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A CFO Explains: The History of the Secondary Market
Employees (and investors) are far more likely to get rich off secondaries than IPOs. And the trend isn't reversing...
In 2025, the secondary market hit $233 billion in transaction volume - up 53% from the year before. The IPO market delivered $44 billion.
(Takes out TI83 from middle school…)
Secondaries outpaced new public offerings by more than five to one.
In this mini documentary, we're going to go back to the beginning, to understand the mechanics, and give you the CFO's operating manual for how the secondary market actually works.
We'll cover:
Where secondaries came from (spoiler: Facebook's parking lot)
Why they exploded,
Who wins and who gets jet skis too early,
How to run one without blowing up your cap table, and
The newest chapter of this story: GP-led continuation vehicles, which are becoming one of the most important financial structures in private markets.
Shout out to the following distinguished RTN guests who helped me form an educated perspective on this: Mike Jung, Jason Pate, Greg Henry, Scott Voss, Curt Sigfstead, Brandon Sullivan. Hopefully we got your good side.
You can find the entire thing in long form written content below.
Here’s the video:
A CFO Explains: The History of Secondaries
The sleepy, opaque, "how do I even get in on this" corner of private finance — where shares in private companies trade hands in back-channel deals — now moves more money than the NYSE and Nasdaq hand out in new IPOs.
As a founder and an employee, it's actually more common to get rich off secondary transactions before going public than from liquidating shares on the once coveted NYSE or Nasdaq (giving a new meaning to the term ‘tendies’).
And consider what’s happening in public markets at the same time: Figma, CoreWeave, and Klarna — three of the most hyped IPOs in years — went public in 2025. Figma is down 80% from its first-day pop. Klarna is down more than 60% from its debut. CoreWeave has oscillated wildly depending on what day of the week you check. These were the supposed proof points that public markets were back. (They were not.)
The whole ballgame has shifted.
Here's the number that explains how we got here: the average time from founding to IPO used to be around six years. Google, Salesforce, the whole dot-com generation — six years and you're ringing the bell. Jay Ritter, a professor at the University of Florida who tracks IPO timelines obsessively, puts the current average at 14 years.
Fourteen.
Which means you could join a company at 28, spend what should be your entire early-career wealth-building decade there, and still be years away from a liquidity event. Meanwhile, you've got options you can't touch, taxes you didn't expect, and a down payment on a house that exists only as a number on a cap table.
That's the pressure cooker that built the secondary market.
Companies stay private longer because they can. The private markets are bigger, more institutional, and frankly more forgiving than quarterly earnings calls and a stock price that moves on a Fed whisper. If you can raise $10 billion from sovereign wealth funds and growth equity firms without ever talking to Jim Cramer, a lot of founders choose that.
But that choice creates a debt. A social contract with employees and early investors that says: your upside is real, we just need more time.
The secondary market is how you make good on that contract.
In this piece, we're going to go back to the beginning, understand the mechanics, and give you the CFO's operating manual for how this market actually works. We'll cover where secondaries came from (spoiler: Facebook's parking lot), why they exploded, who wins and who gets jet skis too early, how to run one without blowing up your cap table, and the newest chapter of this story: GP-led continuation vehicles, which are becoming one of the most important financial structures in private markets.
Let's go.
But first, what even is a secondary?
Ben: alright alright, pump the breaks here Mr. Finance Officer. I’m a noob here, what exactly is a secondary?
A secondary transaction is exactly what it sounds like. It's the second time a share changes hands.
The first time — the primary — is when a company issues new shares to raise capital. That money goes directly onto the company's balance sheet. It funds hiring, product development, maybe an acquisition. Primary dollars build the business.
A secondary is different. No new shares are created. The company gets nothing. An existing shareholder — a founder, an early employee, a seed-stage fund that wrote the first check — sells their shares to a new buyer. The balance sheet doesn't move. Only the cap table does.
I've administered a few of these in my day. I'll be straight with you: from a company perspective, there is zero financial benefit to running one. It is a complete administrative pain in the neck. Hundreds of hours coordinating between employees who want to sell, lawyers on both sides, new investors who want in, and existing investors who want more. The company is essentially acting as matchmaker, bookkeeper, and approver — all at once, all for free.
Ben: Alright I think I understand now. I think I see where the Jetski money comes from, but tell me why one would do it in the first place?
We'll get to that. But first, you need to understand where this whole thing came from.
The dot-com hangover that made everyone paranoid
To understand the secondary market, you have to start with the wreckage it was built on.
Mike Jung, co founder and managing director at secondary-focused investment firm Founders Circle, was at Ask Jeeves — yes, Ask Jeeves — in the late 1990s. The stock hit $190 a share. He had options. He was locked up. Then the bubble burst and the stock fell to basically a dollar.
(He still thinks he has tax loss carryforwards from that period.)
That experience shaped a generation of employees and investors. Options felt like lottery tickets, not compensation. The lesson people took away was: paper wealth is not real wealth. Don't count it until you can touch it.
It ain't real until the check clears.
The problem is that lesson calcified into a kind of paralysis. Companies and investors became so wary of giving employees any liquidity that they overcorrected. If you joined a startup in 2005, you might wait 10 or 12 years for any kind of return. And by then, you'd probably left anyway.
Then Facebook happened. And everything changed.
Ben: I’m always excited when you mention Facebook because it’s an easy excuse to include The Social Network clips.
The wild west
Facebook was the first company to let the secondary market run at any kind of scale. And they let it run with basically no guardrails. Mike Jung described it well: Facebook "didn't really put a lot of restrictions on who the buyers were." Hedge funds ran around trying to find any way in. If you were a Facebook employee with vested shares, somebody was calling you.
Twitter was next — and that's where it got really interesting.
Chris Sacca was already an early investor in Twitter through Lowercase Capital. He'd taken part in a $5 million financing round in late 2007 and believed in the company so completely that he couldn't understand why other investors didn't see what he saw. So when he couldn't convince them, he decided to go get the shares himself.
He created four separate funds for the sole purpose of buying Twitter stock. Not through the company. Not through a formal process. Just Sacca and his phone, calling employees, calling early investors, calling anyone who held Twitter shares and might be willing to sell.
JPMorgan's Digital Growth Fund committed the bulk of the capital — over a billion dollars into Sacca's new fund. Over several months, they quietly accumulated around $400 million in Twitter shares from current shareholders at prices between $16 and $21 a share. At $21, that implied a Twitter valuation of about $4.5 billion.
Ben: Alright so who sold?
Sacca bought $100 million from co-founder Ev Williams alone, beating out General Atlantic in a bidding war for the shares. Early investors Union Square Ventures and Spark Capital made up most of the remaining $300 million. By February 2011, Sacca's funds were the second-largest shareholder of Twitter. Only Williams held more.
No formal tender offer. No company-sanctioned process. No disclosure requirements. Just one investor with conviction and enough capital to build a position that would eventually return $5 billion to his investors and land him at number two on the Forbes Midas List.
It was the best seed portfolio in history, built on secondary shares that nobody thought to structure or regulate.
But it was also the exact scenario that made every board in Silicon Valley nervous. If one rogue investor could quietly accumulate a 9% stake in your company without your permission, what else could happen?
Ben: What if the next buyer wasn't Chris Sacca? What if they had different intentions?
That's why companies started putting aggressive transfer restrictions in their bylaws shortly after. The wild west was producing winners. It was also producing chaos.
What nobody had figured out yet was the middle path. A structured, company-sanctioned way to provide liquidity that worked for employees, investors, and the company itself.
That middle path took about a decade to find. And in 2013, Mike Jung and Founder Circle Capital decided to go build it. At the time, they thought the secondary market for venture might be a $1 billion opportunity.
The market did $233 billion last year.
Ben: For those keeping score at home, $233 billion is approximately 22 million Yamaha WaveRunner Jetskis. #notsponsored
Why companies stay private longer
IPO was the only infrastructure for capital access at scale. That changed.
As Slim Charles once said: "The thing about the old days, they the old days."
The Google/Salesforce generation went public ~6 years after founding. Now 14 years average (Jay Ritter). What happened: private markets grew up.
Capital available in private markets is categorically different from 15-20 years ago. Founders can raise $500M+ from sovereign wealth funds, crossover investors, growth equity without filing an S-1. OpenAI raised $40 billion in a single round privately.
Going public is hard. It's a different operating mode. You answer to a constituency that cares about this quarter, not the next decade. A week on every earnings call prep. Your stock moves on news you had nothing to do with. Founders say: I'd rather just build.
But that creates a problem. When you stay private 14 years, you're making a promise to people. An engineer joined at 28, now 42. Paper wealth grew. Has a mortgage, kids in school, parents who need help. Options worth something on paper. Paper doesn't pay for any of that.
Founders took staying private as a feature. Employees experienced it as a bug. That gap is what the secondary market exists to close.
Ben: Seems like a no-brainer to me. Walk me through who makes up these secondary transactions?
The three stakeholders
A secondary transaction has three parties. Each has a completely different problem.
The employees
Most human story. Joined a startup at 28. Took below-market salary because equity made up for it — on paper. Watched the company grow. Valuation went up. Options worth something real now.
But you can't pay your mortgage with options. Can't cover kids' school with a cap table entry. And if you exercise your shares, you might owe the IRS more cash than you actually have.
Here's how that works. You exercise your options — write a check to convert them into real shares. Then Uncle Sam wakes up and says: those shares have a fair market value, and the spread between what you paid and what they're worth counts as income. You now owe Alternative Minimum Tax on an asset you can't sell. Two checks out the door — one to buy the shares, one to the government — for something with no liquid market. I've seen people stare at a bank balance of zero while being paper millionaires. It can be expensive to get rich.
That's the trap. The compensation is real, but the liquidity isn't. Employees need a way out that doesn't require waiting 14 years for an IPO that may or may not happen.
The early investors
VCs have their own clock problem. Raise a fund, deploy into companies, eventually return cash to limited partners — pension funds, endowments, family offices who gave them money. That cycle used to run on 10-year timelines. If companies stay private 14 years, the math breaks down.
You can't tell a pension fund to wait 14 years. They have obligations too.
Over the last four years, LPs experienced a negative net cash flow environment — getting capital called from all their GPs and getting less back. Can't fund new managers. Can't re-up if you're not getting capital back. Scott Voss from HarbourVest described it perfectly: distribution notice in one hand, capital call notice in the other.
Tomas Tunguz posted that over 70% of VC liquidity in recent years came through secondaries rather than IPOs or M&A. The traditional exit playbook — build, go public, return capital — is no longer how most money gets home. Secondaries are now the mechanism. They're the oil in the engine.
Secondaries also give investors a way to increase their stake. Founders are wary of dilution, so there are only so many dollars to go around in a primary fundraise. If a round is oversubscribed, the next best option is to shake some secondary dollars from the tree. CFOs will often reserve secondary allocation for their favorite investors, letting them creep up their fully diluted ownership via common shares. Some investors won't get out of bed in the morning to help a portfolio company if they don't have at least a $50M stake. If you can't get them there in the primary, topping them up with secondary dollars is how you keep them on the ball.
The company
Trickiest. The company has no financial incentive to run a secondary. Zero. No new shares created. No money hits the balance sheet. The company spends hundreds of hours coordinating lawyers, employees, investors — all for free. Most thankless administrative exercise in finance.
Ben: I’m seeing why secondaries have so much friction. So why would companies even do it in the first place?
Because the alternative is worse. Employees who can't access wealth get distracted. Start taking calls from competitors. Leave. The company loses people it spent years building with.
There's another angle too. With a fundraise often comes pressure from investors to uplevel the talent at key positions. Hire a real CMO. Bring in an experienced sales leader. That can be a huge ego blow for employees who helped get the company to this point. But what got you here isn't going to get you there. Allowing early employees now moving into less prominent roles to take some money off the table cushions that blow. Getting leveled is never fun. But it's slightly less painful when you have a new set of jet skis.
Secondaries can also serve as cap table cleanup. Lots of startups have early angel investors and advisors who become increasingly less helpful as the years wear on. If the price is right, a tender is a great juncture to ctrl+alt+delete them off the cap table and send them on their way, fat and happy.
There's a subtler reason too. Jason Pate at Plaid described it well. When you raise a new round at a fresh valuation and tie it to a tender offer, you create something paper wealth alone can't create: a floor. A real price that everyone — new investors, existing employees, the company — agreed to on the same day. That number becomes the foundation everything else gets built on.
Plaid raised $575 million at a $6.1 billion valuation — higher than the Visa acquisition deal that fell through. They structured it so the price investors paid for new shares was the same price employees could tender at, and the same price new equity grants were issued at. One number, across the board. That's a fundamentally different conversation than "trust us, it's worth this much on paper." Paper doesn't hold up in a recruiting conversation against Meta's RSU calculator. A real price does.
The company hadn't had a fresh mark on the business in years. Getting one gave the entire org something concrete to build from.
The company's incentive isn't financial. It's gravitational. Keep the right people in orbit long enough to actually finish what you started.
When is it too early?
Ben: I’m going to guess that it’s a bad idea to run a secondary immediately. When should a company even think about running one?
The answer is simple. It's not about what series you're in. It's about whether you have a real business.
I’ve seen founders take liquidity before they've hit product-market fit. Before they've figured out if anyone actually wants what they're building. That's dangerous. Not because the founder doesn't deserve a paycheck — they do — but because it sends a signal to every investor and employee watching. If the founder is selling, what does the founder know?
VCs will sometimes go along with it anyway. If early founder liquidity is the only way to win a deal or get the ownership they want, some will hold their nose and write the check. But it's risky for everyone involved.
The right threshold isn't a revenue number, though Mike says by $100 million you've probably got a real business. It's more fundamental than that. Is this a sustainable company that could eventually be a standalone public company? If the answer is yes, founder liquidity isn't a red flag. It's rational. Building a company is hard. Building a company while you're broke is harder.
One of Mike's earliest investments — a company called Axiom Legal — had founders on the literal ramen diet. Living in New York, paying themselves nothing. When they finally raised from JPMorgan Partners and Benchmark, part of the conversation was just getting the founders enough liquidity so they could eat something other than cup of noodles. That was the original insight behind Founder Circle: the right amount of liquidity for a founder doesn't distract from building. It removes a distraction.
How to actually run one of these things
Ben: Alright, give the people what they want, how do you actually run one of these things?
A tender offer is the structured version. The company sets a price, says who can sell, how much they can sell, and who's buying. It's a controlled event — which is the whole point after the wild west era.
The hardest question isn't the price. It's: how much do you let people sell?
I call this the Goldilocks zone. There's a floor and a ceiling. The floor is simple — give people enough to exercise their options and cover the tax bill. That's the minimum. If you've ever footed an AMT bill for the first time, you know this feeling. You call around convinced there's a mistake. There isn't.
Most CFOs go a bit higher than that. Enough to put real cash in the bank. Enough for a down payment. Enough for the equity to feel like actual compensation, not a number on a screen.
The ceiling is where it gets tricky. It's the point where someone has made enough money to mentally check out. Bought the jet ski. Booked Cabo. Still has a Slack avatar but stopped building six months ago.
So companies set guardrails. Tenure requirements — typically one to two years before you can participate. Percentage caps — most land between 10% and 25% of vested shares. Greg Henry, who's run two of these at 1Password, used 10% when the company had already done prior offerings and 25% when it was the first one after eight-plus years. The logic makes sense. If people have had multiple bites, keep each one small. If they've been waiting a decade, give them more room.
One rule Greg was firm on: no cspecial terms for executives. Everyone plays by the same rules. That matters more than people think.
Some companies add a dollar cap on top of the percentage cap, especially when the tender pool is fixed and could get oversubscribed. Brandon Sullivan at 2X suggested keeping the absolute amount at a level that isn't life-changing — enough to matter, not enough to retire. And he's a fan of 12-month post-sale retention commitments. You want to sell? Fine. But you're sticking around for at least another year. That solves the Cabo problem structurally, not just philosophically.
Enough to retain. Not so much that it retires.
Ben: I guess you could say there's an art in making people rich. Just not too rich.
The other thing nobody warns you about: communication is half the job. Teddy Collins at SeatGeek said to over-index on education. Town halls. Office hours. Company-provided tax advisors. A lot of employees won't participate simply because they don't understand the process or can't front the cash to exercise. (A cashless exercise feature, where shares are sold to cover the exercise cost, can fix that second problem.)
Jason Pate at Plaid compared the whole process to buying a wedding ring. You spend months learning a skill you've never needed before. You do it once, hopefully well. And then other CFOs start calling you every week asking how you pulled it off.
He wasn't exaggerating. He gets a call a week from late-stage CEOs and CFOs trying to navigate RSU expirations, tender structures, and equity programs built for a world that doesn't exist anymore — the one where companies went public in six years.
Curt Sigfstead at Clio described the employee liquidity piece as one of the most complex parts of their raise. Multiple jurisdictions. Different tax withholding rules in the US, Canada, Ireland. No single platform handles it well. It's spreadsheets and lawyers and a lot of late nights.
Nobody teaches you this in CFO school. Mostly because there is no CFO school.
Not all shares are created equal
Ben: Seems pretty straightforward. Make sure to communicate so you don’t end up like an Eduardo Saverin.
Had to get another Social Network ref in there, huh?
Ben: You know it!
The secondary market is legit. It's also attracted a massive number of grifters.
Here's the thing about buying shares in a private company: you need to know what you're actually buying. Common stock and preferred stock are not the same thing. If you buy common at the price of the last preferred round, and the company gets acquired at or below that valuation, you're probably underwater. Common sits at the bottom of the preference stack. Every class of preferred gets paid first.
Say a Series A investor has a liquidation preference of a dollar a share. You buy their Series A shares on the secondary market at $10 a share. If the exit doesn't clear the full stack, you get a dollar back. Not ten. The other nine only come home if the outcome is big enough for everyone to convert to common and ride the upside together.
In a normal market, common shares in a secondary trade at roughly a 20% discount to the preferred price. That discount reflects the risk of sitting lower in the stack. But in a hot market — 2021 was the poster child — that discount evaporates. Investors were paying employees the exact same price for common shares as the company's newly minted Series whatever preferred. They just wanted in. Didn't care what class. Didn't care about the waterfall.
If all goes well and the company IPOs, all share classes convert into the same publicly traded stock. All's well that ends well. But if the valuation falls before you get there, the common holders are the ones holding the bag.
The best secondary investments are in companies where the preference stack doesn't matter. Where the exit is so good that everyone converts. If you're spending time modeling liquidation waterfalls, you're probably in the wrong deal.
That's the sophisticated end of the market. Then there's the other end.
SPVs have become the strip mall of secondary investing. Somebody gets access to shares in a name-brand company — SpaceX, Stripe, Databricks — and packages them into a special purpose vehicle. The pitch lands in your inbox. The terms: 2 and 20, plus a 2.5% annual admin fee. Sometimes a 10% upfront commission. Sometimes the offering doesn't even specify what class of shares you're getting. Sometimes you don't know if there's an actual share attached to the paper at all.
There's not a lot of disclosure compared to public markets. You're just not required to provide it. So a lot of this is buyer beware — except most buyers don't know what to beware of.
The difference between the legit version and the grift is pretty simple. The legit version: work directly with the company, get their blessing, sit on the cap table, do the diligence on the capital structure. The grift version: raise an SPV off a name, charge egregious fees, and hope nobody reads the fine print.
Ben: And now there's a third version that's harder to categorize.
In 2025, Robinhood started offering tokenized shares of OpenAI and SpaceX to European users. Vlad Tenev stood in Cannes holding a metal cylinder he said contained "the keys to the first-ever stock tokens for OpenAI." The stock surged 13% on the announcement.
Here's the fine print: these tokens are not equity. They're derivative contracts that track the price movement of private company shares. You don't own a piece of OpenAI. You own a financial product that goes up when OpenAI's secondary price goes up. Robinhood hedges its exposure through SPVs that hold the actual shares — but doesn't guarantee a 1:1 hedge. OpenAI's response was blunt: "We did not partner with Robinhood, were not involved in this, and do not endorse it. Please be careful."
Tenev admitted the tokens aren't "technically" equity. But he argued they still give retail investors exposure to private assets they'd otherwise never touch.
Is this democratization or is this a derivative dressed up in a hoodie? Depends who you ask. But it tells you something about where this market is headed. When Robinhood is tokenizing secondary shares of companies that haven't consented to the process, you're a long way from Mike Jung buying Ask Jeeves options in the late '90s.
Both are growing. Fast.
The good, the bad, and the ugly
Ben: So what are some of the red flags to look out for when running a secondary?
For every well-run tender that keeps a team together, there's a cautionary tale about someone who got theirs and got out.
The good: Stripe allowed employees to participate in a secondary transaction while they've been noodling on an IPO for the better part of a decade. Employees got liquidity. The company kept building. That's the system working as designed.
The bad: Hopin founder Johnny Boufarhat sold over $100 million in shares across multiple rapid-fire fundraises. While founders selling during a raise isn't unusual, the pace was. The company raised so frequently that Boufarhat was able to sell nearly 17% of his stake before most people had figured out whether the product had staying power. The valuation eventually cratered.
The ugly: Pipe's management team took millions off the table in secondary sales — and then essentially group-quit. The people who were supposed to be strapping back in for another tour of duty cashed out and walked away. That's the nightmare scenario every board worries about.
And the really ugly: Adam Neumann. WeWork.
By 2019, Neumann had extracted $700 million from WeWork through a combination of stock sales and loans against his shares — all while the company was burning through $1.4 billion in cash with enough runway to last until mid-November. He sold $40 million in shares during one fundraise, then another $80 million in the next. When SoftBank invested $4.4 billion in 2017, Neumann unloaded $361 million more. He used the proceeds to buy five personal residences, invest in commercial real estate, and fund other startups. The company bought him a $63 million Gulfstream. He renovated his office with a sauna and an ice bath.
Meanwhile, WeWork had been profitable exactly once in its history — 2012, when it made $1.7 million.
When the S-1 finally dropped, the public markets saw what the private markets had been willing to ignore: massive losses, bizarre governance (Neumann's shares carried 20 votes each), and a founder who had been leasing his own buildings back to the company. The $47 billion valuation evaporated. The IPO was pulled. Neumann was forced out. And then SoftBank handed him a $1.7 billion exit package — $970 million for his shares, a $185 million consulting fee, and a $500 million credit line to repay his JPMorgan loans.
The company filed for bankruptcy in 2023.
Neumann became the cautionary tale that every VC now references when a founder asks to take more than $10 million off the table. Not because founder liquidity is inherently wrong. But because $700 million in personal liquidity from a company that had never figured out how to make money was a five-alarm signal that everyone chose to ignore.
These stories matter because they shape the rules. Every time a founder abuses secondary liquidity, boards tighten the restrictions for the next one. Every time an SPV blows up, companies add more transfer restrictions to their bylaws. The bad actors don't just hurt themselves — they make it harder for the people who actually need liquidity to get it.
The newest chapter: GP-led continuation vehicles
Ben: So where do we go from here? What’s next?
Everything we've talked about so far is the venture side of the story. Employees selling shares. Early investors finding a way out. Companies running tenders. But the biggest structural shift in the secondary market is happening one layer up — at the fund level.
A GP-led continuation vehicle works like this. A private equity firm owns a company inside a fund. The fund is ten years old. The company is performing. The GP doesn't want to sell it — they think there's more value to create. But their LPs need liquidity. The fund term is expiring. Pension funds have obligations. Endowments need to rebalance.
So the GP brings in a secondary buyer — someone like HarbourVest — to put together a transaction. The new buyer steps into the deal as an economic partner. The GP keeps running the company. And the original LPs get a choice: take your money off the table at this price, or roll into the new vehicle and keep riding.
Scott Voss at HarbourVest described it simply: it's a tender offer, but at the fund level. We're not selling the company. We're creating an option for new capital to step in and old capital to step out.
In 2025, the total secondary market hit $233 billion in volume — up 53% from the year before. GP-leds accounted for roughly half of that at $116 billion, with LP-led transactions at $117 billion. Five or six years ago, GP-leds barely existed in a mainstream form. TPG estimates that GP-led volume could grow to $300 billion or more over the next decade.
This isn't niche anymore.
And the scale of LP-side secondaries has grown just as fast. Yale sold a $3 billion portfolio into the secondary market. New York City did $6 billion. Ten years ago, the market couldn't have absorbed a deal that size. Now it's a Tuesday.
And it's the reason the secondary market isn't a temporary patch. It's becoming permanent infrastructure. Infrastructure eclipsing the public markets.
The whole game changed
Ben: It sounds like the secondary market solved a real problem and then immediately attracted everyone who wanted to monetize that solution. So how do you actually navigate it without getting taken?"
Secondaries are like any tool. You can build something great with them, or you can cut your finger off with a wet saw.
The market started because companies stayed private longer and employees needed a way to pay their mortgage with something other than a cap table entry. That problem was real. The solution — structured liquidity, company-sanctioned tenders, institutional secondary buyers — was real too.
But $233 billion in annual volume attracts everyone. The operators who care about retention and the grifters who care about fees. The GPs solving a genuine timing problem for their LPs and the ones marking their own homework. The firms sitting on the cap table and the ones selling SPVs out of a Gmail account.
The CFO's job is to know the difference.
If you're running a tender, set the guardrails tight. If you're buying secondary, understand the preference stack. If someone offers you a piece of a name-brand company with a 10% upfront commission and no disclosure on share class — close the email.
The secondary market isn't going away. It's the plumbing now. More volume than the IPO market. More innovation than most people realize. More risk than most people admit.
Use the tool. Just watch your fingers.
TL;DR: Medan Multiples are UP week over week.
The overall tech median is 3.2x (UP 0.3x w/w).
What Great Looks Like - Top 10 Medians:
EV / NTM Revenue = 15.3x (UP 1.2x w/w)
CAC Payback = 23 months
Rule of 40 = 50%
Revenue per Employee = $696k
Figures for each index are measured at the Median
Median and Top 10 Median are measured across the entire data set, where n = 144
Recent changes
Added: Navan, Bullish, Figure, Gemini, Stubhub, Klarna, Figma
Removed: Jamf, OneStream, Olo, Couchbase, Dayforce, Vimeo
Population Sizes:
Security & Identity = 17
Data Infrastructure & Dev Tools = 13
Cloud Platforms & Infra = 15
Horizontal SaaS & Back office = 17
GTM (MarTech & SalesTech) = 18
Marketplaces & Consumer Platforms = 18
FinTech & Payments = 28
Vertical SaaS = 17
Revenue Multiples
Revenue multiples are a shortcut to compare valuations across the technology landscape, where companies may not yet be profitable. The most standard timeframe for revenue multiple comparison is on a “Next Twelve Months” (NTM Revenue) basis.
NTM is a generous cut, as it gives a company “credit” for a full “rolling” future year. It also puts all companies on equal footing, regardless of their fiscal year end and quarterly seasonality.
However, not all technology sectors or monetization strategies receive the same “credit” on their forward revenue, which operators should be aware of when they create comp sets for their own companies. That is why I break them out as separate “indexes”.
Reasons may include:
Recurring mix of revenue
Stickiness of revenue
Average contract size
Cost of revenue delivery
Criticality of solution
Total Addressable Market potential
From a macro perspective, multiples trend higher in low interest environments, and vice versa.
Multiples shown are calculated by taking the Enterprise Value / NTM revenue.
Enterprise Value is calculated as: Market Capitalization + Total Debt - Cash
Market Cap fluctuates with share price day to day, while Total Debt and Cash are taken from the most recent quarterly financial statements available. That’s why we share this report each week - to keep up with changes in the stock market, and to update for quarterly earnings reports when they drop.
Historically, a 10x NTM Revenue multiple has been viewed as a “premium” valuation reserved for the best of the best companies.
Efficiency
Companies that can do more with less tend to earn higher valuations.
Three of the most common and consistently publicly available metrics to measure efficiency include:
CAC Payback Period: How many months does it take to recoup the cost of acquiring a customer?
CAC Payback Period is measured as Sales and Marketing costs divided by Revenue Additions, and adjusted by Gross Margin.
Here’s how I do it:
Sales and Marketing costs are measured on a TTM basis, but lagged by one quarter (so you skip a quarter, then sum the trailing four quarters of costs). This timeframe smooths for seasonality and recognizes the lead time required to generate pipeline.
Revenue is measured as the year-on-year change in the most recent quarter’s sales (so for Q2 of 2024 you’d subtract out Q2 of 2023’s revenue to get the increase), and then multiplied by four to arrive at an annualized revenue increase (e.g., ARR Additions).
Gross margin is taken as a % from the most recent quarter (e.g., 82%) to represent the current cost to serve a customer
Revenue per Employee: On a per head basis, how much in sales does the company generate each year? The rule of thumb is public companies should be doing north of $450k per employee at scale. This is simple division. And I believe it cuts through all the noise - there’s nowhere to hide.
Revenue per Employee is calculated as: (TTM Revenue / Total Current Employees)
Rule of 40: How does a company balance topline growth with bottom line efficiency? It’s the sum of the company’s revenue growth rate and EBITDA Margin. Netting the two should get you above 40 to pass the test.
Rule of 40 is calculated as: TTM Revenue Growth % + TTM Adjusted EBITDA Margin %
A few other notes on efficiency metrics:
Net Dollar Retention is another great measure of efficiency, but many companies have stopped quoting it as an exact number, choosing instead to disclose if it’s above or below a threshold once a year. It’s also uncommon for some types of companies, like marketplaces, to report it at all.
Most public companies don’t report net new ARR, and not all revenue is “recurring”, so I’m doing my best to approximate using changes in reported GAAP revenue. I admit this is a “stricter” view, as it is measuring change in net revenue.
OPEX
Decreasing your OPEX relative to revenue demonstrates Operating Leverage, and leaves more dollars to drop to the bottom line, as companies strive to achieve +25% profitability at scale.
The most common buckets companies put their operating costs into are:
Cost of Goods Sold: Customer Support employees, infrastructure to host your business in the cloud, API tolls, and banking fees if you are a FinTech.
Sales & Marketing: Sales and Marketing employees, advertising spend, demand gen spend, events, conferences, tools.
Research & Development: Product and Engineering employees, development expenses, tools.
General & Administrative: Finance, HR, and IT employees… and everything else. Or as I like to call myself “Strategic Backoffice Overhead.”
All of these are taken on a Gaap basis and therefore INCLUDE stock based comp, a non cash expense.
Please check out our data partner, Koyfin. It’s dope.
Wishing you trade at a high revenue and EBITDA multiple,
CJ














