A messy or missing cap table might not just slow you down, it could cost you your next fundraising round.
VCs get flooded with pitches, and if your equity is confusing or missing, they’ll move on fast.
Fidelity Private Shares is an all-in-one equity management platform that helps you maintain a clean cap table, an organized data room, and a clear equity story.
Comparing Marketplace Take Rates
People talk about take rates as if they’re pulled out of a hat. They’re not.
There are three characteristics I’ve identified that impact what you can (or rather, should) charge.
I make the distinction between can and should because there are absolutely examples of marketplaces who got greedy and ran themselves into the ground (see: Groupon).
Bill Gurley wrote the canonical piece on getting too aggressive, called “A Rake too Far”.
Take rate = f(x) of: Purchase frequency × ticket size × platform labor intensity
Estimates based on publicly available information as of January 2026
I. Insights from Research
The supply side always pays:
100% of the marketplaces I looked at charge the Supply (Seller) side
This makes sense, as they are bringing them business
The age old debate is whether this is net new business (making the pie bigger), or hijacking offline demand and just bringing it online
More than half of the marketplaces charge both sides of the transaction
Of the 25 marketplaces I dug into, 14 of 25 (or 56%) monetized both sides of the transaction.
For some of these marketplaces it more than doubles the total effective rake they earn
It’s less likely for the demand side to pay more than supply
Of the 14 that charged both sides, 3 charged the demand side more than the supply side
AirBnB
Stubhub
SeatGeek
And 1 charged the demand side at least 3x more
AirBnB
Some marketplaces may be going too far
“Earn up to less than half on your own work”
Shutterstock has long been criticized for the terrible unit economics it offers their photographers
Bill Gurley covered it nicely here in his piece “A Rake Too Far”
“High rakes are a form of friction precisely because your rake becomes part of the landed price for the consumer… In order for your platform to be the “definitive” place to transact, you want industry leading pricing – which is impossible if your rake is the de facto cause of excessive pricing. High rakes also create a natural impetus for suppliers to look elsewhere, which endangers sustainability.”
The following rental marketplaces are frequently criticized for their sell side fees
Airbnb (rental properties) - 15%, but there are many instances where it’s been much more after adding in all the extra fees (see below)
Vacasa (luxury, fully managed rental properties) - about double Airbnb but I guess more delux
Turo (luxury rental cars) - if you add insurance you can add 50% to the sticker rental price. But that’s really your choice (or requirement) as the driver
“Officer, I’d like to report a crime”
At the end of the day, the more work you do, the more juice you get
Dan Hockenmaier covered it nicely - there’s a spectrum of work and responsibility that’s taken on, and you are compensated accordingly
The 10% Range:
Amazon and Ebay are found on the far left on the “work” spectrum, generally serving as lead gen, and aggregating demand.
Another “light” example is Thumbtack: They charge the skilled worker a flat fee for the lead, ranging from $10 to $100, and then bounce, leaving it to the two sides to interact. They’re fully aware of the disintermediation that will inevitably occur when the plumber gives the home owner their business card on the way out, and therefore shaped their business model to contemplate this dynamic.
The 10% to 20% Range:
Somewhere in the middle you have the AirBnB’s and Etsy’s of the world who have generated trust on top of lead generation, making the transactions trustworthy and safe.
Another “managed” example would be StockX: They verify the authenticity of shoes before they send them to you, ensuring you don’t buy a fake pair of Jordans.
The 20% to 30% Range:
And then you have heavily managed marketplaces like DoorDash, Uber, and Lyft who went through the pains to build out entire logistic networks to serve the customer. This plays out in the take rate they’re able to charge.
Another “heavily managed” example would be Vacasa: They manage the properties on behalf of owners (toilet clogged?), unlike AirBnB who leaves it up to property owners to communicate with guests directly.
II. Ways to Increase Take Rate Overtime
From my research, marketplaces can increase take rate over time through “add ons” which make their existing service either:
Faster,
Deeper
Curated,
Ancillary,
Extra
Here are some real life examples:
TaskRabbit - Faster: TaskRabbit offers TaskRabbit Elite, a premium service that guarantees faster response times and provides dedicated support to users who require immediate assistance or have more complex tasks.
Etsy - Deeper: Apart from being a platform for handmade and vintage items, Etsy has introduced Etsy Plus, a subscription service offering sellers additional tools and customization options to improve their storefronts, marketing, and analytics.
Upwork - Curated: Beyond connecting freelancers and clients, Upwork offers services like Upwork Pro, which facilitates a more curated matchmaking process between top-tier freelancers and larger-scale projects. This premium service adds value by providing a higher level of expertise and support.
Airbnb - Ancillary: In addition to its core accommodation booking service, Airbnb has expanded into offering experiences, where hosts can provide unique activities and tours for travelers. This move adds value by curating personalized experiences for users beyond traditional lodging.
Turo - Extra: The peer-to-peer car rental marketplace offers a comprehensive insurance package for hosts and guests, providing peace of mind and addressing concerns related to vehicle damage and liability during rentals.
These additional services not only differentiate these platforms but also add significant value to users, fostering trust and loyalty within the marketplace ecosystem. Plus, from a financial perspective, they often have even better margins than the initial service being provided, adding to the bottom line.
I wrote more about this, which has been called The Marketplace Plus model.
I ran wicked far today
PR, no ER this year
One of the major benefits of working for myself now is having full control of my schedule. I set a goal to run a half marathon at sub 6 minute pace, and built the last 13 weeks around the training. Today we threw the ball deep and checked it off the bucket list. My favorite metric: 1:18:09 (5:58 pace). Washing down 25 munchkins never felt so good.
TL;DR: Medan Multiples are DOWN week over week.
The overall tech median is 4.0x (DOWN 0.4x w/w).
What Great Looks Like - Top 10 Medians:
EV / NTM Revenue = 15.8x (DOWN 0.3x w/w)
CAC Payback = 28 months
Rule of 40 = 47%
Revenue per Employee = $595k
Figures for each index are measured at the Median
Median and Top 10 Median are measured across the entire data set, where n = 146
Recent changes
Added: Navan, Bullish, Figure, Gemini, Stubhub, Klarna, Figma
Removed: Olo, Couchbase, Dayforce, Vimeo
Population Sizes:
Security & Identity = 17
Data Infrastructure & Dev Tools = 13
Cloud Platforms & Infra = 15
Horizontal SaaS & Back office = 19
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 a rational take rate,
CJ
