Welcome back to Forests Over Trees, your tech strategy newsletter. It’s time to zoom-out, connect dots, and (try to) predict the future.

Quick reminders:

1. We’ve launched a premium tier for deeper coverage. You can upgrade here.

2. You’ll now get 2 newsletters per week (Monday, Thursday). That way, we can give you timely takes and keep it short and sweet.

Here’s today’s plan:

• Tech News Takes — digestible analysis and commentary

• Tool of the Week — tools you’ll find useful

• Strategy Tips — strategy frameworks and deep dives

Uber Wants "No Tax on Tips"

Plus: Tinder's AI flirting game; TikTok's bidding war

⚡ Tech News Takes ⚡

Uber and DoorDash Want “No Tax on Tips”

• What’s up: President Trump’s “no tax on tips” proposal excludes rideshare and delivery drivers, because they’re classified as self-employed contractors — not employees. But now, those companies are lobbying hard to have their drivers be included, so they keep more of the tips they make. In prior debates about contractor vs. employee, those same companies have lobbied hard to maintain drivers’ contractor status, arguing that it promotes flexibility for drivers.

• So what: In a nutshell, Uber and DoorDash are trying to have their cake and eat it too. It’s true that contractor status adds flexibility for drivers, but the companies benefit even more — no healthcare to pay, no minimum wage to hit, etc. And there are clear benefits to Uber and Co if this goes through. With drivers’ tips untaxed, Uber could effectively “split the tax savings” with drivers, lowering the drivers’ revenue from each ride/delivery. Or, (slightly) more charitably, they could “split the tax savings” with customers, lowering prices on rides and deliveries…

Tinder Launches AI Flirting Game

• What’s up: Tinder has a new feature called “The Game Game”, which lets people flirt with AI bots for practice. Users are given points for holding a conversation and scoring a date within a time limit. According to Tinder, "This is just a game. It is not designed to replace human conversations. Instead, it's actually designed to encourage real conversations with real people in real life.”

• So what: I’m torn on this. On the one hand, it’s sad that our social skills as humans have atrophied so much that we need AI’s help! And it’s also sad and true that technology played a role in that atrophy. But on the other hand…. 21% of Americans feel lonely, 8% say they have no close friends, and those numbers are not moving in the right direction… so we need all the help we can get. I’m willing to give Tinder and other tech-infused efforts the benefit of the doubt.

🛠️ Tool of the Week 🛠️

This week, we partnered with a company that is absolutely crushing it.

They’re bringing agentic AI to companies like Vanguard, Salesforce, and Intuit.

Here’s a quick word from them.

You’ve heard the hype. It’s time for results.

After two years of siloed experiments, proofs of concept that fail to scale, and disappointing ROI, most enterprises are stuck. AI isn't transforming their organizations — it’s adding complexity, friction, and frustration.

But Writer customers are seeing positive impact across their companies. Our end-to-end approach is delivering adoption and ROI at scale. Now, we’re applying that same platform and technology to build agentic AI that actually works for every enterprise.

This isn’t just another hype train that overpromises and underdelivers.
It’s the AI you’ve been waiting for — and it’s going to change the way enterprises operate. Be among the first to see end-to-end agentic AI in action. Join us for a live product release on April 10 at 2pm ET (11am PT).

Can't make it live? No worries — register anyway and we'll send you the recording!

Save your spot — register today

🧭 Strategy Tips 🧭

When I first read today’s news story about Uber wanting “no tax on tips”, I couldn’t stop ruminating over this point:

And I didn’t understand why it was looping through my brain. But finally… after 5 minutes… it hit me. This is basically just a value stick.

Remember this diagram from a few months back?

In the original value stick, we don’t explicitly call out taxes… but let’s map the old terminology to this new Uber situation.

• Consumer surplus – the highest price customers are willing to pay minus the price you actually charge them.

• Value captured – the price you charge customers minus the price your suppliers charge you.

• Supplier surplus – the price your suppliers actually charge you minus the minimum price they would accept.

In this situation, Uber riders are the consumers at the top, Uber drivers are the suppliers at the bottom, and Uber is in the middle.

Taxes can be thought of as part of an invisible red bubble beneath “willingness to supply”. And in that red bubble you’d also have the cost of gas, cleaning supplies, etc.

If the size of that red bubble shrinks, it pushes down willingness to supply. Drivers would be willing to drive for less total revenue, because they get to keep more of it. So if nothing else changes, then their supplier surplus gets bigger.

But something else will probably change…

Like I hinted above, Uber might push supply costs down, paying drivers less per ride, and capturing more value for themselves. In addition, they might also lower prices consumers pay, passing on those savings.

So although it’s nice to see Uber (and DoorDash and others) sticking up for their drivers, it’s not a purely unselfish move.

The forest is growing.
Feel free to share this post.

If you have feedback or want to discuss advertising,
reply to this email or send me a note.