Get Your Act Together, Kiddo

Brutally Honest Hiring Advice from a Fund Head

Let me set the scene.

It’s hiring season at my fund. I’ve laughed. I’ve cried. I’ve yelled at my laptop. I’ve dramatically flung my phone across the room more than once. I’ve sent voice notes in ALL CAPS. Why? Because the talent is there, but the applications?

Chaos!!

I’m reading form after form from some of the smartest Gen Zers out there and wondering why none of them seem to actually want the job they’re applying for. It’s not just one or two, it’s systemic. And it tells me something bigger: there’s a gap. Between what people think applying is and what actually makes you stand out in today’s startup ecosystem.

The world of work has changed. Fast. From quiet quitting to rage applying to the idea that every job is just a stepping stone to your "real career"- this generation is navigating a minefield of hustle culture backlash, disillusionment with corporate ladders, and a deep desire for meaning. That’s valid. But startups are a different beast. We need urgency, ownership, and alignment. And yes, sometimes we also need someone to fix the damn printer.

Gen Z has many superpowers: irreverence, wit, adaptability, and digital savviness. But those only land if you show them right. Irreverence without thought is just noise. Personality without direction is just vibes. This post is for anyone who’s ever applied to a startup and wondered why they didn’t get the call back. Or worse, didn’t even get ghosted. Just...silence.

So here are 20 lessons from the other side of the table. From someone who’s hiring right now. From someone who wants to say yes to you. From someone who believes you’re better than a resume recitation.

Take what resonates. Adjust what doesn’t. But most of all, give a damn. It shows.

1. People don’t give enough of a shit.

I need to say this with my whole chest: most people applying don’t actually care. Not really. They’re applying on autopilot, chucking the same application to 50 companies, hoping one sticks. But here’s the thing- we can tell. It shows in your tone, your typos, your inability to reference what we actually do. Caring can’t be faked. And if you don’t care, why should I?

2. Show me your personality, or I’ll assume you don’t have one.

When I ask “Why you?”, I’m not asking for a LinkedIn summary. I’m asking for a person. A glimpse of who you are to work with, what makes you light up, how you think. If your answer feels like it was run through three layers of PR, I’m tuning out. Tell me something only you could say.

3. If you’re a generalist, act like one. Define your own job.

Generalist roles are not a free pass to figure things out later. They’re for people who see the gaps and fill them. If you want to be a generalist, show me how you understand the org’s needs, what you think the job to be done is, and how you plan to plug in. If you can’t articulate that, you’re not a generalist. You’re just vague.

4. Knowing ≠ understanding ≠ doing.

Telling me you “noticed low retention” is not impressive. Everyone can spot problems. I care about whether you figured out why it happened, and what you did about it. Observation is passive. Insight takes thought. Implementation takes guts. I’m hiring for the third one.

5. The ‘Anything else?’ section is where legends are born.

Most people waste it. They say, “No, nothing else.” And that’s a shame. Because this is where I learn the most about you. The people who shine here give me texture: a story, a moment, a strange obsession, a burst of humour. It’s your one shot to go rogue…and most of you just shrug.

6. Please stop writing like you’re applying to the civil services.

Startup people are, by and large, human beings. We speak like human beings. So when your application opens with “To whom it may concern at your esteemed organisation,” I already know you don’t get our vibe. Talk to me, not at me. I’m reading this on my phone between calls. Make it worth my time.

7. Read the damn JD. Properly.

You cannot write “I’m excited about an investment role” when the job is for a community manager. I shouldn’t have to say this, and yet, here we are. If you can't pay attention to the role you're applying for, why would I trust you with anything more nuanced?

8. Don’t just repeat your CV. Expand it.

If every section of your form is a copy-paste of your resume, what’s the point? This is your chance to add meaning, to explain why something mattered or what it taught you. Use your application to give depth, not duplication.

9. Bring joy. We need it.

Small teams are intense. We work long hours. We’ve literally slept in the office. If I can’t imagine you cracking a joke in the middle of a chaotic day, I’m probably not bringing you in. Your competence gets you to the shortlist. Your vibe gets you through the door.

10. Play to your strengths, whatever they are.

English isn’t your strength? That’s okay. Find another way to show me what is. Record a video. Share a Notion doc. Send me screenshots of what you built. Clarity matters more than polish. I care about whether you can get things done, not whether your grammar is flawless.

11. Stalk me (the professional kind).

Read our blog. Look through our LinkedIn. Watch that podcast I did. Referencing our work in your app isn’t creepy, it’s a green flag. It shows me you’re intentional. That you chose this role. And that already puts you ahead of half the pile.

12. Bragging makes me suspicious.

Confidence is great. Arrogance is not. When someone writes “I’m the best at X,” I instantly start looking for the holes. When someone says “Here’s what I did and what I learned,” I start taking them seriously. Don’t tell me you’re great. Let your work do that for you.

13. Don’t trash your old job. Not yet.

Even if your last workplace was a dumpster fire, keep it classy. Tell me what you learned. What didn’t work for you. What you’re looking for now. If your app is full of blame and bitterness, I assume you’ll talk about me that way too when you leave.

14. Irreverence is delightful. Sloppiness is not.

You can be funny. You can be informal. You can even swear a little if that’s your vibe. But if you spell the company name wrong, forget to add links, or clearly didn’t bother proofreading, I’m out. Be cool, but be competent.

15. Unrelated work experience? No problem- if you do the storytelling.

I don’t care that your last job was in hospitality or retail. I care how you connect that to this role. What did you learn that’s relevant? What skills are you bringing forward? If I have to do that mental math for you, I won’t.

16. We always know when you don’t care.

You might think you’re being clever, but generic apps smell. I can tell when someone’s just clicking Apply across the internet. If you can’t bring even a flicker of genuine curiosity to the process, don’t bother. Startups have no space for half-heartedness.

17. Yes, I can tell when you ChatGPTed your app.

Especially when you leave the em dash. I’m not against using tools, but please, edit. Add your voice. Cut the fluff. We want to know you, not GPT’s version of what you think we want to hear.

18. Look through the JD, not just at it.

Ask yourself: what does this role actually require? What kind of thinking, energy, context-switching, communication? Then show me that you get it, not by listing the traits, but by giving me proof you’ve lived them.

19. Attention to detail isn’t about typos. It’s about effort.

Did you format your resume properly? Are the links working? Did you reference the right team member? These things show care. I don’t expect perfection, I expect that you took this seriously.

20. Ask yourself: would you still want this job if nothing changed in 6 months?

No title bump. No media coverage. Just you, doing this job, day in, day out. If that doesn’t excite you even a little, please don’t apply. This isn’t a stepping stone. It’s a real job. And it deserves someone who wants to do it.

In short: You need honesty, persistence, and a dash of humor. Don’t overthink it – just don’t underthink it. Show you’re real, resourceful, and ready for the ride. The startups that thrive want humans- real, flawed, capable humans. So be one, not a walking cliche, and you’ll have a shot.

Let’s land this plane.

If you’ve made it this far, congrats. That’s already more effort than 80% of applicants. But effort isn’t the goal. Intention is.

Hiring is not a transaction. Especially not at small, weird, chaotic, beautiful startups. It’s a high-stakes invitation to build together. We’re not just hiring skills. We’re hiring energy, ambition, curiosity, and commitment. We’re hiring the people we want in the room at 11pm before a big launch, and the ones we’ll want to get breakfast with the next day.So don’t just show us what you’ve done. Show us how you think, who you are, and why this matters to you.

No one expects perfection. We expect presence. And proof that you actually want to be here.

If you do? We’ll fight for you.

(And if not, there’s a corporate somewhere with unlimited coffee and no soul. Go nuts.)