Risk assessment is a critical component of successful investment strategies. This article delves into expert-backed approaches for evaluating and managing risk in various investment scenarios. From balancing instinct with structured thinking to pivoting quickly when investments falter, these insights provide valuable guidance for investors seeking to optimize their decision-making process.

• Balance Instinct with Structured Risk Thinking
• Pivot Quickly When Investments Go Awry
• Structure Large Investments as Testable Bets
• Use Data-Driven Approach for Risky Campaigns
• Manufacture Your Own Products Strategically

Balance Instinct with Structured Risk Thinking

There was a moment when we were considering a substantial investment in an early-stage fintech startup. The technology was promising—solid team, strong MVP—but they hadn’t nailed product-market fit yet. The uncertainty wasn’t just around the market; it was also the founder’s lack of experience with scaling. As CFO, I knew we had to go beyond the spreadsheet. I brought in one of our team members to do qualitative due diligence—customer interviews, digging into churn reasons, founder mindset. Numbers give clarity, but context gives confidence.

We built a risk matrix that didn’t just assess the usual financial KPIs but also mapped operational readiness and team resilience. I remember spending a weekend running downside scenarios, asking myself not “How likely is success?” but “How bad is failure?” That’s where a lot of investors get it wrong—they get caught up in TAM and forget to consider survivability.

In the end, we went forward but structured it as a convertible note with clear milestones. What I learned was that gut feeling isn’t fluffy—it’s built from pattern recognition over time. And when you combine that with structured risk thinking, you can take bold steps without being reckless. At Spectup, we’ve used that same approach to guide our clients when they’re hesitating on investments or partnerships—balancing instinct with intentional frameworks.

Niclas Schlopsna
Managing Consultant and CEO, spectup

Pivot Quickly When Investments Go Awry

“The Time I Had to Fire the Entire Dev Team, Mid-Build”

One of the hardest investment decisions I’ve ever made came after my CFO years when I was funding my own startup. We had invested heavily in a dev team to build what would later become the backbone of DomiSource. I had mapped out the burn, we tied our milestones to releases, and I did all of the classic CFO modeling. It should have worked on paper.

But four months in, it became clear: the team wasn’t aligned. Missed sprints, bloated architecture, zero accountability. I had to decide—do I double down and hope it turns? Or do I pull the plug and lose four months of progress?

I approached it like I used to in finance: take away the emotion and look at what it would cost to continue. Not just financially, but the opportunity cost of bringing forward bad code and bad culture. So I fired the entire team, and we started from scratch. I hired differently. I created sprints with ownership, not just output. Within 60 days, we were back on track and, honestly, stronger for it.

What did I learn? The longer you let a misstep linger, the more expensive it becomes. Whether it’s your money or someone else’s, the real job is knowing when to pivot without flinching. Good CFOs don’t just manage capital; they make hard calls before they’re obvious.

Karen Watts
Founder and CEO, DomiSource

Structure Large Investments as Testable Bets

Last year, I approved a major investment in rebuilding our core product infrastructure, despite not having full clarity on how customers would respond. The risk was that we’d spend six figures without a guaranteed return on investment (ROI). I approached it like a portfolio manager: I split the investment into three phases, each tied to specific usability benchmarks. If users didn’t respond well to Phase 1, we’d halt the rest. I also worked with our CTO to create a “reversibility” plan—essentially, how easily we could roll back changes. The biggest lesson? Uncertainty isn’t the enemy—rigid thinking is. By structuring the investment like a set of small, testable bets rather than a single leap, we reduced exposure while still moving quickly. That mindset has completely changed how I evaluate large expenditures today.

Nikita Sherbina
Co-Founder & CEO, AIScreen

Use Data-Driven Approach for Risky Campaigns

Six months after we landed in Malta, we were growing 30% MoM, but only early adopters knew the brand. Then the pitch landed: our QR code on 200,000 milk cartons from the island’s biggest dairy. Price tag – €18,500, nearly 40% of that month’s “play money.” Risky? Yes. Chance to sit in every fridge on the island? Huge.

How I approached it:

Portfolio lens: Plotted every channel on a CAC x payback matrix. Milk fell into the high-risk / low-cost quadrant. Green light only if we’ve locked down the risks.

Back-of-napkin economics: 200k cartons x 3 looks each = 600k views. At 0.35% conversion – 2,100 installs. User LTV €9 -> break-even. Anything above is bonus.

Stress test: Historical QR data said 74% chance we at least break even. Worst case is a straight €18,500 hit.

Safety pins:

– 50% up-front, 50% after proof the cartons are on shelves.

– Unique UTM in the QR to isolate performance.

– Kill rule: CAC > €12 by week 4 – shut down.

Governance: Sent a two-page memo with the numbers to founders. Numbers > emotions; unanimous yes.

Outcome – 6 weeks in: 2,460 installs, CAC €7.52 (-24% vs blended). We secured an exclusive slot for the rest of the year at 15% cheaper CPM. Milk became our lowest-cost offline lever.

Takeaways:

– Every spend is an option, not a bet.

– Kill the campaign on paper before it kills your budget.

– Exit rules get written the minute you enter.

– Hard numbers make even the wildest ideas board-friendly.

The €18,500 risk bought us awareness, data, and unlocked another gear for growth. Run the numbers cold, and always keep a finger on the STOP button.

Aleksandrs Tuls
Co-Founder, Rozie

Manufacture Your Own Products Strategically

When we started Bestonlinecabinets in Los Angeles, we frequently heard the advice that we should stop relying solely on cabinets from other manufacturers and dive into producing our own. It was a significant pivot that came with a lot of uncertainty, but after two years of careful planning, we made the decision to invest in our own custom cabinetry factory in China in 2014.

To approach the risk assessment, we conducted thorough market research to gauge demand and analyze our competitors. We also evaluated our financial projections and considered the potential return on investment. This process involved crunching numbers, speaking with industry experts, and gathering insights from our existing customer base.

What I learned from this experience is the importance of balancing data-driven decisions with intuition. Investing in manufacturing was a leap, but it ultimately allowed us to control quality and pricing, leading to the opening of our second factory in Vietnam in 2018. This expansion has enabled us to offer our customers high-quality cabinets at competitive prices, proving that calculated risks can lead to significant rewards.

Josh Qian
COO and Co-Founder, Best Online Cabinets