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The startup betting AI can unlock a new era of ‘found money’ for enterprises

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It’s a paradigm perhaps most commonly discussed in the context of the Innovator’s Dilemma—academic Clayton Christensen’s influential thesis around how large incumbent companies become too tied to existing customers and processes, and ultimately lose market share to competitors. To Tony Capasso, this framework carries through to the financial lifeblood of any business: revenue. 

He says that, like product and engineering orgs, sales teams can “get stuck on the same golden goose of their product and revenue stream.” Over time, it gets harder to allocate resources to new opportunities, even if they’re crystal clear. 

“Part of what that looks like is not having enough people,” said Capasso. “All my people are busy, and they’re all working on the core stuff. There may be new things they’re not trained on or that are hard to learn. And ultimately that’s what leads to risk. It’s the opportunity cost to pull someone off something core to work on something new. That’s the revenue dilemma. It’s asking: How do we expand our possibilities and go places we’re not currently going, without disrupting the whole machine?”

Capasso—who played professional soccer (and coached at UT Austin) before moving into sales and revenue leadership at Austin-based startups like Bazaarvoice—believes AI is uniquely equipped to help sales teams “find money” by automating sales interactions.

“I want to challenge the assumption that we need to put a human in the middle of everything for a user to get great benefit from that,” he told Fortune. “I think there are actually a lot of interactions where the user would prefer not to talk to a human… It’s not about perfection. It’s about getting that user what they need in the moment.”

Capasso started OnProfit in 2024 with Alan Lockett, David Rubin, and Matt Stuart to build AI tools that unlock “found money”—revenue that is currently being left on the table due to unexecuted initiatives, underutilized products, or gaps in sales and customer coverage. Today, the Austin-based company is emerging from stealth, with a roster of customers currently including HomeStory, OEConnection, and Commerce. OnProfit is backed by Lerer Hippeau, SignalFire, and Mark VC, from whom it quietly raised a seed round in 2024. (It declined to disclose the amount raised.)

“We’re focused on enterprises because fundamentally, they’re the biggest opportunities for this found revenue, found money,” said Capasso. “Our value proposition is where there’s a built-in coverage problem, a mismatch between opportunity and the resources to go after that opportunity.”

HomeStory president Chad Bockius has wrestled with this, working to optimize the real estate brokerage platform’s sales funnel. It’s essentially impossible to set up a system where no customer falls through the cracks at the vulnerable beginning of a sales process. 

“I know I’m leaving money on the table, but the economics don’t work,” said Bockius. “I just can’t hire enough people to solve that problem. So, I just lived with it and hated that metric.”

Bockius, who hired Capasso for his first sales job, said that using OnProfit’s platform has led to a “10% improvement in that… connection rate, and…that translates into about a 20% increase in revenue down at the end.”

It’s not even that most revenue teams are doing anything wrong—it’s just that the basics of sales and revenue management require a lot of coordination. Jim Stoneham, SignalFire partner and former New Relic head of growth, said the revenue dilemma was his life for years.  

“Lots of revenue teams are just trying to keep the basics working well, a revenue cycle coming up, an upgrade opportunity tied to a new product release,” said Stoneham, also Stripe’s former CMO. “These seem trivial…but they typically aren’t. You need to get ten people in a room to make anything happen.”

There’s no shortage of potential competitors in the space (essentially everyone applying AI to the revenue and sales stacks). While AI may be the answer, at its core, these are not problems that can be solved solely with tech, said Adam Zeplain, Mark VC cofounder and managing partner. 

“These are business problems,” he said. “These are not technical problems. You need to understand exactly the business problems these companies need to solve. It’s all the same technology, but there are no one-size-fits-all solutions.”

When I see Capasso, he’s got OnProfit swag that doesn’t feature the company name. Instead, the hat says “Found Money Club.” And that’s intentional. 

“Who doesn’t want to join the Found Money Club?” Capasso laughs. 

See you tomorrow,

Allie Garfinkle
X:
@agarfinks
Email:alexandra.garfinkle@fortune.com
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VENTURE DEALS

ProtegoBiopharma, a San Diego, Calif.-based developer of therapies for protein folding diseases, raised $130 million in Series B funding. NovartisVentureFund and Forbion led the round and were joined by OmegaFunds, DroiaVentures, YKBioventures, and others.

Sokin, a London, U.K.-based payments firm, raised $50 million in Series B funding. PrysmCapital led the round and was joined by WatershedVentures and others. 

Nevis, a New York City-based developer of AI tools for wealth management firms, raised $35 million in Series A funding from ICONIQ, SequoiaCapital, and RibbitCapital.

TutorIntelligence, a Watertown, Mass.-based provider of AI-powered robot workers, raised $34 million in Series A funding. UnionSquare Ventures led the round and was joined by others.

Raindrop, a San Francisco-based monitoring platform for AI agents, raised $15 million in seed funding. LightspeedVenturePartners led the round and was joined by FigmaVentures, VercelVentures, and others.

JeevaAI, a San Francisco-based AI-powered platform designed to make sales teams more productive, raised $9 million in funding. JLLSpark led the round and was joined by SapphireVentures, AltCapital, and others.

MetriBio, a Boston, Mass.-based developer of therapies for endometrial diseases, raised $5 million in pre-seed funding. PillarVC led the round and was joined by PaceVentures and others.

Private Equity

Stonepeak and EnergyEquationPartners acquired a 65% stake in JET, a London, U.K.-based fuel retailer, from Phillips66 for approximately €2.5 billion ($2.9 billion).

PayRange, backed by RidgeviewPartners, acquired KiosoftTechnologies, a Boynton Beach, Fla.-based cashless payment platform. Financial terms were not disclosed.

The Goldman Sachs Group agreed to acquire Innovator Capital Management, a Wheaton, Ill.-based active ETF sponsor. Financial terms were not disclosed.



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Trump wants more health savings accounts. A catch: they can’t pay insurance premiums

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With the tax-free money in a health savings account, a person can pay for eyeglasses or medical exams, as well as a $1,700 baby bassinet or a $300 online parenting workshop.

Those same dollars can’t be used, though, to pay for most baby formulas, toothbrushes — or insurance premiums.

President Donald Trump and some Republicans are pitching the accounts as an alternative to expiring enhanced federal subsidies that have lowered insurance premium payments for most Americans with Affordable Care Act coverage. But legal limits on how HSAs can and can’t be used are prompting doubts that expanding their use would benefit the predominantly low-income people who rely on ACA plans.

The Republican proposals come on the heels of a White House-led change to extend HSA eligibility to more ACA enrollees. One group that would almost certainly benefit: a slew of companies selling expensive wellness items that can be purchased with tax-free dollars from the accounts.

There is also deep skepticism, even among conservatives who support the proposals, that the federal government can pull off such a major policy shift in just a few weeks. The enhanced ACA subsidies expire at the end of the year, and Republicans are still debating among themselves whether to simply extend them.

“The plans have been designed. The premiums have been set. Many people have already enrolled and made their selections,” Douglas Holtz-Eakin, the president of the American Action Forum, a conservative think tank, warned senators on Nov. 19. “There’s very little that this Congress can do to change the outlook.”

Cassidy’s Plan

With health savings accounts, people who pay high out-of-pocket costs for health insurance are able to set aside money, without paying taxes, for medical expenses.

For decades, Republicans have promoted these accounts as a way for people to save money for major or emergent medical expenses without spending more federal tax dollars on health care.

The latest GOP proposals would build on a change included in Republicans’ One Big Beautiful Bill Act, which makes millions more ACA enrollees eligible for health savings accounts. Starting Jan. 1, those enrolled in Obamacare’s cheapest coverage may open and contribute to HSAs.

Now Republicans are making the case that, in lieu of the pandemic-era enhanced ACA subsidies, patients would be better off being given money to cover some health costs — specifically through deposits to HSAs.

The White House has yet to release a formal proposal, though early reports suggested it could include HSA contributions as well as temporary, more restrictive premium subsidies.

Sen. Bill Cassidy — a Louisiana Republican who chairs the Senate Health, Education, Labor, and Pensions Committee and is facing a potentially tough reelection fight next year — has proposed loading HSAs with federal dollars sent directly to some ACA enrollees.

“The American people want something to pass, so let’s find something to pass,” Cassidy said on Dec. 3, pitching his plan for HSAs again. “Let’s give power to the patient, not profit to the insurance company.”

He has promised a deal can be struck in time for 2026 coverage.

Democrats, whose support Republicans will likely need to pass any health care measure, have widely panned the GOP’s ideas. They are calling instead for an extension of the enhanced subsidies to control premium costs for most of the nearly 24 million Americans enrolled in the ACA marketplace, a larger pool than the 7.3 million people the Trump administration estimates soon will be eligible for HSAs.

HSAs “can be a useful tool for very wealthy people,” said Sen. Ron Wyden of Oregon, the top Democrat on the Senate Finance Committee. “But I don’t see it as a comprehensive health insurance opportunity.”

Who Can Use HSAs?

The IRS sets restrictions on the use of HSAs, which are typically managed by banks or health insurance companies. For starters, on the ACA marketplace, they are available only to those with the highest-deductible health insurance plans — the bronze and catastrophic plans.

There are limits on how much can be deposited into an account each year. In 2026 it will be $4,400 for a single person and $8,750 for a family.

Flexible spending accounts, or FSAs — which are typically offered through employer coverage — work similarly but have lower savings limits and cannot be rolled over from year to year.

The law that established HSAs prohibits the accounts from being used to pay insurance premiums, meaning that without an overhaul, the GOP’s proposals are unlikely to alleviate the problem at hand: skyrocketing premium payments. Obamacare enrollees who receive subsidies are projected to pay 114% more out-of-pocket for their premiums next year on average, absent congressional action.

Even with the promise of the government depositing cash into an HSA, people may still opt to go without coverage next year once they see those premium costs, said Tom Buchmueller, an economics professor at the University of Michigan who worked in the Biden administration.

“For people who stay in the marketplace, they’re going to be paying a lot more money every month,” he said. “It doesn’t help them pay that monthly premium.”

Others, Buchmueller noted, might be pushed into skimpier insurance coverage. Obamacare bronze plans come with the highest out-of-pocket costs.

An HHS Official’s Interest

Health savings accounts can be used to pay for many routine medical supplies and services, such as medical and dental exams, as well as emergency room visits. In recent years, the government has expanded the list of applicable purchases to include over-the-counter products such as Tylenol and tampons.

Purchases for “general health” are not permissible, such as fees for dance or swim lessons. Food, gym memberships, or supplements are not allowed unless prescribed by a doctor for a medical condition or need.

Americans are investing more into these accounts as their insurance deductibles rise, according to Morningstar. The investment research firm found that assets in HSAs grew from $5 billion 20 years ago to $146 billion last year. President George W. Bush signed the law establishing health savings accounts in 2003, with the White House promising at the time that they would “help more American families get the health care they need at a price they can afford.”

Since then, the accounts have become most common for wealthier, white Americans who are healthy and have employer-sponsored health insurance, according to a report released by the nonpartisan Government Accountability Office in September.

Now, even more money is expected to flow into these accounts, because of the One Big Beautiful Bill Act. Companies are taking notice of the growing market for HSA-approved products, with major retailers such as Amazon, Walmart, and Target developing online storefronts dedicated to devices, medications, and supplies eligible to be purchased with money in the accounts.

Startups have popped up in recent years dedicated to helping people get quick approval from medical providers for various — and sometimes expensive — items, memberships, or fitness or health services.

Truemed — a company co-founded in 2022 by Calley Means, a close ally of Health and Human Services Secretary Robert F. Kennedy Jr. — has emerged as one of the biggest players in this niche space.

A $9,000 red cedar ice bath and a $2,000 hemlock sauna, for example, are available for purchase with HSA funds through Truemed. So, too, is the $1,700 bassinet, designed to automatically respond to the cries of a newborn by gently rocking the baby back to sleep.

Truemed’s executives say its most popular products are its smaller-dollar fitness offerings, which include kettlebells, supplements, treadmills, and gym memberships.

“What we’ve seen at Truemed is that, when given the choice, Americans choose to invest their health care dollars in these kinds of proven lifestyle interventions,” Truemed CEO Justin Mares told KFF Health News.

Means joined the Department of Health and Human Services in November after a stint earlier this year at the White House, where he worked when Trump signed the One Big Beautiful Bill Act into law in July. Truemed’s general counsel, Joe Vladeck, said Means left the company in August.

Asked about Means’ potential to benefit from the law’s expansion of HSAs, HHS spokeswoman Emily Hilliard said in a statement that “Calley Means will not personally benefit financially from this proposal as he will be divesting from his company since he has been hired at HHS as a senior advisor supporting food and nutrition policy.”

Truemed is privately held, not publicly traded, and details of how Means will go about divesting have not been disclosed.

KFF Health News is a national newsroom that produces in-depth journalism about health issues and is one of the core operating programs at KFF — the independent source for health policy research, polling, and journalism.



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Netflix lines up $59 billion of debt for Warner Bros. deal

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Netflix Inc. has lined up $59 billion of financing from Wall Street banks to help support its planned acquisition of Warner Bros. Discovery Inc., which would make it one of the largest ever loans of its kind.

Wells Fargo & Co., BNP Paribas SA and HSBC Plc are providing the unsecured bridge loan, according to a statement Friday, a type of financing that is typically replaced with more permanent debt such as corporate bonds.

Under the deal announced Friday, Warner Bros. shareholders will receive $27.75 a share in cash and stock in Netflix. The total equity value of the deal is $72 billion, while the enterprise value of the deal is about $82.7 billion.

Bridge loans are a crucial step for banks in building relationships with companies to win higher-paying mandates down the road. 

A loan of $59 billion would rank among the biggest of its type, Anheuser-Busch InBev SA obtained $75 billion of loans to back its acquisition of SABMiller Plc in 2015, the largest ever bridge financing, according to data compiled by Bloomberg.



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Stocks: Facing a vast wave of incoming liquidity, the S&P 500 prepares to surf to a new record high

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The S&P 500 index ticked up 0.3% yesterday, its eighth straight upward trading session. It is now less than half a percentage point away from its record high, and futures were pointing marginally up again this morning. Nasdaq 100 futures were even more optimistic, up 0.39% before the open in New York. The VIX “fear” index (which measures volatility) has sunk 12.6% this month, indicating that investors seem to have settled in for a calm, quiet, risk-on holiday season.

They have reason to be happy. Washington is preparing a wave of incoming liquidity that is likely to generate fresh demand for equities.

For instance, the CME FedWatch index shows an 87% chance that the U.S. Federal Reserve will deliver an interest rate cut next week, delivering a new round of cheaper money. Further cuts are expected in 2026.

Furthermore, Wall Street largely expects President Trump to announce that Kevin Hassett will replace Fed chairman Jerome Powell in May—and Hassett is widely regarded as a dove who will lean in favor of further rate cuts.

Elsewhere, the Fed has begun a series of “reserve management purchases,” a program in which the central bank will buy short-term T-bills—a move that will add more liquidity to markets generally.

Banks, brokers and trading platforms are also lining up to handle ‘Trump Accounts,’ into which the U.S. government will deposit $1,000 for every child. The trust fund can be invested in low-cost stock index trackers—a new source of investment demand coming online in the back half of 2026.

So it’s no surprise that nine major investment banks polled by the Financial Times expect stocks to rise in 2026; the average of their estimates is by 10%.

The Congressional Budget Office also estimates that the One Big Beautiful Bill Act will add 0.9% to U.S. GDP next year largely because it allows companies to immediately deduct capital expenditures from their taxes—spurring a huge round of corporate spending. 

With all that fresh money on the horizon, it’s clear why markets have shrugged off their worries about AI and Bitcoin. The only shock will be if the S&P fails to hit a new all-time high by the end of the year.

Here’s a snapshot of the markets ahead of the opening bell in New York this morning:

  • S&P 500 futures were up 0.2% this morning. The last session closed up 0.3%. 
  • STOXX Europe 600 was up 0.3% in early trading. 
  • The U.K.’s FTSE 100 was up 0.14% in early trading. 
  • Japan’s Nikkei 225 was up 2.33%. 
  • China’s CSI 300 was up 0.34%. 
  • The South Korea KOSPI was down 0.19%. 
  • India’s NIFTY 50 is up 0.18%. 
  • Bitcoin was flat at $93K.



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