The riskiest thing you can do
You raised millions to swing for the fences. So why are you bunting?
You, a venture-backed founder: Just raised $10 million to change the world. Six months later, you're arguing over button colors in Figma.
I wish I was making this up. But this is literally Tuesday at most venture-backed startups.
Somewhere between the pitch deck promising to "transform an entire industry" and actually running the company, something weird happens. Founders who convinced sophisticated investors they could build the next big thing start acting like they're managing a local pizza shop. Optimizing. Testing. Incrementing. Playing it safe.
You took venture money. You signed up to swing for the fences. So why are you bunting?
What playing it safe actually looks like
Let me paint you a picture of what "safe" looks like in 2025.
You know your signup conversion rate improved 0.8% last month but you have no idea what your biggest competitor is working on.
Your team spent more time in Slack last week debating the hero image than they did talking to users.
You can tell me your CAC down to the penny but you cannot tell me why your best customers actually bought.
You've run 47 A/B tests this quarter but haven't talked to a user in 6 weeks.
The metrics look decent. MAU is up and to the right. Conversion rates are improving. The investors aren't panicking yet.
But nobody gives a damn.
Fear is running the show. Fear of looking stupid. Fear of wasting money. Fear of building something nobody wants. So instead of building something remarkable, you retreat into the comfort of competitor research and best practices and "data-driven decisions."
The real problem? You're optimizing for investor updates instead of customer outcomes. Every monthly report needs to show progress, so you focus on metrics you can move instead of things that actually matter. It's easier to report "improved email open rates by 12%" than "we're completely reimagining our approach to the problem."
The irony is thick enough to cut with a knife. You convinced investors you could see around corners, then spent your runway staring at spreadsheets.
The math doesn't lie
Let's get rational for a second. The math says that playing it safe is the riskiest thing you can do.
Venture returns follow power laws. The top 1% of outcomes generate most of the returns. The other 99% range from "meh" to "tax write-off."
Aiming for 10x instead of 100x caps your upside and usually means you won't even hit the 10x. Power law distributions are unforgiving. There's no participation trophy for "pretty good."
Big bets don't just increase your chances of massive success, they're the only way to attract the things that create massive success. Bold moves get press attention. The best people want to build something that didn't exist before. Your safe approach repels the exact people you need to win. They make investors lean in instead of check out. They give customers something to believe in.
While you're optimizing for quarterly metrics, your competitors are building for the decade. Every hour you spend A/B testing is an hour they spend on something that won't pay off for 18 months but will be impossible to catch up to.
Most importantly, they give you permission to create a new category instead of competing in an existing one. And new categories are where the real money lives.
But what about all the big bets that fail?
Fair question. For every breakout success, there's a dozen companies that swung big and whiffed completely. The startup graveyard is full of bold ideas that nobody wanted.
But here's what the "careful" crowd misses: Being wrong teaches you something. Being forgettable teaches you nothing.
Failed big bets teach you something. They generate stories. They build relationships. Sometimes they even become the foundation for the next big bet that actually works.
Safe bets teach you nothing except how to be more safe. And in a world where venture returns follow power laws, safe is just slow death with better optics.
Your job as a venture-backed founder is to take the right risks, not minimize all risk. There's a huge difference.
Building boldness into your startup
Be intentionally bold, not reckless.
Start with your narrative. Think about your dream headline three years from now and build towards that. What's the change you're trying to create in the world? Not the problem you're solving, the change you're driving. Then ask: “Does everything we’re building ladder back to that change?” If you're spending cycles on things that don't advance your narrative, you're probably playing it safe.
Look outside your category for inspiration. The best ideas usually come from completely different industries. Uber drew inspiration from the ease of ordering from Amazon. Slack drew inspiration from the personality of Twitter.
And stop benchmarking against your direct competitors. They're probably playing it just as safe as you are. Benchmark against companies that created new categories entirely.
You didn't come this far to play it safe
Look, you already made the big bet when you decided to raise venture. You bet on yourself. You convinced other people to bet on you. You raised money from people whose job it is to find 100x outcomes.
So why are you suddenly acting like you're trying to build a lifestyle business?
You're not here to keep up. You're not here to iterate your way to incrementally better outcomes. You're here to build something that changes how people think about your entire category.
The world doesn't need another slightly-better version of something that already exists. It needs something genuinely different. Something worth talking about. Something worth believing in.
You have the money. You have the team. You have the runway. You have everything you need except the conviction to actually use it.
Stop optimizing button colors. Stop copying competitors. Stop hiding behind "customer validation" when what you really mean is "fear of looking stupid."
Make the bet. Build something unignorable. Give people a reason to care.
The safe money is on you playing it safe. Prove them wrong.
Elan runs Off-Menu, a brand studio that helps startups take bigger swings.