Make the right bets (before it’s too late)
03/17/25 • Innovation

Make the right bets (before it’s too late)

Make the right bets (before it’s too late)

Hey, it’s Matt.

Creating something new is basically a series of bets-on ideas, timing, people, and execution.

Some feel obvious, some feel risky, and some only make sense in hindsight.

In this week’s newsletter, you’ll read about someone quitting their cushy FAANG job before AI makes the choice for them, founders shipping scrappy, imperfect products to get real feedback instead of waiting for the “perfect” time, and others ignoring the hype completely to double down on what they know actually works.

Call it luck or skill, but every successful founder has placed the right bet at the right time. They don’t always feel safe in the moment-but looking back, they’re the ones that make the best stories.

Here’s what else you can expect in this week’s edition:

  • The UX shortcuts that let startups ship without a designer (and why perfection kills momentum)
  • How Y Combinator’s 20-year playbook turned dorm room ideas into billion-dollar giants
  • The sneaky reason most products feel uninspired-blame the obsession with metrics over originality
  • Why AI-first design might backfire-when software is built for robots, human users get left behind
  • And more…

Enjoy issue #98-see you next week!

– Matt (@mattdowney)

P.S. If this was forwarded to you, you can sign up here.

MOST INTERESTING

Y Combinator at 20: What’s changed (and what hasn’t)

YC’s playbook helped turn dorm room ideas into billion-dollar giants, but does it still work today? A deep dive into how its approach has evolved-and why some things never change. (Digital Frontier)

Claude vs GPT vs Perplexity

Anthropic, OpenAI, and Perplexity are carving out distinct AI strategies-hybrid reasoning, emotional intelligence, and viral content. The latest updates show AI’s next chapter is about specialization, not raw power. (Simple AI)

Dumping the ‘content creator’ label for real creativity

Christian Heilmann calls out the rise of AI spam and engagement-first content, arguing that platforms reward cheap tricks over genuine craft. But there’s still a way to break through-by focusing on what actually matters. (Christian Heilmann)

TOP RESOURCES

Startup UX: Building smooth flows without a designer

No designer? No problem. This guide shows how startups can repurpose existing design patterns and UI libraries to create intuitive user experiences-without getting stuck in perfection paralysis. (Tibi Notes)

Why most products today feel uninspired

When design is dictated by engagement metrics instead of originality, everything starts to look the same. Ed Orozco breaks down how short-term thinking leads to forgettable products-and how founders can break the cycle. (UX Collective)

Easing Wizard: A better way to fine-tune animations

CSS animations don’t have to be guesswork anymore. Easing Wizard gives you real-time control over easing curves, helping you create fluid, polished motion without endless tweaking. (Easing Wizard)

What’s TRENDING

Ex-FAANG engineer quits before AI automates his job

Jasper Gilley saw the writing on the wall and walked away from his high-paying FAANG role-before AI could make him redundant. His story raises a big question: if even senior engineers are rethinking their future, what should the rest of us be doing? (Jasper Gilley)

AX (Agent Experience) design: Is it sidelining human users?

AI-powered interfaces are supposed to make software more intuitive, but what if they’re making it worse? Jim Nielsen argues that designing for AI agents-rather than people-might be a slippery slope. (Jim Nielsen)

Dear Student: Yes, AI is here, you’re screwed unless you take action…

AI isn’t just speeding things up; it’s reshaping who gets hired (and who doesn’t). (Geoffrey Huntley)

My stack

These are the tools that help me run my business every day. I happily pay for each of them-they’re worth every penny. I hope you find them useful, too.

  • Beehiiv → How I send this newsletter every week. 10/10 would recommend.
  • Brain.fm → How I kickstart my productivity and find flow-state.
  • Figma → How I quickly go from idea to design to product.
  • Mercury → The best business banking I’ve ever used.
  • Screen Studio → How I record engaging videos.
  • Typefully → How I post content to my socials.
  • Kick → My bookkeeping on auto-pilot.

And that’s a wrap!

Thanks for reading today’s issue. If you have any ideas for what you’d like me to cover in future issues, just hit reply and let me know.

And if you found today’s newsletter useful, please share it with your friends!

Matt Downey
Founder, Digital Native
@mattdowney

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