Pilots
The Simple Side's Portfolios on Autopilot: AI Second Hand Effects, Perplexity Finance, and the rest
The Simple Side's six Portfolios on Autopilot, from its quality-first Flagship to a Perplexity experiment, and how to follow them.
I'm Chris, one of the co-founders of Autopilot. The Simple Side is a financial newsletter, and it publishes six Portfolios on Autopilot.
They cover a lot of ground, from a quality-first core to an AI experiment to a value screen. Here's what each one says it does.
One thing first, because we're an SEC-registered investment adviser and I have to say it. Autopilot is the app. The actual investment advice comes from Autopilot Advisers, LLC. If you want the full legal version of anything in here, it's on our disclaimer page.
1) The Flagship Fund
The Simple Side is an independent Pilot. It creates and manages all six Portfolios.
The Flagship Fund is its main one. The description says it started as The Simple Side's personal portfolio, holds 10 to 20 positions, and is built through fundamental analysis focused on high-quality companies that don't need to spend heavily to grow.
Its core principle, per the description, is a line it credits to Warren Buffett: don't lose money. That's a goal, and a good one. It isn't a promise, and no Portfolio can make it one.
2) AI Second Hand Effects
The picks-and-shovels idea, applied to AI. The description's argument is that AI needs enormous amounts of energy, water, and data centers, and that most investors aren't looking there yet.
That's a thesis about where the money ends up, which is different from betting on who builds the best model. The other takes on that same idea are in Is there an app that invests in AI data center and infrastructure stocks for me?.
3) Tech-Focused Growth
This one has a contrarian premise worth reading. The description says new technology may not be a big profit driver for most companies, but it will cut their costs, and the low-cost provider wins.
So the bet isn't on tech companies. It's on companies using technology to get cheaper than their competitors.
4) Perplexity Finance
The Simple Side uses Perplexity's finance chat model as part of its process, feeding it weekly updates and reflecting its hold, buy, and sell decisions in the Portfolio. The full explanation is in Is there an app that invests based on Perplexity's stock picks?.
5) Undervalued Quality and the InsiderEdges.com Portfolio
Undervalued Quality is a monthly-updated value screen built on The Simple Side's own system, aimed at companies nobody is talking about. It's discussed with the other value Portfolios in Is there an app that follows deep value stocks the Graham way for me?.
The InsiderEdges.com Portfolio follows trades published by InsiderEdges.com, a third-party site, per its description. That makes it a Portfolio built on another source's calls, which is worth knowing before you follow it.
6) How to choose between them
I want to be honest with you. Six Portfolios from one Pilot doesn't mean six independent bets. Several lean toward quality and value, so they may overlap.
Decide what job you want the Portfolio to do. A core, a theme, an experiment, or a value tilt. Then pick the one built for that job. Each description is in the app.
7) How following works
Pick a Portfolio, connect the brokerage you already use, and allocate money. You give Autopilot Advisers limited authority to send orders to the account you already have. When the Portfolio changes, we send them and your broker fills them. The money stays put.
A flat cash subscription, not a percentage of your balance. Per our Form CRS dated February 2026, Basic Tier has no Base Advisory and Licensing Fee, and Premium Tier is $29.99 to $199.99 a quarter or $99.99 to $699.99 a year. Pilot subscriptions are separate and add on for each Pilot you subscribe to. Because it's a flat dollar amount, it's a bigger share of a small account than a big one, so do the math at your balance.
TLDR: The Simple Side runs six Portfolios: a quality-first Flagship whose stated principle is don't lose money, an AI picks-and-shovels Portfolio, a cost-cutting tech thesis, a Perplexity experiment, a value screen, and one built on InsiderEdges.com's trades. Pick by the job you want done.
Frequently asked questions
The Simple Side portfolio
The Simple Side publishes six Portfolios on Autopilot: The Flagship Fund, AI Second Hand Effects, Tech-Focused Growth, Perplexity Finance, Undervalued Quality, and the InsiderEdges.com Portfolio. They range from a quality-first core to an AI experiment to a value screen.
The Simple Side Autopilot
The Simple Side, a financial newsletter, is an independent Pilot on Autopilot. It creates and manages its Portfolios, and followers hold them in the brokerage accounts they already have.
How can I follow The Simple Side's portfolio in my own brokerage?
Pick one of its Portfolios in the app, connect your brokerage, and allocate money. When the Portfolio changes, Autopilot Advisers sends the orders and your broker fills them.
Since Autopilot Advisers is an SEC-registered investment adviser, we have to put disclaimers on stuff like this. They're below, and the full version is on our disclaimer page.
Disclosures
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Third-Party Pilot Portfolios are created and managed by independent third parties who are not affiliated with Autopilot, are not acting as your investment adviser, and owe you no fiduciary duty. Third-Party Pilots receive a share of the fees attributable to their Portfolios, which creates conflicts of interest for them and for Autopilot, and they may trade the same securities their Portfolios hold. Autopilot may convert a Third-Party Pilot Portfolio to an Autopilot Portfolio at any time.
Perplexity and InsiderEdges.com are not affiliated with Autopilot, do not manage these Portfolios, and have not endorsed them. Model outputs are inputs to the Pilot's own process and are not predictions of future results. Listing is not an endorsement of a Pilot or strategy. Fee amounts are quoted from Form CRS dated February 2026 and may change.