By Kevin Berardinelli

I get to spend a lot of time observing founders and where they focus. Mostly, they look to the next revenue goal, the next round, the next big account. Few focus on how their business might die. Perhaps obviously! But maybe they should—that’s what famed investor Charlie Munger used to do.

“All I want to know is where I’m going to die so I’ll never go there,” he often said. And even though I’m an eternal optimist, I’ve learned to do the same to help founders see hidden threats. Because when you invert your thinking to view scenarios in the reverse—in the negative—you may see things you missed.

Sometimes, it’s the only way to spot the deadliest time traps.

Let’s explore this idea through examples and ways to apply it to the five go-to-market (GTM) areas where I see startup founders trip up, often through no fault of their own.

I’ve spent 15 years of my career in GTM roles at startups and in portfolio support roles at early-stage investment firms where I’ve worked with over 100 companies. I studied physics and math but also enjoy singing, painting, and writing poetry. I love to see the world from multiple perspectives, often lightheartedly. Today, I help Point72 Ventures founders maximize their potential for success by doing the same.

Let’s look at where founders can accidentally waste their time

Some companies might engage prospects who don’t need their products. Some might call the right prospects but ask the wrong questions and never learn their real issues. Some might retain unprofitable customers and waste dev cycles on unreasonable requests. Some might act contrary to their own brand promises in ways that are obvious to customers.

But those founders might never know until it’s too late. This is one of the great startup dilemmas, even for veteran operators: Time is a precious, finite resource. It is non-renewable and non-transferable. The clock is always ticking—every useless moment is gone forever.

But it’s hard to know that you’re wasting time in the moment—it’s often only clear after.

That’s why I think it can help to flip the way you prioritize your time. Instead of deciding where to spend it (abundance thinking), also think about where it would be wasted (inverted scarcity thinking). Because I contend that the startup journey isn’t just about what you do, but also about what you selectively don’t do.

The startup journey isn’t just about what you do, but also about what you selectively don’t do

Take the design software startup InVision (no affiliation). Once valued at $2 billion, it will shut down operations this year. Not sell. Shut down. (After selling off one of its business units last fall.) That’s how quickly they were eclipsed by their competitor Figma. In an X (formerly Twitter) thread, the co-founder and former CEO explained the company invested time in the wrong areas, and when the right areas became clear, it was too late.

Ask yourself how you could face a similar competitive scenario. What are all the ways another vendor could corner you? Some of the brightest minds (like Charlie Munger) think like this naturally, but for most of us, it’s a learned skill. Shall we give it a try?

→ Direct thinking: Let’s get to $1M ARR by the end of the year

This sounds like a reasonable goal. So easy, right? With this thinking, a founder might spread their time across a wide variety of opportunities and hope the wins accumulate. But 3-6 months later, they might be off-track and curious. Why didn’t it all add up? They missed something important.

→ Inverted thinking: What could we do to ensure we earn no revenue this year?

Well, we could:

• Talk to people with no tech budget.
• Talk to people without the authority to decide.
• Talk to companies with a 13-month sales cycle.
• Build flashy features that don’t convince the real economic deciders.
• Drive up lead volume without regard to close rates.
• Confuse logos for dollar signs.

With this new thinking, they’d probably tighten up their qualifications. The very real fear of failure might convince them to conduct more thorough prospect discoveries and keep looking for the right leads, not settle for just any leads. I bet they’d prioritize more ruthlessly.

“Many problems can’t be solved looking forward … [they] are best solved when they are addressed backward.” – Charlie Munger

Of course, it’s not always clear what’s going to be a waste of time. (Wow, wouldn’t life be different if we knew for sure?) That’s why I’d advise categorizing the result of this brainstorming using the diagram pictured, which makes deciding easier.

When you avoid things that will likely waste your time, you free yourself up for more valuable things that won’t.

And before we go too far, let me add, this is not about saying you should be totally risk-averse. Founders often need to move fast and take smart risks. Inverted thinking is simply about weighing your risks and betting on more gray-area risks than red-area ones. Also, inverted thinking is not about always being negative. It’s about learning to consider the inverted worldview tactically, then turning it off. It’s learning to ask, “Wait, before we proceed, what if we invert our thinking on this?”

Now let’s apply it to the five GTM areas that can save you the most time—with five questions I like to ask.

1. What are the primary ways we will fail as a business?

It might seem painful to ask, but I think it’s quite useful. One of the things venture investors can do when investing in a company is conduct a “pre-mortem” with the founders to talk about what might go wrong. When we have conducted these in the past, we found that rather than worry the founders, we see it decrease the temperature in the room. Suddenly everyone can be honest. Founders can stop trying to “impress the investor” and we grow closer. Many are relieved that we don’t expect them to pretend to be forever optimists, and with that, we can plan ways to mitigate their greatest fears. We ask, what can we do as a firm to assist and augment in these areas?

Here’s a hypothetical example of a pre-mortem:

2. Who’d be a truly awful customer for us?

Startups are often so eager for customers, some happily take on the wrong ones, and then do gymnastics to make the product fit. Not all money is created equal. Some money is more expensive than other money because some customers are more demanding and can distract founders from profitable growth.

The difficult thing, but potentially right thing, is to keep searching for true product-market fit with the right product in the right market.

This is why I think founders should also build a non-ideal customer profile and keep everyone at the company accountable for disqualifying these prospects from their funnel. People may laugh. But it’s actually very useful.

3. What could really slow down our deals?

Many founders naturally think about accelerating deals. But what things are sure to slow them down? Are founders looking for and addressing common speed bumps and potholes? I like to encourage them to identify those deal velocity risks early and to get ahead of them.

For example, when customers grow confused, they tend to stall their evaluation. A founder can ask, “What could we do to really confuse our customers?” Then act on the results:

• The pricing is not entirely clear → User test and simplify.
• #1 objection is “Not right now” → The CEO distributes a “perfect response” voice note.
• The brand is unclear → Refresh positioning, messaging, brand assets.

In my experience, startups without a clear brand tend to confuse their biggest prospects. Those evaluating committees can get tied up asking, “But do they serve companies like us?” Investigate not only where your brand is helping you, but where it’s not helping or perhaps working against you. (This is especially important since in one study, 84% of buyers purchased from the first vendor they spoke to. I believe a good brand helps startups get noticed earlier.)

4. Who would NOT be a good fit for our sales team?

A bad hire isn’t just a financial drain; it’s also a time and culture drain. Yes, a founder can see all the ways a prospective account executive hire might work; they have an impressive record of exceeding quota. But how might they fail? It’s a bummer to ask, but useful.

Perhaps in asking this, a founder realizes that in their prior role, this prospective hire had lots of support from marketing and a well-trained business development team cold-calling into their territory. That new hire won’t have that support. Instead, they’ll be hacking together pipeline while the founder tests the pricing. Is the recruit agile enough? Emotionally ready to do things they may think are beneath them? Now, that founder can develop much better interview questions.

It can also help the startup design a much stronger interview process. They can create tests for those major red flags. For example, let’s say their top value is to be “customer-first.” Who’d be a terrible hire? Naturally, someone who:

• Hogs the mic and rambles.
• Asks few questions.
• Shows little curiosity.

Fortunately, those are easy to test for. That startup can make a point of sharing facts, but not explaining them. They can see if prospective hires dig to discover.

5. Where should we NOT spend any time and energy this year?

As the InVision example shows, development time is a precious resource and founders must devote it to the areas that matter most to their customers and profitability. They must identify the essential features to build while they backlog the less immediately essential ones.

I encourage founders to empower everyone in the company to practice inverted thinking and openly name distractions. Set SMART goals (specific, measurable, achievable, relevant, time-bound) and hold your teams to them—a goal that isn’t SMART is a wish.

Ask: How might we totally mis-build the product this year?

• Build features the customers say they want but don’t actually need.
• Build features on unit economics that don’t make sense.
• Fail to prioritize and select too many key features.
• Fail to build what 4 in 5 of our right-fit customers are asking for.
• Build infrastructure for plans that don’t materialize.
• Focus on new things rather than improving usage metrics on existing ones.

If you aren’t impressed by the number of tasks in your backlog, you probably aren’t being ruthless enough.

Negative thinking leads to positive outcomes

Again, don’t think I’m encouraging you to view the whole world through the lens of disaster. Just that you may be able to train your brain to spot all the wasteful assumptions that may come with always thinking optimistically. Too much of any good can be harmful—either thinking optimistically or pessimistically—and inverse thinking is just another tool. One that I believe can help founders avoid wasting time, pivoting unnecessarily, and making common GTM mistakes.

And you don’t have to be Charlie Munger to practice it. For as he famously said, “Knowing what you don’t know is more useful than being brilliant.” 🙃

This is not an advertisement nor an offer to sell nor a solicitation of an offer to invest in any entity or other investment vehicle.  The information herein is not intended to be used as a guide to investing or as a source of any specific investment recommendation, and it makes no implied or express recommendation concerning the suitability of an investment for any particular investor.  The opinions, projections and other forward-looking statements are based on assumptions that the authors’ believe to be reasonable but are subject to a wide range of risks and uncertainties, and, therefore, actual outcomes and future events may differ materially from those expressed or implied by such statements.  Point72 Private Investments, LLC or an affiliate may seek to invest in one or more of the companies discussed herein.