Startup Delusions Destroy Executive Careers

Why seven-figure executives are gambling away millions on startup lottery tickets, and the smarter alternatives that preserve wealth while satisfying entrepreneurial ambition.

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It's time to address a dangerous career delusion that costs top executives millions in lost compensation and years of career leverage.

For the sake of my personal flair for provocation, I’ll coin today’s topic—The "startup savior complex."

Knowing my typical reader, I suspect that many of you have either lived or fantasized about the incredibly sensual freedom of riding a unicorn startup into the sunset.

That seductive whisper telling accomplished corporate leaders they should abandon their boring, slow as molasses Draconian hellscape for startup glory.

It sounds so damn compelling.

But—don’t be fooled.

This isn't just career FOMO. It's full-blown delusions of grandeur disguised as entrepreneurial ambition—at least for most executives.

A string of startup failures has wrecked more executive careers than almost any other single decision I've witnessed in two decades of advising senior leaders.

I watch seven-figure executives convince themselves they're the missing piece that will transform a scrappy startup into the next unicorn. They imagine their corporate experience will somehow overcome statistical impossibilities that have crushed thousands of equally talented leaders before them.

The fantasy goes something like this:

"I'll bring my Fortune 500 expertise to this promising startup, help them scale properly, and ride the rocket ship to financial freedom while finally getting the recognition I deserve."

It's a compelling narrative. And hey, more power to you.

But it's also complete bullshit.

Let's skip the inspirational platitudes and examine this critical career decision point.

The startup path is almost always a financial and strategic mistake for established executives.

The most successful executives I advise aren't constantly chasing the next shiny opportunity. They're not falling for get-rich-quick schemes dressed up in startup mythology.

They understand that real wealth and career satisfaction come from maximizing their position of strength, not gambling it away on statistical long shots.

But here's what makes this delusion so dangerous—it feels rational.

Every data point seems to support the move.

The startup has impressive early traction. The founders went to the right schools. The investors have recognizable names. Your corporate peers are making similar moves.

What you don't see is the graveyard of equally impressive startups that flamed out after 18 months, taking executive careers down with them.

This can also kickstart a career phenomenon I call the “startup meat grinder” — a stringed together series of 4-18 month tenures at companies under $50M in revenue.

This pattern destroys perceived credibility, invites skepticism about your seniority, invites career self-doubt, and forces very tricky career narratives and interview strategies that take precise delivery to pull off. I’ll tackle the meat grinder concept in more depth next week.

Today’s brutal truth?

Your corporate success doesn't translate to startup success any more than being a great surgeon makes you a great race car driver.

Different games, different rules, different odds of survival.

And if you're earning high six or seven figures in a stable corporate role, you're playing from a position most executives would kill for.

Why would you risk that for a lottery ticket, no matter how well-dressed the pitch deck?

There's a smarter way to satisfy your entrepreneurial itch without career suicide—and we'll explore that today. But first, you need to understand exactly what you're up against when startup delusions start whispering in your ear.

The Numbers Don't Lie

Let's start with some cold, hard numbers that most startup evangelists conveniently forget to mention.

Startups have a 0.00006% shot at becoming unicorns.

Let's be honest—that means you will not join one that becomes the next Stripe or Slack.

I'm comfortable making that bet against you. All day, every day.

Yet I regularly watch seven-figure executives leave cushy corporate roles to chase this statistical impossibility. The same executives who would never approve a business strategy with such abysmal odds somehow convince themselves these odds don't apply to their career decisions.

Cognitive dissonance is a hell of a drug.

Here's what's really happening in your brain when startup fever hits—You apply completely different risk assessment standards to your career than you would to any business decision you'd make at work.

If a direct report presented you with a strategic initiative that had a 99.99994% failure rate, you'd throw them out of your office. But when it comes to your own career, suddenly those same odds become "calculated risks" and "strategic pivots."

The math doesn't care about your MBA, your corporate track record, or how impressed you were with the founder's pitch deck. Statistical reality is immune to your resume.

But here's where it gets even more brutal.

Those unicorn odds assume you actually join at the right time and stay long enough to benefit.

Remember, the median job tenure for startup employees is just two years—conveniently about half the time needed for a traditional four-year equity vesting schedule.

For C-suite executives?

The numbers are even worse. You'll average 18 months before you're job hunting again. Sometimes the highest-earning "tall poppy" gets whacked first when payroll cuts are needed during a down round.

So even if you somehow defy the odds and join a future unicorn, you'll probably be gone before the equity pays off.

And that’s assuming the equity is even worth anything at all, you negotiated a great strike price, acceleration trigger, and exercise window—but hey, who wants to get that specific when everyone is stuck in magical fairytale land and they needed you to start yesterday?

You're betting on being lucky twice—picking the right startup AND having the timing work out.

That's not strategic career planning. That's gambling with extra steps.

The executives who beat these odds aren't always smarter than you. They aren't always more talented. Sometimes, they just got lucky on timing and circumstances completely outside their control.

But the startup mythology machine needs success stories to keep the dream alive, so we hear about the winners while the thousands of failures disappear into career purgatory.

Who Actually Benefits from Startups

Before I explain why you shouldn't join a startup, let's clarify who should.

Startups can be an excellent fit for early career professionals building their resumes. When you're 26 years old making $85K as a senior analyst, taking a flyer on a promising startup makes sense.

You're trading modest compensation for accelerated learning and the potential for outsized returns relative to your current trajectory.

The same logic applies to professionals pivoting into new industries with limited relevant experience. If you're trying to break into fintech from traditional banking, a startup role can fast-track your transition in ways a corporate move might not.

Then there are those dealing with extended unemployment who need to get back in the game. A startup offers immediate re-entry into the workforce while you rebuild momentum and options.

Startups also make sense for genuine passion plays—if you literally can't sleep at night because you're obsessed with solving a specific problem and money isn't your primary motivation. But this only works if you have a founder role with meaningful equity, not if you're employee number 47 with a 0.02% stake.

That is, if you want to make any meaningfully outsized returns for the career risk you endure.

For these groups, startups offer an accelerated, all-hands-on-deck proving ground of survival.

You'll get extraordinary war stories, develop scrappy problem-solving skills, and earn the scars to prove it. The learning curve is steep and the experience can be invaluable.

But seasoned executives already earning high six or seven figures? The risk-reward equation is completely different.

You're not trading up from $85K—you're trading down from $750K.

And if you are in the majority of folks that treat compensation benchmarks as a bead on the market—you’ll notice that the asymmetrical balance of power will always lean in the employer's favor—not yours.

In other words, the risk equation is never in your favor unless you are a highly savvy negotiator and align risk mindfully.

When you're already playing at the top of the compensation pyramid, startup equity becomes a negative expected value proposition. Especially for those shifting from RSU to ISO grants.

You're risking a bird in the hand for two in the bush, except the bush is on fire and the birds probably don't exist.

The harsh reality is that most established executives considering startups aren't motivated by rational career optimization. They're driven by boredom, ego, or the fantasy that startup life will somehow be more fulfilling than their current success.

That's not a career strategy. That's a mid-life crisis with a pitch deck.

Let’s make sure that’s not you.

The Compensation Death Spiral

Here's what the glossy startup recruitment pitch conveniently omits—the median job tenure for startup employees is all of about nothing.

This creates a perfect storm for a compensation death spiral.

You leave your stable corporate role for a startup, taking a 30-40% cash pay cut for "equity upside."

You work insane hours for 18-24 months at reduced compensation while the startup burns through funding rounds—diluting the most important upside trigger you negotiated.

The company fails to hit inflated growth targets or simply runs out of runway or pivots up market or down market or mid market or gets scrapped for parts or or or…

Suddenly, you're job hunting again.

Alright, so you’re out some cash from taking that reduced salary—and you’re out 3-6 months for search time—except in this market 9-18 months is more likely—but okay, you knew you were taking a risk and a few bruises makes you a survivor.

You can always just go back to corporate.

Right? Bueller?

Here's where most executives discover the real damage done to their career.

You've now developed a "startup profile" that makes returning to corporate significantly harder. After all, what have you done for me lately?

Corporate recruiters start viewing you as a flight risk.

“Hmm Jane Doe could only hack it for 10 months at a much smaller company. What’s wrong with her?”

Your compensation expectations get reset downward because your last role paid below market rate.

And we can all smell it.

Desperate to maintain momentum, you take another startup role—often at even lower compensation because your negotiating position has weakened.

The cycle repeats, each iteration further eroding your market value and bargaining power.

The financial destruction is methodical and brutal.

Let's say you started at $750K total compensation in your corporate role. You take the first startup job at $450K. After 18 months and no equity payout, you're unemployed for 6 months during your job search.

Your next startup offer?

Maybe $380K, because now you have a (often self-inflicted) track record of accepting below-market compensation and you need to get after those bills from all the job search time.

Another 18-month tenure, another job search, another downward reset.

Within five years, you've gone from a $750K executive to someone fighting for $300K roles—all while watching your former corporate peers collect predictable compensation increases and equity refreshers.

But the psychological damage runs deeper than the financial hit.

Each failed startup chips away at your confidence, your network's faith in your judgment, and your own belief in your market value.

You start accepting roles you would have laughed at five years ago.

The startup death spiral isn't just about one bad decision. It's about how that first decision creates a cascade of compromised choices that systematically destroy the career capital you spent decades building.

The executives trapped in this spiral often blame themselves.

They think they're just unlucky or need to pick better startups next time. They don't realize they're caught in a structural trap where the odds are stacked against them from day one.

You quite literally gaslight yourself.

Next week, I'll show you exactly how executives escape this career purgatory once they're trapped in it.

But for now, understand this—prevention is infinitely easier than recovery.

The Equity Mirage

"But Jacob, what about the equity upside? What if I miss the next unicorn?"

I have to be honest with you.

I once worked with a Cisco executive who could have joined Slack as employee #27. VP-level role. This was before Slack became Slack, obviously.

They stayed at Cisco for their $800K salary instead.

When we first met, they told me this story like it was their biggest career regret. They'd missed out on millions.

Ouch.

Here's what I told them.

You made the smart bet. You played the odds. This time, the roulette ball just happened to land on the green fret.

That's it. That's the whole story.

Also, most people will play a tiny violin for you—given that $800K a year is sort of—crushing it?

Anyways.

Now let me show you what startup equity actually means for everyone else...

You take a $200-400K annual cash pay cut for "equity potential." You get a percentage that sounds impressive but is meaningless without context—1.5% of what exactly? What's the current valuation? What happens during dilution in future rounds?

Many executives don't ask these questions because they're caught up in the excitement and the startup needs them to start yesterday. It’s usually not because they don’t know to dive deeper.

Instead they rely on benchmarks.

“I don’t want to be perceived as skeptical—therefore I just want to make sure I get what roughly everyone else gets so I know I’m simply not getting steamrolled by my peers.”

You stay for 18-24 months (remember, that's the average for executives).

You vest only 37.5-50% of your promised equity before you're gone. You still have to purchase your options at the strike price—surprise!

Did anyone mention you'd need $50K cash to exercise those worthless options? Ya, I know cashless exercises can be an option, give me some grace, equity is damn complex.

The company is nowhere near an exit or a liquidity event.

Your options expire worthless 90 days after you leave unless you negotiate longer exercise windows, which most executives forget to do.

You've effectively worked for significantly below your market rate while watching your corporate peers continue collecting their full compensation packages, annual bonuses, and predictable equity refreshers.

Here's the part that really stings.

Even if the startup succeeds, you probably won't be there to benefit.

The median time from startup founding to IPO is 7-10 years. Your 18-month tenure means you'll watch from the sidelines as the equity you helped create makes other people wealthy.

But let's say you somehow beat all the odds.

You join early, you stay long enough to vest, the company actually goes public, and your equity is worth real money.

Congratulations—you just won the lottery while your corporate peers were building sustainable wealth through predictable compensation growth.

The equity mirage isn't just about the low probability of success.

It's about the opportunity cost of the guaranteed money you gave up chasing the hypothetical money you'll probably never see.

Every dollar you don't earn this year is a dollar that can't compound in your investment portfolio. Every bonus you miss is money that can't buy your family's financial security today. And last I checked, PennyMac doesn’t accept stock options as legal tender.

Every RSU grant you forfeit is equity you actually own, not paper promises tied to someone else's execution.

Most startup equity packages have a negative expected value for experienced executives, even before you factor in the career risk and stress.

​​The Math That Matters

Let's run the cold, hard numbers that startup cheerleaders don't mention.

Scenario A: Stay at BigCorp (Sr. Director Example)

• Current compensation: $800K annually ($350K base, $450K equity/bonus)

• 5-year earnings: $4 million (assuming flat growth, which is conservative)

• Work schedule: 50-60 hours per week

• Career risk: Low to moderate

• Stress level: Manageable

• Future optionality: High (both corporate and startup paths remain open)

Scenario B: Join HotStartup (Uplevel to C-Suite Example)

• New compensation: $400K annually ($250K base, $150K bonus, $500K "paper equity")

• Work schedule: 70-80 hours per week

• Probability of any meaningful equity payout: Less than 10%

• Probability of life-changing equity payout: Less than 1%

• Expected job tenure: 18-24 months

• Job search gaps: 6-12 months between roles

• 5-year earnings if you retain the role + hit the bonus (~10% probability): $2 million

• Career risk: Extremely high

• Stress level: Through the roof

• Future optionality: Severely reduced

You're trading $4 million in guaranteed earnings for maybe earning $2 million over the same period.

That's a $2 million opportunity cost for a very small shot at hitting it big.

But Even When You "Win," You Don't Really Win

Let's say you're one of the lucky ones. You joined the hot startup at Series B, got 1% equity, fully vested your stock, and the company gets acquired for $300 million.

Your equity is worth a $3 million windfall.

Sounds amazing, right?

Here's the reality.

After taxes, that $3 million becomes $1.5 million. Over 4 years at the startup making $400K annually, your total compensation was $3.1 million ($1.6M cash + $1.5M equity windfall).

Meanwhile, staying at BigCorp for those same 4 years at $800K annually would have netted you $3.2 million.

So even in this "success" scenario, you made $100K less than staying put.

And that's before factoring in the 80-hour weeks instead of 60-hour weeks, the constant stress, and the career risk you endured.

In other words, you risked your entire career, worked 33% more hours, dealt with constant uncertainty and stress, and your "life-changing" windfall netted you roughly what a solid corporate promotion would have delivered.

And that's in the best-case scenario where everything goes right.

Meanwhile, your corporate peers aren't sitting still.

They're getting promoted, building deeper networks, accumulating more valuable experience, and compounding their compensation growth year over year.

This is why I tell my executive clients—If maximizing earnings, reaching financial independence, and maintaining controllable career progression are priorities, startups are rarely the answer.

You're making a high-probability bet against yourself based on lottery ticket thinking.

"But Jacob, what if I'm the exception? What if this startup really is different?"

Here's the thing about exceptions—by definition, most people aren't them.

If compensation and money are most important to you, you should optimize your career for long-term success and predictable wealth building, not for lottery tickets dressed up as business opportunities.

The Psychology Behind the Urge

Let's talk about what's really going on when successful executives feel the urge to join startups.

Status Anxiety: You've plateaued at BigCorp and see peers getting promotions you think you deserve. A fancy C-suite title at a startup feels like validation, even if the company has 12 employees and burns through $2 million in runway every quarter.

FOMO: You keep reading about IPOs and acquisitions, calculating what you would have made if you had joined early. Every TechCrunch headline feels like a personal missed opportunity.

Boredom: Corporate life has become predictable. You could do your job in your sleep. Startups offer excitement and the illusion of greater impact. The chaos feels energizing compared to your quarterly business reviews.

Identity Crisis: You've started to question if you're really an "entrepreneur at heart" who's been stuck in corporate shackles. Maybe you're meant for something bigger, more meaningful, more... startup-y.

The Grass is Greener Syndrome: You romanticize startup culture. The ping pong tables, the casual dress code, the "we're changing the world" mission statements. It all seems so much more authentic than your corporate environment.

These are all understandable feelings.

I get it.

Corporate life can be suffocating.

That’s why I don’t do it.

But they're often flippant reasons to make career decisions that impact your family's financial security and your long-term professional trajectory.

The executives who make these emotional decisions often regret them within six months.

The novelty wears off quickly when you realize you're working 80-hour weeks for half your previous compensation while the founders argue about product direction and burn through Series B funding.

The "meaningful work" you thought you'd find? It's still work. Just with worse benefits, higher stress, and no job security.

The "entrepreneurial freedom" you craved? You're still reporting to someone—it's just that your boss is now 23 years old, raised $50 million based on a PowerPoint deck with AI in bold, and has never managed anyone before.

The psychological drivers that push executives toward startups are real. But satisfying them through career suicide isn't the answer.

When Corporate Life Legitimately Isn't Working

There are valid reasons to consider leaving a corporate role:

Genuine Ceiling: You've truly hit an immovable ceiling due to politics, restructuring, or skills mismatch. The next three levels above you are occupied by people with 20-year tenures and no plans to retire. You've been passed over for promotion twice despite strong performance.

Toxic Environment: Your mental health is suffering from a genuinely toxic workplace. We're talking about documented harassment, impossible workloads that are destroying your family life, or a boss who's actively sabotaging your career. Not just "my manager is kind of a jerk" situations.

Impending Disaster: You have insider knowledge that the company is headed for serious trouble. Mass layoffs are coming, the division is being sold, or the business model is collapsing. You can see the writing on the wall and need to get out before everyone else figures it out.

Golden Handcuffs Are Rusting: Your equity is underwater, bonuses have been cut for three straight years, and compensation has stagnated while your responsibilities have tripled. The "golden" handcuffs aren't so golden anymore.

But note what isn't on this list—boredom, title envy, curiosity about startup life, or reading too many LinkedIn posts about "entrepreneurial journeys."

Those fluffy LinkedIn influencers will be the death of us, I swear it.

Even in these legitimate scenarios, another established company is almost always a better next step than a high-risk startup.

If you're genuinely stuck at BigCorp, consider BiggerCorp, or DifferentCorp, or even SmallerButStableCorp. The goal should be to solve your immediate problem while preserving your long-term financial trajectory.

A startup should only be considered when you've exhausted all corporate options and you're prepared to treat it as a calculated risk with proper downside protection—not as an escape from corporate life.

Or if your work BFF got a hair brained idea and you’ll miss your proverbial water cooler partner in crime.

The difference between a strategic career move and career suicide often comes down to whether you're moving toward something better or just running away from something uncomfortable.

De-risk Your Startup Itch

There is one way you can test startup waters without career suicide.

If the entrepreneurial urge is eating at you, there's a way to scratch that itch without torching your professional reputation or financial security.

Enter fractional executive work—but not the way most people do it.

The Smart Approach (Not the Fractional Grind)

I'm not advocating for becoming a professional fractional executive juggling six clients and calling yourself a "portfolio career" consultant.

That's a different kind of career trap that creates its own perception problems. If you’re interested, comment below and I’ll put together an article about the fractional career trap.

Instead, use fractional work strategically as a testing ground while you're between corporate roles or exploring your next move.

Think of your career like a startup managing runway.

You need to extend your burn rate while building optionality. Short-term advisory work does exactly that—when done right—especially during a broader job search or complex career transition across functions or industries.

How This Actually Works:

You take on 1-3 advisory or short-term executive roles during transition periods.

You're not announcing these commitments on LinkedIn—you’ll give your network whiplash. Many executives accidentally build a fractional executive brand and then struggle to get back to an executive W2. You must be intentional.

You're strategically exploring while maintaining corporate optionality. You get to choose.

You get to peek behind the startup curtain without committing your entire career to one roll of the dice. Maybe the AI company has brilliant founders but an impossible business model. Maybe the fintech startup has real potential but a toxic culture. You discover this in months, not years.

You keep your tools sharp and your network active during what would otherwise be idle job search time.

Often the best fractional roles come from what starts as a full time hire, but runs into cost restraints, and becomes a fractional play with the option to renegotiate into full time later.

You also build leverage—you're the executive who has options, not the one desperately taking the first offer. You’ll gain deep insight into multiple business models, go-to-market motions, and new playbooks—and may even negotiate a premium like $500-$1000/hr for the privilege.

The Critical Optics Management:

This is where most executives screw it up.

They announce every short-term engagement like it's their new career. Six months later, they're explaining why they've "moved on" from three different companies.

Remember my piece on selective LinkedIn sharing? The same principles apply here.

Your LinkedIn stays corporate-focused: "Executive Leader" or "Strategic Advisor." You don't announce 4-month engagements that might not lead anywhere.

You must control the narrative.

Less is more when it comes to fractional work visibility. The goal is to explore opportunities, not to build a fractional executive brand.

The Exit Strategy is Everything:

This approach only works if you have a clear end goal.

Either you're returning to corporate with better information about what you want, or you're making a calculated commitment to one startup opportunity.

What you're not doing is becoming a permanent fractional executive grinding through multiple clients indefinitely. That's a different career path with different trade-offs and perception challenges.

The fractional approach should be temporary exploration, not a permanent lifestyle. Use it to de-risk your startup curiosity, then make a real decision about your next move.

This lets you satisfy your entrepreneurial itch without the career suicide of blind startup leaps.

You get information, maintain optionality, and protect your downside—all while testing whether startup life actually fits your reality.

Plus, a few extra irons in the fire never hurt anyone.

A Multi-Seven-Figure Success Story

Let me share a story that illustrates why staying corporate often beats the startup lottery.

About 3-4 years ago, I advised a Senior Director at a Fortune 500. They were doing well for themselves—roughly $800,000 annually—but felt that a change was in order.

The circumstances were exactly what you'd expect from the big industry titans.

Forward career momentum had stalled as all the folks above them had 20-year tenures and succession plans built for years. Plus, it gets old and boring.

Fortunately, they had multiple choices—a sign that they’re the real deal.

They could join an early-stage startup where their former manager and mentor had landed, or stay put to lead a new strategic project. The mentor couldn't see running the business without my client, which made the startup offer even more tempting.

Fortune 500 projects can take 3-5 years of commitment to get real traction. Not exactly the quick-hit excitement of startup life. And the project wasn’t even guaranteed yet.

We reviewed the possible outcomes and discussed the perception issues, the potential career death spiral, long-term earnings, liquidity chances, and all the rest.

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.

The decision took 4 months.

We worked together while it took months for the F500 project to gain a coalition of support and get approved. After running through all the scenarios, they chose to stay put and take on the project.

Here's what happened:

They had an incredible 18-month turnaround within the company. They got promoted to VP during that time—something that never happens at this particular F500. The promotion brought their compensation to $1.8 million average with upside to $2.4 million if they hit performance goals. And remember, these RSUs are valuable, consistent, and compounding.

Meanwhile, the startup route with their buddy would have netted closer to $550K annually after all was considered.

Don’t get me wrong—I would never scoff at making over a half million a year—especially doing something more fulfilling than F500 transformations—but that delta is too much of a chasm to ignore.

I debriefed with my client just a few months back. They're still in that VP role and expressed gratitude for the guidance to stay in this instance.

I'd be lying if I said these results were typical. Corporate projects don't always move that fast, and companies don't always reward success so generously.

But here's my point.

Why would you gamble an $800K salary and career stability for a minuscule shot at a startup lottery ticket when there are opportunities to create value right where you are?

Maybe they were lucky that they found a way to accelerate an outcome within the Fortune 500 landscape. But they made a much more calculated bet than their startup-bound peers.

They bet on their ability to execute within a system they understood, with resources they could access, alongside people they'd built relationships with over years.

The startup path would have meant betting on factors completely outside their control—market timing, founder competence, investor sentiment, and a dozen other variables that have nothing to do with their own capabilities.

3-4 years later, they're earning more than double their original compensation, building on the success they created, and still have the startup path available if they ever want to explore it.

Their mentor at the startup?

Still grinding through the early-stage challenges while my client built sustainable wealth through predictable corporate advancement.

You must maximize your current position of strength rather than gambling it away on someone else's dream.

If you’re going to risk your career on a startup—make sure it’s your startup. Founder gambles only.

If this article just saved you from a million-dollar career mistake, consider upgrading to paid. Next week's "Startup Meat Grinder" recovery strategies will be essential for anyone already trapped in the cycle. Upgrade to Paid

If You're Still Determined to Join a Startup

If after all this, you're still set on leaving corporate for startup life, here's how to protect yourself:

Negotiate a Soft Landing: Get 6+ months of guaranteed severance if things don't work out. You'd be shocked how many executives don't even ask for this basic protection. The startup world moves fast, and you need runway to land your next opportunity without desperation.

I suspect that negotiating severance will be a deep dive article that interests most of our readers. There is a systematic flow I’ve found that really works here. Drop a comment below 💬 if you want me to prioritize an article on winning severance negotiations.

Secure Real Equity Terms: Negotiate longer post-termination exercise periods—ideally 2-3 years, not the standard 90 days. Some execs have gotten 7 and 10 year windows too. Get acceleration triggers for both single and double-trigger events. Demand clear valuation metrics and anti-dilution protections. Most executives are too polite to ask the hard equity questions, which is exactly why they get screwed later.

Create Backstops: Maintain your network at established companies and keep an active "return path" cultivated with monthly check-ins. Don't burn bridges thinking you'll never need them again. The best time to strengthen corporate relationships is when you don't need them.

Be Brutally Honest About Due Diligence: Do actual due diligence on the startup. Check references not just of the founders but of people who've left—especially executives who departed after 12-18 months. Ask the hard financial questions most executives are too polite to ask: What's the real runway? What are the unit economics? What happens if the next funding round doesn't close?

Set a Decision Timeline: Decide in advance how long you'll give the startup experiment before you'll make a clear-eyed assessment of whether to stay or move on. Most executives get emotionally invested and keep extending their timeline indefinitely. Set your limits upfront when you can think clearly.

Most executives skip these steps because they feel awkward or "not startup-y."

That discomfort is precisely why you need them.

The right startup will respect you more for asking tough questions, not less. And if they don't respect you for protecting your interests, you definitely don't want to work there.

Remember: If you wouldn't approve this deal structure for your company, don't accept it for your career.

Better Alternatives for Executive Growth

If you're feeling stalled in your corporate role, consider these alternatives before leaping to a startup:

Internal Entrepreneurship: Create a new division, product line, or strategic initiative within your current company. You get much of the creative freedom and impact you're craving with significantly less risk. Many Fortune 500 companies are desperate for executives who can think and act like entrepreneurs while leveraging corporate resources.

Strategic Corporate Move: Join another established company in a growth phase where your experience is valued but you still have opportunities to build something meaningful. Think Series D startups that have proven product-market fit, or mid-market companies expanding into new markets.

Board Positions: Add board or advisory roles to supplement your corporate position and satisfy your desire for variety. You get exposure to different business models and challenges without risking your primary income. Plus, board compensation has gotten quite attractive for experienced executives.

Corporate Venture Arms: Many large companies have innovation labs or venture arms that offer startup-like environments with corporate stability. You get to work with early-stage companies and emerging technologies while maintaining your benefits and predictable compensation.

Acquisition Integration: Lead M&A integration efforts where you're essentially running a startup that your company just bought. You get the entrepreneurial challenge of scaling a business with the resources and backing of an established company.

New Market Entry: Spearhead your company's expansion into new geographic markets or customer segments. It's essentially a startup within a startup, but with corporate backing and resources.

All of these options preserve your compensation while offering new challenges and growth opportunities. They satisfy the psychological drivers that push executives toward startups—impact, learning, variety, and growth—without the financial suicide.

Finding Peace with Your Corporate Path

Look, I don't hate startups.

I owe my career to the opportunities they brought me. But there is a time and place for them in a career journey.

If you're a high-earning corporate executive, you've already won a game that most people never even get to play. The urge to risk it all on a startup lottery ticket is often more about ego than economics.

The most successful executives I know aren't constantly chasing the next role or company. They're not falling for get-rich-quick schemes dressed up in startup mythology.

They understand that real wealth and career satisfaction come from maximizing their position of strength, not gambling it away on statistical long shots.

They're playing the long game of career development, not falling for the quick-fix fantasy of startup glory.

The Grass Isn't Greener at Startups

It's just fertilized with different bullshit.

You'll trade quarterly earnings calls for daily funding crises. You'll swap predictable bonus cycles for equity that may never vest. You'll exchange seasoned colleagues for 23-year-olds who think "growth hacking" is a legitimate business strategy.

The problems don't disappear at startups—they just get dressed up in hoodies and called "pivots."

What Success Actually Looks Like

Real executive success isn't about predicting, finding, and joining the next unicorn before everyone else figures it out. It's about building sustainable wealth, maintaining optionality, and creating value wherever you are.

It's about being the executive who doesn't panic during market downturns because you've built a diversified career portfolio and financial foundation.

It's about having the confidence to walk away from bad opportunities because you're not desperate for the next shiny object.

You won’t find success—you must create success.

So if you get the startup itch—create your own, don’t join someone else's.

The Bottom Line

If you're going to make a move from your cushy corporate role, you better make damn sure you're moving toward something genuinely better—not just running away from something comfortable.

You better negotiate the hell out of that opportunity to protect your family, career status, perception, and anything else you're putting at risk.

Next week I'll share exactly how executives escape the startup meat grinder once they're trapped in it.

If you took a more aggressive and risky approach to your career and find yourself explaining multiple 18-month tenures in interviews, next week’s article will be essential reading.

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Stay fearless, friends.

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