TGIFFFFF BABY!

You guys are gonna be so proud of me! I FINALLY managed to read something that wasn't an email (an actual book) over the last two weeks. 🏆 I loved it! 

I’m actually really excited about this week’s segment, which feels rare because… well, I'm usually panic-writing it at the last minute. But if you don’t know, my background is in headhunting specifically in the med device space, where I spent years helping engineers decide if they should take jobs building things like brain implants or machines that kill stomach tumors with literal bubbles. A lot of those companies were early-stage startups doing wild, novel, high-stakes things, and I got pretty good at helping people figure out if the opportunity was brilliant or just marketing itself as such. So if you’re even thinking about joining a startup, this one’s for you.

This week on The Offer Letter:

• Best jobs on the N+1 Job Board WOOHOO!
• Should You Take That Startup Job?
  
• Someone ask me something in the Ask A Recruiter section!!!

Happy 4th next week everyone! 💙

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🔥 This Week's Best Openings

Hottest jobs on the N+1 Job Board this week: 

•Sr. Administrative Assistant – Boston, Converse [Apply here]

•Executive Assistant – NYC, Up To $190k [Apply here]

🎯 Should You Take That Startup Job?

I came agross this post this week (click the pic to read the full discussion on LinkedIn):

As someone with completely unmedicated, untreated, and honestly kind of cherished ADHD, I can say with full confidence that my personal version of career hell is being a cog in some 18-layered corporate death star where getting a Zoom background approved takes six weeks and people get excited about a pivot from weekly to DAILY standups. Not satire.

Now listen. I’m not saying startups are for everyone. In fact, when I interviewed for the last startup I worked at, the CEO looked me dead in the eyes and said, “You need to be a little bit neurotic and kind of enjoy chewing glass to survive here.” He wasn’t wrong. So no, this is not a manifesto for everyone to go join the next VC-backed fever dream.

But I am saying this: Jesse’s post is correct. Even just one stint at a startup will teach you things no corporate gig ever could. It’s like getting an MBA and going through a breakup at the same time. Character-building! Terrifying! Very educational.

Here are a few lessons I learned in my three-year stint at a proptech startup that, frankly, should have been a Netflix dramedy:

Don’t smoke in the Turo. If you light up a cigarette in the Turo you rented to drive the team from Austin to Dallas to attend a Cowboys game, you will get banned. Forever. (To be clear, this was not me. It was my boss. I’m a little angel who would never do such a thing....in a Turo)

Series A is Latin for “You Might Get Fired Tomorrow.” One morning I watched all my friends get called into a conference room one by one like it was a live-action Squid Game, and by some sick twist of fate, I was the only one who didn’t get laid off. The twist? I was now the only salesperson. But plot twist #2: I figured out how to automate the entire outbound process and literally closed the same revenue as a team of 12. (Which was one of the most valuable experiences of my career! And also made me wonder why they hired 12 people in the first place.)

Do not fall in love with the cute engineer. You will be rejected. And then still have to see him every day. And then, for reasons your therapist will someday unpack, you will start referring to his office as “The Fart Box.” Just trust me. Don’t do it.

Anyway. All that to say: if you’re bored, stagnating, or just have a masochistic streak you’d like to explore professionally, working at a startup can be a beautiful, chaotic way to figure out who the hell you are.

But here’s the catch Jesse didn’t mention:

Not all startups are worth your time. Some will teach you more than any job ever has and make your next move 10x easier. Others will chew through years of your life and leave you with PTSD, a useless bullet point on your resume, and no actual skills except knowing how to cry quietly in the bathroom.

Here’s the thing about startups: 90% of them fail.

That’s not a fun statistic. That’s a warning label.

So before you sign on to be employee #17 at a place that might change the world but more likely will just change your tax bracket for the worse, here are the three non-negotiables you need to check before saying yes:

1. What Has the Leadership Team Actually Done?

It’s not enough that the founder went to Stanford or knows how to talk to VCs. The question is: have they built anything real before?

Look them up on Crunchbase. What’s their track record? Have they taken a company from zero to exit? Or even through a meaningful growth phase? Do they have experience managing teams and navigating the mess that comes with actually scaling something, or are they just good at making pitch decks?

Because if this is their first time doing this, and they’re asking you to gamble your time, career, and income on their vision, you need to know what you’re signing up for. Early-stage leadership matters more than anything. If they’re learning as they go, you will probably be the one paying the price.

2. Does the Product Actually Solve a Real Problem?

If you can’t explain what the company does without using buzzwords, that’s your first clue. The best startups solve problems people already know they have...and that they’re already paying someone else to solve.

It doesn’t have to be revolutionary. But it does need to be better: faster, cheaper, more effective. Not just “different.” Different doesn’t create demand. Better does.

If the company’s whole strategy is “educating the market” or “changing consumer behavior,” pause. That’s not a startup. That’s an uphill battle with no guaranteed payoff.

3. Is There a Clear Exit Strategy?

Here’s the part that gets glossed over in most startup interviews: what is the actual endgame here?

Startups are not built to be stable, long-term employers. They are designed to grow fast and exit, either by getting acquired or going public. That’s the model. That’s the goal. And if the leadership team can’t clearly explain how they’re getting there, that should stop you in your tracks.

You’re not just trading your time for a paycheck, you’re trading it for equity, impact, and the promise of a big outcome down the line. But that only matters if that outcome is realistically on the table.

Ask yourself:

• Who would acquire this company? Is there a market for it?

• Are there recent comparable acquisitions in the space?

• Is this a category that actually sees exits, or just endless rounds of funding?

• Is the market big enough to justify going public someday—or are they trying to make fetch happen in a niche that’s too small to matter?

If leadership starts talking in vague language about “long-term vision” or “building something meaningful” but can’t back it up with a roadmap or actual numbers, they’re not building a business, they’re building a story. And you don’t want your livelihood tied to someone else’s fantasy.

The Bottom Line:

Startups aren’t inherently good or bad. Some are rocket ships. Others are slow-motion car crashes with cold brew on tap. The trick is knowing which one you’re signing up for.

If you’re considering an offer, take off the rose-colored glasses. Ask the questions most people are too polite to ask. What has leadership actually built? Is the product solving a real problem? Is there a realistic path to a meaningful outcome?

This isn’t about being cynical. It’s about being clear-eyed. Your career is not a lottery ticket, and you don’t owe anyone blind belief in their “vision.” Bet on teams with a track record. Bet on products that sell themselves. Bet on businesses, not hype.

Because the truth is, being early at the right startup can change your life.

Being early at the wrong one can set you back years.

Make sure the risk is worth the return.

Stuck in your job search? Not sure how to handle a tricky interview question or navigate the hiring process? Submit your question anonymously, and I’ll answer it in an upcoming newsletter—no names, no judgment, just real advice from a recruiter who knows the game.

📅 See you next time!

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