_{2026 BLIND DATES}

Who is Swiping Right on Who?

Last year around this time I did an M&A wishlist that turned out to have a pretty good call on it with WBD x Netflix. This year, I am doing something different by focusing on firms that have never publicly disclosed talks (except for one potential option) and seeing if these firms would be a good match. Once the summer slowdown is over, let’s see if any of these predictions can play out to be true going into year end.

Apple x Whoop

Apple Watch is a great product for people who want to know how many steps they took and hate any other stats because the battery will die in 15 minutes. Whoop is a great product for people who actually train.

The Whoop 5.0 tracks strain, recovery, sleep quality, HRV, and blood oxygen with a level of physiological depth that Apple Watch does not come close to, has a subscription model that generates recurring revenue, and has built a devoted following among serious athletes and military personnel who wear it as their primary health wearable. There are no buttons and there is no screen. It does one thing and it does it better than anything else on the market.

Apple has spent a decade trying to make Apple Watch a serious health device, and it keeps running into the same problem: it is also a notification machine and a payment terminal, which means it will never be trusted as a medical-grade sensor by anyone who cares about signal integrity.

Apple acquires Whoop, the hardware and sensor stack gets Apple silicon, and suddenly the Apple Health ecosystem has a product that your cardiologist and your marathon coach both take seriously.

While it doesn’t solve the Apple Watch’s biggest flaw - its battery life - it would provide some additional credibility to the Watch’s tracking metrics.

Whoop raised at a $3.6 billion valuation in 2021. It has not raised since. The founders have been running the company for thirteen years. The math on an Apple acquisition at $6-8 billion writes itself.

Whoop’s Dating Profile: Looking for someone with distribution, an App Store, and a decade of failing to build this in-house. Willing to overlook a history of dying at 3pm.

Odds of Successful Marriage: ~70%

SpaceX x Tesla

This one isn’t really a blind date. It’s more like matching with someone on Hinge that you grew up with and hoping they’ve been hit with the glow up stick. It’s also less of a marriage-by-choice and more an arranged marriage, but let’s take a look anyways.

Musk founded SpaceX in 2002 with his PayPal money, then led Tesla's Series A in early 2004 and took the chairman seat. By December 2008 both were weeks from running out of cash and he split what was left of his personal fortune between them. SpaceX later bought a quarter of a billion dollars of SolarCity bonds; Tesla bought SolarCity outright in 2016. Engineers have moved between the two for years, and they now share the Terafab project in Austin.

Elon Musk owns approximately 42% of SpaceX and roughly 13% of Tesla. He has spent the last three years building xAI, absorbing Cursor, buying stakes in Delivery Hero through X, and generally demonstrating that his preferred M&A strategy is to acquire things adjacent to things he already owns rather than build them from scratch.

SpaceX and Tesla are already adjacent in ways the market has not fully priced. Tesla’s energy storage business (Megapack, Powerwall) is the ground infrastructure for the same grid that SpaceX’s satellite network is powering from above.

Tesla’s manufacturing expertise in battery cells and electric drivetrains is directly applicable to SpaceX’s ambitions in electric propulsion and Starship recovery systems. Tesla’s Dojo supercomputer and its autonomous driving AI sit in the same compute stack as Grok.

The combination at current market caps would be worth somewhere north of $3 trillion. The governance is the obvious problem since Musk controls both, which makes any merger technically a related-party transaction that requires independent board approval on both sides. That process would be contentious. It would also be a near-certainty.

Tesla’s Dating Profile: $1.4 trillion market cap, autonomous driving AI, global manufacturing footprint, founder who also runs the rocket company. Looking for a formal relationship rather than continued informally shared management. Will require special committee approval.

Odds of Successful Marriage: ~80%. While this is an arranged marriage, it does require someone other than Elon to approve it. There is always a chance that someone with a morsel of independent thought decides to look at the numbers rather than just giving Elon the thumbs up.

Microsoft x Figma
Adobe tried to buy Figma for $20 billion in 2022 but ran into some regulatory problems. Figma went public instead in early 2026 and now trades at roughly a $16 billion market cap.

Microsoft has Copilot, Teams, PowerPoint, Word, and approximately $80 billion in cash. It does not have a design tool.

Every product team inside every enterprise that runs Microsoft 365 uses Figma to design things they then present in PowerPoint. That is an absurd workflow that exists only because Microsoft does not own the thing happening one step before PowerPoint.

Figma’s Dating Profile: Recently listed, design category leader, no enterprise sales team of its own. Looking for someone who already has 345 million commercial Microsoft 365 seats and wants to sell something into all of them.

Odds of Successful Marriage: ~50%. Adobe tried and the EU said no. Microsoft will argue it is a different buyer with a different competitive footprint, which is true. Whether Brussels agrees is the bet. It’s like having to ask your girlfriend’s estranged uncle for permission but he lives in a trailer park and you aren’t actually getting an inheritance benefit from being on his good side. If the EU clears it, this is a 10/10 strategic fit. If it doesn’t, Microsoft builds a worse version for five years and Figma stays independent.

Spotify x SiriusXM
Spotify has 777 million monthly users and 300 million subscribers, and after years of losses it finally prints money. What it doesn't have is growth in developed markets or an advertising business that works: ad-supported revenue grew 1% last quarter. SiriusXM has 33 million paid subscribers, a captive automotive audience, and has been bleeding subscribers since podcast listening moved to phones.

Together it’s the largest audio platform on earth with a paid subscriber base, an advertising network, podcast infrastructure, and a proprietary in-car distribution channel that Spotify has never had.

Separately, it’s one company with too many users and no profit and one with a contracting user base and a subscription model that belongs to a different era of commuting.

The deal structuring is not simple - Liberty Media owns the majority of SiriusXM - but Spotify has done harder things.

SiriusXM’s Dating Profile: Owns the car. Losing the phone. Looking for a partner with 600 million users and no opinion about Howard Stern.

Odds of Successful Marriage: ~40%. The strategic logic is sound, but Liberty Media’s ownership of SiriusXM makes the structure a nightmare; and Spotify has historically preferred to build rather than buy. If SiriusXM’s subscriber decline accelerates, this gets easier. Right now the price is too high for what is essentially a distribution asset.

JPMorgan x Robinhood
Robinhood has 28.4 million funded customers, the best retail brokerage app ever built, a gold subscription product growing at 40% year-on-year, and a market cap of ~$94 billion.

JPMorgan spent $1.2 billion building Chase Invest, which has fewer users and a worse app. It also spent $175 million acquiring Frank, the college financial aid startup, which turned out to be largely fabricated.

Robinhood is the only real entry point JPMorgan has into a generation of investors who have never walked into a branch and have no intention of starting. The problem is the price. HOOD trades at ~$94 billion, ~32% off its October 2025 peak, and a shareholder base that watched the stock hit $153.86 isn't tendering at $104.

Getting them there probably means a number north of $150 billion, nearly three times what JPMorgan paid for Bank One ($58 billion in 2004), and the largest deal in US banking since Citicorp and Travelers.

Jamie Dimon has called crypto “a pet rock” and Robinhood “a casino.” This deal would require him to own both. He would do it anyway, maybe.

Robinhood’s Dating Profile: 28 million users, great app, crypto exposure, no branches. Looking for a balance sheet. Not interested in being compared to a pet rock.

Odds of Successful Marriage: ~30%. JPM has the money (and advisory skills) to get the deal done, but there would likely be a culture clash between Robinhood and the traditional JPM teams. Additionally, Dimon would be forced to reverse his stance on the aforementioned issues, which isn’t impossible but isn’t likely. I would take more caution in integrating a start-up culture with an established banking culture.

Moonshot: SpaceX x TikTok (through X)
Elon Musk is a great builder. Look at PayPal, Tesla, and SpaceX. However, he is also not a stranger to buying into companies when he thinks he can improve them rather than build from scratch. He bought Twitter rather than building a social platform. He bought Cursor rather than training Grok to code.

X already has a payments infrastructure, a content delivery network, a 600 million user base, and a CEO who has been very public about wanting X to become the everything app, payments, commerce, video, AI, communication. The one thing X does not have is short-form video at scale. TikTok has 170 million US users, $100 billion in global GMV through TikTok Shop, and a forced divestiture from ByteDance that has been sitting in legal limbo for two years.

The national security argument that has blocked every other TikTok acquirer does not apply to Musk in the same way. He holds DoD contracts through SpaceX and Starshield. He ran DOGE. He has the kind of relationship with the current administration that makes a TikTok acquisition politically achievable in a way it has not been for any other buyer. ByteDance gets a clean exit north of $100 billion. X gets the short-form video engine it cannot build. SpaceX funds it, with maybe a little help from Daddy Elon.

The synergies between a satellite internet network, a social media platform, and a short-form commerce engine are real enough that you can model them. The probability that Musk is not already thinking about this is low.

TikTok’s Dating Profile: 170 million US users, $100 billion in GMV, legally complicated family situation, needs American owner urgently. Interested in someone with government connections, a satellite network, and a history of buying things rather than building them. Previous applicants need not reapply.

Odds of Successful Marriage: ~25%. Everything about the thesis is right and everything about the execution is chaotic. ByteDance will not sell cheaply. The DOJ will have opinions and Elon will have to stay on Trump’s good side through the review process. X’s balance sheet cannot absorb $100 billion without SpaceX writing the check. And Musk is already running five companies. But he has done crazier things and succeeded.

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Things I Wish I Knew as an Analyst

Look, I know most of you come here for deal rundowns and deep dives, but I am also cognizant that it is now the start of a new banking season on Wall Street. Training is likely nearing a close, or over already, and new first years are hitting the desk. Despite them saying they have always dreamed of being investment bankers in the interview, they probably have no idea what is going on.

The good news is I didn’t either, and now I write a newsletter, so anything is possible! On a more serious note, here are some things I wish I knew as a first year banker. I recommend pinning these next to your color pallet on your cubicle.

Use your brain.
It is easy to fall into the trap in banking of being a process monkey. Turn comments, quick review, send to associate, repeat. There will be a lot happening all at once and falling into a trap of just grinding blindly is easy. Using your brain is the single easiest way to avoid all of the issues listed below. If something seems directionally incorrect, spend an extra 5 minutes thinking about it. A great example of this is in the First Brand’s deal. Apollo passed on the deal because it couldn’t figure out how the SOCF and Income Statement tied out for the Company, something all of the lenders should have done, but didn’t. Taking the extra 5 minutes to think before doing saved them millions and actually allowed them to make some money buying CDS’s. 

The model is not the work.
Every analyst thinks the model is the deliverable. It is not. The model is the research tool. The deliverable is the judgment you form from running it. The most dangerous analysts I have seen are the ones who conflate precision in the model with correctness in the conclusion. A model that is technically flawless and built on a wrong assumption is worse than a rough model built on the right one, because the flawless model will be trusted and the rough one will be questioned. Question the assumptions before you polish the formatting. You can have the most technically perfect model, but if it doesn’t line up with the back of the envelope analysis your Director or MD will run, then it’s wrong… and chances are it’s not just because yours is more dynamic. The best deals are often not the over analyzed ones, but the ones that are able to pass the smell test early.

Your MD’s reputation is on the line every time you send an email.
When you send something out, it goes with your MD’s name on it, whether their name is on it or not. The culture of checking everything twice before it leaves the building is not bureaucracy. It is the only way people can afford to delegate, and being someone who can be delegated to without supervision is worth more than any technical skill you will develop in your first three years.

The first number out of your mouth becomes the anchor.
In any negotiation, any IC presentation, any client call where a valuation gets mentioned before you are ready, that number becomes the floor or the ceiling of the entire conversation regardless of what the analysis actually shows. Know your number before you walk in. If you don’t have one yet, say you don’t have one yet. “I’m still working through the analysis” is a complete sentence. “Somewhere around six to eight times” when you actually mean six is a number you will spend the rest of the meeting defending. If anything changes between versions of a model in any material way, then you will be constantly explaining why that delta exists.

Most deals fail for reasons that were visible on day one.
The diligence process is supposed to surface new information. It usually surfaces information that was already there but that nobody wanted to say out loud before the process started. The seller knew the customer concentration was a problem. The buyer suspected the management team was not as strong as the deck suggested. Both sides wanted the deal to happen, so nobody said anything until the lawyers found it at page 400 of the data room. The questions worth asking on day one are not the obvious ones. They are the questions that would embarrass someone to answer. Again, refer to the First Brands Story.

Being right early is the same as being wrong
For those of you who studied economics, this should be obvious, but it is hard to learn. As Keynes said: “the market can stay irrational longer than you can stay solvent.” You can have the correct view on a deal, a market, a company, or a trade and be completely wrong about the timing. In finance, those two things produce the same outcome. Being early on a thesis that eventually plays out is a story you tell at dinner, not a return you report to your LP. Time in a position costs capital. Conviction without a catalyst is a hobby.

Your network is the only thing that compounds faster than interest.
Not the LinkedIn kind. The kind where someone you worked with at 26 calls you at 36 because they trust you. Every person you treat with respect on the way up, every analyst you cover for, every associate you spend an extra hour helping at 11pm on a Thursday, that is the actual long-term investment portfolio. The deals change. The firms change. The people stay. There is nothing more valuable than being able to call a lender or a lawyer at the 11th hour and having them help you because they like working with you.

Nobody knows what they are doing as completely as they appear to.
The MD who walks into the room like he owns it has been winging significant portions of his career for thirty years and has simply gotten very good at looking like he is not. The VP who gives you feedback with perfect clarity worked out what she actually thought on the way to your desk. The partner who sounds certain has a model in his head built on assumptions he has never fully articulated. You are not uniquely underprepared. You are new. There is a difference.

Being 90% correct is the same as being 100% wrong.
This was something a professor told me in college, and I never forgot it. You spend most of your time in college fighting for partial credit on things, or hoping that not knowing the answer to one question is fine, because you know the rest. That’s not how the real world works. If your model is 90% correct but the mechanics in one spot are wrong, you are wrong. As scary as that sounds, the simplest way to fix it is just to remember to focus and double check everything before it goes out.