Financial Commandment #1: Your Money, Your Responsibility
In this post you’ll learn: He almost didn’t review his tax return that year....
Every year, Bill D’Alessandro and I make predictions about where eCommerce is headed. Here are our 11 predictions for 2026, covering everything from AI-powered advertising to tariffs to the fate of lifestyle e-commerce brands.
Quick note on stakes: we got called out last year for being too generous, grading ourselves on our 2025 predictions. Fair criticism. So this year, we’re feeding the transcript into Claude and Grok at the end of 2026 and letting AI declare a winner.
Loser buys the winner a steak dinner. And feeds them the first bite. (Humiliations galore).
Here’s what I’m betting on:

Meta knows your interests. ChatGPT knows you’re afraid your business partner resents you, you’ve Googled “signs of burnout” four times this month, and you’re one bad quarter away from seriously considering selling.
When OpenAI launches ads, the targeting won’t just be precise. It will feel telepathic. Early movers win big.
Inflation is creeping up and economic growth looks soft. Trump responds to markets, and when the bond market freaked out earlier this year, tariffs got walked back fast. I don’t see him shooting a wounded economy when things are already shaky.
Counter to prevailing opinion here. The NASDAQ’s forward PE is around 27x right now. During the 2000 tech bubble, it was north of 100x. Government AI spending is also roughly 5x what tech spending was back in 2000, adjusted for inflation. The fundamentals look different this time.

I created a fresh X account recently and was shocked. Roughly a third of the videos in my feed looked AI-generated. Trust is eroding fast. I think we’ll see at least one major platform experiment with certifying content as human-created this year.
Descript can almost do this now. By year end, I think you’ll be able to drop raw footage into an AI, tell it what matters, and get a polished edit back. Scrappy founders will produce content that used to require a full production team.

Big tech and the Mag 7 continue to run, maybe up another 20%+, while the real economy and average consumer struggles. For eCommerce, Bill thinks you either need to go up-market selling to affluent consumers, or go down-market with sharp pricing on essentials. The middle is dangerous.
Bill sees no political will to cut spending, which means continued deficit spending, which means inflation. He thinks this is sticky for the next decade, not just 2026. His advice: position your portfolio and your business for a persistent inflationary environment.

Bill’s seen proof of concepts from big brands running pipelines that spit out 100 novel ads per day. AI reads reviews, pulls brand assets, generates stills and soon video, and launches directly through the API. He thinks 2026 is when this goes mainstream.
Unless you have strong IP protection or a top 5-10% brand, single-digit million eCommerce businesses are going to get crushed. Larger players building AI-powered machines will outspend you, out-test you, and tolerate higher CACs than you can.
Deals above $1B are up 19% year over year. Deals in the small and mid-size range dropped 18%. Bill thinks this continues: top-tier businesses will command eye-popping multiples, while typical eCommerce brands struggle to transact at all.
Bill sees competing pressures: a struggling consumer hurts Bitcoin as a risk asset, but inflation helps Bitcoin as digital gold. He thinks volatility comes first half of the year with a dip below $70K, then recovery as the inflation narrative takes hold.
You can listen to the full episode here.
When OpenAI launches ads, the targeting won’t just be precise. It will feel telepathic.
Predictions are fun, but they’re not your best bet for truly staying ahead of the curve.
What you really want is to plug into a braintrust of a thousand seven and eight-figure store owners who are discussing what’s working, what’s not, and what to expect going forward.
Join us inside the eComFuel community and learn from others like you in the trenches about what to expect this year.
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