Want ADSK Stock 30% Cheaper? Get Paid 11% A Year While You Wait

Here is a way to collect an attractive income stream right now that you keep no matter what, while lining up a chance to buy a top-tier software franchise at a significant discount if it ever gets cheap.

Autodesk (ADSK) has been a tale of two tapes: the stock has underperformed the S&P 500 over the last year and currently trades about 23% below its 52-week high, yet the company just made its largest acquisition ever. That combination of a lagging stock price and a major strategic move creates an interesting setup for an investor who is willing to be patient, and get paid for it.

11% annualized yield at a 30% margin of safety, by selling put options.

• Sell a put option on ADSK expiring 9/17/2027, with a strike price of $175.
• Collect roughly $1,295 in premium per contract (each contract covers 100 shares).
• That works out to about 6.8% annualized on the $17,500 of cash you set aside to secure the trade.
• Park that cash in Treasury bills or a Treasury money-market fund yielding roughly 3.9%, and your total yield climbs to about 10.7%.
• And if ADSK falls below $175, you buy it at $175, an effective entry near $162.05 a share after the premium, about a 36% discount to today’s $251.29.

Two Ways This Plays Out, Both Pay You

If ADSK stays above $175 through 9/17/2027, the put expires worthless and you simply keep the full $1,295 premium. That is about 6.8% annualized on the $17,500 you set aside over 394 days, while that same collateral keeps earning the ~3.9% T-bill yield on top, for the ~10.7% total above. You never buy the stock and keep the income, free to do it again.

If ADSK closes below $175, you are assigned and buy 100 shares at $175. The $1,295 premium you already pocketed lowers your effective cost to about $162.05 a share, roughly a 36% 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 $175, 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 if you were asked to buy it at a discount to today’s price? It’s a question of ambition versus execution. On one hand, Autodesk is playing a long game, and its recent acquisition of MaintainX is a prime example. Management is following a playbook that proved highly successful in construction, where it spent about $1.8 billion on acquisitions over five years to build a business now generating almost $600 million in annual revenue and growing north of 20%. The goal now is to replicate that success in the operations market, which the company believes will eventually unlock a new addressable market for them. This isn’t a company in distress; it just delivered strong Q1 results and raised its full-year revenue and margin guidance.

On the other hand, the risks are not trivial, and they are precisely what could push the stock lower. This is the “largest deal we’ve ever done,” and it comes at a time when the company is already navigating a major sales reorganization. As one analyst noted, large M&A in the software space “hasn’t exactly gone well” for other companies recently. That internal restructuring is already causing what channel checks call “a degree of disruption.” Management acknowledges this, stating they “saw exactly the kind of weak new performance we expected” as the changes were implemented. While the company’s long-term strategy may be sound, you can explore a deeper analysis of whether Autodesk is safer than it was a year ago to gauge the current risk profile.

Ultimately, this trade is a bet on your own conviction. If you believe the strategic expansion is a smart long-term move, you get paid to wait for the story to play out, with a built-in margin of safety. If the execution risks do materialize and weigh on the stock, you become an owner at a price you found attractive from the start. The one thing to watch is new subscription growth. Management said the recent weakness was within its range of expectations. If that metric stabilizes and improves in the coming quarters, it suggests the disruption is fading. If it remains soft, the bears have a stronger case.

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 that single sector. Going broader than any one sector, to a quality-first mix across the whole market, is where the portfolio below comes in.

Where This Trade Fits A Bigger Plan

Selling a cash-secured put is a smart way to manufacture income now and engineer a cheaper entry on a stock you have actually researched. The catch sits in the trade itself: it is a single name, and if that name falls hard you are the one left holding it. It is a good tool, not a whole portfolio.

That is where the Trefis High Quality (HQ) Portfolio comes in. It pairs the kind of active idea you just read about with a hands-off core of about 30 quality businesses, each chosen on the full weight of its fundamentals rather than a single setup, then sized and re-balanced with discipline. The result is a track record of outpacing a benchmark that combines the three major indices – the S&P 500, S&P Mid-cap, and Russell 2000. Run trades like this on top of a foundation that is not riding on any one of them.