back and wondering if they made the right choices.

It feels like there's been a great reshuffling, and I'll get lost in it if I don't play my cards right.

As Dickens said, it was both the best of times and the worst of times.

Early and mid-career angst

I was previously under the impression that the angst was at the entry level. Just see the college grads booing their commencement speakers when they mention AI. It sucks if you got a CS degree and you thought you were going to be flooded with six-figure offers post graduation.

But this angst is everywhere, especially among the elder millennials. Regardless of age, everyone is wondering what they want to be when they grow up.

A lot of the problem here is the comparison. They still have great jobs and are well paid. But if they look at peers five years older, those people might have joined a HubSpot, gone public, and made bank. Comparison is the thief of joy when you're looking at the people who got their cash-out moment in SaaS just before they seemingly pull the tree fort ladder up and shut the door.

What's also frustrating is that the difference between who got the retirement-level wealth event and who is still working on a salary basis isn't just based on merit. It's based on a lot of luck. A ton of luck.

A lot of us got into the SaaS game for the hope that our equity turned into something. Maybe you didn't take the highest base salary, because you wanted to bet on the ride. And now you're sitting there asking:

Is AI going to diminish (or take) my job in some way?
Can I learn it fast enough to be valuable?
If I do learn how to be dangerous with AI, will the value accrue to me, or to the company (and I'm just lucky to still have a job)?

TBH… most of the people in SaaS did not get into SaaS because it's what they always wanted to do since they were eight years old. They didn't sit in their elementary school classroom and go around the room and one kid says "I want to be a police officer," another says "I want to be a fireman," another says "I want to be a vet," and Ned says "I want to do sales in B2B SaaS!"

Literally McNulty from The Wire

People did it because the market was growing fast, SaaS seemed like a more sure bet than non-tech, and these were high-retention businesses where if you worked hard, a rising tide lifted all ships.

The path forward

Taking stock of the sentiment, what are the different levers people can pull in a job negotiation?

Since starting a recruiting arm, what I've noticed is that people are usually bad at picking what game they're playing. They fail to maximize a win in a specific area. Instead they spray and pray across title, equity, and base. But it's impossible to achieve all three in equal parts.

When I think this through, I run people through the levers.

1. You can maximize for your W-2 cash comp. I did this at Veeam. I wanted to live in a nice apartment in Boston and impress my girlfriend. Also, they didn't give equity to people outside of management at the time (I was too dumb to even know to ask for it if I’m being real honest). It's easier to do this at a steady-eddy company (sub-30% growth, over $500M in revenue). Could be a late-stage startup or a company that IPO'd in the last five years but market cap is down big.

2. You can maximize for total equity comp. I did this at Snyk. I even gave part of my salary back for more equity. I went down in cash the first year at my new job. I said give me a damn ticket to the show.

Sometimes you gotta just ride the horse (unicorn) in the direction it’s going

3. You can maximize for title (and experience). I did this at PartsTech. I wanted the CFO title. I NEEDED IT. I NEEDED IT. LETS GOOO. They gave me the keys to run around and open all the doors. They trusted me with more than a reasonable person should trust me with (thanks, Greg!). There was some equity upside (which worked out), but I was also making less cash than someone who was, say, a senior director of finance at a Notion or an Airtable.

You could also maximize for lifestyle, philosophical alignment with your CEO, and the ability to bring your dog to the office. That's actually what my now-wife did. She filtered for companies where you could bring your dog to work in Boston, and HubSpot was one of the three. But that's not really the type of newsletter I write.

If you're trying to maximize your outcome, be honest about what game you're playing. Which levers are you willing to sacrifice?

So, where's the arbitrage?

It used to be: take a Series B company with a great investor and solid unit economics and RIDE THAT HORSE, BABY.

That was a pretty safe strategy. Now there are two paths I'd point to.

The first: work at a fast-growing AI company that has a real technical advantage and doesn't have a lot of finance or GTM DNA yet.

Just being in that environment is going to be a massive educational boost
It's going to be the equivalent of "where you went to college." Pick right and it's like you went to Harvard or Stanford
These AI companies are paying attractive salaries on top of equity, which wasn't always the case in SaaS. They have crazy ARR per head and war chests of funding, so they can pay more cash than startups historically could or would
However…expectations are higher. They want you AI pilled. They want more work with fewer hires. They might want you in the office nine hours a day, six days a week.
Net net: if you make it two years, you're in the club. If the company works out, you can use it as a jumping-off point for an even better role at the next wave of AI companies. But also, the company may be total vapor wear and it was a silly journey into the abyss.
- Remember: the frontier eats people too (see: donner party).

The second: be the #2 at a company that's lost its sheen.

I want to stress that you want to be the person behind the person, in some real capacity. You do not want to be an IC somewhere in middle management with no ability to impact management decisions. no bueno.

Wait, but is it possible to have a great job at a "bad" company? Yes.

I asked my Mostly Growth cohost Kyle Poyar this.

Apple | Spotify | YouTube

He didn’t buy it. He told me: The career value of being a mediocre employee at an amazing company is usually higher than being a star at a mediocre one. Right, wrong, or indifferent, a rising tide lifts all ships if you worked at AirBnB in 2015 and were just mad decent.

I took the opposite side. Put me at Arctic Wolf. Let me be the #2 there, make a ton of salary monies, and expedite my path to CFO.

Arctic Wolf catching strays for absolutely no reason.

Three more anecdotes for you (I think I just wanted to type the word anecdote a bunch of times; there’s something about typing it really fast and getting it right):

Craig Conti, CFO of Verra Mobility, gave me counterintuitive advice on my pod:
- "Don't go work at that hot AI company. Go work at that paper mill that's going out of business."
- Part of that was in jest. I don't want to work at Dunder Mifflin and neither does he.
- The point he was making is that there's arbitrage in places where the talent bar isn't world beating, because you get to do things at year three that you wouldn't get to do at year eight somewhere shinier.
Bruno Aniq, the CFO of Wellhub, described something similar about putting in years at AOL well after its glory days.
- He called the company "the cockroach of the internet."
- The sheen was gone, but they handed him the keys to a number of projects that accelerated his trajectory to his first CFO seat.
And finally, the history dork that I am, it reminded me of someone I covered in the History of EBITDA, cable cowboy John Malone.
- A brilliant and motivated guy, he left McKinsey to help run TCI, a failing cable company out of Utah. Cable TV?
- He could have gone almost anywhere. He took the broken toy in a flyover state and turned it into a media empire.

Most of the people I consumed liquids with this week are running the math on comp and title. On what it would feel like to have that “LinkedIn crush” of a title at Lovable or a Vercel (credit to Molly Graham for that bar). And yet, nobody is running their career math on experience. That's the lever that's currently mispriced.

Unsexy might be sexy, depending on where you want to go.

Shit, take it from a guy who sold a lotta brake pads on the interweb.