Navigating Career Risks in Startups

This software engineer left their job to join a new, great-paying role at an up-and-coming startup, only to be left unemployed and without any backup....  Behind every career move like this, there are people depending on you, family, bills, maybe even loans. And then to lose it all with a 2-week payout, it’s a tough hit, both emotionally and financially. It’s disappointing to see a company move forward with hiring, onboarding, and formalities only to back out last minute, citing internal restructuring. Startups are unpredictable, yes, but the responsible thing is to be upfront. If there’s any doubt about headcount or funding, candidates deserve transparency before they make life-changing decisions. It’s not just about a contract, it’s about basic decency. For anyone considering a switch to a high-growth, high-risk startup (or even a “dream” role): >>> Always ask about runway and funding. Get clarity on the startup’s financial health. If possible, ask directly about recent funding rounds or stability. >>>  Request everything in writing. A formal offer letter, start date, and contract terms, don’t settle for verbal commitments or vague emails. >>>  Don’t resign before you have a signed, official offer. And even then, try to negotiate a buffer period if you can. >>>  Connect with current employees. Try to get a sense of recent churn or last-minute surprises. Red flags are often shared off the record. >>>  Keep a backup plan. Have some savings or a backup opportunity, especially if you’re the sole breadwinner. >>>  Read between the lines. If communication feels rushed or you see new people suddenly joining company channels, trust your instincts and ask questions. No career move is without risk. But nobody should have to pay for a company’s lack of transparency with their livelihood.

7-10 years into your career is the most dangerous time to get comfortable. On paper, you’re doing well. Solid salary. Steady progression. Good reputation at work. But deep down, you feel it - the plateau. You’re busy every day, but you’re not moving forward. Your growth curve has flattened, and you don’t know how to kickstart it again. This is the mid-career fork in the road I see every week. You’ve proven you can succeed in structure. Now you’re wondering: “What would happen if I bet on myself in a different environment?” And it usually comes down to two choices: Option A: Stay on the corporate treadmill. Keep collecting the paycheck. Keep building someone else’s vision. Stay comfortable, but accept that you’re trading excitement for "stability". You risk one day waking up wondering where the last 10 years went. Option B: Step intentionally into startups. This is where the growth accelerates - where your impact is visible, and your decisions actually shape outcomes in real time. If you’re considering that shift mid-career, here’s how to make it work: 1. Translate corporate scale into startup scrappiness. The systems, budgets, and teams you’ve worked with are valuable, but only if you can show how you’d drive similar outcomes with fewer resources. Show that you can adapt, not just lead. 2. Position your experience as leverage, not baggage. Don’t frame it as “10 years in corporate.” Frame it as “10 years of pattern recognition and proven results I can apply in a leaner environment.” That’s what founders are buying. 3. Pick the right stage. You don’t need to join a five-person seed startup to grow. Growth-stage companies (Series B/C) are often the sweet spot - still scrappy enough for impact, but structured enough to value your experience. 4. Audit your risk profile. Maybe you’ve got a mortgage, kids, or other commitments. That’s fine. Just be strategic. Focus on startups with funding security, strong backers, and clear market traction, not lottery tickets. Because at this stage of your career, the real risk isn’t making a move. The real risk is standing still. You don’t need to burn everything down. You just need to start betting on yourself again.

This might be controversial, but I’m going to say it anyway. If you’re about to join a startup or scale-up and you’re only looking at the comp package and job title… you’re setting yourself up for regret. The smartest operators I know use one simple filter before they say yes. It’s called the 3 Ps. And here’s how it works: 1️⃣ People - Work with people you respect and can learn from. - If you’re the smartest person in the room, that’s a problem. - The people you join today shape your opportunities tomorrow. 2️⃣ Product - You should be genuinely excited about what the company is building. - If you wouldn’t personally use it, sell it, or stand behind it, think twice. - Conviction matters when things get tough. And they will. 3️⃣ Potential - Look beyond the pitch deck. - Is the market big enough? Can this company scale? - Will your role stretch you and open new doors later? - Make sure you’re chasing growth, not just a paycheck. The truth is, joining the wrong team can stall your career faster than any bad boss ever could. The hype, the perks, the big titles won’t matter if the people, product, and potential aren’t right. Choose wisely. If you’re evaluating a new role or startup opportunity right now, remember this framework. It has saved me more than once. So ask yourself: When things go south, will you still believe in what you joined for? Let me know your thoughts in the comments below.

Everyone talks about the risks of starting a company. No one talks about the risks of getting too comfortable in your current job. “When is the right time to start a company?” Someone asked me this recently, and it took me back to the moment I chose to go all in on my founder journey. When I left LinkedIn to go full-time on a startup, I treated it like evaluating startup ideas and asked, “Why now?” Particularly, I asked two questions: -- 1/ WHY NOW, NOT EARLIER? What was I waiting for? - I needed my visa situation squared away. Check. - I needed enough personal financial runway to at least give a fair shot for a year. Check. - I was looking for the right collaborator. Check. I unlocked the right to start building full-time. Everything I added after this list that was just an excuse. -- 2/ WHY NOW, NOT LATER? Why would waiting be worse? - Golden handcuffs were real. The longer I stayed at my comfy job, the harder it was going to be to leave. - I had no dependencies, no mortgage. Making the leap is easiest now more than ever. - I was plateauing. My growth stalled & I didn’t like that. That was the scariest part: I was starting to trade growth for comfort. And that’s when I knew it was time. -- This framework isn’t just for starting a company—it applies to any big, scary career move you’ve been wanting to make but keep putting off. The kind that feels risky now, but you know deep down will be worth it. So if you’re sitting on the edge, asking when... Also consider asking: → Why not earlier? → Why not later? Your answers won’t just give you clarity. They’ll show you if waiting is the real risk. -- TAKEAWAY If staying feels safe but your growth has stopped—then waiting is the bigger risk. Make the leap when your risk of not doing it outweighs the risk of staying.

In 2016, I received a flattering promotion offer. My peers thought I was CRAZY when I said 'No'. I was at the height of my career in finance. I’d just closed a big M&A deal and earned the confidence of management. An opportunity to go to Geneva 🇨🇭 to lead an investment team was offered. Numbers wise it was a very attractive offer. But, I chose not to take it. Under the surface, past the dollars and cents… I wasn’t happy, something my wife noticed over time. Sometime later in that period, my late father passed away. That, combined with my mental state at the time, made me pause. I had to reevaluate my priorities. Is this really what I want to do for the rest of my life? These are the lessons that helped me decide: ❇️1. Trust your gut instinct. I looked at my past investments. Realized that I loved working with teams who disrupt the norm. I loved the energy of startups that could innovate and do better. Coincidentally, those teams are growing in Southeast Asia. These factors aligned and made sense. It was a firm belief, a gut instinct.  Though scary, I knew this was the right path to take. If I could be an entrepreneur, why not do it in my home country? 🇸🇬 ❇️2. Put values first The entrepreneurial itch was always there. But I didn’t know what to do next.  After making up my mind, meeting Murli Ravi was the golden key. He helped precipitate a lot of these discussions. Before we even thought about venture, We aligned on values: - Value Creation - Fairness and Integrity If you want something to last, you need to get your values aligned. ❇️3. Build a strong relationship with risk. My career history was working for big companies. To take a risk and establish my own was nerve-wracking. I was never comfortable when I took the plunge. I only got settled when I went through the ups and downs of entrepreneurship. In truth, even being employed comes with risks. Now, if I ask myself, “Is this really what I want to do for the rest of my life?” The answer would be a resounding YES. ----- Plenty of decisions can feel ‘Pivotal’, But life and your career is a long journey. Money isn’t everything and it’s worth thinking about your next move carefully. What do you think? 📸 Me in discussion at one of our Tin Men Capital events. One of the perks of work, meeting amazing founders.