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Financial Red Flags Every Founder Should Avoid

Financial Red Flags Every Founder Should Avoid

Early-stage founders need every possible advantage to distinguish themselves. That means knowing your business inside and out

Scott Cormier
3.23.23
In article:

Early-stage founders need every possible advantage to distinguish themselves. 

That means knowing your business inside and out — and understanding how your north star metrics and KPIs drive you towards specific growth goals.

Anne Dwane, Co-Founder and General Partner at Village Global, agrees. Her early-stage VC firm funds tech-driven companies around the world, with backing from LPs like Anne Wojcicki, Bill Gates, Mark Zuckerberg, Reid Hoffman, and Sara Blakely. 

The Puzzle team sat down with Anne to go deep on how founders can use their numbers for outsized success across growth stages. Below, we unpack: 

  1. Why every early-stage founder should know their numbers
  2. What are investors’ financial priorities during early-stage diligence
  3. How founders can use investor updates to their advantage
  4. Red flags to avoid with your metrics and financials

“Not knowing your numbers is paralyzing. Clarity and focus are so important in startups because there's already a lot of chaos. Add in an adverse macroeconomic environment, and the stress levels go up.” 

TLDR:

  • Investors care more about how you think about your numbers than the numbers themselves.
  • The three financial red flags to avoid: no numbers at all, vague answers about them, and tracking too many at once.
  • Your product needs to be 10x better, cheaper, or faster than alternatives to change customer behavior.
  • Investor updates are a tool for internal alignment as well as external reporting.
  • Puzzle sat down with Village Global's Anne Dwane to unpack how founders can use their financials to build with more clarity.

Why this matters more than ever in 2026

The funding climate has shifted dramatically. Early-stage VC deals are up: Q1 2026 saw roughly 1,800 early-stage deals worth $41.3B, a 40%+ increase year-over-year, according to Crunchbase data. But access to that capital has a new price: financial rigor. Investors now lead diligence with burn multiple, CAC payback, and NRR, beyond growth rate alone. On burn multiple specifically, David Sacks of Craft Ventures — who coined the metric — benchmarks anything below 1.5x as "Good" or better. The era of funding grand visions on faith alone is over.

That's what makes Anne's framework so timely. The advice below is more than good practice: in 2026, it's table stakes.

Why every early-stage founder should know their numbers

In Anne’s words, “Cash is oxygen for little businesses, so they can’t run out of it.” When you run out of money, you run out of time to figure out your business. 

By extension, mastering your finances will maximize your time to build a stellar business. This is a core capability, no matter the economic climate. 

Founders can start interrogating their numbers by asking questions like: 

  • Which factors drive our business? What drives revenue, costs, and usage metrics that indicate adoption and retention?   
  • Can we variabilize costs so that they’re tied to revenue and/or usage?  This makes costs into investments into metrics that matter.  
  • What experiments can we run quickly and cheaply to gauge what works? 

How do accounting & bookkeeping directly impact growth? 

According to Anne, “Entrepreneurship is creating value beyond resources currently controlled.” 

To make the most of your resources, you must know what you have and what it could lead to. This is where the processes of startup accounting and bookkeeping are so important. A concrete example: a founder tracking burn by department in real time can spot that engineering costs are outpacing revenue growth — and redeploy that budget toward a sales hire before runway shrinks to a crisis point. That decision only happens if the books are current. Without it, you're guessing at month-old data while the business moves on.

With this, founders should reframe how they think about spending. Think of costs as investments to drive company metrics. 

When your financials feed your operating models, it hugely simplifies the business. 

Investors’ financial priorities during early-stage diligence

Village Global invests very early. And Anne finds that what’s more important than the actual numbers is how a founder thinks about the numbers. 

After all, they’re searching for founders who seek to create overwhelming value, then have a plan on how to capture a piece of that. 

  • A product that is only slightly better is unlikely to change customer behavior. 
  • Products must be 10x better, cheaper or faster than alternatives and substitutes to gain adoption and usage (a benchmark popularized by Peter Thiel and others in venture).

To create a compelling case for their product, founders need to: 

  1. Understand market size and walk investors through the scale of opportunity
  2. Explain how they’re going to create measurable, outsized value – and capture a portion of that (which will be much higher than the cost to provide the product or service in the long run)

Often, founders are identifying and tackling a market that doesn't quite exist yet. Even then, they can point to concrete data that shows the opportunity is real — for example, a TAM growing at 30%+ annually, analyst projections placing the sector at $X billion by 2027, or regulatory and demographic shifts that make the status quo untenable. 

“The big thing we’re looking for is 10x faster, cheaper or better than alternatives or substitutes. That kind of overwhelming value prop makes your consumer really want to adopt. Over time, you should be able to capture a portion of the value you create…and that exceeds your costs to produce your offering.” 

How to take advantage of the investor update

Here’s a tip from Anne: Founders can use investor updates for their team as well as for external stakeholders. 

At a startup, if you don’t have a plan, everything seems like progress. Founders always have a million things to do. However, the truth is: Doing the right things is more important than doing many things “right”. So, investor updates are an opportunity to zoom out and gain valuable perspective. When writing an update, ask yourself: 

  • How are our actuals trending vs. our plan? 
  • What have we learned?  What will we do more of, less of, or do differently? 
  • Where are we making real progress on what matters? 

Knowing your burn rate and runway as you ask these questions will allow you to recalibrate. 

  • If you’re close to the target, optimize. 
  • If you’re exceeding target values, that’s great. You can raise targets. 
  • If you’re way below target, dig in.  Do we need to rethink our approach?  Should this even be a goal? 

Beyond the numbers, investor updates are opportunities to: 

  1. Stay top of mind for stakeholders — It’s a scalable approach to maintaining contact with existing investors, prospective investors, future hires, early champions, and more. . 
  2. Share progress with the team internally — “That kind of transparency unleashes productivity and ingenuity,” says Anne. 
  3. Ask stakeholders for advice or help: You don’t have to follow it, but tapping your startup’s support network for diverse perspectives is smart. 

“Making time for your team to reflect on the actuals vs. the plan over time and to codify that can be really helpful. It’s very easy in startups to be overwhelmed by daily activities. You have to make the time to step back and reflect on the drivers of the business.  This is powerful - you don’t need to do everything if you get the big drivers right.” 

Avoid these red flags when handling numbers & finances

Anne lists the red flags to look out for in your numbers: 

A startup founder sitting at a minimal desk, looking stressed and overwhelmed, surrounded by floating abstract charts and graphs with warning symbols, red warning indicators, and financial dashboards showing chaotic data. The scene uses a modern flat illustration style with a warm color palette of deep reds, oranges, and dark navy blues. No text, no letters, no numbers, no words anywhere in the image.
  1. Not having any numbers — This is easily the biggest red flag. 
  2. “Hand waving” through the numbers — This is second only to having no numbers at all. 
  3. Having too many numbers — If you have too many priorities, you really have none. 
Red FlagWhat It Looks LikeWhy It's a Problem
No numbers at allFounder can't cite key metrics when askedThe biggest red flag: signals a lack of business awareness
"Hand waving" through the numbersVague or evasive answers about financialsSecond only to having no numbers — erodes investor trust immediately
Too many numbersTracking every possible metric without clear prioritiesIf you have too many priorities, you really have none

Having the most important numbers available allows you to look past the complexities. Real-time accounting software keeps those numbers current so you're never caught off guard. 

Too many numbers — or too few of them — will hinder you. 

Make sure to avoid this financial mistake

In Anne’s experience, the biggest mistake a founder can make is overconfidence. 

She tells us, “The only advantage a startup really has is to be a learning machine.” You should eagerly learn about your customer, your capabilities, and so on. If self-confidence gets in the way of being experimental and curious, that is a problem. 

Yes, founders should have the confidence to form hypotheses and run with them. 

But that confidence should stem from trust in your team’s ability to figure things out — not from thinking you have all the answers. 

“The good news is that big ideas don’t cost more than small ideas. It’s really a strategy of saying, ‘Here is the big vision. And this is the path to find how to get there in a responsible, measured way.’” 

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