Tactic
Be promiscuous with tax advisors, don't be loyal to one
Jess Mah says the biggest mistake people make with taxes is loyalty to a single inherited accountant. She instead talks to dozens of tax attorneys and accountants, tracks every idea they offer, and consolidates the best ones.
“And I think the mistake people make with taxes is they have their one tax person and that person worked with their parents and they've been loyal. But actually, this is a very bad place to have loyalty. It's really good to talk to— like, I've talked to dozens of tax—”
Steal thisPoll dozens of tax pros and friends for ideas, log every tactic, and consolidate the best instead of trusting one inherited accountant.
Number
Finance a $12M jet, write off the whole thing with $3M down
Jess Mah explains how accelerated depreciation lets you buy a $12M plane with ~$3M down, finance the rest, and write off the entire $12M against your tax bill the same year. The money leaves your account either way, so for high-earners a jet can be cheaper than the tax it offsets.
$12M
Price of private jet you can fully write off against taxes · USD
“So if you bought a $12 million airplane, financed it, you can write off the whole $12 million off your tax bill, even though you only put in $3 million. So you're going to pay the government or you could buy an airplane, right?”
Steal thisUse accelerated depreciation: finance a depreciable asset, put down a fraction, and write off the full purchase against income in the year you buy.
Framework
Rank ideas on three filters: hard to copy, cheap to start, recurring
When choosing her first company, Jess Mah scored every idea on a matrix: complicated enough that others won't copy fast, pseudo-bootstrappable on a couple million dollars, and recurring/sticky revenue. Business accounting scored best, which became Indinero.
“And so I literally went through every single one of those ideas on the Y Combinator list, and I rank ordered them based on these three criteria. And business accounting and tax management seemed to be the better one for my criteria.”
Steal thisScore every idea you're considering against three filters: hard to copy, cheap to start, and sticky recurring revenue.
Framework
Rank ideas on three filters: hard to copy, cheap to start, recurring
When choosing her first company, Jess Mah scored every idea on a matrix: complicated enough that others won't copy fast, pseudo-bootstrappable on a couple million dollars, and recurring/sticky revenue. Business accounting scored best, which became Indinero.
“And so I literally went through every single one of those ideas on the Y Combinator list, and I rank ordered them based on these three criteria. And business accounting and tax management seemed to be the better one for my criteria.”
Steal thisScore every idea you're considering against three filters: hard to copy, cheap to start, and sticky recurring revenue.
Idea
Doge as a Service: software that finds and fires the deadweight
Jess Mah pitches a platform that tracks whether employees are actually working — on Slack, email, their computer — and flags the quiet-quitters. Sell it through McKinsey/BCG to the CFO as a cost-cutting tool.
“So what if you could create a software platform that goes through and tracks who is actually on Slack, who is actually emailing, who is like using their computer? And if not, And then they're fired. So do it as a service for companies.”
Steal thisBuild a workforce-activity audit tool and sell it through consultants who already have the CFO relationship.
Idea
Vertical Agent-as-a-Service: a plug-and-play agent library per industry
Jess Mah predicts SaaS gives way to 'vertical ass' — pre-built libraries of AI agents tuned for one industry (dental offices, auto mechanics, manufacturers) so a business gets 100 baked-in workflows plug-and-play. She expects thousands of these and a Constellation-style rollup.
“Well, what if you could build vertical agent as a service for an industry? So for example, build a library of agents for dental offices or for auto mechanics, right? Or for, you know, clothing designers or manufacturers or whatever, or distributors. So there are all these industries, but where they need their own very unique library of agents to automate their tasks.”
Steal thisPick one industry you know, assemble off-the-shelf agents into a tuned plug-and-play library, and sell it as vertical agent-as-a-service.
Idea
Holy Health: band tiny medical providers together to win insurance
Inspired by a company minting tens of millions in EBITDA in 36 months by getting one niche of provider into insurance, Jess Mah's idea is to group small providers like chiropractors and physical therapists so they gain the scale to negotiate insurance reimbursement.
“I plugged this into ChatGPT, and I realized there's so many of these other types of people like chiropractors or physical therapists where they can get insurance reimbursement, but they're so small they don't have the, the scale to negotiate with an insurance company on getting reimbursed.”
Steal thisAggregate fragmented small providers so they collectively gain the scale to negotiate insurance reimbursement, then add agents and customer acquisition for lock-in.
Tactic
The one question that mines exotic, cash-minting businesses
Jess Mah's sourcing question isn't 'give me a business idea' — it's 'what's the most interesting, exotic business you've seen that's minting cash?' Then she interrogates the secret to its success, why nobody knows about it, why no one's copied it, and why now.
“What's the coolest, what's the most interesting, exotic business idea that's minting cash that you've seen recently. And so I'm not asking them for a business idea. I'm asking them for what's an existing thing you've seen?”
Steal thisAsk people for the most exotic cash-minting business they've seen, then probe why it works, why it's hidden, and why no one's copied it.
Story
Sequoia trained scouts on memos of great teams that still went to zero
As a Sequoia scout, Jess Mah voted on real startup memos with strong traction and teams, then learned the outcomes — many great-team companies went to zero because the idea itself was garbage. This convinced her that ideas matter as much as execution.
“And then they would ask us, would you invest on this memo? Yes or no? And so we would vote and then they'd say, well, here's what happened to that company. It ended up being, you know, a zero, even though it had the best team. The idea was still garbage.”
Framework
The Māui idea: free for the customer, sticky, hard to copy, self-funded
Jess Mah's bar for a great idea (her 'Māui' standard): it cash-flows without big outside funding, is boring/complicated enough that people won't copy it, and ideally the customer pays nothing upfront — you take a cut of the upside you create for them.
“It doesn't matter. Yeah, that's a great story. It's, it's about like how acute is this problem? And ideally, one hallmark of a Māui idea is the customer doesn't have to pay anything. So in Holy Health, you don't pay to be on our platform. By being part of our platform, you make more money, you get more customers, and we'll take a cut of that in exchange for helping you grow your business.”
Steal thisDesign offers where the customer pays nothing upfront and you take a cut of the new revenue you generate for them.
Story
The 'I feel like Bernie Madoff' email a year after YC
Jess Mah reads a 2011 email to her parents, a year after Y Combinator, admitting she felt like Bernie Madoff — rich on the outside, broken inside — with the company nine months from running dry. The raw note captures founder despair before she cut burn and clawed the company back.
“Subject line: Kind of sad. I feel like I'm Bernie Madoff, rich on the outside but completely broken on the inside. There's just a lot of pressure right now because the company is running dry on money in the next 9 or so months and we really need to produce this summer or else we're royally screwed.”
Take
Play to win, don't play not to lose
Jess Mah's core philosophy: a scarcity mindset (playing not to lose) measurably drops your IQ and kills creative thinking, while playing to win means optimism and a bit of delusion. You can't do the same thing and expect a different outcome.
“I think that came from this story that I just shared where I, one of my problems was I was playing not to lose. So I was in a scarcity mindset.. And when I'm running outta money and I'm in scarcity mindset, I mean, there's research that talks about how your IQ drops by a lot during those periods.”