Why Your Startup Dream Is Really a Nightmare

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It’s good to be back. 

No wait. I’m lying. 

I grew accustomed to taking a break and have grown lazy with this bullshit called free time, sunshine, and life outdoors. God forbid.

But my ego missed all the attention, and I get along well with my fellow career masochists. You are my people.

Regardless, I’m back to expressing all the ugly truth you wish you could say, but you’re busy keeping your nose clean and playing politics. 

I get it—and won’t hold it against you.

Today, I share why leaving your cushy big company corporate role for a startup is probably a dumb ass idea (in most cases).

Let’s start with the foundation first. Chop chop. 

Who Should Join A Startup

I previously shared that startups have a 0.00006% shot at becoming unicorns. Let’s be honest; that means you will not join one. 

I’m comfortable making that bet. 

Startups can be an excellent fit for early career professionals or those pivoting into a new space with less experience. Or those struggling with being unemployed for extended periods. 

Let’s note that startups may also be suitable for a passion play. Startups help you reinvent or create the type of career and lifestyle you want—assuming you have a founder role

It’s an accelerated learning, all-hands-on-deck proving ground of survival. You’ll get some extraordinary war stories and the scars to prove it. 

But startups are not for seasoned executives. 

The risks typically outweigh the benefits unless you negotiate your ass off.

Let’s dive into why.

Your Career Needs The Long Game 

The median job tenure for startup employees is just two years. You’ll notice that’s conveniently about half the time the average employee negotiates their traditional four-year equity vesting schedule. 

It’s even less for C-Suite startup executives – who average 18 months. Sometimes, the highest-earning “tall poppy” needs to get whacked for payroll. 

It means that the allure of some promised equity land is not worth sticking around through the mucky-muck.

It means that if you make it two years through a chaotic, pre-product-market-fit fiery hellscape, you get half the percentage of stock you agreed to. Oh, and you still have to purchase the options, by the way.

It means that you work for two years at a reduced salary, and in most cases, you will find yourself looking for work again. And soon.  

With the pace of innovation and general human nature to look more at “what have you done for me lately?” you may struggle to get back to a cushy corporate role again. 

You’re a reckless startup pro now. 

Are you still qualified to lead in the way that you had previously? 

Recruiters and hiring managers will want to know. 

It means you’ll likely hop back into a startup every 18-24 months out of sheer necessity. 

Your pay stagnates, and your growth caps. 

I call this the career death spiral—and I’ve helped clients through it hundreds of times. 

But recently, I’ve been more proactive and helped many 7 figure earners avoid the pitfalls altogether. 

But what if…?

A Crystal Ball Isn’t Decision Making

Snap. Stripe. Slack. Facebook. Google. 

They are unmistakable winners in the money-making game. Did you predict their success back when they were in the earliest days—before it was a sure thing? 

If only you had a crystal ball (and perfect timing) to anticipate that these rocketships could have propelled your career (and bank accounts) to elite heights. 

Unfortunately, once you know they will be winners, it’s probably too late to make “F.U. money” from joining. 

If you’re already comfortably making a half million a year or more—with RSU refreshers, great benefits, and a known battlefield—so what if you’re only a senior director… 

A startup is not the answer to promotion. 

But Jacob, what if I missed out on a winner?

I’ve had over 2500 clients. 

One time, I had a client choose to stay a Director at Cisco instead of joining Slack at an early stage. (To be fair, this was well before we met).

It’s a bummer indeed, but I promise they’re still doing well for themselves, and it’s a total first-world problem. 

I commend them for their decision to stay at Cisco.

You should optimize your career for long-term success to meet your economic goals and lifestyle ambitions. 

It’s more of a Warren Buffet style, perhaps. 

Sure, it’s better to be lucky than good — but we optimize for being good because luck is, well, luck.  

Avoiding A Multi-Seven-Figure Mistake

Roughly two years ago, I advised a Sr. Director at a Fortune 500 company. 

They were doing well for themselves (roughly $750,000/yr average) but felt that a change was in order. 

The circumstances are what you’d expect from the big industry bulwarks—forward career momentum had stalled as all the folks above them had 20-year tenures and succession plans built for years.  

Plus, it does get old and boring. 

They had multiple choices. 

Join an early-stage startup with successful friends—or stay put to take the lead on a new project. 

Remember, Fortune 500 projects can take 3-5 years of commitment to get traction. 

We reviewed the possible outcomes and discussed the perception, the potential career death spiral, earnings, liquidity chances, etc. 

We also discussed what they valued in life, how their family was doing, what they wanted more time to do, and where they wanted to be in 5-10 years.

They chose to stay put and take on the project, knowing that they were likely trapped for years for fear of burning any bridges and eviscerating their career.


They accelerated a terrific outcome in under two years, and the company rewarded them with a new executive leadership role and a compensation package nearly double their previous salary.  

I’d be lying if I said these results were typical. But my argument is, why would you gamble $750k a year and stability for a minuscule shot?  

Maybe they were lucky that they found a way to accelerate an outcome within the F500 landscape, but they made a much more calculated bet, IMO. 

Look, I don’t hate startups. I owe my career to the opportunities that they brought me. But there is a time and place for them. 

If maximizing your earnings, reaching financial independence, and more controllable stability are on your priority list, I suggest you look elsewhere.

You better make damn sure that if you move from a cushy corporate role, you negotiate an opportunity to protect your family, career status, perception, and anything else you may put in harm’s way. 

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