Building Something from Scratch: As an engineer at heart, I miss coding and creating. Joining a young startup promised the thrill of building a product 0→1 instead of just advising or observing. The builder itch is real - there’s nothing like rolling up your sleeves and shipping features at 2 AM, powered by cold brew and pure adrenaline (trust me, I’ve been there).

High Upside (with a Dash of FOMO): Let’s be honest – seeing that Sequoia is backing a company triggers serious FOMO. 💸 Big-name VCs can signal a potential future unicorn. I had visions of meaningful equity in the next big consumer AI platform. What if this becomes the next WhatsApp or Instagram? I didn’t want to be the cautious guy on the sidelines if this rocket took off. The risk-reward calculus seemed to scream “go for it!”

Front-Row to Innovation: The startup was tackling a cutting-edge AI problem in consumer tech. As an Operating Partner I help portfolio companies, but joining a startup full-time meant being at ground zero of innovation - living and breathing one vision every day. That singular focus can be intoxicating: no more context-switching between dozens of portfolio updates, just one mission to pour my soul into.

The “I Still Got It” Factor: I won’t lie – part of me wanted to prove I could still hang in startup land. VC life is exciting, but you’re one step removed from the action. There’s a certain badge of honor in going back into the arena, leading a team as a builder/operator again. It’s like an ex-pro player coaching from the sidelines who misses playing on the field. The startup’s founders were practically courting me too – flattering my ego with “We need your skills to scale this.” Hard not to feel wanted and envision the heroic return to startup glory. 🦸‍♂️

Stability & Commitments: As an Operating Partner, I have commitments to my firm and our portfolio. I’ve built relationships with founders we back, and they rely on my support. Leaving abruptly felt like I’d be breaking a promise – not just to my colleagues but to the startups I mentor. Plus, my VC role comes with some stability (salary, a slice of carry, a roadmap for growth within the firm). Walking away meant potentially forfeiting unvested carry and benefits that I’d worked hard for. It was a classic head vs. heart dilemma: the adventurer in me craved change, but my practical side tallied up everything I’d lose by bailing out too soon.

Risk, Meet Data: Startups are inherently risky – we all know the mantra, but sitting on the investor side really hammers it home. We’ve all heard “90% of startups fail,” and the actual stats aren’t much rosier: ~20% fail in year one, and only ~50% make it past year five . Early-stage consumer AI is exciting, but also unproven – trends can fizzle and consumer behavior is fickle. As much as Sequoia’s backing impressed me, even top-tier VCs aren’t infallible. (Reminder: they’ve had legendary wins and backed their share of duds). A fat term sheet from a famous fund doesn’t magically erase product-market fit questions or execution risk. My inner voice asked: “Would you invest in this company yourself, at this stage, on these terms?” - A tough question, and tellingly, I couldn’t immediately say yes.

Moats & Hype Concerns: In the AI gold rush of 2025, I’ve seen how quickly today’s hot startup can become tomorrow’s commodity. With code and models so easily replicated, sustainable advantages are hard to come by. As I recently wrote, building has never been easier and tech gets copied at light speed . So what’s this startup’s moat? Sure, they had a cool demo, but defensibility was murky. In fact, one of my own investor brain’s favorite questions popped up: “What’s stopping another team of 10 brilliant engineers (maybe also Sequoia-backed!) from outbuilding us next quarter?” . It’s a bit meta, but I was essentially asking whether the startup I’d join could itself get disrupted by the next hype cycle. That thought gave me pause - nobody wants to be on a rocketship that could flame out because the idea is too easy to clone or the market shifts.

Role & Impact Considerations: This one was subtle: as an Operating Partner, I have a broad sphere of impact - I advise multiple startups, shape internal strategy, and wear many hats (tech advisor, recruiter, sounding board, you name it). Jumping to a single startup, I’d narrow my impact to one company’s success (or failure). Yes, depth over breadth can be rewarding, but I had to ask if this particular startup’s mission was so compelling that I’d trade the diversity of my current role for it. After a lot of soul searching, I realized I didn’t feel a deep personal mission alignment with the startup’s product. I liked it, thought it was clever… but I didn’t love it to my core. And if you’re going to weather the inevitable storms of startup life (the all-nighters, the pivots, the “oh no, we’re almost out of runway” moments), you need passion on overdrive for that product. My enthusiasm here was lukewarm, and that’s not a great sign when considering a life-consuming venture.

Lifestyle & Personal Life: Finally, the good ol’ work-life reality check. Venture Capital can be intense, but let’s get real: startup life is equally intense with a lot more risk, I’m less inclined to embrace the “sleep optional” ethos again for no upside. As an investor/operator now, my schedule can get crazy, but it’s at least somewhat self-directed. Joining a small startup, I knew I’d be signing up for firefighting 24/7. Was I ready (or my family ready) for me to disappear into a code cave or endless user acquisition war? I had to admit: not really. Sometimes balance (or a semblance of it) and sanity are undervalued when shiny opportunities knock.

Check Your True Motivation: Ask yourself honestly why you’re tempted. Is it FOMO from the hype train, ego boost of being wanted, or genuine passion for the product/mission? If it’s mostly FOMO or ego, pump the brakes. The grind will quickly burn through superficial motivation.

Do a Risk/Reward Reality Check: List out what you’re giving up versus what you could gain. Factor in personal finances, family, health, and yes, data on startup survival. Dreams are great, but don’t ignore the odds and opportunity costs (that steady paycheck and sleep schedule are worth something!). If the potential reward truly outweighs the risks for you, you’ll feel it clearly, and if not, you’ll see that too.

Evaluate the Startup like an Investor: Even if you’d be joining as an employee, put on your VC hat. Would you fund this company? Is there strong evidence of product-market fit? A moat or unique edge? A plan for the known risks (tech, market, etc.) ? Be skeptical and objective. If red flags pop up in diligence, don’t ignore them just because the opportunity is exciting.

Know Your Personal Non-Negotiables: It helps to define what you must have in your work-life. It could be a certain level of work-life balance, a mission you deeply believe in, or a role that fits your long-term career story. In my case, I realized I’m not willing to jump unless the startup truly lights my soul on fire and fits my life’s bigger picture. Your criteria may differ, but be clear on them. It makes the go vs. no-go decision much easier when an offer comes knocking.