Want ADSK Stock 30% Cheaper? Get Paid 12% While You Wait

Collect a healthy income stream from Autodesk now, that you keep no matter what, while lining up a chance to own this software giant at a serious discount if its big new bet creates a little turbulence.

Autodesk (ADSK) has been a frustrating stock to own, trailing the broader market while trading near $237.38 a share. Now, the company is making its biggest bet ever, announcing the “largest deal we’ve ever done” to acquire a company. For investors intrigued by the long-term story but wary of the short-term turbulence, this creates an interesting setup for an income-generating trade.

12% annualized yield at a 30% margin of safety, by selling put options.

• Sell a put option on ADSK expiring 6/17/2027, with a strike price of $165.
• Collect roughly $995 in premium per contract (each contract covers 100 shares).
• That works out to about 6.8% annualized on the $16,500 of cash you set aside to secure the trade.
• Park that cash in a money market or savings account earning roughly 5.0%, and your total yield climbs to about 11.8%.
• And if ADSK falls below $165, you buy it at $165, an effective entry near $155.05 a share after the premium, about a 35% discount to today’s $237.38.

Two Ways This Plays Out, Both Pay You

If ADSK stays above $165 through 6/17/2027, the put expires worthless and you simply keep the full $995 premium. That is about 6.0% on the $16,500 you set aside over 324 days, while that same collateral keeps earning the ~5.0% money-market yield on top, for the ~11.8% total above. You never buy the stock and keep the income, free to do it again.

If ADSK closes below $165, you are assigned and buy 100 shares at $165. The $995 premium you already pocketed lowers your effective cost to about $155.05 a share, roughly a 35% discount to today’s price, though if the stock has fallen further by then you would be holding a paper loss.

So what happens if ADSK really does close below $165, and you are the one buying? Then everything rests on a single question.

How Comfortable Would You Be Holding ADSK?

So, would you be comfortable owning this business at a significant discount to today’s price? That’s the only question that matters. On one hand, Autodesk is running a proven playbook. Management points to its success in construction, where it spent about “$1.8 billion on acquisitions” over 5 years to build a business now doing “almost $600 million in revenue” and “growing north of 20%.” The plan is to do it again in the operations software market, which the company believes will unlock the addressable market and complete its strategic vision to connect the entire “design, make, operate” lifecycle. The core business appears solid, with management reporting “strong Q1 fiscal ’27 results” and having “raised our revenue guidance.”

On the other hand, this is a massive undertaking fraught with risk. Skeptics see a company paying a steep price, one analyst pegged it at “18x next year’s revenue”, at a time when other large software M&A deals have struggled. This major integration is happening while Autodesk is also executing a significant sales reorganization. Channel checks have surfaced talk of “a degree of disruption,” and management itself acknowledged it saw exactly the kind of weak performance it expected as the changes rolled out. While headline numbers look good, some underlying metrics like remaining performance obligation, with “RPO growth of 9%,” have been a bit slower, which the company attributes to a deliberate move away from multiyear contract discounts.

Ultimately, the trade is a bet that you are being well-paid to take on that execution risk. You collect your income upfront, and if the stock holds up, that’s your return. If the skeptics are right and the stock falls, you become an owner of a business you wanted, but at a much better price. For a deeper look at what could drive the stock from here, it is worth exploring the potential catalysts. The thing to watch is how quickly that new business performance recovers from the sales force changes; that will be the clearest sign of whether the company has the operational capacity to digest its largest acquisition yet.

Wondering whether another stock offers a better yield, or what this same trade would pay on a name you already like? You can screen the latest cash-secured put yields across the market for yourself. And if it is exposure to Nasdaq as a whole you want rather than this one name, a Nasdaq ETF like QQEW covers it. Going broader than any one sector, to a quality-first mix across the whole market, is where the portfolio below comes in.

Before You Commit To Buying More Of One Stock, Know How Much You Already Carry

A put sale is a promise to add to a single name, and the first thing a professional checks before that promise is existing exposure, because concentration is what turns an income trade into an oversized bet. That check is exactly what the Trefis Wealth team provides, with the same rules-based systematic discipline that runs our High Quality Portfolio. Request a free vulnerability audit of your biggest positions.