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Startup Growth Journey: From Big Tech to Early Stage

/ 5 min read

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Table of Contents

People Vary Wildly — Big Companies Hide This

Big companies can select from massive talent pools, so the variance among hires is low. Startups have a tiny selection pool, so the variance can be shockingly large. This is great for personal growth—seeing diversity forces you to think harder and communicate better.

Takeaway — Hold your standards. In big companies, people think similarly so you rarely need to argue hard. At startups, it’s daily. If you don’t hold your ground—and you’ve had proper big-company training—you may miss a chance to educate the team, and you’ll likely pay for it with rework later.

Too Many Escape Routes Make Quitting Easy (Especially in Tech)

Whether IC or CTO, technical skills are highly transferable. Other well-paying opportunities are always waiting. When you hit friction—infuriating conflicts, for instance—you ask yourself: why am I doing this? I could just go solo. Why suffer?

Product Lead Is a Strategy Role, Not a Design Role

A good product lead shouldn’t over-index on UX design—product strategy matters more.

Takeaway

  • Beyond user experience, consider long-term strategic goals
  • Build a clear roadmap from core features to advanced capabilities, with continuous iteration
  • Founders must maintain the big picture and strategic direction, not get lost in technical details

People Define the Same Concepts Differently

Everyone knows “fast iteration” and “user experience” matter. But when these two conflict—where do you draw the line? What ships now vs. what waits? This is where friction concentrates.

Firing People

Firing isn’t just revoking login credentials—it affects team morale. Have clear standards, communicate expectations, and minimize surprises.

  • Best outcome: the fired person’s peers aren’t surprised, and their supervisor feels relieved.

Doing Is Hard

In retros, the same action items come up repeatedly, yet people keep doing what everyone agrees should stop. Knowing vs. doing is the real gap. Most people know what’s right or wrong—but changing behavior is brutally hard.

Wishful Thinking

Founders almost certainly start with wishful thinking. Maybe that’s why they say startups only truly begin after the first pivot—reality has to slap founders before they see things clearly.

The Whole World Runs on Duct Tape

“The whole world runs on duct tape”—this saying rings truer every day. As you dig into any industry, the limits of human cognition become glaringly obvious. Someone might be deeply knowledgeable in one vertical but becomes part of the duct tape crew in your domain. No single person carries an entire business, especially ambitious ones. Founders included (especially founders…).

Key People Must Have Skin in the Game

Refer to “too many escape routes.” Important people always have options. Especially during conflicts—if they have no skin in the game, they’ll walk. Vision can hold people temporarily, but persistent team conflict will drive them away.

Effective Feedback Is Incredibly Hard

Netflix’s 4A Feedback Framework is excellent and highly recommended.

Small, Elite Teams Matter

Don’t expand headcount for speed. Core members must resist the expansion urge. Slow is fast—even at a startup obsessed with speed, you must walk steadily before you can run.

Quick Brain Dump

  • January 5, 2023 Some problems exist regardless of company size. Don’t expect switching jobs or companies to avoid them. If your team lacks strategic vision, both big and small companies will fall into local optimization traps. The people you follow, work with, and choose to join—that’s what matters.

  • January 6, 2023 Startup experience transfers powerfully to big companies. Problems that startups face constantly—but big companies have abstracted away—give you rare training opportunities.

  • January 10, 2023 Team building was harder and slower than I expected. Probably related to the higher variance in small-company hires.

  • January 11, 2023 On complex projects, managing people is easier than managing tasks. People don’t appear or disappear randomly, but tasks change constantly—especially in fast-moving projects where you lack full visibility.

  • January 11, 2023 Self-doubt is everywhere. Am I doing the right thing? Is this valuable? Should I have said that? Just… live with it.

  • January 12, 2023 Fight to the end, because nobody’s backing you up. In big companies, you can escalate—if you have evidence and accountability, you’re fine. At startups, even if you’re right, not fighting means someone pins blame on you. The only option is to fight.

  • January 14, 2023 Be CEO if you can. CTO is a decent stepping stone, but mostly a glorified employee. If you have strong opinions about many things, be CEO—it’s much easier to push things through. Of course, this requires genuine judgment and strategic vision.

  • January 14, 2023 Abstract numbers have real-world impact. In big companies, some numbers feel theoretical. When you’re running things yourself—runway of 2 vs. 4 years, dev cycle of 1 vs. 3 months, 1 vs. 3 parallel projects—these aren’t just spreadsheet cells. They affect product quality, team morale, stress levels, everything.

  • January 14, 2023 Almost nobody runs meetings well. Someone who can effectively prepare, organize, and produce actionable outcomes from a meeting is pure gold. If you meet such a person, recruit them immediately.

  • January 20, 2023 Don’t be right, be helpful—then don’t be correct, be successful. Too many people, especially big-company folks seeking stability, optimize for not making mistakes. But avoiding mistakes is the enemy of success.