Working in Startups
A Survival Guide from Someone Still Surviving
Note: Check the slides here: AWS eNovators Buildspace
Hi, I’m Neil
- Lead Software Engineer by title
- Project Manager by necessity
- DevOps Engineer by “can you also handle the servers?”
- QA by “you wrote it, you test it”
- Community Connector & Career Coach by choice
- Somehow still a hobbyist
Note: The job description said “Software Engineer.” The job itself said otherwise.
Agenda
- So You Joined a Startup
- Wearing Every Hat (Even the Ugly Ones)
- The Good Stuff
- The Not-So-Good Stuff
- Lessons from the Trenches
- Q&A (a.k.a. group therapy)
Joining a Startup
“We’re like a family here.”
— Every startup recruiter, moments before assigning you 3 roles
Note: If your workplace is a family, it’s the kind that argues about the thermostat and shares one Netflix account.
What They Told You
- Cutting-edge tech stack
- Flat hierarchy
- Equity that’ll make you rich
- Free snacks
What Actually Happened
- Legacy code from a freelancer
- No one knows who decides
- Equity worth less than the snacks
- The snacks ran out in month 2
Note: If someone offers you equity instead of salary, ask them if the landlord accepts equity too.
Wearing Every Hat
A Day in My Life
- 9 AM — Sprint planning (manager hat)
- 10 AM — Code review (senior eng hat)
- 11 AM — Fix production (firefighter hat)
- 12 PM — Lunch (just kidding, debug while eating)
- 2 PM — Deploy to prod (DevOps hat)
- 4 PM — Actually write code (finally)
Note: Context switching is not a skill. It’s a trauma response.
The Real Job Description
Write code. Review code. Deploy code. Fix code. Explain code to people who don’t read code. Repeat until IPO or burnout, whichever comes first.
note: The real full-stack is not frontend + backend. It’s engineering + management + ops + therapy.
The Good Stuff
10x Learning Speed
- No one to hand things off to — you become the expert
- Ship to production on day one (scary, but real)
- You see the entire system, not just your corner
- One year at a startup = three years of experience
Note: You’ll learn more from one production outage at 2 AM than an entire semester of distributed systems.
Your Impact is Real
- Your code doesn’t sit in a backlog for 6 months
- You talk directly to users
- You can say “I built that” and mean it
- Decisions you make today ship tomorrow
Note: At a big company you’re a cog. At a startup you’re the entire machine. Both are exhausting, but one is more interesting.
Real Relationships
Small teams mean you actually know everyone. Your teammates become your war buddies. Nothing bonds people like a shared production outage at midnight.
The Bad Stuff
Context Switching
- You can’t do deep work in 30-minute windows
- Every Slack ping is a potential derailment
- Being “needed everywhere” sounds nice until you’re actually needed everywhere
Note: If you’re in 6 meetings a day AND expected to ship features, something is broken. Probably you.
Burnout is Not a Badge
- “Hustle culture” is just exploitation with better marketing
- Saying no is a skill, not a weakness
- If you’re the only person who can do something, that’s a risk, not a flex
- Rest is not laziness — it’s maintenance
Note: You can’t pour from an empty cup. And you definitely can’t debug from an empty brain.
“I’ll just fix this one thing before bed.”
— Me, at 11 PM, every night, lying to myself
Lessons Learned
Document Everything
Future you will not remember why you wrote that code. Your teammates definitely won’t. Write it down. ADRs, READMEs, even comments — anything beats “ask Neil, he knows.”
Note: “Ask Neil” is not documentation. It’s a single point of failure with anxiety.
Protect Your Yes
Every “yes” to a meeting is a “no” to deep work. Guard your time like production credentials — don’t hand it out to everyone who asks.
Automate the Pain
If you did it twice, automate it. CI/CD, linters, deployment scripts, monitoring alerts — let machines handle the boring stuff so you can handle the interesting problems.
Build the Team
- Hire people smarter than you in areas you’re weak
- Mentor others so you’re not the bottleneck
- A great team survives a bad product. A bad team kills a great one.
Marathon, Not a Sprint
Ironically, we call our work “sprints.” But the people who last in startups are the ones who pace themselves. Sustainable speed beats burnout speed every time.
“The best time to plant a tree was 20 years ago. The second best time is now. The worst time is during a production outage.”
— Ancient startup proverb (probably)
TL;DR
Startups will teach you everything, break you a little, and make you proud of what you built. Just remember to sleep.
Q&A
Questions, war stories, or emotional support — all welcome.
Thank You!
Let’s connect:
| GitHub | scaredmeow |
| Neil Riego | |
| Website | brain.neilriego.me |
| hello@neilriego.me |